Teenage Crossdressing

After experimenting with individual articles of clothing, I began dressing fully with make up around 12. It was the mid 70's and longer hair on boys was not uncommon and lent itself to appearing femme. It also led to plenty of singe marks on my neck and forehead clumsily weilding a curling iron! Soon after I was testing the waters outdoors, walking from the garage to the front door and back along the front walk. Across the street was a cornfield but the road was fairly well traveled. It felt so liberating, feeling the warm sunshine on my face and breeze through my hair.

The first venture away from home occured shortly thereafter getting my driver's license. I went to the gas station, back in the full service days when attendants filled your tank. I got a "yes sir"...then an awkward pause...followed by an inaudible mumbling.:o

My HS girlfriend and i used to go to heavy metal concerts, i would usually dress with guy and girl attire, girls boots, fishnet body suit with sleevs, black corset. stuff like that....although it was the 90's and was kind of accepted at these venues.

I was pretty brave/stupid/naive when I was a kid. I remember as early as 11 or 12 years old borrowing a dress from my grandmother's closet when I was there for vacation and walking around the neighborhood. I would walk through traffic and on dark lonely side streets. I look back now and think about all the things that could have gone horribly wrong :( I was very lucky.

From that start, I got even more bold and from 12-18 or more would regularly dress at home (while my parents were home) then sneak out the front door without being seen and walk around the neighborhood for miles. I lived in a very small town (pop. less than 2,000) and now am surprised I was never recognized by people in the cars that drove by. Maybe I was and my dressing has been out in the open now all this time and I just don't realize it.

I would also take long walks in the woods around our house wearing a skirt or dress and hose. Being that far away from home but also 100% confident that nobody would see me while I spent the day wandering in the woods was a wonderful feeling... One of my most vivid memories of those walks was from once when I was crossing a stream on a fallen log and fell in (woman's flats don't have much traction on wet moss!) The stream was about 5' deep and I fell right into the middle of it. I ended up having to walk the mile or so home in a soaking wet full length cotton dress over bra, panties and hose. :(

Probably the most fun when I was a teen was when I had an after school job that included access to the storage area of a local department store. They had racks of skirts and dresses ready to go out on the floor and I could pick something off the rack, try it on, then put it back with nobody being the wiser (all while I was supposed to be doing inventory in the basement).

I'm ashamed to say that I ended up steeling a few things from there, but at that age it was the only way I could imagine actually OWNING my own clothes and the temptation was just too strong.

When I got my drivers license at 16, I started driving dressed and riding my motorcycle with a skirt on... and things continued from there.

I started dressing at about age 11 (mid 70's) I was very small, thin, had long hair, and sometimes got mistaken for a girl in boys clothes! (Wouldn't ever happen now:D) My first tentative steps started with just opening the back door, then standing just outside, progressing to walking down the path, and then once or twice going into town. I definitely remember once because a school mate saw me! The look on his face :eek: I would sometimes skip school and head to a nearby city and wander around far a few hours. My most daring/stupid outing??? I went swimming. Planned it for weeks, got everything I needed together-thank you sisters:love:- and brazenly walked into the building, paid my money, found a single room to change, "tucked", dipped my toes in the water, ducked my head, and fled! What was I doing?? The place was packed and I'd likely get the snot kicked out of me or worse. So I left. But I had got most of the way and my heart didn't slow down for days. When I left home I went back in the closet and there were few outings, although I wandered around Leominster one sunny afternoon! I've spent a couple of Christmases on my own and on one had a wander around north London in a lovely dress and got wolf whistled by a couple of drunken Irishmen. Nowadays I don't go out a lot. Just the one car and my business is advertised on the side of it. Whilst I'm getting more open with my dressing I'd still rather tell people myself than be spotted.
Hopefully though I'll be able to get out a bit this year. And good luck and well done to all you who do already:hugs:

well I nevered ventured out in my teen year or older been wearing my sister panties and bra as a kid and and some dresses around the house when nobody was home after I moved out on my own then I started but nevered gone out fully dressed mostly underdress

Dear Shannon, Although I had a few early times with Mom's clothes and stuff, I really started CDing at age 14. Like many of us my first night "out" was a Halloween. My friend Jonny and his sister dessed me in her (the sister's) cheerleading out fit, and I loved "being a girl". Some may say thatdoesn't really count, but soon after that I was dressing regularly, and especially on "camping trips" with Jonny. It was wonderful to be a girl for the weekends at the campground, and even made a few new friends who knew me only as Willow.

