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I First Time Sex As a Crossdresser

Personal Stories, Advice, and Support 727 People

    How I Started As A Cross Dresser

    this is a story of me and my one college mate. we used to hangout with each other every day every night. our friendship had no signs of sex. however 1 night as usual we were having drinks and were totally drunk. i dont remember what let to the sex part of the night. while...
    deepikam2f deepikam2f 31-35 Jun 27, 2013

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    When I used to live with my girlfriend at her

    parents back house, I used to wear some of her stuff and check myself out in the mirror. So one day, her dad walked in on me and I was like, ummm... she's not here and walked into the bathroom. Later on, he asked me why I was wearing tights and I told him that I was doing yoga...
    nTights nTights 41-45, M Dec 27, 2013

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    My First Time Crossdresser

    well here ti goes this my first telling my story it all hape it was about 8yr ago i was living just me and had a good job was biying women thing off ebay oh boy i had fun back then on my days off from work i usely dress well one a man frind cam he didnt know i was cd at that time...
    robertw52 robertw52 51-55, M Apr 21, 2013

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    13

    My first g/f caught me when she looked in my bed room window as she cut through my parents yard. She went home then called me asking if I would come over. I got into male clothes, got permission from my Mom and went. I had no idea that she had seen me. She was waiting at the...
    sherrynpantyhose2k4 sherrynpantyhose2k4 51-55, T 2 Responses Oct 8, 2011

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    Best Sex As A Crossdresser

    Ok so this wasn't quite my first time having sex with a man as a crossdresser but it was definitely the best. I had sex with two other men before "Andy" but was largely unsatisfied with the experience and decided to give it another try. I posted an ad on craigslist and got...
    sexykaties sexykaties 22-25, M 27 Responses Dec 25, 2012

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    Can I Have Some Help Please?

    I'm new to crossdressing and I've been dressed completely before but without make-up, also I don't own any of my own female clothes to dress into. I would like to know if anyone can help me to learn how to put make-up on and how to find the courage to buy your own clothes?
    FILL77k FILL77k 18-21 3 Responses May 1, 2013

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    The Urge.

    I had worked hard all week and my friend called and asked if I would watch her house for her that weekend. Of course I said. As soon as I got there I shaved my body and lotioned up, I put on a nice Bra and Panties then a long gown with a pair of 3 inch heels. I was so sexy and...
    deleted deleted 26-30 Sep 5, 2013

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    I Will Never Forget

    My first time with a man was at the age of 14 I have always liked to dress withy mom's clothe. One night I was wearing a lace thong and a white lace push up bra and a pink dress blonde wig There was some people over at the house I was just in my room alone. A friend of my moms...
    deleted deleted 26-30 7 Responses Feb 11, 2013

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    Fist Time Sucking **** In Lingerie

    When I was about 7 years old, I became fascinated by my mom’s sexy underwear. While she was doing chores or getting ready to go out or to work she often wore just a robe over her bra and panties and sometimes when it was warm in the house just her bra and panties all around the...
    barbarascampbell barbarascampbell 41-45, T 2 Responses Jun 5, 2011

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    First Time With My Teacher

    There have been some first time sex as a cd.  But, this is one with my teacher.  It was during a halloween dance we were having.  My girlfriend and I went as soldiers.  Wearing cut off camoflage pants that were high cut like daisy duke almost and matching...
    sexyblackpantyhose sexyblackpantyhose 31-35, M 13 Responses Sep 15, 2009

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    My First Time ****** By A Man When I Was Crossdressed.

    I started out as an Admirer of transvestite girls, dated two of them, and ****** them as the masculine partner. The younger and better looking girl, 5-11, 150 pounds, natural long hair, didn't want me to touch or suck on her boi-clitty, but the older girl, 5-9, 175 pounds...
    NEOCD2012 NEOCD2012 56-60 1 Response Dec 21, 2012

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    How My Childhood Love Became The Love Of My Life

    Hi this is my real life story finally i got the the chance to reveal........being in a family with 2 sister and mother i was less interacted with boys.....i still remember my sister used to dress me like girls i really used to enjoy being a girl......it all started when i used to...
    nagmakhan0111 nagmakhan0111 22-25 2 Responses Apr 9, 2013

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    My First Man.

