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What has been your best crossdressing experience?
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Carolyn Ann Harrington
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High-Femme CrossdresserJul 3
I was wearing a red sweater, black flowing skirt, and black open toe
heels with no nylons (and a red pedi and mani—see photo), and was in a
parking lot at night, where I got out of my car to get something in the
back seat. I have nice breasts. I’m a shoulder-length brunette. An
athletic man alone in a minivan, a Dad I guess, drove near me, parked,
and approached me, asking if I needed help. I said no, I was just
getting something from my car, but I smiled. He was wearing shorts and I
could see that he was erect. He smiled and then drove away but a short
distance from me. He was facing me, sitting in his van, and he was
masturbating. I watched him for a bit as he watched me, and then waved.
He waved back and beckoned to me to come over to the driver’s side
window. He asked if I wanted to watch. Yes, I did. He continued to
masturbate until he came, his spunk arching up in several robust spurts.
I then lifted my skirt, showed him my erecting clitoris, and went back
to my car. We both had stories to tell!

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RAZORHEELS
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Long Time CrossdresserApr 30
Going out on a Saturday night to meet a Gurl for Fun at a hotel event in
a tourist area, celebrating transgender men and women weekend. As I did
not want to stand out as I am 6′2″ tall and dress over the top as you
can see — I wore Black. There were approximately 25–30 girls and friends
at the event, as well as lots of vacationers. Showed up late, and as I
walked to the patio area near the pool all was quiet, started to talk to
everyone and stole the event. Many wanted pictures with me and many
straight and other Gurls wanted to dance, and other gurls wanted to hook
up with me — people started dancing the party started to go strong.
Later that Nite, got invited to an after-party where I had a Blast with
two other Sexy Gurls. Played my dominant role and after a marathon nite
I was drained and sexually fulfilled.

‘

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Juliereed
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Truck Driver at TransportationUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)10mo
when i was 21 i had been crossdressing in private for a few years i was
still hetro thenand had a girlfriend one night late on i was dressing
and decided to go for a drive to the local red light area dressed like a
hooker thigh boots stockings suspenders blond wig tight mini dress
thought I would be good to walk the street I felt great out in public I
walked around for 20 minutes and then headed back to my car on my way
back a guy approached me me and asked for business I was scared and said
no as girly as I could and carried on walking he followed me say you
sissy give me a bj again I said no not wanting him to see my car I
turned down an ally he still following me again he said bj I could not
go to my car so I agreed £15 I said he agreed now to take the first cock
in my mouth I had ever had he gave me the money I dropped to my knees
there in the alley he took out his cock not massive but a good size
about 7iin I took it in my mouth and started sucking at first it made me
gip a bit then I started to enjoy it a hard cock in my mouth from a
stranger on the street I felt like a real hooker sucking for I was worth
my own cock now hard in my pantys all the time him saying that’s good
sissy suck it I was well into this I felt great he grabbed my head and
started pushing it down my thought mmmmm I was feeling really slutty
then it happened I came in my pantys and he pumped his cum down my
throat I felt like a real slut my first cum load ever from a toatal
stranger who just put his cock back in his pants said thanks sissy and
walked away i almost ran back to my car driving home think Sahara a slut
I was I loved the the feeling but have never had the guts to repeat

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Douglas Stephens
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CrossdresserAug 8
My best crossdressing experience happened last year while on vacation.

My wife and I drove to our destination and back home. Before we left
home, I asked my wife if she would mind if I dressed while driving, and
she didn’t have a problem with it.

On the way to our destination, I drove wearing panties, women’s jeans,
women’s shoes, thigh high stockings, bra with breast forms, a woman’s
t-shirt and a wig. The only time I got out was to put gas into our car.
When we were checking in at the hotel, I would remove the wig and breast
forms but everything else I kept on. It was exciting at first, then I
just started relaxing and enjoying the moment.

On the drive back to our house I wore basically the same thing, just a
different t-shirt. Again, I would only get out to put gas into the car.
On the last stop we had to make, the wife suggested that I go into the
convince store and get something to drink. It was a small town in the
middle of nowhere. I was nervous, so I asked my wife to come with me,
and she did. As we walked into the convince store we were greeted “hello
ladies” which made me feel good. We got our drinks and got back to the
clerk, and I paid for it. I didn’t speak, but it was an awesome
experience to go into a store fully dressed as a woman.

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Benin Hose
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Connoisseur of Pantyhose Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsMar 25
For me it was when I let my mother see me in a dress. Mom is in her late
80s and needs assistance so I moved in to help her. After a few weeks of
staying with her and dressing in secret I decided to finally tell her.
During breakfast I brought up the subject and she seemed okay talking
about it. That is when I told her that I like to wear dresses and heels.
At first she had a look of shock but then she says she had a feeling I
did since she had found some women's clothes in my closet. After we ate
she wanted to see what I looked like in a dress so I went and changed.
When I came down the hall the sound of my heels began to get me excited.
My heart beat was racing with fear/excitement of what she might say. I
had put on pantyhose/heels and a little black dress that was my favorite
go to dress. As soon as mom seen me she was speechless and gave me a
hug. I don't wear make-up or wigs ,so from the neck up I am definitely a
guy. She had told me, she had no problem with me wearing what makes me
happy. We went to her bedroom and she gave me some of her outfits that
she no longer wore. Our sizes are the same except for the shoes. She
also gave me some of her silky nightgowns to sleep in. A large weight
has been lifted off my shoulders and we have become like a mother and
daughter when it comes to clothing.

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Sandi Santora
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Studied Business (Graduated 1984)Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020) and
Gweneira Scott
, Masters History, Miskatonic University (1997)Updated Jun 9
Originally Answered: What has been your best cross-dressing experience?
Well, if you really want to know…….. the best or most memorable incident
happened to me in the fall of 2018.

This may be a little long of a story……
I began getting dolled up, shaving from my nose to my toes, applied
makeup, wore a 22"- 24" wavy brunette wig, mini skirt, and a low cut
blouse. (With cleavage) My measurements were 42–35-40 with my silicone
boobs, and corset. I'm 6', 1", 180 lbs. After spending 2 hours plus in
my presentation, I went out to a local dance club called XS. When I doll
up, I get in a very amorous mood……

It was a typical evening out for this cougar crossdresser. I had a few
conversations with females, some dancing, and several drinks. I never
approach anyone when I'm dressed up. (I'm too shy) And I speak only when
spoken to. I smile at everyone who gives me eye contact.

I have found in my 3.5 years of being a CD that women approach me 10 to
1 over men. I like this phenomenon and can't quite understand (yet) why
this is so, but, it is!

Anyway, it's about midnight, and I've had 4 strong drinks that evening.
I had noticed 2 guys throughout the evening keeping their eyes on me as
I was dancing and standing along the railing overlooking the dance
floor. It was quite obvious they were interested in me. They would stare
at me and smile.

When I went to the bar, one of them approached me and bought me a drink.
I thanked him, and We chatted for a couple minutes and I went back to
the railing overlooking the dance floor.

The next time I went to the bar, the other man approached me and bought
me a drink. I thanked him, and We talked for a few minutes, then, I went
back to the railing overlooking the dance floor.

Both men were very kind towards me. They were Average looking, nice
slender bodies, and I'm sure 35 years younger than I. Both were touchy,
feely types.

They both kept their eyes on me and when I returned to the bar area,
both came and stood alongside of me, and bought me a drink. So now I've
got 2 more drinks in front of me, and 2 men on my sides, each trying to
take me home. I loved it!

I was standing between the two of them and they BOTH wanted me. As a
man, my ultimate fantasy was always to have a 3-some with 2
women……..which has never happened.

So now, I've had 6 drinks, and 2 more in front of me. The guys actually
began to argue with one another about who was going to take me home.
From words, it went to a bit of pushing and shoving. WHATS A GURL TO DO?

Heres what I did……….I told them both that I didn't like their behavior
at the moment. They immediately calmed down. And then I said, "I will go
home with BOTH of you but, not one alone". Well, that started with them
shaking their heads no, and the conversation got a little loud between
them once again. (you can't make this up)

I was in an amorous mood anyway……..OK, so, I was horny! I had 6 drinks
in me already, (in a normal evening, I will have 3 or 4) but, I believe
I thought clearly enough to figure out a solution for my personal
safety. And because we were all strangers to one another, and these guys
were literally fighting over who's going to take me home with them, I
gave them my idea, and that was to make love to both of them, or none of
them. They understood.

I told them they have to work it out, and that I would go to a table
(with my 2 drinks in hand) and await the decision. I watched them for
probably 5–10 minutes before they came back to me.

They had agreed to both take me to one of the guys apartment which was
only a few blocks from the club. Well, I still had drinks in front of
me, and as I was finishing my drinks, they had their hands all over me,
and I, them. I had my hands under the table with two nice sized, warm,
hard cocks, in each of my hands. WOW! I've never experienced this
before. I was enjoying the moment! And so were they.

I hadn't finished my 8th drink when the guys wanted to leave. One drove
to the other guys apartment, and I walked with the one guy to his place.
We were kissing and touching all the way over to his apartment. As I
said, I was horny before, and now I'm very horny!

As we went around a building, in the middle of a residential
neighborhood, I passionately kissed my escort and pressed him to the
wall, and, then I went down on my knees, and opened up his zipper, took
his package into my mouth, and sucked him to completion. It didn't take
him but a minute or two to cum. He shivered and squealed with pleasure
as I felt his cum fill my mouth. I swallowed.

We continued to his apartment where the other guy was waiting in his
car. They were complete gentlemen that evening. Doors were opened for
me, drinks were bought, and now both guys are following me up the
stairs. I know they were both looking up at my legs in my mini skirt,
and at my panties and thigh highs. I felt SEXY, beautiful, and desired!

I was!

I was offered a drink, but, I couldn't drink any more, as I didn't need
any liquid courage anyway….I had enough.

I follwed the owner into his dimly lit bedroom and the other guy
followed me. When I sat down on the bed, the love making started
immediately. They were touching and kissing me all over , and I had 4
hands all over me and my clothes came off fast.

When I was down to my pocket bra, corset, and panties, I didn't know
who's hands were who's, who's cock was who's, who I was kissing, who was
kissing me, and then they took of my panties and bra……..and now I didn't
know who was entering my openings because they were sharing me and
changing positions constantly. They fucked me in many different
positions. It was very exciting!

I had one cock in my mouth and the other in my pussy and they felt VERY
GOOD! There was absolutely no discomfort. I wanted them both to cum in
me at the same time, but, that didn't happen. I tried, but, sigh, it did
not. I believe the guy I gave the blow job to earlier (although hard)
couldn't cum a 2nd time. He did fuck me! The other guy did cum in me
orally, and he was very verbal when he did! His shuttering as he cum was
outstanding to feel. I swallowed! I remember how each one felt squirting
cum in my mouth. Both tasted good. Afterwards, we all laid together for
I don't know how long.

Then it was over. The guys handed me all my clothes. I got dressed. And
I left. It was over, but, I had a smile on my face all the next day.

We left the club at 1 am ish? It was a 10 minute walk to the apartment.
5 extra minutes for the blow job I gave, and we made passionate sex
until 4 am! WOW, the time went by fast.

When I got back to my room, it was 4:30 am. I slept well.

To me it felt like maybe an 1 hour had gone by, but, it was 2.5 hours in
bed with these guys and it's the most exciting sexual experience I have
had in my lifetime. There was no pain, as they were gentle, and for all
of us, intense pleasure.

I've been back to that club many times since. I've never seen either of
the guys again. I never knew their names.

And I'll never forget my M/CD/M Sexual encounter. It was my first and
only 3-some, and it was outstanding!

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Nattalie Berenson
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Knows EnglishUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)1y
One of the hottest and best experiences was when I had spent a night
with one absolutely adorable cutie. We had very good sex with a sense of
bdsm and then I aslept. I was dreamful night. Dreams were so erotic but
the best of all the night had came in early morning when I woke up. I
was dressed in a latex suit, had a black lacked corset around my chast
and also I had black heel Pleaser boots on my legs. But that was not the
end of it. My legs were crossed and thight together with a nice silver
and heavy chains. My wrists had been cuffed to the bed and on around my
neck was put steel collar. I was also ballgaged. In the first moment I
didn't know what to think about it. But when that girl who I spent the
last night with came above to me dressed as dominatrix (very similar to
the one in picture down below)

and with whip in one hand and the cock cage in the other hand I started
to feel like the hottest Sissy slave under the sun. Then she did
something I can never forget. She put the cage on my dick, then she
stood on my body while heels of her boots were thrusting deep in my
belly and she started to whip my tits, face, arms and legs. After all
she put the cage out off my dick and sucked my dick. This experience was
the most brilliant I'd ever spend.

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Miki Daniels
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Exotic dancer (2010–present)Upvoted by
Gweneira Scott
, Masters History, Miskatonic University (1997)4y
Originally Answered: What has been your best cross-dressing experience?
One of my best started after I was in the Army. I had crossdresser in
school but I had unsuccessfully joined the Army to stop. It didnt work
and I was already gathering new clothes. This story is about a guy I
worked with and his beautiful and kinky wife.

My friend and co-worker was always telling me stories about his wife,
how kinky she was, how beautiful, how horny, all kinds of things a 20
year old kid didnt need to hear. My friend was into filming different
things, so it was sort of a surprise when he brought in a video of her
sucking his cock. I wasnt sure why he was showing me his private videos,
but it did turn me on.

So, one Friday after work, he invited me to his house for a barbecue. I
was a little nervous meeting his wife, because I had seen her movies. We
entered the house and I saw her for the first time, blonde, 28 years
old, absolutely beautiful. She was wearing a yellow bikini top with some
kind of wrap covering her long legs.

She hugged me and I felt her firm breasts push against my chest. I guess
she could see how embarrassed it made me. She said it was so cute, as
she flirted with me. Her husband, my friend, Ron just watched and
smiled, drinking a beer. Nobody else was coming for dinner, so I felt a
little uneasy.

But, I did enjoy talking to his wife, Lea. She was a doll. Ron would
seductively kiss her as I watched, not knowing what to make of it. Ron
was into smoking pot as was Lea. They did other drugs, but I wasnt into
any kind of drugs. But it was fun to be with them.

Ron started getting more and more out of it. At one point, he pulled
Lea's wrap off her, exposing her very small bikini bottoms and long
tanned legs. She caught me looking and just smiled. I watched Ron run
his hand down between her legs and rub her nice round mound. She told
him to knock it off, since she said he was in no condition to follow
thru, so unless he wanted me to finish what he started, he better stop.
I guess i blushed at that remark and she just smiled again. Ron wandered
off to bed.

Lea invited me over to the couch and we talked. She seemed to enjoy
hearing i had only had sex with a girl one time, teasing me about being
an “almost virgin". I had been drinking beer and felt relaxed. She asked
me all kinds of things and I got very comfortable with her. She was fun
to talk to. But as we talked about girls I knew, I let it slip that one
girl was always after me to dress in girls clothes for her. Lea asked if
I ever did and I told her I couldnt do that. She asked why not? She said
I was so cute that I would make a pretty girl. Lea asked what the girl
wanted to do. I found myself telling her that the girl wanted to dress
me as a sexy girl, then watch me make love to a guy, preferably a black
guy. I asked Lea if that wasnt pretty strange. Lea thought for a minute
and then said she thought it would be hot.

At that, Lea bent over and kissed me. She took my hand and slid it down
her flat stomach and into her bikini bottoms. She pushed my hand down to
her pussy, which was incredibly wet. She looked at me and asked if it
felt like she was turned on by the idea. I mumbled something that
probably made no sense and she said that she had fucked a few black
guys. She said that since they lived over a bar called The Black Forest,
she met a lot of black guys. I thought it was a German themed bar, just
to show how naive I was.

Anyway, I was really afraid of Ron catching us, so I told her I had to
leave. She said she was sure Ron would be OK with it if I wanted to
..make love to her but I decided it was best that I leave. I left, but I
wasnt sure it was the best choice. The next day at work, Ron asked me
how I liked Lea and I told I'm I thought she was pretty cool. He told me
she really enjoyed talking to me and asked if I could come back.

A few days later, Ron asked if I could come over and spend the weekend
while he was in training at another military base. He said Lea didnt
like being at home alone for long periods. I told him I guessed I could,
since I had no work scheduled. He said Lea would be grateful for the
company.

So, that Friday, I went home with Ron and Lea and I took him to the
airport. When we got back to her place, she fixed is some dinner and
then we sat and talked. Lea excused herself to put on something more
comfortable and came back in a thin white lace dress. I tried not to
stare, but I could see her nipples. As she sat down next to me, I could
see she wasnt wearing panties. This was going to be tough.

She said she had been thinking all week about what I had told her about
the girlfriend that wanted me to dress like a girl and have sex with a
black stud. I was really embarrassed hearing her say those words. I
guess it was a turn on but I had never shared this kind of personal
stuff with anyone.

Lea said she wanted to see me slip into something more comfortable. I
told her I only had Jean's and t-shirts. She told me to wait a minute
and went into the bedroom for something. She came back with a pink
babydoll nightie and panty set. I told her I could wear that and she
said, “Of course you can, it's just us here. Nobody will know and you
will find it relaxing.” With her coaxing, I went into the bedroom and
put the sexy nightie on. I was very nervous, but I walked out and joined
her. She said, “That's better, right?” I sat down on my end of the couch
and we talked some more. She kept looking at me and finally said, “You
really are cute, almost too cute to be a boy. I bet with a little
makeup, you would easily pass as a sexy girl.” I felt my face warming as
I blushed.

Lea took my hand and led me into her bathroom. She applied a creamy
lotion and then used a razor to shave my face. She then started putting
makeup on my face. I just sat back and enjoyed having her soft hands
touch me. I kept sneaking peaks at her ass when she bent over. I could
see her ass and her pussy as she bent over, making my cock get hard.
Then, as she turned to apply some more makeup, she rested her hand on my
upper thigh. I couldnt help but shudder when she did that. She looked at
me, smiled, then let her fingers stroke my hard cock in my panties. She
asked,”Are you having fun now?”

When she had finished my makeup, i was amazed at how sexy i looked. I
thought i was really pretty. Lea told me to wait and went into her
closet and brought out a long brown wig and put it on me. She stepped
back and looked at me and said, “You really do make a pretty girl.” She
got Ron's camera and took some photos of me. She promised to get rid of
them before Ron got back.

We went back to the couch and Lea brought out some wine and we sat and
drank. Lea offered me a small pill but i declined. She took hers, she
said it helped her relax and i should try some. I told he i just wasnt
into any kind of drugs. She said that was OK. She moved over closer and
hugged me. She put her hand on the side of my face and gently turned it
to face hers, then she kissed me. It felt special to make out with her
as i looked across the room at the large mirror. It was like watching 2
pretty women together. Lea took my hand and put it between her legs. She
used her hand to push my fingers into her juicy pussy. She held them
there and said she was cumming, as she massaged my hand against her.

We took a little break and drank a little more. She said she had been
thinking about what the old girlfriends fantasy had been, watching me
making love to a well hung black guy. I wasnt drunk enough to not be
embarrassed. Lea sensed that and got up and got me another glass of
wine. She asked what I thought of the fantasy and I found myself telling
her about being really confused when I was younger, enjoying sexy
lingerie and wondering if I should have been the girl my mom always told
our friends and relatives I should have been.

Lea hugged me again and told me I was fine and I shouldn't be afraid to
experiment. We started making out again and Lea took my hand a led me to
her bed. I told her Ron was my friend and she said she had already asked
him if she could make love to her and he said as long as she took
photos, he was OK with it. We got into bed and I felt so sexy, wearing
the sexy nightie and the wig. Lea told me to pose, so she could get some
photos for Ron.

She said Ron got excited when she told him about the girl that wanted to
see me dressed like a girl making love to a black guy. She said he had
fucked her several times while they talked about it. I wasnt sure how I
should feel. Lea got us another glass of wine and climbed back into bed
with me. I was feeling strangely out of control but I wanted to make
love to this beautiful woman.

Lea pulled me over on top of her and spread her legs. She reached down
and pulled my cock out of my panties. She guided my cock into wet pussy.
Damn, it felt so velvety smooth and wet. Lea was kissing me, her tongue
probing my mouth as she encouraged me to fuck her. To my embarrassment,
I came rather quickly. She said it was OK, we had much more lovemaking
to do. She looked at me and gently said, “Eat me, baby. Eat my cum
filled pussy.” I slid down her body and between her legs. Her hands
grasped my wig covered head and told me to please eat her. She pushed my
lips against her wet opening and I started licking her, I mean, our
wetness from her pussy.

