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I Would Love to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 796 People

    It Would Be Fun, But ...

    I really want to be the cross-dresser having sex with a real woman.  I have plenty of fantasies about both situations though, although I seriously doubt I'd ever actually do it, but it may be fun to at least dress up. Are there any real women in this group, or just...
    SomeguyinUT SomeguyinUT 31-35 1 Response Jan 19, 2009

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    Cd From Nj Looking For Cd Or Ts <3

    heyy guys, I'm a eighteen year old crossdresser from  northern new jersey and im looking for another crossdresser to have fun with. Im six foot one with blue eyes and a blond wig, i wear glasses, favorite outfit is a little black mini dress with lots of straps and some...
    xdressingXOXO xdressingXOXO 18-21 1 Response Apr 10, 2011

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    I Love Sex With Cross-dressers!

    I've been a trannie all my life and I've found others a turn-on since I was a teenager. I find it incredibly horny, men dressed and made up as women. I love to take another TV in my arms and kiss her, feeling her hard maleness against mine. I love sliding my hands up her thigh...
    BiTvDeeUK BiTvDeeUK 56-60, T Feb 16, 2010

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    First Time Sex With A Crossdresser

    My girlfriend is very hot and lives with me. She had to leave town for a week on business and so I went on craigslist for fun one night just to look at pics and **********. I always watch shemale or TS **** but never actually did one before up until that night. I msg'd a pre op...
    bontera212 bontera212 31-35, M Sep 14, 2013

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    How I Become A Crossdresser

    Three years before there was a girl named Jasmine near my home. We became friend. She is very beautiful. She was not tall and not short. she was slim with nice boob. One day I date with her. she explains how girl get feel during sex. She told girl are blessed. She told giving...
    deleted deleted 26-30 Jul 7, 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 4 Responses Jul 23, 2010

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    My Friend's Wife Asked Me To Have Sex With Her Husband

    I have a friend that is bi sexual and a real sexy tranny. I had an interesting evening with both of them a while back where he was all dressed up as sexy as any hot woman. That night I found myself wanting to have sex with him again but did not want to go around his wife to get...
    hhstalegs hhstalegs 51-55, M 11 Responses Sep 25, 2011

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    Lesbian Encounter With A Plus

    How hot would it be... two crossdressers enjoying an afternoon, evening and night together, spending time as girls would and then being able to enjoy that long and hard something extra ;-)
    SexyTiffanyCD SexyTiffanyCD 41-45, M 1 Response Aug 3, 2013

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    This Is My Goal

    I'm curious and I if I was to suck a **** it would be attached to a Tranny, Shemale or  attractive Crossdresser If I was to meet an attractive Crossdresser in southern Arizona, well............................the idea of sucking a nice **** turns me on. I think that first...
    stevejohns stevejohns 51-55, M Feb 25, 2010

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    Love Panties

    would love to see other guy in panties and lingerie and be his lesbian lover two sexy ******* we could have loads of fun something i would love to try have fun with another cross dresser
    markonek markonek 41-45, M Sep 27, 2009

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    My Fantasy Of Being With You.

    I stand on your doorstep in a sexy black dress and heels with my nails (both fingers and toes) painted a cute shade of pink.  I stand there, nervous, hoping you're as pretty as your picture and that you find me as pretty as mine. When you open the door, my jaw drops. ...
    phoenix11664 phoenix11664 31-35, T 15 Responses May 31, 2010

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    Want Relationship

    I read about and think about having a relationship with another crossdresser. I have never allowed it to happen and am sorry that when I did have the chance I did not.There are so many that say they want to have a relationship/sex that now I hope to hear from someone. Perhaps I...
    jansmith jansmith 51-55, M 1 Response Jan 20, 2010

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    I Want Love

    i would love to have an affair with a crossdresser like myself. some one who is gentile and kind. i love to dress in undies and stockings and a little makeup. and lots of perfume. i live by myself so no problems in getting together. lots of love. toni
    kellydog1 kellydog1 61-65 Dec 13, 2012

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    A Crossdresser's Fantasy

    I've been crossdressing for years now and I have to admit that I have come to fantasize about being with a man while dressed. I've had meetings with men but never have I actually been penetrated by a man. I think that would be very hot - but I would have to be totally dressed. I...
    hosegirl hosegirl 31-35 3 Responses Feb 3, 2010

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    Add A Real Crossdresser

    :) venom_underground@hotmail.co.uk   talk and get to know me please :)    x
    darknothing darknothing 18-21 Apr 26, 2010

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    I Like Dressing

    i would like to hear from those who would like to have sex with me while I am dressed as a woman.
    NewTGurl NewTGurl 41-45, T 5 Responses Jan 26, 2012

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    Crossdressing Halloween Surprize

    I had been invited to a halloween party at some friends of mine home, I decided to just drop by for a minute then leave. When I got there I noted that one couple was crossdessed, she was dressed as a man and he was dressed as a slutty woman. I found myself drawn to him so I went...
    hhstalegs hhstalegs 51-55, M 13 Responses Nov 7, 2011

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    I Always Wanted To Have Sex With A Crossdresser, And One Day, I Did.......

    ......... I was in Perth, Western Australia, on business, staying at the Trade Winds Hotel. I'd worked that Saturday morning, and had gone for a drive to Rockingham for the afternoon. When I got back, I went to the house bar for an hour after dinner. I'd only been in there 10...
    kiwicd kiwicd 56-60, M 2 Responses Mar 31, 2011

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    Lookin For Another In Conn.

