This experience may contain mature content, as flagged by the community.
Please click away if you do not want to see this content.
To report inappropriate content, please email us.

I Want to Experience Sex As a Woman Would

Personal Stories, Advice, and Support 1,438 People

    I Want to Be Filled to the Brim and Again and Again

    After things get right with my body I am going on a mission to get filled and screwed as much as possible and in as many positions there are. I want to be filled up with juice to the top until it runs down my legs and all over the bed and then after we sleep do it really...
    Lyndsey2u Lyndsey2u
    61-65, T
    8 Responses Sep 1, 2008

    My Greatest Wish

    It is probably my greatest wish, wanting to experience sex as a woman. I am extremely curious to know how it feels for women to have sex. Do their ******* feel different then men experience *******? Probalby, but how does it feel to ****** as a woman? How does it feel to be at...
    Azalkmaar072 Azalkmaar072
    22-25, M
    Apr 11, 2013

    I would love to just lay there

    and let someone else do all the work
    deleted deleted
    26-30
    Jun 17, 2015

    Oh My God

    It would be so wonderful to feel the sex that a woman would when a co..k came into her vagina
    Beenaround Beenaround
    56-60, M
    2 Responses Apr 30, 2013

    I Wish ...

    Whenever I see beautiful women in clothes in photos, or on tv, I just want to be them ... When I watch ****, whether it be lesbian, or straight, I always think of being that girl, never the guy. I want to know what its like to have a ***** fingered, or with a **** in it, having...
    thebunny030 thebunny030
    22-25, M
    2 Responses Dec 18, 2011

    I've Kind Of Taken The First Step

    I've sucked a **** while I was dressed as a woman. Next I would like to be ****** in the *** while I'm dressed as a woman. But what i really want if for another man to seduce me and make love to me as if I was really a woman.
    RayanneA RayanneA
    56-60, M
    3 Responses Apr 17, 2012

    I Would Love To Take Possession Of My Wife'S Body For A Week And Become Her...

    I've read a few of the posts on here and what really gets me going is not dressing as a woman, or even becoming a woman surgically but for the lack of a better phrase, magically becoming a woman for a week. Specifically becoming my wife, and then get picked up by guys and have...
    Jan 28, 2013

    Every Night

    Sex is much better for the woman then it is for the man. The man just humps and that's pretty much all there is to it. Now a woman is completely different. I would love for the guy to foreplay with me, kissing and licking all the sensitive spots that make my ***** tight, lusting...
    deleted deleted
    26-30
    1 Response May 22, 2012

    I have wanted to be female since

    before I even knew what the physical differences were from male and female. Since as early as 7 years old, if not even earlier, I knew I really should have been born a girl. As far as wanting to experience sex as a woman would.., that has been my one major sexual desire ever...
    SomedaySarah SomedaySarah
    46-50
    1 Response Jul 25, 2015

    Make Me Feel Like A Woman

    I don't like labels.I am married but dont have sex with my wife but i have great sex with  my boyfriends, guys who dress straight but like us crossdressers.I'm not so keen on doing it wih other cd's but I have with mixed results.what ever does it for you, enjoy it.
    christinemelody christinemelody
    56-60, T
    Apr 7, 2012

    Wedding Dress

    While living in Europe, I became friends with a very creative and sensual woman who loved sissies. We would play for hours as I modeled outfits for her and share fantasies. Usually, we would end up with her ******* me with a *****. Of course, this lead eventually to her asking...
    bluesatin bluesatin
    46-50
    7 Responses Mar 1, 2010

    Going Out...

    I would love to be picked-up in a club. You buy me a drink, and we sit there and chat. I'm nervous at first, you're so handsome and I'm just now getting my look down enough that I feel comfortable going out... A slow song starts to play. You take my hand and lead me to the...
    GillianStepford GillianStepford
    41-45, T
    4 Responses Jun 13, 2013

    since i have a permanent boyfriend i dont want

    to have sex with my wife anymore. Once in the past 2 months we had it on and i really hated it. I told my boyfriend and he asked would I mind if he tried to seduce her. I said that was ok. He did it with her, i know the day, cos she felt very guilty and that night we had sex. I...
    sjmb1968 sjmb1968
    41-45, M
    2 Responses Mar 15, 2014

    Try As A Woman

    I really just want to try everything as woman and see what the difference is. This includes more than sex, I want see whats it like to have a period, to pee, to be more emotional. I want to see what its like to be a woman.
    iltwphah iltwphah
    36-40
    1 Response Mar 6, 2012

    that would be a dream come true I all ways

    think about it and how it would feel It must be fantastic
    janetjanet janetjanet
    51-55, T
    Feb 28

    I Think I Would Love To Have Sex As A Woman

    The thought of being a woman... having a vagina and breasts, soft skin and long hair. I'd like to be put on my back and have my legs held open, feeling so vulnerable... and having someone's penis or strap-on thrusting deep into me, while I take a penis in my mouth while they rub...
    Talivia Talivia
    18-21, T
    3 Responses Oct 3, 2013

