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Thread: Teenage Crossdressing memories

  1. #1
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    Teenage Crossdressing memories

    Hi All, I am wondering if anyone was crossdressing in their teens?

    I know I was and I am happy to share my memories about the lengths i used to go to get some girly cloths to wear when I was alone as it was not easy and I sometime (mostly) stole some cloths... I know it was wrong at the time but I had to know what it felt like to dress in different styles of panties... what tights felt like... what walking around is a short skirt, going swimming in a swimsuit was like and putting my first mickey mouse thong on that changed me for ever.

    Does anyone have a story or two to share?

    Sammy )

    [SIZE=1]- - - Updated - - -[/SIZE]

    So the first time I put a thong on...

    When i was about 14 years old my brother took me to a beach party where one of the older girls at the party decided to go for a swim and so she stripped down into her bra and panties. The panties where a red Micky Mouse Thong I was mesmerised and transfixed not on her but how the panties fitted perfectly and wondered how they must feel ( i have warn panties many times by this time but never a thong ) I was for a better tear enviouse of this girl for being able to openly wear such a beautiful feminine garment.

    Some weeks had gone by and I visited the local Gym where all the girls had a thing of wearing panties over their tights (it was the 90's and South Africa) I had a huge crush on this girl and she was wearing over her tights the same cute thong panties over her tights... I was fix sated at them and again envious of her being able to wear such things...

    Well one night i was on my way home from a friends place and saw some cloths hanging on a cloths line... well needless to say I went to take a look at on the line was a red Micky Mouse thong... well I took them home.

    I remember just looking at them wondering how such a small piece of material could cover a girl and i remember sliding them up my legs for the first time the, and the feeling it gave me was amazing...

    I have been wearing thongs ever since and been buying them when ever I can as i feel they are the most feminine girls clothing. They way it always reminds you that you are in panties as its up your but is amazing feeling for me.

    Just amazing!

  2. #2
    Platinum Member Beverley Sims's Avatar
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    I used to go to the Drive-In theatres with a carload of girls and we flirted with the boys in an adjoining car.
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  3. #3
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    Glad those days are over. I've got tired of hiding them from my family members at that age. The only excuse was my mom letting me wear some of her clothes, because it was tough times of financial issues for her to get me bigger clothes. I mostly prefer of what to appear to be unisex clothes.

  4. #4
    Senior Member phili's Avatar
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    When I was 13 I would raid the lost and found at our swim club, and then take my prizes out to the woods and walk around, or go out on deserted streets at night, trying desperately to feel what the mystery was of the 'feminine mystique'! . I mistakenly thought girls were pleasured by their clothes the same way I was. I would go swimming in the lake in their suits - taking advantage of the fact that only my head showed to others!

    When I was 15 my 16 yr old girlfriend discovered I was wearing nylon panties, in our first sexual experience. She was startled, then said- "hmm couldn't you find something more masculine?" but from then on it wasn't an issue, so that was nice. She was older and more experienced, but I was disappointed that she didn't want me dressing in her dresses.

    I am grateful for the space I did have to feel feminine in my own way, and so wished I wouldn't have had to hide.

    My most special teen experience- maybe age 17, was going to a meetup room on the college campus where I could crossdress, and where there was a makeout room. I soon hooked up with a 50+ yr old former UK marine, who was kindly and delighted in the fun of interacting with me aroused in my bikini panties and white peasant blouse. He was happy to pleasure me, and did not demand anything for himself. ...it was wonderful! It became complicated as he started reminiscing about how he had last interacted with young men like me by choking them into unconsciousness. He was glad, I think, that now he was letting me be so vulnerable and free to not hurt me. I soon found a way to leave. It helped me realize that people are complicated, that combat training can really destabilize people, and not to put myself in that situation again.
    Last edited by phili; 11-22-2018 at 10:26 AM.
    We are all beautiful...!

