At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

[nicoleazcd]

Around the age of five. I got caught my my parents wearing my sisters clothes. They decided i should wear them to school the next day. I used to dress up with my sisters clothes alot when we were left without a babysitterprobably about the age of 10. I then would put on a very appealing sun dress of my moms. Her heels were to big for me but i was determined to wear them and made it work. Have been dressing since then .

[JenniferR771]

I was fascinated and starred and starred--a boy at a school carnival had been dressed up as a sexy fortune-telling gypsy, when i was age about 9. (No insult intended to real gypsies.)

Again about age 12 on Halloween school party day. A classmate Peter (whose mother was a beautician) dressed him up beautifully as a woman, black dress, wig, heels, purse. We all thought he was a substitute teacher. I was so interested, i couldn't take my eyes off him. Jealous, yet to scarred to try any women's clothes myself--until a year later in the privacy of my mother's room.

[MelindaC]

At age 11, when I first actually began wearing on a regular basis. That was when I felt the need to try on mom's girdle and stockings. Once I had them on, I was completely hooked. Things just progressed on from there. And I still love wearing a girdle and stockings, and don't feel properly dressed without them.

The need to dress actually started much earlier, probably about 6 or 7. On at least one occasion for Halloween, I was dressed as a frumpy old maid, wearing a dress and heels --- and I liked it. When we kids got dragged along on shopping expeditions, even at that young age I found myself very interested in the lingerie department, and especially the girdle counters, which held a particular fascination for me.

Even into college age, I was often pressed into service by mom to put on a dress or skirt she was making so it could be hemmed. How I enjoyed that!! Must be why I feel so comfortable wearing a dress...

It wasn't until I was on my own in my 20's that I was able to start buying my own things --- mostly by just going to the department stores and buying them.

[Leglover2k8]

For me, It was around the age of 9. "borrowing" my sisters ballet clothes and costumes was the start. After that i was especially hooked on tights. I was always checking to see if she had thrown any out. It just made me feel better to be wearing the "other genders" clothes. I then made choices in my life both to oppress this feeling (over compensate) and to embrace, and find ways of wearing in more socially acceptable ways. ie: cycling just to wear the spandex. It got my body into pretty good shape, and i just loved feeling the wind over the spandex.

I guess thats where i first wore the clothes, but it was always percolating under the surface.

Hugs
-Sera

[Michelle04240]

I put on panties for the first time at about age 10 and kept a stash in the bathroom under a cabinet. (probably still there lol) Put on my first full outfit at about age 15, full make-up at 28 (though I had dabbled before), my wig and breastforms came at 33.

[TeriAnn]

I started out by putting on my mothers heels, I was about 5 or 6 when I did this. As I got a little older I would ride my bike to the local store and I "borrowed" a pair of sandels. This was the being of my life as a crossdresser I realized I should have been a girl when I was 12. I got to stay at my neighbors house when I was sick. The neighbor had a sixteen year old daughter and needless to say since she was not there I really got into clothes. I even borrowed a pair of wedge heel pumps. Bet she never figured out where they went. Since then I have pulled together an extensive collection of clothes underwear heels and anything to do with being a female. I wish I could have had SRS but I didn't I regret it now. Alas it wasn't meant to be. Oh well I will always enjoy what I can do until it is my time to leave this earth.

[Andi]

I hope this story isn’t too long or boring but I think it illustrates many of the quirks of fate that can befall a crossdresser. Maybe it’s very familiar to the rest of you and I just think it’s unique to me.

When I was 8 years old I had my first encounter with dressing. I found a box of my aunts clothes stored in our shed. When I opened it there was a pair of white high-heeled sandals starring at me. I don’t know why but I just had to try them on. A year later my mom tried to get me to dress as a girl for a Halloween party but I adamantly refused due to all kinds of fears including the fear that I might like it. Over the next several years I didn’t try to dress and didn’t think about it either. At the age of 12 I began to be interested and intrigued again by women’s clothes. One day when my folks went shopping I explored my mom’s things and put on a bra, panties, skirt, sweater and her red high heels. A rush came over me and I felt delightfully lightheaded. As I lay on the bed looking at my “breasts” I suddenly and thoroughly wet my panties. This was the first time I had had that experience and it felt so wonderful. Needless to say I looked for every opportunity after that to pretend and get that special feeling again.

