Crossdressing in teenage: discoveries, doubts and insecurities

[marieclaire]

Crossdressing in teenage: discoveries, doubts and insecurities


Most people who practice crossdressing discovered themselves in their teens.

Crossdressing is the practice of wearing clothes and accessories belonging to the opposite sex. In this article, we?ll be talking specifically about guys who like to dress like girls.

Although some are fascinated by women?s clothing already in childhood or only in adulthood, probably the stage where crossdressing emerges is in adolescence ? or even in pre-adolescence. But why?

This is the phase where young people begin to develop and the differences between boys and girls become more evident, for example: Boys have a wider body, more body hair and a deeper voice as they grow older. Girls get slimmer waists, develop breasts, start wearing bras and learn to apply makeup.

When I was about 11 years old, I noticed that girls at school started wearing bras and I was curious. I decided to secretly try on a bra from my sister. I enjoyed the experience and did it other times. On cold days, I would go to school wearing a bra under various clothes.

As an adult, I started buying my own bras and decided to try new things, like panties, tights and dresses. But my entry point into crossdressing was when I was a teenager hiding in my sister?s bra.

Crossdressing in adolescence, like anything that is out of supposed standards, is still a challenge in families and society. Many parents do not understand how their child can like women?s clothing, and society does not accept this as something ?normal??

We are not talking here about transsexuality, when boys identify with the female gender, but about boys who like to wear feminine clothes and accessories. They may like to do it out of curiosity, because they find women?s clothing more beautiful, because they like the feeling of wearing it or because they feel some kind of attraction, for example. It is not a disorder, but a form of personal expression.

This is an issue that needs to be addressed because many young people do not know what to do when they discover that they like women?s clothing and many parents do not know how to deal with it.

Teenagers can come into conflict with themselves when they discover that they like women?s clothing and have emotions of shame and guilt, for example. They may also feel confused or repressed for not fitting into a supposed standard imposed by society, which could also hurt them through prejudice.

Parents can fight with their children if they discover or even catch them wearing women?s clothing. Many do not accept it and end up repressing it for believing that it goes against their beliefs and for fear of society?s reaction.

Probably many crossdressers who discovered themselves as teenagers would have been happier if they could have expressed themselves confidently at that time. But surely many would be confused if their children also expressed this desire.

It is necessary that people have access to information to better understand crossdressing and that it is not a disease or disorder. With more information, young people, their families and society will be able to understand each other better. In addition, therapy is also a good way for young people and their families to understand and get to know each other better.



* When did you discover you liked crossdressing?

* How did your family deal with your crossdressing?

* What would you do if your son was into crossdressing?

[Karren H]

I started when I was 7 and my parents never found out. Our son is gay and we handled that just fine. His partner just came out trans. Just another twist and turn in modern life.

[Saralee]

I can't say how old I was for sure but definitely grade school age maybe 7 or 8. My mom had these navy blue leather slip on sandals with heels in the back. They just looked neat and so I just tried them on. They were easy to slip on and so I just practiced walking around the living room in them. I remember I heard my older sister coming so I had to hide the shoes under a chair really fast. My sister used to tease me relentlessly about girls and if she would have seen that it would have been the end. My family never knew as far as I know. I never would have wanted them to know.

[bridget thronton]

About age 13 (mother's clothes). Never caught by parents. If my kids cross dressed I would have supported them.

[alwayshave]

I started dressing when I was 4 or 5 years old.

[Jillcder]

With my mothers help i wore a dress at one of my elementary schools Halloween party after that I remember my early teens really kicking in strong I dressed in my sisters clothes when everyone was out of the house. To the best of my knowledge they did not know I dressed.
I do not have any sons but I firmly believe I would be accepting.

[Bea_]

* When did you discover you liked crossdressing?
I didn't officially crossdress until my mid-fifties. In my early teens, I'd put on my mom's or my sister's bras that were left to dry in the bathroom to have something feminine to aim my testosterone at. There was no sense of wanting to wear a bra other than that. My mom nor my sister had any style that I'd want to emulate.

