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I Want to Have Sex With a Man While Dressed As a Woman

Personal Stories, Advice, and Support 1,819 People

    Again. I've had both oral

    and anal sex with another man while I was dressed as a woman and enjoyed it as much as I have enjoyed anything.
    RayanneA RayanneA 56-60, M 4 Responses Apr 12

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    My Sissy Desires

    For the past 5 years I've been secretly wearing my older sisters clothes. I started of with her panties now I wear short skirts thongs heels dresses and many other things I haven't told anyone except for my grand mother last year because I wanted to try on a girls one piece...
    Marissatgsissy Marissatgsissy 18-21, T 2 Responses Sep 9, 2012

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    Love It

    My first time with a man was at the age of 14 I have always liked to dress with my mom's clothe. One night I was wearing a lace thong and a white lace push up bra and a pink dress blonde wig There was some people over at the house I was just in my room alone. A friend of my moms...
    deleted deleted 26-30 1 Response Feb 11, 2013

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    I Finally Did It

    (This story is 100% true and happened this past sunday) I finally worked up the courage to have sex with another man, I was not dressed up though but plan on it next time, it was a great experience I felt so feminine as he lubed me up and bent me over the bed, I made sure to use...
    tristiny tristiny 22-25, T 2 Responses Jan 8, 2013

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    My First Time

    With my ever growing transvestic fetish it was a natural progression for me to reach the stage where I needed to be with a man. When you are getting ready to go out to a TG or fetish club it gives the whole thing a hot new perspective when you are dressing to seduce a guy. At one...
    territgirl territgirl 51-55, T 5 Responses Nov 23, 2012

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    I Want It

    I want to dress in a red dress suntan pantyhose red heels with a blonde wig and red lipstick and meet a guy most likely at a hotel room. He'll tell me how hot I lookd and then start kissing me. I'll kiss him back and then he'll slip is tongue into my mouth and I'll do the same...
    mc1645 mc1645 18-21, M 12 Responses Jul 13, 2011

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    Best Friend Page 2

    Tom and I had been meeting weekly for over a month now and that Wednesday morning he pulled in the driveway I had both the coffee and my lingerie on. He came into the kitchen, set his briefcase down, looked at me and just shook his head.  "We gotta go for a drive, dress and get...
    jamie64 jamie64 61-65, M 2 Responses Aug 23, 2012

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    Best Friend

    I invited Tom over to plan for a fishing trip we were taking next weekend at a remote lake in the country. I had ordered pizza and we were drinking beer with maps spread out and making lists for food and supplies yet to buy.  With the planning done and the table cleared he...
    jamie64 jamie64 61-65, M 4 Responses Aug 22, 2012

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    I Would Love To Have A Romantic Encounter With A Man....

    I always fantasized of being swept off my feet by a strong man and made love to dressed as a woman. In my fantasy, I am dressed in a nice dress or skirt suit, like this: We meet at a bar and have a few drinks, just so I can loosen up. I know I would be very nervous. While at the...
    christybono christybono 41-45 7 Responses Dec 5, 2010

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    I Had Sex With 2 Men While Dressed In Lingerie

    I finally took the plunge. I had my usual "friend", Kyle, and he had mentioned the possibility of us getting together with one of his friends. I met Kyle and the other man, Steven, at a coffee shop where the three of us could chat. Finally I plucked up the courage, got cleaned up...
    chris1tine chris1tine 41-45, M 11 Responses Aug 2, 2012

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    Man Or Woman.

    Its the only way. It dont matter who you are. Ill only sleep with you if im dressed cuz thats the real me. I like both women and men so both have to accept it. Sex is better for me because i can let go be myself and enjoy it. As a result it tends to be good for my chosen partner...
    Simone1969 Simone1969 41-45, T 1 Response Oct 6, 2013

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    How I Became A Crossdressing **** Sucker

    My how things change. When my wife Lisa and I got married 20 years ago we had a great sex life. The kind most people only dream about. In spite of my good fortune of having such a beautiful and horney wife, I had my share of girlfriends and one night stands in those early years...
    chrissyk48 chrissyk48 46-50, M 6 Responses Dec 2, 2012

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    Soon Hopefully

    I've been talking to a guy online, and he wants to **** me while I'm dressed. I'm excited and nervous. Any advice?
    jjs19 jjs19 18-21 8 Responses Aug 20, 2013

