What made you crossdress for the first time?

[Laura912]

It...just...happened...65 years ago.

[joank]

My sister and I were playing on a cold northern Illinois night. Mom was in the other bedroom. Sis dressed me in a button back dress of hers, other garmets, from head to toe including penny loafers and took me in to see Mom. I was complimented on the look and it has been dressing ever since.

[AlisonRenee]

Just opportunity. My older sister's swimsuit (pale yellow with a floral print and lots of ruching) was left in the bathroom. I was 4. Loved it from that moment.

[diannecourtney]

CDrs' One never knows where a virus attacks, but I sure am happy I got infected. This lady knows where and how the whole thing slide down the mountain and the bra and skirt I am in at this time is just right for me.

[Dani Alana Taylor]

After reading all the responses I think I will expand mine. I remember before preschool even when my best friend (still is) came over quite a but. Our dads were best friends growing up and we have real close birthdays and same age lol. Anyway when she came over we played dress up games and for some reason I always dressed up as a girl. I remember one time my "excuse" in the game was we were at an all woman's airport haha! We had a curly wig to I would also wear. My family knows about that and makes fun of me (all in fun) to this day. my friend doesn't bring it up ever though. Dont even know if she remembers it, but we hve pictures.... Damn photo albums! Lol But as for dressing now no one knows and right now that is just fine for me.

[Helen Grandeis]

Seventh grade it was if the girdle and stockings were calling me. I put them on and they imprinted on me. I didn't actually go fully dress and "go-out" until a year ago.

[Debglam]

What made you crossdress for the first time?

Dani, I was born this way!

[cindi cinnamon]

Although I had two sisters (one, two years older, the other, one year younger), i never remember trying on their things. However, as early as I can remember, I did make the best of my own undies. I would often roll down the elastic (as tightly as I could) to produce a low rise bikini out of them. I just as often would tuck my penis between my legs and admire how much I looked like a girl.

That was the extent of my childhood experimentation. But after I graduated from high school, the first thing I bought for myself were some jockey brand bikini's for men. I was quite pleased how they made my butt look so cute. Nothing other than that happened for the next 20 years.

Then, when I was getting ready to celebrate my 40th birthday, I went out and purchased some satin string bikini's for my wife to wear, so we could spice up the birthday celebration just a little. She tried them on, but didn't like the way she looked in them, so she declined the invitation to wear them (kinda broke my heart). Anyway....... I went to take a shower later that evening, and when I got out to dry myself off, I noticed they were lying on the vanity. The urge hit me like a ton of bricks, and I tried them on. They fit perfectly!!! So, without thinking, I pranced down the hallway, and peeked into the living room, where I found my wife watching TV. With a little bit of shyness, I stepped into the living room and modeled the panties for her. The first thing out of her mouth, was how cute she thought I looked in them, and proceeded to chase me down the hall and into the bedroom. What happened next was nothing short of amazing, but it's nothing I should talk about with others.

Sooooooo...... That was the day I was officially hooked, and have not looked back since. I now have two drawers full of the cutest panties you'll ever see, and have expanded my interest into full dressing. I think I have more girl clothes than I do boys.

I have to believe, however, that from my earliest experiences, I was more interested in how I would look as a female, than any particular interest in the clothing itself. So, now I'm searching and exploring the possibility that I might be transgendered. The thought doesn't scare me, and somehow feels "right".

All this, from just rolling down the elastic on your undies????? It doesn't seem possible....... BUT HERE I AM.

[Brittany CD]

I just wanted to put on a bra one day and then it evolved from that to dressing up as a girl

[Miss Brianna]

For me it was the soft and shiny appeal of my mom's lavender unitard. I loved staying home from school or getting home before her so that I could slip into it. She must have known, but never said anything. This was in 1988 in the midst of the spandex phenomena.

[Pinky188]

My sister wore really cool clothes when I was a young kid and I always wanted to try them on. So one day I did! Loved it!!! From that point on I was always sneaking in and wearing her things! We are the same size so it worked out great! One day she caught on and asked if she could make me up! My dad was sooo pissed!! Ha! Oh well! Now she borrows my clothes! Dammit!!! I guess I owe her!!!

