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Thread: when did you start cross-dressing?

  1. #76
    Aspiring Member tommi's Avatar
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    I was very young and it started with mothers pantyhose mom thought
    it was cute even dressed me for halloween a coupl of times as a little girl,always in boy underwear I had her cedar chest and extra dresser in my room that she moved her summer clothes and winter clothes to and from
    my bedroom was upstairs hers down left alot of things available. Was caught
    wearing one of her halter tank tops at 15 hadto do some quick explaining.
    Looking back I now relise how lucky I had it.

  2. #77
    New Member j_hewish's Avatar
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    the first time was when i was 8 years old. it was a gym kit belonging to my neighbours daughters navy panties bottle green skirt and a white blouse since then my tastes have improved.

  3. #78
    Member Jenny Wilson's Avatar
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    I was about 10. I was an only child so all I had to work with was mom's stuff. I started with panties and added a girdle and stockings. Then it made sense to add shoes and a dress. Her bras wre too big for me, not that she was a big woman (she's a size 10).

    I had always been intrigued with my cousins' stuff. I had a lot of older female cousins. but I never had the chance to try their things on. At the time, I wished they would have dressed me up in their stuff when they were babysitting me, but it never happened.

    Jenny

  4. #79
    Senior Member lauraabdl's Avatar
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    I was about 7 or 8 when I started. My sisters panties and nylon tops. What a memory of those days. Mom found out and was beside herself on what to do so she did nothing and did not tell my dad.

  5. #80
    Guy in Skirts and Heels notquitegirl's Avatar
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    I was probably about 4 or 5

    I don't actually remember. I do remember running around my apartment building in my sister's friend's nightie and tights at around 7 or 8 years old, however, just part of a lifelong love of wearing skirts and pantyhose/tights out and about.

  6. #81
    Junior Member franvonceder's Avatar
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    I started when I was about 11 years. Used my mother's bras and girdles - that gives you an idea how long ago it was!

    Fran.

  7. #82
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    10 years old mums stuff

  8. #83
    Member Jena11's Avatar
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    When I was 5?

    Well, I know that I would play dress up with a girl that was my only friend when I was in 1st grade and Kindergarden. We would put on her dresses and shoes and necklaces. Then when I was in 3th grade, I tried on one of my mom's bras. She worked and was not home. It was a dare from some other boys. They then told others at school, I then did not have any friends or really talk to anyone. I knew before then that I always wanted to be a girl. I was too afraid to tell my mom. I then would dress in her clothes sometimes when I could. I then got lucky that she got rid of some old clothes. Well, I got my hands on them before they hit the trash. I had some pantyhose and a full slip. Then when I was in 6th grade, I got a dress and a bikini that she was getting rid of. My mom did give me a pair of pantyhouse to wear when we went skiiing so that was great. I did not like to wear ski pants so I would wear jeans. I always dreaded Halloween, I could never tell what I wanted to go as. I really wanted to go as some girl thing but again was too afraid to tell. It has just continued from there on the rest of my life. Jena
    Jena

  9. #84
    Member Peggy55's Avatar
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    Age 50 for me. Just recently. Someone should start a poll!
    [SIGPIC][/SIGPIC] Peggy

  10. #85
    Junior Member PatyR's Avatar
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    This question made me think

    I was browsing this forum and I wasn't sure that I wanted to register, but this question made me decide that I want to share with someone similar to me.

    The first time that I crossdressed, if it is valid to say so, was when I was very young, maybe about 8. I used my cousin's panties and I felt great. But I don't feel that this was the day that I really started.

    I really started about 12, using my mother's clothes, particularly one beautiful purple dress, her bras, pantyhose, and high heels (really they weren't to high but I felt them huge). Then it came my mother's bathing suit, of course with pantyhose and my high heels and finally I dressed up with skirts, blouse, bra, pantyhose, and full make up. All of this was done secretly and for long time. then we move to a different house and my mother didn't work as much as before and it had to stop.

    Lately, things changed. I got married and my wife knew before our marriage that I enjoyed to Crossdress, so sometimes she let me crossdress while at home. Unfortunately, since I move recently to this region, I lost my stuff, so I'm on my way to recover what I lost.

  11. #86
    Diane Lee TV Wannabe's Avatar
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    I think I was 13 or 14, and my mum was going to throw away a pair of black pantyhose, for some reason I had to try them on. I just recently started doing it again now with my own things.