Lea then rolled me over on my back. She pulled my panties off Nd started
massaging my cock. She asked me if i liked eating her and i told her i
did. She said i was making her so wet. She reached down to her pussy and
inserted 2 fingers and brought the cum-covered fingers to my ass. She
spread my legs and massaged our cum into my ass. She kept repeating
this, asking how it felt. I just moaned as she continued. At this point,
I felt pressure against my ass and looked down to she had retrieved a
large fake penus and before I could object, she slid it into my ass and
started fucking me with it. She finally told me to fuck myself with it
as she got up to take a video camera and film the event. I was feeling
really turned on and out of control as I fucked myself with the large
fake penis. As I fucked myself, my cock shot a huge load of cum out onto
my lower stomach. Lea was still filming as she told me to put my fingers
in my cum and lick them. I did as she said, several times. I still
couldnt understand why I was doing these things but I was liking it.

Lea told me she needed more cock and told me to keep fucking myself
while she went down stairs to the Bkack Forest. She was only gone a few
minutes before and came back with a nice looking black man. She took of
her clothes and helped the black guy out of his. He was just looking at
me on the bed, as I fucked my ass. Lea bent over the bed and her mouth
found my cock. The black guy stepped up behind her and I watched as his
large cock slid into her wet pussy. She moaned as she sucked my cock,
pulling off just long enough to tell her stud to fuck her pussy. He took
the order seriously and started hammering her ass. He fucked her
furiously for about 10 minutes before announcing he was cumming. Lea was
shaking and telling him to please cum in her pussy. As he finished, Lea
asked me if I would lick the cum off her guest. I dont know why, but I
sat on the edge of the bed and started to lick the cum off the large
black cock. But before I knew it, the cock was being forced into my
mouth. Lea was saying, “That's it baby, suck that cock, eat the cum.” I
saw the camera flash and Lea grabbed the video cam and started filming
me as I sucked this huge cock. The guy was telling me to suck it,
calling me a little faggot, as he fucked my mouth. But I wanted to make
him cum. I wanted to eat his cum. I was in a strange blur as I gave this
guy head. He announced he was cummjng and grabbed my head and started
pumping his cum down my throat. I felt so sexy, being this guys bitch.
He finally left and I heard Lea tell him she’d like him to bring a few
horny friends back the next night.

Lea pushed me back on the bed and sat back on my chest, she slid back
until her wet pussy was against my mouth and she told me to eat her,
again. This time, she was wetter than before, and her inner thighs were
covered with cum. I licked her thighs, her engorged pussy lips, even her
tender asshole. She was grinding her pussy into my mouth, begging me to
eat her, to please eat her. I was not myself as I sucked the huge amount
of cum out of her dripping pussy. I couldnt get enough.

Finally, exhausted, we went to sleep together. I awoke very groggy, but
feeling pretty good. Lea was laying next to me, just looking at me. She
said I really was fantastic the night before and asked if I had regrets.
I had to tell her that I had a really good time. She asked if I
remembered sucking cock the night before. I told her I did and started
to apologize but she placed her hand over my mouth, telling me I should
be proud because it was really sexy. As we talked, I watched her fingers
find her pussy again and she asked if I wanted to fuck her again. We
spent several hours just fucking.

Lea said she wanted to really fix me up, to make me even more sexy as a
girl. That afternoon, she helped me take a bath, where she shaved my
legs and body. As she was shaving my pubic area, my cock got hard. She
stopped long enough to give me a nice blow job. She then did my makeup
and wig again and helped me dress in a black bustier and thigh high
nylons and a pair of black stripper heels. She had me slip on tiny black
thong panties, then a very short black mini dress. She either took
photos or videoed me as she worked.

She got us more wine as she got ready. After the second drink, Lea asked
how I felt. I told her I felt very strange, very relaxed but OK, like
the night before. Lea showed me a small pink pill and said I should
thank it. She didnt tell me what it was but to just go with my feelings.
Lea asked if I wanted to do the things my old girlfriend had wanted to
see in her fantasy. I told her I didnt know. Lea said our friend from
the night before was coming back with some friends and she wanted to
watch me make love to them, to do a gang bang with them.

We sat and drank as Lea got the video camera set for the evening. I was
still unsure and asked if I could have another pill and she said I could
do half of one. I took the pill and she said Ron would really have liked
to watch me being a girl. She said he would have the videos and photos.

Then, there was a knock on the door. Lea looked at me and asked if I was
ready. She asked how she looked in her short red dress. As she bent
over, I told her she would look better without panties. She said I was
probably right and stepped out of them. She opened the door and greeted
6 well built black guys. After they came in, she told them that she
wanted to film them fucking my sissy ass and having me suck their cocks.
She said anybody that wasnt interested could leave. Nobody left.

Lea turned up the music and brought out the booze. As they drank and got
relaxed, Lea led one of them over to me and told me I should suck his
cock. Lea then told the rest of them to get naked. I was busy sucking
the first guy when another cock presented itself. Just then, the first
guy filled my mouth with cum. Lea told me to open my mouth and show the
camera the cum, which I did. Then she told me to swallow and show her.
The guys seemed to get off on that a d I was soon sucking all 6 cocks.
One guy was absolutely huge, probably an honest eleven or twelve inches,
but I managed to make him cum.

The whole time, they were talking about what a great little faggot
cocksucker i was, making me feel good about pleasing them. Lea came over
and removed my dress and i had the urge to get out of the panties. As i
stood there in my sexy lingerie, Lea filmed. Then, one of the guys
pushed me back on the bed. Lea had already filled my ass with some kind
of slick lubrication and as i spread my legs, the first cock slid into
me. I felt wonderful as his hot cock fucked me until his cock filled my
ass with his cum. The next guy had me on my knees, on the bed. He buried
his cock in me and fucked me furiously until he came. I fucked and
sucked until it was the biggest guys turn. By then, i was stretched out
and very wet and i took his cock easily while the others watched and Lea
videoed the action. I guess it got to be too much for Lea, because she
locked down the camera and brought a guy to the bed. I watched her fuck
the first guy, then the second, then all of them. My lover was still
fucking me as i watched Lea enjoy the multiple partners.

They finally finished and Lea and i thanked them for coming up. They
said they would be happy to come up anytime we wanted to fuck. After
they left, Lea sat down next to me, spreading her legs, asking me if I
ever saw a pussy that wet. I told her I hadnt. She then asked if there
was anything I'd like to do with it. I found myself licking my lips and
telling her I would love to eat her out if she wanted. She said, “I
want. My pussy is full of cum and I want you to eat me.” I spent an hour
eating her pussy and having her fuck my ass with her large dildo.
Afterward, she fucked my mouth with the big fake cock, asking me if i
was now a real cocksucker, a if i really liked sucking big black cock. I
told her i was a faggot cocksucker and loved big black cock. At that
point, Lea turned off the camera. She said Ron would love it.

I dont know what happened to that video or who watched it. I did find
out that Ron was in a small group of Army guys that made and shared
videos. Ron did bring a couple of officers up to meet me, telling them I
was the sexy girl in the videos. Luckily, I got orders and moved on to
another location.

But I always think back about how Lea helped me to understand that I was
really OK and it was OK to follow my dreams.

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Jenni Gee
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Loves a cute pair of bootiesUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)4y
Originally Answered: What is the best crossdressing experience you have
ever had?
I was in my early 20s and had met a married man who traveled to Chicago
on business on a monthly basis. He was introduced to me by my boss at
the time who told his friend Tony “I would help him with whatever he
needed”. Fresh out of college, I wanted to make a good impression on my
boss and a guy who was a big deal when he came to our hotel. Three or
four months passed and there were a few meaningless things I had done
for him but his glowing review to my boss was all I cared about.

One afternoon I get a call from him that he needs a gift picked up from
a store and delivered to his room. I get the details including that it
was in the lingerie department ready for pick up after 4pm. There was a
slight delay in getting the order ready but it gave me a few minutes to
browse. These weren’t the bra and panties I had bought for myself. I
peaked at a few of the price tags and couldn’t believe of expensive some
of the items were. The woman brought me the package with the message
that if something didn’t fit right to bring it back and she’d take care
of it.

I got to his hotel room, package in hand, a little after 6pm. He was on
the phone but told me to come in. He opened the package and took out a
very cute white lace bra and panties. I pretended not to look but
couldn’t help think how I’d love to have them. He hung up his call and
asked what I thought of his gift? I told him they were nice, very cute.
He walked over and handed them to me.

He explained there was one occasion before he thought I was wearing a
bra. He confirmed it when he saw a bra strap marks one day when we were
changing to play golf. In face, he said he was pretty sure I was wearing
a bra at that moment and he was right. So there I was, holding very
expensive lingerie in a hotel suite being outed as a crossdresser by a
seemingly understanding guy who is a good friend to my boss. Needless to
say I was speechless. I could feel my cheeks turning red.

He asked me if his assumption was correct? I sheepishly told him he was.
He told me not to worry and not to be embarrassed. He said to go try
them on come out and show him how it looked. He poured himself a drink
and pointed to the bathroom to go change. Part of me was scared shitless
while the other part, sinfully aroused. I stripped down, taking off the
cheap bra I was wearing, and slid on the panties first then put on the
bra. Both fit perfect. I reached for the door handle and thought I’m
either getting a raise or getting fired for this. I walked out into the
suite and walked toward Tony. He looked up from his file and gave a nod
of approval and motioned for me to come closer. Standing next to him,
his hand rubbed the lace material over my ass and then gave it a light slap.

He told me I looked great and that we would build on this. He asked me
how far I was willing to take this. I wasn’t sure what “this” was but I
told him I was willing to try anything (thinking to myself, I’m so fired
or ready for a promotion). He had a dinner meeting at 7pm. He said I
could go and that the bra and panties were mine to keep. I needed to be
back at his room at 3pm sharp tomorrow.

I had been crossdressing for a few years and had some fun experiences.
College was a little on again off again but now graduated, in my own
apartment, with a job, I was starting to buy some things, experiment w
make up, and had been with a few guys as well. Tony was a completely
different league though. Successful. Good looking. He was what I wanted
to be. Right now, my goal was to please him.

I showed up the next day and let myself into his room. There was a black
dress, lingerie, shoes, and a few other items laid out on the bed. I was
looking for a note or some kind of direction from Tony. There was
nothing. A few minutes later there was a knock on the door. It was a
woman from the spa. She recognized me and identified me as Tony’s
“special fiend.” She told me my secret was safe with her, Tony had taken
care of her.

She had what look like a tackle box that ended up being her traveling
make up kit. WTF had I got myself into? I flashed back to being made up
as a teenager but here I was a 20 something professional, playing
“girlfriend” to some rich businessman. Confused, scared and highly
intoxicated at the prospect of what was going to happen, I was ready to
get started.

Debbie had specific instructions from Tony for me to follow, making sure
I was shaved and as perfect for him as possible. Then it was into
Debbie’s makeshift makeup chair. She had produced two separate wigs as
well. She said it was time to work her magic. I’ve never done my make up
like she did. We tried both wigs, settling for a shorter sandy blond. By
the time she had walked me through dressing, put on a cute pair of
heeled booties, I was amazed at the transition.

She said she was certain Tony would like it. She put a few items in a
small purse for me in case I needed to freshen up as the evening
progressed. I asked if she knew where I was heading but she produced a
bottle of Champaign and told me Tony would be there shortly. She poured
a glass for me, told me to act natural and have fun. And off she went.

I was a few sips in when Tony arrived. His silent head nodding followed
by a “you look amazing” was all I needed to hear. I walked over and gave
him a kiss on the cheek and thanked him. I told him I’ve never felt so
amazing and it was because of him. He held my hand and pulled me back
toward him, paused and then kissed me on my lips. He started to pull
away but I wanted more. I kissed him again but this time neither of us
stopped.

Tony stopped us after a minute. We had plans. He had to change and I
fixed my lipstick. About 10 minutes later we were heading out the door
and then it hit me. I was walking through the hotel I worked at, in a
public area for everyone to see. We made are way down the elevator, the
lobby and to the waiting car and I realized that all anyone saw was a
rich dude and his girlfriend. My heart stopped racing once the limo
started to pull away. Tony said I looked amazing.

We ended up at an art show. Neither of us really wanted to be there but
it was a friend of Tony’s so he was obligated. No one looked twice at me
in a suspicious way at all. My confidence grew by the minute, sipping
Champaign and walking with him. We ended up having a great time. We
stayed for a few hours and then headed back. The car ride back resulted
in giving my first limo blowjob, getting a chance to taste all of him. I
was in love.

We got back to the hotel and were enjoying each other in the room. Tony
was a great kisser and had an amazing cock. It wasn’t long before he was
stripped naked and me down to my bra and panties, in bed. After a good
amount of touching, kissing and cock worship, i felt his cock rubbing
against my ass. Then his finger slid in with a little lube.

I remember the head of his cock slowly moving inside me and the feeling
of him slowly filling me up. And then, when I felt his hips again my
ass, he stopped. I could feel him swelling inside me. All of him. Slowly
he began to slide himself in and out of me. We were in perfect rhythm
and about ten minutes of his cock fucking me, I felt him cum in me, shot
after shot filling me up. The most amazing feeling knowing he was truly
inside me in every way possible.

We had sex twice more that night and it was the start of an incredible
two year relationship. Those were two of the best years of my life
getting to be Tony’s girl, Jenni. Our story only started with that
night. But all great things did come to an end. Tony sold his business
at one point, retired and we broke things off. Some heartbreak. No
regrets. An amazing time that easily was my most memorable time Getting
to be Jenni.

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Marian Andersen
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Mature crossdresser who loves dressing whenever possible.Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)3y
Originally Answered: What is the best crossdressing experience you have
ever had?
Believe it or not, It was being caught by a policeman and being taken to
the Police Command Post trailer in handcuffs! He stopped me while I was
out one winter evening enjoying a nice drive while dressed quite
lavishishly: thigh high heeled boots, pencil skirt, long black sweater,
winter coat, handbag, fully made up and wearing jewelry and a shoulder
length wig. I was feeling adventurous and quite feminine. I went to
various malls and walked thru their parking lot to the doors of several
stores where people were entering and exiting. I usually go out at night
but not to such crowded places. But I had on a heavy coat and boots so I
blended in well. It was thrilling to be walking among the various crowds
of people as a woman shopper. After a few hours, I decide to take the
long way home, but I dropped something at my feet and reached down to
get it (I did not want it to lodge under my brake or gas pedal).

Suddenly, blue and red lights are flashing behind me. By reaching down,
I inadvertently was swerving outside my lane. I stopped but could not
find my registration and tried telling the policeman my enfemme name. He
made me, but was not sure if I was transgender and legally had changed
my name to Marian A. After several calls to HQ with no acknowledgement
of a Marian A., he asked me to come clean. I told him my real name and
hoped that would satisfy his persistence. But although I passed the
breath analyzer test, he thought I may have been on drugs due to my
swerving on the road, so my car was impounded and I was handcuffed and
put in his patrol car to go take a drug test.

Surprisingly, at the Police Command Post, I was treated very courteously
as a female by both the female and male staff members, even the
policeman had loosened up and continued to call me Marian even though he
knew my male name. They told that since I was presenting as a female
they would treat me as such. They said not to feel ashamed or
uncomfortable about dressing and presenting as a female. They said
crossdressing was quite common and very prevalent in today’s society and
that I was well dressed and acting civilly. Even when other “guests”
came in escorted by policemen, I was constantly referred to as “Marian”
in their presence.

Although I was there for several hours, we had a delightful conversation
about my clothes and my crossdressing. They treated me as a woman the
whole time and let me go to the unisex toilet. Of course the toilet seat
was up! But not for long as it then crashed down very loudly as I was
preparing myself to sit on it. All I could think of was that I had now
convinced them that I was not merely a crossdresser but actually a
transgender female!

When the EMT took my blood he was very gentle and courteous. I was told
that no record of my arrest would be kept if the drug test was negative
(it was). Eventually, they called a cab for me and the policeman took my
hand as I walked down the steep steps in my heeled boots. He then walked
me across the parking lot to the waiting cab, opened the door for me and
said goodnight MARIAN as he closed the door. I rode the several miles to
within a block of my home. It was about 3am and I did not want the cab
to stop for a while under a streetlight by my house; have the door slam
shut with a female exiting to my house where no female lived! I felt
more confident to walk the block to my home and then suddenly turn
quickly up my walk to the door as quickly and quietly as possible.

I had made it! I then sat down and reminisced about how elegantly I was
treated by the police staff. I realized that after spending nearly three
hours as a female conversing with other people and being accepted as
such made me comfortable talking with a female voice and brandishing
female mannerisms: crossing my legs, gesturing with my hands, taking off
my coat to show off my figure, and walking the length of the trailer
every so often (with a wiggle) to stretch my legs. Again the women were
nice and smiled which further encouraged me. Now, it was time to go to
bed, and after I undressed and put on my nightgown and matching panties,
I laid in bed thinking: Yes, it was the best experience I ever had
crossdressed!!

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Assala Shamsi
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Adult Model at Faphouse (2020–present)
·
Mar 15
I really love Crossdressing. From the childhood I wish that I'll be like
my mother as a house wife. And when my elder sister married my instincts
got increase she looked so beautiful in bride dress. till the I decided
to wear my elder sister dresses. And talk with the guys online to
encourage me.

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Samantha Hopkins
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Bi-sexual CrossdresserFeb 1
My boyfriend and I went away for a long weekend skiing in Vermont.
Skiing has alwys been one of my favorite things to do in girl mode.
Women's ski outfits are uber sexy and feminine. Because of hats and
scarves is really easy to pass and no one questions. My first excursions
as a girl were to go skiing.

So we are having a great time and are walking through the parking lo to
our condo we rented. And this lady calls my boyfriends name and we both
freeze its his grandmother. I don know how he is going to react, no one
knows about us. My BF introduces me as his girlfriend and in the dimming
light I feel confident

Then his sister shows up and we do the introductions again.

Now in the bright lights of the lobby, We scurry to get Mikes sister and
his grandmother onto the elevator. Everything is going good.

Then we hear mikes sister very loudly say “I knew it !!!” “I Knew it all
along”

Then she starts wagging her finger at me and saying “You, you !!” “Its
You !” “I Know who you are”

Then she says I am not going to tell a soul. I have known about you
since high school but I just couldn't prove it. You guys outlasted my
first marriage,

So the next day we all skied together. and we had a great day. It was
amazing.

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Meran Berwyck
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CrossdresserJul 28
Originally Answered: What is the most special moment on your
cross-dressing journey?
I was dressed up and visited an adult novelty shop as one of my male
friends was working there. He knew I was a crossdresser so it was no
surprise to him. He asked me to watch the shop while he went to get
himself some cigarettes! I said okay. While he was out, two young women
came in to shop. They chose a few items and came up to check out. I
asked them in the most feminine voice I had if they found everything
they wanted. They said yes. When I told them their purchase total, my
voice changed and they suddenly realized I was not a real woman. But
they were very impressed and began looking me over and complimenting my
choice of clothes, especially my gold knee-high boots. The asked where I
bought them, I told them FOH by mail order. The kept checking me out
until I had bagged up their stuff and they walked out, They were really
nice and sweet to me. I was on cloud nine. I had initially fooled them.

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TRANSEmilyxo2022
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Fucked and creamed by 11 guys Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)2y
Originally Answered: What was your best experience in cross-dressing
publicly?
Having my first anal with a stranger at a public look out i was on my
knees and hands with my ass up in the air when i felt a cock slide
inside of me for the first time ever i cant describe how dam good it
felt too it was so amazing when he began to fuck me so dam hard his
balls slapping against of me every thrust all i could say to the guy is
“cum inside of me i want your cum deep inside me i want you to fill me
up now “ He fucked me harder and harder he was treating me like a true
slut He started groaning while he grabbed me by my waist with both hands
i felt his cock swell and twitch inside of my ass as he was pushed all
the way in me he gave me a couple more thrusts before moaning so loud
and then said “here it is slut im cumming oh fuck yeah baby your a good
slut”I felt a warm gush and could feel his cum filling my ass up until
his balls were empty then he pulled out of me a big stream of warm thick
cum followed ooozing out of me

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Jamie Richards
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Crossdressed since age 10Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)Updated 5y
Originally Answered: What's the greatest time you had while crossdressed?
I went to a gay club on Halloween with a young lady who was close to 30
years my junior and who liked crossdressers. I was 53 at the time and
she told me she was 18, but she later confessed that she had a 10 year
old daughter. She came over to my house and helped me to get dressed up
as a woman. This was one of the first times I went out in public dressed
and we must have looked good as we approached the club on foot as
someone asked if they could take a picture of us. Once inside, I was
playing pool with her and it was such a rush to bend over the table with
my short dress hiking up behind me and my cleavage showing for the folks
in front of me. Later on, I sat the bar by myself while she was playing
pool with someone else and I felt so comfortable and, apparently, no one
figured out that I was a man. A friend of my brother-in-law came up and
sat next to me, but never figured out that it was me, even though we
knew each other pretty well. I didn’t introduce myself because I didn’t
want my brother-in-law to know that I cross-dressed.

