What made you crossdress for the first time?

[Dani Alana Taylor]

I know this has probably been asked before but I am to lazy to go looking through the threads lol. I bet a lot of people are probably the same as me when I say i don't know why but I'm wondering if for anyone there were any specific reasons? Just asking!

[AmberDay]

It just seemed natural to slip on my sister's satin gown when I was five years old..... thought wearing satin was normal. My sub-conscience?

[Missy]

roll playing games at age five with next door neighbor boy I was nurse he was hurt and I had my sisters panties and bra
I kissed places where he said it hurt and so it started for my acting and wearing girl cloths and pleasing boys lol

[Chazity]

I had 4 sisters I think I was just curiouse.... And they loved to dress me up,i was a human barbie lol

[Mollyanne]

curious, VERY CURIOUS!!!!! From the first moment that I wore stockings, a garterbelt and panties I was hooked!!!!! Haven't stopped since then, and have become much more comfortable dressing, in fact I was helped by my mom.

Mollyanne

[annecwesley]

I admired the way girls looked in the 6th and 7th grades, maybe even before that. I think though it was my music teacher in the seventh grade that finally made me want to see if I could look like a girl - she was real pretty and I wanted to look like her. So one day when I ws home sick from school, on when the stockings and slip borrowed from my mom... and I was hooked.

[Jessica Who]

I had wanted to for at least a few years, then when I was around 6 or 7 I was able to sneak one of my mom's dresses on

[JillyNylonz]

Purple: that was an absolutely lovely story! Entertaining as well as heart warming. Thank you so much for posting it !
I did not have such a poetic introduction to the joys of dressing enfemme. I just took notice of my mother and all her friends that came to our house, wearing smooth shiny nylon stockings with very pretty heels. My curiosity got the best of me when I spied some laddered hose in my mothers waste basket. Before long I had some thirty stockings, all Hanes 415's, many only slightly snagged, stashed away to wear when Mom went on an errand, and I was home from school sick! I had many pleasing hours dressed in heels, hose and a garter belt walking around on an Oak floor, hearing both the sounds of those sexy heels, and the swish and zip of her(my) stockings as I walked ! I was at home, and sick a lot, after developing my newfound interest in crossdressing ! LOL !

[Talldrinkofwater]

I guess what opened this world for me was the first time i wore a dress. I was about four and at daycare playing dressup/house with the girls and a couple of the boys. The woman who ran the daycare had a bunch of old satiny gowns, slips, costume jewelry, and dresses she put out for the kids. I put on one along with a raggetty wig(i think i was supposed to be the crazy aunt or something) i loved the way the material fell so softly around meand and I guess that's when i was hooked.

[Beth Mays]

At age 9 Mom would dress me up.... still have a couple pictures stash away someplace.

[ronda]

i don't know i did not need a reason at 3 years old panties night gown and heels mom said he will grow out of that and siad i don't think so

[Fallen Angel]

I beeing a 70's baby all the clothes at that time were unisex and i guess the rest is history

[inori]

Because I want to feel pretty and cute :P And also I was always jealous when I saw a good looking GG wearing something that I was never gonna be able to wear.

[Regan]

I just remember always being fascinated in my mom's pantyhose and bras so when I had the opportunity go be alone I tried them on and have lived the feeling ever sense. This is also when I really started fantasizing about being a girl and always felt do comfortable with it. Unfortunately had to stuff those feelings for 40 years.

Regan

[~Joanne~]

I believe being a teen in the 80's drove me to where I am today. The women always wore pantyhose with almost everything and I loved the look. still do ;) At one point I had to know what they felt like on, then came the heels, then it is where it is today. Spent a lot of years denying the whole thing but within the last couple I have come to terms. Pantyhose are what still brings it all together for me :)

[LeeBe]

I really don't remember when my first thoughts of CDing were, but I do remember that I was always wondering what it would be like to wear girls clothes. I would see girls wearing some neat looking outfits in school and just be so curious as to what it would be like to wear that.... it must feel so different from what I had on (you know regular guy clothes). I followed that same line of thinking when I would see fancy ball gowns in the movies.... I thought it was strange none of my buddies never shared my thoughts about girls/women's clothes, so I kept those thoughts pretty close to myself. Then one day I just came to the conclusion that all these thoughts about wearing women's clothes was just plain stupid and I had enough of that, so no more, done finished with that, period! I guess you can tell that really worked out well! LOL Anyway, from there it has just been a series a little steps, a few more items, just a little here and there and so on. I guess it always has been and always will be a large part of who I am.

[NitaCD]

The first time I crossdressed I was 6years old. I was in the hospital for a tonsillectomy and had to wear one of those flimsy hospital gowns with no under pants. I complained enough to my mother about it until the nurse finally found a pair of pretty girls panties with blue flowers for me to wear. And as they say "the rest is history". I have been crossdressing in some form or another sense that day and love every minute of it.

[Karren H]

Don't know why except possible my mother used to remind me I was supposed to have been a girl a lot growing up... But one evening when I was 7. My parents were out on the town and we had a baby sitter for me and my younger brother..... they were both in the living room watching TV and I went off and explored my mothers walk in closet. I tried on girdles and bras and ruffled panties and a baby doll nightie.... Nylons.. High heels... After that I was hooked and would sneak into her closet when ever they were out...

[Marleena]

I don't know why either. I had an older sister that just got her first party dress with nylons, girdle etc. I found it in her room and had to put it on. Of course I got caught in it. My sister made my life miserable about it with her teasing. I had no idea what I did wrong.

[Kate Simmons]

Nothing made me really. It just seemed like the thing to do at the time.:)

[Kristyn Hill]

My experience is real similar to Karens from the start. I was wearing my moms patent go-go boots in '73-'74 era when I was 3. From 3 on I snuck into her closet wearing her heels any chance I could. I did this until I didn't fit into her size 7 1/2" foot anymore. At 18, I bought my first 2 pair of heels at Payless then a 3rd.....purged later. Bought more....purged. Now my wife is completely GREAT with it and we were the same size so no more purging.

