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I Have Sex Dress As A Woman Like A Woman

Personal Stories, Advice, and Support 360 People

    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
    Apr 13, 2013

    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
    Jul 20, 2010

    Anyone who has read my stories will know about

    my relationship with Mistress. Now She has decreed that I must buy a hollow strap-on so that we can indulge in true lesbian acts. The one She selected is 12" long, 8" circumferance and jet black. I can fit quite snugly into the inner sleeve, but get no sensation at all. Mistress...
    ronkey02 ronkey02
    56-60, M
    May 5, 2015


    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
    3 Responses Oct 13, 2011

    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
    Aug 7, 2010

    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
    1 Response Nov 23, 2010

    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

    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

    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

    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
    Dec 20, 2009

    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
    9 Responses Dec 5, 2010

    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

    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

    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
    1 Response Dec 19, 2011

    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

    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
    1 Response Aug 10, 2010

    "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
    6 Responses Nov 27, 2009
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