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What has been your best crossdressing experience?
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Profile photo for Carolyn Ann Harrington
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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Answer requested by
Fun Open-Minded and Nonjudgementail
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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.