When did you first crossdress?

[CherylFlint]

Same with me, somewhere around 4.

[NANNETTE]

I was twelve years old. It was my first year in high school and I was so envious of the girls in my class. At the time it was the fashion for girls in school to wear tights under their school socks. Oh I how I wanted to be like them, it was frustrating beyond belief. At the end of 1972, I wondered if my Mums tights would fit me, to my surprise they did. At first I wore tights under my football shorts, I imagined they were hot pants. It was the era of the go go boots and and tan tights. I saw a picture in a Pop music Christmas annual of the lead singer of Middle Of The Road in boots, I so wanted to be like her. Eventually I started trying on my Mother's skirts when my parents were out, a lovely experience I felt so much like the girl I always wanted to be. I wore my Mother's things for eleven years before I plucked up the courage to buy my own tights in Woolworths in 1981. Once I gained confidence I would buy dozens of pairs of tights in department stores.

I think the boys in my school knew I was different from them they used to tease me and call me a girl, I used to pretend to be annoyed but secretly I liked it. One boy said I shouldn't be wearing boys clothes in the gymnasium and I ought to be with the girls wearing leotards. I was thinking the other day that it secretly excited me, I so much wanted to be a girl. I opted out of subjects like Woodworl and Metalwork in favour of short hand and typing. One boy said I went to the girls typing classes because I wanted to be a secretary with a mini skirt who would bend down to show their legs to the boys, he was only joking but it really was what I would have loved to happen.

[Michelle V]

I must have been younger than four, I remember it because it was way before my parents divorced, my female cousin who is my age came to my house to visit and left her very pretty jacket in my room, I snuck upstairs to was it an was caught by an older cousin, I was very embarrassed and it left an impression on me, however, I've never stopped. Much as I tried I've never stopped, I just wished I had come to terms with who I am when I was younger, this way I believe I would be in a bette place with my self.

[SaraNZ]

When staying at my grandmothers I use to want to put on a small purple dress she had (dont know whos it was, she only had boy grand kids at that point) I must have been around 5 I guess. Moved on to trying on mums dresses and boots (no sisters - I imagine I could have progressed quicker if that was the case ), even pushing her earrings through my lobes when I was about 13/14 after school...only for a minute or 2, they'd have to ok by the time mum got home haha.

[Jennifer in CO]

Somewhere around 5-6? possibly earlier but I don't remember it. As a very sickly child, if it were a real cold night out I was put to bed in my older sisters long flannel night gown that had full sleeves and a high-neck collar. A funny to this is there was a home movie I saw a long time ago. Sis and I come stumbling into the living room on Christmas morning, both of us in long white flannel (frilly) night gowns....movie suddenly stops. Next frame she's still dressed the same but I'm in a dark blue floor-length robe (also my sisters) but it wasn't "girly", just long (covering up the gown). I've seen many a picture of me from the early 60's in my sisters hand-me-downs (shorts, rompers, etc) playing in the back yard. Thinking about this, I'm not sure why my Mom was so upset when she picked me up from my cousins (when I was 10) after spending 3 weeks with them...all of it dressed as a girl?.?...hmmm

[DebbieL]

When I was 2, I made a "dress" out of a dry cleaner bag. Mom thought it was cute and even made a belt out of some of the plastic. Dad freaked out because he was afraid I would suffocate in the plastic.

When I was 4, me and some other girls put on a "Circus". They dressed me up in white tights and a leotard and I jumped off the garage roof into a pile of mattresses.

The first time I was fully dressed entirely in actual girls clothes I was 5. I was playing Barbies with 4 other girls and we were trading Barbie clothes. Then the girls started trading clothes with each other. One of the girls wanted to try on my clothes and the girls decided to dress me up. They had me change everything. I was wearing panties, tights, Mary Jane shoes, a pretty dress, and even some jewelry. We played together that way for a few hours until the girl's mother came home and saw me in the dress. She freaked out, made me change into my boy clothes, and told me never to come back again. The next day, none of my friends, nearly all of the girls in my class, would play with me. The teacher told me I had to go out and play with the boys. The mother had called all the girls' mothers on the PTA as well as the teacher, to make sure that I wasn't allowed to play with girls anymore.

I kept dressing on the sly all summer, dressing in my mom's clothes, digging them out of the clothes hamper. Mom finally caught me and bought me a pair of tights, but dad insisted that I get a matching T-shirt and had mom make me a cape, so I could be "Superman" instead of Wonder Woman. Big let-down.

From that point on, I lived in "stealth mode" for nearly 20 years. I came out to my first wife when we moved in together, but before we were married.
I didn't go public until I was 34, and a year later I was seriously considering transition. After my dad died, when I was 55, I decided to transition.

[Xandra]

You make a great point about wishing you'd come to terms with who you are at an earlier age.

I must have been younger than four, I remember it because it was way before my parents divorced, my female cousin who is my age came to my house to visit and left her very pretty jacket in my room, I snuck upstairs to was it an was caught by an older cousin, I was very embarrassed and it left an impression on me, however, I've never stopped. Much as I tried I've never stopped, I just wished I had come to terms with who I am when I was younger, this way I believe I would be in a bette place with my self.

[SamBrook]

I was 6 when I first tried on some of my sisters panties. They felt so good I couldn't get enough so I tried her leotard too. I remember even sleeping in those panties I had and now I am still the same way

[Jessica S]

I was helping my mom sorting socks and a pair of my mom's Kneehi's were in the pile, I was around 4 or 5. Something clicked and I had to try them on. Then came pantyhose then panties and everything...

