When did you first crossdress?

I was just reading through several of the many replies to this question and it reminded me of how wonderful it felt when I discovered that i loved to dress up in feminine clothing. It was a mixture of heady excitement with a strong feeling that this somehow was a part of one's self. Along with all of the dressing I also remember being fascinated by women and their lovely clothing and also reading about a man who underwent sex change surgery. The latter story just fascinated me so much.

I noticed the analysis done by one of the readers that pointed out that the majority of us cross dressers began this journey between the ages of 5 and 12. It is as if we just found our true selves at that age. Sadly, society's mores and restrictions have landed many of us with guilt and frustration and prevented many of us from truly flowering. I do hope it is much better for young cross dressers today.

You make a poignant point about how wonderful it felt to wear women's clothes for the first time. What a special feeling!

About 15 years ago. I wore a blouse and Capri pants. Had a bra and panties on. No wig. I have a wig just can't get to that stage yet.

Wow...my first time was so long ago I really couldn't pinpoint an age. I remember trying on some pantyhose when I was really little...by age 9 I had managed to acquire a decent sized stash of them. Started branching out into other garments around age 11.

After reading through a lot of the comments on here I find it interesting that, to a lot of society, this is viewed as a choice or a sexual deviation. Most of the stories here indicate that the onset of crossdressing happened during the prepubescent stage. Kind of throws a wrench into the aforementioned societal perception. I have always felt like this was not a choice, but something that developed naturally in me for reasons I don't understand. The posts here seem to reinforce that feeling. I find it interesting.

The first vivid memory of wearing something I have is around 12/14 I found out a cardboard box full of brand-new lingerie (that a friend of the family whom used to own a lingerie shop offered around Christmas and such) and I'd run that box from top to bottom. However I'd previously browse through my mom's cloths and I really wanted to try them on specially shoes, never did (until later and barely could fit them) probably due to fear of getting in troubles.

It's interesting that everybody agrees in childhood memories.
By my side I was may be 6 or 7 and I like to touch my mom's panties and bra. Then being 11 I enjoy getting my sister's, older 6 years, Ra and panties and wear them sometimes but then at 15 I had my first heterosexual experience that last like 3 years, then several girlfriends and after my wife, so sexual activity was enough to put to sleep my femine side.
It was up to my thirties that that desire wakes up again. Just for a joke I start wearing my wife small thongs, that I bought for her, and I like the way I look in the mirror. I have a nice femine butt. But then in some swinger activity, I notice that a lot of guys like my butt wearing panties. Just around 10 years ago i fulfill my desire to completely dress and I enjoyed a lot, since then, any chance I have I do it full and is really pleasureble.

8-9 or 10, don't remember an exact date but was well before puberty. Something I have thought about a million times, why? And what made it stay? It's just an enigma to me.

Some years ago my then wife dressed me. A GF a few years ago then 8? months ago I got into it big time.
Many dresses, 4 bras and 3 wigs. (not keen on the wigs)

Would have to go back to when I was a teenager. I was home alone at times when my grandparents were out at the doctors and doing shopping. I would look in the closet for things to wear. My grandmother had enough clothes to start her own K-Mart so it was easy to search in spots where they wouldn't even notice that I may have pulled something out. I found a swimsuit and a shirt/skirt combo that both fit me and felt good. Most of the time, I was able to put it all back without them noticing. Especially in the closet where my grandmother had bags of clothes, there was no way she would notice anything.

I remember trying on a pair of my mum's knee-high platform boots when I must have been about ten or eleven. Also trying her lipstick on which fascinated me (all secretly of course).

Makeup and shoes are still my thing as well.

When i was 7 there was one of my mothers bras in the bottom of a laundry basket, i think it was left in there and forgotten about, i tried it on and it was awesome. I ended up hiding it in my bedroom for about 3 months, wearing it occasionally. My dad caught me wearing it and scalded me and said it was wrong.
When i was about 13 i think, i was home alone once and I tried on some of my mothers clothes again it was amazing. I am now 18 and Ive been doing this since because i have no money at this time to get my own. Honestly I would love to have my own clothes.

I was a teenager. My sisters had moved out and left all sorts of clothes at home and I would try them on.
Also when a freind and his family went on vacation, I would watch there home and try on his moms clothes. She was a very classy lady and had really nice bras, panties, slips etc. Do you remember the Leggs pantyhose and the plastic egg they came in? I used these as forms.

Now I have my own bras and panties, stockings and more.

Sigh,


Randi

i started at age 6 i really was not sure what i was doing - but got a thrill

I'm not sure when I first put on my mother's panties and slip but I do remember asking why I wasn't a girl when I was four. Around seven the thought I should be a girl really hit me hard and it scared the crap out of me. Shortly after that I did put them on. I remember playing house with my younger sisters and I always played the mother and dressed the part as much as possible.

I remember playing "dress-ups" in a dress when I was about 6 or 7 but got laughed at by family so the earliest I probably actively started crossdressing would be when I used to try on my sisters shoes and dresses after school when I was about 11 or 12. She would be off at lessons or sports so I could try a range of things on.

I was probably 13 or 14, but my sister was a year older, and on occasion, was able to try on her clothes.
When she was able to try on new fashions, including makeup, I wasn't too far behind trying on her look, all while she, and mom and dad were away at the time.
The need to dress took a back step when I left home to pursue work, girls, etc, but the buzz never really left. In fact, meeting a new girl meant the opportunity to try on her clothes when she wasn't around was never far away. All these years later, while the big picture of relationships has finally dawned on me, I still look forward to the opportunity to dress in her clothes when she is not around.

3 or 4 the first time I asked my mom for a skirt. She said it was inappropriate, but understood why I was so drawn to such a pretty skirt.
She had this jewel tone purple velvet knee length skirt that I adored.
Was the early 60's, and what attracted me so much to it, was that anything that touched it (even barely) left a mark.
There was more than one morning that she went into work with tiny little hand prints on the back of her skirt.
After about the second time (after her coworkers mentioned it), she caught on and always wiped the back of her skirt as she left the house.
The first time I actually wore anything was when I was about 8 I guess. Was a white one piece bathing suit, that I found in the basement while searching boxes for something else.
From there I was pretty much hooked.

Wearing my sisters panties when I was around 13 or 14. Would take them out of the hamper
and put them on when she was gone.

I've had a feeling about this for a long while. When I was about 13 I had an awful urge to wear my sisters clothes. First I wore her boots then a skirt. Since then it had waxed and waned so to speak.

I first crossdressed when I was around 8 years old. I found a costume bin with all of my mom's old dance uniforms and old school clothes.

When I was seventeen I would switch clothes with my girlfriend at the time during intimacy.

I was 5 years old, it was Mom's pantyhose and a girdle... yes never looked back either... I knew I was addicted right there!!!

I remember wearing my sisters skirts and dresses at 4.

At -40 weeks of age I was literally wearing a woman who I can only assume was also wearing clothing. ;)

I think I was around 9 tried on my one of sister's dresses and I have been wearing a kilt for 15 years because a mini would just get weirder looks.