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Thread: When did you first crossdress?

  1. #876
    Aspiring Member Sarah-RT's Avatar
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    When I was 5 or so my sister dressed me in her communion dress for a laugh, hated it simply because of sibling rivalry but I recall my mom putting lipstick on me as a joke which I remember finding fun but I wouldn't relate it to crossdressing.

    I was at my god mothers one time and she asked would I tidy up her kids playroom for 5 pounds(dollars) which I did and found a blonde wig which I wore doing it, I remember being afraid her or my mom would catch me doing it.

    Around 6 or 7 I had a female friend who was my best friend since we lived in an area with a lot of older families with few young children and I remember she gave me a make over one time which I enjoyed but had no idea why, years later she had moved away and I stayed the weekend once and she did ballet and thought it'd be fun to let me try on her ballet clothes which then I knew I'd enjoy doing.

    As a young teen my mother got married and I got a step brother and sister slightly younger then me and she'd often dress the two of us up which I definitely liked doing and my step brother didn't.

    My first girlfriend was my step sisters friend and I told her about my dressing because I had learned what crossdressing was and wanted to do it, she bought me a corset and a mini skirt for 1 of my birthdays as well as gave me some of her old clothes. She seemed supportive but I never really dressed in front of her more then once or twice.

    A funny story was we were making out on her couch one time and she put lip gloss on me, later she went into her kitchen and her sisters boyfriend asked her was she painting her face with lipgloss because she had it all over her cheeks and forehead and that I was hardly wearing lipgloss. We had a good laugh over that.

  2. #877
    Member Lisa LIckorice's Avatar
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    My younger cousin would always wear women's heels and nightgowns. My favorite aunt thought it was so cute and he always got a lot of attention. I'd sometimes slip on a pair of heels if they were laying there, but started dressing at my grandmother's home after school. I would go there after school while both she and my mom were at work. I'd be there alone for probably two to three hours per day. I remember the first time I slipped on her pantyhose! That was the first time I remember getting a hard on. My grandma had a lot of money and a ton of lingerie. Closets and closets full. She had maybe three hampers filled to the top with pantyhose! That is where she stored them because she had too many pairs for her drawers. It was a sissy heaven. After that I found the key to the "special closet." Grandma was a freak! She had dildos, strap ons, whips, handcuffs, etc. I started experimenting with her toys. I'd do my best to clean them up, but she knew what I was doing. I remember one December I got into the closet and there was a wrapped box with my name on it. I opened it up and it was my very own bright pink dildo. We had a talk about it later and after that I'd often go to Dillards and Macy's with her and she'd buy me lingerie. She was a queen and let me be a princess, never telling my mom or dad. Love you grandma!

  3. #878
    New Member JessicaFoxx's Avatar
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    I first started when i was 16 we had a closet that stored extra clothing, and there was a women's dress being curious i decided to try it on and it fit, well i started going in the closet more often so i could wear it and it made me happier, so then we moved, and the laundry basket moved into the bathroom instead of the hallway and i would wear my moms and my aunts clothing (I know they were dirty but I was going to be cleaned soon) well that was a everyday thing. then when they would go into town for 2-4 hours i would go in their drawers and wear their clothes around the house. I guess that's how it started with me

  4. #879
    Junior Member MsLana's Avatar
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    I played dress up when I was a kid with my older girl cousins a few times .I was maybe 6 or 8 yrs old.I don't really count that though. it was just fun kid stuff.Fast forward to adult life.I was in my late twenties , going thru my "cougar" phase ( before the word was fashionable)..I was living with a woman in her late 40's..worked in a hair salon and styled wigs on the side. Well , her partner and her started using me as the "wig head".We would party and they would style wigs and it was fun.One night they got the idea of dressing me up etc with make up and the whole works...it was just another fun kinky thing to do.Well , they then got the idea of me going out with them dressed!!!..WHOA!!! hold on sister..."aw come on it will be fun"..sooooo...I said just this once...they got me all dolled up and away we went..to a club which I think catered to CD and was pretty laid back actually. I was hit on continuously!!!...one guy bought me a damn rose...and they wanted to dance..the part I was digging was the drinks they were buying us..we did this scenario several times after that and well, it just kinda grew on me I guess...I passed very easy in those days..I am only 5'6" and was thinner then (of course) so it was quite a thrill to say the least.Now I am content to have playtime at home and the need to "go out" is not a burning desire....It's very therapeutic to me to be able to get dressed and just hang out at home in what ever I want to wear and be comfortable.