When I went off to college the dressing ceased because I lived with a roommate in a dorm. I got married in my junior year to a sweet, attractive woman who liked to wear dresses and high heels. After two years of dating we decided to marry. She had no clue about the other me. We moved her things into an apartment the week before the wedding and I couldn’t resist sampling. Imagine my surprise to find that many of her things fit perfectly. After the wedding, I didn’t dress again thinking it was the right thing to do, as I was finishing school while she worked to support us. One night we were talking and playing around and out of the blue she said, “I wonder what you would look like as a girl?” I played coy and slightly uncooperative while inside me my heart was racing a mile a minute. Finally I let her have her way and she went to work – panties, bra (filled with grapefruits), stockings, slip, skirt, sweater, makeup, jewelry, and of course high heels! I was so excited I thought I would pass out. After an hour or two we had to undo everything and return to “normal” whatever that was at this point. A few nights later as I was feverishly studying I commented how calming being dressed was and how I was much more able to concentrate on the school material. To my surprise she let me dress myself in her things again and this began a regular occurrence. As they say once the genie is out of the bottle how do you get him/her back in? As time went on she began to buy me things on her own, makeup, dresses, shoes and even a wig. One night as we were leaving for the show she asked if she could borrow a pair of MY heels. I wasn’t dressed but I was so flattered and proud to be her girlfriend. Even though I never went out of the apartment as a girl, I was having a ball and since she was shopping with me and alone for me I thought she was very supportive. Wrong!

After I graduated I got a very good job with a fortune 500 top ten company. The dressing time quickly came to virtual standstill due to my wife’s sudden change in attitude about dressing at home and I didn’t want to jeopardize my career by doing it somewhere else. I managed a few evenings alone in the spare bedroom but when my wife became pregnant with our first child she said the dressing had to stop, the stuff I owned had to be purged and she didn’t ever want my femme self in her life again. I was in a real bad way; caught between my love for her, my new responsibilities of provider/father to be and the other self I so much wanted to be. There really wasn’t a selfish choice to be made so I did as she said and bottled my desires/feelings deep inside. Forty years later, with only a few isolated ventures to the femme side, the kids have all left home and I am now retired. I have more alone time now and since I don’t have to get up early each day for work my time to be me is late at night when my wife is asleep. I have procured a small stash again– 1 set of undies, one skirt, one top, a little makeup, clip-on earrings and 2 pair of 4” heels. I don’t think she suspects and she is still dead set against crossdressing yet ironically she is openly supportive of gay and transgender rights.

Don’t get me wrong by the tone of this story. My situation is not my wife’s fault. She’s a wonderful woman in all regards and I’m very lucky to have found her. I made the choices along the way on my own. Although I have lived with those choices all these years, I can’t help but feel like I’ve missed out on something. I’m glad I discovered this forum and I appreciate the company the girls here afford each other. It means a lot to a “girl” like me to know I am not the only one who struggled and is struggling with these feelings.

Was this too much information?

[SandyR]

12, tried on my moms pantyhoses.......Been hooked ever since.

SandyR

[brenya]

as posted in another thread, around 6 when I would play in my mom and sisters clothes, I also stole some of my sisters barbies and played with them in the wee hours after bedtime

[Stormgirl]

Around when I was about 8 years old

[Cindyloo]

My first crossdressing experience was when I was around 13 or 14. I wanted to be a girl for halloween. Told my sister and she dressed me up with some of her clothes. She had me wear a pair of her panties, jeans, trainer bra and white top. At that time I had long blond hair so I did not need a wig. She applied a little makeup to my face, lip gloss and I was ready to go. I felt like a princess that night. Went out in public with my sister to go trick or treating. Some of the neighbors recognized me but said I looked pretty.

That is when I should have continued my crossdressing but I did not.

Cindy

[chrissietoo]

My first clear memory was at ten, when I also asked to be a girl for Halloween. I'm sure I was dressing before then, but I don't remember. My mom was great, and went to the thrift store and put together a lovely outfit, complete with curls and a handbag. I felt absolutely wonderful! Some of the other kids teased me during the school parade, and my mom has a great picture of me bashing one of them with my handbag! (not very lady-like, but effective).

Around that time, also, a buddy and I would raid his mom's lingerie drawer and dress for each other, something that was very exciting for both of us, expecially since we had just discovered the pleasures of masturbation!!

One of my best friends was a tomboy who would visit her granny in our neighborhood every summer. Over the years, we had explored our bodies together, and I had been excited to wear her panties, which she freely gave me (not particularly caring).

