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Thread: Teenage Crossdressing

  1. #1
    New Member ShannonAlexandra's Avatar
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    Teenage Crossdressing

    I know that my desire to crossdress and be feminine came from an early age, and was very strong during my teenage years. I wanted to go out dressed, but never did. So I want to know, did any of you actually go out dressed as a teen, and did you go all out? If not, what was the youngest age you did?

  2. #2
    Gold Member sherri52's Avatar
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    I think I was 24 when I went out dressed. Late at night while my wife was vacationing in Fl with two of our children. Mostly driving but some walking through Boston Commons.
    Put a little lipstick on you'll feel better

  3. #3
    Pantyhose forever! joann07's Avatar
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    For me, crossdressing never crossed my mind in my teens. I started dressing later in life at the ripe age of 37, three and a half years ago. It wasn't until early 2007 when I went out in public for the first time. I was with a very experienced crossdresser and she took me shopping at the mall, thrift stores, and the flea market and then we ate at a mainstream restaurant. It seemed like culture shock, as I was a bit nervous, but I enjoyed it very much.
    After that, I never went back in the closet.

    Hugs!
    Last edited by joann07; 02-17-2010 at 11:26 PM.
    JoAnn

    I love to see a beautiful woman in a nice dress, but then again, I also want to wear that dress.

  4. #4
    Down into the Easy Chair SweetCaroline's Avatar
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    I was a full blown crossdresser by the time I was twelve, so I definitely thought about going out dressed then, but it was mostly an unspeakable fantasy. It took me another twenty years to finally go out fully dressed.
    Caroline Emily
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  5. #5
    Senior Member Stephanie Miller's Avatar
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    Unfortunately I have to fall back on the old saying “If I only knew then what I know now.”
    I denied who I was, and suppressed it behind the McGyver type male. That was until the internet became a main force in daily life. Then I really don’t remember what made me look up crossdressing – but I did. That was about 12 years ago. A time when many of us thought we were the only ones in the world thinking this way. Thinking it was wrong.
    Then the lights came on! Damn I’m mad that I missed all those years of youth and the potential to look pretty.
    Now I get to look forward to picking out a pink walker and wearing my nylons down around my ankles. Better get a chain for my glasses too

  6. #6
    Miss Conception Karren H's Avatar
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    I started when I was 7 and by the time I went out at 16 I was a pro!! lol It was a walk around the block at night in our little farming village.....
    Current Obsession - Breasts and Lingerie!

    .......My Photos

  7. #7
    A California Girl Rachel Morley's Avatar
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    Full on crossdressing (presenting as a girl) didn't really enter my mind much in my teens unless it was for Halloween or some other costume party, but feminizing my boy self like wearing girls tshirts and jeans, earrings, my hair color and styling and some eyeliner .... ah, that's different!
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    The River City Gems - Northern California's largest and most active crossdressing & transgender support group!

  8. #8
    Junior Member sarah_alexander's Avatar
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    Thats a tough one. Dressing since probably 12 or 13 in one sense or another. Full closet by maybe 18. If a walk around the block counts that was it. 31 now, with a rediculous closet and newly single. I am reaching my full potential day by day now I think!

  9. #9
    Member Plasibeau's Avatar
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    I had friends who were into the goth scene as a teenager, so it was really easy for me to go out in skirts to the clubs. Didn't go full tilt dressed though until early 2005.
    My love is god; let's go get a slushie . . .

  10. #10
    Sallee Sallee's Avatar
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    I remember driving to Boston to go out from a town, south about 60 miles. I went to a gay drag club I think It was called the Outside. I even had to get gas I was scared to death, but I had a great time and all the girls at the club treated me great. I was probably early 20's, maybe 21.
    What a kick I became addicted I tried it once and I was hooked LOL
    [SIGPIC][/SIGPIC]Sallee

  11. #11
    Austrian Princess harmony's Avatar
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    i was about 16-living on my own just around the corner from old sigmund freuds house in vienna austria-would he have had a field day with that juicy little girl almost 50 years ago?
    where has all the glamour gone?
    marlene dietrich is my idol

  12. #12
    eluuzion eluuzion's Avatar
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    I began between age 35-40, so I am a Bobby-Buzzkill on this one.
    [SIGPIC][/SIGPIC]

  13. #13
    composed yet compelled Emily01's Avatar
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    yes i did. since my first time dressing was at age 7, it was present all through my teens. fortunately i was late in developing so i could wear my mothers wardrobe all through my teens - and she was a very petite woman!

    so i dressed and went out, usually ~ but not always, at night. there was no fetish activity to it, i simply adored the feelings of it all....walking down the sidewalk with the clickty-clack of high-heels and the motion of the air over my legs and the sounds of the material as i walked .....they were all exhilarating feelings!

  14. #14
    Member Karan49's Avatar
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    This is really going to date me, but...

    Back in 1964, and 1965 when I was 15 to 16 I went out at night (7-9 pm) walking from my home to the local strip mall and walked around. I recall being terrified of being caught or spoken to by a passerby. Then the next year my brother found my stash of clothes and I immediately purged everything. The only thing I did for the next five years was to share my cross-dressing behavior with two women, one a girlfriend, the other my soon to be wife; who I have since divorced in 1978 after seven years of marriage. I did do tons of research in college before I married and told my fiance that the prognosis with cross-dressing was hopeless. There wasn't a cure; and the likelyhood was that it would progress as the years went by. Even with this information we both thought and hoped that marriage would be the cure. Didin't happen. I've been living as Karan since 1988...

