What were you like as a teenage crossdresser?

[Katie Russell]

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

[Myra Thomas]

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.

[SaraLin]

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.


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.

[Megan Nicole]

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

[sara66]

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:

[Diane Taylor]

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......

[Katie Russell]

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

[Beverley Sims]

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. :-)

[Crissy 107]

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.

[ElianaFrozenflame]

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.

[BrendaPDX]

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?

[Ressie]

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.

[Asew]

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).

[Periwinkle]

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. ^^'

[Majella St Gerard]

I did not crossdress as a teen.

[Jean. Ann]

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

[Confucius]

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.

[Stephanie47]

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???

[JaniceP]

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."

[LilSissyStevie]

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.

[KatieGG]

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.

[Teresa]

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 .

[Pumped]

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.

[Emily Occasionally]

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???

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.

[jacques]

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

[Tracii G]

I crossdressed once at 15 but it was at the request or two girls I played with in the neighborhood.
All the kids hung out at that families house because the had a huge in ground pool.
I had really long hair so they were all the time braiding my hair as well.
The notion to dress me up as a girl was their idea but I liked being around them so I let them do it.
At that time I had no clue what it meant or what I was doing,I was just a kid.

Trying to get into the deep reasons of why we do what we do is a fruitless venture.
I think you are reading too much into all this

[beckypanties]

Add me to the painfully shy column. I don't think it had any influence on my dressing, then or now. Well... it might have something to do with me remaining firmly in the closet. Maybe I would have had an easier time revealing my secret self if I was more outgoing?

[cdinmd206]

I was definitely not shy. People who I went to grade school and high school with, who I have not seen in years are constantly telling me they remember me as either chasing after the girls or girls chasing after me. I don't quite remember it that way, but I do remember I was more interested in what kind of panties and bra they were wearing then having sex. I was so envious they could wear nice satin lingerie I had to be content to wear my tighty whities.

[sometimes_miss]

First; many people will identify themselves as shy; But boys and men typically won't to another man. If a man asks another man if he's shy, or if he's an introvert TO HIS FACE you will get a 'NO'. Many girls will do the same thing. Being shy isn't exactly considered a positive attribute. So admitting to being shy, ONLINE on a forum, means squat.


I was wondering if there is a typical crossdressing path.
Aaaaaaaaaaaaaannnnnnnnnnd we have another on the search for the one, true cause of crossdressing.

There's no 'path'.

There's no single cause.

There's no single feeling that makes us want to do it. Some sexual, some, not.

You're 'pattern' is YOUR pattern. It is not everyone else's. And just because you find a million others who had a similar 'path', doesn't explain the tens of millions who didn't.

If you're trying to find ways to figure yourself out, hoping that there are lots of others who experienced it the same way you did isn't going to help; you're still going to have to chart your own life's past. Each of us is an individual. There are going to be differences.

Seeking quality information from web netizens will get you all sorts of answers, some you like, some you won't. In the end, it all comes down to what you feel, and what you believe.

Search deep into your own mind, grasshopper, and you will find your own truth.

[April Rose]

As a teenager I was obsessed, scared, frustrated, enthralled and in denial.

[Tracii G]

On the shy thing I think a lot of people say that to fit in with the crowd if others say they are shy.
Shyness has never been a problem for me I can talk to anyone.

[GeorgeA]

Your experiences are similar to mine, though not exact. I could draw on statements from several posters as my own. We are all similar yet different, We are all individuals.

[RebeccaV]

This is a super interesting thread. Tons of similarities across the board.

[Becky Blue]

Interesting thread, i am going to buck the trend slightly. As a younger teen I was probably slightly reserved but became much more outgoing from about 15. I believe a major part of my growing confidence came from my ability to be comfortable with the girls, many of my peers were terrified of talking to girls lol. Only years later do i now understand why I was so comfortable with the girls.

[penny lace]

In my teens I was always the outsider I was not shy but was always angry (way to many issues to go into here) I cross dressed extensively, even going fully dressed to school including dress under my school clothes one winter. I was caught several times by my parents or relatives stealing or trying to steal girls things but nothing stopped me. I did have girl friends and I don't think dressing was an alternative for me it was more of an escape.