  5. #5
    Aspiring Member karynspanties's Avatar
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    I started getting into my moms slips when I was maybe 3. She would put me down for a nap and I would sneak into her room and open the bottom drawer of her dresser where the slips were kept. I would climb into the drawer and wrap the slips around me like a blanket and fall asleep. She would find me and put me in my own bed. When I got older, I would get into my sisters slips, panties and bras. I would take then into my room ad hide them under my mattress. Not too smart or stealth. It was well known that I liked to wear girl clothes my entire childhood. Finally my mom stopped trying to get me to stop. One day when I was 13 she went out and bought herself some new panties, bras and slips. All of her old stuff was put into a bag and set on my bed, no note, nothing said, but I knew why they were there. Anything I wore I just threw into the dirty laundry basket and it was washed and put into my dresser drawer. Occasionally something new would appear. It was all unsaid.
    As I was in my early teen years the girl next door found out I liked to dress. We had a lot of fun with her dressing me in her underwear and clothes. We lost our virginity to each other. I have had a few experiences in those years with various people that found out about my choice of clothing. Some very good times and some no so good times.
    Last edited by karynspanties; 11-22-2018 at 11:04 AM.

  6. #6
    Aspiring Member Karmen's Avatar
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    In my teens I started wearing panties and pantyhose under my male clothes. Going out like that was an adventure for me at that time. When home alone, I always put on my mom's skirts and shoes, until I could fit in them. I had some near misses when parents returned home early and was nearly caught dressed like that. When I couldn't fit in them any more, I used my allowance to buy my first heels. They were similar to these in the picture, but dark red. I wore them for years.
    platform_heels.jpg
    Last edited by Karmen; 11-22-2018 at 01:58 PM.

  7. #7
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    My parents would go out to dinner every Friday night. That was my time to try on my mothers dresses and underwear.

  8. #8
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    I don't remember dressing up much when I was a teen.
    However, I do vaguely remember wearing my mom's panty hoses and panties.
    I also had some weird fetishes, like wearing tight panties and pants.
    The most clear memory I have of crossdressing as teen, was wearing my mom's panties while smoking a cigar.
    I did smoke quite a bit before she came out of the shower.
    I panicked!
    I quickly put out the cigar, and raced to take the panties off.
    I thought better she sees my dick than me wearing her underwear.
    But...
    It was too late...
    As I had them on the top part of my ankles, she passed by my room and the door was open.
    I did come in her line of sight.
    She must have seen me!
    Anyway...
    She never said a thing about it.
    Ever.
    I don't think she would have liked it, but she didn't hate me for it.
    So yeah, that was a bit of my teenage crossdressing years!

  9. #9
    Banned Read only Vicky_Scot's Avatar
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    Cycling around my local area stealing bras, panties, suspenders, stockings, tights etc from washing lines. Nearly got caught on several occasions but just could not help myself.

  10. #10
    Gold Member Alice Torn's Avatar
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    I started about age 13, experimenting with my sister, and mom's hose. Then, dresses, girdle, bra. Quit for a long time. Came back strongest at age 51

  11. #11
    Member Maria_mtf's Avatar
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    My mum would often go out at weekends, that was my time to try her things on. She had a wonderbra padded bra in a packet at the bottom of her closet. One time I was lazy and left it under my pillow, after returning from school I found it on my bed.

    When questioned I calmy made up a lie on the spot about it being a prank for my brother. I was never questioned about it again, but I guess my mum probably knows. Shes homaphobic and racist so generally closed minded so guess she just doesnt want to know.

  12. #12
    🙊🙈🙉 Patience's Avatar
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    I remember being found out, being shamed very badly, and repressing myself for three decades.
    When haters hate, I celebrate!

