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
·
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 Profile photo for Sarah
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 Profile photo for Ayesha J
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)
·
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. Profile photo for Matt
Matt
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Cross dresser since 11years old, in My 60's, still enjoying
·
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.❣️ Profile photo for Bernie Jordan
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
·
Updated 9mo
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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 rand… (more)
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Melanie Longfellow
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Retired in ohioUpvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
7mo
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Who are cross-dressers, and what are your experiences when dressed?
I began to experiment with crossdressing at 40 after my ex wife told me
after 22 years of marriage that she needed a more masculine dominant
take charge kind of man. I didn't blame her or get upset because all the reasons she gave me were true and a divorce was a great way for me to
begin exploring my feminine side. I was surprised she stayed with me for
so long because of how feminine I really was. I was 5 10 135 pounds with
long hair , very little body hair, small shoulders, arms, hands, a small
waist and big hips with a firm round butt. There were times I was
mistaken for a girl when men sa… (more)
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Freeda
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Former Mechanic
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Feb 24
Yes it was awesome my friend was fucking me real hard he’s well hung
felt so good I just blew everywhere.
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Cd Jenny
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Retired 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?
Yes, I was dressed up as a sexy woman, and heard someone at my bedroom
door. So I opened it and let him see me dressed and had him come in he
said I looked sexy and I could tell he was turned on so I stroked him
and asked if I could suck his cock, I undressed him and wrapped my red
lipstick lips around his cock sucking him off taking his hot cum in my
mouth. He then fucked me deep and hard in my ass. he came by every night
for 3 months while I dressed up for him, and got to suck his cock and
have my ass fucked it was such a great experience being able to have a
man who enjoys having a cross dresser

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Steffani Sweet
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Studied Behavioral Psychology & Forensic Psychology (college major)
(Graduated 1975)
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Jun 26
Yes.Several times. I dont wear panties or bra,and love short short
skirts,so there I get stimulated easily. The wind up my skirt can do
it,or the fabric of my skirt rubbing on my clitty will do it. I have
been walking down the street and cum. I love to cum in public.
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Delilah
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Lives in The United States of America (2023–present)
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Feb 2
Yes, I have. It felt so good and amazing. My whole body shook.
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Sasha Hopkins
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Self Employed (2021–present)
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Feb 3
Yes many times I'm a young pre op trans girl and I have a husband I'm 22
and I sometimes do the sissy thing for him and he milks me it's amazing. Profile photo for George Fraser
George Fraser
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Studied Mathematics at Arapahoe High School
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10mo
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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 t… (more)
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Cdmelanie
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Jun 12
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How does cross-dressing feel?
after failing miserably trying to be a man for 40 years then having my
ex wife tell me I'd be better off becoming a woman cause I never was a
real man nor would I ever be a real man and hearing her tell me she was
leaving behind all her lingerie for me to see how right she was. I
decided what have I got to lose, maybe she is right. it turned out she
was right, I looked amazing dressed as a woman. the feel of the soft
silk clinging to my body, the teddy fit my body perfectly, the silk
thong hugging my tiny manhood and my firm round butt cheeks exposed I
felt so attractive and sexy.

I felt so nat… (more)
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Whisky Jack
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Like to be humiliated by girls watching me be a sissy slut
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May 21
When I am caught or seen by a woman while I am getting face fucked, my
ass pounded, or spitroasted (best option) I get extremely excited a have multiple sissygasms. It is what sexually excites me the most!
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Kristina
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Lifelong Crossdresser and incest lover
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May 14
Plenty of times, it is about the only way I can cum now. I start
dripping once the cock enters me and if he does me long enough I can
even have multiple orgasms.
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Jessica
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Knows Swedish
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Jul 1
yeeees ! whole the time !! ;D mostly if i get doggyed
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Sky High
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Crossdresser from early teen to old coot
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Jun 26
More like after taking off my women's clothing…

I've had bottom sex with men a number of times, and though I don't get
hard when in drag, I came a couple times. A slow trickle as opposed to a squirter.

