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I Want to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 266 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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 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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    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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    .......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 1 Response Apr 22, 2012

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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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    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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    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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    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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    Related Experiences

    I bought a lusty Leo fake penis of eBay and have been plowing my hole for a while If I can't have sex with another man physically then I at least want to exchange pics or videos
    lovezadick lovezadick 18-21, M 5 Responses Mar 22

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    I've always wanted to have sex with BBWs. I want to explore the whole body of a woman who is 200+ lbs, and tongue her holes before going in her and pounding her like there's no...
    MoaXing MoaXing 16-17, M 2 Responses Apr 6

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    I want to have sex with her she's 15 and has a great body
    comeatmebruh623 comeatmebruh623 26-30, M 1 Response 3 days ago

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    I like to meet up with strange men off line and have sex with them
    caliboy7 caliboy7 26-30, M 3 Responses Mar 20

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    I had sex with my husband yesterday! Sad thing we are in the middle of divorcing one another! I was just so desperate for sex... That I asked him for mercy sex... Gosh I hope I...
    just2lovelee just2lovelee 41-45, F 1 Response Apr 11

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    I want to hear stories and see pictures of people having sex with animals!
    Cameltoelove Cameltoelove 22-25, M 2 Responses 3 days ago

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    I want to have se*with my sister. She's 19 and I'm 22. She's tall has a banging body. Nice a$$ and perky t:ts. I constantly think a About asking her to have se* when we are home...
    Libbey91 Libbey91 22-25, M 2 Responses Mar 26

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    Like, it's on my bucket list! I find it interesting and sexy.
    ReeseThompson0424 ReeseThompson0424 18-21, F 2 days ago

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    been married for ever I think she has sex more with other people than me I know she cheats im ready for affair
    crazyaboutit123 crazyaboutit123 41-45, M 1 Response Mar 21

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    I just really want to suck one, I don't know why.
    MakeMeKing MakeMeKing 22-25, M 4 Responses Mar 30

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    Recently I discovered that I enjoy her relationship with other men. I even want to see her have intimate relationship with them. This I realized when I saw her sharing some adult...
    rimpi1972 rimpi1972 41-45, M 5 Responses Apr 8

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    AgeMeet.com, a website specifically designed for older man younger woman relationships and older woman younger man relationships. AgeMeet.com is the world's first, largest and most...
    fionacc12 fionacc12 26-30, F 1 Response Mar 26

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    I have dated black woman before and it was great . Lately it been impossible to meet black woman
    mruiz252 mruiz252 41-45, M 1 Response Mar 29

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    I love bbw, I have ever since 5th grade. My teacher was a very large black lady with rolls on her thighs. I remember touching myself through my shorts because of the way it made...
    bbwlover30265 bbwlover30265 26-30, M 1 Response Apr 3

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    My wife and I have only fantasized about her sucking another man off as I **** her
    bbking88 bbking88 36-40, M 11 Responses Apr 8

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    Over the road, driver would love to hook up with horny bbw
    DriveHardDave DriveHardDave 51-55, M 5 days ago

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    I find this very intriguing, seems kinda hot and fun...
    92youngforever 92youngforever 18-21, F 1 Response Apr 4

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    Let's make it easy... I tell you about me you tell me about you. I choose the place I pick you up I feed you and then I **** you outside my car, inside my car, at a restaurant, at...
    youguyssuck69 youguyssuck69 18-21, M 1 Response 3 days ago

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    That would be great specially if he about nine inches or so that feel great
    iluvlezgal2 iluvlezgal2 41-45, F 6 Responses Apr 3

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    the reasons why i dont want to do anything sexual before marriage : reason number 1 : what if i had sex with my girl friend before marriage , and after few days i met with...
    lifetriangle lifetriangle 22-25, M 7 Responses 4 days ago

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    My parents struggled with their marriage when I was in high school, after that I realized I wanted a stable, happy relationship, and never wanted to cheat or be cheated on... I saw...
    chiquita55 chiquita55 18-21 Mar 27

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    I am looking for girls to have sex with and it's terrible bc 1 I can't find a girl 2 I live in Cranston and 3 idk I'm at the right place lol
    DaveP13 DaveP13 18-21, M Mar 24

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    I think one complete the other one,cause when you have sex with love it should be the most amazing feeling ever.
    miserableamy miserableamy 16-17, F Mar 25

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    We have been married for 15 years and wanted to see how to have sex and watch sex via a web cam. You have to be sexy, we are! in good shape, and willing to show us how to do it...
    just4fun3 just4fun3 41-45, M 1 Response Mar 27

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    I want a sex change more and more and more than I have ever wanted anything else. I would love to be a woman for the rest of my life and it pains me that I can not be a woman right...
    wtbwoman wtbwoman 41-45 4 Responses Mar 24

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    it's been three weeks i have had no sex, i look for a good man, love me first, then we can have sex, that is what i want to. so hard that to get it??
    tanglelau tanglelau 31-35, F 1 Response Apr 11

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    I have something called "Frenulum Breve" and "Phimosis". having those conditions make it impossible to have sex. Becoming 30 years old this year would make me sort of a 30 year old...
    MAGH2 MAGH2 26-30, M 1 Response 19 hrs ago

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    I have been with 38 men and 2 women and while i enjoy sex with men i always want something more ,i am in a very loving relationship with a wonderful man but i constantly find...
    deleted deleted 26-30 1 Response Mar 21

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    Never had sex with a black woman but I want to.
    andykenny andykenny 26-30, M 1 Response Apr 9

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    Having sex without a condom is wonderfull.....I love the naked feel of a penis inside me!
    noknickersloulou noknickersloulou 22-25, F 35 Responses Mar 22

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    I like having sex with out pertection
    izac31 izac31 18-21, M Mar 31

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    I love sex without protection message me and I will tell you why(;
    Hellogoodbye85 Hellogoodbye85 18-21, F 33 Responses Mar 31

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