What made you crossdress for the first time?

[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.