At what age did you start crossdressing?

[Jessica Hannah]

I actually had a dream about dressing up like a girl at around 4 or 5, but the opportunity to dress came when I was about 7 years old and home from school.

[Staci]

when I was very young(3-5) and I spend every moment with my mother, I was not allow to play with other kids and my parents were seprated. My days with my mother consisted of going to the beauty salon 2 or 3 times a week so she could get a roller set, which would take a couple hours in which all the women and girls also get their hair set, everyone but me. Each week she would go clothes shopping. At home she was always setting and doing her hair often making me watch. Each night she come to bed in a long silk nightgown and her hair set in rollers. Two things I dreamed of where mother dressing me as a girl and taking me to the beauty salon to have my hair set just like the other girls and put on a long silky pink nightgrown and setting my hair in rollers and going to bed.
No surprise went I went into my mother's drawer and started setting my hair in rollers. I would take every chance I could to get my hair in rollers and my hair was set, it was time for bras,panties, nightgowns, dresses, skirts, the sky was the limit. Once my hair was set I felt like woman and I felt so free.

[Eric Anthony]

I started around 5 or 6 when I first tried on my mothers pany hose, bra and a sun dress. It really felt good.

[DonnaT]

Hi Eric, aboard.

[Sophie Scot]

I started at 10 yo at my Grans,I used to stay there at the weekends,and during school holidays,I guess curiosity got better of me,I then began wearing my mothers clothes too,and can still remember every outfit I wore in those days

[Martina]

I ticked 10-11 because it was the age when I intentionally put on female clothes because I felt a desire to do so. Before that I had worn girls clothes for fun or experimentation and also through necessity. I was given a nighty and panty set to wear when I stayed with an aunt when I was about 8 and I also tried on a pair of my cousins frilly tennis panties just to see what it was like. It was wonderful. That's why I started to wear girls clothes for pleasure and comfort later on.

[Anne Geraux]

I started sneaking around the neighborhood and stealing underwear off drying lines.
I was scared silly.

It was so hot

i came for the first time wearing two girdles and three bras all piled on top of each other.

[LyndaLoves]

dressing on my own started around 12 years old but
When I was 5 or 6 my parents forgot my PJs when we went to the cabin
I wore my sister's nightie, I remember I loved it and it felt right
Don't know for sure but I probably wanted to go to bed early the next nite

Lynda

[Anne Geraux]

ogh egh wooohie girlly so lucky

[ArleneMcCarthy]

I voted 6-7, though it may have been as late as the age of eight. I have never outgrown it and now I loving living/dressing as a woman 24/7 !

[Anne Geraux]

I stand corrected...
My mum dressed me in my sisters night gowns until I was 6 and you could say I got on the mothers knee

[BrianaGiGi]

For Me, it was when I was 4. I specifically remember the first time - right after church. O_O We got home, mom was making lunch, and I decided to try on all her pantyhose. She found me in the corner of her bedroom in a pile of her pantyhose with one leg in one pair and one in another. Pretty silly looking I'm sure...LOL. She thought it was cute; my father was not happy AT ALL. Still, I never stopped after that. My mom was fine with it and very understanding and supportive. She even set aside an old cabinet that she would keep stocked for me with her "old stuff" so that I wouldn't get into her new/good stuff.

~~~~~~~~~~~~~~~~~~~~~

Briana GiGi

[Allie Nichole]

before i have memories i have stories from my mother of crossdressing, i posted that in the first thing you tryed on thread.

My earliest memorie is about 3 years old, my moms shoes, and at 7 my sisters dress just felt right.

[Anne Geraux]

Allie,

Seems like you were lucky to have a caring and open mined Mum.

[Paulette]

So when did you first put on an item of clothing clearly only for someone of the opposite gender?

Not quite sure what you're asking, but first I'll assume that you mean dressing as a girl in order to attract or please a boy.

When young I repressed my crossdressing for many years, including during the marine corps years. Then I was very actively seduced by a boy I met in Jr College. I wasn't particularly attracted to him, but at that age anything that works, works. I dressed for him once, but it was at his request and wasn't all that satisfactory for me. Yes, I got off, but only because of the physical sensation and not because he excited me. I excited me, and that was sufficient. I broke up with him after an argument about whether one had the right to manipulate others for one's own purposes - something he did constantly and I objected to on moral/ethical grounds.

In the interests of full disclosure, more recently, some 45 years later, I asked a young man if I could kiss him. It was in a 25-person SF group of hot-tubbers where polyamory was the rule. I wasn't known to be a crossdresser to anyone there except my girlfriend (now my wife), but this one asian man suddenly smelled right. So I asked, he accepted, and we kissed right there in the tub with everyone around us. Full body nakedness and tongues too. It turned out that he was heavily into garlic that night, so that's where it ended, though it took a while for my wife to accept that I really wasn't very gay and hadn't been holding out on her.

Within the year I'd moved in with and married my girlfriend. She has always been supported of my CD, and encourages me to dress and would support me if I went femme full time. Like at least one SO here, she was bi-sexual, so my CD actually fulfilled her interests rather rather nicely.

Now I rarely dress, and only for bed, and for a while the desire for either was almost gone. (Raven Candera(?) speaks of happily married CDs finding that their CD interest diminish, and they find that they have to explore new kinks to get their old kicks.) However, both the urge to cross dress seems almost identical to and simultaneous with the urge to make love, and I think that for a while that may be a couple times a week -- quite surprising to me at age 73, but I'm not complaining.

I hope this has been interesting.

cheers,