How Did You Get Started Dressing?

[EjayeCD]

I started in an unusual way. When I was around 5-6, I only had girls to play with in my neighborhood. The boys in the area were all older & didn't want a little kid hanging around with them, so I just played with the girls. Of course, all we played were girls games including makeup & dressup. I really enjoyed playing dressup & simply got hooked. I kept dressing even after I had boys to play with & when the girls lost interest in playing dressup with a boy when we got a little older, I was crushed by not playing with them. Then I started dressing in my sister's & mothers clothing. I never stopped.

[susie evans]

it's been so long ago i don't want to remember just get better at it
practice makes perfect:heehee: :heehee:

susie

[Jeanine]

I have an excessive amount of Estrogen in my body. The condition
is called Gynecomastia, and my breasts started to develop at 10 and
11 years old ... Everybody made fun of my "Boy-Tits," called me horiffic
names, and told me I needed to wear a bra ... By age 13 my boobs
would fill the cups of Mom's 36B bras ... I just added just added
stockings, dresses, slips, and high heel shoes as time went on ...
I fell in love with the way female clothing feels on my skin when
I'm "dressed" over 40 years ago and I've never looked back.

Jeanine

[tvbeckytv]

everyone seems to have such vivid memories of what sparked their dressing.
I have to say i can barely remember a thing before the age of 7, and know i was regularly dressing by age of 10... what happened before that i have absolutely no idea

[Kristen Marie]

While most of my memories are from my early teens, I do have some vague memories of when I was in the 1st and 2nd grade playing dress-up in my aunt's gowns. She let us have them because they were all outdated. I remember keeping them in a club house. This is like a flashback.

[Helen MC]

Back in 1965, at age 12 by wearing a pair of my 14 year old sister's school knickers , then when I could when alone at home her other clothes especially School Uniform (we took the same size in clothing) and went on from there, that's 42 years now.

I had always been attracted to girls' clothes, dolls toys, comics, and games rather than boys'.

[Daintre]

I can remember my first time, I spotted my older sisters bikini in the bathroom drying and I just knew I had to try it on......that was the beginning. Its funny 'cause the bra portion of the bikini was so padded, I didn't need any filling :heehee:

[Samantha Jane Foster]

I didn't start until I was out of college, which seems weird. But I had an older brother (still do!) who would have beat me up badly if he had caught me wearing women's things (he picked on me anyway). We lived in a rural area and my dad was a rancher (still is), and as a highly impressionable sensitive kid I tried to fit in by acting tough and macho. We were also very religious and I was afraid I would go to hell. My mom wasn't allowed to wear makeup or jewelry so it wasn't around to tempt me. I was a bright kid (what happened?) and maybe was smart enough to know not to do certain things, for the safety of my as-yet-unbloodied nose and my as-yet-not-hellbound soul. For these reasons, I just shoved down all my desires until almost the end of college. One time when I was home, after I had graduated, I put on one of my mom's dresses and felt-- alive (though I looked a little ridiculous).

Going back to when I was four or five I always thought I was ugly. In high school I was constantly in a state of deep depression. I'd wake up and look at my shoulders and chest and every black hair was like the leg of a spider crawling up me. I wanted to destroy my body. Anyhow, on a more cheerful note, I tried to kill myself after my college girlfriend left me-- afraid that now that she was gone, I'd really end up as a gay crossdresser (which I did, luckily).

I always thought girls were beautiful and I would stare at their faces and figures for hours. But it didn't make me happy being with one, at least in the sense that even though l loved each of my girlfriends (not three at the same time, mind you-- I wasn't two- or three-timing), I still felt very empty inside and sort of like I wanted to disappear into their being, become completely absorbed by their identity, because I hated playing the role of the guy.

Well, one evening in the late nineties I was in the bath and for some reason I decided to shave my armpits. Then, clearly not in my right mind, I proceeded to shave my lower legs. I liked it-- they looked like girls' legs. Later on, stomach, chest, etc. I bought a pair of black panties from Victoria's Secret. The rest is history, or herstory, if I wanted to make a corny play on words (which I don't).