[Katie Russell]

I am glad that so many of you found the thread interesting. Whilst I appreciate that the answers do not prove anything in particular, i.e. that shy boys will be crossdressers, it does show that there are a lot of similarities in our early years. I also appreciate that not everyone said that they were shy but I'd never expect 100% agreement. If we plotted responses on a gaussian curve I'd guess we'd find a consensus around the middle with various outliers. Again I appreciate that this is not a scientific experiment and people may not be totally truthful but I believe the anonymity of an online forum allows us to be more truthful than a face to face situation. I also do not understand why people would 'lie to fit in with the crowd' if 'being shy isn't a positive attribute'.

Personally I don't see a problem in exploring why we want to crossdress 'Aaaaaaaaaaaaaannnnnnnnnnd we have another on the search for the one, true cause of crossdressing'. Whilst I agree that we are all unique there are still certain things that we all have in common and for a certain type of crossdresser i believe tat there is a common theme as to how it progresses. It maybe at different speeds, ages and final outcomes but there is a commonality.

I have spoken to loads of crossdressers with a similar story to mine, too similar to be accidental. We were of a similar age when it started, we did use it for sexual gratification in our teens, we did stop or at least it was drastically reduced when we left our teens and started dating girls, only for it to return in middle age at which point for many it was no longer sexual to the same extent. Does that sound familiar to many? And if I find a million who do follow the same path doesn't mean I have to find a reason why 10 million don't. They will have their own reasons and maybe they will have something in common with others who don't follow my path.

At least if I have some understanding then I can prepare and at least speak to my wife with some sort of answers. Just shrugging my shoulder and saying I don't doesn't really help which is why I'm trying to discover my 'truth'. And I appreciate that I am forecasting the future but at least I know where I may end up if I follow the path to the nth degree. It seems to be a well trodden path and many of us stop at different points. If we sit on a trans spectrum then at least we can judge ourselves against others to give us some comfort and our wives.

I have searched the web for answers and sometimes what I have read is uncomfortable but it doesn't stop it being relevant to me. I was interested that one member posted about AGP. I have read about this and I know that it is controversial but a lot rings true in my journey. Maybe I am using cognitive bias in looking for similarities as opposed to difference but when the results are uncomfortable I cannot understand why I would want to accept the theory. I try to challenge any theories and if it helps me to better understand myself then I think it is valid that I explore why I crossdress.

Katie x

[Laura28]

I was shy also but not really shy. I had many friends. But meeting new people was tough. I as lucky my mother worked 2 days a week and I would dress while she was out. I remember at about 16 or 17 I got the nerve up to go to an adult bookstore all the TVTS book I was in heaven. This was way way before internet. Was nice to know I wasn’t a freak and others did it also.

[CrossKimmy]

I was far from shy. I had lots of friends and had no problem meeting other people. I just harbored this big secret.

My problem was reconciling this part of me with my carnal sexual urges during these hormonal years.

[Jennifer in CO]

On the shy thing...not on your life. My Mom once said that I never met a stranger that wasn't a friend in 30 seconds.

The "rest of the story"...

I was a "pink fog" case. Just imagine a DADT Mom and a blank wall Dad. Not that Dad was distant, just since I was sick so much we really didn't have a relationship. Being sick meant no sports of ANY kind and limited activity. Hence my Sister became the son my Dad wanted. She did the basketball, baseball, etc etc for him. I never wore skirts/dresses around him, but when my Sister moved out, I got her room...and the left overs in the closet...which I wore all the time. Like by the time I was 17 I had a pantie drawer. Not an underwear drawer, a pantie drawer.
Lots of stories I could tell...

[t-girlxsophie]

I was a typical kid played soccer,rode my bike,play fought and got dirty,Yes I was shy around girls and didn't have a serious gf in my teens.every chance i got i was dressing up in my mum's clothes,or at my grans house wearing my young aunties clothes.Where would a gf fit in with all that.
My downfall was my inability to keep my activities a secret my mum caught me a few times.