[Jacqueline Winona]

Just the thoguht of Chrissie Evert in a tennis skirt got me interested, then my mother started wearing pantyhose for a new job and I just had to try the hose on- simply fascinated me at the time.

[kimdl93]

very common question, but there are always new people here. for me, the desire was innate. I recall thinking about women's clothing in some of my very earliest recollections - even dreaming about them. And as I preschooler first tried on one of my sister's slips.

[HannahF6]

I remember my first time in a dress very clearly. My mother used to make dresses for weddings. She'd typically have a couple of wedding dresses and many bridesmaid dresses in the house at any one time. When I was a young teen she'd use me to model them. I loved the feeling of being officially "pretty".

I do remember hamming it up one time with my father pretending to lead me down the aisle, mother thought it was a tragedy I'd not been born a girl, especially one time when she announced I looked better in the wedding dress than the girl who was supposed to wear it.

Hannah

[Julie Denier]

[QUOTE=Miss Joanne;2784552]... being a teen in the 80's ... The women always wore pantyhose with almost everything and I loved the look. still do [QUOTE]

That's a big part of it for me, too. I started clomping around in Mom's heels as a tot, explored her closet on very rare occasions through my early teens, finally dressed full-on in my late 30s.

[Contessa]

I will confess I was very sneaky. I had times nobody was home with me, so I did things. things that didn't only include putting on nylons and stuff. I honestly can't say what started me but I think it had to do with all those fashion shows I had to be at and all the hanging out in the back in the dressing area. It made me just love different stuff and want parade around myself. So when I could. I loved doing it all but never everything at once. Some of my other post will tell you another more important reason. I have tried to stop. I'm still working on it.

Tess

[DCChris]

My mom made me do it the first time.


Well ... she shouldn't have been prancing around the house in her garter belt and stockings, then just leave them around when I was so young ...

[Cynthia T]

I was home alone, reading a light novel, when one of the characters mentioned in passing "high heels". Hmmm. I put down the book, went back to my sister's room, and tried on a pair. Liked it. Went on to collect more heels, dresses, stockings, jewelry.

[Krististeph]

My sister (12 years older) moved back in for a few years- she had some really cute clothes- she was pretty cool to a pre-teen- party girl and all but also good at her job. Not really the first time- but i found her wedding dress in the basement one day- while everyone was at work. Tried it on. Had fun running around the house- even noticing a classmate who came over to work in the garden their family planted in our plot (we had some nice gardening land) - Andrea, wished I could have played dress up with her. Funny thing was, she probably would have been okay with it.
My sister's stuff was primo though- this was in the 80's when a little androgyny was not uncool. Not sure if she ever knew i tried her stuff on, but she was a smart cookie- it would not have surprised me in the least.

She figured me out a few years later- she stayed with me for a month- like me- snooped through all my stuff. Got me stuff without actually coming out and saying it- too bad, the late 80's were still too uptight. I should have opened up to her- but no. Now she's aging prematurely- medical problems- still loves me as her baby brother. My family's medical problems inspire me to get out and push myself with exercise- best thing they ever did for me.

[Aylineira]

Mom's high heeled boots. At first she thought it was funny. Later on she had to hide them from me. I still found them and wore them when she wasn't around.

[Krististeph]

Don't know why except possible my mother used to remind me I was supposed to have been a girl a lot growing up... But one evening when I was 7. My parents were out on the town and we had a baby sitter for me and my younger brother..... they were both in the living room watching TV and I went off and explored my mothers walk in closet. I tried on girdles and bras and ruffled panties and a baby doll nightie.... Nylons.. High heels... After that I was hooked and would sneak into her closet when ever they were out...

What a kind mother! :-) Did she ever suspect?

[larry07]

Another closet story - when I was maybe 9 or 10 my brother and I and a neighbor boy were inside on a rainy day playing in the attic closet where my mother kept her square dance clothing. On a lark I decided to try on her petticoat. I was prancing around when she came up and found us - she wasn't pleased and made me take it off and no more was ever said. At the time I didn't know that I was crossdressing or I would never have done it in front of the others; I just thought I was fooling around. It was several years after that before I started investigating and trying on her panties and bras that I found in the clothes hamper.

[Cheryl T]

For me it was my mom's pink nylon panties. I wondered why she had things made of such a silky material and no one else in the house did. One day I tried them on and voila....I loved them. After that it was her pink (detect a thread here?) open bottom girdle with attached garters. It laced up the back and had a zipper in the front. Satin panels for detailing and OMG....a pair of nylons (no one wore pantyhose then) with seams up the back.

[jennacda2]

Pure curiosity is what got me started. I wanted to see what it felt like so I just went ahead and tried it.

[Michelle 2]

Like many of the ladies here I started to experiment with wearing feminine garments at the age of 5-6. Woman and girls in the early 1960's were treated very special where I grew up. You know the tipping of a mens hat, car doors being opened and chairs being pulled out at the table so they may sit are some examples. I always wondered why females of the day were treated in such special ways. Growing up I was taught to respect the female sex and it was proper to do so, and still do to this day.

I was impressionable as we all are at that age and maybe a tad jealous as well. I did not quite understand why females recieved such special treatments but I knew I wanted to experience them as my mom and older sister did. This led to my personal and life long indulgance to start crossdressing and I am very happy and thankful for it.

Michelle

[Lea]

My mother wanted a girl. Before reaching school age she kept my hair long and would put me in dresses. Then when I reached school age it was short hair and boys clothing.

[DonnaT]

I was 6 or 7, and playing Army with some kids. Seeking a hiding place near a neighbor's house, I saw a pretty girl from my class playing in her basement with her younger brother. He was dressed up. I so wanted to trade places with him at that moment.

I guess it stuck with me, subconsciously, and around 10 or 11, I found some things of my mom's while cleaning out the basement, and on they went.

