I was maybe 7, had been at my cousins playing and got dirty and my aunt gave me my female cousins clothes to wear til mine were washed cause we were the same size. Been hooked ever since
I was maybe 7, had been at my cousins playing and got dirty and my aunt gave me my female cousins clothes to wear til mine were washed cause we were the same size. Been hooked ever since
13 years old
I was probably 8 or 9 when I dressed the first time. I was fascinated by one piece swimsuits. My mother had several and I stole one and hid it away for myself. It was black with little lime green stripes. /sigh
It started late and developed slowly over years/decades for me. Think it began with girls' jeans when I first started buying them myself, about 16-18.
I was 7 or 8 with my mothers pantyhose and never looked back.
8 or 9...maybe 10...trying on my mothers shoes and tights and my aunt's lingerie and clothes. also, my aunt was a equestrienne who had jodphurs and riding boots and tight vest-like jackets. they were incredibly hot. to this day I appreciate tights, jodphur-like pants (with silk panties beneath) and a great looking pair of boots.
I was around 6 or 7. My mom worked at a non-profit agency and would always bring home bags of clothes that she would sort through. When she wasn't looking, I acquired lots of girls pants and shorts from helping her sort though the clothes. Oh, they are sooo comfy! I love the fit and feel of them! To this day, I still wear women's jeans while in drab because of how comfortable they are.
As much as I can remember, I first put my feet in my mom's shoes at 5, maybe a year or 2 later, but I knowingly crossdressed for the first time at age of 12, when I put mom's pantyhose on and walking around the house dressed like that when home alone after school. Soon after that my "crossdressing career" started and I wore her clothes as much I could, when no one was at home.
I was about 8, started wearing my Mother's panties.
Off and on ever since, you know, acquire panties and bras, the purge.
Now back at it with a vengeance.
Well, I'm kind of new to CDing. And to the board. I'd put this in my intro but:
I'm unsure when my first literal crossdress was.
First CD technically probably happened after winning a camisole at a lingerie party I DJ'd back in '86,'87. (didn't have or get girlfriends so one day thought "let me try this on... " ) This was probably within a year or 2 of winning it. Still have it too, although it really doesn't fit anymore. Amazing how clothes shrink even while in the dresser...
I've been cross-dressing all my life. I can't remember a time when I didn't enjoy it. Even as a 3-4 year old, I remember going into my mom's closet to "play mommy". I think I believed that my mother would love me more if I was born a girl.
Probably about 12 or 13. Mom's pantyhose. I was so enthralled by them I stole them outright.
Many years later I tried on my first dress. That was simply amazing.
In sixth grade, about age 12. It was Halloween and a boy in our class wore a beautiful dress, heels, and wig to school. His mother was a beautician. Everyone thought he was a substitute teacher. I was totally fascinated. I wished I had the nerve to do the same. But I kept my escapades with my mother's clothes and cousins bathing suit totally secret. Except when I was caught--and my parents wanted to send me to a psychologist. I told them it was only a one time thing. Ha!
I was perhaps 4 or 5 when I would hide under my mother and father's bed when dad was at work and mom was housecleaning or preparing dinner (amazing how at that age I was thoroughly aware that it was wrong or shameful) and put on my mother's nylon stockings simply loving how they felt.
I've told this before, but here goes. I started at age 59 - 60. Yeah, REAL late. Never tried anything of my Mothers, had no sisters or close female relatives. I think I'm getting better at it!
Hugs,
When I was about 8 I would wear my Mums tights (pantyhose). Even then I loved the feeling when my legs rubbed against each other.
Same here. Late fifties.
Went to a costume party as Charley's Aunt in a large hoopskirt, laced hooped petticoat wig, bonnet, lace fan , string purse and satin pantellettes with a lot of lace and makeup.
It was a lot of fun, so I have been developing some female costume characters along with my male ones.
Basically I do this at costume events or Halloween.
Sometimes I like to do just a lady and not necessarily a costume characters. Try to keep everyone guessing! Lol!
So want to perfect my walk, voice and mannerisms.
Lets see, i tried on things when i was a teen. Mostly moms things. Really only got serious about this "hobby" like 3 years ago, so really i probably started "dressing" 3 years ago.
Since i was 13. I painted my toe nails and wore women clothing until i got caught and a beating
I was a late bloomer...a gf dressed me up a bit in college but started in earnest about 6 years ago.
hey my frends... I was start wearig girls clothes obaout 3 years ago,when i was 26.... first i use thung,nylons..and stuff from my girlfrend, i was use her clothes 6 month,than i started buying my own....