Sophie

[marlacd]

Add me to the shy list.

I wish I could say that I went through high school blending into the background. That wasn't the case. A few looked at me as a likely person to beat up. The first few did, because I wouldn't defend myself. I'd finally had enough of it, and made one very sorry he'd done that. Then, they let me be. Why they did, I never knew. I hardly said anything to anyone.

I wanted to dress at any given opportunity. I did, before high school, so I used that as a non-dating alternative. Motorcycles became my other outlet. Both were solo pursuits.

[nancy123cd]

It was different for me. I was a real guys guys...played sports dated girls was popular...but couldn't wait to be home alone and get all girly in moms things!!!

[Tracy Irving]

I was not shy.
Lots of friends.
Worked family business.
Played some sports.
Had a few girlfriends.
...and panties when I could.

[Stephanie47]

Katie, I realize you're trying to find answers to a question your wife may ask. It's the big "Why?" I've read the answers. I don't know if you can arrive at a consensus of opinion. Yes, there are similarities which can be pointed out. Time when most seem to have been attracted to experimenting with women's clothing. The fear and angst surrounding wearing women's clothing. Dealing with non-conformity.

When I read the endless threads of the results or questions arising during "The Talk," there is a common element from the woman's perspective. Are you gay? Do you want to transition? It becomes a can of worms because the cross dressing man also has to deal with a wife's feelings brought on by social norms and expectations.

I've stated many times I told my wife that I do not know why I need to wear women's clothing. I may be able to tell her how I feel. It calms me. My experience with telling a woman I am exploring my feminine side really gets a lot of blow back. If a male feels there was some gender misalignment that is a totally different story. Most people with any knowledge seem to accept the premise this can happen. It's natural for a woman to ask her husband all those upsetting questions. I can answer all of the questions. I can tell my wife how I feel when en femme. I still cannot point a finger at a reason.

If you point to this thread as a basis of determining some sort of commonality you're running into a problem. Any woman who may have taken a basic logic course or statistical analysis will immediately tell you your survey is flawed. Why? Where is the control group? Where are the answers from men who do not cross dress? Teenage shyness with girls always seemed to be a natural affliction. Social awkwardness is not a trait limited to cross dressing boys. Yes, you may be able to show a commonality within the group, but, it still does not answer the "Why" question.

I told my wife I do not know why I need to wear women's clothing. That is the plain simple answer to a simple truth. Remember there are always two people in a marital relationship. Perhaps you should also be prepared to confront her negativity to you wearing women's clothing.

[Shawn Michelle]

My teenage years were filled with confusion, and forced counseling.

First, I wasn’t shy, had plenty of friends, and did all the “guy” things.

Let me go back a few years. For starters, I’m an only child, so no sister to steal clothes from. I can trace my dressing up to visiting my grandmother, who at the time lived an hour away (this was the mid-70s, I was about 5). She had a pair of black leather boots and black leather gloves. At the time, I didn’t know why I liked them, but I would run around her house wearing them. No one seemed to care about it at this point.

As I got older, I became enamored by women who smoked (all the women I knew at the time smoked). I would go through my mom’s magazines and tear out all the Virginia Slims ads with women wearing boots (I was also taking note of what they were wearing). I also started wearing my mother’s boots and some of her dresses.

Around my pre-teens, we moved my grandmother to a house in our neighborhood. This gave me more freedom to dress up with rarely-worn clothes of my mothers that I sneaked over from my house. I also got brave and bought my own pair of boots from a shoe store in the mall. This is also when I started smoking (because all the sexy and elegant women I saw in ads smoked). My grandmother knew what I was doing, but she let me do what I wanted. I did this for about 3 years.

Two things happened that screwed the whole thing up. One day in the pre-teen years, my parents came home when I wasn’t expecting them and caught me wearing my mom’s boots and underwear. The second they saw me I bolted into the downstairs bathroom and stayed locked in there for at least an hour. After I came out and got dressed, we had a long talk about how this wasn’t normal, but it didn’t go beyond that. Then when I was 15 (and going to an all-boys school), my mom found my stash at my grandmother’s house. After that, my parents sent me to therapy for about a year (obviously it didn’t work). My dressing at that point was done. I wouldn’t dabble in it again until I was in college.