[Diane Smith]

It started with my mom. She mostly wore capris, Keds and tees around the house, but at least every couple of weeks she had an evening out with her bridge club or some other fancy social event. Fashionable dress was called for, and as they say, she "cleaned up real good." The transformation was amazing -- it was as if she became a different person in her heels, dresses, jewelry and (in season) furs. Even her smell was different. This made a huge impression on me when I was two or three years old and watched her dress and leave the house for adventures I could only fantasize about, and I think I developed a lifelong obsession with the ability of women's wear to completely transform one's look and demeanor. I was an only child, so I only had access to my mom's stuff and occasionally my grandmother's. And it was a few years later before I was physically able to sneak away to her drawers and closets, or even manipulate the fasteners on the clothes and so on. There was never a time when her clothes fit me very well, but that didn't slow me down much.

Mom never directly acknowledged that she knew I had been playing in her room, but I think she must have been fully aware of it and indirectly encouraged me to some extent. She would occasionally put lipstick and nail polish on me, let me get my ears pierced when I was nine, and bought me my first pair of grownup heels when I was 12.

- Diane

[SarahStar7]

I honestly don't remember what made me do it. All I can remember was it all began before I started kindergarten. I wasn't able to fit into my mom's clothes so I had to improvise by turning my own tshirts into a skirts, and wear my mom's pantyhose that would just fall off me. :P

[Michala]

Don't remember how old I was, probably about 9 or 10 and wanted to see what it was like to wear a bra. Tried my mom's and it fit nicely. That led to nylons with a garter, then a slip and a dress. Eventually tried makeup which was awful but it was a start. Days when I was home alone were spent experimenting. Mom never said anything but when I think back, like alot of us, how could she have not known that someone had been in her drawers and closet. Impossible to get everything back the way it was.

[eternal-c]

I have only done so a very few times, but I remember as a kid I always loved the way Mom looked and I would often help her with hair and such. (I think she liked me helping just so I wouldn't get in trouble elsewhere.... but who knows now ) The only thing I wore consistently (and openly) was a flannel plaid long night shirt that used to be mom's before she passed away. It was more unisex than anything, but I remember that I would wear it almost every night for a few years... It came down to a few inches below my knees and was great especially in the winter.

[Wallaone]

I was a little younger than ten. My cousin and her best friend were supposed to look after me while our parents were away for the weekend. My cousin's best friend brought a long her young sister (two years older than me). I was an only child and never really saw girls underwear before. Anyway, one morning, she was in the shower,I saw her clothes in a neat pile next to her bed. We shared the same room, but had different beds... She came out of the shower and noticed me snooping through her stuff. She told me to put her underwear on and wear them all day or she would tell me dad.

I complied. The rest is history.

[Sarah Doepner]

What made me crossdress for the first time? It was the guy in the mask, the brim of his hat pulled down and the gun in his hand telling me if I didn't put on the girl clothes he'd shoot me. He came back, every time I had access to a closet full of womens things.

Okay, it wasn't that, but whatever it was I found it very compelling. I was curious, but then I was curious about cars and guns and other thing I never tried before it was allowed. Maybe I wasn't all that happy being a boy and thought being a girl may offer a better life. Maybe that would have been better, but being a part time girl isn't a good life plan, not when everone around you thinks its worse than odd. If there had been easy access to psychologists when I was first found out by my parents, maybe I could have worked through the memories and feelings while they were still fresh. Now they are 50 years in the past and could be as much fiction as actual memory. So I don't know and I can't see a way to bring that situation back with enough clarity to properly answer your question. I kind of wish I had a nice rock solid explaination that I could pull out and examine from time to time. It may not make things better, but there would be a lot less confusion.

[Misti]

I bet a lot of people are probably the same as me when I say I don't know why but I'm wondering...?!

Dani, I honestly am still wondering why myself? Not questioning it, just wondering, that's all, about this mysterious, marvelous "thing" that has happened to me so late in life...

Someday I'll find out, but by then it won't make any difference, "The die is already cast!" (double entendre intended)

[steph9]

Yeah me too..... started when I was really young.... and I was always curious about it... wished I was a girl

[Katelyn B]

I really don't remember, I was around 6 or 8, and I remember having time alone to myself in the house, which at that age looking back is a little strange to be left alone, can't remember the circumstances which lead to it, guess my parents thought I was responsible enough to be left alone. For a while prior to discovering something which made me feel happier I used to not wear any cloths during that time alone, since I remember not liking what I was given to wear (nothing out of the normal for a boy, I just didn't like it).

Anyway, something must have made me go into my sisters room and put on her cloths, because at some point I did, I would then spend every opportunity (until differing growth rates meant they no longer fit at all) dressing in her cloths. What that was though is a mystery, I wasn't particularly self aware as a child, I didn't know or couldn't articulate to myself that I wanted to be a girl, but I did know that wearing her cloths and being a girl (in my eyes) made me feel as whole lot happier then I was when I was a boy.

