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Thread: What were you like as a teenage crossdresser?

  1. #51
    Aspiring Member Angela1954's Avatar
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    Feb 2015
    Upstate NY
    I did not start fully dressing until my late 40's early 50's. When I was growing up in the 60's and 70's fully dressing was a perilous path to take. I always tried on my mothers tights and loved the feel. Too bad I did not start dressing earlier since I have a slight build and probably could have passed pretty easily.

  2. #52
    Join Date
    Mar 2018
    During my early teens I was quite nerdy, somewhat shy, and rather slim for my height. When dressing I went for the tomboy / androgynous look with a feminine flare because it was effortless for me. I had girlfriends toward the end of my teenage years; I didn't dress much then.
    I love film, fitness, and fashion. Those are the keys to unlock my heart.

  3. #53
    Gold Member Lana Mae's Avatar
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    May 2016
    North Carolina
    I am a late bloomer! Teen years were like most here! Shy, did not date, more fetish type dressing, mostly in only panties! Despite this, one classmate called me, "A ladies' man!" I was able to converse well with both and at all social levels! If I knew then what I know now! LOL Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  4. #54
    Lady in waiting Peggie Lee's Avatar
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    Oct 2013
    San Luis Obispo County, CA.
    When I was 12 almost 13 my girlfriend and I swapped scout uniforms, me as a girl scout and her as a boy scout and we went out selling cookies and greeting cards together door to door. Being born intersex at 12 I really filled out her uniform and got a lot of compliments.

  5. #55
    Junior Member Alexis00's Avatar
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    Jan 2019
    Near Boston, MA, USA
    I wasn't any more shy than others. Started dressing at 9 or 10 and didn't know why. Went through a few cycles of activity my teen years where I would obtain clothing, usually lingerie, but sometimes a bathing suit. The summer I was 15 I really got into it, experimented with various types of breasts (didn't have the money for forms) and sometimes dressed fully. Tried lipstick but not makeup. Started dating girls at 16 and didn't dress at all that I can remember until the summer I graduated HS.

  6. #56
    Junior Member Natalie_393's Avatar
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    May 2009
    Albany, NY
    I remember dressing up any chance I could get, of course I was "borrowing" my sister's clothing until she started to notice things were out of place....So I had to start resorting to buying my own with whatever money I had. the only down side was in the early 2000's online shopping wasn't as popular and wide spread back then, thank god Ebay was around. My other challenges in my pre-teen/teenage years was I lived with my parents and sister and my grandparents so needless to say privacy was hard to come by but I still always seem to find time to dress

  7. #57
    Member Leelou's Avatar
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    Feb 2009
    I agree that this is a very interesting thread. I love hearing others' experiences when they started crossdressing and their early years.

    I wasn't shy at all and had a lot of friends, boys and girls, growing up in a small rural school district. I was active in sports but not a big guy, just average height and lean. I didn't have any sisters growing up so I had very limited access to women's clothes. My mom was bigger than me so I didn't really fit into much of her stuff. The first experience I can remember in my pre-teen years was wearing my mom's pantyhose. I was totally hooked. I didn't own a pair of panties until I was about 14-15 when I was able to abscond with a pair of panties from a friend of a friend's house. I'm kind of ashamed to admit that, but I know I'm not the first or the last to do so. I was desperate to have a pair and I loved having them.

    My favorite story about crossdressing as a teen was that I got to crossdress at school a couple of times. It happened during what they called Spirit Week in Jr. High. They had "battle of the sexes" day, which was basically crossdressing day. I was friends with a few of the cheerleaders and they twisted my arm and got me to wear one of their cheerleader outfits. I was in heaven! Several of the other guys were game, and I wonder if I was the only crossdresser in the group. There are even pics of our special team of cheerleaders in the yearbook. I got to do this two years in a row--dressed all day as a girl! Good times.