[StacyPump]

I have a Hollwood-esque, dream-sequence, mish-mosh of memories, including: at 3 or 4 yrs old, a couple of my aunts dressing us up in their bead necklaces, high heels, fancy hats, etc.; around age 7-8 noticing, and being envious of, the cute little outfits that my two younger girl cousins got to wear...frilly dresses, white tights, shiny black shoes, ribbons in their hair, etc., a very vague feeling, though I don't recall it ever having been stated, just a vague feeling that my mother had wanted. a girl; and then there was Bugs Bunny dressed in drag. (Did any of you love that as much as I did? I remember thinking, "wow, bugs makes a sexy woman. I wonder if I would, if I wore a skirt and lipstick?")

Fast forward to early puberty, and snooping around my parents bedroom looking for girlie mags, and coming across my mom's undies drawer. I was instantly and feverishly drawn to the silky panties and pantyhose. I tried them on, and I was hooked.

To this day, whenever I dress, I am filled with those same feelings of being "special", that I had with my aunts, and while admiring my girl cousins, and of course watching that bugs bunny cartoon!

[RenneB]

I was 4 or 5 when we were over at the neighbors house and I saw the neighbor girls (age 5) dance tutu dress and thought to myself, that would look great on me. A few days later, I was at the house as mom had dropped me off to go and do other stuff and it was just me and the girls mom at the house. I took off to the upstairs, found her closet, tried it on and .....as they say the rest is history.....

Renne......

[kuromi]

Because I want to feel pretty and cute :P And also I was always jealous when I saw a good looking GG wearing something that I was never gonna be able to wear.

This pretty much sums up how I decided I wanted to CD. I always get jealous when I see adorable items for sale at a shop or online, or that a GG is wearing, and I know I'm not "supposed" to wear them. Hell, even my girlfriend makes me jealous sometimes >///<"

I first tried on girls panties when I worked at a clothing store, back in the freshman/sophomore years of high school. Girls have such adorable designs and soft fabrics! I just couldn't resist myself! So, I bought a few pairs and hid them under my bed for a couple months (before getting paranoid and throwing them away). Of course, I wore them as often as I could.

As of recently, I began a shop online selling women's clothing. I'm starting off with panties (I have over 100 pairs in my closet right now, packaged up and ready to sell). For each style that I intend to sell, I kept one pair for myself, and have been wearing them everyday since. I recently just ordered a second shipment (which I should be receiving in a few days), and some stockings. I also ordered my first wig, as well as a bunch of adorable items, including short shorts, skirts, a hoodie, a bra, and a blouse. I'm still getting started myself, so I'm really looking forward to the arrival of my items!

[Stephanie47]

I loved the feel of my mother's nylon slips that she hung in the bathroom to drip dry. There was no sexual motivation. I just loved the feel of the nylon.

[Randee]

Even though my sister and took ballet in leotards and tights and had her friends over wearing them with her, I thought nothing of it until a girl in my 4th grade class did a dance in the classroom for show and tell in a black leotard and grass skirt. I became so curious what it would feel like to wear leotards and tights like sis wore to ballet. So about a year later, the one afternoon I was home alone from school, I found her dance bag and slipped into her black ballet tights and leotards and zipped up the zipper in back after first borrowing a pair of her silky panties. It felt so wrong but it was so exciting I could not help myself. I spent the next couple of hours mincing about the house admiring myself in the mirror all leotarded. Been hooked ever since for all kinds of skintight clothing.

[Veronnie2]

My beginning was much like Ecstasy's, having 3 older sisters who were always dressed sexy and frilly, and being that I was the Younger brother that they had to watch, I was also their dress up toy. They also dubbed me with the name Veronnica which I still use today. All my menories here are pleasant and my sisters and I a still very close. They accepted me as a crossdresser when I was young, and never teased me about liking being one. Veronnie2

[ArleneRaquel]

No one else was home and I just wanted to try on some of my mother's things. That was around 1900.

[StacyPump]

I so love reading stories like these. It helps me feel not so alone...or strange.

[TGMarla]

I've answered this particular question several times, but since it's a bit unique, I'll answer it again.

When I was in the 7th grade (12 years old), one of the homecoming events was an "ugly" contest. Each contestant would make themselves as ugly as they could. I knew the theater director at a local college where my dad taught, and figured I'd have an inside advatage because I had stage makeup at my disposal. But better than that, I had a wonderful idea. In addition to some great theatrical effects on my face, I could use pantyhose with flaps cut out of it and hanging off my legs to simulate skin falling off of them. My mother assured me that it just didn't work that way, but heck, what did she know. I was 12, and I knew everything.

Well, it didn't work, needless to say. And another kid used tape and axle grease to make it look like his eye had been gouged out. So I came in second, and I had no "skin" hanging off of my legs. But I'd never forget how wonderful it felt to wear hosiery, and one thing led to another. Before a few months went by, I was dressing head to toe in ladies wear, a past-time that continues to this day.

[Mistybtm]

It was like a calling for me. I would wear my moms pantyhose at first then moverd up to her bras and dresses I was a young teen then, that lasted for severl years untill I joined the military then nothing for several years when i got married and moved back to the states I started back again with wifes panties and bra as a joke and I was hooked again. I really got back into it after my divorce and now dress full time when i am home durring that whole process I discovered my bi-side it was always there but I never acted on it untill my divorce and loved it. :)

[Vickie_CDTV]

Same here, growing up in the 80s it was de rigeur for a well dressed woman to wear and skirt or dress and pantyhose and it is a look I always enjoyed as well. I remember being in 8th or 9th grade and was fascinated by skirts, dresses and pantyhose and wondered what it would be like to wear them. Of course, eventually I tried it and loved it (and was the gateway to gartered stockings, girdles and more old fashioned womens clothing.) Seeing a well dressed woman in a dress or skirt, heels and hose always did it for me (and still does.)

[Kerigirl2009]

What made me want to wear girl clothes? Well I thought they where prettier then the boring tighty whities and my underroos. I was always around females and I wanted to fit in aand just be one of them. Still feel the same today.

[CamillaCD]

This might be one of the stranger reasons. I had dreamt about for several years, but the actual trigger was watching Keira Knightley putting on a corset in the first of the Pirates of the Caribbean movies.