[Katelyn B]

I really don't remember, I was around 6 or 8, and I remember having time alone to myself in the house, which at that age looking back is a little strange to be left alone, can't remember the circumstances which lead to it, guess my parents thought I was responsible enough to be left alone. For a while prior to discovering something which made me feel happier I used to not wear any cloths during that time alone, since I remember not liking what I was given to wear (nothing out of the normal for a boy, I just didn't like it).

Anyway, something must have made me go into my sisters room and put on her cloths, because at some point I did, I would then spend every opportunity (until differing growth rates meant they no longer fit at all) dressing in her cloths. What that was though is a mystery, I wasn't particularly self aware as a child, I didn't know or couldn't articulate to myself that I wanted to be a girl, but I did know that wearing her cloths and being a girl (in my eyes) made me feel as whole lot happier then I was when I was a boy.

[Piora]

This is a really great thread....some excellent and entertaining responses....I enjoyed reading through them all.

What made me dress for the first time? Well, I was about 14 and went on vacation back to my country of birth. My parents and I were going to be spending time with both sets of grandparents who lived in different cities. To make things more accommodating, my mother went off by herself to visit with her parents, while my dad and I stayed with his. The first night there was not good, as my father snored and we were both sleeping in the same room. There was no other bedrooms, so my grandmother arranged for me to spend the next few nights with a neighbour and friend. She was widowed, and her 23 year old daughter had just moved out. Well, I was given the daughter's bedroom to sleep in. The next morning, I woke up and the neighbour had gone off to work, so I didn't go back to my grandmother's immediately. Instead I got to snooping in the dresser drawers and found tons of bras, panties, stockings and garter belts! The daughter must have eloped and left all her stuff! lol!!

Anyway, an incredible urge to wear these things overwhelmed me, and I tried on everything in sight! It's all a hazy memory now, but for the next few days, while staying at the neighbour's house, I dressed up in the mornings before going over to my grandmother's. I do recall the euphoria I had while dressed in those things.

Strangely enough, I think I repressed the urge to crossdress until I reached the age of of 30, as I never had another experience, or had any access to women's clothing. If I had, I would no doubt have started at a much younger age.

I started for real when I was shopping one day for my former wife. I wanted to buy her something sexy for Valentine's day. As I was looking in the women's section, a mannequin with a beautiful red corset, black panties and black stockings caught my eye. I knew my wife would never wear anything like that, and completely dismissed it at first. Then I thought with a thrill of discovery...."But I would!" So, I bought a satin pajama set for her....and the corset, panties and stockings for me!! Since that day, it's been one hell of a ride!

[Lisa LIckorice]

I remember seeing my mother and aunts in pantyhose when I was about 5 and thought it was the greatest thing. I loved the way they would shine in the sunlight. My younger cousin would always get special attention because he liked to wear high heels. I was a little jealous of that so.....

Fast forward to when I was about 8 or 9 and I remember the first time I put on my grandmothers pantyhose, nightgown, and panties. My grandmother had a huge home and I would go there after school. I had the house to myself for about three hours every afternoon. I'd sit under a blanket dressed in her undergarments watching The Brady Bunch on Nickolodean and Primetime Wrestling on USA Network. I always felt (and still do) at ease when I put on the silky pantyhose and underwear.

[Cheryl J]

I cannot recall making a decision to dress up, I just did from a very early age! I wore a pair of mum's summer sandals around the house ( they were way too big but made a glorious clicking sound), for no other reason than it was fun. When mum finished the washing and ironing she put our things on the bed for us to put away. One day there was a pair of satin, lacey pyjamas amongst my jocks. I don't know why they were there but I wore them to bed anyway. Over the years I would take some of mum's underwear and nighties from the clean washing and wear them discretely. Mum never said anything, to me anyway and when I'd finished wearing various items I'd put them in the wash. This went on for years with nobody saying anything. I didn't know how to raise the subject of wanting to dress up and mum never mentioned her vanishing/reappearing items. Life went on. My sisters and father never seemed to know a difference with me and I grew up.
Here I am 50+ years later typing on the computer made up, wearing a blue floral blouse and black skirt and 2" heels. My wardrobe has only women's clothes with a very small emergency stock of men's underwear.

Mum's no longer with us but our realtionship was always happy and friendly. I just wish I could have raised my dressing up with her. I fancy that she would have been very accepting and helpful.

[Beverley Sims]

I found a bra in the street and picked it up and then took it home. I was eight.
Answer the question.
"Curiosity".