  15. #15
    Coulda, woulda, shoulda.. PattiMichaels's Avatar
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    My 1st memory of CDing was from when I was about 4 years old! I guess it was somewhere in my mind ever since then! I would play dress-up occasionally at home when alone, but didn't go out fully for the 1st time until I was 17. I went for a make-up application at a beauty salon on South Street, using the excuse of attending a costume party. I was hooked, but the reality of life set in. Fast forward to when I was 30 and I had a professional make-over and my 1st photo shoot. The cat was outta the bag by then!

  16. #16
    firesoul Byanca's Avatar
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    For as long as I can remember. My grandmother was supportive of me. So I used to steal clothes from my mother and go visit her. Usually pantyhose, skirt and top, sometimes a dress.This was almost everytime I was alone and free to do so. She pretended like nothing and sometimes complemented. Never said something bad. I was there every day.

  17. #17
    Banned Read only nikkijo's Avatar
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    under dressed in HS.. at 15... started by a GF i had at the time... she was 7th grade or 8th and i was a sophmore... she had alot of fun making me up...

  18. #18
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    My earliest memories of dressing is when I was about 6. I dressed through my teen age years, "borrowing" from my sisters. I remember my first outing was at the age of 18 when everyone else was away I took a drive late at night. I even vividly remember the outfit, PM me if you are interested but rmemeber that was 1971. I really didn't go out much until after college when I had my own apartment and my own things but thosse few stolen moments back then in my sisters' things bring back some great memories.

  19. #19
    Junior Member shesgotleggs's Avatar
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    I was fascinated with women's clothes from a very early age.... started sneaking my mother's clothes to wear early on. Started buying pantyhose when I was 16 or so, always said they were for my mother........... Never had enough courage to go out dressed until I was in my 20's.

  20. #20
    Gold Member DonnaT's Avatar
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    I reckon I was about 10 when I first wore a skirt and blouse out of the house, but only to the back yard.

    In my teens, when I had the morning paper route, I'd sometime take a slip off a clothesline on this one dead end street, wear it to the end and back, rehang it, and finish my route.
    DonnaT

  21. #21
    Aspiring Member Nicola2876's Avatar
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    I crossdressed daily throughout my teens but didn't go out until I was 27. This was a half hour walk around the block at 2am after lots of red wine!

  22. #22
    Woman and loving it Jennifer Marie P.'s Avatar
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    Went all out when I was 16 and went dressed fully with my girlfriends and after that I found out who I wanted to be.

  23. #23
    Senior Member Jennifer in CO's Avatar
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    I had been wearing my sisters PJ's off and on since I was 4 or 5 when mom hadn't done the laundry yet or it was very cold out. My sister had an old long sleeved/floor length flannel night gown mom used to make me wear on those nights during the winter or a little short number spring/summer. Past that, my 'real' outting was started by my Aunt when I was 10 and I spent 3 weeks with her and my 3 female cousins as Jennifer. Spent 3 days with the family not as Jennifer but wearing only girls clothes when I was 12. Then spent the entire summer as a girl with my Grand Parents when I was 14. My intent was to transition when I went to college. I started out for 3 weeks wore nothing but girl clothes (pants/shorts/etc - we're talking mountains so it wasn't warm) but during that time I met this girl. We hit it off so I at first toned down the clothes but then I thought this was what I needed to be 'cured' so I quit dressing. It was funny, she thought I was a girl at first and although pretty sure she wasn't a lesbian, couldn't explain her attraction to me. She was very happy when she found out I was a boy. I didn't wear a thing for close to 6 months (except panties) but then I was at her place one evening and we got in a tickle fight and we both ended up wearing the iced tea pitcher on the end table. She went to change and when she came out she tossed me a cute little peasant blouse and a pair of shorts to wear. Once I had them on it was like something turned on in me again. She thought I was cute and proceeded to put makeup on me. Then seeing her finished project got her turned on and the rest they say is history. We got married a year later and that my friends was 33 years ago.

    Jenn

  24. #24
    Casey
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    I have told this story in another thread, but the one and only time I went out was as a teen, or maybe 20. I was home from college and my parents were gone for the weekend. I had been wearing panties and bras since I was about 12 or 13. I had on occasion up to this point, fully dressed with make-up and tried to style my short hair to look more female, all in the protective confines of home. I do not recall what got into me that night, but I decided to go to the store, so i was in heels, a skirt with dark tights, and a sweater. I was fully made-up and had done my hair, and grabbed one of my mom's purses and headed to Caldors (an older version of wal-mart) in the next town over. I was exhilerating walking around the store. I had originally gone to get cigarettes but figured that they may ask for ID so I just bought some sodas and paid. I was so nervous paying that I had to be shaking, and then I stopped in the parking lot for a cigarette and someone asked if my car was broken down or if I needed help. I just sort of femininzed my voice a little, it was dark, and said that I was just smoking and everything was fine. I was a nervous wreck. When I got home I had a difficult time with the garage door opener and I was afraid I was going to have to break back into my house and all my neighbors and the police would see me. So I drove around some more and when I returned, the garage door went up, I parked in the garage, and I never got up the courage to go out again. I am 40 now, and could never pass. Then I was a young looking teenager, short, and thin, with little facial hair...it was easy. But as someone else stated, I can still recall the skirt and sweater more than 20 years later.

  25. #25
    Platinum Member
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    I know my interest began very early in life - preschool age. I wore my sisters panties and pantyhose as a teen, but I was in my early 20's when my wife dressed me up completely for the first time. I never went out, we just hung out together with me entirely en femme. It was incredible!

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