    When I got out on my own, I came out to a live-in GF--this was in my early 20's. She ended up sharing this with one of her girlfriends and soon I was out to our whole group of friends and everything was OK. Mostly my guy friends just didn't say anything about it, and it was all good. Her girlfriend's loved me. This was the beginning of me being out of the closet. I went back into the closet for a period when I was married to a woman that would not accept a crossdresser. I never came out to her, she just pre-emptively told me so. I think she suspected because I was super enthusiastic about her wearing lingerie. So I just lived vicariously lived through her and kept my girl clothes in storage. We divorced and I've been on my own since and been able to dress as much as I please and it's been wonderful.

    Sorry for the long post, but I love these kind of threads and enjoy sharing a brief history of my experience.
    Last edited by Leelou; 01-25-2019 at 03:58 PM.

  8. #58
    Soccer Mom in Training MsEva's Avatar
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    Aug 2005
    Quote Originally Posted by Megan Nicole View Post
    Probably like many here I lead two lives as a pre-teen, and a teen. 100% boy on the outside, and 80% plus girl on the inside. Lots of guy friends, sports, outside activities, and fishing, cars & trucks, girlfriends, etc. Yet, when at home I would dress every chance, and just wished I had been born a girl. I was extremely envious of many of my female classmates in school. So many pretty dresses, shoes, makeup and such. I just wanted to be like them. Tough time for a kid in this situation. Inter struggles were tough, especially trying to figure this all out. Glad that’s over! Much more at peace these days. Still envious of pretty ladies tho! -Meg
    Same here. Pretty outgoing but the femme side of me has always been there as long as I can remember. No sisters to get clothing from. Had to make due. I found a trunk with some basques and merry widow corsolettes in my attic left by former owner, I took possession of then quickly and never looked back.

  9. #59
    Member leotard fan's Avatar
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    Jun 2009
    lisbon, portugal
    When i was a pre-teen, i get inlove by girls and leotards more than before, seeing the girls in gym classes and ballet classes. Until today i didn´t stop wear leotards, thights and more... I was very shy. At street and school i was a regular boy, but at home alone (and i spent lots of time home alone) i was always enfemme, and when my mom arrives i wear female lingerie... i never know if my mom know about my cd (i had female cloths inmy closet), if she know it, she never talk to me about it. Big hug to you all.

  10. #60
    Member rhonda's Avatar
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    Jan 2011
    terre haute , in
    Looks like we have the same similar traits and that's why we are here in the forum with lifetime membership

  11. #61
    New Member
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    Jan 2019
    rocky mountains
    I was not shy nor an extrovert, not a hypermasculine kid though, more intellectual, played soccer, worked on cars, into the mountains on the weekends. Not that girls did not do those things, sometimes we all did these things together. I had plenty of guy friends, friends that were girls, and quite often had a girlfriend. I was probably lucky to have a pretty good time in high school and college. Our parents left us all alone a lot and we got in our fair share of minor trouble and mischeif! Most of the time the people I hung out with were pretty good kids and took care of things on our own without anyone watching over us.

    For a cis gender male as myself, I think CDing, is just something that is part of us. Growing up before the internet, without any outside influence that I am aware, I just had a fascination with certain girl things at a very young age. Nobody showed me or told me to try on my mom's or sisters underwear. I just wanted to. When I saw women in magazines and catalogs, I liked the look, and wanted to have that look too, if just for a moment. Those sexy underthings had some sort of power over me, being intimate to femininity, and that was exciting. For years I thought I was the only one and had some stress about keeping it a secret.

  12. #62
    Banned Read only
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    Aug 2010
    Virginia Beach, Va.
    As a teenager bras, panties and slips hanging on the close line did get my attention. Did the close line get me started in CDing?

  13. #63
    Member SHINY-J's Avatar
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    Jan 2011
    I’ll probably never know fully why I crossdress and what caused it,... but if I had to guess, I think it’s probably because I truly loved women from a very early age.. I remember having first crushes as early as 6 years old... plus, I was a comic book nerd kid and grew up seeing these powerful, buxom, curvy, bombshell women with big hair, and gravity defying figures and bodies wearing shiny, sexy costumes and outfits that left little to the imagination...

    Those heroine’s costumes where so similar to the lingerie and clothing styles I saw in Victoria’s Secret and Fredrick’s of Hollywood catalogs of the 80s and 90s... I just began to associate the two together and began imagining what those sexy clothes felt like on a beautiful woman...