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    Iam A Naughty Girl Now

    Ive always loved dressing as a woman , ive perfected it , for 9 years i would dress up make myself look hot and sexy but never left my appartment. I loved dressing up and I even had a few vibrators and ****** that i would use on myself pretending i was being ****** by a man. I...
    hornydevil2710 hornydevil2710 36-40 2 Responses Jan 5, 2013

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    My Fantasy Come True

    I am worry personified! Never been more worried in my entire life! I've just sucked hic **** you are telling me not to worry! I'm standing, staring, wondering what to do, what you will do with me, or to me - next But suddenly I know I need not worry. You are coming towards me...
    urmila11 urmila11 36-40 2 Responses Sep 9, 2012

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    My First Time

    As a truck driver I stay in motels a few nights every week. I love to play dress up in my room and dress fully and do my makeup and nails. On this day I got to the motel early and showered and layed out my clothes for the evening. I had a red 38b bra with a matching g-string...
    kateylynne kateylynne 41-45, M 11 Responses Sep 22, 2009

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    Cross Dresser Wanting A Man

    I would like to be a man's girl for the evening, seducing him and making him so hot and horny for me. I would get to taste his hard **** before he ****** me hard. I would like to feel his strong hands all over my body especially when he is kneading my *** and stroking my soft...
    ultrasheer2120 ultrasheer2120 46-50 10 Responses Oct 1, 2011

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    Fantasy

    One of my fantasy's since i was abt 12 is that i want to be with another man while i dress up for them i want him to make me feel sexy i would wear anything they would want and let him take my virginity and **** me any way they want to as hard as they want too.. i want to find...
    Scott1331 Scott1331 22-25, M Dec 20, 2012

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    Would Love To Get It On With Other Crossdressers

    I've been wearing women's panties and sexy stockings for years. My friend Alyssa discovered this and took me to the next level. Since that time I have been out fully dressed and ****** hard by her with a strap on. I want to take this to the next level. I WANT THE REAL THING...
    Cantwait2011 Cantwait2011 36-40, M 1 Response Oct 31, 2013

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    A Womanly Desire...

    This would be classified a fantasy but really it's a heart felt desire. I'm sitting on the couch with a date for the night that I found over the internet. We hit it off in the emails that we exchanged before we decided to meet and the desire was there to be with each other...
    ultrasheer2120 ultrasheer2120 46-50 8 Responses Feb 7, 2013

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    Dressed In The Clothes Of My Bf's Wife

    One of my lovers, we'll call him Rick, was married and what used to get him off more than anything else was to have me wear his wife's clothes, especially her panties and bras and lingerie. We would meet at a nice elegant hotel and he would bring a bag full of her things. if i...
    tessa tessa 41-45, T 6 Responses Oct 10, 2010

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    One Early Time

    I was feeling very feminine one night and went to a bar that leaned towards gays and TG I wanted to be more girlyboi that night and was wearing a pretty blouse and slacks that zipped up the sides with low heel sandels. under it I had on a lacy bra and pantie set that made me feel...
    sissiegirl sissiegirl 51-55, T 6 Responses Jul 7, 2010

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    I M Going To Suck My First **** Next Week

    I ve been talking to a guy on line.He wants me to wear my stockings,thong and bra and meet with him.He has been very articulate about what he wants to do to me and I m going to meet him.Any advice from someone with experience?I t really turns me on when he calls me his *****.It...
    wearaskirt wearaskirt 46-50, M 8 Responses Jun 4, 2013

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    Just To See What Its Like

    i have a small collection womens clothing. i wear them occasionally because it relaxes me and turns me on. i do wonder what it would be like to get ****** while i was dressed. part of me is dom while another part of me is sub. oh how i would love to find a guy who is a switch...
    1nakedninja4u 1nakedninja4u 36-40, M 2 Responses Jan 2, 2013

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    Mission Accomplished.....