[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... :battingeyelashes:

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

[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".:)

[Jenny Doolittle]

Mom's silk stockings and slip were just way to smooth and silky I had to try them. From that first time I was hooked.

[steph1965]

I was around 11 and I was at my friends house and we playing hide and seek. I hide in his sisters closet and my foot slide into her pumps while I was standing in the corner. It felt so amazing I had to put the other one on. I was so excited that I didn't even know he opened the door. Needless to say I hide in there lots more and with him joining me.

[NicoleScott]

I dressed the first time because I had the desire and the opportunity, but why I had the desire is a very hard question to answer.
Here's an easier one:
Q: Why did I crossdress the second time?
A: The first time.

[Princess_Andria]

i remember it like it was yesterday,i was 12-3 i went to the bathroom to do a number 1 lol and in the basket i saw a pair of my mums tights/pantyhose (i had always had a huge fascination for women in tights growing up). i locked the door and tired them on, they were a sheer brown or maybe off black? hard color to explain but thats how it all started :)

[chrissietoo]

Hi,

I don't know what made me want to dress, but when I was ten I asked my mom if I could be a girl for Halloween, and she made me a great outfit with a purse and hat and everything. I felt wonderful! I don't remember 'urges' before then, but I do know I used to love to sit next to certain girls and imitate their beautiful writing and stuff. So I admired them and wanted to be like that.

:)

[Daphne Renee]

i dont know what if anything made me. I have been since an early age. I guess it was just curiosity .. Now I just enjoy it.

[Roxylust]

I remember having this huge obsession with panties, I always did laundry in the house and my sister had a pair of cuteeeee bootyshorts that were baby blue. I tried them on and noticed that I didint look half bad in girls underwear and that I had alittle more of an ass then my sis ha. It was all downhill from there :O

[lorrieanne]

I was 11 and was intrigued by sisters panties. I tried on a pair when alone and WOW! what a wonderful feeling. Wish mens undies were as comfortable. I wore them whenever I could. I wish I was able to dress more often but situations didn't allow it.

Lorrieanne

[NathalieX66]

The word "made" is not the appropriate word.
I've discovered through my lifetime that I am a crossdresser, transgender by default.
Yes, I may have my fetishes, but being a woman in public has a very different feeling.....I call it being me.

[Alisa]

I had a crush on my best friends older sister... His mother and sister would dress him up in pretty outfits and I was soooo envious of the attention he got from the sister that I just had to dress too.

[darla_g]

i am sure it was a sense of curiosity and since it was so forbidden for a young boy to put on girls things ..........

[Bree-asaurus]

I think the first time must have been when I was around 5-7 and I wanted to be a girl for halloween. I don't really remember that far back... my mom told me about it more recently.

But I have memories of wishing I was a girl throughout my childhood... wearing women's cloths when I was younger was just a way to express myself as I denied myself of that in every other way possible.

It took 25 years, but I finally realized I was never really crossdressing in the first place ;)

[BLUE ORCHID]

Hi Dani, I guess it all started when my mom dressed me in a little white receving gown wheh they brought me home from the hospital.

[Ashley Jade]

I've known that I'm bisexual since I was about 12 or 13. I started getting more curious as to what it would be like to be a woman, and I started trying on some of my moms dresses and stuff. The rest, as they say, is history.

[shyselina]

I have know idea I was just drawn too it. Always felt like these are the clothes I was suppose to wear. Started when I was 4 or 5.

[STACY B]

Hey I bet you wont put that on ?? Ohhhhh realy !!!

[KandisTX]

I was possessed by the Spirit of Divine, and Harvey Firestein (his play Torch Song Trilogy had JUST come out on Broadway).

[RachelX]

I had always wanted to dress in girls clothes, for as far back as I can remember. Lack of opportunity and fear of discovery kept me from dressing in my sister's clothes until I was ten.
"What made me crossdress for the first time?". I would have to say the fact that I could was the reason.

[ashlee chiffon]

Started when 5 or 6...Mommies undies...would sneak them and go into the bathroom and put them on...I remember my first tight black skirt that I found around 8 or 9...wore it to bed even! Early compulsions to dress were overwhelming! Like RachelX, fear of discovery kept me back, but the inner need to dress compelled me to find moments to do so. Would love to stay at Granny's about the same early years as she had a vintage white satin nightgown with lace all over I would sneak and wear...felt sooo wonderful, until I slept walked one night and she saw me and laughed..scared me and I begged her not to tell Mom and Dad...OMG...was so traumatic to be caught!

[charlene#2]

thinking back,i remember playing strip poker with a buddy of mine and his three sisters.about 13 yrs old.losing the hand that i had to give up my underwear and feeling embaressed as hell,i took a pair of nylon panties that one of the sisters had lost earlier,and put them on, i never knew that just the act of sliding a pair of panties on could make so much of a difference,from then on i wore panties when ever i could.

[SusanQ]

I was 5 or 6 at the time. We had a stepchild living with us, to keep me company (this was before my brother was born). We were alone in the house playing and somehow she suggested that I put on her panties and slip. It sounded like fun, she promised to tell no one, so I did it. It felt wonderful, and I've been wearing female articles ever since.

[Dawna Ellen Bays]

I think the seed was planted by an older cousin who wore shiny pantyhose and boots with side zippers. She would often leave the boots laying around, and I seized every opportunity to sneak away and try them on. I was so young that they came up to my hips. I got busted by her every time. As the years passed and I became very interested in girls, I guess part of me was so attracted to the way they dressed and acted and moved that I decided to experiment (badly) with makeup. Imagine my fear when I found that mascara isn't easy to take off! When I was 13 in the late 70s, I found a cache of Cosmopolitan magazines that set me reeling. I tore out so many pages of women in sexy fashions and makeup with sky-high heels and kept them hidden for years!

