Figured I'd answer my own question! lol I guess you could call me a late bloomer. I didn't start crossdressing until a couple of years ago, all because I lost a bet with my gf. If I won, she was to dress up as a french maid for the day and clean my apartment. She thought about it and said "sure". When I asked what I had to do if she won, she said "same thing!". Well, long story short...she won, I had to go and buy a french maid outfit, a wig and heels and she did my make up. I have to admit, I looked HOT! lol Since then, we have a dress up night once a month and have even attended some fetish parties. It has definitely brought us closer together and our sex life is out of this world!!

I don't remember when. It's been some part of me for as long as I can recall, so I guess I can't really answer why, either. I do know that I started with some tights, and that progressed to nightgowns with the tights, then over time into pantyhose, and skirts and dressed with the pantyhose, and so on. I very briefly played with makeup and polishing my nails, but while they were entertaining enough, I suppose, they didn't do anything for me to speak of. I much prefer skirts, pantyhose, and high heels, and I haven't ever really seen the need to pretend to be a woman, or take on other feminine presentations, to do that. I know, I'm odd.

I started crossdressing when i was in my early teens, Every night i woul watch my mom dress in her stockings to go out to work, she was a barmaid, When she wnt out i would try her clothes on and done so ever since, i have all my own outfits now and love to be in them,

I started when i was quite young and a friend of mine decided we would dress up in his older sisters clothes. Really this experience should have put me off for life as his dad who was a big man, started going mental and demanding us to open the door when we were both dressed to the nines in stockings, panties, skirts etc. The door was locked and he was threatening us and we kept making excuses as we undressed like lightening. On opening the door we were threaten ed with all sorts if we went in her room again uninvited. Since then i have secretly tried on all kinds of clothes with great success as i have never been caught. I am now at a stage where i think i am gay and would like a boyfriend who would treat me like a girl all the time but don't know if this is ever possible. I reckon i am quite cute when dressed and am slim and slender and hope i would pass but i have never had another opinion on this and don't know. I dream of men every day of my life.

It started when I used to stay at a school mates house as when I stayed there one school holiday he bet me I would not go down for breakfast wearing a skirt, bra, panties and pantyhose of his sisters so I said your on go and get them, he came back with a pink matching bra & panties set a rather nice lemon skirt, white blouse and a pair of black pantyhose it felt rather nice wearing them, he then said lets go down for breakfast which we did his family did not batter an eyelid all they said was we did not think you would take him up on his bet, how do you like wearing his sisters clothes I said it felt rather nice wearing them then they told me Mick likes wearing them as well he normally wears them on a Sunday for the whole day would you like to wear what you have for the whole day I said yes please. The next time I stayed there I found that there for the school holiday there was enough of his sisters old clothes for me to wear a different outfit every day on the last day I was asked if I wanted to take her old clothes with me I said yes please but what will I not have anything to wear on my next visit I was told not to worry as there would be another lot of his sisters clothes I could have the use of this went on for about five years till they moved away by then I had about 30 skirts, 30 bras and about 60 pairs of panties and about 80 pairs of pantyhose

I remember sneaking into my mother's closet and trying on her shoes when I was 4 or 5 years old. I didn't have any sisters, so my access to clothes were limited to what was in my mothers closet. When I was 13 or 14 my mother's youngest sister passed away (she was only 9 or 10 years older than me) and my mother ended up with all her clothes which were stored in our basement. Since my aunt was a "lady of the evening", she had a lot of really cute and sexy clothes. I was in heaven for a couple years until I outgrew everything.

Here's how I started it started when I stayed with a school mate when I stayed there one school holiday he bet me I would not go down for breakfast wearing a skirt, bra, panties and pantyhose of his sisters so I said your on go and get them, he came back with a pink matching bra & panties set a rather nice lemon skirt, white blouse and a pair of black pantyhose it felt rather nice wearing them, he then said lets go down for breakfast which we did his family did not batter an eyelid all they said was we did not think you would take him up on his bet, how do you like wearing his sisters clothes I said it felt rather nice wearing them then they told me Mick likes wearing them as well he normally wears them on a Sunday for the whole day would you like to wear what you have for the whole day I said yes please. The next time I stayed there I found that there for the school holiday there was enough of his sisters old clothes for me to wear a different outfit every day on the last day I was asked if I wanted to take her old clothes with me I said yes please but what will I not have anything to wear on my next visit I was told not to worry as there would be another lot of his sisters clothes I could have the use of this went on for about five years till they moved away by then I had about 30 skirts, 30 bras and about 60 pairs of panties and about 80 pairs of pantyhose

I am not a true crossdresser, but I am a straight masculine man who loves to wear panties sexy ones...I am in my 50's and started in my young teens home alone got naked and this huge rush to put on my moms sexy panties...it is all history now and I LOVE it...

I started 10 years ago. I asked my girlfriend if she would wear pantyhose because i liked how she looked in them. She said the she would only if i did, so i bought a pair of opaque magenta tight(if im wearing them im making a statment). I threw them on under my shorts when we went out that night. That halloween we were going to a party and she came home with a dress and Heels for me to wear to the party. I figured since its a Halloween party, what could it hurt. So i went to the party in my Versace gown and Micheal Kors pumps. I loved the free feeling of the dress and the shoes were surprisingly comfortable for a 4 inch heel. After the party i went out and bought more skirts and heels and i have dressing in womens clothing ever since.

I started crossdressing on a regular basis when i was 13. Me and my cousin were always very close and we had fun whenever we were together. I spent many summers sleeping over her house and just having a great time. One night we were hanging out and i mentioned that i liked her outfit(Sky Blue dress and suntan pantyhose). As a joke she thought it would be cool if i tried on her clothes, since we were the same size. I thought it could be fun so i said yeah. She pulled out a yellow dress, tights, and a pair of heels. I put on the clothes and loved how i looked. The next day we went out and i thought it would be fun if i went in the same outfit i wore the night before. When i walked out and my Aunt and Uncle saw me they were confused, so i just said that i lost a bet with my cousin and had to wear it. They said OK and i spent an entire day at Disneyland in a yellow dress, purple tights, and sneakers(8 hours in heels would have sucked). I have been crossdressing ever since. I dont own very much mens clothing as i dont wear it much. I have 2 Tuxedos, 3 pairs of sneakers, a couple t shirts, and 2 pairs of jeans; whereas i have 7 dresses, 9 pairs of tights/pantyhose, 4 pairs of heels, 3 gowns(wedding, Prom, and homecoming),5 skirts, and 5 blouses.