Now bear in mind that receiving anal sex is a guaranteed orgasm, so
after a while you don't worry much about cuming from the front.

When crossdressed in public I was very self conscious about not showing
an erection, much less a cream stain, so I took great care of tucking
and wearing clothes with a bit of give in the front.
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Daphanie Allison
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1y
Not yet but it is on my bucket list. Mmmmm👗🔥❤
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Randilynn Cook
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decorater, sonographer, tease
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Feb 24
Mhuh, just yesterday I ga

ve a man a blowjob in my car and as I was sucking his nice 8inch cock I
creamed in my panties 💋
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Paul Carter
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Retired Carpenter
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Mar 5
Yes . I was sitting on my big dildo. It filled me up. As it bottomed
out. I came all over my self
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Bothwell
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10mo
Every time I dress. CW
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Alma Mia
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Electronics Technician
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Apr 12
Yes he got a huge cock so big I can't wait to satisfy him alot until he
fit it inside and he makes me feel very pretty and sexy he almost rip
off my tender pussy deeper I was sweating like hell thinking he broke my
pussy apart hard to satisfy this guy he make me suffer alot
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Tyler
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B.A. in Sociology & Anthropology, The University of Texas at Austin
(Graduated 2008)
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Mar 21
I’ve had two. Both times were while I was being throat fucked while a
guy rimmed my ass pussy.
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Larry Latta
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Love feeling feminine
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1y
No not yet but willing to try
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Larry A Nelson
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Former Freelance Adventurer and Blogger
·
1y
I’m not sure that I ever had a “sissy” gasm because I always felt like a horney boy even when putting on a pair of panties.
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Assleah
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Lives in 91767 (2015–present)Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
1y
Related
Have you ever cross-dressed with another male?
Yes, I have had two different crossdressers visit my place for some
dressing and play time. I have also visited an online friends hotel room
a couple of times for play dates and fun. All in all we had a great time.


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



… (more)
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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
Related
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 … (more)
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Elizabeth.W
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Sissy, Crossdresser, ROANYER Brand AmbassadorUpvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
Jan 31
Related
What do you crossdress like, being on top or bottom?
I like being the dominant one so I prefer top. You can tell by the
clothes I love wearing. ;)


… (more)
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Maria Iam
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I finally started HRTUpvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years and
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
1y
Related
Have you ever cross-dressed with another male?
No, but I'd love to try sometime.


… (more)
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Lisa Brown
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Former Self-employedUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020) and
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
1y
Related
Who many crossdressers like to be treated like a cumslut while dressed?
That's the whole point for me. Being the center of attention and having
men lust after you and be willing to service them!



… (more)
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RAZORHEELS
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Studied Adult Education (Graduated 1994)
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Mar 26
Related
What do you crossdress like, being on top or bottom?
I am a Dominate Crossdresser and my very sexual Gurls love the way I
control the Sexual Adventure. Pleasure is never one sided there are Psychological, Emotional and Physical experiences. Often I give my Gurls
what they want—spanking, a little leather to warm their ass, cuffed,
tied or blindfolded and more. As a Dominate my Gurls enjoy the fact that
I am concerned about the twisted pleasure and safety. Gurls love the way
I pamper and stroke their ass. They just loved being Fucked like a woman.


… (more)
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Lacey Femme
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20 years dressing upUpvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
7mo
Related
Who are cross-dressers, and what are your experiences when dressed?
I'm an older man who became very curious about crossdressing in my 20’s,
and did so frequently for most of my 30’s and 40’s. I never did so full time or very openly on account of conflicts with work and shared custody
of the kids from my first marriage. I am not trans, but always feel very
girly and sexually attracted to men when crossdressed. I’ve had
something like 100–150 casual partners over the years, most of them anonymous. I feel this is my true identity, and only regret not starting
sooner and missing the opportunity to crossdress full-time. Here are two pictures from some time ago.



… (more)
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Kristen Swallows
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I am a crossdresser. Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
Jul 19
Related
Do you enjoy being cream pied as a crossdresser?
Yes, I love it. I also enjoy licking his dick clean when he pulls it out.