I don’t blame my parents for sending me to therapy because I know it freaked them out. Toward the end of the therapy, I convinced the therapist I was “cured”. But the whole time I was going, I could never figure out why something that felt normal and natural to me was so wrong. According to the therapist, “it’s not right for a teenage boy to do this, so stop.”

Now, thanks in large part to the internet (where were you 40 years ago!), I’m comfortable dressing and accept it as as part of my life. It’s enjoyable and missed when away from it for any period of time. I still have much to learn and fears to get over. I’ll probably ask some of you to help me with those fears when the time comes.

Thanks for letting me ramble.

[lingerieLiz]

I was not shy, but did enjoy my fem side. With 2 sisters that encouraged my CDing and being passable I enjoyed it.

[annecwesley]

My father was mentally ill, so I tried to keep quiet and to myself. I was bullied by the other boys. Some of my best friends were girls - I wish now I had confided in them that I wanted to dress like them and be "one of the girls". I was ashamed of my crossdressing and terrified about getting caught or of some adult even suspecting. I was almost paranoid about it which made acquiring clothes very difficult.

At the same time I had a nice slender figure with unusually wide hips for a boy, so the clothes I had fit me well. It was the 70's and I had long curly hair. I could have passed easily, but never tried back then.

[wendy]

I was half shy yet half outgoing, depending on who I was with. People I was comfortable with, very outgoing, but with people I wasn't familiar with, more on the shy side.

As a teen, I preferred quiet times at home, while some friends preferred to party non stop.

[Jaymees22]

Put me in the shy column. I was an only child, we moved a lot and I usually would just have one or two good friends. In my HS year book they said I was quiet in a crowd. Someone also told me for such a quiet person I could make a lot of people laugh. I only tried dressing as a teenager a couple of times and I had graduated by then.

[Desiree2bababe]

No, I can't say I dressed because of the lack of a girlfriend even though I was a bit shy. I started dressing for the mere feel of sister's lovely lingerie and soft sweaters. Once it became known I was a crossdresser, I said the heck with it and went out often to clubs as a girl. It was then that I learned I truly loved the attention men gave to me while dressed. Basically, it was just fun being a girl.

[Angela Marie]

I did not start fully dressing until my late 40's early 50's. When I was growing up in the 60's and 70's fully dressing was a perilous path to take. I always tried on my mothers tights and loved the feel. Too bad I did not start dressing earlier since I have a slight build and probably could have passed pretty easily.

[candice.aihara]

During my early teens I was quite nerdy, somewhat shy, and rather slim for my height. When dressing I went for the tomboy / androgynous look with a feminine flare because it was effortless for me. I had girlfriends toward the end of my teenage years; I didn't dress much then.

[Lana Mae]

I am a late bloomer! Teen years were like most here! Shy, did not date, more fetish type dressing, mostly in only panties! Despite this, one classmate called me, "A ladies' man!" I was able to converse well with both and at all social levels! If I knew then what I know now! LOL Hugs Lana Mae

[Peggie Lee]

When I was 12 almost 13 my girlfriend and I swapped scout uniforms, me as a girl scout and her as a boy scout and we went out selling cookies and greeting cards together door to door. Being born intersex at 12 I really filled out her uniform and got a lot of compliments.

[Alexis00]

I wasn't any more shy than others. Started dressing at 9 or 10 and didn't know why. Went through a few cycles of activity my teen years where I would obtain clothing, usually lingerie, but sometimes a bathing suit. The summer I was 15 I really got into it, experimented with various types of breasts (didn't have the money for forms) and sometimes dressed fully. Tried lipstick but not makeup. Started dating girls at 16 and didn't dress at all that I can remember until the summer I graduated HS.

