What were you like as a teenage crossdresser?

Hi

I was wondering if there is a typical crossdressing path. Whether there are certain characteristics we share that may not be as common in the general population.

I was always a shy child. Painfully shy at time although I was no different in the way I behaved to the outside world. I played football, cricket and went to cubs. I climbed trees and rode my bike. All typical for a young boy. I had close friends but was always quiet at school.

I know that not all shy children will grow up to be crossdressers but it did affect my childhood. I found it difficult to talk to girls in my teens even though I so wanted a girl friend. I loved girls / women. I think that maybe my crossdressing was a substitute for my lack of a girl friend. In effect I became my own girl friend who I could dress in the way I found attractive.

I had a girl in my class who I fancied. My sister had a skirt which was identical to the one this girl wore to school. I used to love to wear that skirt because in someway I could feel what it would be like to be with her. I was substituting myself for her. I could be close and intimate with her by being her.

I was wondering if others here had similar experiences of being shy and not having girl friend. Whether your dressing was a substitute for this lack of intimacy. It would be interesting to see if there is a pattern or if that was just my experience.

Katie x

I was also a very shy child, who didnt mix very easyly, and when it came to girls i was so shy that i didnt have many dates, but i always envied them from afar.
As for sport etc. i wasnt interested or good at anything, looking back it was quite a sad and lonely time, with me constantly just hoping and praying that i would change into a girl. Ah well.

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Originally Posted by Katie Russell

I was wondering if others here had similar experiences of being shy and not having girl friend. Whether your dressing was a substitute for this lack of intimacy. It would be interesting to see if there is a pattern or if that was just my experience.

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I was painfully shy throughout most of my life (I'm not done yet, so who knows?) - BUT for me it seems like I was shy because I was terrified that others would reject me. I somehow thought that If I spoke to others or let them get to know me, they'd figure out my secret and then I'd be in real trouble. My secret? Why, that I should have been a girl, of course.

Funny, but my teen years are about the only time in my life that I DIDN'T dress. I was trying so hard to be 'normal' and fit in that I suppressed that part of myself. Of course, it didn't work long term.

I don't think that dressing was (or is) a substitute for anything. It's just been me - being me.

Probably like many here I lead two lives as a pre-teen, and a teen. 100% boy on the outside, and 80% plus girl on the inside. Lots of guy friends, sports, outside activities, and fishing, cars & trucks, girlfriends, etc. Yet, when at home I would dress every chance, and just wished I had been born a girl. I was extremely envious of many of my female classmates in school. So many pretty dresses, shoes, makeup and such. I just wanted to be like them. Tough time for a kid in this situation. Inter struggles were tough, especially trying to figure this all out. Glad that’s over! Much more at peace these days. Still envious of pretty ladies tho! -Meg

It seems like there is a theme. I was also very shy. I had a few blind dates when I was in my early 20's and didn't have a girlfriend until I was 28. however I don't think crossdressing was a substitution for not having a girlfriend. Mostly because I started when I was 4 or 5. Did crossdressing make me more shy? I don't know. But it has help me though some tough time.

Sara :2c:

I was quite shy as a young boy but was comfortable when I played with the girls on occasion. I still did all the boy things which occupied most of my time but always liked when the chance came to mingle with a girl or two. A girl that lived next house from me was a year older and quite cute and I always had a crush on her and we did hang out together a lot. As a teenager I was still quite shy and didn't date until after high school. My shyness only started to disappear after I got my first job and even more so after spending time in the army. As a young adult and to this day I'm not shy at all...….quite the opposite. My dressing style has always been geared to the type of clothing I find attractive on women......

Hi

Thanks for the replies so far.

I used to swop clothes with my sister when we were really young as part of a dressing up game. There was nothing sexual involved. It was at that age I was told it was wrong and I shouldn't do it. That in effect drove my future crossdressing underground.

I had friends who were girls but never a girl friend at school. It wasn't until I was 18 that I started to date girls which really coincided with me going to work.

I am a lot more confident now and happy to speak in pubic something that would have filled me with dread in earlier life.

The clothes I wear now are those which I find attractive on women. The same as when I was in my teens. If I look in the mirror I wanted to see an attractive girl / woman - somebody I'd find attractive.

Katie x

When I played with the girls I was always one of them.

When with the boys I would chase girls.

What a mixed up life.

But oh so enjoyable when I think back on it. :-)

It does seem like a theme here that shyness was part of us early on until getting out in the working world. I also wished I was born a girl and definitely enjoyed playing with the girls more then the boys. I dressed up in my mothers things and of course was worried about being caught. As far as I know my Mom did not ever find out.

I wouldn't describe myself as shy in my teens, but I sure would have retreated into my shell if I had ever been caught.

I was small and shy, not too many girlfriends. First time I truly crossdressed and saw myself in the mirror, I thought wow, who needs the risk and effort of a girlfriend?

I was also shy and I'm still introverted unless I force myself to be otherwise. Friends use to try to set me up with girls which hardly every worked out. I only ended up with promiscuous, assertive girls because I was shy and ignorant. I also had a fantasy of temporarily switching bodies with a girl so I could please my friends sexually.

