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 :o)

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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.
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[Dawn P]

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

[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.

[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

[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 :hypnotized:

[dana digs sweaters]

Oh so many memories as a teenage transvestite :)
Always enjoyable to me :o :o
Such fun growing up with practically unlimited access to female clothes :cheer:
The talk shows just started and to draw in viewers, they had a revolving door of men dressed as women :^5:
I knew I was not alone and possibly what was in store for me as I grew older :daydreaming:

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and always trying to copy their looks

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pic for reference

[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.

[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!

[Stephanie47]

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.

[Pumped]

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.

[Judy-Somthing]

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!

[Amelie]

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.

[Glenda58]

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

[beckypanties]

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.

[Gillian Gigs]

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.

[Jane G]

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.

[michelleg]

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.

[Robbiegirl]

Great Thread ! Grew up between 2 sisters, had a lot of fun with thier cute Tennis dresses and frilly tennis panties. LOL

[BLUE ORCHID]

I Samantha :hugs:, Welcome to our forum, When you are here you are HOME!

What ever questions that you have there is a 99.875% chance that one or more of us will have a answer for you

I have been in this program for 74years now with no signs of slowing down. >>>Orchid ..O:daydreaming:O..

[Vickie_CDTV]

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.

[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.

[Sallee]

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

[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.

[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:o

[Jen84oh]

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

[candice.aihara]

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!!

[DanielleCD]

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.

[Christie ann]

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.

[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."

[Annemarie Dutch]

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.

[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

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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."

LOVE this!

[TracyT]

Still beautiful....

[marlacd]

Better question- Who could strip faster than superman when someone came home? ( Be honest, aren't you snickering right now?)

[dana digs sweaters]

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

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[honey1036]

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

[ElianaFrozenflame]

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.

[sara66]

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

[MAGurl]

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.

[MonicaPVD]

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.

[SamanthaPanty]

I think tennis dresses are very sexy and cute!

[sometimes_miss]

I spent most afternoons after school at home wearing my sister's clothes, trying her make up, styling my hair like hers, using various hair accessories too. She always also had quite a few current girl magazines (Cosmo, Glamour, Madamoiselle, Vogue, etc), and I loved reading those, too. She was at college or working, both mom and dad worked until dinnertime, so I knew I was pretty safe. A few times my sister came home early and I had to scoot back to my own room to change back, but that was rare. We also had a dog, so even when sis did come home, the dog would come running to her and she would immediately take it for a walk, so I still had time to get out of her clothes. I pretty much never borrowed anything that she was in her current collection of clothes, and as far as I know she never had a clue. When I finally came out to her almost 30 years later, she acted horrified, and never said anything to give me the feeling that she knew I had ever been 'borrowing' her clothes back then. After she moved out, she left one particular minidress made out of some cool feeling polyester or nylon material called qiana; after I found it stuck in the attic stored away with a lot of other stuff she didn't want anymore (mom was a pack rat), I took it for my own. I loved wearing that dress, and kept it for years.

[Desiree2bababe]

The teens years were the best although also the most worrisome. I got caught regularly by my mother and eventually ended up in counseling, which did help me understand transvestism better. Must say ages 18 and 19 were the funnest though as I learned how passable I was and desired by men. Those nights on the dance floor were the best.

[Jennifer in CO]

Threads like this is why I wrote down how my childhood/teen years went. May post it someday somewhere. Suffice it to say while my Mom and I were DADT she was well past just supportive in late teen years

[Jason+]

Like many I discovered panties in my early teens. During this time one of my younger brothers helped my parents "find" my collection of panties. This led to a very red faced conversation from my side and my parents asking me to promise never to bring another pair home. They told me it was a road I didn't want to go down. With one short lived and guilty exception I kept my promise. They have since softened their stance and are happy to have me any way they can get me.

[Patti Remick]

I am the youngest of 3 with 2 older sisters that were 6 and 7 years older than me. Well into my early teens I had plenty of afterschool 'home alone' time (this would be anywhere from 3-6 hours depending on when I got home and when my sisters did as they were very involved in aftershool activities). And for a young CDr our home was a paradise! My mother was a total pack rat (probably from growing up dirt poor herself) and kept almost all of my sisters old clothes from when they were younger. So I was home alone in a house filled with tons of perfectly fitting girls clothes. My father even had built a huge walk-in closet in our basement for my mother and sisters to keep there clothes in! My sisters had so much stuff - dresses, skirts, blouses, jumpers, even their old shoes! I wore their panties, tights, vests and training bras, and pantyhose. I wore almost everything of theirs that I could and I was one of the best dressed little CDrs you could ever meet. And this was the 1960s and early 1970s and girls clothes were GIRLY. One of my sisters even had some wigs (she obviously was experimenting with her own looks) and they were just the icing on the cake for this little CDr. There were even ballet outfits and a skating dress (even though to my knowledge neither of my sisters skated). I dressed almost daily until about age 15 in perfectly fitting and age correct little girls, pre-teen, and teen girls clothes! Complete outfits head-to-toe, shoes-to-wig, inside-out! ! Eventually my sisters grew older and moved out and eventually most of the clothes were gotton rid of before my parents moved to a smaller house.
Luv and hugs
Patti

