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I First Time Sex As a Crossdresser

Personal Stories, Advice, and Support 777 People

    My First Shemale Experience

    Hi thanks for the opportunity to share this storey. I was in a coffee shop in Toront about 10 years ago reading a local paper called the Eye. I noticed the ads for adult entertainment and saw transexuals listed. I thought wow, I would like to try this. I have know for a long time...
    lisalyons lisalyons
    56-60, M
    1 Response Sep 12, 2012

    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, T
    1 Response Dec 21, 2012

    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
    3 Responses Sep 11, 2010

    I fantasies about this all

    so no I haven't done it every time I start to play with my self I cannot thinking about having a cd joining in and tuching me all over in my stocking and sexy under wear and to do the same thing back
    deleted deleted
    1 Response Jun 12, 2015

    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
    1 Response Jun 5, 2011

    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
    10 Responses Sep 11, 2012

    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
    Dec 24, 2012

    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
    56-60, M
    Apr 21, 2013

    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
    14 Responses Aug 22, 2012

    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...
    56-60, M
    3 Responses Jun 25, 2013

    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
    46-50, M
    Dec 27, 2013

    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
    36-40, M
    Mar 16, 2013

    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
    22-25, T
    3 Responses May 1, 2013

    I'm still waiting to have my first time sex

    as a cross dresser I think about it all the time now I much be reedy for it so yes I cannot wait for that to happen
    deleted deleted
    1 Response Jul 5, 2015

    I was 14 and drunk and I was unsure at the time

    I was at a party and whent to bed some time after I got woke up, I had a **** in my face and I was getting sucked on, he said its ok. So I started to suck him too it tasted nice but he wanted sex so I said I needed the bathroom but ran home instead. A few years later when I was...
    justacd justacd
    18-21, T
    1 Response Mar 24, 2015

    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
    Mar 14, 2013

    First Time Out

    My first time was after my divorce. I had dressed for a long while behind my familys back. I was in my own apartment and was really horny so I put a ad on cl. I had a couple responses and one that wanted to no if we could meet that night. We set it up and I showered and started...
    grtg grtg
    7 Responses Aug 10, 2012

    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
    2 Responses Feb 11, 2013

    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...
    deleted deleted
    10 Responses Jul 20, 2014

    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 all started when i used to...
    nagmakhan0111 nagmakhan0111
    1 Response Apr 9, 2013


    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

    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
    10 Responses Sep 15, 2009

    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 all started when i used to...
    nagmakhan0111 nagmakhan0111
    1 Response Apr 9, 2013

    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
    1 Response Jun 27, 2013

    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
    5 Responses Feb 11, 2013

    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
    2 Responses Jul 20, 2010

    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
    26-30, M
    Oct 27, 2013

    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
    2 Responses Oct 5, 2013

    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
    41-45, M
    2 Responses Apr 30, 2014

    When i was around 12

    and discovering my sexuality, i use to go to my best friend's place and we were going thru his mom lingerie collection.(teddy's, babydolls, stockings, sexy costumes) and trying them on. After choosing what to wear, we were getting ourself horny by rubbing our buldge on each...
    Uphilthis Uphilthis
    41-45, M
    2 Responses Sep 5, 2014

    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
    5 Responses Apr 6, 2012

    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
    3 Responses Jan 4, 2010

    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
    Jan 21, 2010


    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
    1 Response May 25, 2011

    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
    22 Responses Dec 25, 2012

    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
    2 Responses Oct 22, 2013

    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
    26-30, F
    Jul 29, 2013

    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
    Sep 5, 2013

    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
    56-60, M
    1 Response Jun 29, 2014

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

    I was wearing pantyhose, and although that was technically my first 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
    22-25, M
    2 Responses May 8, 2014

    My frist time crossdressed was with my mate

    who I won't name it was so funny though because I walked to his house at like 1am wearing a corset with surpender under my boy clothes. So I got to his house now had to sneak up stairs trying not wake up his mum and dad got in to the room now and took my dress and heels...
    missjazzmin missjazzmin
    1 Response Nov 10, 2015

    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
    12 Responses Aug 26, 2012

    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

    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
    1 Response Apr 15, 2011

    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
    Nov 16, 2013


    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
    2 Responses Sep 5, 2012
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