… (more)
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Emma Wylde
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Lives in Leeds, West Yorkshire, UK (2014–present)Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
1y
Related
How did it feel when you first fully cross-dressed?
my transition to becoming a full crossdresser wasnt immediate it took
some time kind of an evolution.

it started out into fetish and goth look ,pvc leggings and matching
jackets. i had the idea of trying on some high heels with my pvc
outfit,i was surprised how they lifted my butt and gave my legs a
feminine shape.

i always did weights and squatting so i was naturaly in good shape
anyway but wow what those heels did to me,it got my curiosity going so
my next step was to buy a long dark wig.

i gathered all my feminine outfit and dressed in the bedroom full length mirror,i was so surprised how femi… (more)
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Evian Angelique
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Working Girl at Mistresses Incorporated (2020–present)
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4y
Related
Has a woman ever approached you while you cross-dressed, and what happened? Well yes they most certainly have. When I go out, I I prefer to go out
to straight bars, and I always find lovely ladies to chat with and hang
out with.. I totally adore women and look up to them, that is why I
crossdress in the first place. I have a number of women who are my
girlfriends that I like to go out with have cocktails with or just hang
out with depending on what mood we are in. One of my funnest times
meeting someone was the first time I got to hang out with my friend
Brandy. We did not actually meet in a bar but instead I met her on
editing line called lava links. I told her crazy… (more)
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Lacey Femme
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20 years dressing up
·
9mo
Related
How was your first time to satisfy a man as a crossdresser?
I was in my late 30s and pretty nervous about crossdressing in public,
so I was still in a phase of visiting adult theaters wearing a full
lingerie outfit under pants and a jacket, and then taking them off once
I got inside. After several visits I worked up the courage to approach
men who were stroking and visibly hard. I would first sit down two seats
away, make eye contact, move next to them, rub their leg, then their
cock, and finally kneel down between their legs and start sucking. The
process is designed to let either party decline without too much
embarrassment, but I think it was probab… (more)
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Valerie Lake,cd
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I've been wearing female clothing for 5 plus years. Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
7mo
Related
Who are cross-dressers, and what are your experiences when dressed?
I've been dressing for many years now. I have always felt more feminine
than masculine. I love all of the soft fabrics, styles and colors. I
work a outdoor job, very masculine type job, wear bra,panties, and
nylons under my male clothes. I'm married and my wife knows and approves
of my dressing. I love being able to wear something more feminine after
work. I don't think that clothes should be male/female. Why can't anyone
wear what they are comfortable with.



… (more)
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T R
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Impulse CL-CDer 40 years. Worn nylons since 10 yrs old.Upvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
1y
Related
When was the very first time you cross-dressed, and did you like it?
The first time I crossed dressed I was 10 years old and had been at home
by myself and went into my grandmother's sewing room where I found a box
with a dress and nylons. I put these on and a pair of her Black Kittens
and wow that was exciting got a major hard on. I might have dressed
again but don't think i did but wish I could've. Didn't start wearing
dresses till 1992 after getting out of the Army. Found this dress below
being given away by my stepmother and took it. Still have till this day
and current picture.


Below newer.




… (more)
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Jasmine Naneoyerbiznis
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Male, Straight, Married, and often wearing a pretty dress!Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020) and
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
8mo
Related
Have you went any further than panties? Have you ever cross-dressed all
the way?
So many times, but over 2023, I’ve gone from quietly dressing at home,
to the stage where I’ve been shopping on Princes Street and in Edinburgh
in the early evening. My next challenge is to find a quietish bar to go
for a drink with my Mrs while I’m dressed as Jasmine.

