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

I Have Sex Dress As A Woman Like A Woman

Personal Stories, Advice, and Support 369 People

    Lost My Virgitity As A "woman"

    I can still remember my first time with a ma, i met him on a party line and invited him over. I was ****** up dressed in my best bra, panties, mini shirt, low cut blouse & stockings. It was the first time ANYONE else saw me dressed fem as well...He walked in and gave me a big...
    vegasjenssen vegasjenssen 31-35, M 2 Responses Nov 23, 2010

    Your Response

    Cancel

    Done Right

    My first time having sex while dressed could not have been better. I met this man at a bar, he bought me a few drinks, we danced a bit, he started nuzzling my neck and asked me to leave with him. Up to this point I had only gone for drinks, and headed home but something about the...
    JulesAnn JulesAnn 41-45, T 11 Responses Dec 5, 2010

    Your Response

    Cancel

    I Dress Like A ***** Then Act Like A ****

    I have been dressing to please men since I was 7 and wore my mom's bra and panties while I sucked a neighbor's ****. It made me feel so naughty and I have enjoyed that feeling ever since. These days I dress up very sexy whenever I plan to get with a guy or guys...the feeling of...
    barbarascampbell barbarascampbell 41-45, T 1 Response Dec 15, 2010

    Your Response

    Cancel

    Jocelynj's Story

    I love dressing as a woman   period  i dont know if i have the courage or desire to live as one   all i know is my body feels so sweet in female clothes. I want to make friends with others who feel the same
    JocelynJ JocelynJ 36-40, T 7 Responses Aug 5, 2010

    Your Response

    Cancel

    Is There Any Other Way?

    I now live as a woman, and am an escort. I dress very sexy when on a date showing lots of skin.I rarey take off my clothes to have sex, as much of the time I get bent over somthing to be ******, and on my knees when I suck a ****.I love when I am bent over and getting...
    RunAroundSusan RunAroundSusan 22-25 Apr 13, 2013

    Your Response

    Cancel

    His Name Is Ray

    I have been dressing up as a girl since I was about 10 years old. I knew I was different from the other boys but I didn't think there was anything wrong with me. Still, I kept it to myself until twelve years ago. I joined a Transgendered support group and met many others like...
    dianalynn63 dianalynn63 46-50, T 1 Response Aug 13, 2010

    Your Response

    Cancel

    Anniversary

    The wife and I had gone away for a few days to celebrate our anniversary. After we had dinner we went back up to the room to relax, and have some serious sex!! I went over and started filling the two person hot tub when my wife stood over it and poured some scented oil, or gel...
    allwrappedupinit allwrappedupinit 51-55, M 5 Responses Oct 13, 2011

    Your Response

    Cancel

    Dressed As The True `me' And Making Love

    Hi This one experience on this site that I say that I have most certainly done that. I am transexual and dressing as a woman wll, I am a woman so that perfectly natural. I indenify as a lesbian and most of my experiences have been with out women. I have also experimented with...
    subpaulagirl subpaulagirl 41-45 Aug 7, 2010

    Your Response

    Cancel

    Enjoying Sex As A Woman

    I have written a story about having sex as a woman. It is called " My date with **** ". My friend wanted to go out one night drinking and riding around, so I thought I would dress up and be his "date" He was also a crossdresser and I convinced his to not to dress up. He picked me...
    davis36a davis36a 61-65 1 Response Dec 19, 2011

    Your Response

    Cancel

    Enjoy Being Dressed While Having Sex

    I used to crossdress with my first girlfriend. I loved wearing her panties and lingerie when we made love together. I am lucky now to be married to a woman who enjoys seeing me crossdressed, she loves picking new things out for me or being surprised with things I have bought. Its...
    pantiescouple pantiescouple 26-30 Jul 20, 2010

    Your Response

    Cancel

    I Share Your Feelings

    I also have fantasies about  being dressed as a woman, and receiving  sex from  a gentel, careing  person. I n my fantasies, I  preform  as a woman  would be expected to during sex,  with me sucking, and being penetrated.  My...
    enejoy21 enejoy21 70+ 1 Response Dec 20, 2009