I have been quiet all my life. I had a few girlfriends in 7th grade and not again till college. I dressed from 8th grade to 12th grade then purged all my stuff going to college. I definitely think not being with a girl was a small part of my drive to dress. I definitely dressed like the girls I was attracted to (though I never felt like them or wanted to be them). And I was not out, so 100% male on the outside (though I did grow my hair out starting in 7th grade and had for a few years). And most of the times I had the house to myself I would dress. I was confused by it and ashamed of it. I didn't want to become a woman (like you saw on the talk shows back then) so I felt like the only way to be with a woman was to stay a man and suppress any desire to dress. It worked for nearly 15 years (with only a few instances of falling off the wagon into the pink fog).

Ironically, my teen years were the only years I didn't dress. XD

Don't get me wrong, I reeeeally wanted to (and I'd still do it at anime conventions), but I was making a big effort to fit in with the other guys at school. I didn't start to chill out again till after I graduated high school. ^^'

I did not crossdress as a teen.

I was quite shy a loner
Never really dated
Had few friends
Stayed busy working , doing guy things
Thought about girls a lot
What they did , what they wore
What it must be like to be a girl
How wonderful it must be !


Jean Ann

Shy, yes. I perfer the term, "introvert". I was such a classic introvert that when my class had a discussion on introverts and extroverts, the teacher had me stand in front of the class as an example of the typical introvert.

Yes, I found it extremely difficult to talk to girls. I had no girlfriends, but I suspect that there were girls who were interested in me. My social skills were too poor to take advantage of the situation.

I did some limited crossdressing with my mom's clothes. I was fortunate to be extremely skinny and my mom had saved her old prom and special ocasion dresses. When no one was home I would try one on. It would make my whole body tremble and just the touch of the fabric made me feel like I would explode. I would immediately take the dress off, and worry about what I had done. I thought I was the only person in the world who had an attraction to feminine clothing.

In short, I was an introvert, had a low self esteem, had a few good friends, but wasn't popular. My grades were good, and I got along with everyone. I also held jobs typical of teens. Another odd thing about me, was that I believed girls were privileged. I believed society valued girls over boys. Being a boy was believed to be a handicap and subject to abuse from other boys.

I had to do some calculations to figure out what I was doing and where I was way back in the dinosaur age. Early teen years were junior high school. Later teens was high school. I was not shy at all. However, I had no real interest in girls in junior high, although there was one (Linda) who I thought was cute. But, she was not available. My high school was an all boys high school. The high school admission was through a city wide exam. I was more interested in studies and going to college than socializing. That being said there was a lot of male/female group activities. I spent a lot of time doing guy sports. There were not many girls my age in the apartment building I lived in. I had no sisters who were older. A twelve year younger sister. No female cousins. I was a rough and tumble guy who was also a nerd. Nerds can get into a lot of trouble. My wife says I was probably totally bored by school because it was too easy. Probably right.

The dressing? I was lured to wearing women's clothing by my mother's nylon full slips. I loved the feel of the fabric. I tried one on and was hooked. It lead to experimentation with her other clothes until I grew too big for most of them. This brought up a lot of angst. Back in the 1960's, if a man/boy wore women's clothing he was deemed a homosexual. That did not make sense because I lusted after girls. Totally confused. On the one hand I was dabbled in mom's lingerie draw, and, on the other hand I wanted to get into a girl's lingerie. Of course, I feared being found out. I know for sure my parents would have beaten the crap out of me.

Not having a girl friend had no bearing on cross dressing. I just did not find the right girl until I discovered my wife. Been married close to fifty years. I met her several months after completing a combat tour in Nam and recovering from being wounded by an IED (booby trap back then). At that time wearing women's clothing was so far in the past it never occurred to me to engage in it. It slowly crept back after being married several years. I have no idea why. My wife was (and still is) a really sexy woman. Downright beautiful. And was adventurous. Under those circumstances why the hell would wearing women's clothing resurface? Any shrinks out there???

Megan, you and I could have been clones.

The most enjoyable times I had was when I interacted with the girls on my block. They would include me in their various games during the summer months,
in fact, it was like I was just "One of the Girls."

I was painfully shy when I was young but I had no shortage of girlfriends. I suppose I was attractive enough that they were always after me. I never pursued them. I can't blame shyness or unattractiveness for my being a CD. My relationships never lasted very long for two reasons. The first was that I was hopelessly addicted to drugs and alcohol and the other was that, although I enjoyed the company of women, I just wasn't very interested in conventional sex. The sex was OK at first but it wasn't long before it bored me to tears. Women would put up with my addictions to a certain extent but not the lack of sex. I would rather indulge in my AGP and femdom fantasies than have actual sex with a female. I thought I might be gay or bisexual, and my girlfriends would come to suspect the same, except for the fact that I had no attraction to males outside of my AGP fantasies. It wasn't until I came across the concept of autogynephilia that I began to understand what was "wrong" with me.