    Well it happened when I was 13 on a Friday night during the summer. I spent most weekends at my Aunts house and she worked at night on Fridays at one to the Las Vegas casinos. I would go to her house early on Friday so I could spy on her getting dressed for work. She always...
    WILDCD4U WILDCD4U 51-55, M 2 Responses Jun 25, 2013

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    My First And Only Time

    As I've written elsewhere, I am a crossdresser. It started when I was bullied into it at school, but it went on so long that I became used to it and it just became part of my life. I've been using EP to talk about these things for the first time ever, and so I guess I'll now talk...
    deleted deleted 26-30 Nov 16, 2013

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    I'll never forget my first sexual experience

    with another man. I had just gotten my divorce finalized, in my late 20s in a part of the state that was somewhat known for a large gay male population. I'd thought about trying gay sex for a few years, and had recently experimented with a guy in my apartment, although that...
    WillingStudent WillingStudent 36-40, M 2 Responses Apr 30

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    I Had My First Time With A Man, As A Crossdresser!!!

    I had fantasized about being with a man for years... And it actually happened last week!!!! It was one of the most amazing experiences of my entire life. I was extremely nervous before hand but once things started happening, i just rode the ride. It was a lte thursday...
    GoSlowButDeep GoSlowButDeep 18-21, M 8 Responses Aug 26, 2012

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    My First Boyfriend

    I met Tommy when I moved in to my first appartment when I was eighteen, he had helped carry some cases upstairs for me. My furniture had been delivered the day before so as soon as he left I took my jeans off pulled on a short denim skirt over my black lacy panties and a halter...
    Vickytgirl Vickytgirl 18-21, T 13 Responses Aug 22, 2012

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    Afternoon Delight

    My first time having sex as a crossdressser happened a couple of years ago.  I have been a crossdresser since I was a teen, but had never had the courage to meet up with anyone. Finally I did get to know someone locally through internet chats that I got the courage to...
    jaynesissy jaynesissy 56-60, M 1 Response May 7, 2010

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    Downtown

    We moved into this house when I was eleven, and found out a kid my age lived in the house next door . Our house has a swimming pool in the back yard and my folks put a changing tent up to keep people from running in and out of the house in wet clothes when they wanted to get...
    deleted deleted 26-30 2 Responses May 25, 2011

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    How My Childhood Love Became Love Of My Life

    Hi this is my real life story finally i got the the chance to reveal........being in a family with 2 sister and mother i was less interacted with boys.....i still remember my sister used to dress me like girls i really used to enjoy being a girl......it all started when i used to...
    nagmakhan0111 nagmakhan0111 22-25 2 Responses Apr 9, 2013

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    I First Time Sex As a Crossdresser It was 2

    years ago, i met another corssdresser on the internet. We discussed and exchange emails during 2 months and decided to meet in an hotel. I was really nervous, but wanted it to be a perfect time. I got shaved completely, and bought some new outfit. When finally the day came, i...
    melit99 melit99 22-25 5 Responses Jul 20

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    Johnny And Me In The Woods

    Like so many others my first time in girl clothes was on Halloween when I was 13. My friend Johnny and his sister decided I should dress in her cheerleader's outfit for Trick or Treat. So here I am walking all around town in a tiny short skirt knee socks and sneakers. Johnny...
    heathercdinjeans heathercdinjeans 31-35, M Mar 16, 2013

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    In Over My Head!

    When I was 15 I joined a hook-up site (lied and said I was 18) and met a lot of guys. An older one around 50 stood out the most and seemed like the most fun so I agreed to meet up with him just to talk and go from there. I bused down to his house (like 40 minutes away) and he...
    ellebelle18 ellebelle18 18-21, T 9 Responses Sep 11, 2012

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    My First Time Dressed Up With A Man

    I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Crossdresser. Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for...
    jimboz70 jimboz70 41-45, M 1 Response Feb 11, 2013

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    Out On Halloween

    hi my name is luke(aka kim) and this is my first story just thought i should put that out there but anyways lets start the story it started on mid sept when i was talking to a couple of friends about halloween and what we were going to be we started throwing out ideas like...
    sluttysissy69 sluttysissy69 22-25, F Jul 29, 2013

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    Crossdressing For Uncle

    So evry now and then my uncle would sleep over at our house and I would wake finding him humping my ***. I nver fought it bcuzi always enjoyed it. As I grew older we used code words (words I wantto keep discrete) to get in a bedroom and start having sex. Secretly I'd always...
    Ddrmaniac22 Ddrmaniac22 18-21 3 Responses Sep 11, 2010

