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Thread: Where did you first crossdress ?

  1. #26
    Amanda LeAnn pantyhosecd's Avatar
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    In my Mothers bedroom with a pair of her RHT stockings, been hooked from then on.
    The Tip of The Toes To The Top Of Hose

  2. #27
    Member Lara Smith's Avatar
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    So young I can't pinpoint. Maybe preschool.

  3. #28
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    It was sometime in Jr High. I was going through the storage closet in my parents basement, ironically looking for old clothes I could use for a Hercules costume, and came across a box of some of my sisters old clothes. Inside I found a lycra leotard from when she was in gymnastics. The material felt smooth and stretchy. Completely new to me as I had only been used to boy things up until then. Curiosity got the best of me and so I tried it on. Wow...it was so tight and felt incredible how it stretched and covered me. I ran my hands over my stomach, chest, arms, butt, and felt myself getting hard despite being tucked away. I had never felt anything like that before and consequently led to my new hobby, which shortly after led to having the dream of being a real girl.

    There may have been some earlier experiences with girl clothes before this, but this was the moment when I realized that a) girls have more fun than boys and b) I wanted to explore more.

    Heh...feels good to share this.

  4. #29
    New Member JENNYgirl's Avatar
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    first time

    For it was in attic sisters dress me in black tights plaid skirt and blouse

  5. #30
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    I was 7...I think when i first slipped into my sisters yellow panties..then i wore her leotard and put her fur ear muffs between my legs...I was hooked...what can i say...

  6. #31
    TJ Tresa TJ Tresa's Avatar
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    In my mother's bedroom, the bathroom, and all other rooms in the house at the time. My mother had dressed me up in some of her old clothes for Halloween. I was hooked, little did she know I had always wished that I was a girl at that time.

  7. #32
    Claire Claire Cook's Avatar
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    I think I was 4 or 5. My mom let my play "dress-up" and put a dress on. me After that, I would try on her bras and girldes whenever I could in her bedroom.

  8. #33
    Member daphne g's Avatar
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    why the ear muffs between the legs?
    not tried that b4
    do tell, pleeese

  9. #34
    Aspiring Member
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    I found a pretty dress in the basement that was a hand-me-down and still too big for my sister. I was four years old. I took the dress to the area under our front porch that was enclosed with lattice. I could sit under there wearing the dress and no one else in our large family could see me. Leanne

  10. #35
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    There was an attic in our house. I borrowed one of moms slips and tried it on up there. This went on for awhile and then I got caught. She didn't say much. Just told me told to change and left the attic.

  11. #36
    Silver Member Jilmac's Avatar
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    For me, it was in an attic room. A cousin of mine had found a box full of girls clothes being stored in the attic and dared me to wear one of the dresses and a pair of panties. I was seven years old and the clothes were age appropriate so the dress and panties fit very well. I loved the soft silky feel of the panties and the prettiness of the dress. Having three older sisters I had an abundant supply of clothes to experiment with in their bedroom but that attic room will always be in my memory as the place where I started my favorite hobby.
    Luv and Jill


    Straight, into Fantasy Land

  12. #37
    Aspiring Member
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    For me it was nylons, in the bathroom at about age 14. In a family of 7, the bathroom was about the only place I could get away with it, except for the rare occasion I could find an excuse to stay home alone. Never got the chance to fully dress till my early 20's when I got my own place.

  13. #38
    70's Supermodel RiverdanceGirl's Avatar
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    My mums thick black tights on the floor of her bedroom . I don't remember choosing to put them on , I just had to . And then I put on my socks & pants , went downstairs and showed my mum that I had her tights on . She laughed , thought it was funny but let me keep them on the rest of the day and sleep in them . I was in heaven . She gave me a dressing up box with 60's style dresses , lots and lots of tights , bras , funky high heels , skirts and tops - the works . I would race home from school and dress before my dad got home - I wasn't to crossdress infront of him . On school holidays I could dress all day and did , even sneaking out in dress tights and heels to ride my bike on the back lawn . Funny , the neighbours never said anything even though they were not nice people at all . And then we moved house and mum said the dress up box had to go . So then I made a superhero costume with a black garbage bag as a cape and balaclava for a mask . Sheer suntan tights with red socks over for boots running around outside for everyone to see . Nothing was ever said . Well , except that Jane Whitley claimed I was the only boy in her ballet class - but I wasn't .

  14. #39
    Aspiring Member Jenniferpl's Avatar
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    My sister left her bra in the bathroom, so I tried it on and never looked back.

