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I Want to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 276 People

    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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    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

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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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    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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    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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    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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    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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    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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    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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    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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    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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    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.
    bicuriousasian bicuriousasian 26-30, M 4 Responses Jul 20

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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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    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 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

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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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    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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    .......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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    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 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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    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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    Related Experiences

    Hi my name is Jan I am 21 and have sex with lots of guys. I work at a bar and always bring guys back to my place after work and have sex with them. I have a no condom rule. I want...
    jantheslut jantheslut 18-21, F 8 Responses Jul 17

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    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 1 day ago

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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 6 days ago

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    I would love to have sex with a black women never done it I am so girly right now I will eat eat that p up
    dmedina513 dmedina513 36-40, M 2 Responses Jul 5

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    I have dreams about having sex with my father.
    Bulkver Bulkver 36-40, M 4 Responses Jul 12

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    My dog is the first living thing I've ever had sex with, she was tight, but then I let my friend borrow her and he ripped her a new *******. But moral of the story is, does anyone...
    Guuuu Guuuu 18-21, M 4 Responses Jul 17

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    I have been having sex with my daughters mum for years. I think it's time to stop.
    usernamesareashame usernamesareashame 46-50, M 1 Response Jun 28

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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 3 Responses 1 day ago

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    There's this guy on tinder, he's older, nearly double my age, he's not that hot but decently attractive I'm looking for more guys on tinder but don't know if it would be too bad to...
    hardcoregay hardcoregay 18-21, M Jul 5

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    One thing I want to try is getting ****** while I **** a guy. That sounds mind blowing...
    hardcoregay hardcoregay 18-21, M 1 Response Jul 5

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    I want to suck a guy so badly.
    zacktr zacktr 41-45, M 1 Response Jul 6

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    Not sure if I'm bi or just bi-curious but I've known four guys in my life that if they wanted me to suck them off, I would. How do you bring that up with people that are definitely...
    zacktr zacktr 41-45, M 4 Responses Jul 8

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    I am in high school and this year i really fell in love with my gym teacher and just wanted to have a relationship with him. I just felt i needed someone there to talk to and he...
    soccer2117 soccer2117 16-17, F 1 Response Jul 10

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    Looking for transsexual to **** me I have look every where and I'm so horny for it I just want you now :)
    horny4younow horny4younow 22-25, M Jul 14

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    Want a black girl to talk sx with me I'm so h-rny
    dmedina513 dmedina513 36-40, M 2 Responses Jul 19

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    Want to sx chat with younger girl
    dmedina513 dmedina513 36-40, M 2 Responses Jul 19

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    Just want a little chocolate princess! Any takers message me!
    Hazza8989 Hazza8989 22-25, M 2 days ago

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    i know this is wierd but i want to try this out . and have for a while
    wonderlandwonder21 wonderlandwonder21 16-17, F 1 day ago

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    I ran into a good friend that I haven't seen for several years. He went through a long drawn out divorce and dropped out of sight after that. He hasn't remarried and says he's...
    stillhavingfun123 stillhavingfun123 51-55, M 3 Responses Jul 2

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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 days ago

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    Yeah this could work....hmu
    Sinjintiger Sinjintiger 41-45, M Jul 5

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    I'm 16 and love older men!
    primadonna1 primadonna1 16-17, F 8 Responses Jul 13

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    I wish to try it <3 <3 <3 <3
    confusedbi0 confusedbi0 22-25 Jul 14

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    But when I'm a little older, 14 is too young
    bisexuwhale bisexuwhale 13-15, M 1 Response 2 days ago

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    My ex dumped me and then started seeing some guy just two weeks later. What she doesn't know is one of her best friends has already agreed to screw me, and the other is influenced...
    Warner216 Warner216 18-21, M 3 Responses Jul 1

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    LOFL! I see I'm not the only one.... that guy is good!
    whatyathinkaboutthat whatyathinkaboutthat 36-40, F 3 days ago

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    Okay I live in Michigan and the age to consent to sex is 16 I'm guessing that's with any age but below 16. Anyways this 42 year old police officer who lives in Canada came over the...
    cupcakes38 cupcakes38 18-21, F 3 Responses Jul 19

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