Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Want to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 274 People

    Sort of

    Mostly, I want to be the crossdresser having sex.  I sort of would maybe be interested in messing around with a crossdresser, but I'm not sure yet.  That's why this is a goal for me and not a group.
    SomeguyinUT SomeguyinUT 31-35 4 Responses Oct 22, 2008

    Your Response

    Cancel

    With Either One Of Us Or Both Dressed.

    I already know that I like sucking **** when I am dressed as a woman. I also know that I'm not really attracted to men. But if one or the other of us is pretending to be a woman, the whole scene changes. I really like the idea of sex with a "woman" with a **** or of being the...
    RayanneA RayanneA 56-60, M 1 Response Apr 11, 2012

    Your Response

    Cancel

    My First Time With A C.d.

    When I first met Debbie, she was dressed in full feminine attire, a black minidress, silk stockings with a suspender belt, and heels. She is curvy and beautiful and easily passes for a girl until you speak to her, when her slightly husky voice seems to give the game away. Those...
    jamiesissycd jamiesissycd 61-65, M 2 Responses Apr 7, 2012

    Your Response

    Cancel

    Cross-dressers Are Sexy:

    I love to see pics of great looking cross-dressers, I think they are sexy as hell. It is one of my fantasies to have sex with a beautiful cd who is all made up with long hair, and eye make-up, and lip stick. Black fishnet thigh highs, garter belt and sheer black bikini panties. I...
    deleted deleted 26-30 Dec 25, 2012

    Your Response

    Cancel

    Yes I Do!

    I want to meet an attractive Crossdresser in southern Arizona, Simple as that. I'm curious and I if I was to suck a **** it would be attached to a Tranny, Shemale or  attractive Crossdresser  
    stevejohns stevejohns 51-55, M 2 Responses Feb 25, 2010

    Your Response

    Cancel

    Washing Dishes

    Last night while my wife was out with the girls I had the house all to myself and decided it was time to let Jessica out to play a little bit. I had a sink full of dishes to do and figured why not bring Jessica out to do them, it would make it more enjoyable. So I went upstairs...
    JESSICAKNIGHT JESSICAKNIGHT 51-55, T Jul 15, 2010

    Your Response

    Cancel

    .......girdle Games

    My date would arrive in the evening and have ''her'' clothes with her. A short visit and then time to dress up. I wait patiently while my date dons her sexy attire. For me it is the clothing as much as the person that I find attractive. The open bottom girdle will enhance...
    deleted deleted 26-30 Apr 22, 2012

    Your Response

    Cancel

    What I Want

    I want to be forced to have sex with another mtf crossdresser.That would be SO HOT!
    jwpalerider jwpalerider 41-45, M Sep 21, 2012

    Your Response

    Cancel

    Second Time With A Cd

    The second CD I was with was in Las Vegas, I met her on an online chat room. I met her at her house and kissed her at the font door. We had a few drinks and sat on the couch kissing and cuddling for hours. Then she led me to her bedroom. She showed me her panties and lingerie she...
    jamiesissycd jamiesissycd 61-65, M 5 Responses May 31, 2012

    Your Response

    Cancel

    Being Made Love To As A Crossdresser

     I love getting all dressed up and wearing sexy clothes. I love nylons and heels.mmmMy friend crossdresser and I have a dream to pick up 2 georgeous looking guy's and getting ****** all night by them. The fun begins the next morning when we share our night in detail and make...
    Louise57 Louise57 56-60, M Nov 8, 2009

    Your Response

    Cancel

    Sex

    Really would like to dress up in lingerie and a dress and have someone just use me. Make me kiss them all over and pleasure them.
    der12333 der12333 36-40, M 10 Responses Aug 27, 2009

    Your Response

    Cancel

    In Need Of

    I want to have sex with a cross dresser & to let them have my virgin man *****
    xdpaul xdpaul 56-60, M Jul 7, 2012

    Your Response

    Cancel

    I Want To Have Sex With Another Crossdresser

    My horniest fantasy is to have hot 69 sex while both dressed in pantyhose. Licking and sucking through the flimsy nylon, and then with our heads inside each other´s pantyhose and sucking each other to a simultaneous ******. Swallowing all the sweet creamy ***** while surrounded...
    Jonim2009 Jonim2009 51-55, M 2 Responses Oct 31, 2010