This is such an interesting thread. Seem like most of you were shy growing up.
Thinking back to high school, my husband was not shy at all. He was kind of a "bad boy" and always in trouble. Not part of the popular crowd but everyone knew him. He was a skater had face piercings and tattoos , girls liked him but he wasn't really a boy friend type. He later told me he never liked to date a girl because then he'd have to hide the fact that he wore panties. We started dating when we were 17 and his cross dressing progressed after that but he had always been loud and a "look at me" kind of person.

Katie,
I guess I was in a male straightjacket from an early age but it didn't figure then so I was just at time a naughty mischevious little boy , I was quiet but not shy and very inquiring , I took everything in and asked possibly too many questions . Then the T kicked in at 8-9 and my brain was wanting things I didn't understand . It wasn't long before the penny dropped and wanted to wear womens clothes yes it was sexual . This carried on till I start dating GFs and very soon found I had met ones that were OK with Cding so it didn't really affect my childhood or my teenage years , the problem was I married naivley thinking all women were OK with CDing .

Sorry it looks like I bucked the trend , I had a tough time at school but wasn't shy because I had to learn to stand up for myself as I did at home because I had a bully for a father . One thing I'm so grateful for is I've always had a sense of fun and a good sense of humour .

My early years I never fit in. In grade school I hated sports but that is all the other boys wanted to do. Mentally, I could not deal with the competition and criticism from other boys when I screwed up. I liked to hang out with the girls, they played hop scotch and sat around and visited during school recess. I felt comfortable with them, but then more ridicule from the other boys so I interacted less and less. This carried on into my teens and I started to notice girls more and more, but was socially clumsy and tended to screw up relationships from the start. I had a small handful of friends, but still did not fit in any where. When I look back I think we were all outcasts. I dabbled in dressing in my early years, then some in my late teens, probably due to the fact that my parents divorced about the time I hit my teens. (I always wonder how much that screwed me up too?!) I had women's clothing available early on, then I went to live with my dad and the supply ran out until my late teens.

I met a girl in high school and we hit it off. In hind sight she was more screwed up than me so what ever I did was ok. We married, but it did not last. She had very poor communication skills and just clammed up when the $hit hit the fan. I met my current wife when I started college in my early twenties and we have been together for almost 36 years. She too had some family and social issues, but was more willing to talk about it. We had some rough times but I believe it has made our relationship stronger.

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Originally Posted by Stephanie47

Not having a girl friend had no bearing on cross dressing. I just did not find the right girl until I discovered my wife. Been married close to fifty years. I met her several months after completing a combat tour in Nam and recovering from being wounded by an IED (booby trap back then). At that time wearing women's clothing was so far in the past it never occurred to me to engage in it. It slowly crept back after being married several years. I have no idea why. My wife was (and still is) a really sexy woman. Downright beautiful. And was adventurous. Under those circumstances why the hell would wearing women's clothing resurface? Any shrinks out there???

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I'm not a shrink but I've had enough therapy that I think I might have an answer for you. It might have resurfaced because you felt comfortable with her. You had to dress in secret as a child for fear of reprisal from your parents as you said. On top of the fact that you didn't understand your compulsion to dress to begin with and felt fear and anxiety because as you said in the mind of many people in the 1960s (and even some people today) crossdressing was the same as being gay. And for a lot of people back then (and again some people today) being gay was "wrong" or "bad" or "deviant." In the mind of a child or young teen in an environment that didn't nurture exploration of sexuality or gender lines or anything like that, you felt like you were doing something wrong and you were disappointing your parents if you expressed this side of yourself openly. Most teen boys wouldn't talk about this kind of thing anyways because of the stigma and as a teen you feel like you're always under the microscope being judged by your peers for any abnormalities. Other boys at an all boys school would jump on that in a second and make your life a living hell if you displayed any kind of "sissy" tendencies. I mean teen boys will say "you throw like a girl" for example if you don't throw a ball that well...the horror of if they found out you liked dressing would be unimaginable to the mind of a young person who is already struggling with the whole idea to begin with. Then you went in the the military and fought in a brutal war where death was around every corner. Not exactly the best environment for someone already plagued with anxiety about the whole crossdressing thing. So you shoved it down since your survival was at stake and not just in a social sense but in a very real and literal sense.

However once you came home and were recovering and met an amazing woman not long after, your anxiety subsided after a life time of being in places where you had no way to explore this side of yourself, you found yourself at a safe port, where the two of you began to build your life together. No longer did you have to worry about disapproval from your parents, or classmates, or teachers, or drill sergeants, or fellow soldiers. You found someone who had accepted you utterly and felt that you could completely open with her. That part of yourself that you had locked away could now be unlocked and explored in a safe way where you wouldn't be judged and rejected by the world.

That's my best guess for you anyways.

hello Katie,
when crossdressing as a teenager I was terrified. Terrified that I wold be caught and terrified because I did not understand why I was doing it.
I guess I was also shy and introverted until I was about 16 - then flipped to be extrovert.
luv J