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I Have Crossdressing Stories To Share

Personal Stories, Advice, and Support 404 People

    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


    26-30, M
    2 Responses Jul 31, 2015

    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
    Jun 9, 2013


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

    Dressed In Secret

    Since I was around 16, I have always found lingerie exciting. When I found a huge bag of old clothes (they belonged to my sister) in cupboard in my parents house, I was drawn to trying it on and feeling sexy. I would take time off school to parade around the upstairs rooms in...
    Mrmagoo82 Mrmagoo82
    1 Response Feb 21, 2013

    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

    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
    Jan 28, 2013

    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, 2014

    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
    46-50, M
    Jul 26, 2013

    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

    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
    31-35, M
    Apr 27, 2013

    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
    1 Response Aug 14, 2013


    Hi I'm Kendra. I'm new to this site and looking for some friends
    KendraCD88 KendraCD88
    51-55, M
    1 Response Apr 7, 2013

    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
    1 Response May 23, 2014


    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.
    KatrinaBoyer41 KatrinaBoyer41
    Apr 15, 2013

    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
    26-30, M
    May 20, 2013

    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
    6 Responses May 31, 2013

    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
    31-35, M
    3 Responses Apr 7, 2013

    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

    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
    26-30, M
    1 Response Mar 6, 2013

    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
    2 Responses May 29, 2013

    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
    3 Responses Jul 23, 2012

    Fantasy Desires Of The Heart

    I have about three sissy maid outfits,my ultimate dream is to be a sissy maid to a dom. female or t.g. at one time in my life i paid a pro dom for instructionals,such a turn on to wear black micro mini outfits,ones stocking tops exposed,mincing about in six inch spikes,i adore...
    haremhose haremhose
    51-55, T
    1 Response Oct 10, 2012

    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
    46-50, M
    Aug 16, 2013

    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
    2 Responses Oct 24, 2012

    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
    2 Responses Jul 3, 2012

    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
    1 Response Nov 7, 2012

    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

    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...
    KatrinaBoyer41 KatrinaBoyer41
    May 4, 2013

    Camming Effect (The Ego Boost)

    Since my first story, I've gone on to cam a little more with a few ither guys. It's been a great experience so far. I have been quite willing to jump on a cam when guys request it, and the last time (two days ago) I was fully dressed head-to-toe in naughty lingerie under my...
    mrmagoo2013 mrmagoo2013
    31-35, M
    Feb 28, 2013

    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
    26-30, T
    2 Responses Oct 11, 2012

    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
    22-25, T
    Oct 12, 2013

    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
    4 Responses May 11, 2013

    " 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...
    46-50, M
    May 14, 2013

    Rape Dream

    Hello everybody, I'm Katrina the sexxy 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...
    KatrinaBoyer41 KatrinaBoyer41
    1 Response Jun 29, 2013

    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
    May 21, 2013

    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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