  13. #13
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    I used to play in some disused quarries when I was a kid. Being a bit of a loner, I often used to go down there alone. One day, when I was about 15, I found some large plastic sacks of women's clothes that somebody had thrown down there. They hadn't been there the day before, so I knew they hadn't been there long. What a find! There were numerous skirts, slips (waist slips and full length), a few tops, a pair of platform shoes that were about 1 size too big, and a wonderful one-piece swimsuit. Everything was clean and in reasonable, used condition.
    Needless to say, I plotted ways of getting these things home. It generally consisted of putting one or two things on under my clothes and getting them home that way.
    My dad had built me a den in the house roof space, so I had the perfect hideaway for everything, and a private place to try things on.
    These were the first items of female apparel that I owned, and I kept them for several years.

  14. #14
    Re Member beckypanties's Avatar
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    Holly, maybe your find was another CDs purge? I was never lucky enough to find wearable clothes like that, but did find plenty of woods porn

  15. #15
    Aspiring Member dana digs sweaters's Avatar
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    Oh so many memories as a teenage transvestite
    Always enjoyable to me
    Such fun growing up with practically unlimited access to female clothes
    The talk shows just started and to draw in viewers, they had a revolving door of men dressed as women
    I knew I was not alone and possibly what was in store for me as I grew older

    not like other boys.jpg

    and always trying to copy their looks

    boy.jpg

    pic for reference
    Last edited by dana digs sweaters; 11-23-2018 at 10:15 AM.

  16. #16
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    Quote Originally Posted by Vicky_Scot View Post
    Cycling around my local area stealing bras, panties, suspenders, stockings, tights etc from washing lines. Nearly got caught on several occasions but just could not help myself.
    Same here. Ride The bike at day, scouting. Then harwest The clothes line at midnight.

    That was a long time ago.

  17. #17
    Platinum Member Crissy 107's Avatar
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    Holly, My gosh you were very lucky!
    Dana, I love the cartoon, so absolutely true!
    Crissy

  18. #18
    Breathes under water prettytoes's Avatar
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    I can remember taking care of a neighbor's dogs when they were away...I had to check their daughter's closet (she was a year or two younger than I was)...found a mini skater skirt and just had to try it on...I loved dancing around the house in it. I put it back just the way it was. I was maybe 14-15...long time ago!
    Life's too short to not be enjoyed! Live each day to the fullest!

  19. #19
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    My teenage memories were a horror show. I'm a child of the 1950's and 1960's. Puritanical would be an appropriate description of anything sexual. Throw crossdressing into the mix and I was destined to burn in hell. A male wearing women's clothing equaled being a homosexual. A very confusing time. Lusting over good looking girls my age, and, women who were definitely unobtainable was very confusing if I was a homosexual and did not know it. Enlighten me! Anyway, the prospect of being called a "fag, queer, a fruit" and subject to discrimination and violence did not appeal to me. I suppose nobody would like to endure society's scorn.

    My parents probably knew I was wearing my mother's clothing. I was never asked. Maybe, they were trying to figure it out since I had an older brother. I do not think they had the balls to directly ask me or my brother. There was a little cat and mouse game going on. Once, I had donned one of my mother's sun dresses while my mother and father were out for a walk. Dad was recovering from a cancer operation. I thought I had it all timed out. I watched from our sixth floor apartment window. Yikes! I could not see them. OMG! They were at the apartment door trying to get in, but, I had set the security chain. Bang! Bang! Thank God for a strong chain and a steel door and door frame. I shed my mother's dress and stuffed it away in the closet. Then I opened the door and pretended that I had to been in the bathroom. They missed their opportunity to find me in a dress or her slip, girdle, etc. There were also times when I had to work during the summer when my dad had off mid-week. They tried to tell me to not work. I upheld my work ethic and said I had to work the schedule. Of course, the rest of the family took an overnight trip to my grandparents home upstate New York. I rummaged through mom's stuff. I'm sure she knew I was messing around with her stuff. How else would the strap on her one and only black bra break?

    I've said once or twice on this forum. Growing up as a young man liking to wear women's clothing was more stressful than being a combat infantryman in the Nam for the six months I survived there.