Believe it or not, it wasn't until the last day of high school that I realized "what I was." I had procured one of those "Letters to Penthouse"-type magazines and read two stories that ended up defining me. The first was a story about a guy who gets dolled up by his female roommates, but the one that really got me going was about a guy who would dress as a high-class hooker, walk the street in his neighborhood, and eventually get "picked up" in a car by his wife (who herself dressed as a man for the occasion). When he described his perfect make up, towering heels, and "slipping in to my tight sheath," my inner voice actually said "Holy crap...I'm a transvestite!" And I was FINE with that assessment...

[Chris100]

Guess I must have been about 13 ish. I had a very sheltered upbringing! I would rush home from school at lunchtime, when my parents were out and try on my Mum's panties and stockings. Loved the erotic feelings but wasn't able to indulge more fully until much later in life.

Christine

:daydreaming:

[Nicola2876]

First time ever was dessing in dresses for fun at age 3 or 4 then found some panties at about 6 and had to wear them. At about 11 i tried my mums tan tights on and that really kicked things off

[janet p]

It started with my friend and I wearing his moms dresses to sneak into the girls camp to spy on them. Don't know if he kept it up after we moved away but I still do.

[Lorna]

I didn't have any sisters or brothers. When I was about 13 I started taking an interest in the girls I saw around me and was fascinated by their clothes especially stockings and skirts. I wondered what it felt like to wear them. At about that time, my grandmother, who lived with us, died. This meant that I was alone in the house more often. The only female clothes to which I had access were my mothers and I found some old stockings and a skirt and tried them on. I loved the feeling of the nylons on my legs but realised I needed something to hold them up properly. In fact, what really intrigued me was what it must be like to have one's legs tightly encased in nylons right up above the knees. What would it feel like to walk in stockings? What would happen when one sat down in them? I found an old, pink Gossard girdle that wasn't a very tight fit on me but by wearing my trouser belt to help keep it in place, I was able to experience stockings and suspenders under a skirt for the first time. From that day on, I watched to girls as i walked to school, observing carefully how they moved, stood and sat.....and knowing a little of how they must feel in their clothes. Slips, shows, bras, panties, etc, all came later as I widened my knowledge and experience and, eventually, was able to acquire clothes of my own. Still to this day - over fifty years later - there is a thrill to putting on the clothes and feeling those same sensations.

[muzzy]

I have 3 sisters and wondered what it would be like to be a woman for a day so the first step was to try out there clothes and it was an amazing experience of exhilleration.I still do wonder what it would be like to be a woman for the day as I have the perfect body for lingerie and panties xoxo

[LoriFlores]

I had always felt left out when seeing girls at school and church get to wear pretty clothing. Finally one day I was home alone and it dawned on me that my sisters clothing, including her tutu from a firgure skating show, was available for me to wear. I ran to her room, pulled on her tutu and the rest is history... :battingeyelashes:

[Alice Torn]

Early teens, tried on sisters and moms stuff. Quit for many years. Early fifties bought first dress, then hose, bra, wig, heels, mostly at thrift stores. Had to order size 16 heels on internet, at Snaz 75. One thing i have noticed! No one here seems to have wanted to try on jeans!! Its always nylons, shoes, bras, dresses, skirts!!

[Sarah V]

As a 6 year old kid watching Cathy Rigby perform as Peter Pan in the national touring production of the show when it came to my home town. About that time, my mom alwasy washed out her pantyhose in the bathroom and laid them on the towel bar to dry. One day as I was taking my bath in the tub looking up at them, and remembering Cathy Riby in her costume, something came over me to try my mom's pantyhose on. Down hill from there ever since and loving every minute of it over the last 40 yrs. Once retired from my job in another 30 months, I plan to get a bit more serious about my feminine activities that I enjoy and make them more apart of my everyday retired life.

[larry]

Silk,I guess you have control on what makes me laugh.
"And then the next day I quickly broke my promise to myself."

Hehehe

[JerriSC]

I tried on my sister's clothes....moved on to my mom's stuff ( she had heels) a little later. The rest is history.

[Nichola]

Playing mums & dads with my sister at just six years old. She suggested I be the mum & helped me slip into one of her skirts.....I loved it. It just flicked a switch in me & I've never been the same since.

[Ari333]

curiosity I guess made me do it the 1st time, but as soon as I learned the feel of silky undies I was hooked. even very young I had a love for stockings and heels. moms things were the starting point, but later on as I progressed, her heels just weren't high enough and her clothing not sexy (****ty?) enough! I also remember them keeping an old metal wardobe thingie in my room with old clothes in it, mostly moms, soon I thought of those things as mine! I still remember the formal elbow length gloves she kept in it that she rarely if ever wore. I can remember now getting caught wearing an aunt's things who lived w/ us briefly when I was no more than 5 or 6 a couple of times. she had a pair of leather gloves I loved, and my leather fetish was born! oh, and later, early teens, I had a male cousin 3 yrs older. of course he didn't discourage my crossdressing since he also did! and talk about bold: his mom loved heels and mine loved flats, so while they were working during summer, we'd swap pairs of shoes (he lived 2 blocks away) and get them back in place before they got off work, young cd genius at work! a few yrs later he got busted w/ a stash of pilfered undies and shoes, mostly my moms! but he didn't rat me out, I felt great sympathy for him cause he was confronted by both parents. :sad:

[CONSUELO]

Is there a pattern among the replies. I think that I do notice one thing; respondents mention that they dress early, at around 5 or 6, or they mention that they became curious at around the age of the onset of puberty. For me it was at the age of about 5 when my sisters dressed me in my aunt's corset as they thought it would be a great lark. Well, I can still remember the feelings and the sensation and the look of that corset and from then on I was hooked on shiny underwear and tight fitting corsets. stockings, everything. I would dress up at every opportunity when left alone and I explored every underwear drawer in the house. I was discovered on two occasions and that slowed me down for about a day or so and then I was back at it. I loved watching my sisters dress to go out and the rituals of dressing and putting on makeup. It seemed so intriguing and so much more fun than the standard male dressing rituals. I also notice that several respondents mention being dressed by sisters or by close relatives. Question is, did the dressing unlock something that was there already or did it act to propel a malleable early sexuality along a particular path. Anyway, I found this thread to be fascinating and it reminded me of the huge feelings of excitement as I discovered new clothes and new ways to wear them and the wonderful sexual feelings that came as I did that. Those were such wonderful times.