I didn't quite make to crossdressing as a teen, but I sure wanted to. I think most of us start out as mental crossdressers and then just fulfill our desire. When I was 13 I lived next door to a beautiful Swedish-descendant blonde who was my best pal's mother (so I was over there almost every day). She often spent much of the day hanging around the house in her bra wearing jumbo brush curlers, then a perfect teased paige style. She was totally influential to me. I often imagined what it would be like to spend the day dressed as a girl and doing hair with her. I never did, but 8 long years later I moved away from home and immediately started growing my hair and styling it in the same sort of turned under paige style she wore. Full dressing was something that took me nearly 10 more years to entirely get to, but it was inevitable.

I often think back and wonder how it would have been if I could have spent a day now and then in a miniskirt or capris doing hair with my neighbor. I think we'd have knocked 'em dead.

Lyric

When I was in my early teens in the late 70's, I would go through my Mother's things and hold them up. I also took an old pair of jeans and cut the legs off and made short daisy dukes shorts out of them and wear around the house with a unisex tank top and since I kept my hair on the long side then, I would try to comb it in a feminine matter.


Then when I was 16 and in the summer of 1981, my GG Cousin who was the same age would dress me up and since we were the same size( I was quite thin back then) I fitted in to her clothes quite well. She would put make up on me, she had a wig which she put on me and I looked good. I dressed femme with her and dozen or so times that summer and we ventured out to the park after dark one night. Once September came around, I decided to stop fearing if it came out in school that I wear girl's clothes, I would've been called every name in the book. She was dissapointed but understood.

Then January 2008, with the help of my wife, I started CDing again and it ws no turning back. Felicity is out and she's not going back. I now fully embrace my female side.



Felicity :)

[SIZE="2"]I have been dressing every since I can remember. It was always in the closet and no one ever knew. I now wish I'd have gone out dressed as a teen. My wife finally figured out I liked wearing her lingerie and was ok with it. It has finally progressed to the point that I usually dress when we go out and I have also started doing drag shows. I LOVE IT![/SIZE]

There were times when I wanted to wear girl clothes as far back as I can remember but my parents discouraged it some starting when I was about 7 I guess. After moving out I started actually dressing in my early twenties but fantasized about being a woman/dressed as one for pretty much my entire life.

If you mean fully crossdressing, then I never fully crossdressed in my teens. It was mostly putting on an article of woman's clothing (bra, panties, dress, etc.) that got me aroused. It wasn't until this year, when I've turned 20 that I actually dressed full fledged with cleavage and makeup, but never a wig or body modification (shaving of legs and eye brows).

Does that make me different? I want to look feminine but only for that time where I am in the need to crossdress, other than that I want to be masculine with hairy legs and a defined brow.

It's mighty confusing at times... I want to dress full like a woman but then after the initial high off of it, I want to be no where near it.

I have been underdressing since I was 7 or so. I didn't really start wearing dressing fully until I was grad school when I was 22 or so. I started buying my own lingerie as an undergrad. It took until I was 24 to get the courage to go out enfemme and try on clothes at the mall. Since then, my dressing has advance where I can pass pretty well to the point where I can wear swim wear en femme. It is a process.

I think I was around 12 the first time I wore a pair of panties during summer vacation at home while everyone else was at work. I moved up to a one piece swim suit my mother had a year later and liked what I saw. Especially from behind in the mirror. lol My natural long wavy hair added to it, and I would walk around the backyard looking at my reflection in the huge window panes.

I didn't do much til I was... I think 15. I took my mother's blue leotard, cut it up to make a tight top and bottom, stuffed my top with socks, and taught myself how to tuck (the wrong way), and my hair was longer (I was a teen rocker ;) ). Wearing that outfit, I went in our backyard to sunbathe during the summer. Here's a funny.. I was on my tummy when the meter reader attempted to come in my backyard. I'm not sure if he peaked over the gate while opening it, or just opened it, but I heard it rattle and a man say, "Oh! Sorry!" Of course, that made me jump up and run in the house as I was totally embarrassed. lol With my heart racing, I realized I enjoyed being seen. If felt good knowing he thought he saw a woman/teenager. This eventually led me to sneak out of the house after midnight dressed while my family was asleep. I walked a few blocks away to the bowling alley wearing the same outfit (but with gym shoes) where I was seen. I'll leave it at that. ;)

I really have to say I was sooooo lucky a cop or a driver never saw me. I ducked behind a bush once when I saw a police car. lol

Hello all!!!

I am brand new to the forum and thanks to Tamara for helping me with my circuitous path to registration! I'm sure the effort will be worth it!!:)

I am in my early twenties and have been an enthusiastic cross dresser since as early as I can remember. I'll post my whole story where appropriate and try to work on my profile soon too....