  12. #87
    Kate NighttimeGirl's Avatar
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    i was six when i started to explore the real me and it is a good memory to look back on thx for reminding me babes
    Kate xx Home at last

    "Used to be a sweet boy
    Holding so tightly
    To Daddy's hand
    But that was all
    In some distant land"


    Morrisey

  13. #88
    Member Tiana's Avatar
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    around 8 or 9 i think but the urges did not really come out till i was around 15 x
    OFF TO GET MY NIGHTDRESS ON

  14. #89
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    i WAS ROUND 12 JUS STARTED SEVENTH GRADE. aFTER MY PARENTS WENT TO WORK I WENT INTO MY OLDER SISTERS ROOM TRIED ON A PAIR OF HER PANTIES, A PAIR OF BLUE JEANS, SOCKS, SHOES, A BRA, A SHIRT AND A WIG i LOOKED IN THE MIRROR i THOUGHT i LOOKED GOOD SO i DECIDED TO WEAR THE STUFF TO SCHOOL. lUCKILY MY PARENTS WORKED TILL SEVEN BUT WHEN i GOT HOME FROM SCHOOL mY SISTER WAS ON THE COMPUTER DOING HER HOMEWORK SO SHE CAUGHT ME WEARING HER CLOTHES. So shes the onlyone that knows we go shopping together and hang out as sisters.

  15. #90
    New Member JENNYgirl's Avatar
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    I started at 13 when my to older sisters dres in hose skrit and blouse veryone thought it was fun but i got hang around the house for awhile dressed love the feel of hose on my legs than and still do it was til i got a divorce that i real got start and bought some spike heels hose bras panties and get to live on the weekends the ex would take the kids

  16. #91
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    when

    about 5. b4 sis was born, dad said "going to turn you into girl" started wearing moms clothes to practice. got caught. big laugh. started again about 10. got caught at 13. lots of fertilizer spraying.

  17. #92
    Hugging the Kurves! RobertaFermina's Avatar
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    I got into my roommates panties, and dressed for Halloween at the age of 20.

    I might have dressed sooner, but, as a foster-child, the fear of being sent from the foster home for such an intrusion (non an uncommon result, in my experience) kept me from wandering into the foster-parental room and through the drawers. Plus my relationship with my foster-mother was one of awe and fear, not intimacy or nurturing.

    I dressed occasionally for Halloween or special Parties, maybe 6 times over 25 years - not much.

    I went to BurningMan again last year, and took the wig and some skirts and blouses, and the encouragement of my S.O. I dressed 4 nights running and <pop> I got hooked.

    So I might have started pre-puberty, sort of started at 20, and REALLY started at 48.

    Roberta
    [COLOR=Red]Open your Heart :

  18. #93
    Member Bonnie D's Avatar
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    I was about 11. Home alone one day and decided to put on my mother's evening/party clothes. Black panties, girdle and stockings, heels, black bra with rolled up socks inside, little black dress, necklace, clip-on earrings and some bright red lipstick. I've been hooked ever since. I think I wanted to be a girl before that though.

    Bonnie

  19. #94
    Junior Member Wendi0012's Avatar
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    when did I start dressing

    when I was 13 or 14 starting wearing my mom's dresses but it wasn't to long before they didn't fit any more. when I finish high school meet a young women who always left her cloths all the place one day she came home from work to find me in one of her work outfits

  20. #95
    naughty nurse Billie Jean's Avatar
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    When I was about 4 or 5 and my mother gave me and my sister her old stockings with runs in them to play with. Billie Jean

  21. #96
    MistyCD MistyCD's Avatar
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    Quote Originally Posted by Peggy55 View Post
    Age 50 for me. Just recently. Someone should start a poll!
    Maybe a better idea would be to start a new section where we could write stories about ourselves...

    Misty

  22. #97
    Junior Member janec's Avatar
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    about 9 or 10 in mums panties and tights

  23. #98
    Member Kelly Greene's Avatar
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    I started out with my sisters and mothers underware when I was around 5, but i did not understand what I was doing unitl I was 22.
    after trying to get rid of the desire to crossdress and failing I finally decdided to give my self premission to explore my feminine side and se where I end up.

  24. #99
    playing dress up JC's Avatar
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    age?/

    i was under 6 when i started. it was mom's stuff ....i do not remember what i wore .... it was fun being like mom.. when she saw me - jeeze was she angry. i then knew to keep the secret.

  25. #100
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    First experiences

    Does wearing my tights, leotard, ankle socks, and slippers to ballet classes count? I was about 6.

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