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I Have Sex Dress As A Woman Like A Woman

Personal Stories, Advice, and Support 367 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 22-25 Apr 13, 2013

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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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    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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    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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    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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    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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    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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    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'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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    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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    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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    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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    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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    "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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    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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    Related Experiences

    Im 21 ebony chick , and I love to wear a stap on dill do. Weather its under my skirt or inside a pair of shorts or jeans. How is it that i almost feel naked without it. If im...
    catrina69 catrina69 18-21, F 6 Responses 4 days ago

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    Would love to find a woman, here in Las Vegas, that would like to dress me like a woman. I love to look and act slutty.
    bcvegas4u bcvegas4u 66-70, M 1 day ago

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    I want to have sex with my school's mascot. I've never seen him without his outfit on, but I would want to do it while he was still wearing it. The way he's so fun and flirty at...
    Beccalei12 Beccalei12 22-25, F 5 Responses Sep 27

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    I have a gigantic crush on my teacher! He's so hot! Everything he does is hot! And he favorites me over a lot of people. He often jokes around with me, and he is not the joking...
    ihatemytown ihatemytown 13-15, F 2 Responses Oct 14

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    yes i will do anything to have sex such as travel to other country
    newlife30 newlife30 26-30, M a week ago

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    So Halloween was coming up and my team decided to do a pot luck for our weekly meeting which happened to be on Halloween to celebrate the holiday. I had dressed as a girl once...
    GirlyMe GirlyMe 46-50 4 Responses Sep 27

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    I'd describe myself as a straight, in the closet , cross dresser. For years I used fancy dress parties as an excuse to dress up, and , to be honest , i've always had a thing about...
    donnaka donnaka 36-40 1 Response 1 day ago

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    I would love to **** a pregnant girl it would be the best sex ever
    boobsandbellylover boobsandbellylover 31-35, M 1 Response 19 hrs ago

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    I am 17 years old I always used to dress up in my moms lingerie when I was little then I grew up and started wearing her shirts and dresses then I would wear my sisters close and...
    ascorby54 ascorby54 16-17, T 4 Responses a week ago

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    I'm going to a Halloween party dressed as a cheerleader and my best friend has said he will go as a football player with me. My mum is making the costumes though she is a little...
    YngLee YngLee 13-15, M 2 Responses 3 days ago

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    Thinking of getting a little dress and panties or a girls Halloween outfit
    Mews4you Mews4you 22-25, M 1 Response Oct 16

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    I am a weirdo and I don't care. I like to wear crops and expose my bellybutton.
    T3chmupp3t T3chmupp3t 18-21, M 1 Response Oct 1

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    I dont know why but sex with teenagers, 14-18 is awesome. Something about teaching & showing them your naughty ways in a turn on.
    WhiteGirl702 WhiteGirl702 22-25, F 12 Responses Sep 28

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    I have been doing this for many years running. I'm pretty sure it's expected of me now from all my friends and co-workers. I must admit I look pretty hot as a chick and have been...
    nyloncrush nyloncrush 41-45, M 6 Responses Oct 13

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    For a ddue trust me, they have on many occasions been mistaken for girl legs. They aint over hair or bulky like u'd expect a dude's legs to be becasue im a wuss aha, more like...
    surfdas surfdas 22-25, M Oct 6

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    I really like big boobs, I also have big boobs, who wants to trade boob photos, mine are 38k
    Cleavage5997 Cleavage5997 16-17, F 4 Responses Oct 16

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    We all have wants and needs and desires. We are able to live without them but they are always present and bubbling away in the background. If the world was a bit different we would...
    cuddles1266 cuddles1266 56-60, M 2 Responses Sep 29

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    I message all the time. I just like to have people share their fantasies or real experiences. I have to have a buffer but I will pretty much talk about anything. I am amazed at...
    SueSweetly SueSweetly 22-25, F 2 Responses 6 days ago

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    I have thought about what it would be life to have a women embrace me go down and all of it. I have only been with men and I cant get the thought out of my head
    curiousegirl curiousegirl 22-25, F 1 Response Oct 6

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    So I've had this crush on a guy for a little while and we have talked about doing it but whenever we are together I get super nervous and decide I don't want to but then after he...
    ascorby54 ascorby54 16-17, T 1 Response 6 days ago

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    If love to have a bf that was cool with me ******* other guys.
    Ladyay11 Ladyay11 31-35, F 2 Responses 6 days ago

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    I'm pregnant and am so horny
    Kimb83 Kimb83 26-30, F 9 Responses 14 hrs ago

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    I'm not sure when I first put on ladies underwear but I do remember being at nursery school and a boy said he had to wear his sisters panties because all his were in the wash, he...
    Lingerielover2110 Lingerielover2110 51-55, M 2 Responses Oct 14

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    3 years back and was too shy then....
    jimmy664 jimmy664 22-25, M 6 days ago

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    Any fun ladies in uk wanna chat pm me bk?
    TeddyboyUK72 TeddyboyUK72 41-45, M 4 days ago

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    Talk to me and turn me on, I want to talk to all the older men out there;) so horny!!!
    maddieXxx maddieXxx 16-17, F 11 Responses Sep 26

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    I'm 30 so if you enjoy this age then message me ladies ;)
    heartgun heartgun 26-30, M 1 Response Sep 26

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    So I just wanted to put this out there.... •underage •sub (me) •hand cuffed •pregnancy •fingering •eating out
    ellie1002 ellie1002 13-15, F Sep 28

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    Or become friends with maybe swap pics with any on here
    Steinjoshu Steinjoshu 22-25, M Sep 28

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    Might do it with a guy for the first time this weekend. Obviously I'm kind of nervous. Any advice?
    zacktr zacktr 41-45, M 6 Responses Oct 13

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    send link of any **** movie
    cramasamy1965 cramasamy1965 18-21, M Oct 16

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    My girl needed a ride into vegas one time and she ended up getting picked up by a car with three guys in it and she went down on all three of them on the way to the city
    BigBone90 BigBone90 22-25, M 1 Response a week ago

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    I want it now. The big black co__
    Beachfam Beachfam 51-55, F 2 Responses a week ago