[ArleneRaquel]

At about the age of eight the opportunity arose as no when else was home.

[LeotardMan]

I think for me it was my mom and working out with her was the big thing. I remember I used to exercise with her and we did exercise videos mostly Jane Fonda and Kathy Smith, and my mom would ALWAYS exercise in Leotard and I so much wanted to dress like her or like Jane Fonda. When I was 12 I tried on one of her leotards and it was heaven!! I remember for a while I would come home from school dress in her leotards and pretend to be Jane Fonda and leading a class. Going through her workout clothes was like a treasure she had leotards for home and the gym and I loved her gym leotards because they were VERY SEXY. I got busted a few times but over the past few years my mom has accepted my crossdressing.

Geoff

[lny2ne]

I was only 5, My mother use to keep a rag bag in the basement where we played (It was 1959 rags were sold to a rag man who came around every week) I got curious and started trying on my mom's cloths in that bag, I loved it. Then I started playing dress up with my sister, she did not want to play after a while and after 63 years I'm still playing!:heehee:

[ArleneRaquel]

The opportunity arose and I took it, no one else was home and some of my mother's clothes were just hanging there. My life hasn't been the same since circa 1956.

[Jenniferathome]

It was my genetic code and nothing else.

[PrettyFlowingGown]

I just loved mums wardrobe, and watching her in her pretty nightgowns when I was about 4 0r 5. I remember wearing them and they were 5 times too big for me......I could'nt wait til i was older so they could fit me better.

[tonidouglas]

I donot really why but I seem to always gravitate towards moms clothes when I was about 5 or 6 I use to try on her hose at first then her body briefers and hose it was so exciting

[Beth Mays]

The Devil made me do it!

[suchacutie]

Age 55. My wife and I were just joking around as she tidied her lingerie drawer.

Suddenly we weren't joking anymore. Within 48 hours Tina was born, had an e-mail address, and we were curious as heck about who she was.

The genie never got put back into the bottle.

[Tina B.]

Why did I put on that first article of womens clothing, well I just don't know why, but I can tell the story of how it came about. I was 6, told it was time for my evening bath, I went into the bathroom, closed the door, and found my big sisters nylon slip, hanging on the back of the bathroom door, it mocked me, hanging there all shinny and bright white, and silky feeling. Well there I was, there it was, and look, there is a lock on this door, so no one will know, the next thing I know, that silly slip was off the hook, and in my hands, I trembled. Knowing What I was about to do was wrong, and I just didn't care, that slip was daring me now, to just put it on, well my big brother taught me to never refuse a dare not if your a real man, so I took that dare and put it on. It felt better than anything I remember wearing before, or since, I felt an inter peace, as if this should have been mine. Well I was in that hamper, looking for what else could make me feel this good, I found a bra, a garter belt, and nylons, a griddle, and a skirt and blouse, but most of it was to big, but that darn slip stayed on nicely. Before I realized where the time went, someone was beating on the door, saying how long are you going to be in there, I need in, so I splashed a little water on me, put all away, and got out alive. After that day, no one ever had to tell me twice, it was bath time, I became the cleanest little boy around, bath time was good. After the first night, I found time to wash, as well as play at bath time, so it all worked out pretty well.
Tina B.

[cathie pantyhose]

for me it was a love of pantyhose that grew from there. As a cyclist as well, the smooth legs made them look even better. Had a gg tell me my legs were betetr than hers and the rest was histroy. I decided I wanted to see what they looked like in a pair of heels and there was no turning back from that point

[Janine cd]

I lov ed my mother's dresses and undergarments. I wished that I could wear her high-heeled shoes as well, but my feet were too large for them. I spent a couple of years experimenting with a feminine persona based upon wearing her clothes.

[NathalieX66]

The fact that mens/boys wardrobe sucks. I must have been about 5 or 6 when I figured this out.
Now I live & go as I want.

[GinaMarie]

My memory of my first time crossdressing, as far as I can remember, is when I was eight or nine. I tried on one of my mom's sports bras and something else of hers. What else do I remember about the experience? Not much else.

[sherib]

Nothing made mw start it was by accident when I was in my mother's closet and I tried on her nylons and heels. That was it.

[Kimberlyfaye]

For me it never started out as me wanting to look or feel feminine. I just loved the clothes. I have no brothers, or more importantly for me, no sisters :-( I think when it first started I was wandering around the house exploring when I saw some of mums clothes. I wanted to try them. I remember thinking of playing pretend and also it was a slight sexual thrill. "This is sexy and a little bit naughty" I would think to myself. Anyway, I tried on more each time I had the opportunity. My favourite items were actually the bras. I must have been doing this for three or four years, with a few near misses of being caught. Eventually I got caught but it never stopped me. It has since progresse d over the years and never left me. Yet now I find myself wanting to look and feel feminine rather than how I started. I think that's a good thing.

[phylisanne]

my first time was when i put on my mothers stockings and that was the beginning of many trials and tribulations in the wonderful world of womens clothes,

[DonnaG]

I grew up in the 50's. Nothing was better than Sunday morning when Mom would get dressed for church. She never had a problem with me watching her dress. Lacy panties and bras, OBG and nylons, always the most beutiful slips and frilly dresses. And I'll never forget the sound of her heels on the marble floor. And watching all the other ladies walking to their pews. Befor going off to school I think I wore her clothes more than she did. I know she found my stash several times but never said anything to me. I still love dressing like Donna Reed and Mrs. Cleaver.

[SaraTV]

I think I started from the bottom (stockings and heels) around 8 or 9, when no one was around the house; and worked my way up (panties, bras, makeup, etc.).

I guess I thought it was fascinating that women could change so many things about themselves without so little effort (yeah right) and I just wanted to try.

[Melody Phillips]

I was curious. I was in my early years (10 - 15) and it (the crossdressing urge) seemed to call to me. Girl clothes always looked so nice compared to mine.