    I commute an hour one way to work, so there are many times where I stop about half way to see if I can get any action. Most times I stop an exit before the cruizing turnoff and change in a gas station bathroom. I take off my male clothes and put on my stockings and panties and a...
    sissyskoolgurlatgmailcom sissyskoolgurlatgmailcom 46-50 2 Responses Aug 6, 2013

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    My 1st Blow Job

    Although I had been cross-dressing on and off for 40 years, I was nearly 60 before I worked up the courage to suck a man's ****. It had been a secret desire of mine for a long time but the circumstances and opportunities were not there. But, ultimately it was a cross-dressing...
    ConflictSteward ConflictSteward 66-70, T 4 Responses Apr 11, 2013

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    Dressed Fem

    I have had a lot of sex with men dress as a man but deep inside i want to have hot sex as a dressed female to enjoy sex as a woman as i am a bottom and love to please men couples or a woman have always work to please the person i am with before i have any plesure my self
    stephaine71 stephaine71 70+, T 10 Responses Jan 30, 2012

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    Love To Try

    I love to get dressed up in my girlfriend's clothes. I think about sex a lot when I'm dressed and would love to experiment with a guy. I would to have a guy hold me in his arms while we kiss, and feel his hands all over me.
    beth1984 beth1984 26-30, T 9 Responses Nov 13, 2011

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    My Latest Fantasy

    It was a few years ago when I admitted to my wife that I love dressing in women’s clothing. It was after she found a stash of some of my panties. They weren’t her size, so it was an immediate red flag for her. She didn’t immediately believe me. So I gave her an...
    JosetteLaRoc JosetteLaRoc 36-40 3 Responses Jan 7, 2013

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    Make Me Female

    I've once be ****** by a man as I was wearing a skirt. It was not a good experience, too acky!! but I'm ready to try again of course only if I'm the woman. Even He (or her) has to tied me up.
    Sophietrav Sophietrav 51-55, M 10 Responses Feb 17, 2012

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    Fantasize About It

    I have to admit although I have never been with a man I have fantasized about it while dressed feminine. I think it is more about me thinking of myself as a sexy desirable woman than attraction to a man. Which in many cases brings me to fantasizing about being ****** by a she...
    Lori234 Lori234 51-55, M Sep 19, 2013

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    Lingerie For Him

    I love this experience group, it is similar to my fantasy of me shaving my hubbies body helping him with his lingerie doing his nails and make up, and him mine then having a hung stud take his anal virginity and having him filled with ***, i would love for us both to be taken by...
    deleted deleted 26-30 42 Responses Dec 11, 2011

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    My First Time!

    The first man I ever played with, I met online. I answered the door when he came over wearing only stilettos, fishnets, studded collar and nothing else. To make myself more female, I completely shaved my body and did my nails and pedicure.
    bijeffluther bijeffluther 46-50, T 3 Responses Jan 27, 2012

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    My Fantasy I'd love to be taken out on a date

    by a man and treated like a real lady throughout dinner and the show that he'd take me to. During the show, I'd like it if he held my hand and would allow his hands to roam a bit to my breasts. Just a quick brush against them to "test the waters". I'd let him know of my...
    slipgirl274 slipgirl274 61-65, F 1 Response Sep 3

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    I've Done It Once

    Yay for me!!! Okay so the story is as follows.  I met up with a guy through craigslist, and although i have plenty of panties and fun girlie cloths myself he said he had a bunch of lingerie that his ex-girlfriend didn't take with her.  So i decided i would wear what he...
    fornowish fornowish 22-25, M 11 Responses Feb 17, 2009

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    One Of My Fantasies

    I have been dressing on and off for many years. I have never told anyone that I like to wear womens clothes, until now. Being dressed for sex is something have wanted to do ever since I can remember. Bra, panties, and fishnets on under my dress. I walk in the room and see you...
    SissySubAlyssa SissySubAlyssa 36-40, T 2 Responses Feb 7, 2013

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    Always Love It

    I remember the first time I went out and knew I was out for a man. I packed my bag and checked into a motel close to one of the show and arcade places I frequent. Got into the room and laid out all the clothes I had brought to choose from. Made a couple cocktails for me and went...
    shannab shannab 51-55, M 4 Responses Nov 11, 2009

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    My Fantasy

    I love the photo for this forum and wish I could be in the womens position, so here's my fantasy.... I had been cross-dressing for a while and my wife grudgingly accepted it. I had been out dressed one night at the local cross-dresser support group and had been really pleased...
    michelletrans michelletrans 51-55, T 8 Responses Dec 5, 2012

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    My Fantasy

    Wear lace stockings, a tight dress and matching underwear, to have A man use my body, feeding me his **** slapping my ***, spread my cheeks and get me ready tearing off my panties hitching up my dress pound my little love tunnel until he cant **** me anymore, make me into his...
    cockdog71 cockdog71 22-25, M 2 Responses May 10, 2013

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    Sexual Bliss

    I like to cross dress and have for a long time now. I can't help but to imagine playing with a hard **** while dressed up. I feel so sexy in my nylons and panties. I have a ***** that I use quite regular and it feels great. I want the real thing now. I want to feel a man's hands...
    ultrasheer2120 ultrasheer2120 46-50 7 Responses Sep 30, 2011

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    Need A Man Soooo Bad...