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Joanna
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a trans girl for 4 yearsUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)1y
I still remember it is a crossdressing party.When I was 18 years old, I
attended a crossdressing party. I knew this party from the local trans
forums. Actually, I was afraid to meet some familiar people. But as this
party was 50 km away from my block, I came to see some new friends.In
the party, I found many hot guys. I admited that I liked to date with
hot guys. On the party, I got many phone number. I wore as a bunny. I
thought this could be a nice sytle for me. Many people came to chat with
me. But I could also feel most people came here for casual dates. If you
want to find serious relationship, it is very hard. In order to be back
home, I didn’t drink too much but I found so many people drunk a lot.
Now, I am trans woman and I know guys on some trans dating sites. But
there are also many crossdressing men who are looking for dating.

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Starla
·
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Former Hostes at Gay Bar (2012–2014)
·
Apr 6
I went to a gay bar, and was hit on several times. The owner didn't have
any help so I offered to help. I helped him close he payed me and
offered me a job. I was only able to work for one week.

… (more)
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George Fraser
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Studied Mathematics at Arapahoe High School10mo
Originally Answered: What has been your proudest crossdressing
experiences ever?
when I had the courage to buy my first pieces of lingerie at Dillard's
and Macys. I was so nervous, and I know the sales lady noticed. She
asked me if she could assist me, and I said yes but I do not know my
size. I was looking at the rack of baby doll nighties and the long
gowns. She said how tall are you? I said 5′10″ she said OKAY. now the
long gowns that will fit you, so they do not drag the floor are here.
And the baby dolls are next to them. Do you have a bra size? I said no,
need help with that too. She took me into the changing room and tape
measured me for size. She said if you were to wear forms, I think a 36C
will work just great for both your gowns. She took me to the bras and
panty section and told me it is always wise to purchase your bras and
panty that match. And get your bras underwired to assist in holding
breast forms in place.

I spent over an hour at the store and purchased 186.00 worth of very
pretty and sexy lingerie. At the checkout I heard the sales lady tell
the clerk. I will check him out. She asked if I found what I was looking
for? and i said yes and thanked her so much for all her help. She gave
me her card that had her store hours that were on the back. She said
call this number I work 3 days a week and If I’m here I will assist you.
Her name was Karen, and she just made my first encounter so memorable.

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Joanne Watters
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Former Dancer (1991–1992)Feb 8
Originally Answered: What is your favorite experience you had while
crossdressing?
While I was still married to my first wife, I was really getting into my
dressing up, I started making noticeable changes to my appearance. I
grew my fingernails out & kept them shaped & polished with a light pink
polish, I had my ears double pierced, I had my eyebrows waxed pencil
thin with a high, feminine arch in them & I had my hair cut & styled
into a very girlie look. My wife threatened to tell everyone I knew
about my dressing up as a girl if I didn’t stop dressing up. I told my
wife to go ahead & tell everyone because I wanted to live as a girl full
time. A few days later, my wife told me she was coming home with two of
her girl friends Tuesday after work so I better not be dressed up, I
told her that I didn’t care if her friends saw me dressed up, in fact I
want them to see me as the girl I want to be, my wife got pissed off at
me & said to go ahead & get dressed up like the sissy I am & she will
just tell her friends that she married a sissy, faggot who wants to be a
girl & be with men, I told her to tell her friends because I will be
completely dressed as a girl when they get home. My wife normally gets
home from work at 6:00 p.m. so on Tuesday at 5:00 p.m. I was sitting on
the sofa, wearing white panties, matching bra, super shiny, suntan
pantyhose over my completely shaved body with dark red nail polish on my
fingers & toes, I had on a white, button up the back, silk, long sleeve
blouse, tucked into a black, belted, mini skirt, I wore black, open
toed, four inch heels with an ankle strap, my hair was nothing but a
mass of curls, my makeup was done to perfection & my ultra thin & highly
arched eyebrows gave my face a ,feminine look. The extra large silver
hoop earrings that swung from my pierced ears when ever I moved my head,
drew attention to my perfectly made up face. I sat on the sofa with my
legs crossed like a woman as I got out my nail polish & gave my
fingernails another coat of dark red polish. As I started on my other
hand, I heard the front door open & people talking, I continued to
polish my nails. My wife led her two friends into the living room, upon
seeing me sitting on the sofa, polishing my nails, my wife stopped dead
in her tracks just staring at me in disbelief. I finished my last nail &
put the cap on the polish then looked up at my wife with a slight grin
on my face. My wife came to her senses & told her friends, this is my
sissy husband, as you can see he want’s to be a girl, the two girls
laughed as I said hello in my best female voice. My wife told her
friends that she didn’t know that I was going to be dressed as I was or
she would have told them beforehand, her friends said that it was no big
deal then the one girl said I was quite good looking, I looked at my
wife & smiled at her. My wife then said, well, this sissy has had lots
of practice dressing as a girl, she has been doing it all his life, one
of the girl’s asked my wife if she knew that I liked dressing up like a
girl before we got married & my wife told her that, she didn’t know that
I wanted to become a woman & be with men, the other girl asked me if I
really liked men, I looked at her & said, yes, I really love being with
men, I don’t have a boyfriend right now but I would like to, the other
girl said were going to have to find you a boy friend, that would be
nice I said. Later that night, when my wife got back from dropping off
her friends, she said, I don’t believe you let my friends see you
dressed as a girl, I looked at my wife & told her that I have told you
many times that I want to be a woman & that I really want to be with
men, maybe now you will believe me.

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Ami-Nimi Singh
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Msc in Master of Science in Chemistry, University of AllahabadJul 31
As I reminisce about my past, I am transported back to a singular moment
in beginning of 2019, when my life was a picturesque tapestry of joy and
contentment in Prayagraj. During my college days, I shared a memorable
experience with my then-girlfriend, when she stayed with me for a week.
With my distant relatives away, we had the privacy to indulge in various
activities (excluding intimacy). Our days were filled with laughter,
adventures, and deep conversations, creating an unbreakable bond between us.

One day, we playfully engaged in a role-reversal experiment, where I
donned her attire, and she wore mine. She skillfully applied makeup to
transform me into a feminine version, while she embraced a masculine
persona. We immersed ourselves in this swap, relishing the novelty of
our reversed roles. We played games, cooked together, and even mimicked
each other's mannerisms, creating a hilarious and unforgettable
spectacle. The experience was nothing short of enchanting, and I cherish
the memory of that day, frozen in time, a testament to the joy and
creativity that our relationship embodied.

While I've repeated this playfulness with my second partner, the
memories of that first time remain special. Perhaps, I'll revisit this
playfulness after marriage, who knows. I miss those carefree days of my
life. We enjoyed in every possible way we can.

thanks for reading.

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Cammie Jones
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Dress at least weekly, have taken en femme tripsUpvoted by
Gweneira Scott
, Masters History, Miskatonic University (1997)3y
Originally Answered: What has been your proudest crossdressing
experiences ever?
What has been your proudest crossdressing experiences ever?

I wanted to say the first time out in public but that is not it. Last
year I spent 10 days en femme with a week of that in Hawaii. That meant
I was dressed as I packed and made a couple trips for last minute
necessities. The morning I drove to the airport had me on full blown
nerves. I checked in and showed my ID to the gate agent. As my bag
disappeared on the conveyor belt I knew there was absolutely no turning
back. Next was the TSA encounter. The ID checker said thank you mam as
he handed my male ID back. I spent the entire trip as Cammie and loved
every minute as I sunned at the pool, played at the beach, attended a
luau and ate at the restaurants.

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Michael
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Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)Jan 18
Originally Answered: What has been your proudest crossdressing
experiences ever?
More Than One 2 B Honest

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Jaime
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Being sexually used
·
Mar 16
The best experience I have had crossdressing was a night I was fully
dressed in lingerie, a sexy dress, wig, makeup and thigh high boots, a
guy took me to a club, we ran into a friend of his who liked what he
saw. Long story short they took me back to his house and used me so
good, I never felt so good, the desire these guys had for me was
exciting and I was very eager to please, it was the only time I ever
sucked a cock while getting fucked
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Stephanie Cain
·
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AS in Medicine and Healthcare & School of Common Sense, Crafton Hills
Community CollegeUpdated 4y
Related
What is the best memory that you have as a crossdresser?
I met a magnificent girl in highschool. We had several wonderful
adventures involving my cross-dressing. After dating for about 3 years,
we married and left town for the first week of our two week honeymoon.
She wore a beautiful white wedding dress because she was a virgin and I
wore a black tuxedo when we took our vows in front of almost 100 guests.
During the week we were gone, her best friend Kathy altered the dress so
it would fit me.

In a very private ceremony, in Kathy's and Richard's backyard, we
exchanged vows for the second time. Seven people witnessed me in our
white wedding dress because I too was still a virgin and she wore a suit
and tie. Kathy was the “Best-man” and Richard, who is also a
crossdresser, was the “Maiden-of-honor” for us.

Richard presented me, the “Bride”, with some beautiful white lace
lingerie to wear before the ceremony. As he helped me get dressed, he
said that only your husband is allowed to undress you tonight. Kathy
presented her, the “Groom", with a strap on (& lube) to consummate our
wedding during the second week of our honeymoon.

We snuck back to the hotels honeymoon suite that night. My husband in
his suit and tie and I wearing our wedding dress. The second week was
amazing. We were married 9 years before I lost her.

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Keri
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Masters in Computer Science & Dance (activity), Carnegie Mellon University
·
9mo
My mom put me in ballet when I was 9 because she decided it would stop
me from being a bully and getting in trouble. Before my first class she
told me I would be the only boy and that there was a uniform for the
classes which I would have to wear. Then she handed me a pair of pink
panties because she said boxers wouldn’t work under the pink tights I
would be wearing. There was also a baby blue leotard. That’s how it all
began for me.
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John Smithe
·
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Ready to go both ways.
·
Apr 1
Mine was with my first mistress. I had decided one day to tell her I was
into wearing panties, and then brace myself for the fallout of that
reveal, I thought we would break up, but much to my surprise she was
really into it and encouraged me to take it as far as I wanted. She
picked out panties for me to wear, also put makeup on me, and had me
dress in some of her other clothing. It truly was the greatest of times
with her. After some of our sessions, I would be in tears of joy and
thankfulness.
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Stephen Walton
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Cheese is my guilt pleasure1y
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What was your first encounter with a crossdresser? Was it a positive or
negative experience?
Seeing a cock in nice knickers is one of my biggest turn ons. I wear
them myself and they are more comfortable than men's. My first sexual
experience with another chap was a cross dresser. I had been curious
about oral for a long time. We started chatting through a crossdressing
website and we got on really well. He was, like myself married. The
chatting finally came round to meeting. I packed some clothes into a bag
and went to his house. The door was opened by a really nicely dressed cd
in a purple dress and stockings. He showed me a place to change and I
slipped into a skirt,top and knickers and holdups. I went to the bedroom
and sat by him. It felt really strange but exciting sitting next to
another crossdresser. We had a slow kiss and I remember Softly kissing
and stroking his stocking up his dress. My hand then found the lacy
knickers he was wearing. They were so soft and I was stroking his cock
feeling grow. I had been curious about giving oral for ages. I teased it
from the hiding place and was slowly wanking it. He asked if I was ready
to try sucking and OK. At this point I was hard myself with my heart
racing. I slipped my lips and mouth over and started to suck and work my
tongue around the head. My mouth was soon bobbing up and down and I was
enjoying it. He warned me that he was about to cum. I thought better now
than later. I held the head in my mouth. I felt a drop of precum he
groaned and a pulsing spasm of warm cum filled my mouth and I just
started swallowing. It was electric! I sucked his cock a few times after
that, each time enjoying a mouthful of creamy sperm.

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Jane
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I’ve crossdressed for over ten years.!Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)1y
Related
Did crossdressing ever lead you to any gay acts or vice versa?
Gay acts….yesss but I’m straight and not attracted to men yet for me I
still wouldn’t call it gay acts l call it straight acts..

I’ll explain….. Oh b4 I do here’s a pic to help with the explanation k…..!!

So I started putting pics online because looking at myself turned me I I
couldn’t believe how feminine my body looked dressed up. Being straight
is why I feel that way lookin at myself which is still the reason I do
it now.. Having said that because of the photos I put online I got hit
on by men constantly like in DM’s it’s was like nothing I’d experienced
b4 like I couldn’t keep up tbh thick and fast and I realised how much
that made me more “female” so when I’m dressed up I walk, and move like
a female and yes I always sit to pee and wipe of course lol. Now I’m
completely do everything the way a female does including the way they
would masterbait which led me to thinking what a real cock would be like
plus being able to lie there an just cop it..🤔🤭 so eventually I found
out and it was great and from there I’ve progressed to getting paid for
it and like I said it’s straight sex to me still and I’m completely
straight whilst doing all of it because when its happening I’m always
fully dressed up the whole 9 yards makeup expensive wig etc. and I look
female he looks male so it’s just a male and a female having sex and in
the exact same way Im treated like a female I act like and do the exact
role any actual girl does in straight sex acts.. For the guy he’s no
different than any straight guy infact 90% of guys that I’ve fucked or
even spoken to say they are completely straight and most of them are
even married men…!! Which in my mind it straight acts..😘😘

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Chris
·
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X-dresser since young. Finally happy as my true fem self
·
Aug 18
Originally Answered: What is the most special moment on your
cross-dressing journey?
When I finally accepted that this is a part of me no matter what. No
more trying to keep it a secret from my wife. No more telling myself
that this is all wrong. No more self loathing as to why I liked women’s
clothes. No more lying to myself that I should be something or someone
else. Once I realised all of this, life became that much more enjoyable
and happy for me.
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Keri
·
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IT Programmer
·
Jul 28
Originally Answered: What is the most special moment on your
cross-dressing journey?
When I was 14 I auditioned for the corp in a professional production of
The Nutcracker. The director knew I was a boy but that I danced as a
girl. She picked me and 15 other girls to be in the corp. I was so
excited and the performances were great. The corp wore white tutus for
the first act and pink for the second act. I have danced in many
performances since then but that was the first one and it was truly special.
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Laura L
·
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Just a person exploring life and all its options.
·
Mar 20
Originally Answered: What is your favorite experience you had while
crossdressing?
My favorite experience was when I was completely made up from head to
toe and feeling/looking so sexy. That night I went to a club with my ex
and friends, I was so nervous but they all told me how great I looked
and they were there for me. When we got there, and after a few drinks to
loosen up, I became the center of attention, an object desired by her,
our friends, and some “strangers” that later became friends of sort.
That was a feeling I never experienced before and I was immediately
addicted.
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Barry Jones
·
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Lives in London (2001–present)
·
Jun 6
Having sex with another guy.
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Joanne Watters
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Former Dancer (1991–1992)Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsFeb 28
Related
When was the first time you cross-dressed and looked for a man?
This was not the first time I crossed dressed but it was the first time
I went after a man. It was Halloween & I got dressed up as a girl, my
mother helped me, doing my hair, nails & makeup. About two weeks ago,
while I was hitch hiking home, I was picked up by a guy who told me he
was bi sexual, I then told him about how I loved dressing up as a girl,
he told me that he hung out at a local mall. I & my friends also hung
out at that mall & I made it a point to find him & say hi on two
different occasions. When my mom finished with my hair, I got a purse &
a coat & went out, telling my mother I had a party to go to. I headed
straight to the mall to find my bi sexual friend, I wanted him to make
me a complete woman tonight. When I found him & told him what I wanted,
he didn’t believe me, he said I had to prove to him that I really wanted
to be a girl, I told him I would do anything because I wanted to live
full time as a girl. He took my hand into his & walked me to the salon
that was in the mall, he said he was buying me some acrylic nails, I
leaned over & kissed him before entering the salon. From there he took
me to the piercing pagoda where I had both of my ears double pierced. He
then took me to his place & made love to me.

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Dennisa Waggoner
·
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Former Firefighter/Tenical Rescue
·
Jun 14
Going to a big city late at night, finding a stranger , any male or
group of men that let me fill there sexual pleasure is the best. Never
knowing there names and probably never seeing that cock again, always a
new stranger.
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Jola Lavelle
·
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crossdresser sexUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020) and
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsUpdated 9mo
Related
Did crossdressing ever lead you to any gay acts or vice versa?
For years I thought I was only interested in dressing up. Then I started
posting pics online and hanging out in chat rooms with other CDs. I
would get lots of sexy comments from guys and they would flirt a lot and
pay me so much attention. Over time I became comfortable with flirting
with men online - I liked the way it made me feel. I began to wonder
what meeting a man while dressed up would be like - just to talk - no
sex. One evening, my wife was away and I was fully dolled up - make-up,
wig, lashes, nails, lingerie, stockings, dress and of course heels.

I was chatting online to various random guys and I just thought it might
be fun to drive to someone’s house dressed as a girl. It didnt take long
to find a willing host. I arrived and confidently walked in (as best I
could in my 5 inch heels). Because i was dressed up as Jola, I was
acting ultra femme - so I gave him a peck on the cheek. Immediately he
put his hands around my waist and kissed me on the lips… his tongue
entered my mouth and I didn’t stop him.

I french kissed him for a full minute - his hands were caressing my body
through my skirt. His hands on my ass felt so good. He suggested going
upstairs and for a second I thought maybe I shouldn't as I knew where
this was going, but I felt so girly I just wanted to please him. He had
a mirror in his room in which I watched myself as a girl as he touched
and caressed me. It was so sexy. I am not in any way attracted to guys
in my normal life. But when Im dressed as Jola I seem to take on the
personality and desires of a girl.

update:

A lot of readers have been asking me whether it went further. I can say
that on that day I ended up in his bed giving him a hand job, and
allowed him to finger me. In the subsequent months I completed my
journey as a sissy having oral and anal sex with different men.

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Samantha
·
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Just here.
·
Mar 19
My best experience what a nice and simple one. A friend of mine, a
woman, told me that she would love to take photos of me posing on an
outfit. It was my first time being infront of someone like that and I
was nervous. As we were going however all she kept giving me was
complements. I didn't mean for it to happen but I did begin to get an
erection and didn't even notice until she pointed it out, I was
embarrassed but that made me realize how amazing it made me feel to be
told I look sexy and desirable!
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Cdmelanie
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Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 yearsJun 29
Related
Has anyone introduced you to crossdressing? How was the experience? Did
you enjoy or hate it?
I wasnt introduced into crossdressing but when my ex wife told me she
was divorcing me because I was a failure as a man and then suggested I
become a woman because I never was a real man nor would I ever be one.
to further humilate and emasculate me she also said she was leaving all
her lingerie behind because it would fit me better and I could see for
myself she was right that I'd be a better looking woman.

I admit hearing what she said about me after 22 years of marriage was a
hard pill to swallow. then one day while putting away my laundry I
looked at the lingerie and thought what have I got to lose. what if my
ex is right, so I tried on a teddy with matching thigh high hose and
panties. I must say I was quite shocked when I looked in the mirror and
realized my ex was absolutely correct. I stayed in that outfit the rest
of the day as I went about doing chores around the house and even slept
in that outfit.

I got up the next morning feeling refreshed and excited, I decided I
wanted to explore this new life as a woman. I showered and put on a
clean pair of panties from another lingerie outfit and went on a
shopping spree. I bought several.outfits, panties, bras, and thigh high
hose,make up, jewelry, shoes, wigs, lady razors,feminine body washes and
lotions and perfume. I rushed home and began my journey into becoming
the best woman I could be.

the transformation was a complete success and I said a final good bye to
my beta male life and everyday I thank my ex wife for opening up my eyes
and heart to be the person I am now.

