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I Have Sex Dress As A Woman Like A Woman

Personal Stories, Advice, and Support 369 People

    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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    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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    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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    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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    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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    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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    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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    "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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    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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    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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    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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    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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    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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    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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    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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    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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    When I was really young there was a teenage girl with dwarfism in my neighborhood that I saw regularly. I don't think I was even old enough to like girls yet but there was...
    thatguythereoverhere thatguythereoverhere 26-30, M 2 Responses Jul 27

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    SUMMER CAMP TRUTH OR DARE Earlier this summer my sister Lizzie and I went to the same summer camp. We stayed there for two weeks. A lot of other kids from our school were going to...
    Jenjoejen Jenjoejen 13-15 3 Responses Jul 21

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    Would love to have Sex with a pregnant woman would be a great turn on
    Hazza8989 Hazza8989 22-25, M Jul 25

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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 11 Responses Jul 29

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    This year, I had a extremely attractive chemistry teacher. He's sweet, and has vibrant blue eyes, short blonde hair and a perfect body. Every time that I would look at him, I...
    Jeanpocket Jeanpocket 13-15, F 1 Response Jul 22

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    I am 16 and have wanted to have sex so badley since I was 13. I am now legal so I just want to do it. I need a girl of any build but a nice personality :) message me or heart this...
    goonteam goonteam 16-17, M 1 Response Jul 23

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    i have sexual attraction towards my son////
    elinarose37 elinarose37 36-40, F 5 Responses Jul 25

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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 2 days ago

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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 4 days ago

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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 3 days ago

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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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    I don't know why but I'm beginning to like dressing like a girl and feeling like one..the only thing is I like doing it sometimes not all the time and I'm straight..what's wrong...
    Heaven21 Heaven21 18-21, M 7 Responses Jul 24

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    Here it goes, I think I'll do 3 fantasies in one post? Just so my names is clogging up the fantasy section XD 1. So I think one of the hottest things ever would be just forced up...
    WintersSoldier WintersSoldier 18-21, F 5 Responses Jul 26

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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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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 1 Response Jul 23

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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 3 days ago

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    This is my 1st post of any kind on ep. Yes i am a crossdresser! I love all things feminine. I have done this since i was a teen but currently have only a few items. Dam purges...
    dyaneleigh dyaneleigh 51-55, T 1 Response Jul 23

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 1 Response Jul 23

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    I just turned 19 & I think it would be so sexy to be with a guy like 30-40. Experience is such a turn on and I bet someone that age would have a lot. That's like my biggest fantasy...
    wayyfarer wayyfarer 18-21, F 16 Responses Jul 26

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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 a week 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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    My boyfriend lost his romantic side when he got his job. He used to be sooo romantic but when the time that his Aunt gave him a job he just completely forget about me. I mean no...
    Johanned Johanned 22-25, F 1 Response Aug 7

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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've always had this one fantasy One night I find a guy that I'm going to lose my virginity to and he comes to pick me up. When we are about halfway to the motel I grab him and...
    xmyzer xmyzer 13-15, M Jul 26

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    I really want to have crazy sex with my sister
    hornyharry123 hornyharry123 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 6 Responses 3 days ago