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I Have Sex Dress As A Woman Like A Woman

Personal Stories, Advice, and Support 370 People

    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

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    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

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    "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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    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

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    Related Experiences

    I want to have sex with woman while my boyfriend partipates however he wouldn't **** her or lick her. She would lick me while my boyfriend ***** me and I would return the favour to...
    Readingaddict Readingaddict 18-21, F Aug 9

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    I think i would be great to have sex with a trans women. They are really gorgeous but also independent in a sense. I'm not gay but I definitely want to go for a transvestite woman...
    lolzmeplz lolzmeplz 16-17, M 4 Responses Aug 4

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    I've always wondered what it would feel like to have sex with a man in his late 30's or 40s. Guys my age are too selfish in the sack and brag too much. Note to men: if you feel the...
    naughtybutnice22 naughtybutnice22 22-25, F 18 Responses Jul 29

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    I want to have sex but I'm only 14. Any help or tips?.
    Andersonp14 Andersonp14 13-15, M 3 Responses Aug 5

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    I have always been a good girl but I want to change that and have sex all through out high school maybe even get pregnant any guys want to message me and send pics
    deleted deleted 26-30 4 Responses Aug 9

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    I get turned on by pregnant women so would live to have sex with one
    goonteam goonteam 16-17, M 1 Response Aug 19

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    Before you rant about me being whiny or kids ill-prepared for workforce, let me explain. I disagree with dress codes because too often it's taken too far to the point where girls...
    Emm9 Emm9 18-21 Aug 16

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    I have been cross-dressing on and off for most of my life I am fortunate that I’ [m a man with a 26 inch waist so I can ware junior size women’s cloths Two years ago I started...
    dantodawn dantodawn 51-55, T 1 Response Aug 18

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    In love with this dress, I have to find it and slip it on ;)
    LisaTG LisaTG 26-30, T 2 Responses Jul 29

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    http://imgur.com/a/wG0VX This is Sarah (me dressed up) She is 16, turning 17 in a month. She has a nine month old daughter, Kira, and is currently 35 weeks pregnant. She and all...
    Bagginshield Bagginshield 18-21, F 1 Response Jul 31

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    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 5 days ago

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    It's not that I want to stop. I feel it takes up a part of my life that's a secret and I don't like hiding it from close friends and loved ones.
    mamapapa221 mamapapa221 36-40, M 2 Responses Aug 18

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    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 5 days ago

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    I'm a sexy black girl from PA ;)
    Rayven1997 Rayven1997 16-17, F 2 Responses Aug 10

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    I'm only 19 year old girl, but I would love to have a sexual relationship with a 40-55 year old women and do sexual things with her (or without her) with her teen-age kids (if she...
    Jamielr13 Jamielr13 18-21, F 5 Responses Aug 13

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    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 2 Responses 3 days ago

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    I just think that trans women are so hot. Girl up top but guy down below. I don't know why I just think it's incredibly sexy.
    LadyCNote LadyCNote 26-30, F 3 Responses Jul 31

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    A hot combo, cyber sex...I'm just kinky right now
    camillux camillux 18-21, F 2 Responses Aug 5

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    I just need sex to sleep at the moment!
    deklan deklan 31-35, M Aug 10

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    I really want to have crazy sex with my sister
    Harryharry123 Harryharry123 22-25, M 5 Responses Jul 30

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    This is something I want to try I have never even dated a black man much less had sex with one but there is a first time of every thing right ??
    1Miserablemind 1Miserablemind 18-21, F 8 Responses Aug 5

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    My ideal would be 5-6 times a week. My husband is happy with an every other day schedule, about 3-4 times a week. It's a significant difference from 10 years ago when it was the...
    BBWand40 BBWand40 36-40, F 7 Responses Aug 17

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    '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 3 days ago

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    I'd love it if my guy was wearing light grey slightly destroyed stonewashed jeans, bare-feet, clean shaven and neat trimmed everywhere 😮, smelling like a fresh shower🚿, he'd...
    Emojinoid Emojinoid 31-35, F 3 Responses Aug 2

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    WHEN I GET PREGNANT - I want to breastfeed my husband while gently kissing his forehead & massaging his d/I/c/k. I can't wait to see my sweet milk dripping down his lips. I would...
    Peachesx0 Peachesx0 22-25, F 4 Responses Aug 8

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    she looks hot!!! like banging her tight ***** would make my day
    evildesires evildesires 18-21, M Aug 13

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    he's not necessarily attractive or anything. it's just something about his old school, authoritative look that really turns me on. I can just imagine it going like this: me: is...
    fuckinglife fuckinglife 16-17, F 1 Response Aug 15

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    I so badly crave my friends boyfriend he's hot and possessive and dominant and I love everything about him and my friend is a ***** to me anyways and they have only been dating for...
    cootyboo cootyboo 22-25, F 3 Responses Jul 30

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    Would you go have me boys?
    mommygotboobs mommygotboobs 36-40, F 14 Responses Aug 7

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    Been here for quite a while and in my Opinion, it is the hardest city in the U.S to get laid!! It so frustrating to put so much effort into something that should happen naturally...
    thatguy4582 thatguy4582 18-21, M Aug 14

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    Im almost 21 and my sister Anna is 18. Ever since we were little we have had a special bond. We have always been super close. but recently i've been looking at her differently. her...
    HannatheBanana93 HannatheBanana93 18-21, F 2 Responses Aug 16

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    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 Aug 20

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    A older guy.. Better or worse??
    BeauteFloue BeauteFloue 22-25, F 2 Responses 16 hrs ago