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    Teacher's Pet

    I taught in an experimental program and was partnered with an older teacher. She was about 60 and I was 45. I'd been crossdressing my entire life and passing since I was 16 but at school it was strictly underdressing: bra/cami and panties; jet black pantyhose/kneehighs; women's...
    josilver josilver 56-60 3 Responses Oct 10, 2012

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    First Time

    By Sara TV **** My first time with a shemale was one summer evening. For several months the city I lived in at the time a lot of transvestites, transsexuals, cross dressers and their admirers would hang out on forth street on Friday and Saturday nights. There were some...
    SaraDoes SaraDoes 61-65, T 8 Responses May 23, 2010

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    Tomorrow My First Time With A Crossdresser

    Hello everybody! I a man who have always dreamed of havin sex with a crossdresser, it turns me on and makes me so horny, so I met this cute crossdresser online, I insisted to meet her, so she said she will call me tomorrow. Im so excited, we talked about sex and stuff, so im...
    deleted deleted 26-30 2 Responses Oct 22, 2013

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    Adonia Reborn

    I had a shemale friend Jasmine. I am 2 years younger than her. I met her when i was 17 (3 years ago). I was wounded due to my rash driving and i was unconscience due to alcohol had on that day. she found me. when i woke up. I was in a black edgy dress. I was get shocked...
    deleted deleted 26-30 Dec 2, 2012

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    With The Boys On The Block

    I grew up in a small town, I would dress in a small shed at the back of my parents property, the boys in the neighborhood would use it for a hang out some. One day when I was dressed having a tea party with my stuffed animals they caught me dressed right down to my moms stockings...
    RunAroundSusan RunAroundSusan 22-25 2 Responses Oct 5, 2013

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    My First Time Sex As A Crossdresser Outdoors

    I have been a crossdresser all my life. I don't advertise the fact that a large part of my persona is feminine but it is obvious. My wife has encouraged me to accept who I am though she doesn't like me to spread the word as it wear. For be part of neing a crossdresser is that I...
    ma465 ma465 46-50, T 1 Response Apr 7, 2013

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    Caught Dressing And Then Dominated

    The first time I had sex as a crossdresser, was when a bi roommate caught me wearing a bikini and jacking off to shemale ****. He took control of the situation, and me, and jacked me off. Then he made me jack him off. What a wonderful experience - being dressed, being caught...
    sissynikkicd sissynikkicd 41-45, M 3 Responses Aug 17, 2013

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    First Time

    i first time sex as a crossdresser when older boy discovered i was a sissy when he debagged me and my pink knickers where on display.he made me suck his **** and swallow his ***.he made me his sissybitch and had to dress in a girl school uniform before he ****** me in my sissy...
    mandiejune mandiejune 51-55, M 2 Responses Jun 18, 2010

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    My First Experience With Crossdessing

    So my first time crossdressing is two parts. My soon to be wife decided one day that she wanted to put make up on me. I was hesitant at first but let her. She through it all on me. She dolled me up, did my hair, i have short hair but she did it as best as she could. So there...
    DillonSmith DillonSmith 36-40, M 15 Responses Jul 23, 2011

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    Was My Second Time As A Man....

    I had been a crossdresser for years, but only in the past few years have I gotten curious enough and brave enough to try sex with another man. To make a long story short(er), I finally got up the nerve and set up a meeting with another man. I worked up my  nerve and went to his...
    RayanneA RayanneA 56-60, M 6 Responses Apr 6, 2012

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    Young & Fun

    I have crossdressed since I was 11. When I was 16, I spent the night at my friends house with the idea of going to the beach early the next day. We really wanted to get drunk and his parents went to bed real early so we had the run of the house. We picked up some beer and a...
    deleted deleted 26-30 2 Responses Jul 20, 2010

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    First Time Sex As Crossdresser

    THEN JUST SEPERATED FROM EX WIFE AND AN EX SISTER IN LAW INVITED ME OVER TO TALK AND AFTER AFEW DRINKS A TOLD HER ABOUT MY CROSSDRESSING. AND SHE WANTED TO SEE. AND THREW HER CLOTHES TO SHOW HER. SHE LIKED IT AND TALKED ME INTO GOING OUT THE NEXT WEEKEND. SO ON FRIDAY SHE HAD ME...
    haileyk haileyk 56-60 Dec 6, 2012

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    Bbq

    This story isn’t really my first but first encounter with this guy After my first time with Tommy he took me to pubs and pubs where I felt comfortable and I met people like myself and those who liked trannies. Any way while I was still wearing man clothes on the outside and...
    Vickytgirl Vickytgirl 18-21, T 3 Responses Sep 5, 2012

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    Sisters Boyfriend.

