When did you first crossdress?

I can remember the first times I wore female attire. It was downright exhilarating! I was about 13 years old, and my older sister is about a year older than me. When no one was home, I would sneak into her room and try on her clothes. My favorite outfit was a jean skort and a tight fitting striped short sleeve t-shirt. This was a very confusing time for me. I mean, I really enjoyed this and every chance I could get to sneak into my mom's or sister's room, I would.

Converse sandals were my typical shoe choice with the skort/t-shirt combination.

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Originally Posted by Patti Remick

So I was home alone in a house filled with tons of perfectly fitting girls clothes. My father even had built a huge walk-in closet in our basement for my mother and sisters to keep there clothes in! My sisters had so much stuff - dresses, skirts, blouses, jumpers, even their old shoes! I wore their panties, tights, vests and training bras, and pantyhose. I wore almost everything of theirs that I could and by age 9 or 10 I was one of the best dressed little CDrs you could ever meet. Complete outfits head-to-toe, inside-out! And this was the 1960s and girls clothes were GIRLY.

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Wow, that sounds like heaven girl! :)

the first time i crossdressed was when i noticed my sister's laundry in the dryer. i was about 10 or so, and i had always wanted to just try girl clothes. i took out a few pairs of panties, a bra, feminine jeans, and a low cut shirt and off i went!

I honestly don't really remember the first time but it was at a very early age. I think it my have started when my Mom thought it would be cute to dress me up as a little girl for Halloween. I don't really remember the occasion but I've seen the pics.

I know most of my early dressing was at my Grandmother's house. I stayed with her while my Mom worked and she had a bunch of clothing that was her daughter's (my aunt) when she was a kid. I took the clothing for my own and my Grandmother was ok with it. This went on for quite a while (at least a couple of years) until my Mom found out and she freaked. I had to get rid of all the clothes but she let me keep one dress. Until my Mom found out, I thought it was perfectly normal for me to wear girly things. I don't think I even wore the dress she let me keep because the whole situation of me getting caught by her traumatized me and it was quite a while before I dressed again.

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Originally Posted by kinkyboots

5 or 6, mom had some clothes drying in the bathroom, I tried them on and got busted (and punished). after that parents were always checking up on me, got busted twice more later into the teens, got better at hiding. got the gay talk twice (Jesus would cry) didn't matter i was also busted with playboys, or how much i pleaded that i like women. my parents are all black and white

when i got married, my mom hugged my wife and told her she was scared i had been gay, but everything was okay now.

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In my case it was my dad telling my wife shortly before we got married (1973), "I glad you two got together, we were beginning to worry about him." Later, she asked me what did I think he meant by that. I knew exactly what he meant by that.

My first real recollection was, my Moms garter belt and stockings I was about 10 yrs old, she and dad were out, my aunt was upstairs with her Boyfriend, I put them on , I felt so girl and 'right".

I remember it so well. I was lying on my moms bed alone in that room. Reason why was probably because it was the only empty room in the flat we lived in. We were seven in our family and always some extra people visiting. I shared room with my older brother and didn't always want to be in the same room as him. But it could have been for another reason. I was probably about 6-7 years old.
My moms nightgown was on the bed. I felt the fabric with my feet and what happened in me I do not know. Electricity. I had to put it on and I did. Wow it felt good. Obviously my father came in and started to laugh a little, I think I said I was playing store. I wasn't embarrassed really, at that time I didn't see any problems with it. I don't think my father thougt of it again.
I even remember the colour of the nightgown, a bit offwhite. Made of nylon of some sort, probalby a cheap one, we were not a very wealthy family.

I was hooked after that I can tell you, and that is around 40 years ago.

I remember it like it was yesterday. I was about 13, maybe just under. I used to sneak into my mothers drawers and grab a bra and pair of panties to wear around the house when no one was home. It was an unlined white bra with a floral pattern and a blue and back thong that I fell in love with.

Right around 12-13 here,

Right around the time I started noticing girls in an amorous way, I started experimenting with their clothing. It was an on-again/off-again thing for a long time after that, episodic dressing here and there. It's funny, but I've been crossdressing for 20 years, but only in the past year or two did I start to consider myself a crossdresser.