    A Broken Record ... Maybe

    I want to know that a man desires me as a woman. I want to hear him say that. I want to fell his hands slide around my waist as he pulls me to him. I want to feel his lips softly, gently, passionately kiss mine. I want to feel his hands as they unzip my dress. I want to feel...
    Josie06 Josie06
    56-60, F
    11 Responses Jul 15, 2008

    Being Held

    laying face down on the bed, feeling the weight of a man on top of you gently pressing his manliness against you.  The feeling of anticipation you get knowing he is about to have you.  The liberating moment he slips into you and you are no longer what you thought you...
    vanessacarr vanessacarr
    36-40, T
    5 Responses Aug 7, 2008

    that is something that I have fantasies about

    for years for me that would be a dream come true even if it was just for one day to have that experience I would love every second of it
    deleted deleted
    26-30
    1 Response Jun 16, 2015

    Catherine Zeta Jones sex fantasy with a Hot Well Hung Stud!!

    I have this fantasy about looking exactly like Catherine Zeta Jones in her prime, except with even bigger breasts, 36 D-Cups. Walking around in a nightclub where every man is looking at me. I flash each of them a suggestive, seductive smile. They melt. Almost every guy tries to...
    furiouscuriousgeorgeporge furiouscuriousgeorgeporge
    26-30, M
    1 Response Dec 3, 2012

    Waking In The Morning (The Morning After! the "Two Part Beginning" First Time Sex As A Crossdresser)

    I woke foggy,,, feeling like a kid on Christmas morning! There was something new and different in my life! I laid still, trying to figure out why I felt so different, I had a new feeling about myself I opened my eyes, next to me he was asleep...
    chartless chartless
    61-65, M
    8 Responses Nov 24, 2010

    Experiencing Sex As a Woman - My First Time

    I first experienced sex as a woman with a man about 10 years ago.  I thought about what it would be like often but didn’t have the courage or opportunity to experience it. It was about that time that I meet other CD’s. It was like an awakening for me. I loved...
    deleted deleted
    26-30
    4 Responses Aug 5, 2009

    I dream about this for years I would love to

    find out what it would be like
    deleted deleted
    26-30
    Jun 20, 2015

    My Dream

    I have always dreamed of being a woman. I think about it all the time. I would love to have beautiful big breast and an amazing *****. If there was a way to switch my body for a woman's body I would do it in a heart beat. No questions asked. It could be for a couple of hours...
    paulrhight paulrhight
    36-40, M
    1 Response May 10, 2013

    Take Me

    I've always been straight, but have always wished I was a woman. Lately though the desire to have sex as a woman has driven me to fantasize about a **** sliding into my sissy ****. I imagine it every time I am wearing my sexy lingerie and dresses.
    Alexis299 Alexis299
    26-30, T
    5 Responses Sep 12, 2010

    Uh Huh.

    I've been wanting to be a woman since I was young, 11 or 12. I've wanted to have sex as a woman for so very long.  I've been on a low dose of estrogen for over a year now and my skin is now very soft like a woman and my breasts and nipples have gotten oh so very sensitive!  My...
    Ellefem Ellefem
    51-55, T
    6 Responses May 10, 2013

    Love It In Lingerie...............

    I loves all womens underwear. When my wife worked night shift, I used to dress up in her stockings, suspenders, panties and a sexy negligee and go to bed. It felt so good! I recently met a guy who is now my boyfriend. He calls me his **** because I will do anything to him. When...
    sjmb1968 sjmb1968
    41-45, M
    1 Response Feb 2, 2010

    Hopefully Soon...

    Hopefully I'll have this happen soon. I just had a nice phone conversation with someone who wants to hook up some evening this week. He is looking for an ongoing relationship so hopefully looking for the same things I am... or should I say the other half of what I am looking for...
    Aeslyn Aeslyn
    36-40, T
    3 Responses Apr 10, 2012

    Oh Gosh!?!?!?!

     OK I confessed a lil while ago about my neighbor catching me dressed as a girl and then having giggle some 'play time' with me....well ever since then i can't stop thinking about him...and i got as bold as I've ever gotten yesterday... well  after padding round the...
    deleted deleted
    26-30
    9 Responses Aug 15, 2008

    I'm past do and wa mtan open minded woman

    or a manly man. In Idaho or love to experience web camera and meet up some how.
    jessie121412 jessie121412
    41-45, T
    2 Responses Dec 24, 2015

    F****d Like A Woman

    When I was in high school,I found myself wondering what it would feel like to put on pantyhose,so I boght a pair at a gas station,putting them on in their bathroom.I came out of the stall,and my neighbor was standing there.He wlaked forward and pulled me back into the stall.He...
    jwpalerider jwpalerider
    41-45, M
    1 Response Sep 13, 2012

