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I Have Crossdressing Stories To Share

Personal Stories, Advice, and Support 410 People

    Sarah Had Fun Away From Home

    Last time I was on a business trip a long way from home I decided to just go for it. I put on a bra, I love this bra, back is normal 2 metal clips but instead of shoulder straps its more like a string bikini, ties behind my neck, totally shows. red matching panties, long blue sun...
    SarahCD707 SarahCD707 51-55, M 1 Response Oct 22, 2013

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    hi my name is Thomas during the day I am a good

    ole boy but during the evening I am Tina. I I live my life as a deep in the closet crossdresser. I even built my own large panic room complete with cameras so I can watch if anyone comes near my home. I have all my clothes sex toys wigs and makeup in there along with a full...
    tom23232 tom23232 61-65, M Jan 7

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    Idk

    My cross dressing started Wen I became Bi. It started as a dare To kiss my friend ( a guy ). Hiss sister dared me ( 2 grades a head of me) to so she dressed me up in her finest bra panties and a dress and I kissed him
    Bicarter Bicarter 16-17, M 1 Response May 5, 2013

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    My Last Crossdressing (:

    last night my sister forced me to dress up as her little sister haha. i wore a bra and top and her prom dress, it was a mini pink poofy dress(: she did my make up she put pink lipgloss on my lips and black eyeshadow long eyeliner and planty of mascara. and some blush.. she...
    SHAY8877 SHAY8877 16-17, M 3 Responses Sep 27, 2012

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    The Lost Bet

    My school banquet was coming up and I was sitting down inside with my sister and her friend. At that point we made a bet discussing something I can't quite remember, but if I lost I would have to attend my school banquet dressed head to toe as a girl and if I won I could have sex...
    Deboss69 Deboss69 41-45, M Jul 26, 2013

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    Round Two

    I went shopping for women's clothes for the second time and it was awesome. I tried on a lot more dresses and even some panties, which I ended up buying. I even tried on some beautiful dresses. Good day for me!
    shadow950 shadow950 18-21, T Oct 12, 2013

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    Crossdressing pick up adventure

    I had crossdressed at our fraternity Halloween party. I looked really good and was quite a hit. The incident was not mentioned again at the fraternity. But a month later a brother named Matt approached me and asked if I could give another brother a some help. Matt told me a...
    Gojohn53 Gojohn53 46-50, M 3 Responses May 29, 2013

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    My First Experiance In Crossdressing

      I just want to share my story. It had begun 15 years ago. I was at my cousin’s house during the winter vacation. We were out for shopping with my cousin. She  is older 13 years then me. I was 13 at that time. She is very attractive woman with very nice hair and body. At...
    nikolol1986 nikolol1986 26-30 6 Responses May 19, 2013

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    First Experience Shopping At A T-Friendly Store

    I just had the best experience in along time. After about a dozen of awkward uncomfortable visit to buy women's clothes in person, I had resorted to buying stuff online. About three months ago I found out about a store specifically for crossdressing and transgendered people in...
    iheartdressing iheartdressing 26-30, M 6 Responses May 11, 2013

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    18 And Dressed To Kill

    When I was 18 I was in a serious relationship with a girl, not any more of course but that's a different story, and we experimented with all sorts. I remember how one night, after a night out, I got her to dress me in her clothes. I wore a short skirt, a boob tube and...
    mrmagoo2013 mrmagoo2013 31-35, M Feb 28, 2013

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    I Just Came Out To My Family As A Full Time Cross Dresser

    Hello all i just turn 25 years and about a month ago i decided to come out to my family that i want to dress like a female full time and all of this is very true.I have been dressing like a female for about 10 years with my family not even knowing.I would dress up when my family...
    fulltimecrossdresser fulltimecrossdresser 26-30, M 3 Responses Apr 7, 2013

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    Trip Gone Bad

    Well it is safe to say that my mom is an neat freik. She is very adamant about not letting me wear the same dirty clothes etc. well I went on a trip with her and she carried her bag on with her but we checked mine. Bad choice!!!! The airline lost my bag! We got into the hotel...
    Duckman1234 Duckman1234 22-25, M 1 Response Mar 6, 2013