[franvonceder]

I started when I was around 11 years with bras, girdles and panties. As I grew up this has gradually developed over the years.

Fran.

[Sweet Jane]

Hi

I can so easily remember my mum getting a pair of my sisters frilly panties on me, and then locking me outside when I was about 7....still don't know why. Maybe it was just something she did for fun? I'm not sure if this was my first exposure to girls underwear, but it's my earliest clear memory....now you can't get the panties off me!!

[RobertaFermina]

My College Roommate was a Beauty College Student.

She dared me to 'dress up' for Halloween.

I take non-lethal dares now and again, so she and a few of her colleagues 'did me up proper.'


I enjoyed the Dance and the lift from the floor and hot kiss from a tall boy in a football uniform. It didn't make me gay, but it sure made me laugh and wonder.... My Roommate thought it was funny too.

I did it again several times over the next 25 years before getting serious about it last fall.

:rose: Roberta :rose:

[Kellicd848]

I was about 10 and was always curious about what my sisters clothes would feel like on me. So one day I tried on some and I was hooked after.
Katy

[Casey Morgan]

The first time that I remember I was 13 or 14. I tried on a pair of underwear and loved the feeling, both physical and emotional. Then I started wearing what I though were old clothes that were being stored in my closet. The funny thing is, I almost didn't start crossdressing. I already knew I was different, so putting on that underwear was a mix of "don't make it any worse" and "what the heck, you're already wrong, what have you got to lose".

[Amy Hepker]

I really think the first time was when I was very young around 6 or 7. My sisters played dress up with me, I don't know if I asked to be dressed up or not, but I do kinda remember the dress. It was a dress that got handed down from sister to sister. I had three all older than me the youngest being 5 years older. It was a dress for young girls that had not developed the top half yet. Just a pull over style no zipper or buttons. I do remember it was Polyester as it was soft. I think that is when I got hooked. After that I remember wearing my sister clothing when I was home and nobody else was. I used to look at the Aldens Catalog and wish I could be those girls wearing all those Pretty dresses and underclothes. Oh yea Bras are the most important part to me, and I really like White full cup Bras. They are so girly.

[MarinaTwelve200]

For some odd reason I developed a fear of the sloppy red lipstick my mother and older high school girls wore in the mid to late 1950s---I was about 8 years old. I was afraid they would put it on me and I couldnt get it off and I would be very humiliated.---not to mention look like a girl. The fear was almost erotic.

Finally, about age 12, I was home alone one day, I saw my mother's lipstick in the bathroom, so I decided to face my fear and put some on myself. I tested a spot on my arm---and found that it DID come off----then I smeared it on my lips. I got quite a high out of that, and later did it whenever I was home alone and had a chance.

I soon progressed to "Seeing what I would look like as a woman" and began to dress in moms clothes---fully dressing by age 13-14---all in secret of course---I never was caught. Of course, makeup and LIPSTICK was always essential.

[SandyR]

Its so great to hear all the honest replies, all you gurls rock!. My first time was at the good old age of 12, tried on my moms pantyhose. Felt so natural and nice. Very relaxing.

Well one thing lead to another and here I am. 30+ years latter and getting better at it!

Huggs........

SandyR

[ArleneRaquel]

At that age I started, not frequently, wearing my mother's hose. For many years my " dressing " waxed and waned, during my marriage it rarely ever happen, and certainly not more than underwear. After my wife death I started dressing again, and very quickly to went to 24 / 7. :love: & :hugs: Trina - Red Haired Irish Vamp

[SandyR]

Thanks for sharing your experince. That must have been a real step to try on the lipstick, red... Well I think you look great!


Hugss....

SandyR

[Michelle_CD]

I didn't have any sisters but my friend did. So one day I saw a pair of his sisters panties in a laundry pile and they looked so soft and smooth that I just had to take them. That was in 6th or 7th grade and I have loved the feel of panties ever since. I buy them now instead of stealing them. Eventually I thought to myself if panties feel this good then what about everything else. Turns out almost all womens cloths feel great.