My wife took this photo of me while we were out one evening …


… (more)
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Kendra
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Have had sex multiple times at a adult theater
·
May 4
Related
What is your experience cross-dressing while spun?
I do love getting spun before I go out looking for men I get spun out of
my mind and I become more freer than if I wasn't spun it let's me do
things that I would normally would need to think about before I do them
so getting spun out helps me become the sissy cumslut I want to be and I
love it when a man irt a group of men take advantage of me using my body
as there sex toy to be used for there desires and sexual release I love
all of the intention I get when I dress up slutty with no panties on and
bend over in front of a man or a group of.men and letting them have
their way gropping me and f… (more)
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Nickita Borgia
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I love cross dressingUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
Updated 1y
Related
When was the very first time you cross-dressed, and did you like it?
I started to try feminine clothing when I was 10, but I never really
fully dressed up as girl until I was 14 including make up and escape at
nights and walk around the neighborhood all dressed! I loved it!🥰☺️💜🏳️‍⚧️⚧🏳️‍⚧️😋





… (more)
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Daphanie Allison
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Studied MTF Crossdresser & Sissy Fetish at Fiona Dobsons Crossdressing Blog
·
8mo
Related
Have you went any further than panties? Have you ever cross-dressed all
the way?
Yes, it started out with panties, then I added a bra. Thigh high
stockings came next. That's all I did for years until 2020. I bought my
first wig and acquired my first dress. I bought some cheap makeup at the
dollar store to practice with. Now I'm proud to say that I dress
completely feminine from head to toe and I love it❤.




… (more)
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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 years
·
9mo
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 mén… (more)
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Maria Iam
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I finally started HRT
·
1y
Related
How did it feel when you first fully cross-dressed?
Heavenly. I thought I would look ridiculous with makeup and a wig, my expectations were set low. My very good friend did my makeup and I
borrowed her skirt and a top. The transformation was amazing as it
happened right before my eyes. As each layer of makeup was applied, I
could see the feminine side of me come out even more. Then came the wig,
and bam. I stood in front of the mirror admiring myself. Playing with my
long hair, doing different poses. I slipped on my heels and must have
walked around the hotel room for an hour, enjoying each and every
feminine sensation I could. The feeling of m… (more)
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Velia T
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Upvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
1y
Related
Who many crossdressers like to be treated like a cumslut while dressed?
I love to read sexy comments when I am dressed like that


… (more)
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Johanna's Life Change
·
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Dress loverUpvoted by
Gregory Emmerling
, Love crossdressing and have been for over 40 years
·
Aug 9
Related
Has a female that you are close to ever seen you cross-dressed?
Awwwwe my bestie I remember the first time I told her. “ No Way”!! Was
her first response, and I asked her if she'd like to see”? “ Of course I do” and I sent her a picture . She asked me if I had any clothes and I
told her , “ just a skirt and a couple tops”. In less than an hour. “Get your but out here” . I went to my front door and there was a huge bag
full of things. She giggled and told me to have fun. Omg I was in
heaven. I ordered a wig and a pair of heels snatched some makeup. Put everything on . And when she came home on her lunch break I walked out
the front door, down our driveway t… (more)
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Jennie
·
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Former Aso EmployeeUpvoted by
Wendy Hand
, former Crossdresser at Cross-Dressing (1971-2020)
·
1y
Related
Have you ever cross-dressed with another male?
Yes, I have same esperience.

As a trans woman, I have already know some people who are crossdressing
men. Actually, I know most of them from trans & crossdressing dating
sites. Yes, I help two crossdressing guys to dress up.

I know them online and one of them is a lawyer. He told me when he
dressed up, he could release his burden at that time. This was a good
way for him to get away from stress. I took him to a friend’s clothes
shop and he seemed to have a great time. And we had a great time on that
day.

And another guy is a student. He told me no one knew his secret and I
was the first person to… (more)
14 answers collapsed (Why?)
Related questions
Do you enjoy being cream pied as a crossdresser?
Are you a gorgeous crossdresser?
Have you had a surprising experience when you were caught crossdressing?
What are some cross-dressing confessions?
How many crossdressers with a brother ever let him touch you while you
are dressed up?
As a crossdresser, have you ever been picked up?
Does your mom cross-dress with you?
Who many crossdressers like to be treated like a cumslut while dressed?
Have crossdressers ever been gangbanged while cross-dressed?
Did somebody make you crossdress?
As a crossdresser, when did you start sleeping with men?
What do you crossdress like, being on top or bottom?

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