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Thread: Teenage Crossdressing memories

  1. #26
    Oh to be an English Rose Jane G's Avatar
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    Fun reading his thread. Not all fun as a teen of course. I was convinced I was a girl in a boys body, at that age. There are so many happy memories. Walking for miles in the evenings after every one else was tucked up in bed. Diving over fences to hide as Police cars approach and past. It was a huge adventure and fun in so many ways. BUT mostly it was purgatory. My farther would come home from his club after a few drinks and well it was not all roses, he did not approve, rest his sole. The navy was the escape route from teenage life as a cd for me.

  2. #27
    Member michelleg's Avatar
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    I was fortunate that we had a huge backyard in a very rural area, so no neighbors. I spent many afternoons of my teens in various stages of dress and loved every moment of it. The freedom of being outdoors, the excitement of wearing things that felt so good. I was never in a situation to acquire my own things until much later, so I wore my Mom's dresses, lingerie and gowns and makeup. Most likely the time in my life where I became a crossdresser. Those are great memories, thanks for starting this thread.

  3. #28
    Aspiring Member Robbiegirl's Avatar
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    Great Thread ! Grew up between 2 sisters, had a lot of fun with thier cute Tennis dresses and frilly tennis panties. LOL

  4. #29
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  5. #30
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    I kind of envy you older gals. You had such nice clothes back then to experiment with. By the time I was a teenager, the ladylike 1980s were over and grunge was in. Was lucky to see a girl my age wearing pantyhose when I was in high school, much less gartered stockings, full slips, girdles, silky blouses, pretty shoes etc.

  6. #31
    Struggler with CDing Pixie_94's Avatar
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    To me any of this is related to guilt-trip-like memories or things that are embarassing to remember, things I would have like not to do at all since it caused me trouble.
    Last edited by Pixie_94; 11-24-2018 at 09:26 PM.

  7. #32
    Sallee Sallee's Avatar
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    Grew up in the 50's and 60's with no sisters so i use to use my mothers cloths a lot. I eventually got caught and it was off to see a psychologist. So they could figure out my problem. I wouldn't talk So after afew sessions the psychologist got canceled. I became a lot more cautious about my dressing IT wasn't until the mid 70's and I got my own place that I really began cross dressing a lot. I was in a city where no one knew me. I found a support group and a few gay bars that had drag shows so I was off on my cding career What along strange trip it has been
    [SIGPIC][/SIGPIC]Sallee

  8. #33
    Multi-Blogger Barbara Black's Avatar
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    I once entertained the idea of using a bicycle to rob clotheslines also. Never did though.
    I grew up with three sisters, but was too fearful of getting caught and never wore anything other than underwear left lying around. Such an opportunity wasted.
    Last edited by Barbara Black; 11-25-2018 at 12:25 AM.

  9. #34
    Member marlacd's Avatar
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    I started about that time. I changed schools, and wasn't accepted. Living in a semi rural area, there wasn't anyone my age nearby. Toss into the mix was my mother, who was working at the time, and she was very strict about where I went. I was painfully shy, and most of the girls were pretty mean to me. I was very interested in them, but prior experiences kept me away from them. Somehow, I got it in my head that if I dressed like one, I'd feel what they did. It didn't, but their clothing did feel very nice to wear. Between my older sister and my mom, I had a pretty wide selection to choose from. It felt great to get dressed up, but what killed the looks was what I saw in the mirror- an unfinished woman. Then my mother came home with a WIG! Oh happy days! I could dress up, add the wig, and I looked finished! I then started living for the days that got me alone, where I could dress to the nines for a while. On those days, I went the whole way-even using makeup, nail polish, even perfume a couple times. I did that all through high school.

    The summer after I turned 18, I decided to grow a mustache, and get away from dressing. The thoughts of dressing still stayed with me, however, even though I wasn't doing it. But my luck with the ladies didn't change.
    I don't dress up because I want to be a woman, I dress up to make me happy.

  10. #35
    Senior Member BrendaPDX's Avatar
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    As far back as I can remember I wanted to crossdress, I remember trying on the skirt from under the Christmas tree, that was all it took, I was hooked. I remember my first dress from the Goodwill store, it was a side zipper and it fit like a dream

  11. #36
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    My first time was around 5 with my mother’s clothes and yes I was caught. So then I didn’t get too experience the joys of women’s clothing till I was around 13 with my step sister panties

  12. #37
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    I had a great time. One time, during a hot summer evening of my (very) early teen life, when my parents were away, I did something really bold. I wore a complete feminine outfit while bike riding around in my neighbourhood. I had on a cap, bra, panties, denim short shorts, a thin t-shirt, and a flannel button up shirt tied about my waist. On my feet were sneakers. I walked into a convenience store and I purchased candy or a magazine; I forgot which exactly. But I do recall my heart was thundering the whole time!!

