I believe I was 8 or 9 when I decided to put on my very first pair of tan pantyhose and has grown from there. I started buying shoes and more clothes by my late teens, then had a dry spell as life got in the way. Though, that changed once I got married, as I decided to tell my then GF that I enjoy being Adriana and she was very open and understanding. Today we both have fun shopping together and picking clothes out for either of us to wear.
I was about 11, the late 50's. Girls had always interested me, and I had had an urge to wear girls silky panties for many years, and in those days boys were just not supposed to dress up like girls, so I had resisted this temptation, but broke down, seeing a pair of mom's silky white panties hanging on the clotheshorse...I slipped them on...what a thrill...and here I am today, at age 66, dressed fully as a woman...and enjoying it as much as I did then. I Love Cross Dressing so so much.
I think I was 5 or 6, my cousins panties. I just needed underwear and she gave me some. I liked them, I think they had multicolored stripes on them but its hard to remember for sure.
I've tried wearing panties since then but by themselves they didn't do much for me other than make me a little bit uncomfortable (physically).
Tasha
I was about 20 (it was only a few years ago and during the summer). I had expressed interest after I had seen my (then) girlfriend wearing a dress to a formal dance in High School (that was the only time I had ever seen her wear dresses, she was also still in High School at this time (we started later than most people)). I told my mother because I was to worried about my parents finding out, so I thought that I should just say something right then and there. My mother gave me a pinafore that she had. I was (and still am) in college at the time, but I never expresses the desire to dress in my room in the residence hall (you can probably guess why).
I guess ive never really thought about it, i think id have to say i was around 10 or so, I had thought about it a LOT before then though.
Scouts Out
I started when I was 10 , wearing my neighbors daughter's bra and undies. I would borrow them from the laundry room and return then after I was tired of them. When I was 15 ,I met another dresser and together we would borrow or buy things to wear. He moved away after high school and I never saw him again. I married and stopped Dressing until we divorced 10 years later. I started dressing again and was able to pass. I would go away on the weekends to do this ,coming back from one trip I met my second wife and stopped again. I tried several times to talk to her about it ,but she thought the person who did this was sick . We divorced after five years and I started dressing again. It was easier to buy underwear and clothes , the girl at the hair salon would do my hair and makeup . Nails and pedicures also done by a cd friendly shop ,omg things were great !
Then I met my third wife , yes I stopped , we moved away . I had an emptiness and long for it . Then one day while I watched her dress , I said something about dressing to her , she smiled and we talked . We shop together and have pedicures ,, I have been taking baby steps with her . So far things are good .
I first wore tights when I was about 5 or 6 as a Halloween costume. I fell in love with tights then. I am not sure what eventually drove me to try on the rest of my mom's clothes. But around the age of 10 or so I started trying on her clothes. I fell in love with a blue and green tartan print pencil skirt and some heels that I love to walk around the house in when I was alone. Great memories.
The first time I truly remember dressing up was when I was 4 years old. I was really good friends with the twins across the street, one was a boy and the other a girl. One day we were playing school and somehow convinced them that we needed a second girl to be a student since Sarah was playing as the teacher. after this I offered my self to be the girl and suggested that I should change to play the part
I first thought about it around age 7. I noticed how the girls in school ere dressed and wanted to be like them. Around age 10, I tried on a skirt for the first time. After that I would sneak into my Mom's or sister's closet to try something on whenever I had a chance. I've been hooked ever since.
Kristen
"I'm a lumberjack and I'm OK..."
My first real experience was age 13 or 14 when my sister dressed me up in her school uniform. She had me in all the lingerie, skirt, blouse, vest, wig, and makeup. She commented I was a pretty good looking girl and I should go to class with her sometime. (Like that would happen). I asked to do that the next night too and she did dress me up, but I had to slow down so the folks did not get suspicious. But I was hooked both line and sinker. I then got a pair of her panties and pantyhose and hid them so I could wear them at night in bed and enjoy the feeling. It has been on and off again ever since.
4 yrs old Mommys silk stockings
With me it started with a short black open girdle out of my mum's drawer, but then finished up within a short time working through my mum's entire collection of clothes (back in the sixties). Although it would be almost 40 years before I started acquiring my own, and learning makeup, along with wigs, hair removal, the works. It was that initial imprinting all those years ago, that turned the light back on in my brain.
At 6. After few encounter with boys
58. just experimenting but it is erotic.
I like this thread and, unlike other threads with repetitive opinions and suggestions which I tend to by-pass - I like to read each experience entered here. They remind me of "my first time" - very special, very intimate, very sexy, exciting, life changing. I feel happiness and a share a bond with each person as I read their "first time." I hope this tread goes on, and on....
I am delighted this thread is still active, Heather!QUOTE=heatherdress;3488919]I like this thread and, unlike other threads with repetitive opinions and suggestions which I tend to by-pass - I like to read each experience entered here. They remind me of "my first time" - very special, very intimate, very sexy, exciting, life changing. I feel happiness and a share a bond with each person as I read their "first time." I hope this tread goes on, and on....[/QUOTE]
When I was like 8 I grabbed a dress of my mom's that really caught my eye and tried it on, I think that was my first time ever. At some point in my early teens, I grabbed some stuff from my sister and tried it on, so the desire to dress was always there I think. The first time I fully dressed was in my mid-20s, when I was able to get a full outfit and a wig and tried it on
Sadly for my SO, it wasn't until after we were married and had 1 baby. It's been a hot button topic for almost 9 years. I have taken the honesty route with her for many years now and still stumble through it. She's allowed me be a member on this site to do more research, sharing, and getting me to a better place in life with my CD and the male / female balance.
I started out by trying my mom's panties when i was about 7. Then starter trying her bra and dresses whenever she was out.
I was around 8 when I would try on mom's lacy panties and a bra from the hamper in the bathroom. This, of course, started me down the path. On of the happiest days of my childhood is when my mom and sisters dressed me up as a girl for Halloween when I was 11. White party dress with a pink bow. Wig, makeup, nylons, panties, and a sock stuffed bra. I had such a great time. They still do not know about my "curious habit" as my wife calls it.
At 10 I tried on my mom's one-piece swimsuit and loved it!
I do not remember a time when I did not dress.
Mom wanted a girl and at a young age used to dress me as a girl. Not all the time but a lot of it. Just before I started school she had my hair cut short and that was the end of that.
I kept dressing when I got the chance.
I found out about being dressed as a girl when I talked to my dad as he was dying. I brought him a picture of my daughter in a dress so he could have pictures of the family around him. He told me that it was a picture of me. When I said it is his granddaughter in a dress he told me that it was me and he told me the story of mom dressing me and treating me as girl.
Mom told me she wanted me to be a girl, that she kept my hair long, and people thought I was a girl but never could get her to admit to anything else. She is still alive but having medical issues I would really like to learn more while I can.
About ten years ago mom, my wife and myself went out to a Halloween party all in dresses in a group theme and she enjoyed that.
I don't even remember when I first wore my mom's clothes. Junior High? I just know I always wanted to be a girl.
When I was probably about 10 yrs old. There Was girl down street and she was tom boy. She would pretend to be boy and I would be girl. That Was happy time
I was 8 or 9 and my costume for a Halloween party i dressed as a girl. BEST PARTY EVER!! Occasionally all my live i would sneak wearing panties, bras and nighties. This past January my wife found out and has been really supportive, although shocked. Now I dress a lot more, just bought my first wig this past weekend.
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