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

Personal Stories, Advice, and Support 1,813 People

    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
    46-50, T
    Oct 6, 2013

    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
    6 Responses Aug 20, 2013

    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
    5 Responses Aug 22, 2012

    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
    Dec 2, 2012

    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
    Sep 9, 2012

    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
    7 Responses Dec 5, 2012

    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
    51-55, T
    4 Responses Jul 27, 2012

    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

    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
    1 Response Apr 12, 2014

    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
    Feb 11, 2013

    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

    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
    9 Responses Sep 22, 2012


    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

    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
    2 Responses May 19, 2013

    Craigslist I'm always afraid to post my self

    on Craigslist but one day I was so horny so i decided to post on there what I was looking for I had few guys hit me up but one of them got my attention he was 40 blk m 6'2" 250lbs 9.5". I replied to his email and told him I would like to meet I jumped in the shower shaved all...
    jessica525 jessica525
    26-30, T
    10 Responses Nov 24, 2014

    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

    ********* 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...
    AnneTheSissy AnneTheSissy
    22-25, M
    20 Responses Sep 19, 2013

    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
    3 Responses Jul 7, 2010

    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
    5 Responses Apr 11, 2013

    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
    3 Responses Jan 5, 2013

    this has to be the best feeling ever cannot

    wait to do this I have wanted to do this for a long time now every time I think about it I want it move and more
    deleted deleted
    Jun 30, 2015

    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
    34 Responses Dec 11, 2011

    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...
    deleted deleted
    8 Responses Oct 1, 2011

    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

    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...
    deleted deleted
    6 Responses Feb 7, 2013

    Been There ...

    If I'm hooking up with a guy I'm wearing girl clothes. My first gay experience was a direct result of wanting to show off my girl clothes to a man. But that is not this story, its probably posted in another group. (end tangent) I remember meeting a guy on craigslist and inviting...
    Phreeek Phreeek
    3 Responses Oct 15, 2009

    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...
    deleted deleted
    6 Responses Sep 7, 2013

    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

    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

    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
    5 Responses Oct 10, 2010

    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
    41-45, M
    1 Response Oct 31, 2013

    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
    1 Response Aug 6, 2013


    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

    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

    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
    2 Responses Jan 7, 2013

    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...
    deleted deleted
    5 Responses Sep 30, 2011

    I love to try on my wife's underwear

    and fantasize about being taken by a dominant, well-hung man. I've never done anything with another man before.
    mdreader mdreader
    31-35, M
    Oct 30, 2015

    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
    26-30, M
    2 Responses May 10, 2013

    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
    51-55, T
    3 Responses Jan 27, 2012

    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
    10 Responses Jul 13, 2011

    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

    I have given a man a bj

    while dressed as a woman (a few times) and loved it. I got so excited that my panties were soaked by the time I finished him off. Haven't had sex while dressed yet. Hopefully someday I will. I am sure it would be the greatest sexual sensation that I have had in my life with the...
    chrissyk48 chrissyk48
    46-50, M
    2 Responses Nov 28, 2014

    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
    5 Responses Dec 2, 2012

    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

    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
    Jan 2, 2013

    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
    1 Response Oct 13, 2009
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