    I want to be the woman during sex. It needs to be me that gets ****** in the *** and gives all the guys ********. I need a large, muscular man with a huge **** to hold me in my lingerie and **** me. I want to be dominated like the ***** I am. I want to be the one that walks into...
    MelissaTg MelissaTg 18-21, M 1 Response Apr 6, 2012

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    Bi Gay Or..........

    I consider myself normally as a heterosexual male, but ones dressed as a woman i get desires to suck ****, getting ****** by a man and so on. Most will say: you are bisexual, but i think a bisexual is somebody that can have relationships (and sex) with both genders. Like a...
    sissyslet sissyslet 41-45, M 6 Responses Sep 7, 2013

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    Curiosity Got The Better Of Me

    For the first time in about 13 years, I sucked another man’s ****. I was dressed up at home in thigh-high-fishnet stockings with garter belt, a pencil skirt, and a sensible top. While this isn’t usually sexual for me I got curious and checked out Craig’sList. I was...
    JosetteLaRoc JosetteLaRoc 36-40 1 Response May 19, 2013

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    What Have I Done.....?

    Last night....after a nice dinner out....and after sharing a couple of bottles of wine with my wife, I was a little drunk....and very horny. We started talking....about very intimate things....desires...etc. She mentioned that we don't communicate very much anymore.....and so I...
    scaff69 scaff69 36-40 6 Responses Sep 22, 2012

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    My Boy Friend

    I had explained how i become a crossdresser in my story "Adonia reborn" . Jasmine want to see man sex with me while i was a girl. I didn't met jasmine for last one year. I don't know where she went. She didn't said anything. after she left. I cross dress when no one in my...
    deleted deleted 26-30 Dec 2, 2012

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    It Makes Me Feel Like A Woman Inside... More Than One Way.:)

    I met a guy on Craigslist and we met at a motel 4 times, each time he came in me twice!:) Between that we talked and I practiced my female voice. The last two times I caught myself in the mirror and for a split second I thought it was a woman.:) It wasn't what I was wearing...
    bottomup99 bottomup99 46-50, T 5 Responses Jul 27, 2012

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    Cumtastic!

    I'd been trading some pics with a young asian CD the last few days and we agreed to meet up this morning. I love dressing up but also love sexy CDs and wow was this gurl hot - 21, tight. slim, smooth body.. gorgeous face, a fem sissy boi... Probably one of the hottest times I...
    Loveheels Loveheels 41-45, M 2 Responses Apr 26, 2012

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    First Time

    yup already done it.. I was nervous so i went into his bathroom while he waited in the living room... I changed into my lingerie and wrapped a towel around myself... when I walked into the living room, the towel 'accidentally' fell off.. I did a short provocative dance for him...
    biscuit4 biscuit4 36-40, M 2 Responses Oct 13, 2009

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    ********* As A Slutty Girl

    I have an older friend named Martin(70 yrs), I had a really good sexual experience with him a few weeks ago. I had visited him for an afternoon with another friend and he invited me to stay over so I did. His wife was gone and we talked and he asked me to dress in some clothes...
    Deep4u Deep4u 18-21, M 22 Responses Sep 19, 2013

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    Related Experiences

    hi i am from new delhi india i want to have sex with a sexy girl i will pay her gd bt i dnt hv ma prsnal place to **** plz help me out wht to do
    sexyboy034 sexyboy034 18-21, M 1 Response Sep 2

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    I want to have sex with a female teacher in my school teaches maths,she's not attached and is only a mere 22 years old she has an a body like an hourglass,all the curves in the...
    TheGamechanger TheGamechanger 18-21, M 1 Response Sep 19

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    Even though we don't have a label on our relationship, I still want to have sex with him and kiss him and hug him and cuddle . I like the way he feels inside of me . I don't know...
    neuroticgal neuroticgal 22-25, F 4 Responses Sep 14

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    Im looking for another guy to have sex with my wife in the Houston area. I really want a guy with a big **** to **** her real good. Anyone interested?
    hotguy2016 hotguy2016 26-30, M 3 Responses 18 hrs ago