[Desiree2bababe]

The love of silk upon my skin and the need for attention were the most likely causes.

[silkiehosewearer]

Not sure really... Just had the urge to try on my mom's pantyhose and when I got the chance I took it. Same with my aunt's pantyhose as well. After which I was hooked from then on.

[JustAlex]

I wish I could remember how it started. My oldest memories are of me playing with mom's panties and wearing a pillow case as a dress when I was about 5. But that couldn't have been a first time, I don't remember any of those things as something special. it's like I did it because I was used to.
I always kept it a secret. I played with my mom's panties when nobody was looking. I'm sure my mother knows...

Eventually it got out of control (or not...) and I remember wearing panties and bras and slips and pantyhose and nightgowns as a teen. And I remember how things were different at that time because sex was a part of it.

But I can't remember one event that I could say was a first. Not at the beginning, not a turning point from my innocent childhood to my wild teenages, not a turning point to my life as a self accepted crossdresser.

[AlexisRaeMoon]

Jeez...did we all start between 5 and 8? I remember having a friend in kindergarten who would always try on dresses in the dress-up clothes bin, and found it fascinating, but was way to chicken to do it myself - in front of everyone (some things never change...). I fantasized for years about having a closet full of girls clothes, and would sometimes stuff socks in my shirt to see what it felt like to have breasts. But it wasn't until I was jr. high age that my parents started leaving my home alone. I discovered that my mom's heels fit me, and I was hooked. Suddenly, I never wanted to go to the store with them anymore! So, I was always interested, but it was definitely the shoes that hooked me.

[Laura'sCloud]

Don't really remember the exact first time, i know several times from my early teens trying on my sisters shoes and heels because they were different, i also got jealous of not being join in with my sisters when they were doing each others make-up and hair. Then just after i turned 15 when i first started having extended free time in the house with no-one else there, i started trying their on clothes and they just felt right on me.

[Barbara Jo]

I grew up in the '50s and had a 4 years older (and younger) sister.
I simply wondered at a very early age what it felt like to wear all those feminine, female clothes of the era.
So I started to try them on.... starting with panties and slips, etc. Then, I quickly progressed to trying on everthing else.

[Rebecca Star]

Great thread Dani :)

The earlist memory I have is my sister (12 years older), dressing me up when I was about 4 and taking me shopping of all things. Mum was ok; it continued till I was about 5. If my dad had known he would have flipped his lid. When I was around 7 sister when OS and I used play in her room for hours. Although I've never felt like I was a boy in a girls body, I have felt different to other boys. I suppose, the CD'ing seriously commenced when I hit puberty. Like most I've gone through guilt and throwing everything out, more times that I care to remember. But, now I've accepted who I am and screw everyone else's opinions, I'm certainly a lot happier.

[christinac]

I've always admired ladies clothing, but my very first crossdressing experience was the result of a truth or dare type stunt. I lost the bet and wore a hot pink body suit, similar to the black one that Olivia Newton John wore in Grease, with pink socks and pink running shoes to a club we used to haunt. I think I posted about it the other day, but it was the same pink suit I was wearing when the bouncer mistook me for a lady and stopped me before going into the mens room.

[Brokenflag]

I remember when I was younger my sister dressed me up in her dance outfits a few times and I loved it!

[Liara]

I love being on a forum where this topic is normal. I started when I was around 4 or 5 years old when my older sister would make me her little sister for dress up. Fast forward to Jr. High school and i would dress every time I was home alone and I would dress in my room a lot by myself late at night. I really wish at times I could dress 24/7.

[Stacie_Miller_CCD]

My first cd experiences were when I was about 10. Found mom's lingerie, tried it on, got horny. Sucked when she found it in one of my boxes. There was one time I tried a whole outfit on, panties, nylons, bra, dress and makeup. Just lipstick. Oh, and heels! Girl's best friend! Anyways,I did that quite a bit, then when I was 20 I dressed for my "bf". He was my best friend and the only guy I had sexual interaction with. But one day he came over, we did our usual thing, me go down on him, afterwards I told him I had a surprise. Went to my bedroom and put on stockings heels and a spaghetti strap shirt, let's just say my mouth was busy all night long!!

[Rebecca Star]

The fact that mens/boys wardrobe sucks.

It's not actually a fact, it's your opinion. I love my boy clothes (definitely not drab) just as much as I adore Rebecca's wardrobe too.

[CassieV]

I know I played dress up in the elementary school days, but I'd have to say things really started when I was 14. Found some panties and pantyhose in the dresser in my parents' room and never looked back.

[Antoinette]

My mom asked me this and I ask myself this sometimes and I honestly do not know. It just came naturally

[heatherdress]

My wife suggested that I CD. It was for fun and for experience. She encouraged it - buys shoes, clotes and makeup.

[connie johnson]

When I was about 9 or 10 years old, my mother had a job where she worked from home packaging pantie hose. This was 1970, I guess before all the imported machine packaging processes. Any way, I felt the hose and was intrigued by them. I took a pair and put them on and they felt wonderful, I loved them. I have been hooked on pantie hose and thigh highs ever since. I then started borrowing my older sisters clothes when I was home alone. I just like the way the clothes feel on my body. I like the satin and nylon kind of stuff. I don't wear any cotton women's clothing, I can get that feeling wearing my guy clothing. I had to take several years off as i got into my late teens early twenty's. One I met my wife and got married we tried the dressing up for fun thing, I told her I really liked it. She is more than OK with my cross dressing and supportive of it. Too bad the kids are back from school and I don't get the chance very much right now.

[cassandra54]

i guess technically the first time i dressed, because my older sisters thought it would be fun to dress me as a girl. i was five or six. i guess i was always curious after that. later on in life, i dressed for what you would call fetish reasons.

however, once i started to dress as a woman out of the bedroom, it was about three years ago and that was a whole new experience. i wanted to do it more and i wanted to look as close to a woman as possible.

it's been just awesome

[curiousby]

I am a bi-sexual guy. I remember when I was a very young boy (I think about 5 or 6) I had to wear some of my sisters panties because all my underwear was in the dirty clothes hamper. I can hardly remember how they felt but they did feel good. I am not sure why I did not continue trying them on. One time when I was married I dressed in my wife's underwear and she freaked. I never did that again with her.

