Teenage Crossdressing

Like I said in my intro, my first time was in junior high. It was homecoming week and every day had a theme and you were supposed to dress as the theme. Well, Wednesday was always opposite day, so with the help of my sister I snuck one of her dressed into my backpack and when I got to school I wore a dress all day. It was awesome. That was the only time I dressed in public. In my teens I dressed a lot when my parents and sister were out for the night or if I could manage to sneak some of my mother or sister's clothes from the laundry. All the sneaking around was kind of exciting, but I'm so glad I don't have to do that anymore.

I never went out in public dressed but did wear items underneath--knee high 'hose, panties, delivered news papers with mom's nylons & panties on underneath. Late teens, I was sooo nervous buying pantyhose or lingerie, but I did to that and hid it. Then purged, then did it again ... and again...

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Originally Posted by Karan49

Back in 1964, and 1965 when I was 15 to 16 I went out at night (7-9 pm) walking from my home to the local strip mall and walked around. I recall being terrified of being caught or spoken to by a passerby. Then the next year my brother found my stash of clothes and I immediately purged everything. The only thing I did for the next five years was to share my cross-dressing behavior with two women, one a girlfriend, the other my soon to be wife; who I have since divorced in 1978 after seven years of marriage. I did do tons of research in college before I married and told my fiance that the prognosis with cross-dressing was hopeless. There wasn't a cure; and the likelyhood was that it would progress as the years went by. Even with this information we both thought and hoped that marriage would be the cure. Didin't happen. I've been living as Karan since 1988...

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I grew up in the same era and my parents found my small stash of cloths. Grew up with 1 brother and 5 sisters all younger than me. I just knew I was different from my siblings. It made it kind of hard for me on me. I did experience a lot of fear and hurt. My father threatened my well being and my life for the family name if I kept it up. So he said. I kept up crossdressing through my army years and my second marriage and finally stepped out late Thanksgiving Eve 1978. What a rush it was great. Enjoyed every moment.:) Never wanted to go back in the closet again.:o

I walked around the block and had outed myself to my friends:) They think I grew out of it, if they seen me now I wonder what would they say?

I dressed at home since I was 5. But I did not have the chance to go outside until I was away at college at 19.

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Originally Posted by Jennifer in CO

I had been wearing my sisters PJ's off and on since I was 4 or 5 when mom hadn't done the laundry yet or it was very cold out. My sister had an old long sleeved/floor length flannel night gown mom used to make me wear on those nights during the winter or a little short number spring/summer. Past that, my 'real' outting was started by my Aunt when I was 10 and I spent 3 weeks with her and my 3 female cousins as Jennifer. Spent 3 days with the family not as Jennifer but wearing only girls clothes when I was 12. Then spent the entire summer as a girl with my Grand Parents when I was 14. My intent was to transition when I went to college. I started out for 3 weeks wore nothing but girl clothes (pants/shorts/etc - we're talking mountains so it wasn't warm) but during that time I met this girl. We hit it off so I at first toned down the clothes but then I thought this was what I needed to be 'cured' so I quit dressing. It was funny, she thought I was a girl at first and although pretty sure she wasn't a lesbian, couldn't explain her attraction to me. She was very happy when she found out I was a boy. I didn't wear a thing for close to 6 months (except panties) but then I was at her place one evening and we got in a tickle fight and we both ended up wearing the iced tea pitcher on the end table. She went to change and when she came out she tossed me a cute little peasant blouse and a pair of shorts to wear. Once I had them on it was like something turned on in me again. She thought I was cute and proceeded to put makeup on me. Then seeing her finished project got her turned on and the rest they say is history. We got married a year later and that my friends was 33 years ago.

Jenn

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Don't even think about telling us that her name is Juliet. lol

Ok, that was definately a great story and without a doubt, you are a lucky 'gurl"...but you left out the most important part ...does she or doesn't she have a sister? :o

When I was a teenager I would wear my mother's clothes as much as possible and I would imagine becoming a girl but I never had any courage to go out dressed.

