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I Want to Have Sex With a Woman While Cross Dressed

Personal Stories, Advice, and Support 1,077 People

    I Want to Have Sex Whlie Crossdressed

    and i think i might be close to that i have just recently asked out this girl and the other night we were at the movies the other night and i had worn sum of my mums panties thinkin she wold never know but half way through the movie she took her hand and put it down my trousers i...
    Female Female
    18-21, T
    5 Responses May 14, 2008

    I Wanted This But Not Any Longer

    I don't want to have male-female sex while crossdressed becaue that is not who I am.  There, I said it, I am a Lesbian and I am proud to say it.  I want, no I need to make love to another woman as only another woman can.  That is who I am and what I want...
    deleted767 deleted767
    1 Response Nov 14, 2008

    I Did It Once

    At my last job - there was a woman who worked there who knew I crossdressed - it was dangerous because she knew my wife's family, and it had actually been us knowing she needed a job that let me to wind up angling to get her one there. And it went straight into the taboo realm...
    MirandaAlicia MirandaAlicia
    36-40, T
    2 Responses Aug 9, 2012

    With My Wife

    I would love it if my wife and I were both dressed in sexy lingerie while we had sex.I think the feeling of two bodies wearing sexy lingerie rubbing against each other would be a wonderful feeling.
    happilymarriedguy happilymarriedguy
    51-55, M
    3 Responses Dec 23, 2012

    Want to Try

    I have never had sex with a woman while I was dressed up in womans clothes.I just think it would be the greatest feeling I would ever have.Wearing womens panties and bra just turns me on so we wouldn't need much 4 play.
    diaperandlingerie diaperandlingerie
    5 Responses Dec 3, 2008

    It Was Fun

    The first time I ever expressed a desire to dress up i was so afraid that she wouldn't understand...but to my surprise she said she was willing to have some fun she even put a strap on on and. We started to have some fun but was interrupted and we never tried that again it was...
    cdfan cdfan
    36-40, M
    2 Responses Aug 8, 2012

    Two Ladies

      I have a huge fantasy of having sex with a lady while I'm all dolled up. I imagine beingpicked up by her at a bar or club, going to her place and getting friendly on teh couch. Then she leads me to her bedroomand startskissing me all over while she runs her hands all...
    dab37863 dab37863
    1 Response Oct 23, 2008

    Dressed Up And Make Love

    Fortunately I have had many experiences over the years being dressed up and having sex with my wife. The absolute highlight of these experiences I had already on my wedding night. After the party we retired to our Hotel room where we both undressed, then I put on over the...
    gretatv gretatv
    46-50, T
    3 Responses May 13, 2010

    Sex While Dressed

    I dress in sexy lingerie while making love to my wife and how she even does me with her strap-on. I get all dressed for her in the sexiest panties and bra, with stockings and high heels. I make myself extra "pretty" for her. As we start to make out, there is a knock at the door...
    pantiescouple pantiescouple
    2 Responses Jul 19, 2010

    So I was asked to take some pictures the other

    night to show off my new shoes. I have a pair of patent leather 4 inch stiletto pumps with locking ankle straps. I was told to get a pencil skirt so I did. I put on some black thigh high stockings with garters. Pencil skirt. Corset. A button down shirt. And a corset. My...
    Photogeek47 Photogeek47
    31-35, M
    1 Response Jan 1, 2015

    Numerous Times

    I went through a period when my wife and I would go to bed with me wearing a nightie and panties or just bra and panties. We would have sex and afterwards both sleep in our sticky, cummy girl clothes. It was glorious. Also I have had a girlfriend who knew I was a crossdresser We...
    crikeymoses crikeymoses
    5 Responses Mar 28, 2011

    Sleep In Pink Nightgown

    For Valentine's Day my wife got me two cute nighties, both pink. I don't wear them every day but I sure love to wear them. One is smooth and satiny and the other is cotton but with lace and girly!
    nydan61 nydan61
    61-65, M
    Mar 1, 2009

    Want to Try It Out

    I would love the opertunity to have sex with a woman while I was dressed as a woman we could slowly fondel each other and help each other out of our dresses,skirts and tops slowly remove our stockings/pantyhose then have a girly pillow fight in our bra and nickers before rubbing...
    bundygirl bundygirl
    31-35, T
    2 Responses Aug 7, 2008

    Sex With A Woman Crossdress

    I would love to have sex with a woman while i was crossdressed it would be so very sex and so nice
    tammy2 tammy2
    56-60, M
    1 Response Feb 25, 2010


    I want her to peg me. I want us both be dressed as sexy as we can, and me be the girl. Not a dominatrix, but her 'on top'.
    spearot32 spearot32
    36-40, T
    Aug 8, 2013


    I think it would be hot ******* a woman while dressed as one. Any ladies out there like it?
    xdressme1979 xdressme1979
    26-30, T
    Feb 12, 2009

    Nylon Against Nylon Action

    I suggested to my ex-wife that we play some dressing up sex games. I told her how excited I got at the thought of having sex with her while I wore women´s clothes. She was receptive to the idea and provided me with bra, knickers, suspenders, stockings, a dress and high heels...
    Jonim2009 Jonim2009
    51-55, M
    1 Response Oct 30, 2010

    Sex While Dressed

    I went to a friends house to go shopping with her and her friends. I found this dress for her to wear and everyone agreed. She went and tried it on and it looked really good on her I was jealous. On the way back home Heather brought up that I was a cross dresser and they should...
    Ryan1kc Ryan1kc
    31-35, M
    2 Responses Feb 5, 2013

    I Have Sex Only While Dressed Up

    I have been with my girlfriend for six years now and have never had sex with her that I wasn't at least in pretty panties and normally a matching bra and other items as well.
    sissyribbons sissyribbons
    36-40, T
    1 Response Nov 26, 2008

    Christmas Present

    We were spending christmas alone. Just the two of us. We were not going to visit anyone and no one was comming to visit  us. So I could spend the whole time dressed. On Christmas morning we sat in our nighties and opened our presents. Perfume, stockings. underwear, cosmetics...
    RobynDeLaMare RobynDeLaMare
    56-60, M
    3 Responses Sep 1, 2009

    I Really Do!

