When did you first crossdress?

[cd_dominique]

I don't remember my age, but I was fascinated by my mom's and sister's underwear drawers. When I knew they'd be out for a while, I'd sneak into a drawer and put on a bra just to see what it was like.

One night when both were out, i had gone into my sister's closet and put on just pantyhose and a dress (wearing men's underwear) and was checking myself out in the mirror. Unfortunately, the phone rang and my little brother, whom I was babysitting, answered the phone as I tried to run down to get it first. He saw me dressed as i was and actually said into the phone "You'd better get home, there's something weird going on", referring to me.

[Angela Marie]

Not sure how you define crossdress. I began wearing my moms tights when i was 11 or 12. Loved the feeling and to this day I love tights and pantyhose. I'm also a runner so when running tights became popular I wore them even more. It wasn't until my late 40's early 50' that i began dressing more fully. I was terrible at makeup. I had my first makeover when i was about 52 or 53 and looked awesome. A bell went off in my head and i've been dressing ever since.

[Kristie23]

I was 16 and house sitting for my girlfriend as her family was overseas. I'd always liked her gstrings so started by trying one of them, then I had to see how it looked under every piece of clothing of course.

Next thing I know I'm wearing a pair of her sisters heels and dressed up in a ****ty mini skirt and nice top.

[Brandy]

When I was little, I played with my mom's slips and loved how they felt. Eventually, my parents said I couldn't do it anymore and took them away and I forgot about it until puberty (13ish) when those memories came rushing back suddenly, and I felt a great urge to try things on again. I then started wearing my mom's panties, girdles, slips, and night gowns when I was home alone and have been doing (now with my own collection) for 20 years.

[kryss.cd]

I was 14 and moved into my sister's house. There was a drawer full of her old lingerie in my room that I explored. I tried everything on and didn't touch anything again until I was 16 and my girlfriend at the time dressed me in her lingerie. I've been underdressing on and off since then.

[Teressa]

I must have been 8 or 10. Saw one of my mom's full slips hanging on the closet door and something told me to try it on. OMG I couldn't stay out of her closet from then on. Still have a thing for full slips.

[Karen RHT]

I was 11 with Halloween coming up. We had moved into another house recently, and a lot of stuff was still in boxes. I always enjoyed Halloween (still do) and always wanted "something different" for a costume. My mom knew how much I enjoyed Halloween, and frequently used her sewing talents to help make my costume a reality. We were going through boxes when I came across one with some of her things in it. Looking at them, the thought of dressing completely as a woman entered my mind. Told mom that's what I wanted to do. She thought about it for a moment, said it would take some work if I really wanted to pull it off, and asked me if I was sure I wanted to put in all that effort. Without hesitation I said yes, which started me down the crossdressing road.


Karen

[Sandie70]

I don't know if this counts, but my mom really wanted a girl. So, she let my hair grow out and dressed me in girl clothes up until I was six years old.

From the pictures of me in little, frilly dresses with ribbons and bows in my hair, I was really cute. Prettier than my GG cousins.

Guess all that was quite prophetic. When I look at those pictures I regret that mom didn't let me remain a girl. But in those days, that would not have been acceptable.

Sigh.

[Marie-Claude, France]

I was 11 or 12 and I was playing with my cousins; since we were all boys I declared that I would be a woman and I dressed with some of my mother's clothes. The rest is history.

[charlenemichaels]

My 1st CD expeience was around 9 years old when i went to the bathroom and saw my grandmas silk stockings drying on a rack.
They were dry so i carefully removed my boy stuff and pranced in the BR with them.
Instant attraction, instant lightning! Only trouble was i forgot to lock the door and got caught.
Grandma made no big deal of it and never told my folks.

She gently admonished me to leave her things along.


~Charlene

[Piora]

I was 14 and moved into my sister's house. There was a drawer full of her old lingerie in my room that I explored. I tried everything on and didn't touch anything again until I was 16 and my girlfriend at the time dressed me in her lingerie. I've been underdressing on and off since then.

Kryss, I had a similar experience to yours. When I was about 15, my parents and I were staying with relatives while vacationing in the UK. A neighbour of my grandmother offered to provide me accommodations, as there wasn't really enough room for us all at my grandmother's. It was her daughter's room, and she had just got married, and moved out. She had not yet picked up any of her things that were in the dresser. As my grandmother's neighbour was a widow and worked during the day, I found myself exploring the contents of the dresser. This was in the mid-sixties, so it was all stockings and garter belts. The only colour was white back then, also. Anyway, I dressed in stockings, garter belt, bra, panties and slip. There were some shoes, but far too small for my feet. I spent many a morning looking at myself in the full-length mirror. I was very sad when we left for home.

Oddly enough, and believe it or not, I never pursued dressing again until I was married, and in my early thirties. Since then, I've had the occasional hiatus, but I always had the desire come back. When it does, I indulge even more than the time before!

[Heelios]

My first CDing experience was trying on my friends mums heels which she kept in the porch at the front of the house. I used to deliver the local newspaper there when I was about 14 or 15 and one time I was there and they were out so I took a pair off the shelf and forced my feet into them - they were way too small but it felt amazing!! The CDing thing has slowly crept up my body from feet ever since!