  20. #20
    Silver Member Pumped's Avatar
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    When I was in high school I worked at a gas station that had a repair shop. We had a big rag bin full of old clothing. I didn't think much about it until one day I pulled out a bra, then the "light" came on and I was hooked. I remember shoving that bra down to the bottom to make sure it was there later, I closed and would be the only one there in the evening. I remember going through that bin of rags and finding a couple pieces of naughty bits and bringing them home. Every couple weeks the boss would show up with a couple garbage bags of "rags" and I would spend the evening going through them. Pickings were pretty slim, huge bras that would fall off my 140 pound frame, old granny panties, skirts and dresses that were huge or way out of style, so bad a desperate teen aged cross dresser wouldn't even wear them, but once in a while I would find a good piece of clothing that I stored them in a locker in my closet. I had a pretty good collection by the time I graduated high school. I moved away to go to college and that was the end of it. I had no place to store my stuff so one day I tossed it all before i went away.

    Later on I remember managing some apartment buildings. I remember going in from time to time to do repairs with the tenant's permission. One day I was in the bedroom of this one young woman, she was gone. I was repairing a door and there was a clothes basket sitting there full of her freshly washed clothing waiting to be put away. I remember digging through it and finding some bras and panties. As much as I wanted to to I couldn't bring myself to grab something for myself, the thought of getting caught kept me under control but I did enjoy looking things over. I have quite the lingerie fetish and she wore some sexy bras and panties! That was all around 40 years ago and those feelings had been repressed for some time, until about 10 years ago and everything came roaring back again.

  21. #21
    Miss Judy Judy-Somthing's Avatar
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    You People are (SO BAD) "I love it". My sister dressed me up in her Ballerina outfit at & back in the mid 60s, I was hooked!
    I guess for a CDer I was lucky that in our attic there was a treasure trove of Girl's/woman's clothes. I was out of control.
    My fondest memories were for the girdles of the 50s and 60s, how could anybody wear one of those all day unless your were a CD'er I wore them to bed every night!
    Ya I know it's not right, LOL! Ya I know I'm a man, Give me a break, it's not my fault!
    And ya, pantyhose are so cool!
    Last edited by Judy-Somthing; 11-23-2018 at 08:16 PM.
    "This is ME" I am not CRAZY, I'm just a GUY who likes dresses!
    Since allot of men dress up in woman's clothing that makes it a manly thing to do!
    Much more fun than fishing.
    I do construction like house building and I love CD-ing, what's the difference?

  22. #22
    Ah-May-Lee
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    I spent most of my teen years avoiding bad men, didn't think of much else.

    I didn't do much of any dressing as a girl when I was a young teen. It was in my late teens that I came to discover that I was a girl, before that I just thought I was gay. By my late teens I could buy my own clothes. I didn't try on other people's clothes or steal any, well maybe I did shoplift from some stores, mostly make up.

    Anyways, as a teen I had an androgynous style to my clothes. I wore whatever I thought was cool.
    In solitude where we are least alone. Byron

  23. #23
    Senior Member Glenda58's Avatar
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    Mother was a girl scout leader. As the girls grew out of scouts they would give my mother their old uniforms and she would give them to girls that need them. Well we had skirts and blouses and some half slips in the house. When everyone was gone I would dress up and sit on the front pouch at the house. This was in the 50s
    GLENDA
    I FEEL LIKE A WOMAN

  24. #24
    Re Member beckypanties's Avatar
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    I'm sure our moms must have known about us raiding their closets. Mine never said anything. I tried to put everything back the way I found it but I was never able to fold her lingerie as neatly as she could. She must have known that me or one of my brothers (or all of us?) were rummaging through her delicates. Looking back on it, I wonder whether my dad might have dabbled a little. There were a few items in my mom's closet (leotards and such) that were hard to explain.

  25. #25
    I accept myself as is Gillian Gigs's Avatar
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    Okay, I'm giving away my age, my favourite memories, one, my sisters crinoline, and two, her cheerleader uniform. I grew out of them too soon, boo hoo.
    I like myself, regardless of the packaging that I may come in! It's what is on the inside of the package that counts!

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