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I Would Love to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 885 People

    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
    kelliTxxx kelliTxxx
    36-40, T
    6 Responses Dec 16, 2015

    I would love to find someone

    that wants to have sex with me
    kelliTxxx kelliTxxx
    36-40, T
    4 Responses Dec 22, 2015

    I think it would be fantastic in everyway

    possible to people haveing the same interest in everything it has to be a fantastic experience
    deleted deleted
    26-30
    1 Response Jun 18, 2015

    East central Illinois here

    and would like to meet with another CD for fun
    uncut67 uncut67
    56-60, M
    2 Responses Jul 28, 2014

    I want to feel our nylon covered legs rubbing

    together as we kiss. Our hands exploring each others bodies caressing them and holding each other tight. Your stockings rubbing against my ears as my head finds its way under your dress. ..... and so much more.
    jennloves55 jennloves55
    61-65, M
    1 Response Dec 23, 2015

    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

    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

    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

    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

    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

    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
    3 Responses May 14, 2009

    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..
    deleted deleted
    26-30
    1 Response Sep 23, 2012

    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

    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
    Dec 8, 2009

    Add A Real Crossdresser

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

    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
    2 Responses Aug 5, 2012

    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
    2 Responses Jul 19, 2010

    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

    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
    1 Response Sep 14, 2013

    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
    2 Responses Feb 3, 2010

    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
    3 Responses Jul 28, 2009

    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

    I will dress up as well.

    That would be.amazing
    Bbwluvanh Bbwluvanh
    36-40, M
    3 Responses Jan 1

    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

    That Would Be The Perfect Scenario For This

    Girl,As A Matter Of Fact I Want A Lesbian Relationship With A Female/Sissy Crossdresser.So,ANY Girls In My Area Specifically..Inbox Me
    deleted deleted
    26-30
    Jan 27

    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
    46-50, M
    1 Response Aug 3, 2013

    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
    Jan 5, 2013

    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
    13 Responses May 31, 2010

    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
    1 Response Sep 27, 2009

    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
    2 Responses Dec 23, 2013

    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

    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

    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

    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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