How’d You Start?


Active member
How did you start crossdressing? Any fun stories getting caught, hiding it, sharing it with others? Do any friends or family know?

I didnt have sisters, so I was attracted to panties/thongs as thats the closest thing to a woman. (No weird incest stuff, I only had access to what was in the house and viewed them as just clothes).

I had plenty of opportunities to dress up, sometimes just panties, then a bra and other clothes got mixed in. I remember doing my math homework one evening in a short denim skirt and everything was female clothing. So fun to hand in the homework next day knowing how I was dressed. That was grades 6-8, things didnt fit well after that, and started to buy my own things.

Fast forward through high school, college, and adulthood I wear panties whenever I’m not at work. I also wear leggings and skirts depending on the season. I’ll wear both publicly, but am careful about times and locations so I dont run into someone I know.


I started by wearing my older sisters thongs and gstrings when I was younger. She had a lime green gstring which made my cock rock hard, and I used her baby blue thong to stroke my cock with. Made me blow the biggest loads. Fast forward to now, I like to be naughty in my fiancés thongs and gstrings, although I now toy my ass and cum all over my own face with a big urge to suck some cock while both in naughty panties!


Well-known member
I started with my sisters old clothes in the storage room. The. When she went to college I would sneak in her room all the time. I wore almost her whole closet. Cumming in dirty and clean clothes. I loved her panties and tight clothes. My younger sister I just wore a few things and as I got older that faded but I date MTF and we play around sometimes.


Active member
When I was 13 yo, I started to wear my mom's panties. It was in the beginning of the 1980's and thongs were not so common but my mom had some. I thought it was very sexy when she wore it and I immediately loved the feeling when I tried it. I tried her panties, bras, some clothes and make up.
I stopped all when I met the girl who will become my wife. But after we divorced, the urge to wear some nice lingerie came back. I started to buy my own lingerie, then feminine clothes, then make up...
Now, I only wear thongs, every day, even at work.
When I am not near my house or job, I like to wear bras, stockings in public. I like to go to the beach in some feminine bikini thong.
My mom knows, she saw my thongs and bras drying and immediately understood they were mine. A female cousin knows, she saw my whaletail. My daughter knows, she caught me in lingerie with a man... oops !
I started when I was in the sixth grade I would wear my sister thongs when she wasn't at home and in eight grade with the help of my friends I dress up as a girl for halloween and in 9 grade I started only wearing girls clothes full time


I think it started when I was young, like probably 10 or 11. For some reason I wanted yo try on some of my mom and sister's things and then nothing for a long time.

When I got married, I started wearing male thongs and g strings and did so on and off for 20 years. Now, I only own thongs and g strings.

After 2 years of only wearing thongs and g strings, I wanted to try lingerie and so now that is what I wear to bed.

Next time I buy underwear I am going to buy women's thongs and g strings instead of my normal men's thongs and g strings.

I'm really liking women's lingerie and how it makes me feel. I'm going to start wearing it under my normal clothes.