[Rebecca Cross Bracer]

I remember having an pantyhose fetish at an very early age. I think I was 10. I loved The way they looked on women, how "see through" they were, The shine they gave off and how cute they made feet look. It was within that same age that I wanted to know how they felt on me so I stole a pair of my mom's. They didn't look as good as they did on other women (to find out it came down it brand and such) yet they felt amazing! There was little turning back after that.

Almost the same story for me, but I loved the look and feel of the pantyhose and progressed from there. Slowly at first, mostly just pantyhose for a few years, then my sisters' bras and dresses, now all out when possible.

[Karen_the_Cutie]

i wasnt even in kindergarten yet, so i guess like 3 or 4. first thing i wore was my sisters pantyhose. also my moms bra (which was waaaay too big for me being so young. lol) and my sisters nightgown shortly after, but not same day. I wish I had been open about it then, I even knew I wanted to be a girl then. I remember playing with my grandpa and asking him to call me tiffany, cause that was the cutest girl in my class and i wanted to be like her :3

[Christine.Lolita]

I have memories of wearing my mother’s clothes at around age 12. If I had a sister I am very sure I would have been wearing her clothes much sooner.
I bought my first dress when I was 32. It was a French maid dress I got from “LD Fashions” an online shop that sells sissy dresses, little girl dresses, and maid dresses. I had no shoes, makeup or wigs.
I wore the dress for about 4 months and when I had to leave home for work, which was my own house, I was so worried that someone would find it I threw it out before I left.
In hind sight that was a silly thing to do.

[monica.missil]

I was 12. Put on mom's bra and girdle. Then put on her nurse uniform.

[Xandra]

I love the progression!

I was 12. Put on mom's bra and girdle. Then put on her nurse uniform.

[renee elizabeth]

started when i was around 7 or 8, i started coloring my toenails with markers because i wanted them to look pretty, then i started to wear my mom and sister's clothes and makeup, never was caught

[DaisyDell]

Wore costume dresses at my neighbors house when I was probably 7. We would "force" each other to wear them and dance around and act like a girl. Started regularly wearing moms hose and lingerie when i was probably 10 or so. I would put on entire outfits with bows in my hair and model in the mirror. Didn't dress for a long time before and after i got married, and I buy my wife lots of lingerie. I just put on her swimming suits a few weeks ago and it all came rushing back. I would say it felt like another "first time"

[Gia Villafana]

Seems like 12 is a very common age! That's when I wore my mom's underwear and stuffed using tissue and later baggies filled with water. I stole bras from various family members and friends. When I turned 16, I was able to drive and get my first wig from a black beauty store. My first forms were those little silicone breast enhancers.

[ringedjohn]

I tried on one of my mother's girdles when I was around 12. Shortly thereafter I bought a light-weight pantie-girdle for myself. The fascination with girdles/pantie-girdles has never left me. Bought my first corset at around 22 I think - and about the same time I tried on my first bra. Nice memories.

[Princess Grandpa]

I have been giving this a lot of thought over the last few weeks. The first memory I have is coming across mom's teddy. I guess I was 12 or 13. If it was going on before that I just don't recall. I have been wondering of late if maybe mom played dress up with me in retrospect she clearly wanted me to be a girl. If so, I would like to thank her.

Hug
Rita

[Seana Summer]

I first tried on my sisters pantyhose at 3 or 4. I don't remember for sure but I know I wasn't in school yet. Don't recall trying anything else on until I was probably 8 or 9. When I was 10 or 11 I found a box of nylon stockings! WOW that was the best discovery ever (at the time). At 14 I was dressing up, strictly in private, in nylons, panties, bra, slip and dress, mostly from my sister and other relatives. Then I gave it up until I was out of school, I recall purging at least once One time I dug a deep hole and buried my cloths!!. Somewhere around the time I broke up with my girlfriend at the time, several years later, I started getting the urge to start again, this time I bought my own cloths.

Ahhhh the memories

I will now reminisce the rest of the day!!

Seana

[Christina81]

I was pretty young. I was in that age of cuteness of 5. I wore my sister's dress and went down to my mother with it. I cant remember what she said though. I didn't take much notice of women's clothes for years after until my sisters grew up and instead of playing with my older brothers, I played dress up and played with my younger sisters. Now I have my own clothes and love who I have become.

[Courtney . J]

dont remember my age , probably 4-6yrs old , but for some stupid reason my brother talked me into wearing a pair of my moms panties for a day ,. i think we made a bet or something that i would get something if i did the task

then a few yrs later i stole one of my other brothers metallica tapes ,. he found out and the only way he would let me keep the tape is if i (again for some stupid reason i have no idea why) would let him put lipstick on me as a joke or to make fun of me , or whatever .




funny thing is they had no idea that i actually enjoyed these things and them feelings have never left me and have only grown stronger


if only they knew what they started , idiots ... lol

[ange_o]

Probably was around 6 or 7 years old. Was in my parents room and tried on one of my moms bra's that was lying there. Coincidentially was also the only time I have been caught dressed.

[Hannah W.]

I was about 12 I guess, like many of us I starting trying on my mothers clothes. Felt so wrong & elicit...but so right too! Feelings disappeared in my early 20's but have returned recently & now I'm out to my wife, feels so good that I can actually act on my feelings!

[Claire Cook]

Probably around 4 for me when my mom let me play "dress-up" in one of her old dresses. Soon graduated to getting into her lingerie drawer whenever I could -- girdles, bras. Shared the guilt many have expressed here. but it just felt right. My fave thing was a crinoline -- I loved wearing that, and have not seen one like it since.