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I Would Love to Have Sex With a Crossdresser

Personal Stories, Advice, and Support 787 People

    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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    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 46-50, M 1 Response Sep 23, 2012

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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 12 Responses Sep 25, 2011

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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 15 Responses Aug 10, 2012

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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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    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 41-45, T Dec 23, 2013

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    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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    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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    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 2 Responses Jul 28, 2009

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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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    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 5 Responses Jul 23, 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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    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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    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 51-55, M Oct 23, 2013

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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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    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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    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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    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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    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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    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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    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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    Love Lingerie

    would love to see another guy in lingerie and be his lesbian friend love wearing so horny when dressed and wife is out
    markonek markonek 41-45, M Sep 27, 2009

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    One Day Soon

    Have met a few people but mostly just bi's. I want the whole nine yards. A lesbian affair between two crossdressers.
    girdlemania girdlemania 56-60, M 3 Responses Sep 23, 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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    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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    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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    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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    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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    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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    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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    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 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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    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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    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

    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 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 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 4 days ago

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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 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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    Over the road, driver would love to hook up with horny bbw
    DriveHardDave DriveHardDave 51-55, M 6 days ago

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    I want to hear stories and see pictures of people having sex with animals!
    Cameltoelove Cameltoelove 22-25, M 3 Responses 5 days ago

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    I have connected with someone there. It is pretty awesome. The chat doesn't have to be "naughty". It is still exciting and creates a spark, to share a chat and a peek at the...
    gmanow gmanow 41-45, M Mar 29

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    I think every chick likes to be with other girls now and then, especially when you're going through an oral sex drought with the boyfriend. I cheated last weekend after some beers...
    Purplesloths Purplesloths 18-21, F 4 Responses Mar 25

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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 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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    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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    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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    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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    Like, it's on my bucket list! I find it interesting and sexy.
    ReeseThompson0424 ReeseThompson0424 18-21, F 3 days ago

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    I probably shouldn't be admitting this, but I need to express it. So mostly everyone that knows me on here knows that I cheated on my fiancé and I've been pretty torn up about...
    rajasaeed rajasaeed 26-30, F 9 Responses Mar 23

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    I would like to get to know you first