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MariaKim
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Mar 10

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Laura L
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Just a person exploring life and all its options.Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years9mo
Related
Have crossdressers ever been gangbanged while cross-dressed?
Yes. My ex wife and I hosted a Halloween party and she demanded to pick
out my costume. She decided I should be a French Maid, and wanted to see
how feminine she could make me look. So, all of my body got waxed (ouch)
or shaved. Then makeup, blonde wig, nails, stockings, and very tall high
heels (that she made me practice walking in.) As I looked in the mirror
I couldn’t believe how sexy I looked! We proceeded to do some shots as
she teased me, making me hard and then letting me cool off. When the
guests started arriving there were quite a few men I had never seen
before, but we both loved ménage a trio’s before and she wanted to try
more than 2. So I write it off as that. As the night went on the guys
started taking pictures with me, groping and in various positions. I was
drunk, my wife was egging me on, and I loved the attention. The next
thing I know is there are 2 guys with their hard cocks out and my wife
is begging me to suck them. So, I did as she took photos. It wasn’t the
first time but these were large hard docks and I was extremely horrny. I
really got into it gagging myself on their cocks until the one said he
was going to cum. My wife told me to be a good host and swallow it all,
that was all it took and he unloaded in my mouth. I then started going
to town on the other guy and didn’t notice additional men coming into
the room. Suddenly I was surrounded by guys striking their hit cocks and
“ waiting for their turn.” I remember sucking off 4 cocks and swallowing
all of their cum. Then things got fuzzy, but my wife was still running
the show and telling guys what to do to me as she took photos. The last
thing I remember was my mini skirt being lifted up and a hard dick
pressing against my ass, while another guy was holding my head so I
could suck him. When I woke up I was covered in cum, my stocking, wig,
face, and it was leaking it out of my ass. I felt like I had to use the
restroom, but was very sore as I went to the bathroom. It was nothing
but loads of cum, and the mixture of pain, foggy memories, and cum
covering me made my cock get hard. I started jacking off and my wife
came in… she said “that’s a good lil bitch stoke that cock for me” and
started showing me photos of what a whore I was!! I started cumming
looking at how I was used as a whore and the amount of men surrounding
me, she dropped to her knees and sucked my cock, but only so she could
kiss me and shove her cum covered tongue in my mouth. She stepped back
and said now you know how you taste as well as all her friends, and
explained she had set it all up to watch me come out and become the
sissy whore she wanted me to be.

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Tony Coxx
·
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Crossdresser, Retired Barber, Beautician at Shop Owner (1968–present)Mar 26
Related
What are some cross-dressing confessions?
I could confess a few things but this is somethinhg I never told anybody.

When I was 18yo, I was in the mall on a Saturday afternoon while
crossdressed when I ran into my mother's ex-boyfriend. He knew I was Bi
crossdresser from when he dated my mother. After talking for a few
minutes, he said his daughter, who was away at college, had cleaned out
her closet and left a couple bags of clothing for him to donate. He
asked me if I wanted to look at the clothes before he got rid of them,
and I could have anything I wanted. I said yes, because I knew she had
nice clothing and getting some free outfits sounded good. He smiled and
took my hand and we left the mall holding hands. He walked me to my car
and I followed him to his house.

We went to her bedroom and as I was looking at the clothes, he said I
could try on anything I wanted. He sat on the bed and watched me as I
tried on several dresses, skirts and tops. It felt strange continually
stripping down to my panties, bra and stockings and dressing in front of
him but the clothes were nice and I wanted to take them. He said I
looked cute in my high heels, bra and panties which also made me a
little uncomfortable. I got done and I packed up everything I wanted
into a couple bags and before I put my dress back on, he walked over to
me, put his hands on my waist, and said if I wanted the clothes, I had
to have sex with him. I was nervous at first and just stood there for a
minute saying nothing and my mind was racing. He was a handsome guy in
his mid 40s and I always liked him but it seemed strange to have sex
with a guy my mother had sex with first. I really wanted the clothing so
I said okay but I made him promise me he would never tell my mother. He
said okay.

He dropped his pants, sat on the edge of the bed, told me to get on my
knees and suck his dick to begin with. I went down on him and sucked him
until he came in my mouth and I swallowed his load. I thought I was done
but he told me to lay back on the bed until he was hard again because he
wanted to fuck my ass. He laid next to me and we talked for a little
while, he kissed me and had his tongue in my mouth and I kept stroking
him so he would get hard again.

When he was good and hard again, he pulled off my panties, lifted my
legs and slid his dick in my ass. It felt so good and he smiled as he
began pumping my butt slowly. His hands were all over me as he picked up
the pace as he went deeper in my ass. By now he was feeling great and I
was really excited as he squeezed my ass and my nipples and kissed me.

He fucked me hard until he came in my butt. He stayed in me until he
went limp and then he kissed my butt cheeks when he pulled out. He laid
back down next to me, kissed me, and said he liked fucking me. I said he
had a nice dick that felt so good in my mouth and ass and I was glad I
let him do me and he was happy. We laid there for a while talking,
touching and making out. He made me feel very good and knew just what to
do to drive me crazy.

When I finally got up, I got cleaned up, got dressed, grabbed the bags
and got ready to leave. He said he wanted me to come back the following
week and do it all again but I said no. He then kissed me with tongue,
rubbed my dick and said if I came back, he would suck me off too so I
said maybe, I'll think about it. I thought about it all week and decided
to go back to his place the next Saturday. He was happy to see me and
gave me a nice gold necklace. He said he knew I'd be back and wanted to
give me something nice. He put it on me and we headed for the bedroom.

It was a total repeat of the first time but I got more into it the
second time around because I knew what he liked. He didn't suck me like
he said he would but that's okay, I still had fun with him. He was 27
years older than me, he had a few gray hairs but he had a great body and
he was great in bed.

He wanted to make it a regular thing but I said I had to think about it
because it still felt strange being with a guy who had sex with my
mother. He told me to come over in the morning and we could go out as a
couple and spend the day together like a date instead of just meeting up
for sex. I said I'd like that.

That's what we did, he treated me like a woman all day long, treated me
like a sex doll at night and it made me want to continue seeing him. I
kept seeing him for several months until his daughter came home from
college for the summer but he was really great while it lasted.

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Lisa Lust
·
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Former Crossdresser May 1
Some of my best experience have been going to a sex club and having sex
with multiple men and other cross-dressers throughout the nights. Those
places are fun because everyone is open, there are rooms with beds on it
with people fucking everybody watching you people getting in line ready
to fuck you or get sucked off, Sections where they would have multiple
glory holes so you would just stick your cock through the hole and you
would get sucked off. I would be in the booth just waiting for the cocks
to come through and to suck them off. In between fucking and sucking, I
would just visit the rooms and just watch the excitement of men fucking
these cross dressers , and then me getting turned on and joining the
fun, I really miss those days and were really fun when I used to attend
and participate hopefully one day I get to join those parties again.

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Larry A Nelson
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Former Freelance Adventurer and BloggerUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)4y
Originally Answered: What has been your best cross-dressing experience?
The first time that I went to a women’s clothing store and tried on a
dress. I was underdressed wearing panties, a bra, a camisole and a half
slip. I went to the store, a Dress Barn, shortly after they opened on a
quiet Tuesday morning thinking there would not be many other shoppers in
the store. I had already searched omline and had picked out a dress that
I was interested in. When I got to the store, I was greeted and asked if
I needed help finding anything. I told the sales associate what I was
looking for and she asked me what size. I told her that I was not sure
but from the size charts, either a 16 or an 18. She pulled down both
sizes and I asked shyly if I could try them on. She lit up with a big
smile and said “Of course!”. She ushered me to a changing room and put
my name on the door.After a few minutes she came back to check on me to
see if either dress fit and she wanted to know if I wanted to try on
anything else. Well, the size 16 fit best and it felt so good over my
female underwear. I was too nervous but happy to try on anything else.
So as I was checking out, I asked if they had many male shoppers and she
said yes, that I would be surprised how many they had. Too bad Dress
Barn is closing, it was a wonderful,day and I have every intention of
going back.

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Lisa B.'s Space ·
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Answered by
Lisa B.

Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
Oct 15, 2022
I was 19, first time really having sex with a man. First time dressed in
front of someone one on one. He was in his late 30’s. I only had him
inside me for about a minute and I had my first sissygasm.

… (more)
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Delia Smith
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Lives in Hertfordshire, U.K. (2017–present)
·
Jun 13
I was seeing a guy on a regular basis. I loved getting dressed up for
him and enjoyed how he would take control. He eventually talked me in to
meeting up with him and a friend of his. I was incredibly nervous at
first but pleasing two guys at the same time was such a turn on. The
three of us met up many many times after that evening.
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Joanne Watters
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I wore waterproof mascara without knowing it & got caughtUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)2y
My best experience was after I told my boy friend that I would like to
be with two men at once. Two weeks later, he told me we were going to
get a motel room for the weekend & that I should get dressed extra sexy.

I wore a white, tight, low cut sweater, a black, belted mini skirt,
white, shiny pantyhose & black, open toed, four inch heels. I wore my
hair up in a bun & had long, white, dangle earrings hanging from my
ears. When we got into our room, we started making out, soon I was on my
hands & knees on the bed as my boyfriend entered me. He had just got
into me all of the way when the door was flung open & a guy walked in,
climbed onto the bed, pulled out his cock & stuck into my mouth. I was
in heaven, there is no better feeling then having two cocks in you at
once. When we were done with round one, my boyfriend told me he set this
all up. God I love him.

I love being a feminine sissy

22.8K views
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Ms. Tasha Stokes
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Jul 27
I met a army friend while stationed in Germany we were talking one day
when she asked me do have any heels clothes hair make up and all the
good stuff telling me she me she knows she goes into the closet comes
out hold a pair of brown 6–7 inch Wedge peep toe heels and says I saw
saw these on your computer a while ago I wanted to ask you this question
for a while “when are we going out” idk I'm having a hard time with
myself and my desires. She says you have all those cute ass shoe you
need to wear and do it right we can do it together. She picks the wedges
back up and say your highest heel would be a wedge lets t

274 views
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Paula Ray
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Truck Driver (1993–present)Apr 21
I would say the best experience was when I was married to my ex-wife.
She worked with a gay man who was a bit older than me. Since I was
disability from car accident and I was dressing as Paula full time and I
had already had all my body hair completely removed permanently and
facial hair also expect my eyebrows and eyelashes and long hair on my head.

She was working a night shift alone with an called me to bring her
something I said that I was dressed as Paula she said that it was ok
only Dan was there. I said ok I was dressed very sexy in red mini dress
thigh high stockings and g-string and my high heels. Well I went and got
full set of square tip gel nails done and painted and toes painted and
eyebrows done thin and arched feminine earlier that day.

Well I went to her work well I got there I was talking to her when he
came up and asked who was the beautiful sexy lady she was talking to.
She said oh and told him who I was. He was very surprised about how open
about it she was. He said that she must have to beat guys away from me.
She surprised me when she said that I was very bisexual and liked men.
He said that doesn't bother you to her. She said no because she likes
being with other men too.

We all talked for a few minutes and she even told him that I was a total
bottom completely. When he said that it sounded like she was trying to
hook us up. She said that was between him and I. She left for a few
minutes and he and I talked he asked me if I wanted to go a drink when
he got off I said yes.

Well that turned out to be what become a wonderful romantic relationship

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Judy
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Jun 3
I have had many great experiences over time. I just had a really great
one. My young neighbor, she just turned 39. She’s been going through
some rough times. We would talk about them. I’m 20 years older than her.
I’m a good listener. Her talking about them really helped. She trusted
me so much. She then told me some very deep secrets about herself. Once
she told me I knew she kind of wish she didn’t. I told her, her secrets
were safe with me. There are. A few days later she was still worried
what she told me. I told her I had secret that no one knows about me
(except my sister). I have always wanted to tell her this but was
afraid. She asks what it was. I really didn’t know if I would tell her.
She kind of gave me this look. I trusted you with my secrets, so you can
trust me with yours. I’ve known her for years and always wanted to tell
her. I been wearing women’s t-shirts and shorts for years around her.
Also, other women’s clothes. there are neutral looking. I’m always
wearing Bras and panties under them. I’ve always wondered why she never
felt the bra under my t-shirt when we have hugged over the years. I knew
then that I was going to tell her that I was a crossdresser. So I told
her that I like to wear women’s clothes and at time I would get all
dressed up. Makeup, wigs, dresses, the whole works. She kind of looked
at me. It was a really big secret that I told her. She still gave me
this look if it was true or not. Before she knew it I lifted the t-shirt
and showed her I was wearing a Bra. I never showed anybody before me
wearing a bra. She gave me this look that I wasn’t sure what was going
to happen nexted. She then. got this smile on her face. She said I knew
there was something different about you, you always been very nice, and
I felt safe around you. She then told me we both have secrets to keep.
We talked for a while, and she wanted to see me fully dressed up. we
decide that later tonight I would get all dressed up and she could see
me. She said what time would you like me to come over. I spoke and said
what I would really like to do is get dressed up and come over to her
house. She said sure. Later that night, I was so trilled I walked over
to her house. I was in full girlie mode. She answered the door and took
a look at me. She asks me in and said I look nice. I know I don’t pass
like when I was young. It didn’t matter to her or me. We talked and had
a great time. We talked about my crossdressing and what we normally talk
about. for me I was such a good time hanging out with someone while I
was all dressed up. The nice thing was it wasn’t sexual at all, just two
people enjoying the company of each other. It was one the best
experience I have ever had. As far as I know we both have kept are
secrets. We are good friends, and we do stuff together. go dinner and to
the movies so I don't have to go by myself

777 views
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Jamie Jones
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Bricklaying Teacher start Monday (1993–present)
·
2y
My best crossdressing experience happens every time i cross my door step
fully crossdressed, This is every weekend away from work, I count the
days down till every Friday night, then I prepare what im going to wear
on the Saturday to go out and about shopping or to any other places i
need to go, I always come back feeling happier and feeling a lot more
freer in myself.
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Julie
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Telephone Operator (2022–present)
·
May 27
It was one of the simplest thing that can happen I was invited to lunch
by 2 women I know. We went to this nice restaurant, sat in booth in the
corner. And was all female conversation. We talked about clothes,
makeup, feminine products, where to get your hair and nails done.
Checking out the men eating who was who was not. It was great time to
woman and we now meet on a regular basis.
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FutaPrimitive
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Cam Slut at Self (General Contractor) (2022–present)Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
1y
My wife helping me dress up and take pictures for fansly. Like just
being able to be in the room with her talking about every day stuff
while getting ready and doing makeup was such a beautiful experience.
Then her acting as my photographer for all of it telling me what works
and what doesn't. We are truly comfortable with each other and I am
forever thankful for what we have.
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Rikki Verdada
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Self- Employed Industrial Femme Handyperson at RVT Construction
(1974–present)
·
May 23
When I began to ‘come out’ to family members and friends about my need
to cross-dress and why I do so and subsequently, my sexuality
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Dannielle Freya
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Lives in Seattle, WA (1951–present)
·
Jun 18
Lots of them, tremendous blowjobs, being fucked gently with passion.
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Julia1998
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ROANYER Brand AmbassadorUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
1y
As I was walking confidently down the street in my women's clothing, a
stranger approached me, smiled and struck up a conversation. He
expressed his appreciation for my appearance and invited me to have
dinner. Although there was some hesitation in my mind, I decided to give
him a chance. We spent a pleasant evening, exchanging our interests and
dreams. That night, I found him to be very sincere and kind to me.

… (more)
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Anonymous
4y
Originally Answered: What has been your best cross-dressing experience?
I was 22 and trying to transition. I had taken estrogen and hormones and
my breast began to grow. Soon I was a 36DD. And in time I accepted. I
love having bigger tits. They felt great and they were very sensitive to
the touch. Well here it goes. I looked young and out of the blue one day
a young man ask me to the prom not knowing I was still a man with
incredible puppies. I should of said no. But I always wanted to go to a
formal in a beautiful gown. He picked me up. Gave me my corsage and I
was dressed to impress. We went to meet his parents and take pictures.
Not a clue they had. I was not slutty just a beautiful young woman. My
breast were struggling to stay inside my bra and dress. No one knew at
prom. Boys loved me and the girls hated me. I was hit on so many levels
there. The men faculty was all over me trying to flirt. I was flattered.
But I was true to my date. Typical young man. A gentleman all the way.
We had a great time dancing laughing etc. I excuse myself a couple of
times to powder my nose. I needed a cigarette bad. So I snuck out a side
door and enjoyed it. I was wondering what I was doing at prom . It was
fun though !! Prom finally was over and we heading back to my house.
Again a gentleman, he open my car door and made sure my gown was inside.
Then impulsively he leaned over and kissed me. I was shocked and decided
why not so I kissed him back. Up till now I had no experience with
boys-men. He slid his tounge in my mouth. We must of kissed for 10 min.
I said we better get going. I knew I could not proceed with him any
further!!. I wanted to though. I was WET- hard. He took me home and we
kissed for awhile. We said our goodnights and parted. I felt like
Cinderella. I went in and stayed in my fem attire all night.

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Maria's Crossdressing ·
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Answered by
Samantha Jamesons
Aug 12, 2021
Would have to say the first time my wife took me shopping. Went into the
ladies store. Selected some outfits for me. Then proceeded to have me
try them on. That’s when it got exciting. She made me walk out of the
dressing booth where she wanted for me to show her the dress I was
wearing. However not only was she there but two of the sales ladies
where there waiting as well. All cheered me on and then the sales ladies
started bringing me outfit after outfit to try on. As I started trying
on everything and was showing them off other female customers where
looking as well. After 2 hours trying on which I think was everything in
the store I ended up with two new dresses a skirt n top. Was one of my
best days shared with my wife while crossdressing. Since then we do the
shared shopping trip on occasion.

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Sonia
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CrossdresserUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)1y
My best crossdressing experience was when I had the opportunity whilst
my Wife was away to transform myself into a woman.

I started with having a bath to get my skin nice and soft had a really
close shave ,applied loads of moisturizer all over my body then I
slipped on a pair of panties and a sheer kimono and spent the best part
of the next hour doing my makeup and I was happy with the result that
some makeup, false eyelashes, lipstick and a wig gave me a more female
look. Then it was my lingerie a nice lacy bra with breast inserts a six
strap suspender belt and some lovely panties, then it was time to enjoy
slipping my feet into a pair of gio stockings and the wonderful feeling
as I unrolled them up my legs and attached then to the suspenders after
some little adjustments it was time to put on my lovely knee length
dress and 3 inch heel court shoes. Now I was all dressed my heart was
racing as I tried to pick up the courage to leave the house and go to
the car without the neighbours seeing me. I then drove to a near by town
which is known to be reasonably quiet, parked the car and I was about to
experience my first and I still look at at as my best crossdressing
experience as I went for a stroll through the lovely gardens of this
lovely place spending sometime sitting on a bench enjoying the wildlife
in the pond as I contemplated on my first public outing as a
crossdresser of which I look back on with fond memories. It was made all
the more memorable as I had encountered a few members of the public and
was always greeted politely and with a smile. I have had other
experiences since then but my first time out fully dressed was certainly
the most momentous and enjoyable for me. Then it was home stopping at a
convenience store for a bottle of wine then it was time to slip into my
sheer pink baby doll and kimono and enjoy some wine before it was time
for some beauty sleep.

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Some Amused Guy
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Acerbic Thoughts Honed Over 61 Years.Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)11mo
Mine would be boring to most.

I was picking out some jeans, and a woman who worked there came up and
asked if I needed help. I said I needed a pair of 28s in a particular
wash. She pulled them and said, “If these don’t fit her, you can bring
them back, no issue.” I looked and said they were for me. She never
batted an eye and asked if I’d like to try them on, so I did, and she
wanted to see them on me. I came out, and she gushed at how well they
fit. To my surprise, she said. “I’ll be right back.” I was a little worried…

She showed up with a couple of tops and said, “I think these will look
awesome with those jeans and your build.” They were double cotton, long
sleeves, and looked like they had been fitted to me. I’d never put on a
shirt that felt like that outside of some custom-made dress shirts, but
the fabric - holy crap. I bought them both, and the jeans.

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Stephanie Cain
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AS in Medicine and Healthcare & School of Common Sense, Crafton Hills
Community CollegeUpdated 4y
Originally Answered: What has been your best cross-dressing experience?
Renewing my wedding vows wearing my wife's wedding dress.

My girlfriend knew I was a crossdresser before we married. That's a
story all in itself. We married on a Saturday. I wore a tuxedo and she
wore a beautiful white dress. Her best friend Kathy and her husband,
Richard, also knew that I crossdressed. During the first week of our
honeymoon, Kathy altered the wedding dress so it would fit me. On Friday
afternoon, we snuck back to town and spent the night with Kathy and
Richard. Saturday afternoon Richard gave me some beautiful white bridal
lingerie and then dressed me in “our” wedding dress while Kathy got my
wife dressed in a tuxedo. Saturday evening my wife and I renewed our
wedding vows in a very private, very special ceremony. I wore our
beautiful white wedding dress. Richard, who also crossdresses, was the
maiden-of-honor and wore a beautiful evening gown. Kathy was my wife's
best man and also wore a tuxedo.