My wife was beautiful when I met her (and still is) and her style was as mesmerizing as her smile. I never really considered wearing her clothes for the first few decades. A couple of times in my thirties, I tried on various items, but it was just curiosity that was satisfied and forgotten. (I really wish I still had my fifty pound lighter physique from my thirties. Feminine options would be MUCH greater now)

In my fifties, after some extensive, drawn out trauma, I developed an interest in wearing panties and discussed it with my wife. She bought me my first nice panties and things have developed from there.

* How did your family deal with your crossdressing?
N/A

* What would you do if your son was into crossdressing?
My son was grown and married by the time I first started dressing so it would have been unfamiliar territory for me.

I think I'd have tried to make as much of a non-issue as possible. I'm afraid his mother would have shamed him badly if that had ever come to light. I think I'd have run interference in that respect, even if I didn't understand it. I'd also warn him that that path would not be an easy one.

[Michaela Jane]

I didn't begin crossdressing until I was in my early 50s. It's strange how I started because I was looking for a particular underwear item & couldn't find anything I liked. Out of the blue, I asked my wife if she minded me looking at the womens dept to see if they had any that appealed to me. She said that was OK & I found exactly what I wanted. That was the start of my slippery slope.

[Celee]

I was 9 or 10 when I started. I found a pair of my mom?s panties in the laundry hamper and curiosity got the best of me. I would sneak them into my room in the middle of the night. When I was a couple of years older I would stay home by myself and thats when it really started.

[tifftg]

I was 12 or 13 when I started experimenting first with my mother's and then my sister's clothes. My mother caught me once when I was 15 they came home early from a trip. I told her it was the first time and she never discussed it again and they never caught me again.

My son is gay and we supported him.

[JesseVF]

So early I don?t know for sure - around 5 give or take. With three older sisters and mom there was ample opportunity to play and things just felt good/right. Always felt I should have boobs.
I think my sisters may have noticed things - one time for sure when she found one of their lingerie items under my bed where I had forgotten about it. However nothing ever said to me. Also my mom found me playing around with sisters bathing suits once but a stern ?stay away from those? was it.
Hard to say exactly how to handle the hypothetical if my son was taking part - depends on the specifics - but would certainly support him in a positive way as much as possible- at least it?s better now than the 60?s world.

[MarinaTwelve200]

One bad thing, especially in past decades, (and often still floating around in adolescent circles) is that "Cross dressing means you are gay" . Many "uneducated" adults still believe that., combined with Categorizing Gay, Transgenderisim and Cross dressing in the SAME "basket". Can make for a difficult time for those who discover they like cross-dressing. Kids (and often their parents) should KNOW the definitions of each of those terms, and not get freaked out over it. Well, of course all three groups cross-dress (the verb) but for drastically different psychological reasons. Even if one is not entirely "woke" and is prejudiced against "gays" for example, there is an "out" if they decide they are only a "crossdresser". I think you get the idea. It is the Myths and uncertainties that vex beginning crossdressers and how much they (or their parents) subscribe to them. Fortunately, at age 13, I was a "bookish " kid, so I hit the psychology books and found out WHAT I was, and learned the correct definitions before I got too upset and began to "suffer" out of ignorance as to my proclivities. I stayed in the closet and kept things secret, though because I KNEW my parents, schoolmates, and the public in general, were generally ignorant, and highly intolerant. I didn't wanna be persecuted, abused and called something I was not, because others were too lazy to learn the proper definitions. At least I was comfortable with myself.

In the mid 1960s, Most people I knew and my parents were highly hostile to "Queers" the catch-all term for Gays, Transsexuals, cross-dressers, etc. And were all defined the same, "A man who thinks he is a woman" characterized by acting effeminate, dressing like a female and prone to abuse kids. Having to deal with such a definition One can easily see why a young cross-dresser can be concerned, and in my opinion, HAD to be insane to actually go "public" with it.

I Still am in the closet, although I have gone out on Halloween and for a "Womanless beauty contest at church.

If my son got into Cross-dressing, I would not freak out. I would first ask him questions to determine if he is only a crossdresser, or something MORE "complex" like Gay or TS. I would make sure he had his definitions straight to avoid personal (and needless) "conflicts" within himself, warn him of the RISKS he would be taking if others found out about his "hobby" and let him take his own chances if he wanted to go out. If he gets into "difficulty", he wouldn't say I didn't warn him.