    Your Response

    Cancel

    Curious & They're Hot

    I want to just been one over and shove my d**k right into one. I would like to meet one in Texas, they are some of most beautiful creatures I've ever seen. If any CD wanna text me or give me advice it would help. I would really line to chat with one.
    lebron2rings lebron2rings 18-21, M 2 Responses Jul 15, 2013

    Your Response

    Cancel

    I Love Having Sex With Crossdresser's

    Hi Wendy here I've been having sex rwith other CD for a few years , and I fine sliding my mouth down a nice thick big **** very execiting, I do beep throat as i love to feel the **** down my throat and suck all the *** out of them have, had 2 **** in my mouth at once...
    wendysmith46 wendysmith46 51-55, T 2 Responses Feb 24, 2010

    Your Response

    Cancel

    A Day In Pantyhose

    It has been many years that Jessica has been suppressed. She went away to save a marriage and rid herself of all her femme clothes, pics, mags, make up, wigs, and toys. I cannot say why, but this year she is fighting to come out again. Wife does not approve or encourage, and...
    JESSICAKNIGHT JESSICAKNIGHT 51-55, T Jul 23, 2010

    Your Response

    Cancel

    Another Crossdresser And Wife

    My wife knows my fetish for crossdressing. She's loved it since I first told her. One night, she came home and told me she had a surprise for me. She brought home another crossdresser and said she wanted to watch. My wife's new friend sat down. He was wearing sexy dark pantyhose...
    pantiescouple pantiescouple 26-30 3 Responses Jul 20, 2010

    Your Response

    Cancel

    I Want To Have Sex With Another Crossdresser

    To play and have sex with another dressed CD has been a long time fantasy of mine. Dressing and undressing each other, and most of all rubbing those hard bulges in our panties together!! I get hard everytime I even think about it. I would love to have sex with other...
    jamiesissycd jamiesissycd 61-65, M 1 Response Jul 10, 2012

    Your Response

    Cancel

    Meeting

    I would love to meet someone who is not passable like me that loves to wear satin panties, bras, hose, heels, skirts, and do each others make up, and lounge around and give each other lingerie shows til we get hot and stroke each other, start to suck each other and explode in...
    size7silkies size7silkies 56-60, M 3 Responses Aug 22, 2011

    Your Response

    Cancel

    My Feelings

    I want to have a full sexual experience with another crossdresser. I have been with them in male mode but never dressed myself. I want to experience the sexual sensations of silk on silk and expressing my sissy side. I want to feel a **** in side me spurting warm *** filling me...
    jamiesissycd jamiesissycd 61-65, M Apr 1, 2012

    Your Response

    Cancel

    Sexual Thrill

    Theres just something about a man in womans clothing and underwear that drives me wild especially when they wear panties i feel like my **** is going to get too big for my pants man i love cross dressers and i really want to **** one :)
    StfComplex StfComplex 18-21, M 1 Response Aug 10, 2012

    Your Response

    Cancel

    Related Experiences

    hi i am from new delhi india i want to have sex with a sexy girl i will pay her gd bt i dnt hv ma prsnal place to **** plz help me out wht to do
    sexyboy034 sexyboy034 18-21, M 1 Response Sep 2

    Your Response

    Cancel
    I want to have sex with a female teacher in my school teaches maths,she's not attached and is only a mere 22 years old she has an a body like an hourglass,all the curves in the...
    TheGamechanger TheGamechanger 18-21, M 3 days ago

    Your Response

    Cancel
    Even though we don't have a label on our relationship, I still want to have sex with him and kiss him and hug him and cuddle . I like the way he feels inside of me . I don't know...
    neuroticgal neuroticgal 22-25, F 3 Responses Sep 14

    Your Response

    Cancel
    I love my dad more than anything and wish I could have sex with him.
    JeremyCooper JeremyCooper 16-17, M 4 Responses 4 days ago

    Your Response

    Cancel
    My girlfriend has been having sex with other guys, about 2 of them she had sex with multiple times
    jma13f jma13f 18-21, M 2 Responses Sep 7