  13. #38
    Member DanielleCD's Avatar
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    I think the majority of us started when we were teenagers... I was 14-ish.. mom's pantyhose and then my sisters underwear.. panties and bras. Loved it... even my sisters friends... stayed for a sleep over... I "borrowed" her clothes in the middle of the night. Back then with raging hormones, I got a sexual kick out of it. That has changed over the years but still, and always will, adore bras and panties.

  14. #39
    Senior Member Christie ann's Avatar
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    Mom was both a figure skater and a square dancer. Afternoons, after school were spent picking between skating dresses and square dance dresses. Of course I had only a half hour before some one came home, but it was a productive 30 minutes.

  15. #40
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    I was incredibly lucky to have a high school girlfriend who both understood and supported my feminine side. I would probably still be a full-time crossdresser today if not for her, but there’s no question that her influence was huge. Not only did she teach me to do my makeup, set my hair in rollers and put on a pair of pantyhose, she was also the first person to tell me “It makes you happy and you’re not hurting anyone. You should do what makes you happy.”
    A few details, in case you’re interested: This was in the ‘80s, in the Mid-South. Laurie was on the drillteam (they call it poms today -- they marched / danced with pompoms at halftime in cheer outfits or leotards), and she was a total Southern girl: never left the house without her makeup and her hair perfect. She was also incredibly kind-hearted and generous and accepting. We got together in 10th grade and by that summer she knew I loved dressing girly. I had grown my hair out and she got me to cut it in a more feminine, shoulder-length style and she started doing it in hot rollers, up in high ponytails (sometimes with a bow), braided pigtails, etc. This was the era of white Keds and Dr Scholls sandals and in summer that’s basically all we wore. (I will never forget the 2 of us going to the department store to buy my first pair of Keds.) She bought me my first pair of girls’ high-waisted jeans plus a couple of girly tops (one in particular I remember was a white pullover, nearly see-through). And she got me to wear makeup & nail polish regularly when we went out ( I drew the line at going to school made up).
    She and a couple of other girls on the drillteam tried to get me to try out, knowing I would have to wear the girls’ outfit. I ultimately chickened out, not before going to the pre-tryout “clinic” where I learned the routines with about 30 other girls. I became sort of an honorary member of the squad, going to their car washes and poster parties, wearing a cheer t-shirt with my hair up in a white bow, etc. We dressed and did our hair alike a lot and more than once got asked if we were brother and sister. On Saturdays she and her mother would put their hair in rollers for the day and after a while they started doing mine as well. We would mostly hang out by the pool at her house, but a few times we went out together to the mall, to McD’s, etc. with our hair in rollers, wearing our cheer t-shirts with gym shorts and Keds and white socks. It was heavenly.
    Amazingly I didn’t get that much ridicule even when I showed up at parties obviously dressed like a girl. (I didn’t wear skirts in public at that time.) I think partly it was because I was also a good athlete (basketball and track), partly because Laurie and her cheer/drillteam friends were the “cool girls” and they were totally supportive of my girly style.
    I went up East to college, cut my hair and really didn’t start crossdressing again until my late 20s. But I always had that high school experience to thrill and inspire me. Such fond memories. Laurie and I stayed in touch sporadically and she never failed to ask me “So are you still rolling your hair?”

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

    Dana, you look AMAZING!

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

    P.S. My wife likes to say that my fashion sense is still stuck in the 1980s, and she's not totally wrong. One of her, and my, favorite comments: "You dress like an off-duty cheerleader."
    Last edited by TracyT; 11-27-2018 at 11:51 AM.

  16. #41
    Junior Member Annemarie Dutch's Avatar
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    What a great thread this is!
    I remember just a few occasions of my early years.
    I must have been around 5/6 years old when I asked my mom to put me in make-up. I went outside with it, she asked if I was sure to do that. But I was very sure and did it right away!
    I still envy the boldness of kids...

    Growing up I remember my mums lingerie, and my sisters clothes in the attic. As long as it was tight! And that is still my favorite.

    It all faded away during my teens, came back in my early twenties but my wife didn’t like it. The last two years I am back at it again, and went to a therapist to find out who I really am.