[Lanore]

I can't remember ever not feeling female. Fifty years ago, the only thing I was told, 'I'll grow out of it or it's a phase'. The only ones who made fun of me were some of the kids I went to school with who would laugh at how I used the bathroom or the position of my feet when I was standing. So much for the growing out of it and phase thing. Now I'm very happy with who I have become.

Lanore

[Eugenie]

I always loved the soft touch of silk, satin and fine nylon lingerie. So arount age 10, I started borrowing my mom's slips and girdles, at that time most women were wearing girdles...

I just loved the feeling of my body being held tight and touching the girdle front satin pannel with my fingers was enough to turn me on tremendously. I soon moved to using my mom's "all in one open girdles", fillinig the bra cups with nylon stockings.

It is only progressively that I went further in my "en femme" dressing experience. Actually I only fully dressed "en femme" a few years after I was married. By that time I had already told my wife about my desire to wear female underwear and night gowns... I shall say that this move to full dress attire didn't please my wife who had rather easily accepted wearing women underwear as a sexual "fantazy" but didn't like the full "en femme" x-dressing idea and still doesn't...
:hugs:
Eugenie

[Phyliss]

I've told my "full" story in both the introduction forum last year when I joined and again in the writers section. Long story made short, I was 9 when I first explored the idea of "underthings" , Loved it instantly. During my teen years I somewhat surpressed it, even when so far as to join the military to cover myself. Somehow that didn't work too well. About 12 years ago I began again with the "undies" and the old feelings came flooding back, about four yr ago I progressed to the top half. As we all know "you can't do things part way"
So for the past year, I've been fully dressing when I can. "Came Out" to wife this past Oct (of 06). At least I don't have to hide anymore.

[Joanboy2001]

My older sister would dress my up in her doll clothes when I was a baby and continued to do so till I was almost 3. I don't have a particular memory of but my sister has told about it. I have always wanted to wear women's clothes, underware and accesories.

[NatashaCD]

i was about 6 or 7 one night i went to my aunts wardrobe and tried on her vintage brown knee high boots since then ive always wanted to dress but never could until about 19

maybe thats why i love knee high boots so much

[kateyliz]

I don't remember it starting, it's always been a part of me. Hugs, Kathy

[StephanieH]

4th grade boy's beauty pageant. All us boys in the contest wore our female attire the whole day and I knew right there that something was definitely different about me! I won the contest and also won another one in the 11th grade! :heehee:

[sharon2]

when iwas about 5or 6 i used to watch my mum dressing and doing her
makeup and i would wear her bra over my shoulders and clomp around in
her highheels.my sister and her friend used to dress me in their clothes and
i loved it. mum then bought me my own girl clothes and often took me out
as a girl.in our teen years my sister and i sometimes went out as girls.
in my late teens i found other interests and stopped dressing .i started again
at 25 after i was married.unfortunatly my wife dissaproves.

[linnea]

At age seven. I tried on my mother's girdle that was hanging on a line in the basement. She actually caught me doing it, but she only said, "What are you doing?" I answered, "Nothing." I never heard another word about it.
Looking back at this, I have thought that it was odd, but since that time I have found out or remembered several things that may have lent themselves to influencing my crossdressing. One of these was that my mother bought me girl's underwear throughout my childhood until I started junior high. It was just panties, nothing more, but I didn't realize that that is what she had done until later on. I also remember that on a couple of occasions she had me try on dresses when I was with her while she shopped. This occurred when I was quite young, maybe between the ages 4 to 9. She also said to me on several occasions that she wished that she had had a girl. She never said that she wished that I had been a girl (I was her second boy, out of three, and no sisters).
From seven through the end of high school, I dressed mostly in my mother's clothes when I had opportunities while she was away from home. During the latter part of that time, I started to buy a few items of my own--mostly bras, stockings, and panties. After college, I began to accumulate more complete sets of clothing, but purges would wipe those stashes out periodically. For the past fifteen years, I have been more fully involved in buying and developing the clothes for my wardrobe, no longer purging. I get rid of things--underwear, makeup, other items--when they wear out or go out of fashion or I just don't like to wear them any more.