One summer she suddenly appeared with budding breasts and a bra to hold them. This quickly started another wave of exploration and clothes swapping, but now very much in secret. She coveted my baseball uniform as much as I did her bra! and crazy us, she would stuff panties in the crotch to make a bulge, as I would her bra. She was very boyish and cute, and grew up to have many beautiful girlfriends.

The feeling, and the "permission" stayed with me, and I always shared clothes a little or a lot with my gf's--I'm so comfortable (and much sweeter) as Chrissie, they have usually been happy to share.

xoxo chrissie

[LindaTS]

I think it was when I was about 6, maybe 7 years old, or so my mom told me. I have a very clear memory of the episode and it was great moment in my life.

[joperinal]

I think I was 7 or 8

[gennee]

Two years ago at age fifty-six.

Gennee

[Denielleinheels]

I started at 9 stopped at 21 started at 27 stopped at 31 started at 35 and ain't stoppind again. It is me and that's who I am

[Sandra H]

I knew from around the age of 5 or 6 that I should have been a girl. I started wearing my mums underwear, panties, stockings etc. When I was about 10 my granny had a friends girl staying with her for a week and she would be about 16 and when she went home I found a bag of silky panties in a cupboard. I went to look, touch, feel and wear them as often as I could.

I would be 15 years old when I brought my first pair of panties and pantyhose and hide them in my bedroom and wore them 2 or 3 times a week. Then when I left home and got married I told my wife who helped me with my cloths so I started wearing panties, pantyhose or stockings everyday. I also dressed fully in the evening and wore a nightdress every night. My wife and I would wear each others panties, pantyhose, stockings and nightdresses. Sadly, my wife died in April 2004, I now wear most of her cloths now and it has made me feel better over my lose.

I am sat here tonight wearing one of her bras, top and skirt. NICE.!!!!

[Ruth]

I can recall being fascinated by my mother's underclothes at a very early age - probably 4 or 5. Then I constantly wanted to wear girls clothes but got absolutely no opportunity. I had no sisters for a start. Then in my teens, 12 or 13 I would think, my mother got a full time job so I usually had the house to myself after I got home from school until she got in. And in that time I would try on her clothes.
The story from there on is a long one, but you only asked about when we started...

[Summer314]

I agree it is an important question. Had no idea I was such a late bloomer at 13 when I found my older cousins bikini in the bathroom where she'd changed. Almost 40 years ago and see it clear as crystal. Blue & white flower pattern, 'S' hook on top and still damp from when she took it off. It was wonderful and I loved it.
Gee, do you think that was a turning point for me?

[Missy]

It was with the Boy next door role playing games when we were alone him male me female and this was around when I was about 7 or 8 years old still in first grade. later I just kept on wearing panties and bras when ever I could

Missy

[LisaCMW]

I started out when I was around 13 or 14, can't really remember why... I felt ashamed until recently I admitted my crossdressing to a therapist, who encouraged me. My first time out will be June 6th though, road trip from CT to NC shopping along the way...Yay!

[Katie-Jayne]

I think I was 8 or 9 when I dressed for the first time and subsequently got caught by my parents (Doh!). Didn't put me off though and I used to get left round my nan's when my mum and her went shopping. So of course I went investigating in her wardrobe. She had some fantastic shoes. It was such a shame when my feet got too big to fit them.

[raelene]

I started at the ripe old age of seven when I wore my sisters bras and panties, she was seventeen at that time. Ive been dressing since and wear everything femme even tampons. I dont try to pass just love to dress. My favorite items to wear are ruffled panties and sissy dresses, but I also like baby doll nighties, bras, skirts, blouses, dresses, and of course I wear panties 24/7. When im not in panties I wear diapers and baby plastic pants, I can thank my girl friend for that as she got me into wearing them as she wears them herself and even under her dresses many times at work.
Raelene

[chrissietoo]

I’m glad I discovered this forum and I appreciate the company the girls here afford each other. It means a lot to a “girl” like me to know I am not the only one who struggled and is struggling with these feelings.

Was this too much information?

Thanks for telling your story, it's wonderful, and I can relate to so much of it!!

xoxo chrissie

[Misty_cder]

I first fell in love with my mothers nylons at the age of 14. She would hang them in my bathroom to dry. The bathroom was next to the washer and dryer. Every now and then she would have a pair of white tights that were my favorite.