[DIANEF]

I was a teen when I first put on a dress (15) though I had worn underwear, tights, swimming costumes and such for a long time before that. It was a sexual thrill but the dress changed everything. Looking at myself in the mirror made me realise that this was what I wanted, to look as much like a girl as I could. It has been ever since. The funny part of the story is that my mum came within a hairsbreadth of finding me in my sisters room (her dress), only a creaky front door hinge gave me enough warning to race to my own room and dive under the bed covers, dress still on. First time I ever wore a dress and I almost got caught!

[Jenny22]

Such wonderful stories! As for moi, clothes hampers, but I was 'selective' in what I wore.... grin.

[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....

[April T]

Didn't have sisters so not too many chances as a teen. That changed when I was 17 and had a girlfriend for awhile. Told her about wanting to wear panties. Over next few months, she would dress me etc. I was hooked. She also introduced me to my first man.

[Maria in heels]

My dressing started "pre-teen" and of course, with my stepmother's heels. I started wearing them at an early age...she was a size 5.5 so I was able to wear them and walk around the house, along with one of my sisters, but I always have first choice and loved this pair of black "Bakers" patent leather platform pumps with a thicker heel from the 70's i'm guessing. From there, it progressed to underwear and pantyhose from the dresser drawers, and no dresses, as they were too big. I do remember as a teenager, getting a dress from the tenant upstairs..it was a beautiful strapless dress that flared out into a full skirt. I finally got enough nerve to go to the local "Rainbow Shops" and buy a white cloth peplum dress that zipped up in the front. I loved that dress and still have it in my storage cabinet. My first pair of shoes were these black patent leather stiletto pointy shoes from Fredericks of Hollywood - back in the days when you had to go to the post office and buy a money order and send it in with the order form. I also bought a pair of white leather pumps, and dyed them purple because I wanted that color...

[Erin.Sometimes]

I started out around 12 or 13 years old, so about 11 years ago. I don't really have much in the way of stories, honestly it was pretty mundane. I was just fascinated by my mom's and sister's clothes and shoes (back when I could still fit in their shoes). Everything was just so different, there was so much variety compared to my array of jeans and t-shirts. I got super paranoid after I started experimenting with makeup that someone would find out. I was worried I wouldn't wash it off well enough and some days I swore I could still smell it on me when I walked in to school the next day, but no one ever really caught on about the makeup. The only time I really got caught was when my mom was going through one of my drawers for some reason and found a couple old Halloween costumes I had stashed away. Took a break for a few years after that and got started back up a couple years ago.

[t-girlxsophie]

I stayed at my grans at weekends and on school holidays and that's where my dressing started around 10yo.There was a lot of my aunties outfits stored there Inc bridesmaid dresses,and even her school uniform,This was in the mid 70s.Can remember the first time I dressed,,although not why.I first wore playtex bra and girdle,black tights Yellow maxi dress and pink button thru cardigan,thankfully my colour co-ordination has improved.This led to me dressing up in my mum's clothes any chance I could get,although I was the worst at hiding my activities and got caught a few times.My mother has never got her head around it ever since

Sophie

[AllieBellema]

The interest began with me around when I was 12-13 when I got the internet and around that time I first saw my grandmother watching movies like The King and I and Gone With The Wind. I started looking stuff up online from there and fell in love with what I saw. I had to be careful at first because my computer was right in the living room so I had to wait until night when my grandparents were asleep and I had the living room to myself. I'd even print a few photos to keep in a magazine in my bed so I can look at them as I prepared to fall asleep. When I got into my High School years, I got a new computer and it was moved into my room where I had more privacy.

Also, my grandparents would let me stay home if I want to instead of going for a ride with them. I'd use it to explore my interests. My grandma was a K-Martaholic. She had tons of clothes to look through and I'd take the time to pick some things out to try on. Halloween 2000, I had my eye on a southern belle dress I loved. I managed to convince my grandpa to let me "buy an expensive halloween costume", not sure how that got past him but probably had alot to do with the fact that my grandpa didn't really care much aslong as I was happy with what I was doing. I nearly willingly showed my grandpa after I got it, on Halloween night. He was talking with his brother on the phone and, during that I chickened out and opted to not show him after all. I also bought other stuff at stores to wear, mostly out of halloween costumes.

The oddest experience was when I ordered myself a large hoop skirt. I paid for it out of money I made and placed the order via mail. My grandpa got the package and held onto it when he thought it was a Christmas present. He came to me with the open package, asking what it was. All I told him was that it was "something I ordered for myself". He gave it to me and walked away without asking anything else. That moment still blows my mind to this day on how he didn't really care much. Anytime I had the house to myself at that point, I would use it to dress up. Of course, as I explored other interests, I sealed up the boxes and kept them tucked in my closet. Eventually, when I went to move away, I marked them as "halloween costumes" and threw them into another storage closet trying to hide the fact. Wasn't until another several years later I would get back into this with full force.