About a month ago I bought some panties and a nightgown. When I put them on I could hardly believe how they made me feel. From there on I have been wearing nothing but panties. They feel so wonderful. I have not dressed any further then panties and nightgowns but I am thinking about going further in the next few months.

[tonidouglas]

your so lucky wishmine would encourage me

My wife suggested that I CD. It was for fun and for experience. She encouraged it - buys shoes, clotes and makeup.

[AlexisRaeMoon]

You know, I have to thank you all for you candidness in this thread. I used to feel really creepy about that fact that I used to raid mom's wardrobe. Somehow, I had it in my mind that if I was buying my own clothes it would be less weird, but that wearing mom's clothes was just another level of wrong. Seeing that so many here also did that same thing in their early teens...well, that's all I can say is it makes me feel less alone. I mean, honestly, as a pre-teen boy in the '80's, what other option was there? It's not like I was going to walk into K-mart with my allowance and buy a pair of 4" pumps and a lace bra! "Oh, it's for my girlfriend." At least now I can pretend I'm shopping for my wife.:battingeyelashes:

[Mel_CD]

I thought I was so weird and strange and "pyscho" as my brother & mom called me when discovered. Now after reading endless stories in this thread and so many other threads and so many other sites, its seems so .... ordinary now! Seems almost trivial now among so many similar histories.

I grew up in the early 1950's when all "decent & proper" girls wore nice lovely very fem outfits. They wore these everywhere, everyday -- at home, school, even while playing, even at amusement parks and carnivals. Typical of all boys, I was always fascinated and aroused by peeking at anything forbidden and taboo. Seeing any kind of under garments of any kind would give me endless thrills. I especially love those very windy days when there was lots of opportunities to see forbidden sights, when the wind would lift up all those wide garments revealing "hidden treasures". Of course the girls would scream loudly and fling their arms down with a loud slapping noise slapping down their garments trying to cover themselves decently. I think they were well aware of what they are doing and probably was flirting and teasing us and secretly loving the attention! It was no end of thrills for me when seeing such actions and scenes. I would get so fustrated and impatient waiting for "natural accidents" to happen to these sweet pretty girls in their lovely outfits. I would get so fustrated that I began thinking -- if I can't see it for real why dont I try to act it out for myself and PRETEND to be that sweet shy innocent girl myself and wear those things for myself and act out the scene for myself?

I always was a very naughty boy whenever my mom took me shopping. I would do all sorts of terrible things at the stores, taking articles and throwing them to the floor just for fun and making life absolute hell for mom and anyone nearby. Finally mom lock me in at her bedroom so she could go shopping in peace. It was a large bedroom, not a small confined closet, so I was able to roam about all over the bedroom. It was during those hours that I discovered her garments, the wide full flared skirts, and petticoats. At last! I was able to act out my fondest fantasy. What a thrill when I put on the petticoats and her full skirt that 1st time and pretended to be that shy teen girl! I was disappointed that their was no fan to similate a nice windy air flow to lift my skirt so I twriled around to make them fly out getting dizzy in the process! Their was a full length mirror, so I can see myself. What I see in my mind when looking at the mirror is not myself but a sweet shy innocent girl wearing such a pretty dress. I would lift it pretending that the wind was blowing it up, exposing the petticoats and then squeal in embarssment and would get that same arousal as I do when I see those petticoats revealed in other girls for real.

That was the beginning of a long long history of dressing up that lasted over 50 years now!! I now have a TG/CD club where I can store all the gowns that I have collected over the years along with several good size blower fans. Whenever I get the urge, I would go to the club after hours and set up the fans and dress up in a lovely full ball gown or prom gown or bride-maid gown -- and have a long session of acting out the carnival, amusement park fun-house skirt blowing scene for hours at a time. I think I get the same "highs" as others get from drugs!

[Raava]

The first time I CD'd was when I was about 14 or so. I brought my laundry basket up stairs and it happened to have some of my sisters clothing mixed in, one thing led to another and I was trying on her clothes out of curiosity. That continued on and off for a while until now (I'm 20) I'm just beginning to make preparations to start up my own wardrobe and dive right in. As of now I'm still in the nitty-gritty phase of figuring out how to measure myself and what clothing to buy, but soon enough I hope to have my first outfit, which I'm in the process of getting together.

[Rebecca W.]

What made me crossdress for the first time was to find out how the satin skirt felt sliding up my legs:o while wearing pantyhose. Oh my, I am hooked for life.:o

[fuzzysweatergirl]

I have always had an attraction to women's sweaters, as far back as I can remember but didn't get the nerve to try one on until I was about 13. Noticed my mom had a few nice sweaters in her closet so one day after school I decided to try one on before she came home. Put on a thick wool cardigan and just loved the feel of the sweater actually on my body. I was hooked at this point and so the next day I went and tried on a thick wool crew neck sweater and eventually as time went on tried on all of the ones she had. Then a few years later I got some of my own sweaters and after awhile I became curious about other pieces of clothing since I felt like I needed something to go with the sweaters. Now I have been slowly exploring other kinds of clothing and love every minute of it.

[CONSUELO]

This is a commonly asked question but the answers are so varied and never boring. I was dressed by my three sisters as a joke. I was around five years old at the time. They put me in an old fashioned long line corset that belonged to an aunt. From then on I would put on their underwear as often as I could. I found that a combination of the look and feel was exciting. I would also try lipstick and I was fascinated by the feminine dressing ritual and always loved imitating it. My father was always at work so the household was dominated by women. I also had lots of aunts and they were such strong personalities that I was always attracted to them. I later found my corset wearing aunt's lovely long nightdresses and I would love to put them on and look at myself in the mirror. Of course before puberty arrives the body is so androgynous. No hair to worry about and no emissions to speak of.