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 370 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

    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

    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

    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

    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

    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

    "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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    Related Experiences

    Last Saturday I put my favourite sexy dress for a night out with my husband. It's a long and rather loose tunic, pink with flowers and rather sheer which I usually wear without...
    amaturelady amaturelady 36-40, F 7 Responses Jun 27

    Your Response

    Cancel
    I would love to have sex with a black women never done it I am so girly right now I will eat eat that p up
    dmedina513 dmedina513 36-40, M 2 Responses Jul 5

    Your Response

    Cancel
    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 1 Response 2 days ago

    Your Response

    Cancel
    Hi my name is Jan I am 21 and have sex with lots of guys. I work at a bar and always bring guys back to my place after work and have sex with them. I have a no condom rule. I want...
    jantheslut jantheslut 18-21, F 7 Responses 6 days ago

    Your Response

    Cancel
    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 day ago

    Your Response

    Cancel
    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 18-21, M 1 day ago

    Your Response

    Cancel
    Yes.. They're just so pretty and I feel lovely all dressed up with a dress on X3
    SammiKitten SammiKitten 16-17, F 3 Responses Jun 27

    Your Response

    Cancel
    What's the name of this dress
    reznikoo reznikoo 22-25, M 1 Response 6 days ago

    Your Response

    Cancel
    I let a girl dress me fom head to toe as a french maid one year. Very emberessing at first but once i got some liquor in me i jad fun with it. The nail polish was a ***** to get...
    staggershine staggershine 31-35, M 2 Responses 1 day ago

    Your Response

    Cancel
    I have a vague idea. I love intelligence and a good sense of humor. But beyond that and a love for video games, I have no specific sense of what I want. I like both long and short...
    jsshado jsshado 18-21, M Jul 2

    Your Response

    Cancel
    About a year and a half ago I was in Atlanta getting a feminization makeover. Makeup, wig, clothes - all of it. It was an all day appointment. I looked good. When we were done, I...
    CDLynn CDLynn 41-45, T 2 Responses Jul 3

    Your Response

    Cancel
    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...
    jmallon764 jmallon764 18-21, M 1 Response 22 hrs ago

    Your Response

    Cancel
    I'm not gay or anything I just simply like how girls clothes feel but all I have to say is that I think it's a freaking curse and I want to break it but I have no clue how. People...
    Zalbaar Zalbaar 13-15, M 4 Responses Jun 27

    Your Response

    Cancel
    I want it but then I don't I like it but I hate it and I know the feeling I should listen to is hate. People say it's who I am but I don't believe it I don't think I was made this...
    Zalbaar Zalbaar 13-15, M 1 Response Jul 3

    Your Response

    Cancel
    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 23 hrs ago

    Your Response

    Cancel
    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...
    jmallon764 jmallon764 18-21, M 1 Response 22 hrs ago

    Your Response

    Cancel
    I have been having sex with my daughters mum for years. I think it's time to stop.
    usernamesareashame usernamesareashame 46-50, M 1 Response Jun 28

    Your Response

    Cancel
    Tell me your sex fantasies
    69dirtygirl69 69dirtygirl69 16-17, F 4 Responses Jul 10

    Your Response

    Cancel
    My dog is the first living thing I've ever had sex with, she was tight, but then I let my friend borrow her and he ripped her a new *******. But moral of the story is, does anyone...
    Guuuu Guuuu 18-21, M 4 Responses 6 days ago

    Your Response

    Cancel
    Message me if you want to talk about sex fantasies
    Crimsonblackrose Crimsonblackrose 16-17, F 3 Responses 2 days ago

    Your Response

    Cancel
    Yep. I do and I like it. So many people on here don't get enough. I just had to say.
    MGF69 MGF69 41-45, F 1 Response Jun 26

    Your Response

    Cancel
    I ran into a good friend that I haven't seen for several years. He went through a long drawn out divorce and dropped out of sight after that. He hasn't remarried and says he's...
    stillhavingfun123 stillhavingfun123 51-55, M 3 Responses Jul 2

    Your Response

    Cancel
    really bad i have been thinking about it for the past month
    Biking6969 Biking6969 13-15, M 2 Responses Jul 4

    Your Response

    Cancel
    I am in high school and this year i really fell in love with my gym teacher and just wanted to have a relationship with him. I just felt i needed someone there to talk to and he...
    soccer2117 soccer2117 16-17, F 1 Response Jul 10

    Your Response

    Cancel
    Looking for transsexual to **** me I have look every where and I'm so horny for it I just want you now :)
    horny4younow horny4younow 22-25, M Jul 14

    Your Response

    Cancel
    Well not a whole change, I want my testicles put inside my body and have a vagina added while I keep my penis... I know this isn't possible but I sure wish it was. And maybe size...
    str8CD str8CD 36-40, M 2 Responses Jul 15

    Your Response

    Cancel
    I have CIDP- I am 21. I was diagnosed last year after being wrongly diagnosed for two years. My main problem is severe pain- it started with pinching feelings in my toes and slowly...
    dobermanlady93 dobermanlady93 18-21, F Jun 25

    Your Response

    Cancel
    Want a black girl to talk sx with me I'm so h-rny
    dmedina513 dmedina513 36-40, M 1 Response 4 days ago

    Your Response

    Cancel
    Want to sx chat with younger girl
    dmedina513 dmedina513 36-40, M 1 Response 4 days ago

    Your Response

    Cancel
    Sunday I was living a dream. My 17 yr old niece has want to go shopping with forever. Even though we couldn't afford to buy anything we headed out for the day and hit a couple of...
    Daniellew51 Daniellew51 51-55, T 3 Responses Jul 8

    Your Response

    Cancel
    Tbh yeah I do even though I'm fifteen I've only been with two guys my ex and my now present. Does this make me disgusting or normal?
    juliahamilton24 juliahamilton24 13-15, F 4 Responses Jun 25

    Your Response

    Cancel
    😱😱😱😱😱😱😱😱😱😱😱😱😱💁
    deteste96 deteste96 16-17, F Jul 3

    Your Response

    Cancel
    If only that was a possibility for me... It's been way too long!
    findingme69 findingme69 31-35, F 2 Responses