    But being a kid still living at home with no sisters, I just began to sneak panties whenever I could.. from friends houses from their sisters room... etc.. When I started dating girls in middle school and junior high, I would sometimes sneak girlfriends panties when I could and stash them away.... Feeling them in my hands quickly became wearing them... and then it quickly spread to wanting more than panties... bras, heels, etc... them certain situations came about... like when I volunteered with my senior class to help at clothing donation center and was able to sneak a few items without getting spotted... Another time, I took a job with a new sporting goods store that was opening and my first day was helping to get the building cleaned out and the prior business had been a ladies clothing store... needless say, I snuck as man6 boxes to the trunk of my car as I could until it was completely full... I also went back later that night and went dumpster diving! Lol
    Unfortunately, most of it was too small or just boring and dull, but I did manage to get several nice items!

    I had a secret duffle bag full of an eclectic collection of panties, a couple of bras that didn’t really fit.. a satin garter belt that didn’t match, but did fit... and a pair of green high heels that were too small and hurt like hell, but I wore them anyway..... none of it matched,.. most were too tight or too big... but it got me through those early years.

    Obviously, I kept it well- hidden from everyone else, but I found time to dress whenever I could.

    I do remember the very first night living on my own in my new apartment (and I’m going to REALLY date myself here)... was spent filling out the PAPER order form of a Fredericks of Hollywood catalog ordering a black spiderweb teddy, size 14 red thigh high boots, and 3 pairs of size XL panties that would actually fit! I theN Mailed it in with my credit card info written on the form.. lol... it was 1999.. the Internet was around, but nowhere near what it is today!

  14. #64
    Lover of Silk and Satin Veronica Lacey's Avatar
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    Aug 2008
    Hi Katie...

    Yes, I found my way to endearing myself to female attire as a proxy or substitute for a girlfriend as well. I had come to a limited teenage experience-laden conclusion that I'd be solo for life so I delved more into dressing to make up for the absence of a partner. Even after finding my way into the dating scene and eventual marriage I believe that I had taken to the notion that dressing meant something to me perhaps for connecting to the feminine side within me. Yes, I was a shy kid/teen/young adult even with my sports abilities that attracted friends both male and female.

    Feel welcome to pm if you would like to share thoughts on it.


  15. #65
    A Woman Inside KarenSusan's Avatar
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    Aug 2006
    Mountain View, Ca
    I started dressing at about 9 or 10 and continued every chance I got through high school. I was (still am) painfully shy and never had or dated a girl. Like others, I used to wish I was a girl. I used to be envious of guys who could pal around with girls just as friends (no romance). For some reason I stopped crossdressing in college and then in my 40s it hit me like a brick and now except for having to leave the house I spend all my time living as a woman. For years I thought I was the only person afflicted with this. Thank God for the internet.

    Karen Sue

  16. #66
    Junior Member LucyDarlene2018's Avatar
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    Dec 2018
    Since it was the '60s, I was driven to do it and guilt-ridden when I did, and had to hide it. Stayed home when the family took out-of-state vacations. Even had to commit my first lie on a Federal form. Joined Sea Cadets in high school and we filled out standard enlistment forms (which were not used, of course). One question asked "Are you [this, that, the other], a transvestite," etc. That was awkward. Checked "No," of course.

    It took years to accept that this is a normal part of me and to discover that it is common. Eventually I got to where I accepted that one day I would be discovered and "Heck, meet the other me." Which is exactly what happened when neighbors dropped by unannounced last week. And they're OK with it. Still worried about the people immediately next door, though.

  17. #67
    Silver Member Crissy 107's Avatar
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    Aug 2018
    Virginia USA
    What a great thread, and to think we thought we were the only ones. I agree with Karen Sue, thank god for the internet.

  18. #68
    Junior Member
    Join Date
    Feb 2013
    I was a typical boy growing up doing all the rough and tumble things, but I was rather small in size compared to others so with inadequate talent and size I was always a bench warmer in school sports.

