How Did You Get Started

[Cristy2]

I'm sure there has to be a thread on this already, but how did you get started crossdressing? Myself, I've been crossing for as long as I can remember and I honestly don't remember how or when I got started.

[Sabrina133]

Middle school. First tried on my sisters skirt and matching top --- just couldn't stay away.

[kimdl93]

There was literally one posted by the identical title just a few days ago. Search for it.

[xd-tigger]

It started when I was four years old. Saw my sisters skirt on the bedroom floor and tried it on. Got caught too.

[heatherdress]

My wife insisted that I buy a pair of high heels.

She knew I liked when she wore her heels and wanted to know if I would enjoy owning and wearing a pair of my own. I purchased a pair of black stilettos, tried them on in front of her. It was great - exciting, different, sexy, fun. She then gave me some nylons and underwear. Each step was better and more exciting. She then used makeup and spiked my hair with gel. I was shocked and loved it.

We talked a lot. Assurances, discovery, intimacy, pleasure, fun. She is very happy she initiated and supported and enjoyed my crossdressing.

[Stephanie47]

I can't exactly remember my age, but, it was as a single digit kid. My mother always hung her nylon slips to dry in the sole bathroom of the apartment. I loved the feel of the nylon. I use to take them off the clothes rack and try them on, dry or wet. It didn't matter. Later, as I became more adventurous I added her bras, ugly panties, girdles and stockings.

[Cheryl Ann Owens]

I was maybe 4 years old and slipped on my grandmother's dress. It's all a blur but the next couple years I was fascinated by my sister's clothes and they even did my nails with polish and it was suddenly supressed. When I was 12 something "clicked" in my head and I had a sudden desire that felt perfect and right. Having a couple hours to myself after school I would try my sister's clothes and that, as Paul Harvey used to say, is the rest of the story until I leave this planet.

Cheryl

[Beverley Sims]

I had three girlfriends encourage me.
We all then shared a house and they would dress me up to make a foursome.

[irene9999]

I started in high school trying on my mom's/sisters clothes. I was really really skinny as a teen so her clothes fit me perfectly, I liked watching my legs in the mirror and thought they looked as good as other girls

[JamieOH]

I can remember having the urge to wear dresses and pretty girl things from about 4. When I was about 8 or 9 I took some of my sisters clothes and would wear them late at night while everone was asleep which I did as often as possible for many years. . I especially loved this one pink chiffon nightgown. I would wear it and watch Soap which was always on very late because of its controversial content. I loved that they had a CD on that show. Helped me to not feel so alone and abnormal.

[Beth Wilde]

A friend at school encouraged me to try on his sisters tights...... Never looked back!

[Seana Summer]

I started by trying on my sisters pantyhose. I was maybe 3 or 4, not yet old enough to go to school. I have no idea why I did, but I liked the feeling of nylons ever since.

[AmandaM]

I was about 4 years old. Wore my sister's clothes.

[anneob2002]

Slips when I was 4 or 5. Oh what a feeling!

[Krista1985]

First time in my mid teens was a one-off,

Found my girl cousins bra hanging from a towel rack in my bathroom and had to put it on for some reason. I really enjoyed the experience as I had developed small moobs that made the tiny bra fit snugly. "It" didn't happen again until grad school. Now dressing is a regular occurrence.

[Sister Rachel]

Granny's knickers aged 3 or 4. Making pyjama jacket into a skirt aged 7 or 8. Trying on stepmother's bra, panties and tights at 12/13, sneaking home to fully dress in her clothes at 16/17, occasional and often ill-fitting purchases from catalogue during my 20s ...

[Jilmac]

I've said this in several threads before but it's worth another say. At around age 7, an older cousin dared me to wear panties and a dress. I took the dare but was scared of being made fun of, which my cousin did when he saw me. Even though I was frightened by his teasing, I loved the feel of the panties and look of the dress, and I was hooked. I also had three older sisters and plenty of clothes to experiment with, and that gave me even more reason to love dressing.

[Robin777]

I started dressing when I was 12 or 13. I got attracted to my mothers underwear. then I started wearing her bras and slips and other things, pantyhose,garter girdle and stockings. Then I started putting on her dresses. It just felt like the natural thing to do. I remember I was attracted to women's clothes at an early age. Looking at them in the Sears and Penny's catalogs. I remember I always had a fascination with them.

[Cristy2]

I used to dream of being a fashion designer, but I can't sew worth a crap.

[franlee]

I was 16 and dared my girlfriend to exchange clothes to get her out of hers for "fun," well it worked and started a long chain of events for the last 43 years or so!

[Kate Simmons]

My Mom's panties when I was 5 and it escalated from there.

[Requal Jo]

My sisters dressed me as a girl from age 3 to 6 years and took me out with to play with them. Had a break for a few years and got the feeling again for a couple of years, then stopped for while to have a family. Kids grown up and left home so got the feeling again. Requal.

[aitun]

I started in high school trying on my sisters clothes. I was really really skinny as a teen so her clothes fit me perfectly, I liked watching my legs in the mirror and thought they looked as good as other girls

[Tina B.]

Age 6, sisters white nylon slip with lace around the bust, and white nylon panties. Wasn't my fault, she left them in the bathroom, I just happened to find them.

[edith]

My mom's underwear and makeup at around 6.