Have you ever had a sissygasm when cross-dressed?

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Asteria
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Lives in Setagaya-ku, Tokyo, Japan (2024–present)
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Jul 1
yes indeed. get a nice long soft dildo with a suction cup bottom. maybe
in the bathroom use the toilet seat as a base, use lube. hump that thing
like there is no tomorrow deep and hard. Once you get the rythm going
and you can learn to relax inside you will start to feel your legs
shaking, then you will feel your insides start to tingle then to a point
where you will hump the dildo really hard and deep feeling w euphoric
feeling you never had before…in a few more humps you will explode like
you never did before…there will be allot of cum… once you have one of
these you will never do it the old… (more)
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Emma Le
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Crossdressing
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1y
Ooh yes i have had a few, the first one I ever had was by pure accident
but aren't they all.

I was younger and dressed up at home in my moms clothes as usual. For
some reason I had decided to try out her exercise bike even though I was
fully dressed and wearing 3 inch heels.

So I sat on the bike and started pedaling and pedaling. The thrill I got
as skirt and peticoat rode up my nylon covered legs and the whoosh of my
legs rubbing together fast was so overpowering that I came almost
instantly and god I could not beleive how much I had ejaculated whilst
tucked my panty crotch was totally soaking … (more)
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Tara Lynn
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Jun 11
For me it takes a while to get a sissy gasm. I'll go to an adult
bookstore going the back rooms suck a lot of cock and let a lot of guys
fuck my ass pussy. But it takes at least four or more good hard fucks to
get me. To have a real good sissy gasm. Which is fine with me because I
love the feel of a hard cock in my ass. Plus I'm always wearing panties
stockings short shorts and tops. There was one time that I did have one.
by being spit roasted. Those two guys pounded me so hard I thought they
were going to meet in between. Inside me that gave me one fantastic
powerful sissygasm
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Celeste
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Crossdresser for over 30 yearsUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
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9mo
Related
How many cross-dressers have had or would like to be made love to by a man?
I had real sex for the first time while dressed when I was about 22

, with an older man who was about 50 but after when the moment ended and
the wig, make-up, lingerie and stockings came off - I found it difficult
to accept the things I had done and cried myself to sleep.

I felt incredibly guilty and got rid of all by dressing clothes and
tried to be a 'man'.

I again couldn't give up my dressing and had to purchase more feminine
clothes to wear.

This cycle went on time and time again.

The Internet makes it easier now to date and now that I am a lot older I
have managed to come to terms with my dres… (more)
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Sylvia Chartwell
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Former Owner Two High Tech Businesses. Semi Retired.
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May 25
Yes, usually after the fourth or fifth guy has pounded me. I had six
guys after this pic was taken. Mmmm.

… (more)
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Petra Spilles
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Design Consultant at Fruit of the Loom (clothing) (2013–present)
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Jul 5
There are a few guys who I hook up with who have just the right size
cock, and now how to use it, to make me cum when they’re fucking me.
It’s such an intense feeling being brought to orgasm while I’m getting
fucked. I like to wear crotchless panties, that allow access to my hole,
while keeping my clitty contained at the same time. Love love love the
feeling of filling up my panties with cum as I’m getting fucked!
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Randi
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New housekeeping
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1y
Yes while dick ng nice big cocks I'll cream iny panties. And if my date
has a big one way up on my ass I'll cum multiple times. Yep I'm a sluter-roo
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Sarah
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1y
I have twice, first time I hooked up with a guy online, he came over to
my place, I sucked his cock for a bit then he fucked me doggystyle on my
bed, he found the right spot and didn't take long I was cumming so hard.
Second time I was riding a dildo and was so horny I ended up cumming from it
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Ayesha J
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Started at 20, been doing it for 10 years.
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1y
I was close to this. One day at night while wearing my blue sleeveless
long dress. I had an experience I had never experienced before. I wore
this dress and spent a some time rubbing my dick and watching porn
videos. I realized that I was in an intermediate state. I had pre-cum
several times. They were smeared on my dress and leg above the knee. I
started shaking my body. I wanted to stay like this forever. I couldn't
hold it for long.
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Brandy Lynn
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Constantly being messaged by gay men
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8mo
I have given myself many ,thanks to me making a exact mold of my big
girl cock!!!and plenty of lube ..43 ur old virgin ..super sexual ,fun
and curious…
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Sarah Harding
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Lives in South (2000–present)
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11mo
Yes, I have these daily, especially when I put a dildo inside me and use
the vibrator on my little girly cock
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Egnargaled Kcirtap
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Lives in Akron, OH (1974–present)Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
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10mo
Yes…. Omg. The one and only time this happened I was in full lingerie,
thigh highs, garter, bra, panties pulled to the side and a boyfriend was
pounding me missionary at the perfect angle ….. and wow….. full orgasm
no hands
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The CCL Electrician
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Electrician (1995–present)
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1y
Yes many times. I have had sissygasms while sucking cock because the man
was so vocal and enjoying it. Also almost every time I am receiving anal
I have a sissygasm. The feeling from them is so satisfying and enjoyable.
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Matt
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Cross dresser since 11years old, in My 60's, still enjoying
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Mar 24
Yes I could believe that after several years of dressing and having my
first encounter with a man, home alone , nobody will be around for
several days, was looking okay, but once I saw his manhood, and really
enjoying it, I was so excited and I had one, it was messy
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John Lascuola
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I've been cross-dressing for 51 years and I've tried everythUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020) and
Ragnar Nobeard
, former Analyst - Retired at Experiences in Life
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1y
Absolutely yes I have and it's amazing it happened by chance I was
getting ready to masturbate and I had just got an 7″ vibrator. I lubed
up and inserted it and before I could touch myself I started cumming All
over the place and it was amazing and arousing I was totally surprised
by it but I have loved doing it for a different way to relieve myself.❣️
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Bernie Jordan
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Studied at University of Salamanca
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10mo
Since my wife start cuckolding me eight years ago, conventional sex stop
for me, all im getting is pegged once a month and i get a sissygasm, is
a whole and totally new experience, very intense and more pleasurable.
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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)
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1y
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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 a… (more)
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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 years
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Updated 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.