[Kristen Marie]

While my mom had lots of white bras, slips and girdles, my aunt had the good stuff. Colored bras, bra slips and panties. She would always have them lying around when I babysat my young cousins. She must have know. Those are my best early memories.

[Roxi Loh]

I started playing superhero and wanting to wear tights. When I tried on my sisters something happened. I loved the feel and translated that to other women's clothes and such. It just grew from there.

[sandy_folsom]

I see there are quite a bit of people who's first time was when they were 12. I wonder if it's somehow related to the onset of puberty.

For me, I was 12 when I first started having the urge. For me, it was wearing my mother's faux-fur coat and leather boots (and nothing else ;)).
At that time, it was more sexual than wanting to be feminine.

[britney]

when i was really young with my sisters underwear

[imDanielle2]

I dressed some as a kid but it really took off when I was in my teens with a girlfriend. I lost a bet and she curled my hair, did some false eyelashes, shaped my brows a little, makeup and had me in a tank top and denim skirt. We almost looked like sisters. Anyway it just gradually turned into a normal ritual for a couple years or so then we split up.....But the dressing never really ended, just went back to the closet for a while but its full blown these days :)

[Colleentg]

It all started out of curiosity. In 2nd grade, my teacher's leg brushed up against my arm at her desk and I looked down to see what that 'new' feeling was. There is full glamour was her shiny nylon leg, staring back at me! Wow, I can remember it like yesterday. Even though my mom wore beige stockings with her long-leg girdles, it was my teacher's leg that grabbed me. She was only in her mid 20s, then and she was a doll, too. She always wore shiny hose under a skirt, everyday. Now I know why my grades were so bad LOL.

A couple years later, and all the while, I was ogling girls' legs at school all the time. How I wanted to touch and feel them, and wondered how they would feel on my legs. My older sister wore the latest fashions and always wore a short skirt with either pantyhose or bold color tights. In fact, she'd often parade around the house in just her bra, panties and tights. I wanted to do the same. But I knew that I couldn't, but secretively. Since my sister was a slob, I ventured into her room and walked thru pair after pair of worn tights, pantyhose, bras, slips, control type breifs and regular panties, as well as tons of other clothing that she would just peel off and leave laying on her floor. It was a closet CD's haven! What to choose? What to choose? I picked up a pair of navy blue tights and stuffed them in my pocket, then hid them in my bed until bedtime. Once in bed that night, I removed my white boy briefs and managed to slither into her tights under the sheets and blankets. OMG! It was the best feeling ever! Of course, at that age, it brought on high sexual feelings, too. But along with feeling them on my legs, feeling them against the sheets as I moved about before 'getting off' was truly the best feeling ever. Night after night, I was wearing a different pair of my sister's hose, eventually trying on some of her bras, slips, skirts, even shoes when I was home alone! The best secret I kept from my sister is that I wore her white wedding merrywidow corset at least a dozen times before she wore it for it's purpose! Then I was jealous, at her wedding, knowing she was wearing it under that fancy wedding dress. I've been hooked on corsets and hosiery since! But's how it all started. I never got into my mother's clothes, because they didn't appeal to me and because they were oversize (to me). At that time, I thought of girdles and brassiers as junk underwear, like boys briefs are. I changed my thinking since, because I also love wearing those tight-white girdles, brassiers and bodybriefers now and then.

[soccervixen]

4 months ago when my wife and kids were out of town I slept in some of my wife's lingerie. That did it for me - first time, and I was hooked! Now I have my own lingerie, with a burgeoning panty collection (over 30 and rising ...)

And this is by the way at age 47 ...