As for this post, well I can remember I would slip out of the house around 11 of 12 years old fully, and I mean fully, dressed. Usually I would fake sick to stay home and dress up. We lived in the country surrounded by woods and the nearest house was probably about a quarter mile away. I decided early I that I needed to be outside dressed in girl clothes so I decided I would walk to the mailbox after the postman delivered the mail. I can still remember standing there in a dress and heels looking out the window of the storm door, glancing back and forth to make sure no one was around. As if the woods were full of people waiting to jump out and yell, "Look a boy in girls clothes!" I think we all know that paranoia. My legs were like rubber when I took my first step outside. I was a bright day and I scurried down the drive and stopped behind a tree near the mailbox to see as far up and down the road as I could. Then I made it to the mailbox, grabbed the mail and scampered back up to the house. My heart was practically bursting out of my chest with each beat. After a few minutes when I realized that not only did no one see me but I had been successful in walking outside in my girl clothes (borrowed surreptitiously at that time) I was exhilarated.

From that day forward it became easier and easier to walk outside and I especially enjoyed getting the mail. I can clearly remember how I became so comfortable with it that on clear , sunny days I would bring the mail back to the house and sit on the front steps sorting the items. I always wore Mom's pantyhose and I loved the way they looked in the sunlight. I really loved the feel of a slight spring breeze on my legs.

Beautiful memories.........

I started when I was 12 or so and was of course taking my mom's clothes from her closet. She had a really beautiful blue bridesmaid dress that I remember. After I got out of the house at 18 I began to go out in college to classes wearing baby doll shirts. I went out a few times to some clubs dressed up but other than that I didn't do a whole lot. Sometimes I'd wear a bra or something around campus. Mainly it was the clubs I went to with friends that I'd be out in public.

I started by taking panties and slips out of the laundry when I was 8-10 and then would wear one of my mom's or sister's dresses around the house when I was alone.The first time I went out the door was when I was 17 and that was without make-up or wig, just lingerie and moms dress and heels. It was just in the back yard but there was no fences just trees.I walked from the house to the road that ran behind us about 30 to 40 yards each way.:love:

For me, it began solo around the age of 12. I had thought this was when it began for me but only recently have uncovered memories that it actually began around 5 or 6. I have never been out anywhere or around anyone as of yet.

Hello girls...been away from this forum for awhile.....into my girl side early age. as you can see from profile/bio...out in public(NYC of all places)at age 15 with the GREAT assistance of my older sister.......never turned back.....hello again to everyone!!!

Molly, nice to meet you! You look stunning!

I started pretty early, elementary school, "borrowed" things from mom and sister. Nothing fit.

Fast forward to junior high. Now things were fitting. I was the first one home and I would dress in something everyday. My parents always asked why all the shades were down. My dad caught me one day and quietly explained that boys who wore bras were sick. That taught me to hide better.

In high school, I 'borrowed" a two piece bathing suit from a neighbor (I know) and brought it to a deserted lakeside where I went swimming. What fun! What crazy tan lines. I sun burned my back like crazy trying to erase the lines.

I was in college before I went out and had other people see me. It was always the typical late night gas station stop type events.

I now wish I had done more at that age when the skin was clear, the stomach was smaller and the hair was on top of my head.

Ahhhh... those were the days! I could get home from school, and get dressed and be out of the house in 10 minutes! Quick walks around the neighborhood, and back before anyone else got home-[I hoped!] I was about 15 when I started my "outings"!

I started dressing at the age of 13, and like many replies to this thread, it was the early 70's. I was a teenage boy with this overwhelming urge or desire to wear something feminine. I didnt care if it was my sisters or moms. I could go in the bathroom, lock the door and put it on, whatever "it" happened to be. I just knew it felt good, it felt right.

As for "going out", it took me a number of years before I could even attempt anything close to that. So after I was in the Navy I would drive from San Diego to home and back on some long weekends when I could. It was about 1000 miles each way, plenty of time to play while I drove, mostly at night. But I guess I was about 20 or 21 the first time I was able to be outside somewhere and everything I was wearing came from females that donated to my cause. (not all knew they did,) lol. As the years move on I always buy my own things now,,, Honest,,

I was 22 when I first completely dressed up in my wifes jumper and blouse and pantyhose and heels and wig and makeup and drove 25 miles to the college I was attending and walked around there and then went to a large dept. store and walked around and used the ladies room and then stopped to get gas at a station where they pump your gas and it was a bit awkward to talk to the attendent but he was OK with me I guess - - it was such a great first day out on the town and I loved it - Ellen

I never did Shannon. Wish I could have.:hugs:
Angie

I actually wish i'd spent more time dressing in my teens. The town i lived in was pretty quiet and my garden was not over-looked. Plus i had my own long hair and the usual softer skin etc.

As for going out i would go for walks if i had an empty house or out into the garden for a smoke. At the moment i live in a tiny village. The best i can do is the smoke in the garden but have to wait till it's pretty dark.