    Your Response

    Cancel

    I'm Not A Full Cd, But I Do Enjoy Dressing Up

    I started dressing with just panties, and ************. Then it progressed when I met a man on a sex site that wanted me to wear some panties he had, while he filled my *** with his 8.5 inch uncut ****, and later his hot load of ***. Needless to say I thoroughly enjoyed it, even...
    Stayinshadow78 Stayinshadow78 31-35, M 2 Responses Oct 6, 2010

    Your Response

    Cancel

    This Is Very Exciting

    This has to be one of the best experiences of my life. I have done this on two occasions and had the time of my life. Both times were in hotel rooms. the first time I was dressed waiting for him to show up. I was wearing a long black tight dress with a black garter and stockings...
    AustinButtMan AustinButtMan 41-45, M 2 Responses Aug 10, 2010

    Your Response

    Cancel

    Sex Dressed As A Woman Like A Woman

    i love being dressed as a woman and getting sex like a woman!My Mistress makes me her sissybitch and i love to suck her ******* in my red lipsticklips before she uses it to **** my sissy ***** just love being ******!enjoy the feeling of a hard ******* up my sissypussy or a...
    mandiejune mandiejune 51-55, M Mar 1, 2010

    Your Response

    Cancel

    "my *****"

    I love dressing up as a schoolgirl (naughty schoolgirl). My wife would strap my arms and legs down. Then slowly tease me, sliding her fingers under my shirt reaching my bra, then pinch my nipples. I love when she plays with my nipples. With my shirt up by my bra, she slowly...
    deleted deleted 26-30 6 Responses Nov 27, 2009

    Your Response

    Cancel

    Want To Do It More

    I've been cross-dressing for much of my life, but never had let anybody see me dressed. But I was fascinated by the idea of having sex dressed as a women although I had never had any sex with a man and didn't even know how to get started. Finally I got up the nerve and posted an...
    RayanneA RayanneA 56-60, M 1 Response Apr 1, 2012

    Your Response

    Cancel

    Related Experiences

    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 23 hrs ago

    Your Response

    Cancel
    I love dressing up like a girl and using butt plugs x
    SluttyCP SluttyCP 18-21, M 5 Responses Aug 30

    Your Response

    Cancel
    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

    Your Response

    Cancel
    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 3 Responses 5 days ago

    Your Response

    Cancel

    Your Response

    Cancel
    i would love to be a woman's personal barbie doll. letting her dress me up all day, everyday in different girlish outfits and doing my makeup & hair too
    girlyAndrea1987 girlyAndrea1987 26-30, M 1 Response 3 days ago

    Your Response

    Cancel
    I had a great experience yesterday, I went out in a dress/bra /panties etc. I put on a drress with bra and panties, and went to the drive through. I did not put any make up on...
    mostlynatalie mostlynatalie 31-35, F 4 Responses Sep 9

    Your Response

    Cancel
    I dress as a girl every day and can't wait to get up in the morning and chose a dress and shoes
    dantodawn dantodawn 51-55, T 1 Response Sep 5

    Your Response

    Cancel
    Bobby and the girl at a friends birthday party Britney and Kathleen took me to a friends birthday party Saturday. I wore a printed knee length dress with a short net petticoat...
    bobbylee111 bobbylee111 36-40, T 1 Response Aug 23

    Your Response

    Cancel
    I have. It was awesome she was blonde
    lotsoflove12 lotsoflove12 31-35, M Aug 31

    Your Response

    Cancel
    I'm looking forward to it again this year! Thinking of dressing as a bride or Elvira
    Brandie1960 Brandie1960 41-45, M 4 Responses 4 days ago

    Your Response

    Cancel
    I was just thinking am i cute enough to sleep with woman??
    Bbailey84 Bbailey84 26-30 Sep 9

    Your Response

    Cancel
    Bobby and the girl at a friends birthday party We watched music videos of Selena Gomez and Justin Timberlake and danced. Played truth or dare which was a lot of fun. We talked...
    bobbylee111 bobbylee111 36-40, T Aug 23