Kathy and Richard witnessed me becoming my wife's wife and she become my
husband. We had 9 wonderful years of marriage before I lost her.

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Asteria
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Lives in Setagaya-ku, Tokyo, Japan (2024–present)Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)1y
a sobriety checkpoint where the officer complimented me and said have a
nice evening Ma’am

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Cdut
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Lived in Utah (2024–2024)
·
May 27
i was hiking on y favorite nature trail in my favorite daisy duke
shorts, an older man, sitting on a bench said to me as i was walking by,
“no that’s a spanking ass”.

i told him, “don’t let me stop you” and he seated me a good one. it
excited e so much, i talked him into letting me give him a lap dance, it
was wonderful to feel him drain hi’s balls in his shorts.
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PC CrossDresser
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Lives in Southern Arizona (2015–present)
·
Mar 11
While i was living in NC and the wife was at work, i would dress up
completely and put sweats over it, then walk to the woods edge and take
off the sweats and leave them. i would walk several miles into the woods
enjoying the cool air. on the return trip i would strip to only Panty’s,
bra, stockings, and garter and walk back.

Now adays, i dress up and go for a drive around town.
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Anonymous
Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)4y
Originally Answered: What has been your best cross-dressing experience?
I live on Oahu Hawaii and I’m married cross dresser in a sexless
marriage of 30 plus years.
ive has a boyfriend for two years.

My birthday was coming up and I went to Savers for buy a new dress. The
sales asst’ asked if she could help me. I told her straight out the
dress was for me. And she picked out a sexy spandex dress. She had me
try it on and model it for me. When I stepped out. I felt so sexy. And
she said she wanted a picture of me all dressed.

On my birthday I got a text from him that he would meet me after 6. I
was all made up, dressed up and knew I was a sex kitten.

When he seen me. The bulge in his pants grew before I could rub his
pants, in no time I was in his arms as he made me feel like a real woman
the way he kissed me. Soft, deep and long.

In no time I was on my knees as he fed me his tool as I worked him up
hard for the first five minutes. I couldn’t get enough. He kept telling
me how beautiful I looked.

Then he sat me in my truck and rubbed his face over my panties and he
ran his tongue over me again and again. Taking the top of my panties
down slowly he took me into his mouth and whispered “Happy birthday” as
he sucked me slowly while working his fingers inside me.

In no time I was moaning and danced on his fingers. My head was spinning
with pleasure and before I knew it he pulled my panties off and KY was
inserted.

I took a quick look around to see if we attracted any on lookers. I had
been kind of vocal.
but nothing compared as to when he ran his hands over my spandex covered
body as he inserted his 5 inch cock which is the thickest monster I’ve
ever seen.

It took my breath away as he worked us into a heavy rhythm. I found my
self pleading for him to pound me hard, which he did, hard and deep and
had me moaning loudly.

He made love to me for ten straight minutes which he usually only lasted
a couple of minutes. I opened my eyes as he kissed me and seen he was
completely naked and announced he was about cum.

Sweat flowed down his hard body as he slammed into me as deep as he
could and circled his hips, then it happened. I came hard without him
touching me ! I came hard as my ass tightened on him and he shot his cum
into me. The most wonderful feeling in the world.

His lips were like sugar as he kissed me again for what felt like
forever. Then got dressed. Got on his motorcycle and left me.

For all my life I wanted to know what it felt like to be a woman. And
that night. He treated me like “His woman”. It was the best night of my
life as a cross dresser.

I reached up on the dash board and turned of the recorder and played
back the whole thing.
it still is the most sexy fuck session I’ve ever heard.
my whimpers and moans mixed with his grunts and then us cumming at the
same time. Oh My God I really can’t wait until I got to work tomorrow.
It may have been a year since that night, but we’ve made memories since
then.
however. I just can’t wait to see him again tomorrow night.

I’ve bought a new dresses, makeup and wigs. I’m going to drain him dry !

27.7K views
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Anonymous
5y
Originally Answered: What has been your best cross-dressing experience?
Some years ago, summer was hotter than usual where I live. My wife, a
friend of ours and I was out shopping when my wife saw a mini skirt that
she really liked. I looked at it and said to my wife that I would like
to buy one for myself. So a few days later, I went to the store and
bought the skirt in my size.

After being out for a walk a few days later, we got home and was very
sweaty because of the heat. I then changed into a bra with padding
giving me a B-cup, female panties, a top and put that skirt on.

It filled me with a delight I had not experienced before. It cooled me
down more than any male garment I owed and at the same time gave me a
sexual arousement. I said to my wife something in the line of “I think
that I have come home wearing this” meaning that I felt like this is who
I really was. My wife just smiled at me in acceptance.

I had of course cross-dressed before, but the feeling I got wearing this
outfit was way beyond compare with regards to both bodily and sexual
wellness.

And every time I now wear that skirt it reminds me of how wonderful the
experience was.

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Russell Duncan
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May 16
I met two young black guys at a bar. They were showing alot of interest.
I was dressed very sexy. I had on a short skirt with gartebelt nylons
and heels. I went to there apartment and had sex with them. I sucked
both of them and they both fucked me. It was wonderful.
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Clay Sanderson
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I Am a Sex Worker for my man .Updated Apr 11
When I went to a adult theater I was dressed a little slutty and a black
guy was hitting on me it was the first time a black guy had done it.but
he came right over to me sat down next to me put his arm around me and
started with how hot I looked he ask me if I ever been with a black man
before I said no .then he just started kissing me at first I was trying
to get him off me but then I felt so good and scared at the same time so
I just put my arms around him and went with it every one in the theater
was watching us jacking there cocks and then we sat back up and he was
rubbing my legs and he pulls his cock out and ask me if I like it but
before I could say anything he said I Know you want it baby and he
pushed my head down on it hard and I started gagging and he said relax
bicth and it keeps getting bigger and bigger and he is still Force
feeding it to me then he tell me get ready to swollow my big load you
better not spit it out bicth and oh how he busted that nut in my mouth
then he tells me to lick him clean I did then he gets up off the love
seat and takes his pants off and tells me to lay on my back then he puts
my legs over his shoulders and he gave me the best fucking I have ever
had I was telling him to fuck me please don't stop fuck me and I was so
loud people that. We're in the peep booths came into the theater to see
what was going on that was the first time I had ever cum with out
touching my self he finally stopped and he told me not to go any where
he would be right back and as soon as he left the guys that were
watching came over and started trying to fuck me and shove cock down my
throat I told them that my man would be right back and they said whorehe
not coming back we going to fuck your sluty ass and I am trying to stop
them but there was just to many of them they had me down on the love
seat and one guy put his cock in my mouth told me I better suck it or he
would bicth slap me well he was slapping the shit out of me and my man
came in and he could see I was trying to stop them he grabbed that guy
that was slapping me and he ask him if he like bicth slapping the guy
said yes I do and the my new buddy bicth slap him all the way to the
door the other guy said they were sorry and then he asked me if I wanted
to go to a party with him I said yes he said we could go to his house
Andi could get cleaned up I told him I had more clothes in my car
because I always had to change when I came there from all the guys doing
me so I grabbed my over night bag and we went to his home where he fuck
me again when I came out of bathroom he goes baby girl you looking
hotter than hell. My goodness you is one hot bicth. You going to be my
new bicth for real .well he took me to the party and to some of his part
places and he would tell his friends that I was his new bicth and ever
sents that time I have loved black cock his name was Mike and I work for
him for a lone time .he was put in jail for drugs

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Marvin Shelphanger
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Former Soldier (1975–1995)
·
2y
First time I cross dressed to go out with my high school girlfriend and
she did me up. We went fearlessly to a 3 clubs! Never had any trouble in
or out of them. We had a fantastic time! But let’s be real, I didn’t
look passable but was presentable. Still had a super time that night!
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Jennifer
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Former Law Enforcement2y
My best was in my early 20’s when after having put together a nice black
dress and black lingerie with garter belt and seamed stockings, and 5
inch heels, black also.My new breastforms completed the look. I had done
a masterful makeup job and my wig was coiffed to perfection by a local
stylist I knew well. I checked the mirror and was happy with the
results. I grabbed my purse and headed to a local gay bar. It was packed
and I saw a few gurls I knew and chatted awhile. It wasn’t long and I
got and invite to dance from a handsome guy my age. We did a few fast
dances and when the slow dance came he asked me again and I figured why
not, I was enjoying his company. While dancing his hands roamed from my
back to my butt and he was fondling my ass cheeks and grinding his hard
cock into me. This turned me on, knowing I could get a rise from a man
this easy. With both of us hard now, he asked if I wanted to go out to
his car. I said OK and off we went. Before I entered his car, I told him
, you know I am a guy , right. He said he did but I was better looking
and hotter then any girl he had ever been with before. That was all I
needed to hear, so I got in his car and we started making out. His hands
were all over me , so I managed to slide my hand to his groin and
started groping his hard cock. He asked if I wanted it and I said I sure
did. He pulled off his pants and undies and we climbed in the back
seat.I grabbed his manhood and began jerking him off. He moaned and I
went down on his cock, licking the head and the shaft before taking all
of him in my mouth and doing the head bob. He lasted 5 minutes and shot
his load down my throat, me not missing a drop. We sat back, and I said,
what about me? He said he wasn’t gay just loved crossdressers. I asked
if he would fuck me and he said he would as soon as he got hard again.
That was all I needed to hear, and went back down on him and got him
hard . I slipped off my panties and lubed his cock and my pussy, and
proceeded to mount him . We went slow at first until I was comfortable
with his entry into me , then I rode him hard until he blew inside me.
He told me I was a great fuck, and I now knew I had entered a point in
my life where I truly belonged. I was put on earth to please men and I
have ever since. This young man and I had many encounters over the next
few years until he moved away.That was my best experience, knowing I
could please a man.

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Jay Chick
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Doctorate from Vanity Fair Panties and Lingerie (Graduated 1990)4y
Originally Answered: What has been your best cross-dressing experience?
There have been so many for me and my wife of 27 years.

Before we were married, we lived together for 6 years and we traveled a
lot. There was one road trip to Kansas City in the late 80’s where she
packed for us and I got home from work and we drove there. KC was a
frequent destinations for our road trips and had been there 6 times
together by now.
By this time in our relationship, I wore panties everyday and on cooler
days, I wore camisoles or short full slips or chemises under my thicker
shirts or under a sweater vest or something that to concealed my straps
and pantyhose or thigh highs under my slacks to work. So, on this day,
all I was wearing under my khakis and button down shirt and sweater vest
were my soft blue VF nylon bikini style panties, lace top thigh-hi hose
and my wide strap plain white nylon camisole and the matching short
half-slip.
So, I got home at 2pm after fueling the car and checking all the levels
of the car and picked up “Cindy” (not her real name) and we hit I-35
North. After eating at one of our favorite restaurants, we got to the
Embassy Suites in KC around 9:30 and after unloading the car and
unpacking our bags we took a nice jaccuzi bath together, and we shaved
each others legs and crotch areas. We got out, dried off and put lotion
on our skin then slipped into our matching satin gowns and robe, smoked
a joint and we painted each others toe nails. This made us horny so we
made love and went to sleep after a long day.
Cindy was up first to get ready and I lazied around in my gown and
matching robe, smoking a joint and having coffee when she came out of
the bathroom/shower area in her gown and matching robe and smiled and
joined me on the couch for a while, relaxing, smoking and drinking
coffee, our favorite morning activity. I started to get horny and was
stroking her tits in her satin robe watching harden but wouldn’t let me
go down on her since she didn’t want to shower again but she did opened
my robe, pulled my gown up and sucked me off and we shared a lovers kiss.
We had plans on going to a big flea market we have been to before and we
were deciding on what to wear and take with us and I told her to pick
out what we were wearing under our clothes while I shower. I hung my
gown and robe on the hook on the back of the door and when I got out of
the shower, Cindy had hung her gown and robe there also and put the
lingerie she wanted me to wear, me knowing she will be wearing the same;
Victoria’s Secret 2nd Skin Satin matching pink bra and hi cut panties,
white garter belt with beige stockings and a short white full slip with
lace around the bust and hem.
I got hard again thinking about our day while putting on my lingerie.
When I went to the room, Cindy was wearing her new dress she bought the
week before that I told her she looked so pretty in.

I questioned her about the lingerie I was wearing and she told me
because it will feel marvelously sensuous and look sexy under what I
bought you to wear. So, before you argue, I know you have wanted to do
this so now is your chance to be my girlfriend for the day. She took the
dress from the bed and pulled it over my head and down my body it went.
It fit perfect except for the extra material in front that should
accommodate breasts.

The hem of the dress fell a few inches from the bottom of my slip and
since I do not tuck, it hid my bulge just right. I told her that I loved
everything she has planned but I still looked like a man in a dress.
Cindy told me to give her a few minutes to work a bit of magic and then
then I can decide. As she worked on my face, she was telling me that we
are in a place where no one will know us or give us a second look. If
people looked at us, they will see 2 women that are into each other
having a great time laughing and enjoying life. This logic relaxed me
telling me not to look as she pulled a brunette wig that she had already
brushed out and fixed it on my head and when she finished my face and I
saw the subtle yet pleasing make over she gave me and I couldn’t say no
to her. Cindy inserted 2 foam breast forms in my bra cups to give me
some shape, clip on earrings, necklace, bracelet and a few rings.
I was speechless and she saw how nervous I was. She stood me up and we
looked at each other standing side by side in the mirror and she took me
in a gentle hug, running her hands over the dress, feeling all the
layers of the lingerie gliding over my body then she kissed me, told me
she loved me and wanted to do this for me and her. She can live out a
bit of lesbian tendency she has and she will not let anything bad happen
to me. It was getting on in the day and we were hungry so Cindy gave me
a spare purse for my stuff and a tube of lipstick and blush and to touch
up along the way. I put on a pair of beige 1″ heel, open toe sandals and
we grabbed our jean jackets and never looked back.

We looked like 2 girlfriends who were very much into each other and we
had a great, adventure filled day.

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Answer requested by
Jayma Jamieson
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Neil
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Practicing Law in a Skirt and Heels Since 2015
·
1y
The last time I answered a similar question, I said attending a friend’s
wedding in a dress. Now, though, I have to say attending my own wedding
dinner in a dress.
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Brenda Sopantyhose
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Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
1y
THE BEST I'VE HAD IS EVERY TIME I GET DRESSED UP IT NEVER GET OLD

and my girlfriend loves it… (more)
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Answered by
Coleen
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Aug 14, 2021
I have had many great experiences crossdressing. The first great
experience was when my mother caught me dressed with her friend. She
just told us to get ready to go out and I was to stay in my fem
clothing. We went shopping and bought lots of clothing for me from
lingerie to jackets and nightwear. I was to put them all in my mothers
bedroom in an empty wardrobe. She then asked if at night we shared the
same bed as girlfriends. That was just before I started a sexual
relationship with my mother.
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Donald Brigden
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Mar 22
This one time when my friends and me were going out to a party, I'd been
wearing my female friends clothes on and off for a while now (with her
knowledge), and I had worn a skirt out in public only once or twice, so
she invited one of our other friends over, and they gave me a dress, a
bra, and panties (that was also my first time padding my bra)
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Paul Smith
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Former Engineer 3y
Originally Answered: What has been your best cross-dressing experience?
Im a 30 year old slim athletic guy. I once confessed to my neighbour, a
mature lady in her 50s one night at a local neighbours party we had both
been invited to that i loved to wear sexy satin lingerie. Not female
panties , i liked lingerie made especially for men. I had bent down to
pick something up from the kitchen floor and as my t-shirt lifted and my
shorts loose on my hips, my baby blue satin tanga bikini briefs became
visible at the top of my bum. I then began pouring another beer in the
kitchen when my neighbour approached me. She is 50ish and not bad to
look at , she was wearing a leather skirt and white blouse with her hair
pulled tight back into a ponytail that made her look like a sexy strict
teacher from school days.

She said hi to me and asked if i wouldn't mind pouring her a beer. I
would love to i said and turned to reach into the top cupboard for
another glass. Again my blue satin bikini briefs became visible above
the waist of my shorts. Wow i heard her say behind me, are you wearing
your girlfriends panties, i realised what she ment and pulled the back
of my t-shirt down to hide them. I turned to face her and was blushing
alot aswell as embarrassed. Erm no i stuttered im single at the moment,
and that they are mens underwear. They dont look like mens she replied
but they are cute and sexy, do you always wear underwear like that. I
was embarrassed and didn't want anyone else to hear her so i replied yes
all the time and carried on pouring her drink trying to act normal. She
then changed the topic and asked who i knew at the party , we both lent
against the kitchen worktop looking through to the living room where the
neighbours are dancing and partying and just chatted with are beers.
After 20 or so minutes she out of know where asked if i would show her
my satin underwear again, they are very kinky and i like them she said.
I became embarrassed again but excited aswell and put a finger in the
waist of my shorts and pulled away from my body so that she could see
down front. My shorts had come out enough to expose my satin bikini
bulge and the satin string sides that reached over my hips and she could
see everything as she gazed at my satin pouch. I let my shorts go and
looked around to see if anyone else was looking. I was shaking with
excitement and really turned on by now as my sexy neighbour was keeping
my secret to herself and not shouting it from the roof tops . WOW she
said again they are sexy on you especially with your nice tan. Do you
wear anything else she asked me, like what i replied. Well they are very
girly underwear, like panties, sexy satin panties she said so i was
wondering if your like bras or skirts and dresses and stuff. No i said
iv not tried anything else, i just like how these look and feel on me.

You've not tried them but would you like to she said. There's alot of
women's clothing you might like to wear. For example this leather skirt
of mine. She put her both hands on her hips then moved them down over
her ass. I stared at her ass in the tight leather skirt and imaged what
it would feel like to wear it. You would she said wouldn't you, you
naughty little boy and giggled. Lets sneak off from here and go to my
place, we could pass by your house and you could get a bag of your sexy
panties and put on a lingerie show for me.

Her suggestion had me tingling with excitement and i quickly agreed. We
quietly left the party and started the short walk to her house passing
past mine, when we arrived at mine she again told me to go and put some
of my “ panties she calls them “ into a bag to take with us. I was in
and out in few minutes holding a plastic shopping bag with 15 to 20
different styles of satin lingerie from thongs, g-strings, bikinis and
even a lipstick red thong satin leotard.

We arrived at her house just after midnight and she immediately made me
feel comfortable and welcome. She put on some music and poured us both a
large brandy and coke. We began just talking about anything again when
she asked if i was going to model my bag of satin lingerie for her . I
was very nervous and excited at the thought of modelling for her but
wasn't brave enough to start. Come on she said lets start with a proper
look at them you have on now. She reached out and opened the butten and
zip on my shorts letting them drop to my ankles then lifted my shirt up
and over my head. I then stepped out of my shorts .

I was now standing in my neighbours kitchen with only my white trainers
and a baby blue satin tanga briefs. Oooh she said circling me and
touching and fixing my underwear into her correct position. I was told
to walk in and out the kitchen for her a few times and all the time she
would grope and feel me. I would leave the kitchen and change into
different satin panties for her as we talked and drank brandy for the
next hour or two when she asked me to try on something else for her. I
was a little drunk by now and was enjoying modelling for her so agreed.
She disappeared upstairs and returned holding a pink satin french maid
costume which she held against me to check for size. Yes it will fit she
told me and to go change in to it. I was by now in a white satin thong
g-string and a little drunk so i went and put it on. I zipped up the
maid costume and adjusted it a little then walked back into the fully
lit kitchen. My neighbour looked at me with a wicked smile and was all
over me in seconds kissing and touching me. She kept putting her arms
round and lifting the satin dress to pull my thong up higher between my
ass cheeks as we kissed. Soon i was talking with my mature neighbour in
her kitchen dressed in a pink satin maid dress and drinking brandy while
she takes any moment to start feeling me up and talk dirty to me.

It was early morning by now and the sky was no longer black as daylight
broke. She came up close behind me squeezing my ass in the satin dress
and said iv got something else for you . Pour us a drink each and il be
right back. I poured the drinks and was putting the ice back into the
freezer when i felt her behind me, she squeezed my bum and then i felt
something else sliding up the satin dress between my cheeks. I turned to
look and she was wearing a black rubber strapon. I stood straight and
said im not sure.

She told me that I would like it if i tried and that she would be gentle

15K views
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James
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Former Retired 2y
I like to crossdress in the privacy of my own home and it makes me feel
so aroused and horny.