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    Driving Crossdressed

    Hi, some years ago I had an extremly nice drive with my car from Stockholm to northern Sweden. It was in the end of May, late springtime. I started in Stockholm dressed up as a femme with light make up, wig, pedicure and manicure... I felt great. It was in the afternoon so I knew...
    marshaanderson marshaanderson 61-65, M 4 Responses Jul 23, 2012

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    My First CD

    I don't remember exactly how old I was the very first time I tried panties and stockings on, but I do remember being very young and takin pics of myself putting things up my tight lil bum with my Gameboy Color lol :). It had always been a fantasy of mine, and got me going harder...
    WetAsTheSea WetAsTheSea 22-25, M May 20, 2013

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    This Is My Story ! Give Me Ur Views ! And Be Free To Ask Or Advise :)

    well, I am a boy 18yp, every one is expecting me to be straight cuz that what I really pretend to look.. but the truth is shared with myself.. with my mirror.. we can say im a crossdresser but only in silent, in secret. whenever i find the chance I go and wear my mom's or sister...
    Secretlovingit2 Secretlovingit2 18-21, T 3 Responses Jul 3, 2012

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    My Cousin

    So It all started one night at my cousins, I don't know why but I walked into her room (She wasn't here) and I started going through her stuff and tried on one of bras and that was it. After that I couldn't not do it. So everytime we went to their house and she wasn't there I...
    Ozzihero Ozzihero 22-25, M Jul 7, 2013

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    Greetings

    Hi I'm Kendra. I'm new to this site and looking for some friends
    KendraCD88 KendraCD88 46-50, M 1 Response Apr 7, 2013

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    Crazy World

    I jus want to let my sexxy lady friends know we're not alone. Latey, I've notice a lot of fat ugly guys dating these outrages hott sexxy women. Yes its too good to be true. Its us and the numbers are growing. Striaght people aren't so striaght. They're either wearing heels or...
    Jedimindtrick39 Jedimindtrick39 36-40 May 4, 2013

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    Crossdressing At Thrift Store

    I read on here that thrift stores were a good place to get female clothes, so today i thought i would grow enough courage and try. I saw a small thrift store near my house and parked in front of it, but started to get nervous and the assistant was looking out the window, but she...
    cross69 cross69 41-45, M 1 Response Aug 16, 2013

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    My Second Story. Crossdressing In The Mall And Reward After That.

    This story happens a few weeks after my first experience during winter vacation in my cousin’s house as I mentioned in my first story. My cousin was and still is very attractive lady. She was my role model especially after I had discover the “girl” side of me. Since that...
    nikolol1986 nikolol1986 26-30 1 Response May 21, 2013

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    A Girl At Heart

    I was a exceeding feminine teen,bullied and beat for only that reason,when ballet class was not enough,i shopped thrift stores for heels,blouses and dresses,early attempts at makeup wefe garish,but i walked around at night,later my aunt helped me dress and do makeup,i kept...
    haremhose haremhose 51-55, T 2 Responses Oct 2, 2012

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    Summer Of Crossdressing

    By the time i was 13 i had been CDing for about 2 years. The summer of that year was particularly intense because i was home alone almost every day for 8 or so hours and my parents were giving me lots of independence. Truly a CDers dream. I should mention that i have a sister...
    13crossdresser 13crossdresser 22-25 Jun 9, 2013

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    Ken

    Funny story, in the 3rd grade, I use to play Barbie with my girl friends. I was Ken. I would try to crossdress him and always tried to make out with Barbie and her friends. Its crazy how something small tells us a little about ourself growing up.
    Jedimindtrick39 Jedimindtrick39 36-40 1 Response Apr 15, 2013

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    Haloween Fetish Ball 2012.

    This years costume will be "mistresses court jester"a specially made black&white body stocking with lacy cuffs and waiste,colors alternate in a harlequin pattern,comprised of sheer nylon.a special appendage for ones penis is included which has a ligature to tie tightly,causing...
    haremhose haremhose 51-55, T 3 Responses Oct 24, 2012

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    One Of My Summer Vacation.