    I've admitted to a lot of things or rather, wanting a lot of things on this site that are really more of curiosities or interests (263 so far, lol), but this is my one true fantasy.  I sooo want to make love to a woman while I'm all dressed up.  Ideally of course...
    SomeguyinUT SomeguyinUT
    8 Responses Oct 22, 2008


    just love to be dressed as a sissybitch who gets tied up to the bed and played with before being ****** by my Mistress 8" strap-on!Mistress enjoys playing with her sissybitch often puts nipple clips on my nipples so can pull them while i eat her out and normally get to eat her...
    mandiejune mandiejune
    51-55, M
    Dec 30, 2010

    And Want To Do It Again.....

    It is not that I want to have sex with a woman while crossdressed, as I have and would like to do it again. The encounters were with a female I was corresponding with and we arranged to meet. After meeting a few times she wanted to involve some individual male friends as she...
    allyg allyg
    2 Responses Dec 12, 2010

    You Lucky Girl, You !

    You Lucky Girl, You ! I think one of the most important things that I need to do here, and in general, is to talk to others like me, crossdressers, transvestites, sissies, etc. Alright, so you already know you are not alone. Far from it. But, you still feel guilt, shame...
    CherrySissy CherrySissy
    46-50, T
    1 Response Apr 3, 2009

    Sex When Dressed

     i am a very lucky girl as my wife allows me to  have sex with her whilst dressed         and it is all you expect it to be especially when she runs her hands up my nylon clad legs before taking my stiff **** deep in her mouth and i...
    sarahj sarahj
    46-50, M
    2 Responses Aug 19, 2008

    And I Have...

    Which should come as a shock to no one. God bless my wife :)
    Kris99 Kris99
    41-45, F
    2 Responses Jul 30, 2010

    Sex When Dressed

     i am a very lucky girl as my wife allows me to  have sex with her whilst dressed         and it is all you expect it to be especially when she runs her hands up my nylon clad legs before taking my stiff **** deep in her mouth and i...
    sarahj sarahj
    46-50, M
    7 Responses Aug 19, 2008

    Why I Crossdress

    M y 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
    3 Responses Dec 22, 2008

    Another thanks to my awesome wife.

    She woke me up over the night and told me to put in a pair of thigh highs, corset and some high heels patent leather pumps. She then told me to sleep well. I later woke up with her tying me to the bed. Handcuffs on the head board and rope on my legs. She tied my legs together...
    Photogeek47 Photogeek47
    31-35, M
    2 Responses Nov 27, 2014

    Crossdressed Panty Play

    A female friend found a bunch of lingerie in my apartment.  When I told her it was mine, she wanted to see me in it.  The following weekend, she came over, sorted through all my undies, picked out things for me to model then sat and watched as I started to play with...
    Puddlemucker Puddlemucker
    7 Responses Aug 22, 2008

    If Only !!

    There is nothing I would love more !!! Me dressed black/red baste black stockings red silk thong black knee lenght boots with 4" heels brite red nails with lipstick to match ,the woman dressed almost the same but she is all in white ,She lay's on the bed legs spred wide and as I...
    annfaragian annfaragian
    Jan 5, 2011

    Becoming A Girl

    I was lucky enough to share my experiences with my ex-girlfriend. One day i told her that i have a selection of dresses and skirts and lingerie etc.. , which i would occasionally wear , she was very happy and asked me to dress up for her . The next day she brought me a dress that...
    rachelgirly80 rachelgirly80
    41-45, T
    2 Responses Sep 12, 2010

    Horse-back Picnic

    I have thought of this story for years. A lady-friend and I would go horseback riding, and stop for a picnic along the way. We would both be wearing country-style riding dresses... After our lunch, and some wine, we would snuggle, and become intimate, and while kissing, she...
    Patricia699 Patricia699
    41-45, M
    2 Responses Nov 13, 2012

    My First Time Sex With A Woman Dressed As A Woman.

    I had been a crossdresser for years and slept with my wife many times enfemme but this was different. It was during Thanksgiving holidays, my wife and kids had gone back east for thanksgiving and I had a project to get done and so could not go. A consultant I knew had come to...
    Rebecca61 Rebecca61
    61-65, M
    6 Responses Jan 17, 2011

    Panty Fun With The Girlfriend

    A few weeks ago my girlfriend came and visited me in the town where I go to college. The one thing on her mind was "**** me now." Before she was actually here she was talking about how she had been feeling sex deprived. I was more then happy to comply with her request. After I...
    pinkpantylover pinkpantylover
    1 Response Nov 16, 2010

    Dressed When She Came Home

    My lady came home one evennight after working late and I was waiting for her in the front room of our apartment with candles lighted and a glass of wine waiting for her. She was wearing her business suit and I was wearing her red leather skirt, silk white blouse and a pair of...
    dianedouglascd dianedouglascd
    56-60, T
    1 Response Apr 13, 2012
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