  17. #42
    Aspiring Member dana digs sweaters's Avatar
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    TracyT

    "I was incredibly lucky to have a high school girlfriend who both understood and supported my feminine side.
    I would probably still be a full-time crossdresser today if not for her, but there’s no question that her influence was huge.
    A few details, in case you’re interested: This was in the ‘80s, But I always had that high school experience to thrill and inspire me. Such fond memories."

    Great story! Thanks for sharing.

    "Dana, you look AMAZING!"

    Not me, pic was for reference.

    This is me

    Face.jpg

    "P.S. My wife likes to say that my fashion sense is still stuck in the 1980s, and she's not totally wrong. One of her, and my, favorite comments: "You dress like an off-duty cheerleader."

    LOVE this!

  18. #43
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    Still beautiful....

  19. #44
    Member marlacd's Avatar
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    Better question- Who could strip faster than superman when someone came home? ( Be honest, aren't you snickering right now?)
    I don't dress up because I want to be a woman, I dress up to make me happy.

  20. #45
    Aspiring Member dana digs sweaters's Avatar
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    Quote Originally Posted by marlacd View Post
    Better question- Who could strip faster than superman when someone came home? ( Be honest, aren't you snickering right now?)
    Haha!
    You're not kidding Marla

    son we re home.jpg

  21. #46
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    my mom always wanted a girl so basically i was raised as a girl... but some of my relatives disagree tho but who cares :P

  22. #47
    armchair philosopher ElianaFrozenflame's Avatar
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    I was hooked on women's clothing at age 4.

    I was caught in my bedroom wearing one of my mother's dresses at age 4.

    Caught by my father in bed wearing a pair of my mother's pantyhose at age 7.

    Up until I hit my preteens, it was "that's cute son, give your mother her clothes back".

    I had a serious father/son talk at age 12, when I had commandeered a complete outfit out of my mothers clothing, and hid them in my closet. Bra, panties, hose, dress, and heels. I was sorry that I had been caught. I was embarrassed, and felt guilty. But I guess, not enough to stop.

    I later managed to keep 1 or 2 pairs of my mother's pantyhose tucked in my dresser, so that I could wear them at night. I had even went out in public wearing a pair under my pants, to do my paper route, a couple of times.

    I was not particularly defiant to my parents except for this.

    Daisy duke from Dukes of Hazard was my childhood crush. But I didn't just want her as a friend, I wanted to wear what she wore.

    My parents never talked to me again about my crossdressing after the father/son talk at age 12. But I suspect it was because they just chose to look the other way, rather than that I had become more successful in concealing it.

    I stopped dressing, cold turkey, when I left for the Army (age 18). I remember coming back on leave from Germany. The first night home, I found some of my mother's dresses in the basement closet. I put one on, and had locked the door, and went to sleep. By morning, I discovered that either my father or mother had managed to get the door unlocked, and there I was, only partially concealed under the blankets. I had wondered if they had walked in on me in my sleep. I never asked. They never said anything to me.

  23. #48
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    when I was in my early teens my mom's shoe fit me for about a year, my sister got her first training bra and started wearing pantyhose. I was in heaven, I was "sick" at least one a months just to have dressing time. I never really hid anything I always try to put everything back just the way I found it.
    I also remember laying in bed thinking I would love to raid my cousin's closet and thinking that this "dressing up" thing is just a phase and will soon fade. Forty years later its going stronger than ever.
    Sara

  24. #49
    New Member MAGurl's Avatar
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    It is amazing how common many of our experiences were. I had sort of forgotten dressing up in my mom's clothes when my parents were out for the evening. I think it started with exploring here panty drawer, then trying them on, then going further one night and putting on a bra, dress and jewelry and posing in front of the mirror, I might have even tried lip stick. I put everything back the way I found it but when they got home I remember the terror of my mom saying "where you in our room"? . . . "um no" I said and that was the end of it. Funny how clearly I remember that, I don't think I ever did that again, there were also very few times when I was home alone without a babysitter so I expect the opportunities did not present themselves. I also plead guilty to exploring the neighbors houses when I was feeding pets etc. and sneaking a look at panties stuffed in luggage as a teenager on trips with my cousins. I don't recall feeling any shame about any of these activities, it was just fun.

  25. #50
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    I dressed often as a teen. In my early teens I wore my sister's clothes around the house whenever possible. After I got my license, I one day stumbled across an adult book store in the city center and that was the beginning of a whole new, sordid chapter in my life.

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