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Originally Posted by joann07

For me, crossdressing never crossed my mind in my teens. I started dressing later in life at the ripe age of 37, three and a half years ago. It wasn't until early 2007 when I went out in public for the first time. I was with a very experienced crossdresser and she took me shopping at the mall, thrift stores, and the flea market and then we ate at a mainstream restaurant. It seemed like culture shock, as I was a bit nervous, but I enjoyed it very much. :)
After that, I never went back in the closet.

Hugs!

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37 plus three and a half makes....twenty something isn't it? LOL Prior to 2007 did you ever have an interest in female clothing?You are right up there with all the prettiest gurls on this forum. In 3 years and you look like a GG and obviously pass with all the confidence of a GG.
Hugs.
Patty.

I guess I had the cravings to be out there fully dressed when I was a kid and probably on my teens. Being mostly an underdresser, I fulfilled that part of the crave probably before I was 15.

I've never been out fully dressed with a questionable exception when I took a walk on a (almost) empty beach at night wearing a one piece bath suit. And that was around my early twenties.

I was wearing my sisters panties and bras often, but never had the courage to go out. Then one day i put on my sister's bikini bottom under my own bathing suit. At a nearly deserted beach I slipped off my shorts but kept on my t-shirt and laid in the sun. Even got up and went swimming too! What a thrill!

my first time out was jogging in the middle of the night. crazy. i had a couple old pairs of my mother's pantyhose and my own running shorts and a t-shirt. i don't know what i was thinking. i put my longish hair up in a bow. probably 14-15.

next time "out" was the powder puff football game as a cheerleader my junior year. did that again my senior year.

another significant memory was with my girlfriend my junior year. i told her i was curious what it was like to be a girl and get all dressed up. so we planned a day when i would come to her house (no one else home) and she would give me the "whole nine yards". she styled my hair, did my makeup, i put on her bra and panties, a full slip and one of her dresses. (she was a very sophisticated and fabulous high school girl). i think i just looked at myself in the mirror a while, and then i can't remember what happened.

I had urges when I was young, but buried them. When I reached my mid 30's The "flood gates" opened with a bra. since then I have been adding clothes and shoes when I am able. as far as going out that did not happen until later last year as a matter of fact. :battingeyelashes:

I guess it depends on what you mean by "going out". When I was, 16-17 I went out a few times when I thought few people I knew would see me (like early morning on weekends and at night) dressed in my sister's skirt, top, and shoes.

I didn't start going out fully dressed until quite recently, and I still haven't had the courage to go out to clubs dressed. But I've preferred female clothes as far back as I can remember.

I have wanted to dress as a female occasionally for as long as I can remember - back to being around 4 years old. However, as a teenager I didn't have the privacy, or the guts to go and buy my own clothes. At university was when I first fully dressed in public (except for a wig), for a "drag competition" and I can still remember almost every detail over 20 years later. I also dressed for a party one time and went to a pub first. Had a great time, and again I remember how alive I felt. I wish I could pop back in time and encourage the younger me to just go for it - not full time or anything, but to get a wardrobe and just enjoy it occasionally. I intend to try and make up for lost time now, but family commitments restrict me more than I would have been when younger.

in my early teens, ( age 10 or earler) i thought i was a freak, something was very wrong with me. boys do not want to wear the dress, and "other " things.
my mom even said when i was very young i loved to go shopping with her and the other women in the family.

but with the help of the web...(that al gore built :eek:)--just a ha ha plug--
i have learned i am not a freak, or weird...well maybe a little bit weird.
just part of who and what i am.

but this has been a life long journey, that has yet closed out. (not that a couple have not tried too.)

loni

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I started dressing around age 11 in private. I did not go out into the light of day until my late 40's.