One Saturday morning during Covid lockdown I decided to clean my
apartment wearing crotchless panties and fishnet holdups. I had just
slipped into a pair of black lacy crotchless panties and my cock was
starting to get aroused and stiff when the doorbell rang so slipping on
my dressing gown I answered the door to the Amazon Delivery man who had
placed a parcel on my doorstep and was social distancing. As I bent down
to pick up the parcel my dressing gown slipped open and the guy had a
good view of my semi stiff cock and balls.

Sorry I mumbled as I tried to cover myself, oh that's ok he replied it
looks amazing and sexy, not what I was expecting him to say so I said
would you like to come in?

Well he just walked in and as soon as I closed the door he started to
unzip his trousers and I opened my dressing gown.. by now my cock was
rock hard, but the best was yet come when he slid down his trousers and
boxers there was a huge cock getting very aroused. Well I reached over
and started to masturbate it and he did the same for me.. within minutes
we were rubbing our cocks together, so good I could feel my getting
ready to squirt my hot creamy cum, as I told him that he said yes he
also wanted to cum and at that moment we both squirted together… after
cleaning my creamy cum off his huge cock with a few tissues and a quick
goodbye that was it he was gone to deliver his next parcel.

I have ordered several things from Amazon since but I never saw the guy
with the huge cock again.

10.6K views
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Kylie.j.96
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Been crossdressing most of my life1y
The most fun but also scariest at first was the first time i went out
dressed. It was haloween my freshman year of college. It’s the only time
I have actually had friends help with my costume and I killed it! Some
girls in my dorm “talked” me into doing a school girl costume.

I let them pick it out. Was the classic red plaid miniskirt, white
button up top, garter belt and fishnet stockings. With a white bra and
panties. Initially they were gonna have me to wear some regular undies
but I ended up wearing a thong…. Some prefunk drinks, jokes, and a dare
led to that.

I have long hair allready so they put my hair into pigtails and did my
makeup. They made me shave my legs. Was the first time I ever did that.
I was super nervous but excited. They had no idea I liked to crossdress
in secret. It was my first time ever doing it around someone or in
public. They definitely threw me in head first.

When we all were ready we walked to the house party. I was the only guy
dressed as a girl but everyone was really chill. People thought it was
hilarious and awesome. Got lots of compliments. I was actually almost
passable and looked super cute! It was so awesome to be in a short skirt
outside and moving around!

I got pretty drunk and had a great time! Only awkward part was falling
down on my way home. Totally flashed my ass to everyone. Waking up the
next morning with the skirt and top on the floor of my dorm, still in a
bra and undies was great. My roomate was passed out in his bed and
totally thought it was hilarious when he woke up.

It built a lot of confidence. It made me keep doing it every haloween. I
habent missed one yet!

21.9K views
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View 2 sharesAnswer requested by
Fun Open-Minded and Nonjudgementail
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D Johnson
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4y
Originally Answered: What has been your best cross-dressing experience?
I met a woman in a chat room. We were both married and started to chat
quite often. As time progressed we decided to meet for a weekend. I flew
to her and we had a wonderful time. We were both in almost sexless
marriages and the excitement of a rendezvous was powerfull. We were both
in our 50's at the time. We enjoyed fantastic sex the entire weekend and
decided to continue in our secret relationship. At first I did not tell
her that I enjoyed crossdressing but as we chatted each night on the
internet she realized my long held secret.snd said that the next time we
met she would help me to explore my femininity. It was incredible. She
was very accepting and enjoyed transforming me

I would keep my male persona the first day and night and then I would
become “Dawn” the next day and night. She convinced me to go out with
her in public fully dressed. We went clubbing and dancing (as
girlfriends) I was in heaven when we went to lunch in a very fancy
restaurant. She ordered so I didn't have to use my male voice. I even
got the courage to use the ladies room at her urging. All went well.
Unfortunately. Her husband became ill and she cannot get away for our
wonderful times together. We still chat and send text messages almost
daily. She is an incredible lover both as male and female as well as
girlfriends. We have matching nighties and have fun posing for each
other. Hopefully wr can explire more in the future.

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Blackie Shepard
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bi sexual, gay, 2y
dressed up, full makeup, knee high stiletto boots, diamond stud earrings
and walked in the ‘red light area’ got talking with some of the street
girls, one of whom invited me to be part of a three some, but her client
preferred another GG

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Heather
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full time crossdresser
·
1y
Being able to go out in public as just an ordinary woman with no
problems. Just wonderful.
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Dan
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May 19
Wearing the 40DD under a loose-fitting shirt and going grocery shopping.

It is so exciting knowing that I might get recognized or “caught” …
(though not “hard”, I will often “ooze” a bit thru my shorts during the
outing).

And, the reality is, I am not hurting anyone nor cheating on my wife!

I masturbate when I get home “safely” … (then put the groceries away!)
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Bobbi Cd
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Unbelievable feeling of them on my legs and body Feb 26
I was at motel next to adult book store and I had pantyhose on my hole
body and hoddi and my 6 inch open toe heels under my arms and I walked
over to the book store and I got poppers and a booth for a hr and then I
got my shoes on and I was playing with my body and I was doing poppers
and I opened the door and walked out and I was at the end of hallway and
then I got on my knees doggy style with my legs spread wide open and
then I was sniffing poppers and I was so high and I went back to the
Booth and left the door open halfway and I got a freaky and a black guy
looking at me and I got up and spread my legs wide open and then I was
playing with my pussy doing poppers and then I said u want me baby and
then I was being a little sissy and he locked the door and he puts his
big cock in my pussy and it was a big cock and he fucked me nice and
hard and he said I love u baby and he said I would like to sit down and
u get on the top and ki

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Tallsis4
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May 14
When a straight guy pick me up at the club , took me to his apartment,
we kissed , I give him bj and he didnt know I was transgender until he
took my panties and wanted to do it! He wasn’t even very drunk! We both
found this very funny!! We didn’t do it that night , but he called me
and we dated for a 4 months with sex!!😊
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Khloe West
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Boss at CEO of My Own Life6y
Originally Answered: What has been your best cross-dressing experience?
Wow!

Thanks for the A2A and I’ve no idea where to start or stop. Never
thought that I’d type these words, but there have almost been too many
awesome experiences to recollect! I could likely write a quite unlikely
novel length tome about it all, and all in the past 6–7 years!

After surveying myself and my wife? A few high points that had great
pics. I was going to choose my top 3, but asked her and she had some
great input as well, so visuals shall be the bar to clear. BRB while I
review lists vs. pics…and apologies if this gets long.

Top of the pops and where this all began in earnest? My “drag makeover”
at the hands of legendary drag queen Courtney Act. There was an odd
array of events that led to this, but this was rather the “kick off”.
You can use this link, or if you hit YT and query “straight husband goes
drag”, I’m about the only thing that pops up.

One of my first choices? About falling out of my chair at being asked to
model for a Trans* fundraiser book project that I was going to volunteer
“boots on the ground” support to.

Getting stage direction while in face, but not dress, in my first film
op…and the residual glitter that was with us for ages after the film
ending in a very Busby Berkley manner with LOTS of falling glitter.

My first request to do print/web advert photo shoot for a local resale
joint that leans vintage?

A MOST unexpected “kitchen makeover” at the talented hands of Stephen
Dimmick, who has done Vogue cover work. I was out to make notes on a
home repair job and things ran off the rails. I loved this! What he did
with my eyes? Amazing!

And you thought I was kidding when I said I could blather on all night…

In closing? (I know, most thought I likely never would at this point).
One of my fave moments was pushing beyond the visual in to the social at
a play called “Casa Valentina” by Fierstein and based loosely on the
book “Casa Susanna” and that escape in the day of the early 60’s. We saw
it with pals while I was in colorful drab, and liked it so much that we
decided to see it again, but this time I dressed for the event! It was a
play about transvestites, so why not fly the flag?

And yes, it did cause a few raised eyebrows in the “Men’s Room” during
intermission.

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Answer requested by
Gisbelle Belle
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Ezra Jones
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Auto Mechanic at Self-Employment5y
Originally Answered: What has been your best cross-dressing experience?
I can say that the best for me was the time I got pulled over by the
cops wearing a pink bustier with garters and stocking I was driving to
get a new dress to get with my outfit and I was stopped by the police
for having a out light when he came to the window u was wearing a pencil
skirt and a satin top with my pink stocking and hi heels. I was asked to
step out of the car and I was happy to do so.when I got out I was asked
why I was dressed like that and I told I had a date I was going to and
my girlfriend likes me to show up wearing something sexy I was thrilled
when he patted me down. I was wearing a bustier with underwire cups and
push up in a size 38c he asked me of my chest was all mine and I told
him that it was I had a lot of people drive by which was a thrill to
have people looked at me while I was all dressed up. I even paraded
around a little bit to she off for his dash camera and for the other
people who were going by I was nervous about it but I was also very
turned on when he e searching me

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Amber Fountaine
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A well experienced old Queen with a young heart.7y
Originally Answered: What has been your best cross-dressing experience?
Quite a few years ago there was a bar at a local Holiday Inn that got a
lot of business travelers. The bartender and waitress were both friends
of mine and knew both my male and female personas. Occasionally my
girlfriend and I would let some guy pick us up and we had it worked out
where the guy never knew I wasn’t really a woman.

On one occasion we’d had a fairly good time with a guy, nothing at all
spectacular, and the next night I stopped in on the way back from night
school in male clothing. The place was almost dead so I was able to tell
my friends about the night before and the girls were getting a big kick
out of it since the guy came to town often and was always bragging about
his sexual abilities.

No sooner were we done laughing about that then the guy comes in, having
stayed over another night and before he had his first drink in his hand
he starts bragging about how he’d serviced the two women he’d picked up
the night before and done such a masterful job that they’d both left
bowlegged.

As you can imagine, it was all the two women and myself could do to keep
from cracking up and when he went on and on, one of the women asked him
which of the two did he think was the hottest and he told them the
blond. Then she pointed to me, sitting right next to him, and said,
“That’s her right next to you.”

He looked at me; I smiled at him and said something in my femme voice
that I couldn’t have known if I wasn’t one of the women from the night
before. He slammed down his empty glass and that was the last time we
ever saw him.

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Anonymous
Updated 5y
Originally Answered: What has been your best cross-dressing experience?
I put out an ad for men who wanted a CD, talked to several online for a
week or two and choose a couple that I liked and seemed compatible. Made
a date for drinks. Went in skinny jeans and silk top with A cup unpadded
bra so I was androgenous but not too obvious. We talked and it got more
and more into what we liked sexually. He finally invited me home. I had
a micro skirt and thi highs with make up bag in my car. Changed and made
up at his place right after walking in the door. Super slut outfit
basically. Got a bit tipsy and did a line as he got down to boxers. Then
I stroked him awhile. He just lay back looked me over and moaned a bit.
Thought I might rip my panties. Teased him orally awhile then he turned
me over pushed my undies aside and lubed me. I made sure he had a condom
on before he took my virginity. Saw him about every week till he
transferred out of town.

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Anonymous
3y
Originally Answered: What has been your best cross-dressing experience?
My best experience was becoming a full-time sextoy slave slut for a
daddy. I have a daddy who has been constantly offering me to move in
with him and be his sissy slave. Back when I still had a job, I kept
rejecting his offer. Then, covid-19 pandemic came and I was laid off in
the beginning of the year. That’s when I eventually accepted his offer.

He laid out the rules that if I accepted the offer, there is no going
back, I will be a full-time sissy slave sextoy for him, I have to do
everything he asks for, no exception with complete submission. I was
hesitant at first but finally decided to accept. First thing he had me
do was to throw out all male clothes I had since I don’t need to be a
male any longer.

Next was to increase my slave clothings. He dropped me off at a mall and
instructed me to shop as much clothes and lingerie as I could. He
restricted my clothing to only revealing, transparent, sexy, or minimal
coverage type clothing. I had to come out looking like a slut when he
picked me up.

I had to update my ID with new address and photo of my slutty self. At
this point I already accepted my old life was over and there is no going
back.

The last 8 months have been the best time of my life living as
submissive slut. As a sextoy, I have been put to regular use either by a
fucking machine or by him. He also regularly shares me with strangers.
My only concern now is if he decides to kick me out if he finds a new
slut. I asked him and didn’t get a firm answer. I begged him not to ever
kick me out since I can’t do anything without him, nowhere to live, no
decent clothing, etc.

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April Marie
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Been in transition for 4yrs now1y
All of it is amazing, but my best experience was the first time I went
outside dressed female. My wife and 3 daughters went out on the 4th of
July to lite some fireworks …I was so excited amped up being outwhe out
of the blue two cops drove up on us as we were lightning fireworks they
approached us my heart beating so fast aasked for i.d they ran us and
searched the car top to bottom just harassing us but they had nothing so
they started questioning me about why I was dressed female I just said I
am a girl so I'm dressed as such..they finally left and we proceeded to
lite our fireworks..But omg what a rush for my first time out.

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Answer requested by
Fun Open-Minded and Nonjudgementail
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Phil Gray
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4y
Originally Answered: What has been your best cross-dressing experience?
The most amazing experience ive ever had,was the first time i dressed
for someone else

This was a girl i had reconnected with after several years

After communicating on socail media for some time,she out of the blue,
asked if i would share something that ive never told anyone.i asked what
she meant, she said “you know,sexual fantasies"

I thought on this for a week or so and decided i could trust her enough
to let her into my private thoughts and doings

I d been dressing for a long time previous to this,and knew what style
suited me,sizes,shoes, makeup,etc,so i messaged her that i love sexy
lingerie, stockings, heels,etc

She messaged back,

On the women youve been with,or yourself?

Well that was an opportunity i wasn't going to let go by and answered
“both but me especially “

I nervously awaited her reply which was

“id love to see that ,got any photos"

I replied, i would rather show her in person

We arranged a date where i would travel to hers and live out that fantasy

The time came,i had already shaved ,i made my self up,dressed myself in
her bedroom, while she waited in the lounge

I was ready to open up this whole new world although very nervous.

I asked her to turn her back to the direction i would be coming from and
walked out of the bedroom and toward her

I know she could hear my heels on the timber floor,as i walked up to
her,put my arms over her shoulders and hugged her from behind and
whispered in her ear,

you can turn around anytime u like

Her eyes grew biggerand bigger as she looked me over taking it all in
then told me to do a twirl

She took a huge breath in and said"oh my god you are such a sexy little
bitch arent you,,wow,i love it,you certainly do have an idea of style
and class"

She then kissed me deeply on the lips then apologized for messing up my
lippy, but couldnt help herself

Needless to say we've had many gurl nights in,gurl days shopping

9.5K views
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The CCL Electrician
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Electrician (1995–present)
·
1y
When a man invited me into a booth at a local ABS. He pulled me to him
and gave me a long passionate kiss while his hands massaged and rubbed
my ass. Then he pushed me to my knees so he could feed me his cock.
After dumping his load in my mouth he pulled me up. Then dropped to his
knees, lifted my skirt and pulled my panties down. Then proceeded to eat
and finger my ass. Once he recovered he stood up and proceeded to fuck
me. We spent more than an hour In that booth. Making out and me sucking
and getting fucked. Ended up the start of an enjoyable friendship in
which we would meet for a repeat.
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Anonymous
5y
Originally Answered: What has been your best cross-dressing experience?
I'm a man with large breasts which amply fill a C cup. I've been wearing
a bra every day for many years with my wife's knowledge. In fact she
helped me with sizing and fitting when I first started but not I'm doing
it on my own. She's been sexually adventurous and likes to take the lead
and dominate me. She started the domination by using her fingers to
penetrated me, then a small dildo and finally a strapon. With the
fingers and dildo, I liked the feeling but with the strapon, it opened
up a whole new world. The first time she used it, she gave me a
memorable anal orgasm.

The cross dressing was her idea of making me submit. I was laid off from
work a few years ago and she told me I needed to take over the housework
and to do it dressed as a woman. Then she made it my job to fix her
dinner every night. One night she got frisky and showed up in the
kitchen with her strapon and had me bend over and take right there.

My best cross dressing experiences have been the times when she has also
cross dressed as a man and dominated me sexually.

17.8K views
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Kaleigh Andrews
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Experience in Cross-Dressing & Wearing What Is Comfortable, School of Life
·
4y
Originally Answered: What has been your best cross-dressing experience?
My ex was out supposedly working late (later I find out she’s been
partying and cheating) I got all dolled up and went to a bar and ended
up chatting the night away, while sitting at the bar, with an amazing
genetic girl who was in a messed up relationship. She was awesome and
the chat great. Have since wished I would’ve gotten her number and kept
in touch. She instantly was cool with me dressed as a girl and suggested
tips for my makeup and stuff. I was on cloud nine as we left the bar and
went our separate ways to our cars!
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Jo Dunne
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Under these clothes I am completely naked
·
1y
I have driven across the country dressed and that feels great. I once
went to meet a friend I had met on line, she knew I was dressed and
insisted I come across without changing. That was an incredible evening,
it happened a couple of times again and I keep in touch with her.
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Kalissa Foraday
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6y
Originally Answered: What has been your best cross-dressing experience?
Before my wife passed away her fantasy was to have a bi exp but cause
she was sick we never went out so i did the best i could for her and
surprised her and one night i fully dressed for her !

I wrote her a letter telling her i had a surprise for her and to be open
minded and enjoy ! I told her to come to the bathroom !

I had a bubble bath drawn candles and all and i was standing there all
dressed up and said hi im your maid slave for the night come and let me
bathe you !

She was like dazed untill i slowly bathed her and ran my nails all over
her ! Next i shavec her legs and pussy teasing her as i did till she was
excited as hell and said lets go to bed !

She laid back and i handed her a letter saying i was her bitch for the
night hers to do or have do as she pleassd and told her to name me and
if she wanted to use it there was a strapon unddr the bed to use as her
cock if she wished !

As she read the letter i teased her with my nails and whispered feed me
my precum ! Quickly she had a huge gob in her hand and i was lapping if up !

Long story short we both loved it and i loved her using the strapon !

After that night we would make it a all weekend thing sometimes

15.2K views
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Nick
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lingerie enthusiast also part time crossdresser
·
1y
It happened just a little over a month and a half ago. The day after
Halloween. My roommates were gone on a weeklong vacation. I took the
opportunity to get my makeup done professionally. I had the best
experience! Her studio was in her house and did a FANTASTIC job. We
quickly became friends and to this day she will answer questions that I
have and was not bothered by doing makeup for a guy.
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Rexann Love
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Part time sissy slut and full time cock lover 2y
The best dick I have had iin me was a very well hung black mans cock he
was all of 11″ and thcker than a cock can and I want him to fuck me I
never had black black dick in my ass But at 25 yrs old I got it He had
to pussy very hard to ge in me yes it hurt some bu tthe fucking he gave
me was so well worth it I became a real woman then and many time after
with him Black me love to fuck white sissy ass like mine I knew I wanted
a black cock to take me and take me he did My hole wa sore for a week
and a week later I went right back and let him fuck me again I think
most white sissy;s want a black man to fuck us Just like white women who
once the black man takes there pussy there hook on it I got hook on it
But yet I still let white men fuck me to even some hot lation men fuck
me A coc is a cock and when I am whicof th is so much he time I want a
cock makin love in my ass I never can refuse a man that want to fuck me
I soread my legs open for and mans cock

11.2K views
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Geneviève...
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1y
Hello all you beautiful people… 💕

Im a Trans Woman have been out since July 2020… my best experience as an
open TW is receiving a birthday card from my Aunt with the correct name…
“Ms. Geneviéve Sapha”… that put a huge smile on my face… Aunt ‘E' has
known my preferred name for a while… however, she texted me a few weeks
prior to my BD and asked me what my title is… geeze, never once
considered a title… I told her I'd like ‘Ms.’ 💕
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Andri
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1y
Impossible to narrow that down to literally thousands of instances..
Every situation although similar is completely different because every
human being, every age of either gender has their own unique personality
and reaction to my crossdressing in different environments. The
reactions from very young people under specific ages split between 4 age
groups within a 15 year spread is undeniably the best as far as confused
reactions go..Its an exhibitionist trait to show oneself in infinite
ways, which by the very truest definition of exhibitionism is to shock
and confuse and its highly arrousing to watch and wonder what they're
thinking..Born with a very female looking body, dressed passably to many
scenarios, distance from near to farther imagining from my behind
thinking I'm a girl. Short short cute girly shorts ,tight to snug, to
more relaxed fit that in all give a different perception..Cute girl fit
t shirt, blouse, jacket, sparkly thong sandals..Hair styled like a girl.
Often wearing oversize stick on nipples or realistic silicone breast
forms in different sizes..Small barely noticeable breast curves make
people look more intensely wondering if I'm transgender on hormones.
Many times it's just these big outstanding stick on nipples that Cleary
cling to specific shirts that will really confuse..My jacket perhaps
covering my penis or in state of partial to full erection also clinging
to the shear or semi seethrough material in which all details, the head,
length, ribs, veins can be seen..Its a right opportunity to take my
jacket off or pullover to expose the fact that I'm not female and that
ever unique confusing moment when the onlooker even in direct momentary
conversation just stares in confusion with it being very large..Is it
just confusion or is there subconscious arrousal by them evaluating.
Actually going back out of their way to make up an excuse to look
more..Naturally by that time a large wet spot is a natural occurrence.
In this heightened mood, prec,m so abundant its almost like mini
ejaculations..Many times so arrousing, c,mming without hand stimulation
right in face to face conversation..I've long since understood that just
dressing a certain way by many females to garner their exhibitionist
turn ons is different in only one way, they just don't have a penis that
can show they're turned on..Its not necessarily having a perverse
attraction to someone specific, or that would be your secret anyway,
it's the exhibitionism to cause confusion that's exhilarating on its own
standing..

2.8K views
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Scott Helling
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Former Former ABS Worker (2000–2003)Apr 2
My best crossdressing experience was when I was working as a cashier at
my local ABS. When we were at work we had a choice on whether we wanted
to dress up or not. I always decided to dress up. I was getting ready to
close up for the night. I had to go around the store and make sure
everyone was gone. I was making my rounds and in one of the theaters
there was a male and female couple still. They had some porn playing and
they were still getting it on so I stood there and watched has they were
fucking each other. The female saw me watching with my cock out stroking
it. She smiled at me and kept getting fucked. About ten to fifteen
minutes later I was still there jerking off and she came up to me and
grabbed my hand away from my cock and she proceeded to give me a
blowjob. While I was getting one of the best blowjobs I ever had I was
getting fucked on the ass by the male. This lasted for another 10
minutes until I was filled in the ass by the male and I came down the
throat of the female. After we all got finished we cleaned up and went
our separate ways.

450 views
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Chris Lowe
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35 years of reading history and WW2 wargaming5y
Originally Answered: What has been your best cross-dressing experience?
As somone who normally wears a skirt at the weekend but doesn’t try to
present as a women my best experiences are those day where I get up, put
nn a skirt and then at some point later in the day my wife makes a
suggestion to do something which I would not normally do in a skirt
because she hasn’t noticed that I am not wearing trousers. I find it
wonderful and so suporting that my wife will comment on what I am
wearing without even contemplating that the fact it’s a skirt is
unusual. Just walking along the seafront with my wife when both of us
are in skirts is one of the most comforting feelings I know.

12.1K views
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Raymond Parkins
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Lives in The United Kingdom (1957–present)2y
I met this gay guy in 1983 I always want to know what he had hidden in
his pants took a likeing to him sraight away I was only in his company
for short period's of time each year he never saw me crossdressed till
1996 we were good friends he knew I was interested but it was 2015 and
he had been drinking for hours with his gay friends who were married
they went to bed he came to the hotel bar for a last drink with me well
more than one drink ha ha he was unsteady on his legs so I helped him up
to his room its 2 am I thought this is my chance and my friend was well
up for some action as much as me as his hands were all over my body and
inside my dress at the bar but as soon as I got him inside his room I
switched the light on and before the door closed I took the lead he was
nearly naked before we got to his bed never had chance to switch the
light on near the bed I quickly slipped off his pants and out popped a
huge cock after a lot of licking I could not belive what I had in my
mouth it took my breath away I was choking than a lot of loud moaning
and begging for more he then tried to pull it away shouting I am going
to cum I pulled him closer shouting even louder I am to cu**** to late
he never got the word out there seemed to be gallons of it I licked him
clean then switched the light on it was huge I found out it was 10
inches and very thick we were both knackered by then but next day he was
amazed that i took every centimetre of his weapon inside of me

Which he said would not happen he could not belive it that I could not
get enough of him with out crying in pain i can not put it in to words

The feeling I experienced all I knew was I needed more of his volcanic
tower so since that weekend plenty of fall out has spilled out of his
volcano I know which style of outfit to wear that makes him have major
volcanic eruptions and yes the best things are with waiting for in my
case 32 years rachel

10.9K views
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Rikki Chunn
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Out and proud trans woman
·
5y
Originally Answered: What has been your best cross-dressing experience?
Appearing in court to finalize my legal name change. The judge read over
the papers, realized he had misread them, and then stated that this was
going to be an appreciated break from the usual misdemeanor trials he
had all the rest of the day. It was over very quickly and I legally have
a female name.
I wore a nice conservative skirt and blouse with bra, panties, and
sandals. My wife was with me at my side, beaming proudly.
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Michelle Kent
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1y
I would say the best crossdressing experience I’ve had was my first ever
date, he took me out to a nice restaurant and he was so sweet and
treated me like a real woman
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Whisky Jack
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Public Crossdresser
·
Mar 13
When by best friend’s asian stepmother caught me wearing her pantyhose,
and she dressed me in her clothes until early morning before my friend
woke up. What was once a fantasy she brought to life, oh the games she
created. It was by her instruction or punishment as she called it,
forcing me to suck my own cock and to swallow my cum. She would use her
large vibrator on herself and in my ass until I showed her my mouth full
of cum. I never told my friend about all of the times I had sex with his
stepmother.
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Nick Compton
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Feb 26
I got really fucked up and got left at a water fall…..I was pisssed off
tremendously but I soon found my self going through a bag I had and saw
my ex had few things in there,I took a few more shots and a line or 2
and next thing I know I'm. Trying em on I found a thong and a lacey bra
that I liked just how they hugged my body sent a erotic tingle through
me but I walked down the river and back fiddle fadeled for a while and I
decided I was gonna go half way up the water fall to stretch out on this
rock soaking up sun….I get up there and get comfy and started to realize
that if u moved a certain way it sent tingles ive never fetll through my
body and I tried to resist but I cave in and started to feel myself it
started to feel almost too good changed position few times and each
switch I found new waves of pleasure. I'm starting to feel so much
extasy in news ways I never experienced

Then BOOM BOOM BOOM….I froze then a very delayed 4th BOOM and I knew I
had company and that I was caught…..on display in a wo.anns lace bra and
a very revealing thong……so I tried to act normal and then I see my
guests 4 guys about my age in preppy barbie and Ken style and 2 old
timers ….they said nothing to me and startex to walk down river they
were pretty quiet and then it was silent I thought here's my chance
while they are down river I stand up quickly with my stuff and started
my exit and I hear “ see old timers one of them sissy boys in public “
uuhhgggg my heart hit the bottom of my stomach I turned and waved and
calmly said “my bad I didn't even see u I was in a zone “ some small
talk and 100 soft insults I was waiting 4 them to go but second turn to
awkward min and one of em said if ur ready to head out don't let us stop
ya…..so I jumped into the water and when I came up and was getting out
(not looking at any of them) but I could feel all eyes on me…one of the
old men said that he would be happy to help out if I needed it I kindly
denied and started to a place that was secluded when (and I still don't
know how they did it) one of the guys was pisssing and when he saw me he
didn't turn away from my direction his stream stopped he laughs and says
wanna help me shake it? He was a bit shorter and chunky his penis was
approximately 3 inches long and normal width ,he wasn't being hateful I
made light of it saying looks like he had it handled he chuckles and as
he is putting himself away says don't them get to ya,to each their
own,I'm straight and not trying to poke fun but u do look very
tempting….but you very kinda shifty to the old man when he offers to
carry something I was like I'm sorry wasn't ment that way he shrugs as
he takes few steps my way his hand still on his penis in his short gets
a stupid fuckin grin and says that old man was just she of standing full
strength from ur Lil outfit, so is ur cute Lil ass a faggot ?

No ,sorry to say not a faggot.

Hmm could've fooled my dick, funny I didn't think faggots were such teases…

Ii turn around to face him and 1 hand is gripping his hard dick the
other caressing his hip rib area

I told him I can't be involved appreciate the complement he made a few
more shots at me and I'm starting to get cold chills andi can
immediately tell he noticed my chest get goosebumps and my nipples get
hard as steel I go to ask what he wants and he answers a flip phone they
talk for a min then says I think I see u

I get so darn nervous thinking I'm gonna get gang raped but in the
distant I was relieved to see it was the old man who offered to help
with a huge smile and even bigger wave he works his way over to us and
chunkY boy quietly says

Alright man (pulls his pants up quickly) I'm going to be honest with you
I don't have a lot of money but what else do I have to do get u to pull
the old man's snake trouser a few times? I laughed said I wish I was a
prostitute but nope

He said I realize that now…I was thinking if u were it be easy I'd fuck
u and tell the old man u were gone…..

Just being honest don't judge me,

I was silent as the old man reached us he just latched on me with a big
hug and I could feel him grouping me pretending not to he was the
shortest of us three and the old man kept giving compliments and trying
to feel me up I asked where his buddies where he said up stream they
won't be down this way they don't like ppl like you, I felt anger and
embarrassed and again chunky softly says “so ull do that? I said no I
will not the old man didn't know our 🏪 he was focused on his new
mission to slid his finger in my Crack me constantly moving his hand,
chunky looking a bit defeated said well u got more get ups like this ? I
very hesitantly answered “ yes” he lite up and asked “OK no touching,
could the old man see u model them while he jerks his penis

I think it was the lines starting to kick in but I agreed with a
“fashion fan show “ the old man lite up and immediately dropped his
baggy old pants and he immediately started tugging at a half hard
cock….I froze then did like 8 steps towards him and by the 2 outfit I
was having Lil fun I'd get close to him n lick my fingers or suxk em dif
Lil things and I was surprised when I walked out outfit 4 and the old
man was on his back long stroking his dick and since it was the last
outfit I walked up to his feet got on all fours and crwaled over his
whole body and gave a kiss on his cheek his body shook I said that was
it but he was pointing out he wasn't finished and then begged me to not
let it go to waste they are few and for between I'm trying to leave for
to speak to chunky and he too is sitting vigorously jerkin off at this
point between the drugs and liquor I asked what could I do non physical
to speed this up chunky was faster fumbling words but clearly I heard
the old man “ face down ass up pull them panties tightly between ur
cheeks and rub your cock

So I did and idk why when chunky spoke I could barely make it clear I
heard from the old man say “ might as well us his own” chunky words were
clear when he said “ darn sissy boy,there's a gallon of precum here….the
old man said he was close and next I know I feel the most sharp intense
pain I jerked forward and whipped around to see chunky just unloading a
huge load of cum as his knees buckles and stumqbles where the last bit
is dripping on my stomach….as (http://stomach….as) he dropped next to me
he said sumthing about rape and man pussy and started to rub his nut on
my stomach like lotion I figured it was over when the old man kinda got
a serious tone in his voice so I closed my eyes and waited for them too
leave then clearly as ever I heard them say it's not moral right to
leave a sissy boy stiff and throbbing while covered in cum I tried
saying no but chunky said plus pops still full I tried processing this
but I felt my cock being stroked and I tried to fight it but the
pleasure running through my entire body was too much I gave in and
started to go along one of em said that I couldn't possibly hold out
much longer than chunky was in my ear whispering idk what when the words
were until I heard “HOLY SHIT pops working like a young buck!!!! And I
realized I was being raped by the old man……he was thrusting his cock in
and out of my ass over and over making sure to look directly in my
eyes…..I couldn't feel it at first so I tried to figure out what was
happening when chunky spoke…fuck you old man I want that boy pussy I
tried to move but seemed the old man somehow had super strength and he
turned me on my side and said “tell fat boy that he already had his turn
m wasted it,at this time I started to feel myself coming close to climax
and then I felt tremendous pressure on my face and heard “go ahead and
tell him I started to mumble words and then I felt it …..the old man's
dick in long slow strokes penetrating my ass to make my mind believe it
was that I reached down and felt him penetrating me….they talked to each
other excitingly and then I said I'm going to cum and the chunky bastard
squeezed the base of my dick strong and hard and said not b4 me and I
felt my stomach cut I thought he already did and felt his nut,and the
old man started thrusting faster and harder chunky was into it and said
squeez the bitches face again and the old man going faster and faster
gripped my face so hard my mouth forced open and chunky said I ain't
never had no batch boy make me nut by looking at me I closed my eyes and
old man said make it count chunky shoved his dick in my mouth and the
old man started shaking as he thruster himself in my a few more solid
hard times he stated shaking and chunky was trying to gag me I guess but
he was only 3 inches the old man now started to choke me and said I
ain't going to finish b4 no bitch and would pull almost allll the way
out and slam so hard and fast in ,chunky wasmoaning grabbed my head and
I felt his cum fill my mouth as the old man said there we go and
ejaculated forcefully and a lot the old man said take it as I felt him
swell and unload In my ass…..I couldn't move and chunky made a joke
about where's and the old man said like this? Put his penis on my face
and then smacked me full force calmly said that's what sissy boy slots get

556 views
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Kelly
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Updated 3y
Originally Answered: What has been your best cross-dressing experience?

I used to go to a Club in Philadelphia called Shampoo which had
Alternative/Fetish night. My female friend made me up nicely in the
face. 6.3″ heels and skirt this short made my legs look so good I was
willing to endure the pain.

Like minded people and compliments on my legs(That is me) made me feel
more comfortable.

5.4K views
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Matt Manning
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4y
Originally Answered: What has been your best cross-dressing experience?
I started cross dressing when I came home from work. I had met a guy who
was gay, but masculine. One day I just told him that I wear women's
clothes when I come home. He knows me as a masculine guy and said he
would like to see me dressed up. He invited me to his house and said I
could dress up in private and show him. I had always thought about
feeling a hard cock and my mind was racing. I packed a bag and went to
his house. When I got there he offered me a drink and he said relax. He
grabbed my hand and said I'm hard already. I was rubbing his cock. I
went and got dressed. I came out in a cute skirt with nylons and heels.
He was sitting there naked and he said nice body. He grabbed my hand and
walked me to the bedroom. My cock was hard but I could only think of
sucking his cock. We kissed and played with each other. I asked him to
slide his cock across my pantied ass and he did. Slowly I started to
undress as I stopped occasionally to suck his dick. I really wanted to
feel his cock in me but my girlfriend used a little dildo and his cock
was too big. Eventually I swallowed his load and he had me jerkoff on
his chest. We've had other experiences, but the first one was the best.

8.3K views
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Spencer Sawtelle
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High school from East High School, Erie, PA (Graduated 1990)
·
4y
Originally Answered: What has been your best cross-dressing experience?
Meeting my boy friend at a gay club we danced we laughed we drank ..and
the first time we went out on a date to a movie and dinner I
crossdressed I was really pretty and femine for him had sexy lingeria
under my dress because I wanted him to see it and fuck me the first time
which he did it was great I love being fucked crossdrsser as a woman so
much we had a great time ..this is one of my best moments as crossdrsser
...yea he's still with me 2 years now

… (more)
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Cindy Sanchez
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Former Sex Slave
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6y
Originally Answered: What has been your best cross-dressing experience?
It was last year for my bday my wife took me shopping and she about me
sexy lingerie we got are nails done and she took me out to dinner and
then to the clubs. Well when we got home there was 5 big black guys.
After a couple of drinks my wife told me it's time to change into my new
sexy lingerie. OMG after that night I was very happy and very tried but
let me tell you something for the next 4 days I couldn't sit down and I
couldn't walk straight either.
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Miss Jazzy
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Diva (1976–present)
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4y
Originally Answered: What has been your best cross-dressing experience?
Some years ago I met up with a lovely group of CD’s that got together on
sundays to get dressed up and watch the football games together, share
tips and secrets, BBQ and just have an overall good time. My GF at the
time loved the idea, she knew after me being dressed all day and around
like minded individuals, i’d come home and we’d put on our matching
lingerie and have a great time in the sack. I miss my lovelies and I
miss my ex as well
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Jayne Rogers
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Former Independent Means
·
1y
I'm coming at this question from a different perspective, I'm a woman
who dated a crossdresser whilst I was a university for about 7 months
and I can honestly say the sexual intercourse was absolutely amazing I
married a man a couple of years later and for the the next 15 or so
years of marriage I came nowhere near to having the intense, passionate
and enjoyable love making as I had with that person..

I'm now in a relationship with another woman and we're set to marry next
year and we're reaching the same heady hights as I did at university.
Profile photo for Anonymous
Anonymous
3y
Originally Answered: What has been your best cross-dressing experience?
I stayed with my Grandparents one summer. Both of them were slowing down
and they needed help doing things around the house. I was used to doing
things for them, so I didn't mind the idea at all!!

When they met, Grandma was a dancer with the Radio City Music Hall
Rockettes and Grandpa was a Junior Executive for a large company. They
married young, raised three children, and lived in an affluent
neighborhood. They were always invited to parties becouse everyone liked
to be around them!!

The attic of their house was renovated years before and turned into a
studio apartment. It had a separate entrance, living/dining area,
bedroom, bath, and a kitchenette. My Uncle had lived there while he went
to college and my Mom stayed there after she divorced my Dad. It was my
turn now!!

One day, I was left home by myself. Grandma attended the local art show
and Grandpa played his weekly round of golf. I didn't expect either one
until late. I had planned on surprising them with a nice dinner that night!!

I was upstairs vacuuming when I noticed a door that I had not seen
before. I opened it and found a storage area full of formal clothes. On
one side were mens suits, shoes, and a dresser and on the other were
beautiful womens dresses and gowns, shoes, and a dresser. There were
womens dress hats, purses, wigs, a full length mirror and a chair.

I always wanted to dress formally, but never had occasion to. Now was my
chance!!. I took off all of my clothes and laid them aside.

I opened a bureau drawer. It held a selection of bras, slips, and
underwear. Other drawers contained stockings and garters, and dress
gloves of various lengths and styles.

I put on a slip and underwear, stockings with garters and a pair of
white pumps with heels that fit me. I found a blue dress I liked and
tried it on. It fit really well!! I grabbed a wig, purse, hat with veil,
and a pair of long white leather gloves and headed downstairs in search
of makeup and jewelry.

I went into Grandma's jewelry box and put on a necklace and matching
earrings. I went to the bathroom, put on the wig, and applied makeup and
lipstick. I was feeling really good and looking good too!!

I put on the hat and carefully worked the gloves on and pulled them up.,
grabbed the purse, and headed to the mirror. A voice behind me said,
“You look beautiful!! I have been waiting for this day!!” It was Grandma
standing there with tears in her eyes!! I found a tissue, wiped the
tears, apologized, and hugged her!!

We went to the kitchen and she made tea. She asked me the questions and
I answered every one. She complimented me on my outfit but suggested
that I switch out the leather gloves for a pair of long cotton ones as
they would be cooler. I did and she was right!! She said it was OK for
me to dress around her and she would help me.

She asked me if I wanted to stay as I was and go back to the art show
with her!! I said “YES!!” She said I would be introduced as her
Granddaughter and by my female name!!

We drove back to the art show and had a great time even though I was a
nervous wreck!! I got complimented on my outfit and it helped my
confidence a lot!! As promised, she introduced me as her Granddaughter
to several people there. No one questioned her about me. We left and got
home in time for me to change before Grandpa saw me.

She helped me dress several more times that summer. We went places and
to social gatherings together with me dressed as a female!! It was a
blast!! Unfortunately, she died the following winter.

I never will forget those times with her!! I think about them and smile
every time I dress now…..

6.8K views
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Ben F
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Former Software Engineer at Google (company) (2011–2023)5y
Originally Answered: What has been your best cross-dressing experience?
I don’t know if this counts as I wasn’t the cross-dresser in this
experience.

While I was in college, I went to a party with my roommate. My roommate
(male) had long hair—perhaps down to his mid-back. For this party, he
wore a tight red dress.

Multiple times over the course of the party, I’d see him from behind,
and think “oh, who is this girl in the red dress I haven’t seen/met
yet”, and then realize “oh, that is my roommate”. Then I’d drink some
more, and later have the same experience. I told him I got a bit
frustrated after a while because I’d be like “oh, she is kinda cute I
should go meet her”, and then nope, its just my roommate. He was highly
amused that I kept repeatedly mistaking him for a female from behind.

10.5K views
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David the Dandyman
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Former Craftsman at Self-Employment
·
1y
Attending a performance of ‘The Rocky Horror Show’ in full make up,
stockings, heels and lingerie.. Then when a friend comments, “you make a
very pretty woman David!”
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Dwight Lopez
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MBA from University of Maryland Global Campus (Graduated 2020)8mo
I was in my early 20s when I met a married man who frequently traveled
to Chicago for business. My boss introduced us, expressing his
willingness to assist the man, Tony, in any way necessary. Eager to
impress my boss, I eagerly went above and beyond for Tony. After a few
months, Tony asked me to pick up a gift from a store and deliver it to
his hotel room. While waiting for the order, I couldn't resist browsing
the expensive lingerie in the department. When the package was ready, I
brought it to Tony's room. He opened it to reveal a white lace bra and
panties, insinuating that he knew I wore a bra on a previous occasion.
Overwhelmed and embarrassed, I admitted that his assumption was correct.
Surprisingly, Tony encouraged me not to be ashamed and asked me to try
on the lingerie for him. After changing and showing him, he praised my
appearance and hinted at further exploration. He invited me to join him
for dinner the next day, with the lingerie as a gift for me to keep.
Eager to please him, I agreed and made plans to meet him again. The
following day, I found myself in Tony's hotel room surrounded by
dresses, lingerie, and makeup. A woman named Debbie arrived, referring
to me as Tony's "special friend." Unsure of what I had gotten myself
into, I allowed Debbie to groom me and apply makeup, even trying on
different wigs. Tony arrived, impressed by my transformation, and we
embarked on an evening out as a couple. Despite initial worries, no one
recognized me, and I felt a surge of confidence. We attended an art show
and enjoyed each other's company until returning to the hotel room,
where we engaged in passionate intimacy. This marked the beginning of a
two-year relationship as Tony's girl, Jenni, filled with incredible
experiences. Eventually, our relationship came to an end when Tony
retired after selling his business. Although it was bittersweet, I
cherish the memories of the unforgettable time I spent as Jenni.

650 views
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Hugeskirts79
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Once wore a victorian dress over a hoopskirt
·
1y
Definitely wearing this huge victorian dress over a very full prom dress
full of petticoats 😍

… (more)
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Anonymous
4y
Originally Answered: What has been your best cross-dressing experience?
I don’t consider myself a crossdresser at all. I wouldn’t be into
wearing anything super girly or exaggerated, basically just dressing
like an average (younger) girl. Wearing some basic panties under
somewhat gender-neutral clothing, and having all of my body hair
shaved/waxed. I prefer acting feminine and being identified as a girl
when I’m doing it, but again, nothing over the top. Think of an average
unassuming and shy girl in high school or college. I’m basically going
for that.

The important things for me are feeling feminine and being submissive. I
want to be with a guy that’s completely in control, and if we have sex,
I want to be treated completely like a girl, like my boy parts aren’t
even there and don’t get touched at all. I want to focus on pleasing
him, and maybe be lucky enough to have an orgasm occasionally from him
being inside me. I would be ok doing things with a guy my own age, but
would much prefer a much older man, sort of a ‘daddy’ type or something.
Someone authoritative and dominant, the kind of guy that wouldn’t have a
problem pulling down my panties, putting me over his knee, and paddling
my bare bottom until I’m in tears whenever he thinks in need it.

So I met this guy a while back. We chatted online for a while, and one
night I got brave enough to go to his house. I’m in my 20s and he’s in
his 50s, and he’s into spanking. All good things so far. I shaved all my
body hair and wore my favorite cotton bikini brief panties under my
not-too-girly outfit, basically a T-shirt and some cute sweats I think.

He lets me in and we have a drink while we get to know each other. I’m a
little nervous. Then the mood shifts a little, and the conversation
almost turns to a lecture about meeting strangers on the internet and
going to their house. Suddenly I feel like a teenage schoolgirl that’s
about to be punished, which was both amazing and terrifying in the moment.

He gets up and leaves the room, and a moment later I hear him calling me
into the other room. I find him sitting on the sofa, and then I notice
the big wooden hairbrush sitting next to him. I don’t remember exactly
what was said, but basically called me over and told me that in need to
be taught a lesson. The next thing I know he’s pulling my pants down and
putting me over his knee. A few more words are said, then I feel his
hairbrush landing on my butt.

I was squirming after the first few swats, but he just pinned me down
and kept going. After probably like 50, he stopped for a minute and
talked to me again. I almost thought it was over, and then he pulled my
panties down. I probably got like another 50 swats on my bare butt. It
made me cry, and I could tell my butt was bruised.

I was laying across his lap, so I could feel him getting hard while he
was spanking me. After he stopped he rubbed my butt for a minute while
he talked to me. I could tell he was really hard. I felt his fingers
exploring between my legs, and other places.

He told me I could get up. I just stood there, not really sure what to
do. I looked down at the bulge in his pants, and he knew that I saw it.
He looked in my eyes for a minute, and a lot was said without words ever
being spoken. He started pulling his pants down, and I instinctively got
on my knees. I leaned forward slightly and arched my back so he would
have a nice view of my now very bruised butt.

It was my first time so I had no idea what I was doing. I just took him
in my mouth and followed my intuition. Apparently it worked, because a
minute later, his cum was shooting down the back of my throat for me to
swallow. I could tell how good I made him feel. I wasn’t sure what to do
or expect next, so I just knelt in front of him and waited. I couldn’t
help noticing how good it felt to be sitting there with my panties
pulled down around my knees, cum running down my throat, and having my
butt blistered from the spanking it just got.

But apparently it wasn’t enough for him yet. He told me to get up, that
he wasn’t done with my spanking yet, and that I should never expect a
spanking to be over with that quickly (never mind the fact that I
already probably can’t sit down). But I can’t help being happy that he’s
doing it, and that I don’t have a choice.

He has me bend over the arm of the sofa and takes off his belt, and
tells me that if I get out of position or try to resist, my spanking
starts over from the beginning with the hairbrush. He gives me like 20
with the belt on my butt and upper thighs. It’s not as much about
punishing me this time as it is about showing me my place, and reminding
me that he’s in control. At one point he asked me a question, and I
caught myself responding “yes, daddy.”

He told me I could get up. My butt was throbbing…just pulling my panties
back up made me want to scream. He took me upstairs to his bedroom and
told me to get undressed, except for my panties. He had me lay on the
bed face down and rubbed my butt for a minute (which by now almost hurt
as bad as being spanked) while he talked to me more. He told me I was
his, and that I wouldn’t be meeting any more strangers. He told me his
expectations and rules, and consequences, for which this was obviously a
demonstration. I would be available to please him whenever he wanted,
and misbehavior would always be met with a hairbrush and a belt on my
bare bottom, among other things.

He spent the next half hour explaining everything while he whipped my
butt. I got to keep my panties on for the first few minutes, but he
pulled them down long before it was over. At one point I yelled out a
bad word…his belt must have landed in just the right place on top of a
bruise. He stopped for a minute and told me he wouldn’t tolerate that
kind of language. “Yes, daddy.” He left the room, came back and put a
bar of soap in my mouth, and told me I was not to spit it out until my
spanking was over.

By the time it was over, I was completely limp and drained. I wasn’t
even really crying anymore. Just an occasional tear. He grabbed my butt
and squeezed it, which nearly made me scream, and told me it was his
now, and asked me if I understood. “Yes, Sir.”

I heard him getting undressed. He didn’t say another word, just climbed
on top of me, and the next thing I knew he was inside me. It didn’t last
long. This definitely wasn’t for my pleasure…it was more about showing
me that he could. I could feel it when he came, which still made me
happy. He pulled my panties up, pulled a blanket over me, and kissed me
on the cheek.

I think I passed out before my head hit the pillow. I woke up to him
telling me breakfast was ready downstairs. I knew I was in for a long
day as soon as I sat up. My butt was throbbing and on fire. Just wearing
panties made it hurt to walk. He made me sit down at the table with him.

After breakfast he called me up to his room where he was getting ready
for work. He asked me if I had any questions about anything we talked
about last night. “No, Sir.” Then he told me to pull down my panties and
bend over the bed. I didn’t even ask, I just did it. Quickly.

Which was apparently the right answer. He said he would have repeated my
entire spanking from last night for the slightest hesitation, but since
I obeyed immediately I was only getting 20 with the belt.

I heard him unzip his pants and call me over. I got back on my knees in
front of him once more with my panties pulled down around them. I wanted
this to be the best ever. Something he would be thinking about all day.
I licked the tip, then took it slowly to the back of my throat. I licked
down the shaft and slowly made my way to his balls. I licked them while
I stroked him, then slowly made my way back to the tip. I could feel him
about to cum and took him deep in my throat. “Thank you, daddy,” after I
finished swallowing him. “Can I have it again soon?”

“Yes, princess. You’ll be back tonight.”

11.9K views
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Scott
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Retired truck driver
·
9mo
When I got dress in my mini dress black pants hose heels and went to my
local park and walk around had men looking andyelling at me then I sat
down on a bench and a older guy set down next to me pulled his cock out
and ask me to suck it so I did and when he got hard he said I want to
fuck you so I hope on his lap and he put it inside me and made me his
batch for the night it was great I had to orgasms and he had one huge
one inside me
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Steffi
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All my life 1y
I’m thinking the night I went to a well known dance club with three
women friends of mine, they all knew about my crossdressing and seemed
to like it. Well we were all very dolled up, all of us wore cute dresses
and sexy heels and I as always was very nervous, huge difference going
to a regular dance club as to a gay club. But once I get to are table
and get my first cocktail down I’m usually ok, so on this night for some
reason I was getting all the invites to dance and the other girls who
love to dance were getting pissed and asking what the heck 😆 they were
all blondes and I a brunette so I said I guess blondes don’t have all
the fun. But we all really had a blast just dancing and chatting with
guys that would come sit with us.

3.9K views
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Answer requested by
Fun Open-Minded and Nonjudgementail
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Lacey Femme
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20 years dressing up1y
There were two experiences I remember when the crossdressing itself was
very memorable, independent of where I was or what I was doing. They
both occurred when I was beginning to get comfortable with going out
dressed, but wasn’t quite there yet. The first event was going out to a
bar for a drink wearing an LBD, just sitting and talking with several
people. The second time was a visit to an adult theater when I had
dressed pretty provocatively, and parked 2–3 blocks from the theater and
walked the rest of the way after dark. In both cases, it was just so
rewarding and liberating to finally be myself in front of other people
without worrying about it, and realize that the sky wouldn’t fall.

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Answer requested by
Fun Open-Minded and Nonjudgementail
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Denise Parker
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Wearing skirts as often as possible
·
2y
The answers here are awesome stories, for me, it was buying my first
breast forms. My dressing experience had been awesome, but as soon as I
added breasts, that look and felt like breasts, I was over the top! My
“girls” D cup have taken me to a new high. You gotta try ‘em!
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Evelyn
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50 plus years of wearing womens undies and clothes.2y
I have had lots of good experiences related to the “hobby”. The most
memorable was getting a bra fitting and learning a lot about lingerie
while there.

I went to a small lingerie store in an shopping center, more than a few
years ago, and wanted to buy forms. The lady asked me my bra size and I
was stumped, other than what I had bought. She said the only way to know
what I needed was a fitting so off we went to a dressing room. after
trying some bras and forms, ended up with a beautiful lacy 38C and a set
of weighted foam forms. Tried on panties over boy undies and body
shapers, bought one also and several pairs of panties. A great hour or
so and two bags of quality lingerie and a lifetime of knowledge.

5K views
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Kinison Maxel
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Driver at Self-Employment (2014–present)
·
3y
Originally Answered: What has been your best cross-dressing experience?

Mine was doing the census! And she said that she had to ask if i
identified as male or female! That was great!… (more)
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Yudro Borges
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Wearing dresses and other casual cross dressing since 1980
·
7y
Originally Answered: What has been your best cross-dressing experience?
Shopping for a leather bustier at a store in San Francisco. The
saleswoman was SO nice, helped me pick something out, helped lace me up
once it was on, suggested other things I would like - made the whole
experience SO MUCH FUN!

Otherwise, went to a drag club, and the performers were so cool - I was
in a dress and one of them pulled me out of the line to get in: “You
don’t have to stand there, there’s a drag line, baby!”, got me a seat a
the front of the club. Realized that in a drag club, most of the guys in
drag were straight, and most of the guys in guy clothes were gay - gay
culture tended … (more)
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Kim
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Frequent restaurants wearing clothes from the womens dept.
·
6y
Originally Answered: What has been your best cross-dressing experience?
Today I stopped at a local bar in a hip part of town as a bald headed 60
year old man wearing missies Bermuda shorts, sling sandal with tan and
gold and and a floral sleeveless top that had a low v neck and a
friendly wait person told me I looked fabulous. She’s told me before
that she liked a shirt I was wearing but now I looked fabulous!
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Paula Hayes
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Gender female , eat drink everything girlie
·
10mo
Sorry but your question comes over as if it’s game they play ,from my
view it’s like everything in life ,you learn too get better at it ,&
once you know your destiny?ie the path ahead ,f/time , stay secret, but
remember,someone’s Body ,looks , age weight, are different, but everyone
who progresses do so from their heart and mind x
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Nikky Fiuri
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Lives in Chicago Heights, IL (1973–present)
·
4y
Originally Answered: What has been your best cross-dressing experience?
I've had some great gangbangs and twice I went onstage with a
well-endowed gurlfriend and held on to to the stripper pole while she
impaled me really good.

I was at a sex party one night

and managed to take a HUGE guy half way up in me while a few people
watched. By “huge”, I mean his dick was as big as a bodybuilder's arm!
It took me 45 minutes to get half of him in me and he was shocked and
thankful and so was I.

What happened during the next two hours with three other people is a
whole 'nother story………

Mmmmmmm!… (more)
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Monika Sveet
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Part time crossdresser for 20 years and I am straight.
·
Updated 9mo
I have a few very pleasant experiences as a crossdresser… For me when I
am dressed a woman, I like to be treated as a woman but at the same time
I do not like men… so, the options are either women or other CDs/TGs
like me. And all my best experiences as a crossdresser involve a female
partner who liked me dressed as a girl and make love like lesbians…

My best experience is written in detail at my space here. Visit this
story and tell me if you like it.

Quora
https://qr.ae/pKhlvN
Hugs.

Mona.
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Stephen Carr
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Owner Op4y
Originally Answered: What has been your best cross-dressing experience?
My favorite time was in Brownsville Texas at a hotel. I was fully
dressed and hogtied on the floor. My wife went to our rig to get some
things when housekeeping knocked on the door. Unable to objected through
my gag she walked in. I was laying beside the bed out of sight. She walk
to the bathroom and saw me. She asked if I need help and shook my head
no. She saw my keys on the floor but the dresser and I guess realized
what was going on. She asked if I wanted her to clean the room and I
nodded yes. So she cleaned it swept the floor. Got to me and grabbed my
ankles and pulled me to the side and finished sweeping. Than left asking
if I was sure I was ok.

7.6K views
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Howard Heckmer
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6y
Originally Answered: What has been your best cross-dressing experience?
Today, I am dressed in a black skirt,white blouse,my red wig,complete
make up,black nylons and low cut boots with 2 in heel.Walked into a
local lingerie shop and was treated like a true lady.I was in 7th heaven…
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Paula
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Lives in Nebraska (1999–present)
·
2y
The first time I let a man see me in bra and panties. I will never
forget it. He was gentle and supportive and when he caressed my panties
covered butt I came hard
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Anonymous
4y
Originally Answered: What has been your best cross-dressing experience?
It has to be wearing a huge black victorian petticoat of the 1860s with
blue trim just below the knee area that I bought for my girlfriend and I
did tell her my fetish for them before I got her it,loved it on her but
when she worked late i tried it on and loved the soft feeling of it on
me and rubbing my hands over the trim detail of it,masturbated like mad
to it n shot my load all over myself,love my girlfriend so much but the
huge victorian petticoats and skirts make my heart pound like mad too
for some reason.
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Soph Scots
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Lives in Glasgow, UK (1966–present)
·
1y
When along with 2 other girls I took part in a transgender fashion show
for charity,we practised beautiful for weeks and we loaned outfits from
dept store personal shopper.The finale was Bridal,and I was dressed in
the most gorgeous wedding gown,complete with tiara and walked down the
catwalk with my “groom" I felt so wonderful and beautiful just like a
blushing bride.I even shed a tear or two knowing how fabulous I felt but
also Sadly I knew I had to take the dress off but it still remains one
of the best experiences of my whole life,trans related or not
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Davina Smith
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Cross-Dressing since puberty3y
Originally Answered: What has been your best cross-dressing experience?
Since I have been crossdressing for so long, there are many but many
times the experience is generally similar. First, it is important to
consider that I almost always present myself as a male wearing what may
be considered feminine clothing.

So going out in public like that takes some getting used to. Not easy at
first. I believe dressing the way I do shares a similar trait as the
many who dress completely but are still new to it. It is a fear that you
will stand out so much that people will make a scene and draw even more
attention to you. So it is kind of a self fulfilling prophesy. You act
scared and it shows making you stand out.

It is very difficult to overcome without a lot of persistence. But
eventually things take a very interesting turn. You inevitably run into
people that you have to interact with. Even if it is only answering a
general question. But sooner or later, you have to face people if you
choose to go out dressed somewhat differently than most people expect.

What I found by accident is that after a while, you end up talking to
someone someone and “forgetting” how you are dressed. It happens when
you enter an unrelated conversation and talk for a couple minutes and
after you have what turns out to be a normal conversation, you suddenly
remember how you are dressed and realize it hasn't made a bit of
difference in the outcome of that conversation.

So my best experiences are when I have been shopping or just out and
about and have had a normal encounter with someone only to realize after
the fact that you are dressed in such a way that you expected a horrible
encounter and instead, you were treated just like anyone else because
your conversation was lacking any fear or self doubt and everything
feels completely normal.

I just love that feeling when I forget till after the encounter that
people can interact just as though nothing were amiss and you figure out
that dressing oddly doesn't really have as much to do with meeting other
people as does your attitude and body language. So many times, I have
completely forgotten how I was dressed when I got caught up in an
interesting conversation. Then you think about how your were treated so
normally that it makes you feel so much more at eased dressed like that.

It is a true indicator that most of the anguish and fright is just
generated in your own mind. And when you can relieve yourself of that
self-incrimination, you can dress however you like and learn that how
you act has so much more to do with the way people treat you. I
personally like grocery shopping dressed in all feminine attire
including small breasts and by the time you get to the cashier, you are
acting just like you would any time.

It is quite a rush to be walking out of the store and suddenly realize
that “wow” look at how I am dressed and nobody made so much as a
comment. I am certain many people talked about it behind my back but
that didn't bother me. The thrill that you can dress however you like
and still be treated normally makes it so much more fun and easy to do
again.

6.7K views
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Patrick McNeill
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Retired Police Chief Inspector (1992–present)5y
Originally Answered: What has been your best cross-dressing experience?

It was on a cruise many years ago and I was with a group of lads. It was
fancy dress night and we decided to do a mock hospital operation. I was
assigned the role of matron and given a pillow to wear under my apron to
make me look ‘female’, while I held the drip bottle as a string of
sausages was produced from the ‘patient’.

All very grotesque to my eyes after 40 years.

9.6K views
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Wendy Hand
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Former Crossdresser at Cross-Dressing (1971–2020)4y
Originally Answered: What has been your best cross-dressing experience?
I tried wearing my mom's panties when I was about 12. It made me feel a
funky kind of way. I never did it again.

1st ..10 years later... I met my first fiance. We we're very sexually
open and tried many things. One day she asked me to dress as a girl in
her clothes which I did and we had amazing sex.. we did it that way a
few times and then she started using and dildo on me..the relationship
ended because of other reasons.

2nd I was at a an adult party with a mix of men and other gurls like
me…it turned into and big pile of excited human flesh..everyone had a
great time.

rest of my history….Then forward another bunch of years.. my ex-wife and
I were on the outs and not having sex.. I got the urge to dress in her
lingerie and started using AOL groups.. then I had my first experience
with a man while wearing panties.. this went on ...I dressed more and
more for and with men.

I got married again I quit wearing for a few years and my wife still
doesn't know.. but I have restarted dressing full out and sharing time
with men.. I love my wife and sex with her too and tried many times to
bring this up as a let's have fun with our sex life but.. she always
says she won't like it.. I would love to get her involved with me
dressed and doing another guy. But for now it is only once in awhile
thing, it's not something I crave everyday.. but once in a while... And
then I get my fix.. and I'm done for a few months.

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Kari Crago
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Lives in Marion, IN (2012–present)
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2y
It was in 1997, I had just been out all-night partying at a local Gay
Bar dressed and I had to stop for gas and I wanted a coffee, when I
walked in the station a young lady looked up from a book and Said hello
and welcome and I waved to her, I got my coffee and she asked as I
approached the counter what the perfume I was wearing, I told her it was
Beautiful by Este Lauder, she got a shocked look on her face (my voice
is a dead give away) and says OMG I thought you were really a Woman you
look so pretty and feminine, my heart sang! I thanked her as I paid.