Last edited by PurryCross; 11-17-2013 at 10:18 PM. Reason: mistake
i'm soooo depressed that i missed the beginning of this thread, and i wanted to post so badly that i only got through the first 20 or so posts before skipping here to the end to post my own:
i suppose it depends on what you mean by 'crossdress'. like a lot of us here (and probably a lot of boys who'd never have an interest in coming here), i recall a female relative ---- my paternal grandmother --- tying a scarf around my head when i was maybe 6 and telling me what a pretty girl i was. i think one time she even put lipstick on me. but i recall that instead of finding it thrilling, i found it annoying.
some time around age 10, i started to develop a fascination with two things: the first was women's boots. i frequently spent days at my aunt and uncle's house while my mom worked, and in the garage i discovered a box of pairs of go-go boots of many different colors. my older (gg) cousin was part of a dance troupe at the high school and she'd purchased the boots for various routines. after trying my best to resist, one day i rolled up a pantleg, slipped my foot into the right boot of a red vinyl pair, and pulled up the zip. as i felt a rush of excitement and an erection that surprised me, i turned to see a neighbor boy staring at me through the garage window. he took to calling me 'rachel' in private but never outed me, and i now realize he was fascinated, actually.
the other fascination was women's clothes made of certain materials that at the time i thought of as 'shiny' --- leather, leather-like, and pvc/patent materials, and when i'd see them (usually in pop culture, not my conservative midwestern surroundings), that meant miniskirts and boots, naturally. the fascination wasn't yet about wearing them, but i couldn't stop looking at them. i remember tearing a small ad out of a magazine ---- i think it may have been popular science!!! ---- with a photo of a man in casual clothes standing as a woman in a faux-leather top, miniskirt, and boots had her arms thrown around his neck and gazed at him adoringly. i hid that ad in a book of mine and actually found it twenty or more years later....
it was around this time that i started obsessing over a fantasy, working it out in more and more detail. i was the only child of a clothes-obsessed mother who frequently took me shopping with her. i began to fantasize about stumbling into a secret back room in the women's section of a department store where i'd be asked to choose items from all departments to be brought to me as i transformed myself into a woman, by all appearances, and then walked out to ... escape. as an adult woman.
it wasn't long before i started trying to make myself appear feminine, but it was only kind of dressing. most of the clothes i wore were my own, but i'd add a pair of boots my mother had abandoned in the basement, tried to use some rags and a shiny piece of fabric to create a bandeau top and small breasts, and tie a scarf over my head to hide my boy hair. this started out terribly exciting but quickly became ..... frustrating.
i was 12 or 13 when i finally 'went all the way'. like others here, this happened on days when my mother had to work but i had no school. i quickly found the only sexy pair of panties she had and used carefully rolled undershirts to fill out the bra. the very first time i raided the drawer in her dresser that held her pantyhose, i discovered this odd pair of items all the way at the back, sheer and black but only long enough to cover a leg each, and my fascination with stockings began. (it also explained the strange clip-like things on each leg of the girdle i wore --- it wasn't until i went to university that i realized that garter belts weren't only worn by naughty sexy english girls in music videos and monty python sketches). i chose a suede pencil skirt and a bronze-colored satin blouse, tied a satin scarf around my neck (even though my adams apple wasn't yet big enough to need hiding), and a pair of strappy black patent sandals with 3-inch heels. that's pretty much what i wore every time ui dressed for the next two years, nearly. i got pretty good at makeup, but hair was always a problem --- i tried slicking mine back (with vaseline --- ugh!!) but usually simply tied a scarf over it.
not long before my 15th birthday, on a weekend evening when i expected my parents to come home very late, i was mostly dressed and about to do makeup when i heard the garage door open. i managed to get everything off, but couldn't hide the evidence. my parents badgered me into confessing, which started a year of weekly visits to a therapist to 'break this habit'. the irony is that the first time i was alone with the therapist, after we talked for a while about my 'problem', he told me i'd probably want to do this for the rest of my life and that it was perfectly okay, but since my parents weren't okay with it ---- the clear implication was that they were overreacting ---- i should probably wait until i'd moved out of their house before trying again. which is precisely what i did four or five years later!
I was 13 and had a day off of school. I was really bored and wanted to see what I would look like as a girl. So i put on my mother's makeup and discovered that it was exhilarating. Of course I had to try on the clothes after that. I loved it! It was right then and there that I knew I was different than the other boys I'd known. For a while I thought I might be gay and it bothered me. But that wasn't the case. I would dress-up every 6 months or so, not very often - didn't have the privacy. Now I'm much older and I'm out to my wife. I have my own closet space with girl-clothes and heels and all. Being en-femme now & then is a part of who I am and I'm glad to have something that I can enjoy. We hafta make life liveable! Not as cute as I was when I was 13 tho! Nature - whatcha gonna do...
Goodness....I was about 5 or 6 when this fetish thing hit me which started with boots, my own, "Wellies". Rubber, pvc and leather fascinated me to no end and was determined to obtain some garments of this material and don them. Well, to cut to the chase, I have CD'd off and on all my life always in secret. Played many fantasy roles with a few partners(female), and now rarely dress. I guess with age weariness sets in but the desire is always in the back row. But I enjoyed it immensely and when I do Cd I still do.