    Since my cousin and my aunt are very supportive to me in my cross-dressing games and experiments I was very eager each summer to have as much as possible time , spend in my cousin’s house. I was lucky because my cousin was already a student in medical university and she was...
    nikolol1986 nikolol1986 26-30 1 Response Jun 2, 2013

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    Skiing In The Alps

    Hi I love skiing. I do ski as often as I am able to. Some years ago, I went to the alps with a friend of mine for skiing. He was aware of me as a crossdresser. I decided to crossdress all the week in the alps. In the morning, at the hotel, I went for breakfast in thights, a...
    marshaanderson marshaanderson 61-65, M Aug 29, 2012

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    Getting Towed In DC

    Sometimes I don't pay attention to important things and it comes back to bite me. I was in Washington DC in the summer of 1987 and decided to visit museums in the Mall area. I wore a flowery dress, a pink bra containing two water balloons, a wide brimmed hat and high...
    Robertredlips Robertredlips 56-60, M 1 Response Nov 12, 2013

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    Fun Crossdressing

    My wife likes me to crossdress. We sometimes go out to a movie theater while both of us are wearing panties and stockings. Its literally hard to sit through a movie as I am squirming in my panties and stockings. A few times we have went during the day when few would be in the...
    pantiescouple pantiescouple 26-30 Jan 28, 2013

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    My Husband's First CD Date.

    We live a fetish lifestyle, as you can see from my profile. I am a Hotwife, and love to swing, dating as many hot guys as I care to. My husband is now my Cuckold, he chose this lifestyle as a favor to my love for swinging. he obediently awaits my return to the house where he is...
    dangergrrl4u dangergrrl4u 51-55, F 12 Responses Oct 14, 2013

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    I Have Crossdressing Stories To Share

    Years a go one of my uncles was visiting and we ended up talking about crossdressers I got brave and told him that I crossdressed later that night wife was gone and kids were asleep and I got all dressed up in a very short dress with pantyhose on had my makeup on and came out...
    deleted deleted 26-30 1 Response Aug 14, 2013

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    My Crossdressing

    i have been a fond of wearing sarees from my childhood age . my chachi used to wear me sarees from young ones and do makeup like apply lipstick on lips and sindoor on my maang. i am fond of crossdressing from class 7. in class 10 during my vacation when my buwa and i was alone in...
    kannust kannust 18-21 May 21, 2013

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    Love Dressing Up

    i have been a long time lover of womens/girls clothing and have dressed up quite a few times. my crossdressed outings have always been to areas where no one knew me and at night as i am not the most feminine looking person just in my mind when dressed. this weekend i was getting...
    kristy61 kristy61 51-55 1 Response Nov 7, 2012

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    Bbq Crossdressing

    At my last BBQ my friend was talking about her and one of the other girls were the only ones wearing dresses, and how i chickend out of wearing one to, i had had a few so i went to go get dressed up, i came back to the party in all my crossdressed gear. No-one could believe how...
    DanniChan DanniChan 22-25, T 2 Responses Oct 11, 2012

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    I'm 52 and have been hiding my true feelings

    all my life just doing what the world expects a man to be. I so wished I would have had the courage to come out when I knew in my heart so many years ago. We only have one life and we should embrace it and be who we feel happy as. I am luck in the fact I have a supportive...
    alexistransgirl alexistransgirl 46-50, T 2 Responses May 23

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    Crossdressing Experience

     I had crossdressed a few times and built a desire to do so more, and in public. As a boy growing up it was hard to find opportunities. I would dress privately and wait for the next time. My next opportunity was for Hallowen. I told some friends I wanted to go as a girl, as I...
    TaraJaden TaraJaden 36-40 8 Responses May 31, 2013

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    I Have Had Such A Busy Life These Past Weeks As A Female

    I have to tell yea since i have come out to my family and my work i have been very busy dressing like a female.I have not had such great support from my sister and the ladies that i work with.I have also have gone out to lunch with the girls that i work with.My sister sometime...
    fulltimecrossdresser fulltimecrossdresser 26-30, M Apr 27, 2013

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    " A Night To Remember "

    First of all, I must say that the story your about to read is 100% True. So late last year my sister, Bellea called to inform me that her and her husband of 10 years where seperating. I wasn't to surprised due to him being a complete tool, and a looser. She also goes on to say...
    KAMMII797 KAMMII797 41-45, M May 14, 2013

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    My First Story...