    Your Response

    Cancel
    My ex and I broke up a couple of months ago, and while I don't want him back, there is still something there that makes it hard for me to stay away from him completely. The thing...
    PepperF PepperF 22-25, F 3 Responses Sep 9

    Your Response

    Cancel
    Godd its a big big want of mine , i just cant tell you how often i think about it and want it ...
    Yungbug Yungbug 18-21, F 2 Responses a week ago

    Your Response

    Cancel
    It happened, and I want to go into detail about it, but how can I do that without getting flagged? Can I type it up on another document and put the link up?
    teentwink teentwink 18-21, M 2 Responses 18 hrs ago

    Your Response

    Cancel
    Or cyber with :) the older the Better come and get me
    Happiness412 Happiness412 18-21, F 5 Responses Aug 27

    Your Response

    Cancel
    I have. It was awesome she was blonde
    lotsoflove12 lotsoflove12 31-35, M Aug 31

    Your Response

    Cancel
    I want to suck a guy. I love the thought of having a guy in my mouth. Would also like to bottom for the correct guy.
    MITUK MITUK 36-40, M 3 Responses Sep 9

    Your Response

    Cancel
    I have a deal for yu if yu willing to listen go read my experiences plz and inbox me serious ppl onli!!!
    ih8beingyung ih8beingyung 18-21, F 2 Responses a week ago

    Your Response

    Cancel
    Mmmm with a fat **** yummy
    lostgirlbree lostgirlbree 22-25, F 1 Response a week ago

    Your Response

    Cancel
    I am so horny and want to have s e x with older man like 40's-60's. ;)
    Elizabeth214444 Elizabeth214444 22-25, F 2 Responses 4 days ago

    Your Response

    Cancel
    I'm going home today from college to spend time with my dad. Hopefully something will happen. Will update.
    teentwink teentwink 18-21, M 2 Responses 1 day ago

    Your Response

    Cancel
    A older guy.. Better or worse??
    BeauteFloue BeauteFloue 22-25, F 3 Responses Aug 28

    Your Response

    Cancel
    I live in Michigan and looking for some fun if there is any out there let me know
    Gunnera87 Gunnera87 26-30, M Aug 28

    Your Response

    Cancel
    I mean I'm black Too So why not 😩🙌you know black guyssss got that big ____
    MisMisMis321 MisMisMis321 16-17, F Aug 30

    Your Response

    Cancel
    My dad is hot. I like it when he touches me.
    gayandproud13 gayandproud13 13-15, M 7 Responses Aug 31

    Your Response

    Cancel
    It was a sleepover, he crawled into my bed. He got on top
    lotsoflove12 lotsoflove12 31-35, M Aug 31

    Your Response

    Cancel
    Someone message me so horny
    maddieXxx maddieXxx 16-17, F 5 Responses Sep 6

    Your Response

    Cancel
    I'm 16 and I love older men and women 😋
    jhopegirl jhopegirl 22-25, F 1 Response Sep 12

    Your Response

    Cancel
    I hate how ppl who don't know me look at me and think I'm not a virgin...like wtf? And I hate how some people I know always tell me "just do it" "you're too pure" "gotta do it...
    Midnightangelx Midnightangelx 16-17, F 1 Response Sep 13

    Your Response

    Cancel
    I want to have sex with one so bad, like 14-15. (Im 16 btw, it wont let me change it)
    Bimanwhore9 Bimanwhore9 18-21, M 2 Responses 4 days ago

    Your Response

    Cancel
    I have sex with my cousin all the time do you want to hear the stories ? ;)
    Vannnessaaaaa Vannnessaaaaa 18-21, F 29 Responses Sep 7

    Your Response

    Cancel
    Any girls in Birmingham ..I want to have sex with a girl! Btw I love older women
    Babyk31 Babyk31 16-17, F Sep 6

    Your Response

    Cancel
    I am happy to chat with crossdresser, just inbox me and we can talk
    Thecdman Thecdman 22-25, M 5 Responses Sep 12

    Your Response

    Cancel
    I was a virgin on my 18th birthday, graduation day, and on my wedding day too. On my wedding we tied the knot, had a great wedding reception, went to our honeymoon destination...
    heatherinarizona heatherinarizona 31-35, F 3 Responses Aug 25

    Your Response

    Cancel