If he actually was to be Gay or TS, then he could get proper "counseling" to deal with his situation. I could live with that. What I would NOT want is for him to think he WAS Gay or TS and not really be. It could lead to a hard life of abuse, terrible mistakes, all for nothing.

[NancySue]

I was 6, when our next door sisters, who enjoyed playing ?dress up?. One rainy day, they invited me to join them. At first, I had no interest. That is until I found nylon stockings. They helped me slip them on. I?ll never forget the electricity. I acted like it was no big deal, but obviously it was. I wore them as often as possible. As we know, CDing is progressive. Over the years my dressing included more and more. Now retired, I dress daily, panties, bra and hose.
My parents never knew. I told my wife before we wed. She?s totally supportive.
I have two daughters, neither know.

[Amanda77]

As i have said before, i started around 12. Was looking for something in the closet across the hall from my room and found a box of my older sisters (i have 3 older sisters) outgrown clothes including undergarments. Curiosity got the better of me and took a training bra and panties to my room and tried them on and loved them.
And it snowballed from there.
Did i get caught, well mom found them in my room and put them back several times but didn't say anything.
If i had a son that crossdressed i would support him totally.

[sara66]

I started with a bra when I was 4 or 5.

I was only caught in the act once when I was about 8 or 9. Mom just said those are not yours, and left it at that. I am nearly 100% sure mom knew. She kind of hinted at it a few times. I am sure mom would have been fine with it as long I stopped "borrowing" her and my sister's things. I wish my mom was still around, I would have really like to talk with her about this. I also believe she might have thought I might be gay. I was a late bloomer and did have my first real date until I was 28 and didn't get married until I was 39. My dad would have freaked out a little. I have found out my dad was probably bi-sexual and had some mental heath issues. I have never been sure if they were related or wholly unrelated.

If I had a son that we caught dressing I would have my wife speak with him. I would have her let him know he is not alone and we still love him. I think having dad or any older male speak with him would shut him down. I know I would have related better to my mother.
I would not let him know I was was also a crossdressers. That would be weird for everyone. Your kids don't need to know your business.

We are lucky we have the internet today. I remember feeling I was alone in wanting to wear women's. We still don't know why but everyone's journey is a little deferent.
Sara:)

[Becky Bloodstone]

I was fascinated by crossdressing very young. I always loved seeing RuPaul on TV. I never did anything much when I was younger. I don't have a sister and my mom's stuff was way to big of course. My dad wasn't a very nice person and would definitely not have been understanding with something like that so I could only imagine would would have happened if I did make an attempt and got caught. I mostly stayed with small things like a bracelet or a cheap ring a girl would wear, i had a ankle bracelet that i loved and wore throughout my teenage years. I didn't start fully dressing until I was 29. My family doesn't know and if I found out my son was crossdressing I would be supportive.

[Stephanie47]

"When did you discover you liked crossdressing?

When I first dabbled in my mother's lingerie draw I hated it! I felt disgusted. I was filled with self loathing. Why was I doing it? Yes, there was an unknown attraction. It did not make sense that a teenage boy who lusted after unobtainable starlets of the movies or neighborhood young women would feel the need to wear his mother's clothing (I had no sisters or female cousins)?

"How did your family deal with your crossdressing?

My family, mother and father, suspected and tried to catch me in the act. They never confronted me with their suspicions; Why was the strap on my mother's sole black bra broken?" I am sure, if I had been caught, I would have been tossed out of the home when I turned eighteen. There attempts to catch me was just before my eighteenth birthday.

[Lorna]

I have, I think, reached the end of my cross-dressing life (but not, I hope, life itself!) and can look back over many years to when, as MarieClaire wrote, I "discovered cross-dressing in my teens". We all have different approaches nd experiences and things have changed so much in those intervening years. I have started writing what is supposed to be a summary of my 65+ years of dressing and wonder whether I should post it on this forum. Inevitably it will be a long post - but probably my last one as an active contributor, though I would like to go on enjoying reading, and occasionally commenting on others' posts.
Would such a "biographical" summary - even a long one - be acceptable? I wouldn't want to offend anyone.