    Recently I've been sneaking about dressing in my wife's clothes when shes not about. We're about the same size, some of her things are just a little too small for me, but shes a sexy girl with a large wardrobe - so there's no shortage of sexy outfits that do fit, for me to pinch...
    Roomz Roomz 26-30, M 2 Responses Feb 4, 2013

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    Rape Dream

    Hello everybody, I'm Katrina the sexxy Jedi.lol I got a serious story about me. I was really young and small. I had nightmares of guys rapeing me. Sometimes, it scares me to see striaght guys hitting on people like myself.They always say dreams come true and I hope this never...
    Jedimindtrick39 Jedimindtrick39 36-40 1 Response Jun 29, 2013

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    Innocent Crossdressing Game During Thanksgiving, Which Help Me To Introduce My Woman Side To My Parents.

    Since the summer was gone and I was back to my normal routine I was dreaming for the next opportunity to get dressed as girl. Thanksgiving vacation gave such opportunity and more then I was expected. Somewhere around thanksgiving we all had plans about family reunion in my...
    nikolol1986 nikolol1986 26-30 2 Responses Jun 16, 2013

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    I Have Fantisies That "Could" Come True

    I allready am a CD& wife helps me with that-She enjoys wacthing men with me (allmost) as much as I enjoy her with other men! My fantisies(& wife is game) go like me being taken in the back seat-even with wife behind the wheel-Out in public-fem me being groped-skirt/dress being...
    jettys jettys 56-60 3 Responses Aug 24, 2013

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    Tons!

    just ask away and ill share all my stories, what do you want to hear about first? :)
    glasscitycd90 glasscitycd90 22-25 1 Response May 3, 2013

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    Crossing Over To Her

    When me and my wife first got together everything was ok, it wasn't bad and and wasn't good either. About four years into our marriage I told her I loved dressing in woman's clothes, unsure of her response at first I was nervous and one day when I was getting out of the shower...
    1 Response Jan 25, 2013

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    Related Experiences

    I'm so f***able I promise god I love a good story and I have plenty to share
    Rltdancer Rltdancer 18-21, F 4 Responses 6 hrs ago

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    if anyone has read my most recent story you know i got the house to myself for 2 weeks and have been girly the entire time its perfect :) but i have noone to share this great...
    dawncutie dawncutie 18-21 7 Responses Aug 6

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    Every time I login to EP n read others stories. I feel there are so many people in this world and every person seem to have their own little story. Every person have their own...
    stuckinlife247 stuckinlife247 26-30, F Aug 8

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    But only for those of you who would like to chat, I have many to share
    tonimino10 tonimino10 36-40, M 1 Response Jul 30

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    In my younger years I never ever thought I would be attracted to a white man...how now..when BLACK DON'T CRACK....OR ONCE YOU GO BLACK YOU NEVER GO BACK but since last year I have...
    CurvyandChic CurvyandChic 22-25, F 9 Responses Aug 6

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    I hate to admit it,I have been with a great strong man for a long long time now.however I have had my share of expirence in the area but since being with him almost 7 years..there...
    petitelady28 petitelady28 22-25, F 2 Responses Aug 10

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    Yes I am, and yes they are. I don't have to lie about myself and bullshit in my stories, because I don't want to meet the requirements of other people. I'm here, because I want to...
    Atko79 Atko79 31-35, M 3 hrs ago

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    I was caught by my mum a few months ago. I was wearing some of her lingerie black tights and black heels strutting around the house. I didnt hear her come in and i turned around...
    tomcd95 tomcd95 18-21 3 Responses 2 hrs ago

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    I'm horny and rubbing my cl*t. Leave me stories in my inbox
    tmacks tmacks 22-25, F 3 Responses 6 hrs ago

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