    Having been crossdressing since I was 5, people who came to our house just never paid attention any more. My sister is 3 years oulder then me a senior in highschool. One day mother was off to work, my sister was dressed and told me her boyfriend Steve would be stopping by. Just...
    femboy4u femboy4u 22-25 3 Responses Apr 15, 2011

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    My First Time With A Real Man

    Iposted an ad as a CD and a picture, I am not at all passable, but I have nice latex mask and chest, with a nice set of 42 DDD **** on it and their soft and pliable, anyway, I got allot of responses, I chose a nice guy that is fit and clean, a closet gay. I made arrangements for...
    deleted deleted 26-30 Mar 14, 2013

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    My Sexual Biography - Part 1 - Includes First Time Sex While Dressed

    So often I am asked what I like to do when I play, do I like being with other cross-dressers, do I date men, how long have I dressed, how did I get started dressing, am I married, does she know, what is my experience, do you like to suck, am I a bottom, do I top, what are my...
    kkane4u kkane4u 56-60, M 4 Responses Jul 5, 2013

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    First And Last While Dressed

    Many years ago I had a fling with a lady at my workplace. I was stunned that she showed an interest in me at all. WOW, she was fantastic. This was the usual girl-guy relationship. Then one time, after we had sex, I was watching her pick out some clothes to wear and noticed her...
    tonkatoy992000 tonkatoy992000 56-60 4 Responses Jan 4, 2010

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    It Is So Painful!!

    I am from Asia! I have a small butt! I knew this lb from a website! We have a short conversation and decided to Meet up! I am fully dressed up like a small ****! We book and hotel in sg! When she turn up she look bold with her body and have an 7 inch and thick ××× when I saw...
    christina8181 christina8181 26-30 Dec 24, 2012

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    My First Sexual Experience While Dressed As A ****.

    I just found EP and am thinking, "What took so long?" Great place to spend a day. Anyway here's the story of how I lost my 'virginity'. It was winter and on my way home from downtown I past an adult theater that I had heard about. It has a book store and small arcade down stairs...
    Corsetboy106 Corsetboy106 56-60, M 6 Responses Mar 23, 2011

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    The Start

    am arab crossdresser , and i started when i was 15 in the school , i used to see my sisters naked in their rooms , and i used to look at them from the hole of the door key , i used to ask my class mate to suck them , and once i wanted to be a girl , i dressed up using my sisters...
    tiyasanjab tiyasanjab 22-25, M Oct 27, 2013

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    My First Time

    I was 17 and a junior in high school.  I was a closet crossdresser, but always wore a bra and panties to school.  I never thought anyone could see the outline of the bra through my shirt.  One day I had a classmate come to me at my locker and put his hand on my...
    deleted deleted 26-30 5 Responses Jan 21, 2010

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    I Got It Backward

    It wasn't until my late teens that I had sex for the first time that I wasn't cross-dressed when it happened. My whole life seems to have been built around doing things differently than others, so why should sex have been any different. My mom dressed me as a little girl from the...
    AmberFountaine AmberFountaine 66-70, M 3 Responses Oct 5, 2013

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    I finally had the courage to by my own clothes

    for the first time, I was scare to do it however, I did it!!
    Stacy1201 Stacy1201 51-55, M 1 Response Jun 29

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    When I was 17 I gave a guy my age a BJ.

    I was wearing pantyhose, and although that was technically my first experience...it was kind of just a building block. I didn't have another experience until about a year later. I was 18. I met a guy on craigslist who crossdressed. He was 25, had a very similar body type as me...
    subcdslut subcdslut 18-21, M 2 Responses May 8

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    First Time As A Crossdresser

    So my first time having sex as a crossdresser was with my girlfriend. I had told her that I liked to occasionally crossdress for sexual thrill and at first she was really nervous thinking about it but after a while she told me that she thought it sounded really sexy and that she...
    cadyshove cadyshove 18-21, M 22 Responses Oct 21, 2011

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    Related Experiences

    I am 20, almost 21 and had sex for the first time with hopefully my first an last girlfriend! I love her more than words can describe. I make sure she know that every day with...
    Corefarian Corefarian 18-21, M 1 Response Aug 13

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    I started dating my bf at 17, we were together til I was 33. I have no idea what it's like to be single. Dating is weird and all I really want is sex. This is the first time I've...
    mlm80 mlm80 31-35, F 3 Responses Aug 6

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