I dont remember my first time, but I DO remember the first time I almost got caught. I was in 6th grade and my Dad almost walked in on me in my mothers bra and panties. Really scary at the time. Lol

So, am I unique here? I'm retired and really only began cross dressing a few years ago when I discovered that my wife's panties fit me perfectly and I could wear them to work. Since then I've become "addicted" to dressing and part of my closet and some of my drawers are full of wonderful women's clothing. I do love it so when I get the opportunity to have the house to myself and I can dress fully.

When I was around 5 or 6, I put on a pair of my mother's pantyhose (I didn't think much of it in terms of crossdressing). My brother told on me and I got in trouble. I never dared to wear women's clothes ever again.........until now.... ]:)

I have always had a fascination with ladies heels, stockings, lingerie. I have no sisters so it was my mothers stockings/ heels I first tried in my younger years, thru my teen years. rarely done as a big fear of being caught. Later years not very often when I was living with someone. Big fear of being caught. Now for the last 15 years I have been alone and its nice to be able to lounge around the house in stockings and heels.

I had put my first time right out of my mind as it was in a previous life when I was in the depths of separation & divorce from my first wife. She had left some clothing in the house when she left and I suprised myself by finding comfort in he clothes. None of it fitted though so it was not very pretty and I put the whole thing away until CDing burst in on me again last year and it all came flooding back. I have to say it's all much more fun this time round!

I think I was around 10, I stole pantyhose from mum's wardrobe and .......I felt in love with that. Why did I start? I have no idea. Would I start again if I get to chose? YES endless times !

Hi Suzie Q,

I think we're all-ages. as far as i can recall i was about 41 when i started. My wife was in on it, and we went shopping for me, such an exciting trip out.
i found that the thongs really don't work for me for all-day, but great for sexplay with her. I'm now wearing bikini briefs and high-leg briefs all day, home and out, and we're discussing the next step of me going CD at home. It's been long and slow, but I feel like a rush now to progress.

Thanks to Minerva Morgan for conducting an analysis of the data here. I did a very crude one some months ago but the number of responses has increased greatly since then. Just like Minerva I was surprised by the number of people who remember cross dressing at a very young age and certainly before 10 or 12; over 80%. I started very young and being "dressed" was one of my earliest memories. She may be right in her conclusions.
The surprising part of this "survey" is the small number of people who did not begin dressing until much later in life. I wonder about that.

I think I tried on my sister's dress when I was home by myself at like age 11 or so. But high heels seemed to be hardwired into me, I've been fascinated with them since I was really little.

I started wearing my sisters clothes at the age of six. Dressed in a female part in our kindergarten school play about the same age.

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Originally Posted by CONSUELO

Thanks to Minerva Morgan for conducting an analysis of the data here. I did a very crude one some months ago but the number of responses has increased greatly since then. Just like Minerva I was surprised by the number of people who remember cross dressing at a very young age and certainly before 10 or 12; over 80%. I started very young and being "dressed" was one of my earliest memories. She may be right in her conclusions.
The surprising part of this "survey" is the small number of people who did not begin dressing until much later in life. I wonder about that.

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I often wonder why we do it before puberty. Age 6 for me was really young.

I don't know, but I was at most five years of age. I recall asking my aunt, only five years older than me, why I could not wear the same pretty clothes like those that she and and other girls our ages wore. I do not recall her answer, but she let me wear one of her skirts and my grandmother's heels. I first went out in public fully dressed at age nine, at Halloween. My mother did a good job of making me look authentic in a long skirt and a peasant blouse.

Several have wondered why we found cross dressing at such a young age and well before puberty. I distinctly remember having an interest in sex and being sexually aroused at a very young age. I noticed some of my nieces and nephews showing an interest in their genitalia at a very young age also. Of course it was only the parents who were embarrassed as for the children it seemed natural. I was sexually active well before puberty and once I found soft silky lingerie I tried to dress up and obtain sexual satisfaction frequently.

I think we have a certain sexual plasticity at that age and that is why an interest in clothing and other objects can be imprinted early in life. I have read that for males this is especially so as the male genitalia are external and easily stimulated which intensifies the response.

about 11 or 12....my mom's bra and panties....

I was around 11-12 years old when I began wearing my mom's bra and panties. I was raised in a primarily female dominated environment and it seemed rather natural at the time.

Not only can I remember I was 12 years old, but I can still remember the exhilaration I felt on my way home from school. This would be the day that would change the course of my life. Forever.