  15. #40
    In the closet in MD terry29's Avatar
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    my mom's bedroom,... I think it was a red matching bra and panty set. I've been hooked ever since Oh-yeah!

  16. #41
    New Member GirlyGirl26's Avatar
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    My very first time was in my bathroom. I was getting ready to take a shower and my sister left her baithing suit there. I tryed it on and was hooked.

  17. #42
    New Member woodstockloner's Avatar
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    my cousins bedroom while she and my aunt were at work... it was just a thong and a pair of pants but it was so freeing

  18. #43
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    first time being seen dressed was with a girl

    I was in the first grade.I had just moved into a foster home"one of many" any way I was playing with the girl who lived there about the same age as me I guess,she pretended plastic toy bowling pins stuffed in her shirt were boobies.and asked if Iwould like some ,I clearly recall her opening her dresser and handing me some yellow flowery panties and a girls nite gown,I changed in front of her and we both pretended the plastic bowling pins were ..well grown up girls is what we played in her room for a long time.I had tried on girls things before as well as sneaking off with moms things.I had enough brians as to know I should not be seen doing this.I never knew then that A boy wearing a girls clothes was socialy "awkward". I never stoped .the ones I liked nobody had.so in my early years no dought a few things became missing from ladies clothes lines in the middle of the nite.

  19. #44
    Member Paula TV's Avatar
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    When i was 18 home alone with alot of time to kill just putting on lipstick and make-up. It wasn't something i thought about before that, was just curious but i liked what i saw. It was a struggle for me as you could not imagine as it felt against my beliefs, as i had some very conservative beliefs at that time. But now i have learned to accept it. I hadn't really matured by then. I did as a kid put on heels to feel what it was like, but it was just a novelty and there was no real enjoyment of it at that time, so that doesn't count for me.

  20. #45
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    Quote Originally Posted by Christina2008 View Post
    Like others the first time I wore feminine items was in the bathroom, the lock on the door was the safety net. The first time I put more than one item on was in my childhood bedroom, as I started to build my collection.
    This is exactly as my "first times" were.

    It was when I was about 9 years old when I first started to try on/wear my older sister's and mother's panties, bras and slips.

  21. #46
    Miniskirts are electric JennaByNight's Avatar
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    I actually started "exploring things" when I was about three or four, but the first time I actually wore anything was when I was 16 and saw a black lace Teddy at JC Penny's. I bought it and wore it that night. And many nights thereafter. I remember that I felt absolutely electrified as I put it on. My heart pounded, my face flushed.... I also was NEVER late to get up in the mornings - because I always woke up really early so no one would catch me wearing it!

  22. #47
    We all have our dreams... AmiFL's Avatar
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    First time

    It was in mom's bedroom while they were out at work. She had alot of clothes that did not fit her anymore so she did not notice them moved about. My favorite outfits were a satin one piece swimsuit with a skirt and a pair of black skintight stirrup pants with a satin top. It was heaven. Then I began to dabble with makeup in our downstairs bathroom because for some reason I never felt dressed unless I was all made up and dressed..... it added to the thrill.

  23. #48
    Just finding my way.... StaceyJane's Avatar
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    I the bathroom. I would look through the clothes hamper for my mom's clothes to try on. Later I would try on my mom's dresses while my parents were away.
    Stacey

    I'm not a doctor, I just play one on TV.

    http://www.youtube.com/watch?v=Wob7zmvVTb8

  24. #49
    Aspiring Member StarrOfDelite's Avatar
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    i was a victim of sexual abuse by my cousin

    and found out that i liked it. when i was about 7-8 my cousin (Female) and her girlfriend, who were 3+ years older than i, used to strip me down and dress me up in her panties and dresses and mary jane black patent leathers. i got such a raging pre- adolescent erection from that. wow! it still makes me aroused to remember that. they used to giggle so evilly.

    i always lusted for my cousin, to no avail, but when she got married the girlfriend and i got drunk together, started talking about the old days. it developed that she got also got turned on when she was abusing me, and one thing led to another and we wound up in a motel room for most of that weekend.

  25. #50
    Just a part time woman? Tina Francis's Avatar
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    With twelve in my parents bedroom. I took some skirts and dresses from my mom and their shoes. Not high heels, but much higher than my children shoes and to big.

    Later during my studies I bought my first own female cloth and they fit well, I felt like heaven since that date.
    Tina

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