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I Want to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 276 People

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    I want to be with someone

    who wants to be with a CD. I don't want a bf, just someone I can meet from time to time for some fun.
    asiancdcrystal asiancdcrystal 26-30, M 4 Responses Jul 20

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    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 otherĀ“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

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    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

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    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

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    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

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    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

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    .......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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    Related Experiences

    When I was really young there was a teenage girl with dwarfism in my neighborhood that I saw regularly. I don't think I was even old enough to like girls yet but there was...
    thatguythereoverhere thatguythereoverhere 26-30, M 2 Responses Jul 27

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    This year, I had a extremely attractive chemistry teacher. He's sweet, and has vibrant blue eyes, short blonde hair and a perfect body. Every time that I would look at him, I...
    Jeanpocket Jeanpocket 13-15, F 1 Response Jul 22

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    I think i would be great to have sex with a trans women. They are really gorgeous but also independent in a sense. I'm not gay but I definitely want to go for a transvestite woman...
    lolzmeplz lolzmeplz 16-17, M 4 Responses Aug 4

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    I want to have sex with woman while my boyfriend partipates however he wouldn't **** her or lick her. She would lick me while my boyfriend ***** me and I would return the favour to...
    Readingaddict Readingaddict 18-21, F Aug 9

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    I really want to have crazy sex with my sister
    hornyharry123 hornyharry123 22-25, M 5 Responses Jul 30

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    This is something I want to try I have never even dated a black man much less had sex with one but there is a first time of every thing right ??
    1Miserablemind 1Miserablemind 18-21, F 8 Responses Aug 5

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    I'm a sexy black girl from PA ;)
    Rayven1997 Rayven1997 16-17, F 2 Responses Aug 10

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    I just turned 19 & I think it would be so sexy to be with a guy like 30-40. Experience is such a turn on and I bet someone that age would have a lot. That's like my biggest fantasy...
    wayyfarer wayyfarer 18-21, F 17 Responses Jul 26

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    I just think that trans women are so hot. Girl up top but guy down below. I don't know why I just think it's incredibly sexy.
    LadyCNote LadyCNote 26-30, F 3 Responses Jul 31

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    I just need sex to sleep at the moment!
    deklan deklan 31-35, M Aug 10

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    I'm only 19 year old girl, but I would love to have a sexual relationship with a 40-55 year old women and do sexual things with her (or without her) with her teen-age kids (if she...
    Jamielr13 Jamielr13 18-21, F 5 Responses Aug 13

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    Well I owe my father something because he took the blame for something I did once! I think he wants me to blow him but I am not sure! I am bi but he doesn't know! How can I get him...
    jackbx jackbx 13-15, M 1 Response 6 days ago

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    Just want a little chocolate princess! Any takers message me!
    Hazza8989 Hazza8989 22-25, M 1 Response Jul 25

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    I would love to, just need to find a guy who wants it!
    bd693 bd693 18-21, M 2 Responses Aug 8

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    I want a hermaphrodite to **** me xxx
    sassss52 sassss52 22-25, F 1 Response 1 day ago

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    I so badly crave my friends boyfriend he's hot and possessive and dominant and I love everything about him and my friend is a ***** to me anyways and they have only been dating for...
    cootyboo cootyboo 22-25, F 3 Responses Jul 30

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    he's not necessarily attractive or anything. it's just something about his old school, authoritative look that really turns me on. I can just imagine it going like this: me: is...
    fuckinglife fuckinglife 16-17, F 1 Response a week ago

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    Would you go have me boys?
    mommygotboobs mommygotboobs 36-40, F 12 Responses Aug 7

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    My dad is a very straight acting man. VERY. He always walks around the house in his boxers and I can always see he has a bulge poking
    jdragon1704 jdragon1704 16-17, M 3 Responses Jul 25

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    My father is fat and hairy!
    Bulkver Bulkver 36-40, M Aug 13

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    But when I'm a little older, 14 is too young
    bisexuwhale bisexuwhale 13-15, M 1 Response Jul 26

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    the one who came by and talked about where he grew up
    liberty2 liberty2 46-50, F Jul 29

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    Anybody 14 and younger in south fl ;)
    djdicirnndksoxjfdjejx djdicirnndksoxjfdjejx 13-15, M Aug 9

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    My Spanish teacher is sooooo hot and she has the biggest noobs and is so skinny and young! I wanna **** her so bad!
    aidanmcshane6 aidanmcshane6 13-15, M 1 Response a week ago

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    LOFL! I see I'm not the only one.... that guy is good!
    BeyondTheSunset BeyondTheSunset 36-40, F 2 Responses Jul 25

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    We were both youn, started kissing and it almost happened on the floor watching a movie
    avengedwolf88 avengedwolf88 26-30, M 3 Responses Aug 8

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    Would love to have Sex with a pregnant woman would be a great turn on
    Hazza8989 Hazza8989 22-25, M Jul 25

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