[Sometimes Steffi]

Why don't you post in in shorter chapters? Like some of the others under "Writers Society" sub-forum?

[Lorna]

Thanks Sometimes Steffi. I would be quite happy to do that.

[Gillian Gigs]

When did you discover you liked crossdressing?
I started off in little differently than most of us. Initially girls clothes were used as a punishment when I was bad, always with nylon panties. As my much older sisters married, I moved into the basement bedroom across from the laundry room. I was around 12, seeing all those items that were once a punishment hanging to dry after laundry day. Growing up, I had continual thoughts and fantasies about girls clothing, especially dreams. I felt drawn to once again wear what had been instruments of punishment. I eventually moved on to my mothers dresser drawers, and all of her clothing.

How did your family deal with your crossdressing?
I thought that no one could know about my activities, but now I realize that my mum must have known about it. As I would regularly raid her dresser, I must not have returned, or possibly soiled some of her items. One day I found that my favourite items had been removed from their regular place. I found them in another drawer. They would be washed regularly and returned to this new place. Not a single word was ever mentioned to me. It never occurred to me what was happening until many years later. She would occasionally discard some of her old clothes into a closet in the basement also. I always thought that if anyone knew, I would be getting punished and grounded for 'life' by my dad.

What would you do if your son was into crossdressing?
I would talk about the mess that comes with this habit/life style. I would talk about the guilt, shame and social issues that surround crossdressing. I have often wondered how things could possibly have been different if I had known what I was getting myself into. I would let him know how important, as well as how difficult it might be to find an understanding, and accepting spouse. I would impress how important it is to be honest and open with a potential spouse before marriage. Teach him that compromise is an important part of a marriage and that he can't always get what he wants.

[Jessica Secret]

When did you discover you liked crossdressing?

I was probably 11 or 12 when I discovered my mom's romantic nighties & lingerie, and I was immediately hooked. I'll never forget trying it on and being in a state of ecstasy, it was incredible. I started wearing romantic lingerie or satin pjs to bed every night at 16 and I've never looked back.


How did your family deal with your crossdressing?

Didn't know until I was 18, my mother supported me and even bought me some lingerie for my 18th birthday. Rest of my family never knew.


What would you do if your son was into crossdressing?

I would fully support him in any way I could.

[Heather76]

* When did you discover you liked crossdressing?

I guess the correct answer is around age 12 or 13. When home alone, (rare with 2 brothers in the home) I would put on a bra of my mom's. I would also put on her girdles. This was in the late 50s when girdles were quite common. I stopped this when I was 16 and started dating. I was then married at age 20, joined the Navy, and was discharged when I was 24. Sometimes between ages 24 and 35 I would on rare occasions put on my wife's pantyhose. I was always aroused when doing this. However, I really didn't realize this constituted cross dressing. I always thought of cross dressing as doing the whole "en femme" thing.

* How did your family deal with your crossdressing?

Nobody ever knew of these activities. I would guess during my youth I likely put on my mom's things 10 times in 3 or 4 years. I probably put on my 1st wife's pantyhose 5 to 10 times in 17 years. I didn't start truly cross dressing until my 2nd wife and I were married 36 + years and I was 74. She's not a fan but accepts that I CD.

* What would you do if your son was into crossdressing?

My son is now 50 years old. If he told me he enjoyed cross dressing, I'd throw my closet door open and suggest we have a girls' day out together. While we never know 100% what our children do, I'd be about 99% certain he's not into CDing.

In retrospect, I wish CDing was socially acceptable with no stigma attached to it for the past 70 years. I believe I may have started CDing regularly in my teen years and lived as a MIAD the past 60 years.

[Bobbysue]

Not sure how old I was. I'd wear my moms full slip it fit like a maxi dress and her heels. The I found how panties fellt.They never said anything but mom had to know. I probably didn't get everything back in place.

[Claire M]

*When did you discover you liked crossdressing? When I was 13, I saw a pair of my sister's panties on the bathroom floor. At first I was just curious but as soon as i picked them up, I HAD to know how wearing them felt. A couple weeks later it was the same with her bra. And so it went with pantyhose, dresses, makeup,....