[Michelle_Diane]

I was about 9 or 10 and my mum had some tights hanging up to dry. I tried on a pair and loved the silky feel and how they encased my toes. It just grew from then on.

[Wandacdmn]

I was 16 years old. I matured very late so I was a smooth boy. I tried on my mom's "hot pants" and I was totally smitten with crossdresser desire...

[StefaniLara]

I have a vague memory of wearing my mother's dress when I was around four years old, then immediately being chastised for it. I conformed to societal expectations until I hit puberty when I started to dress in private. It wasn't until college that I started to experiment.

[Cynthia T]

1961. I was 11. Had no interest in girl clothes. Then, one evening home alone, I was reading a book that mentioned in passing a woman in high heels. I was immediately turned on, went and got a pair of my older sister's heels and put them on. Scrounged in alleys for more women's clothes, until I was old enough to buy.

[Lilblondecutie1407]

I knew I had a fem side around 5. By kindergarten I already envied the cloths the girls got to wear. Although I can fit in with the guys, I seem to gravitate towards the girls. I seem to feel more comfortable in a group of girls. Once I have been there for a short time they seem to accept me as one of them in our conversations.

i had a very similar experience but did not start dressing with a better understanding of who I was until I was 18-19 ish and started really dating, but once I started it was full steam ahead.

[Li'l Miss]

I don't know what age I was, but it was definitely pre-school. I put on a pair of my mother's panties and walked around the house in them. When she saw me, she laughed hysterically and said her panties were way too big for me. My desire to dress in women's underwear lay dormant for quite a while after that, then came back full throttle about the time of puberty. I raided my mother's lingerie drawer every chance I got until she caught me one day posing in front of the mirror in her bra and panties. She scolded me for what crossdressing might lead to, but bought me a package of white nylon briefs for my own. I've been addicted ever since.

[ChubbyLeahCD]

Not sure when but when I was in kindergarten, I went to a school that was small and ran by a few people my mom knew.
The owner was brunette, tanned skin, sweet with cute feet. How do I remember her get? She wore sandals that I remember liking and she used to stand in a girly way and I remember copying her discretely.
That same school offered ballet for the girls and I wanted to do it to be with them and to have tight ballet clothes, even if they were male clothes.
Then I remember spending the night at my grandma's house and seeing her panties drying in the shower and always putting them on...
Fast forward to puberty, with my parents letting me stay at home alone more often, I started digging my mom's clothes from the dirty laundry basket and wearing it. I know it sounds disgusting but the excitement was such that I knew it was safe to let my juices so to speak, get the dirty panties dirty.
Clearly remember when I was around 12, trying on my mom's teddies and remember putting on her silk rumper pajamas and her flip flops.
Then in late middle school I stated going for her closet. Tried dresses, pants, bathing suits, shoes, everything.
Almost got caught one time: she came home and I had locked the door to the garage. She had an opener but no keys. She knocked but I was way too caught up in Leah's world.
She called the house and when I picked up she was yelling for me to open the door...and here j was in her lingerie.
I scrambled to put it all away and when I opened the door she was asking what was I doing in her room because we had a control panel for our alarm in the garage and she could see the zones I was in.
I don't remember what excuse I gave her but she never brought it up. All that continued and then I thought being a CD was too weird and I buried until. Then as a junior in college I bought used outfits and lingerie from an amateur actress called PussyCat on SouthernCharms.com and I used to dress up in my room in my apartment.
Lost all that when an ex girlfriend who liked me CDing threatened to out me to everyone when we broke up so out of fear I tossed it all away...
Then bought more stuff from her and still have it today. As of today I wear my stuff, and my wife's that fits me still and have bought a few things myself, cheap so she won't suspect the money leaving the bank.

Sorry I gave more than what the topic asked for but I just caught myself walking through my entire timeline as Leah and couldn't stop.

[Kimberly Adams]

I was 6 or 7 yrs old. I remember trying on my moms bras, way to big but oh well it seemed ok. I also remember around the same time cutting the bottom half of a t-shirt off and putting it on like a skirt with a belt. So fascinating this starts at such a young age.. I can still remember the exhilaration.

[franlee]

My 16th birthday, I conned or got conned on a made up bet to get out of my clothes and my Girlfriend out of hers. It worked to well, we did a complete swap from the skin out. And I was smitten-ed from then on.

[Glendy]

I think I was around 12 years old I used to see my sisters wearing their sex night gowns.

[Belle Cri]

I was raised in Europe, specifically in Italy, and there it was quite common for young children to wear some form of, well not a frock really, but sort of a dress. So, pretty much before I ever got out of diapers. What a surprise LOL.

[rachey77]

It was probably down to my sister actually!!! she dressed me up in her yellow party dress, I thought to myself; this is so much nicer than pants!!

[Alice_2014_B]

First time trying on a single item, that being high heels, I must've been around seven.
First time fully en femme was just about a year and half ago, early 2014.