  5. #880
    New Member Kathleencd's Avatar
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    I was about 14 when I started wearing my sisters bra and panties.

  6. #881
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    I was about 12-13 years old when I found some clothes someone had given us but my mom couldn't wear them. There was a bra 34d faded pink and a 1 piece swimsuit black with gold trim, tried them on and loved them. I had them until I went into the military.

  7. #882
    Member Michelle_G's Avatar
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    It seems like its been forever but I must have been in the 7 to 10 range. I remember trying on my mom's pantyhose and I was hooked. It was such a thrill I looked for more things to try on. I found her swimsuits and some old dance leotards she had in a closet. I still remember the leotards were the best . Both were black ,one was a soft stretchy cotton material with a scoop neck. The other one was more of a shiny nylon material and had a back zipper. I would sneak the pantyhose and the leotards into the bathroom to try them on.

  8. #883
    Living between the lines
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    I agree it's been a long time since the first time. I remember trying on clothes of a friend's sister. My favorate dress believe or not was a shiney, shimmery gold dress. I played the part of his "girl friend" and he had to asked me out. We would lie on the couch, kiss and make out. It later grow to wearing my mothers panties and underwear. I remember when she caught me with all her clothes in a bag. I told her it was for Halloween and I was to play the "girl friend" of one of the guys. "It's a prank mom!" Really I want to wear it and be that person that wanted to come out. She wasn't happy and a bit confused I was cught and disappointed. I kept dressing even from my teens. It has been off again on again and now it's out there. Ive purged in the past and lost out on some great outfits. Now it's all in and fun. It's part of my life and part of who I am. It's trying at times for me. I have to see is it me or the person people think I am. Today I find woman very attractive and desirable. But at the same time... I appreciate the attention of a man when I dress. It's a completely different feeling as a woman. I get excited when a man holds me tight.
    Go through life being yourself with your head up and your heels and standards high

  9. #884
    New Member Riddhima.mehra's Avatar
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    I was 10 then & I wore a bra. Unfortunately, I was not able to close it; since the buttons were at the back.

  10. #885
    New Member melaknee's Avatar
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    playing dress up with 3 sisters when i was probably in 3rd grade. they were a bit older than me. heehee it's true

  11. #886
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    I was around 12 when I first played with my older sisters clothes. Primarily it was her nylons panties and bra. I would wear them during the day when I was alone in the house. I think I was 13 the first time I wore a dress. It was Halloween and I went as a girl. I wore a dress and some makeup and since I didn't have a wig I wore a scarf. I remember going to a young woman's house that worked where my dad worked. She invited me in and was all complimentary. I often wonder if there was something I missed out on.

  12. #887
    New Member Ms.Kenadie's Avatar
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    I got scared one night and slept on the floor in my Grandmothers room. I guess she hadnt cleaned up before she went to bed. There were a pair of pantyhose and panties. I was about 6 or 7. Been in love with the feel of pantyhose, panties, and lingerie ever since.

  13. #888
    New Member vickie1952's Avatar
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    I started dressing at about 16, i'm not sure now why but it just seemed natural to me and i still love the feeling.

  14. #889
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    At 5 or 6 a would swap shoes with girls under the table at primary school.
    7 to 8 I could get into the pretty yellow bridesmaid dress in the play box at home and would hide it in the toilet then go put it on when no one was about.
    In early teens I painted my toenails and borrowed my sisters tights, bra, skirt and boots and dressed in the local park toilet then delivered my papers before I changed back and went home.
    The urges got stronger from there onwards, the rest is history.

  15. #890
    New Member girlbh44's Avatar
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    I think I was about 10. I was at grandmother's and my little sister wanted to play dress up so I did too.

  16. #891
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    When I was about 4, maybe because the weather at my place was really hot, My mom then put me in one of her tank top. I can not forget the felling of the fabric.
    Maybe that event was the reason why I am always attracted by women's clothes.
    Long time later, when I was already in high-school, then I had a lot of chances to put on my Mom's bras and panties that she left in bathroom.
    I have been married for 2 years. And now I can have my own wardrobe which was selected by me and my wife. I even have more bras than her .

  17. #892
    Senior Member Ceera's Avatar
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    For me there is a big difference between "When did you first try on women's clothing?" and "When did you first underdress or want to put on a complete female outfit and appearance?".

    When I was something like 8 to 10 I know I tried on some of my mom's clothes in the privacy of the laundry room. Tried it on, looked at myself in the bathroom mirror, and took it off again quickly. But back then I wasn't about to try wearing her panties or bra under my clothes, or spending any length of time wearing any of it. And I certainly wasn't considering putting together a whole outfit, with or without a wig and makeup. I think I stopped trying on her stuff well before I started high school.