* How did your family deal with your crossdressing? My parents and siblings never knew. My children also don't know ... only my wife and we don't talk about it much.

* What would you do if your son was into crossdressing? My son is now in his 30s. If he's dressing, it's his deal but I would support him. My only advice would be to not hide it in his relationships. If I had found out when he was a kid I would still support him and tell him he wasn't doing anything wrong. But I would also educate him on the hard realities of our society. It's just clothes but a lot of people see it as something dirty and perverse. If you put this out there, be ready for the consequences.

[Melinda Jean]

* When did you discover you liked crossdressing?

I don't know that I "discovered" crossdressing more than that I was always attracted to feminine clothing. My earliest memories are of trying on my mothers heels at the tender age of 5 or do. The draw really kicked in when I reached my early teenage years and began babysitting and numerous opportunities presented themselves to try on women's clothing. The couples I provided that service for were mid 20's to early thirties and the women possessed an amazing variety of current clothing styles (at the time) and shoes that I got to try on. Probably not the best move, but I was young and stupid.

I want to state up front that none of this activity involved the children I was babysitting. I always waited until they were asleep to experiment. After I graduated high school there was no turning back. I am still actively dressing to this day.

* How did your family deal with your crossdressing?

They still do not know even though I am in my mid 60's.

* What would you do if your son was into crossdressing?

I would support him if that was the case, but I have no current information that this is the case.

[SaraLin]

* When did you discover you liked crossdressing?
My first thought when I read this was to smile and a temptation to say "I don't like crossdressing, but the world insists that I dress like a boy."
On a more serious note, I'd have to answer that I can't remember a time when I didn't want to dress feminine. Even as a little kid, I wanted to - and would sneak a dress or skirt (or something) of my sister's to put it on in secret.

For me though, it wasn't the undergarments that drew me. I wanted the LOOK - the dresses, skirts, whatever made me (in my eyes at least) look like a girl. After that came slips or petticoats (yes I go back that far) to "fill out" the shape of the skirts. It was only later on that I cared about bras or hose. By then, if I wanted to have the proper shape, I needed boobs and mine were NOT growing - so a (stuffed) bra became necessary.

* How did your family deal with your crossdressing?
For the most part, they never knew. I did get caught one time with some of my sister's things under my pillow, and told to leave her things alone - but that was about it.
MUCH later in life, I finally told my mother and sister about my "trans-ness."
My mother said "Oh, I thought you were going to tell me you're gay" and that was that.
My sister commented that she'd always wanted a sister and that was about all she's ever said.
So- I'm left wondering if I missed on possibilities when I was young. I can imagine how my brothers would have reacted, though. So there's that.




* What would you do if your son was into crossdressing?
I always felt that I was too much of a mess to have kids, figuring I'd just screw their heads up too. So - I never had kids.
If I were to imagine what I would do now, I think I'd be supportive and understanding, with a word of caution about the difficulties.

[Debbie Denier]

When did you discover liked crossdressing? At 10 years old put on a pair of my mums tights/pantyhose. Changed my life forever. Progressed to panties, slips , high heel shoes , dresses full outfits .
How did your family deal with CD? My dad freaked out couldnt handle it. My mother more sympathetic when I came out to her later in life. Wife reacted same as dad. What would you do if your son was into CD? I haven?t got a son only daughters . However if I did have a son I would support him in every way I could.

[Geena75]

When? -- I discovered I liked wearing pantyhose when I was about 12 or 13 stealing a discarded pair of my older sister's. I didn't get into fully dressing until about 12 years ago.

How did family deal? -- None of my family has ever known. The only people who know about my 'peculiar pastime' are other crossdressers.

What would I do if? -- Difficult to say since my son seems vehemently opposed to such things. I would probably give him a lot of warnings of things to avoid. He is in his 30's, married with 2 children, so he can choose his own course. Would I tell him about me? It would depend on the situation.

[kayegirl]

When,,,, There was a family of four sisters that lived nearby, their father worked a permanent night shift, so they had a large outside shed area to play ib. Inside was a big dressing up box, and I played dressup from around the age of five. But the youngest of four siblings, it was not until I was 13 that I was ever home alone.
I still remember that Saturday evening, parents out, other siblings away for the weekend, and I went into my sister's bedroom. Took off all of my boy clothes and dressed fully as a girl. Got the fright of my life on stepping out of the room and saw this girl looking directly at me. It took a few seconds? before I realised that the girl was actually my own reflection in a full length mirror at the top of the stairs. And that was my personal epiphany, from that moment onwards I would dress whenever the opportunity came. 60+ years now.

How diid my family deal with it. Can't say for certain, I believe that my parents knew, but I was never caught, so nothing was ever said directly.

What would I do? Again can't really say, both of my kids are now in their 40's, with kids of their own. I'm fairly certain that both would be supportive of tgeir boys, whatever.

[Christina89]

When did you discover you liked crossdressing?

I remember I was about 12 years old when I discovered the "pre-teen" girl in me. I was home alone one day after school watching tv, I was watching a show called Totally Spies. The main characters were out and about buying clothes for themselves. As I was watching an old memory popped in my mind where I asked my mother why I couldn't buy some of the clothes the girls were picking out for back to school. I grew up with what we all call an extended family and at the time the family had 2 daughters. 1 was about 3 years older than me and the other was about 2 years younger than me. My mother told me I couldn't cause they were girls clothes and deep inside I was deeply disappointed cause I liked the way they looked. Fast forward back to watching Totally Spies and something awoken inside me. Without missing a beat I went upstairs to my mother's room and started looking around. I found one of her bikinis on top of a box going into storage for the fall and winter. I decided to start with those. I took them and went into my room since it was in the back of the apartment and away from the street, the street we lived on was the main road into our neighborhood. I started to strip down and as I was putting on the bottoms I felt the awaken getting stronger. Then I put on the top and tied it up and the awaken came fully out. Afterwards I went to the bathroom and checked myself out in the mirror. I loved the feel of it on my body and had to admit my male breast looked amazing in the bikini top. After seeing myself for a few minutes in the mirror I went back to my mother's room and found a skirt, bra and top in her room and grabbed them. I returned to my room, took of the bikini top and put the bra on. I didn't struggle cause for a short period of time when I was 5 or 6 my mother and I lived in a one bedroom apartment and at times I saw her put the bra on while waking up. After putting on the bra I put the skirt and top on. I returned to the bathroom and saw Christina looking back at me with a smile on.

How did your family deal with your crossdressing?

I remember during that first year or so of my crossdressing my mother found a stash that I had of hers in my room, she asked me about it and I told her I never wore them (big mistake), then about a week or so later I was with my father going to NH for a week and he asked me about it. I told him no I didn't wear them and lied saying they must have ended up in my clothes when I did laundry and that was it. After another go around I tried to hid them better but failed another time and failed that time as well. My mother didn't say much. Flash forward a few more years and I started to buy my own clothes and my mother found them again later on after going thru our clothes that we didn't wear to donate them, I hid them under a bunch of old clothes thinking she wouldn't find them for a bit. I was wrong again. She didn't say anything to me at first, but when I went looking for them I confronted her about them. She did take them and we had a talk about it, but it still didn't go anywhere. Finally one year I went full in and told her that I liked wearing women's clothing and that I still did it, but never around her. I would only under dress when she was home, but she never knew.

What would you do if your son was into crossdressing?

If I have a son and he told me he crossdressed I would be proud of him and offer to take him shopping for his own clothing and tell him to be honest with himself about it and to never let anyone hold him back from him being who he wants to be.

[Lacey New]

When did you discover you liked crossdressing?
When I was in my early teens. I started to become curious about girls. Back then, girls wore blouses and skirts to school. I could see the bumps on their chests and the outlines of the bras and the skirts often provided a flash of panties. They looke inviting and exciting and I wanted so badly to know what was underneath. And the lingerie itself was exciting. The Sears and Pennys catalogs were my version of Playboy. One day after school, I was home alone and a pair of nylon panties was hanging out of the common laundry hamper. Well, I stripped down, put them on and I was hooked. I was ashamed at what I had done. I felt dirty and tha t I was a pervert and I vowed never to do it again. But the next day, I did it again. I had a lot of self doubt. I wondered if it made me gay although I never had any attraction to other males. Eventually, I had the opportunity to try on a bra with the panties and it was wonderful as well even though I still felt guilty and ashamed.
How did your family deal with your crossdressing?
I was a pretty sneaky kid. If they eve knew, they did not let on.
What would you do if your son was into crossdressing?
I would certainly permit it and I would help him acquire the various items that he needed. However, I would help him manage it. For the most part, I would insist that he keep it private and only crossdressing at home at least during his school years. Kids can be mean and even in this so called enlightened age, whether we like it or not, crossdressing is tolerated to a degree but not really considered ?normal?.. Once he is out on his own, he will have the opportunity and the responsibility to make his own way.

[PantyBoots]

I would impress how important it is to be honest and open with a potential spouse before marriage. Teach him that compromise is an important part of a marriage and that he can't always get what he wants.

On small issues, fine, but if crossdressing is a major part of your life, and a potential partner won't accept it, then they aren't the right person. Being happy is the most important thing, not if you are married or not.

[BLUE ORCHID]

I started 77 years ago and never had any Doubts about it,

[Robin777]

I started when I was 12 or 13 . It's been so long ago I can't exactly remember. I started by putting on my mother's bras and panties and slips . I was never caught doing it. It always made me wonder if my mom knew I was doing it and never said anything.

[Blonde617]

Started at 8 or 9. My parents discovered me wearing a bra and panties one night. And caught me again later.

Based on their reaction I assumed I must be gay and after not being happy dating some girls, kind of threw myself at some guy friends. That wasn't any more rewarding. It took a lot of reading and talking to a counselor to understand where I sat on the spectrum.

[Sakurai]

I started trying on my sisters things somewhere around 10-13 I'd say? Namely her one piece swimsuits I remember putting on a few dresses and even an old flannel nightgown she had (loved that one), her bras a couple times. I never really got the chance to dress up until I moved into a place of my own about 10 years ago.

My sister somehow knew I was wearing her things because I doubt she ever saw me but during an argument basicly outed me. My mom asked if it was true and I of course lied, she was not very understanding. My sister I think was more wanting to win the argument basicly because I DO remember talking to her about wearing the swimsuits, she even gave me an old one that was worn by a neighbors girl donated to her. It was green with crossing straps and worn in areas but fit me perfectly. We havnt spoken in a long time and I dont know if she knew I was still crossdressing. Mom never said a word and we were pretty close up until her death.

[mbmeen12]

https://www.crossdressers.com/forums/showthread.php?278842-when-did-we-start-crossdressing/page2

Here is more posts...

[Vikky]

My earliest memory is when I was a toddler. Mum would read to me as I sat on the floor and she would be wearing stockings and slip. I enjoyed the feel of them. I also recall watching her pull on stockings, smoothing them out and clipping them onto her suspender belt. Not sure why she let me do this, but it happened. I never tried any of her clothes.

Then during puberty the ?feelings? started and I would be flicking through ladies magazines taking in the fashions and, especially, the underwear. Corselettes seemed to be a fascination as did wedding dresses, the frills and underskirts.

These ?feelings? and interests continued throughout my life, thinking I was a wierdo I kept them to myself, even during a long marriage with two children.
Then came the internet. There are more people like me! Wow. My interest was rekindled and I started dressing and enjoyed it. I joined this forum (brilliant by the way) and Vikky came into being.

My wife tolerates it and I am able to sleep enfemme quite regularly in a separate bedroom, dress a couple of evenings each week for 2-3 hours. This week I can spend more time dressed for a few days while she is visiting relations.

I have never regretted getting hooked.

Vikky

[Alice92]

* When did you discover you liked crossdressing?
I have a twin sister and I have always been jealous of her cute dresses. I had to start trying them in secret when I was 6 years old.

* How did your family deal with your crossdressing?
No one in my homophobic and transphobic family knows my secret.

* What would you do if your son was into crossdressing?
I will obviously support him while being a little worried knowing the psychological problems that this can cause. But I would be happy to talk about fashion with him and buy him some clothes.

[Georgina]

I started when I was about six years old. That was in the late fifties and I became fascinated with petticoats and stockings. I wore a lot of my mother's clothes but nothing was ever said. I would be supportive to a son that started crossdressing.