Teenage Crossdressing memories

[SamanthaPanty]

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 )

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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!

[Beverley Sims]

I used to go to the Drive-In theatres with a carload of girls and we flirted with the boys in an adjoining car.

[Lygophilia]

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.

[phili]

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.

[karynspanties]

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.

[Karmen]

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

[Dawn P]

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

[Pixie_94]

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.

[nancymo4242]

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!

[Vicky_Scot]

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.

[Anna Gracie]

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.

[Barbara Black]

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.

[marlacd]

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.

[valerie anne]

I have an early memory about wearing mum's clothes.

I was about eight and keen to wear a bra. I got one from her bra drawer and put it on. I stuffed it with socks and waltzed round in my boobs and her lipstick. But the window cleaner suddenly arrived and in panic I pulled it off, detaching one of the straps.

I re-sew the strap in a very amatuer manner, leaving marks on the bra from my dirty fingers.

Nothing was ever said....

[Alice Torn]

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

[BrendaPDX]

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

[Maria_mtf]

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.

[Patience]

I remember being found out, being shamed very badly, and repressing myself for three decades.

[HollyGreene]

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.

[beckypanties]

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

[dana digs sweaters]

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

[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. 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?”

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Dana, you look AMAZING!

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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."

[dana digs sweaters]

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!

[Crissy 107]

Holly, My gosh you were very lucky!
Dana, I love the cartoon, so absolutely true!
Crissy

[prettytoes]

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!