The short and sweet I was 16 I went out for a drive and hung out deep in the state forest all by myself. As for the drive I took the wig off in like 5 minutes and it wasn't long the fear took over quick. I do recommend the camping dressed thing though if you like the out doors that is find a nice out of the way camping spot and maybe at night take a nice long hike trust me it will feel great if you have only done it at home up till then very freeing.

I've mentioned this story in another thread, entitled something about 'your earliest memory of dressing' or that sort of theme.

When I was about 14....back in 1964, I went with my parents on vacation. We visited my grandmother who had very limited room in her small house, so she arranged with a friend of hers that I would stay at her house. She was a widow, and her 34-year old daughter was away somewhere for a few months, and I was given her daughter's room to stay for a few nights. My grandmother's friend worked during the day, so I had the house to myself. One morning, after she had left, I opened up the dresser drawers of the daughter's room, and found dozens of pairs of panties, garter belts, stockings (retro SEAMED stockings too!) this was LONG before pantyhose was invented, bras and slips. Everything of course was white, with only the occasional black item.

As I looked at these things and felt through them, I had this overwhelming desire to try them on. They all fit me because I was very tall at 14 and I remember looking at myself in the dresser mirror and just not knowing what to think or feel, except that it excited me. We were only staying for another 2 days, so for the next 2 mornings, I tried on everything that was in those drawers. I had a fabulous time!

That was the first and only time I ever had either the opportunity or desire to do that - until I reached the age of 30, when I started to buy my own lingerie. It's strange how I just never even thought about it since that first time as a teen.

when i was a younger teen the first time i went out in public was for school homecoming, i had on my sisters jean jacket and skirt, the best thing in the world, that day i WAS a girl.:daydreaming:

First time I remember dressing,i was 10 yo,staying over at my Grans,as I did often back then,just being nosey child,I looked through her wardrobes and drawers,Think the colours attracted me,after that I dressed when I could,getting caught often (terrible at hiding my secret)

First time I went out dressed was during my 1st marriage,when late at night I would spend.Well that soon stopped one night when I cpl hours out dressed in combination of my hidden stash and my then wifes clothing,I think i was 24ishWell that stopped abruptly one night when I unfortunately got cornered and beaten up (thats for another time).

Became Sophie Louise 9 years ago,when had my own place,and have never looked back since,both at home and out and about

i never get out crossdresser, unfortaly. i only use female things underwear, or sometimes when i drive my car at weekend,,,

14 or 15 years old for me........

As a teenager, there was never an opportunity to go out dressered without the entire world knowing it.

I started when I was wayyyyy young I'm 52 now and when I was very young back in the late 60's I remember putting on one of my mothers bras under my clothes and going ti the boys club down the street. When I got there some one asked me whats that I have on and I ran like a cheetah outta there. I never went back out after that untill 1996 I went fully dressed to a Simply Fashions store in Charlotte NC I had been in the closet for all those years but for some reason I just had to go shopping. I had the best SA helping me, I loved her clothes she had on so she fix me a similar outfit. After that wonderful experience I never looked back and know I dont pass but dont really care. I just watch my surroundings and wont stop where there might be trouble.

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Originally Posted by Stephanie Miller

Unfortunately I have to fall back on the old saying “If I only knew then what I know now.”
I denied who I was, and suppressed it behind the McGyver type male. That was until the internet became a main force in daily life. Then I really don’t remember what made me look up crossdressing – but I did. That was about 12 years ago.

Just like you I had no idea what was making me love dressing, and i thought it was wrong also...a therapist told me to look it up!
A time when many of us thought we were the only ones in the world thinking this way. Thinking it was wrong.
Then the lights came on! Damn I’m mad that I missed all those years of youth and the potential to look pretty.

When i first started attending meetings, I said the same thing...if i only knew then what i know now... i would have started hormones long before i started loosing my hair..[all sorts of thoughts like that]

Now I get to look forward to picking out a pink walker and wearing my nylons down around my ankles. Better get a chain for my glasses too :doh:

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Karen and I have often said we will grow old as 2 little ladies with pink walkers...i will be the bald one with the wig!:sad: