Crossdressing in teenage: discoveries, doubts and insecurities

[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...dressing/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.