[Tina B.]

At Seven or so, I fould a bag of old clothes in the storage shed in the back yard, old shirts that my brother and I had out grown, and my sisters old stuff. Well I didn't care about the old boys clothes, but I sure took to my sisters stuff, at first the fear of getting caught, kept me from doing much more than putting on a skirt, or dress over my clothes, but then as the youngest kid I got of school much earlier than the rest, and found with dad at work, and mom never went out there, so it was get home from school and out to play, I stole some under wear of my sisters, it was old stuff she didn't use much.
I would spend hours every week with my stash, and was broken hearted when Dad threw it all away, while cleaning up the shed one weekend.
I was never into sports, or competing with the other boys, and always preferred to play with the girls when I could, their games just fit me better.
Tina B.

[Angela E.]

And I naturally gravitated towards girls for playmates.Hmmmmmmm....I guess some things never do change.:hugs: Angela.:bunny: :<3: :bunny: :GE: :bunny: :rose2: :bunny:

[JenniferMBlack]

when I was 11 I found one of my sisters skirts hacd wondered for years what is was like to wear a skirt so I put it on and was hooked from there. over the next few days tried other things of my sisters and moms. one day my mom found one of my sisters skirts in my dresser drawer and all she said was " one of your sisters skirts is in your drawer I don't know how it got there but for all I care it can stay there" other then that don't think anyone ever knew till I came out last year.

[MissAnnM]

Not sure when I first started but I remember the first time I was caught. I was 6 at a neighbor’s house playing dress up and up guessed it I was in a dress. Her mom called my and it went down hill from there. I learned few things that day. mom’s don’t like their boys in girls clothes, don’t tell her that you like to wear them, and keep it in the closet.

[SANDRA MICHELLE]

I was about 7 years old and had a nagging urge to wear my sisters clothes, I used to put on her undies and dresses all the chances I could get. Even at that age I knew it would not be acceptable since I was the oldest boy and my sister was a year older I had to act the part. I used to hide a stash of her clothes and wear them as much as I could. Now I have my own 43 years later.

[geekinthepinkcd]

I distinctly remember being in Junior High and staying home alone sick from school (both parents worked). I was bored as hell and wandered into my mom's closet and started trying on her stuff. For some reason, it activated some weird gene in my brain and I've been hooked to it ever since. Of course, these days, I have my own clothes.

[kaitlin]

Well Girls, How I started is a long story. I have always, as long as I can remember, liked and wanted to wear female things. When I was little 4 or 5 ? I got into trouble alot for messing with my mothers makeup. When I was a little older and into building model cars, I would wait until mom and dad were asleep and paint my finger and toenails with model car paint. It just progressed from there, I was lucky enough to find a few girlfriends over the years that would play a little. None of them had a clue to my real needs. I was totally back in hiding for 15 years, (two bad marriages) now it's all out. I can dress any time I want. And to top things off, I have what apears to be a surgury scar in a strange place, if ya know what I mean. I asked one Doctor friend what she thought, when I got my vasectomy done, she thinks I may have been born with both sexes. Being this was in 1961, no medical records exist now. But the scar is in the right spot and size for this type of surgury when it is done at birth. I guess I will never know for sure but it would sure explain a lot of inter feelings I have and how I was treated, according to my aunt, when I was a baby. Kaitlin

[kris_dresser]

It all started when I was around 7 or 8, and my best friend who was a year or two older, found his older brother's playboys. This was in the late 60's early seventies, and we decide to raid his sister's closet and pose in her cothes. Stockings, garters, slips, mini dresses...oh to go back in time. Unfourtunatly it ended when he reached puberty and got a little too agresseive.:sad:

[SarahMus]

I was never interested in boys clothing styles. The first item of clothing I was interested in friends sister skirt and envious that she could wear it. Didnt have a sister so had had to wait until I could fit ino my mothers clothes. After that whenever they were going to be gone I would slip into one of her skirt and blouses. So glad that I now have my own collection of skirts.