    Your Response

    Cancel
    I was a virgin on my 18th birthday, graduation day, and on my wedding day too. On my wedding we tied the knot, had a great wedding reception, went to our honeymoon destination...
    heatherinarizona heatherinarizona 31-35, F 3 Responses Aug 25

    Your Response

    Cancel
    I know sex is the way of life and all but that **** when ever people describe it to me it sounds like its painful as hell... I tried to try it once but I chickened out, I don't...
    SchniderMonkey SchniderMonkey 18-21, F 1 Response Sep 5

    Your Response

    Cancel
    My girlfriend has been having sex with other guys, about 2 of them she had sex with multiple times
    jma13f jma13f 18-21, M 1 Response Sep 7

    Your Response

    Cancel
    My ex and I broke up a couple of months ago, and while I don't want him back, there is still something there that makes it hard for me to stay away from him completely. The thing...
    PepperF PepperF 22-25, F 3 Responses Sep 9

    Your Response

    Cancel
    I want to make love as I have never done it before and then it wanna have some nice smooth gentle sex to get me into it
    goonteam goonteam 16-17, M 6 days ago

    Your Response

    Cancel
    've met this wonderful young man two years ago. He's tall, has the body of a gladiator and the face of a Greek god. His blue eyes, sunny smile and his hair as blond as a wheat...
    CrackedPorcelainDoll CrackedPorcelainDoll 18-21, F 1 Response Aug 25

    Your Response

    Cancel
    Spandex is so amazing and I really want to have a women wear spandex while having sex!
    ILoveSpandex ILoveSpandex 18-21, M 1 Response Sep 9

    Your Response

    Cancel
    I want to suck a guy. I love the thought of having a guy in my mouth. Would also like to bottom for the correct guy.
    MITUK MITUK 36-40, M 2 Responses Sep 9

    Your Response

    Cancel
    I would like to exchange and discuss fantasies with other people
    camfun99 camfun99 51-55, M 4 Responses Sep 11

    Your Response

    Cancel
    I am so horny and want to have s e x with older man like 40's-60's. ;)
    Elizabeth214444 Elizabeth214444 22-25, F 1 Response 2 days ago

    Your Response

    Cancel
    I have straight and gay ones. Cause I'm bi. My gay one is I'm young guy who gets ********** by a room full older men. Black white I dnt care haha
    Keanu1991 Keanu1991 22-25, M 1 Response Aug 20

    Your Response

    Cancel
    I have a deal for yu if yu willing to listen go read my experiences plz and inbox me serious ppl onli!!!
    ih8beingyung ih8beingyung 18-21, F 1 Response 5 days ago

    Your Response

    Cancel
    Im 23 years old i have a half sister from my father samuel bracey. All i know about my sister is her name is Heather she is 6months younger then i am so she would have been born in...
    jessicawilliamson jessicawilliamson 22-25, F 3 days ago

    Your Response

    Cancel
    I love to feel confident and naughty wearing one ;)
    elisasama elisasama 18-21, F 2 Responses 3 days ago

    Your Response

    Cancel
    It was a sleepover, he crawled into my bed. He got on top
    lotsoflove12 lotsoflove12 31-35, M Aug 31

    Your Response

    Cancel
    Would love any comments(: not to harsh please
    DoubleDirtyPanties DoubleDirtyPanties 18-21, M 9 Responses Aug 29

    Your Response

    Cancel
    Not yet, but I want to! I don't consider myself passable most days. I would hope that with a little help, I could pull it off a little better.
    JosetteLaRoc JosetteLaRoc 36-40 4 Responses 4 days ago

    Your Response

    Cancel
    I want a hermaphrodite to **** me xxx
    sassss52 sassss52 22-25, F 1 Response Aug 20

    Your Response

    Cancel
    Or cyber with :) the older the Better come and get me
    Happiness412 Happiness412 18-21, F 5 Responses Aug 27

    Your Response

    Cancel
    A older guy.. Better or worse??
    BeauteFloue BeauteFloue 22-25, F 3 Responses Aug 28