[Natalie_393]

I remember dressing up any chance I could get, of course I was "borrowing" my sister's clothing until she started to notice things were out of place....So I had to start resorting to buying my own with whatever money I had. the only down side was in the early 2000's online shopping wasn't as popular and wide spread back then, thank god Ebay was around. My other challenges in my pre-teen/teenage years was I lived with my parents and sister and my grandparents so needless to say privacy was hard to come by but I still always seem to find time to dress :)

[Leelou]

I agree that this is a very interesting thread. I love hearing others' experiences when they started crossdressing and their early years.

I wasn't shy at all and had a lot of friends, boys and girls, growing up in a small rural school district. I was active in sports but not a big guy, just average height and lean. I didn't have any sisters growing up so I had very limited access to women's clothes. My mom was bigger than me so I didn't really fit into much of her stuff. The first experience I can remember in my pre-teen years was wearing my mom's pantyhose. I was totally hooked. I didn't own a pair of panties until I was about 14-15 when I was able to abscond with a pair of panties from a friend of a friend's house. I'm kind of ashamed to admit that, but I know I'm not the first or the last to do so. I was desperate to have a pair and I loved having them.

My favorite story about crossdressing as a teen was that I got to crossdress at school a couple of times. It happened during what they called Spirit Week in Jr. High. They had "battle of the sexes" day, which was basically crossdressing day. I was friends with a few of the cheerleaders and they twisted my arm and got me to wear one of their cheerleader outfits. I was in heaven! Several of the other guys were game, and I wonder if I was the only crossdresser in the group. There are even pics of our special team of cheerleaders in the yearbook. I got to do this two years in a row--dressed all day as a girl! Good times.

When I got out on my own, I came out to a live-in GF--this was in my early 20's. She ended up sharing this with one of her girlfriends and soon I was out to our whole group of friends and everything was OK. Mostly my guy friends just didn't say anything about it, and it was all good. Her girlfriend's loved me. This was the beginning of me being out of the closet. I went back into the closet for a period when I was married to a woman that would not accept a crossdresser. I never came out to her, she just pre-emptively told me so. I think she suspected because I was super enthusiastic about her wearing lingerie. So I just lived vicariously lived through her and kept my girl clothes in storage. We divorced and I've been on my own since and been able to dress as much as I please and it's been wonderful.

Sorry for the long post, but I love these kind of threads and enjoy sharing a brief history of my experience.

[MsEva]

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

Same here. Pretty outgoing but the femme side of me has always been there as long as I can remember. No sisters to get clothing from. Had to make due. I found a trunk with some basques and merry widow corsolettes in my attic left by former owner, I took possession of then quickly and never looked back.

[leotard fan]

When i was a pre-teen, i get inlove by girls and leotards more than before, seeing the girls in gym classes and ballet classes. Until today i didn´t stop wear leotards, thights and more... I was very shy. At street and school i was a regular boy, but at home alone (and i spent lots of time home alone) i was always enfemme, and when my mom arrives i wear female lingerie... i never know if my mom know about my cd (i had female cloths inmy closet), if she know it, she never talk to me about it. Big hug to you all.

[rhonda]

Looks like we have the same similar traits and that's why we are here in the forum with lifetime membership

[erinna]

I was not shy nor an extrovert, not a hypermasculine kid though, more intellectual, played soccer, worked on cars, into the mountains on the weekends. Not that girls did not do those things, sometimes we all did these things together. I had plenty of guy friends, friends that were girls, and quite often had a girlfriend. I was probably lucky to have a pretty good time in high school and college. Our parents left us all alone a lot and we got in our fair share of minor trouble and mischeif! Most of the time the people I hung out with were pretty good kids and took care of things on our own without anyone watching over us.

For a cis gender male as myself, I think CDing, is just something that is part of us. Growing up before the internet, without any outside influence that I am aware, I just had a fascination with certain girl things at a very young age. Nobody showed me or told me to try on my mom's or sisters underwear. I just wanted to. When I saw women in magazines and catalogs, I liked the look, and wanted to have that look too, if just for a moment. Those sexy underthings had some sort of power over me, being intimate to femininity, and that was exciting. For years I thought I was the only one and had some stress about keeping it a secret.

[deebra]

As a teenager bras, panties and slips hanging on the close line did get my attention. Did the close line get me started in CDing?