    If you in lower Fairfield County, CT. You can host. Let me know I would love to have some dress up fun.
    Galahad727 Galahad727 56-60, M 5 Responses Oct 23, 2013

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    Clubbing

    Like to go clubbing would love to pick up on a lady take her home slide my hand up her thighs and find a**** what a turn on then make love to her.
    maninagarterbelt maninagarterbelt 41-45, M 4 Responses Jul 28, 2009

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    Cd In Lexington Kentucky Who'd Love To Meet Someone Who Wouldlove To Have Sex With A Cd

      I'm a Cd livinging in Lexington Ky who wouldlove to meet guys that wouldlike to have sex. Send me a message on this ir through yahoo mail at tashakentky.
    tashakentky tashakentky 31-35, M 1 Response Jan 5, 2013

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    I Have Been Wanting To Try....

    I have been wearing panties every day for a little over two years. I wear them all day but take them off before I go to bed so my wife won't find out. I have been reading several stories here on EP and have really enjoyed them. My first experience with women's panties was when I...
    nylon48 nylon48 46-50, M Jan 16, 2011

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    Naughty Time While Dressed

    As a new husband, I went along with my wife and played at crossdressing. As it was exciting and fun, I didn't mind. Little by little, my wife kept up the game. I was getting sex so I played along. One day, I came home to find I had no male underwear, just panties, camisoles, bras...
    pantiescouple pantiescouple 26-30 3 Responses Jul 19, 2010

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    Nikki And I At The Beach

    When I lived in North Carolina I had met a gorgeous crossdresser named Nikki online. The following story is about one of the times we went to Atlantic Beach. Nikki is a very petite gurl, standing about 5'4" and 100lbs. She's got a soft face, green eyes, shoulder-length auburn...
    usmcdude usmcdude 22-25, M 3 Responses Oct 10, 2011

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    Caught My Friend Crossdressing And What Happened Later

    I was on a bussness trip with coworkers and the hotel we where staying at shared a bathroom per two rooms. One of my coworkers is kind of afriend to me, he is no longer married and seems alittle on the Bi side but never really said anything to anyone. He sometimes acts alittle...
    hhstalegs hhstalegs 51-55, M 5 Responses Aug 22, 2011

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    Sexy Cd

    I have friends that crossdress. just dont know how to go abouts to sweep one into my bed.. never made it with one. maybe as time goes on I might..
    daysleeper2 daysleeper2 51-55, M 2 Responses Sep 23, 2012

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    I'm Greedy I Want Two

    My wildest desire is to be dressed entirely as a woman and meet two other crossdresser’s. We would start the evening with a bit of smooching before moving on to some heavy petting. One would then take me from behind while I gave the other a *******. We would swap positions and...
    pippacd pippacd 61-65, T 2 Responses Nov 17, 2010

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    Cross Dressing Human Barbie Doll On Skype

    Anyone that would like to sit me down on skype and tell me wat to put on and when to undress and redress and maybe a little more message me for my skype name
    Victoriacutiepie Victoriacutiepie 18-21, T 1 Response Aug 5, 2012

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    Lingerie CD in Williston is looking

    for new friends who also WEAR LINGERIE. NO "men" only girls n gurls. KEY WORDS: Minot Dickinson Sidney Glendive Eastern Montana Montana Dakota North Dakota ND Bismarck
    susancd4f susancd4f 46-50, M 3 Responses Dec 23, 2013

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    The Gurl I Met On I-85

    I was traveling south of Richmond on I-85 just before sun set, when I noticed that the car in front of me suddenly had a massive tire blow out. The car shifted hard and slide off the road. I stopped to see if the driver was OK and to offer any assistance. The driver seamed a...
    hhstalegs hhstalegs 51-55, M 16 Responses Aug 10, 2012

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    Girdle And Nylon Sex

    would love to have sex w/ another CD in our girdles, stockings and sheer slips
    sweetGigi sweetGigi 61-65 2 Responses Oct 25, 2009

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    East central Illinois here

    and would like to meet with another CD for fun
    uncut67 uncut67 56-60, M 4 days ago

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    I Secretly Think of Sucking a Woman's ****

     I secretly think of going out in public with what seems to be a woman, then later finding out that she is not really a woman! I would be kissing her and then discover a hard ****. I would suck it and then make her blow the load in my ***.
    PLUGME PLUGME 22-25, M 4 Responses May 14, 2009

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    Why I Crossdress

    My earliest memory in life is that of trying on my mothers high heels. Most little boys try this a time or two and then go on to something else but for me it was a great big wobbling step towards who I am today. I remember that my father was absent from my life most of the time...
    sissyribbons sissyribbons 36-40, T 4 Responses Dec 22, 2008

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    Sex With A Crossdresser

    I feel it is perfectly natural to want to have sex with another crossdresser,a man or a women. It depends on what sexual needs are at the time. My first choice would be with a young man with a pretty body dressed from head to toe in beautiful silk,satin and lace. I love the idea...
    jansmith jansmith 51-55, M 1 Response Dec 8, 2009

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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 5 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
    Dloveski Dloveski 36-40, M 2 Responses Jul 5

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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 Jul 22

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    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 9 Responses Jul 17

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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 4 Responses 5 days ago

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    I really want to have crazy sex with my sister
    hornyharry123 hornyharry123 22-25, M 1 Response 2 days 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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    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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    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 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 1 Response 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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    I'm 16 and love older men!
    primadonna1 primadonna1 16-17, F 8 Responses Jul 13

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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 1 Response 2 days ago

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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
    Dloveski Dloveski 36-40, M 2 Responses Jul 19

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

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