[josie_S]

I told this story in another thread a while back but I love it--I had such a great time even if I was absolutely terrified!

My cousin moved in with us when I was like 16 and she was about 18 and we were roughly the same size since I was little bit of a late bloomer. One night my parents took everyone, including my cousin, away for the weekend and I stayed behind; I can't remember if I made up some excuse--I hope I did just to have this time to myself and try on her stuff! Anyway, as soon as I could I raided her clothes. Then I found her make up OMG. I remember she had blue eyeliner and red lipstick and red nail polish...I'm sure I slathered it all on like a cartoon character but I loved it so much. For the first time, I dressed head to toe minus a wig (but my hair was long then) and I spent that whole day dressing up and trying things on and wow, I was in heaven. Then I found her one piece bathing suit!We had a hot tub and I climbed in and just giggled and soaked and loved the sight of my painted toes above the bubbles of the hot tub. And I knew they wouldn't be home until late the next day so I was free to indulge.

I washed everything I borrowed and folded it and put it all back where and how I found it (crossdressers get good at this, I think) and I would never do anything like that now. I was 16 and of course would never do anything like this with anyone elses clothes today, but what a time. I just wish I had pictures :P

I HAD A BLAST!

[Vintage4sarah]

I think that I have mentioned this before, but there is a vivid memory that stands out the most. I had dabbled in my mother's sister's and aunties nylons for most of my preteen years. I was limited due to my tall height and my female relatives being short. Then in my teen years a golden opportunity lands in my lap and I took advantage of it.

I was a responsible kid that had plenty of jobs around the neighborhood, especially taking care of their pets when they traveled. For three years, I 'dog sat' for one of our more affluent families while they returned several times a year back to Europe. They had an older daughter who was tall. After my first exploration of their wardrobes, I finally got the courage to sample cloths that fit me and I was amazed at what I could create in the mirror. There was even a hair piece and some shoes that fit. For the first time I was 100% dress as a woman and I had the time to enjoy it as their dogs got their exercise outdoors. The realization that I could transform myself and the excitement it brought to me was exhilarating. The seed was planted !

[Crissy 107]

Sarah, You’re lucky the dog didn’t escape, I can picture you running down the block in heels. :)

[Shoelaces]

I guess your story didn't end like all those fantasy stories of house sitters being caught and encouraged to dress.

[TiffanyTgirl]

Sometime around 5th grade I discovered panties, red satin bikinis to be precise. After that, I was hooked. Often spent time looking at the Sears catalogue and JC Penny's. Remember those? Not only did I like the lingerie section for the nearly naked women, I loved looking at all the lingerie and wished it was me wearing it. I also thought that I should have been a girl. Seemed right at the time. I can now buy whatever I want, but still have to fight for the private time to dress up

[emmarinn]

I remember one piece swimsuits being my favorite thing to wear when I was 13 or 14. They are so feminine and I would just lounge around the house in one of them whenever I could. Corsets were amazing, just feeling them tight around my waist was soothing in a way. I remember hanging out too much with some neighbors that were friends with my family. Their children were all girls and I was friends with them. They would let me just be there or use their computer in one of their rooms and that was my chance to wear clothes of a girl in her teens and early twenties which was a bit more provocative but still close enough to my size and shape. I wish I could go back to that time I didn't have wide shoulders or a belly :(

[Vintage4sarah]

Thankfully Chrissy, the dogs were free to roam in a fenced-in yard. The longer they played, the longer I got to savor the thrill of being enfemme !


Sarah, You’re lucky the dog didn’t escape, I can picture you running down the block in heels. :)

[JennaDcd]

I remember from about 13 to 16, every time we'd visit someone's house as a family I'd sneak off when the moment was right and sift through the lady-of-the-house's panty drawer or laundry basket. Two of my aunts wore my favorite style, satin string bikini panties. I'd stuff a pair down my pants, go into the bathroom, quickly masturbate, then return them to the drawer (I never leaked on the panties, so they were returned clean!). Over time I'd eventually get up the nerve to steal a pair and take them home, put them on in bed, straddle my pillow, rub my behind, grind the pillow until I came, then throw them away right away so I wouldn't get caught (wish I would have kept them for more than just ONE use, LOL!). I remember taking a red pair, black pair, and white pair.

Other than that, I remember trying on my older sister's bras, panties, skirts, etc.

[SaraLin]

Funny - about the only time I DIDN'T crossdress, or at least think about such things, was my teen years.
I guess there was just too much going on at the time (school, work, getting my license and car, trying to find someone to like me enough to date me, etc.)

Military life right after High school made it near impossible, but by then the feelings were back.