[SHINY-J]

I’ll probably never know fully why I crossdress and what caused it,... but if I had to guess, I think it’s probably because I truly loved women from a very early age.. I remember having first crushes as early as 6 years old... plus, I was a comic book nerd kid and grew up seeing these powerful, buxom, curvy, bombshell women with big hair, and gravity defying figures and bodies wearing shiny, sexy costumes and outfits that left little to the imagination...

Those heroine’s costumes where so similar to the lingerie and clothing styles I saw in Victoria’s Secret and Fredrick’s of Hollywood catalogs of the 80s and 90s... I just began to associate the two together and began imagining what those sexy clothes felt like on a beautiful woman...

But being a kid still living at home with no sisters, I just began to sneak panties whenever I could.. from friends houses from their sisters room... etc.. When I started dating girls in middle school and junior high, I would sometimes sneak girlfriends panties when I could and stash them away.... Feeling them in my hands quickly became wearing them... and then it quickly spread to wanting more than panties... bras, heels, etc... them certain situations came about... like when I volunteered with my senior class to help at clothing donation center and was able to sneak a few items without getting spotted... Another time, I took a job with a new sporting goods store that was opening and my first day was helping to get the building cleaned out and the prior business had been a ladies clothing store... needless say, I snuck as man6 boxes to the trunk of my car as I could until it was completely full... I also went back later that night and went dumpster diving! Lol
Unfortunately, most of it was too small or just boring and dull, but I did manage to get several nice items!

I had a secret duffle bag full of an eclectic collection of panties, a couple of bras that didn’t really fit.. a satin garter belt that didn’t match, but did fit... and a pair of green high heels that were too small and hurt like hell, but I wore them anyway..... none of it matched,.. most were too tight or too big... but it got me through those early years.

Obviously, I kept it well- hidden from everyone else, but I found time to dress whenever I could.

I do remember the very first night living on my own in my new apartment (and I’m going to REALLY date myself here)... was spent filling out the PAPER order form of a Fredericks of Hollywood catalog ordering a black spiderweb teddy, size 14 red thigh high boots, and 3 pairs of size XL panties that would actually fit! I theN Mailed it in with my credit card info written on the form.. lol... it was 1999.. the Internet was around, but nowhere near what it is today!

[Veronica Lacey]

Hi Katie...

Yes, I found my way to endearing myself to female attire as a proxy or substitute for a girlfriend as well. I had come to a limited teenage experience-laden conclusion that I'd be solo for life so I delved more into dressing to make up for the absence of a partner. Even after finding my way into the dating scene and eventual marriage I believe that I had taken to the notion that dressing meant something to me perhaps for connecting to the feminine side within me. Yes, I was a shy kid/teen/young adult even with my sports abilities that attracted friends both male and female.

Feel welcome to pm if you would like to share thoughts on it.

Veronica.

[KarenSusan]

I started dressing at about 9 or 10 and continued every chance I got through high school. I was (still am) painfully shy and never had or dated a girl. Like others, I used to wish I was a girl. I used to be envious of guys who could pal around with girls just as friends (no romance). For some reason I stopped crossdressing in college and then in my 40s it hit me like a brick and now except for having to leave the house I spend all my time living as a woman. For years I thought I was the only person afflicted with this. Thank God for the internet.

[LucyDarlene20]

Since it was the '60s, I was driven to do it and guilt-ridden when I did, and had to hide it. Stayed home when the family took out-of-state vacations. Even had to commit my first lie on a Federal form. Joined Sea Cadets in high school and we filled out standard enlistment forms (which were not used, of course). One question asked "Are you [this, that, the other], a transvestite," etc. That was awkward. Checked "No," of course.

It took years to accept that this is a normal part of me and to discover that it is common. Eventually I got to where I accepted that one day I would be discovered and "Heck, meet the other me." Which is exactly what happened when neighbors dropped by unannounced last week. And they're OK with it. Still worried about the people immediately next door, though.

[Crissy 107]

What a great thread, and to think we thought we were the only ones. I agree with Karen Sue, thank god for the internet.