    My mother did sewing and alterations and I was drafted to be her dress dummy which after first hating I came to love. But after showing a little too much interest in wearing the clothes and heels I was replaced by a dress form my mother picked up in a resale shop.

    Shortly after that an older female cousin found out about my hobby and offered to help me dress. With her amazing makeup skills and a long, real hair wig she had snagged from a friend I was easily passable. We would spend many a Saturday going out shopping as two teen girls. I really loved wearing the Marcia Brady style mini dresses, bra, shaper brief, pantyhose and wedge heels. It was such a rush shopping for clothes and trying them on in the changing rooms

    Unfortunately once puberty fully set in I changed drastically and couldn't pass in a dark room full of people wearing sunglasses. It's been almost 50 years since I've worn makeup and fully dressed.

  19. #69
    Aspiring Member dana digs sweaters's Avatar
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    Feb 2010
    "What were you like as a teenage crossdresser?"

    Well dressed with 3 older sisters and a mother of course!
    Plenty of opportunities to dabble in the softer side of fashion.
    Rode a dirt bike, played football and hockey.
    Just normal childhood activities for the area that I grew up in.
    Obviously, conversations of wearing female clothes (beyond Halloween and high school Powder Puff games)
    was Not discussed with anyone except for my one sister who caught me.
    Shy? Nope, adventurous with the neighborhood school age chicas.

  20. #70
    Junior Member Chancey289's Avatar
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    Aug 2015
    It wasn't until a few years ago that I actually became serious about my crossdressing (because it took a while to come to terms with it), but as a teenager I did find myself secretly when I could trying on a girl's shirt or some lipstick.

  21. #71
    Join Date
    Feb 2014
    somewhere in a truck
    I was painfully shy and as soon as I could sell papers, TV guides, seed, greeting cards, go to work for my step father. Trying to make money to prove I was a boy/ man as according to my brothers queers were abominations in the Bible. Heck I was 5, I didn't know what either one was. My sister would dress me up and we would play sisters. But her and Mom always told me not to ever let my brothers know we did that. After my sister passed away, I dressed in her clothes every chance I got. My brothers were both gone from home by then and YUp, mom caught me multiple times. She said I shouldn't dress like that but she never took the clothes. Many years later she told me she had always wanted another daughter. It took me being married 3 times for my current wife to get me passed my shyness. She created a monster, that can now talk to anyone.

  22. #72
    Diva Keira Bea's Avatar
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    Feb 2019
    Kettering, UK
    I only briefly secretly dabbled in crossdressing on the odd moment back then in my childhood, due to living with my mum and siblings. I was a very shy and socially awkward insecure teenager, often bullied even by my brother due to physical handicaps. This emasculation started early for me since I was a child, such as from school. I never did quite fit in as one of the boys due to the handicaps, and it just went from there right through my adulthood. This is me now taking back some form of control by now learning to own the emasculation without shame as I slowly come out to more family and friends.
    I’m on a spiritual journey.

  23. #73
    Junior Member
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    Mar 2019
    I was so shy and self concious. Wearing my mothers dresses jewelry and lipstick felt so relaxing. My parents spent a lot of time away in the summer, so I had freedom to explore this. It felt confusing at first, I dont know why I wanted to dress up but it felt so good. It made me feel safe and comfortable with myself

  24. #74
    Member Jessica S's Avatar
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    Dec 2005
    South East Michigan
    Not shy at all as a teenager. Very athletic, was popular. No sisters , just brothers. Started wearing a panties and pantyhose at around 5 or 6 yrs. old. Went on to other clothes as I got older. Keep it hidden. Had the house to myself a lot and would barrow moms clothes that I could fit into.

  25. #75
    Junior Member
    Join Date
    Jan 2019
    Yup! I started with Mom's pantyhose at early age. Then more. And more. And more! Youngest of all male house, and no "direction", but knew something was "off" from my siblings...
    Sports and all male influence still did not steer me away from the Sear's catalogs pages of underwear, girdles and lounge-wear. Even at a very young age, there was "something" there that grabbed my attention more-so than the sports pages??? Let that be something a "therapist" can label me as...

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