    Sex As A Women

    The other day I started to get dressed as a women to go out.I felt lucky so I took extra care cleaning out and putting my man hood away.I didn't eat the day before so it was'nt hard to clean up.I taped my **** to my leg ank tucked my balls.When I put on my pantyhose it looked...
    Berrney Berrney
    56-60, M
    2 Responses Dec 8, 2010

    Would Love It

    I would love to experience sex as a woman taking a **** in the mouth then Get it shoved in my vagina that would be amazing
    Transjenifer Transjenifer
    18-21, T
    3 Responses Apr 20, 2013

    Nearly There

    It is going to happen sooner than I could have ever dreamed, thanks to the support and understanding of my close friends, family, and coworkers. Only a little while to go. :)
    KatieJane KatieJane
    36-40, F
    9 Responses Jun 28, 2009

    As Time Passes

    When I was younger, I used to look at ****. The women were beautiful. They made me hot and horny. I wanted them. Wished I was the man. But something changed over the years. Slowly, ever so slowly, I started to wish I was the women in every scene. That I was dressed pretty, and my...
    kelli17034s2 kelli17034s2
    56-60, T
    2 Responses Jul 5, 2013

    Girls Have It All!!

    I'd give anything to be able to experience true love making as a woman does, I know ho wthe hormones make me feel and how it feels to use various sized toys and the massive ******* I can achieve,,, yet that still doesnt compare to having a man or another T girl grasping your body...
    ambershot09 ambershot09
    36-40, T
    3 Responses May 17, 2011

    I Old Love It

    Even if it were only once. I have fantasies about have breasts that are bouncing while I am riding. And I mean dress in stilettos, nylons, garter belt with my long hair whipping around. Or having my legs pinned up in the air while having sex!!
    spearot32 spearot32
    36-40, T
    Aug 8, 2013

    Want to Experience For Myself

    I want to experience for myself the feeling of haveing someone slowly arouse my body wrap my legs arond their hips and have them enter my body slowly thrusting in and out untill that point where they can no longer hold back and unload into me. Then I would love to help clean them...
    bundygirl bundygirl
    31-35, T
    3 Responses Aug 14, 2008

    My Dream

    My whole life I've wanted to be a woman. I've wished even as a kid I loved the female body. I think that is why I wear female bra's and panties because I wish I was a woman. Some may say I'm gay but no I'm not. I love women and have nothing against gay people and even consider...
    SmallFatGuy SmallFatGuy
    41-45, M
    Aug 3, 2013

    New At It

    I have been crossdressing on and off for many years My wife don't aprove it, I wish that I knew more back years ago. I have been on many feminine hypnosis sites, and natural breast enchancement therapy. I would love to experance sex as a woman and have a guy come inside me. Also...
    barcardi barcardi
    51-55
    2 Responses Oct 2, 2012

    Sometimes I Wish I Were a Woman

    I mean first off, women get more fun from sex than men do, so how can anyone disagree with this, right? But more than that, I feel like it is something I deserve. I have the body of a man and the mind of a woman. Most people believe that gives me the ultimate advantage, but they...
    thereaverofdarkness thereaverofdarkness
    26-30, M
    23 Responses Dec 6, 2008

    My Ultimate Goal

    I have been cross dressing since a teen and I will not tell you how long that has been, just know that it is a long time. I have worked hard over the years to perfect my female persona and although I probably would not pass in the bright light, have gained some satisfaction in...
    Mustanglisa54 Mustanglisa54
    56-60, M
    6 Responses Aug 11, 2013

    Fantacy Vs Reality

        Many of us girls fantasize for a long time before actually giving in to that deep down urge that makes us want to have sex with a man. We use toys on ourselves, and imagine what it would be like to actually be on our knees in front of a beautiful man. In...
    vanessacarr vanessacarr
    36-40, T
    18 Responses Oct 25, 2008

    Almost Perfect Nigth

    I had been crossdressing couple years. Just the feeling of being a girl gave me huge pleasures. Still it was my little secret, I havent told anyone. So one nigth I was in party, my friend threw. We were drinking and everyone was having fun. I had always considered my friend hot...
    Kalastaja Kalastaja
    18-21
    3 Responses Oct 22, 2010

    I've had an ex gf doll me head to toe

    as a femme lil play thing, she made me look sooo incredibly passable. The pumps, lingerie, wig and makeup were all on point. She naired by body to be nice and smooth and lotioned me up before a few sprays of her powdery fresh perfume. We spent the day with myself straddled on...
    Orlandoadventure Orlandoadventure
    31-35, M
    4 Responses Mar 16

    A Man Can Dream...

    I have been having a recurring dream. In real life, my wife has an openly bisexual friend who I'll call Carl here. Carl has had an off and on guy crush of sorts on me. He has expressed this to her, and she has shared it with me. She thinks it's "cute." She doesn't want...
    JosetteLaRoc JosetteLaRoc
    36-40
    2 Responses Apr 25, 2012
More Stories