[Diedre]

I was a typical boy growing up doing all the rough and tumble things, but I was rather small in size compared to others so with inadequate talent and size I was always a bench warmer in school sports.

My mother did sewing and alterations and I was drafted to be her dress dummy which after first hating I came to love. But after showing a little too much interest in wearing the clothes and heels I was replaced by a dress form my mother picked up in a resale shop.

Shortly after that an older female cousin found out about my hobby and offered to help me dress. With her amazing makeup skills and a long, real hair wig she had snagged from a friend I was easily passable. We would spend many a Saturday going out shopping as two teen girls. I really loved wearing the Marcia Brady style mini dresses, bra, shaper brief, pantyhose and wedge heels. It was such a rush shopping for clothes and trying them on in the changing rooms

Unfortunately once puberty fully set in I changed drastically and couldn't pass in a dark room full of people wearing sunglasses. It's been almost 50 years since I've worn makeup and fully dressed.

[dana digs sweaters]

"What were you like as a teenage crossdresser?"

Well dressed with 3 older sisters and a mother of course!
Plenty of opportunities to dabble in the softer side of fashion.
Rode a dirt bike, played football and hockey.
Just normal childhood activities for the area that I grew up in.
Obviously, conversations of wearing female clothes (beyond Halloween and high school Powder Puff games)
was Not discussed with anyone except for my one sister who caught me.
Shy? Nope, adventurous with the neighborhood school age chicas.

[Chancey289]

It wasn't until a few years ago that I actually became serious about my crossdressing (because it took a while to come to terms with it), but as a teenager I did find myself secretly when I could trying on a girl's shirt or some lipstick.

[Tammy Lynn Tx]

I was painfully shy and as soon as I could sell papers, TV guides, seed, greeting cards, go to work for my step father. Trying to make money to prove I was a boy/ man as according to my brothers queers were abominations in the Bible. Heck I was 5, I didn't know what either one was. My sister would dress me up and we would play sisters. But her and Mom always told me not to ever let my brothers know we did that. After my sister passed away, I dressed in her clothes every chance I got. My brothers were both gone from home by then and YUp, mom caught me multiple times. She said I shouldn't dress like that but she never took the clothes. Many years later she told me she had always wanted another daughter. It took me being married 3 times for my current wife to get me passed my shyness. She created a monster, that can now talk to anyone.

[Keira Bea]

I only briefly secretly dabbled in crossdressing on the odd moment back then in my childhood, due to living with my mum and siblings. I was a very shy and socially awkward insecure teenager, often bullied even by my brother due to physical handicaps. This emasculation started early for me since I was a child, such as from school. I never did quite fit in as one of the boys due to the handicaps, and it just went from there right through my adulthood. This is me now taking back some form of control by now learning to own the emasculation without shame as I slowly come out to more family and friends.

[BostonBrenda]

I was so shy and self concious. Wearing my mothers dresses jewelry and lipstick felt so relaxing. My parents spent a lot of time away in the summer, so I had freedom to explore this. It felt confusing at first, I dont know why I wanted to dress up but it felt so good. It made me feel safe and comfortable with myself

[Jessica S]

Not shy at all as a teenager. Very athletic, was popular. No sisters , just brothers. Started wearing a panties and pantyhose at around 5 or 6 yrs. old. Went on to other clothes as I got older. Keep it hidden. Had the house to myself a lot and would barrow moms clothes that I could fit into.

[Stephanie D]

Yup! I started with Mom's pantyhose at early age. Then more. And more. And more! Youngest of all male house, and no "direction", but knew something was "off" from my siblings...
Sports and all male influence still did not steer me away from the Sear's catalogs pages of underwear, girdles and lounge-wear. Even at a very young age, there was "something" there that grabbed my attention more-so than the sports pages??? Let that be something a "therapist" can label me as...

[BostonBrenda]

It was complex, I struggled to appear masculine outside with other but didnt feel remotely masculine. Whenever I wore dresses or blouses at home I felt so different, it was a turn on but it felt so good sometimes Id spend all day in a dress when my parents were away during the summer. I was the lady of the house