    I knew by the time I finished high school that I was probably bisexual, but I suppressed that too, because I also knew my dad was homophobic.

    It wasn't until I was in my mid 50's, after the death of my father, that I decided to try wearing panties or a corset, and purchased some for myself. Back then, I'd been writing fiction for 5 to 10 years that included some characters that were gay, lesbian or transgendered. And in one of my recent stories there was a young male who was experimenting with crossdressing. I wanted to try wearing panties and doing tucking, at least in part to better describe the feel and the process in my stories. But I also realized that my wanting to write those stories was probably an indication of some desires on my part that I had been denying all my life. With dad gone, I no longer had to fear him finding out. Kept it in the closet, though. I underdressed with panties full time, and admitted wearing the panties to my wife and daughter, but kept my small duffel bag full of a wig, my corset, women's clothing and one pair of shoes that I had collected over the next six months my secret. I doubted I would ever do more than dress at home, though I admitted to myself I wouldn't have bought the shoes unless I had some intent of trying to leave the house while Dressed.

    A couple of years later (about a year ago) was my real turning point - when I would say I really started crossdressing, at age 56. My wife had also passed away, and I decided to actually buy some full outfits and some good wigs and makeup and prepare myself for actually going out in public in female mode. I came out to my daughter and soon half my closet was girly stuff. I have more makeup and girly clothes than my 19 year old daughter has! And for the past 6 months or so I get out 3 to 4 times a month in female mode!

  18. #893
    Junior Member CDRMolly's Avatar
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    When I was 2or3 my aunts would play dress up with me(Iv'e seen pictures,I made a cute little girl),at about 12 or 13 I started trying on and wearing my sisters clothes-panties,bras,pantyhose,girdles.Wore some on and off for years until the last five or six years the urge really took off,and now in my 50's and enjoy it more than ever.

    Thanks,
    "Molly"

  19. #894
    Discovering the Gurl Xandra's Avatar
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    I have been away from the site for a while but have so enjoyed reading the replies and the stories. Please keep them coming!

    Xandra xxx

  20. #895
    Junior Member Amanda77's Avatar
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    Thr first time wow, what a feeling. I was 12 and looking for something in the closet i came across a box full of my sisters old clothes and underwear. I just looked through the first time then a day or two later i whent back to it and took a training bra and panties to my room and slipped them on. I have no idea what compelled me to but like i said wow, it felt so good. a few days later it was bra, panties, and t-shirt and shorts. I'll never forget that day.

  21. #896
    If only dreams came true. susancheerleader's Avatar
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    Does wearing my sisters one piece swimsuit and gymnastics leotard count? That was the first garment I wore at about the age of 13.

  22. #897
    Member Kathrine's Avatar
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    When I was about 5 I used to sneak into my sisters room and try on a brown fake fur coat she had. I loved it, it had brass buttons on the front. My Dad caught me one day and told me it wasnt for me. I didnt wear female clothes again until about 12, when I started trying on my sisters clothes.

  23. #898
    New Member SonjaThompson's Avatar
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    I was about 13/14 when I first tried on a pair of tights (pantyhose for US types), mainly because I really fancied women who wore them and I was curious. I tried this a number of times, and tried a pair of knickers and bra on once, felt ridiculous and then didn't bother at all until about two years ago. My wife was away for a weekend and I suddenly decided to try on some of her clothes. I ordered a wig, shaved my legs, and the rest is history. I honestly have no clue what prompted me, but I am happy I did.
    Sonja Thompson - Part time TV from Lancashire, UK

  24. #899
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    Don't know the exact age. but around 10-12 years old. Wore my mom's lingerie and sister's panties. Fun!

  25. #900
    New Member Satwiwa's Avatar
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    a few times in my 20's.. in my 30's I had the good fortune to have a Friend stay with me & my house mates for a few weeks. she brought a fair amount of clothes and they were kept in my walk in closet. once she went back home, she had mistakenly left behind some of her clothes. she didn't pick them up for almost a month. in which time I wore many of them - mostly her bras, panties and the bright Pink silky Negligee. I would put them on in the evening, lay around in my bed and often feel asleep wearing them. They felt soo wonderful and sexy. I took very good care of her clothes while i had them. I felt sad when she finally picked them up.
    I loved that period and it certainly allowed me to be myself and start wearing women's clothing...

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