Girl of summer (still around)
I'm 18, male and I'm a serious crossdresser. My 'girl' name is Vanessa. Last summer I was able to wear my moms clothes all day while she worked. It was a blast, especially going out and people believing I was a woman in her 20s. I'm now a senior in HS. Last September was hard as I had to give up dressing up THAT often. Once or twice a week for an hour or so wasnt doing it for me. Last November, on a Saturday I decided to surprise mom and I got totally crossdressed and made-up, with wig, jewelry, shaved legs, and polished nails [all 20!]. I made an entrance into the living room to my mom's surprise! I sashayed and asked her what she thought. She wanted to know what was going on, so I said I was having fun! At that point she sat me down and got serious and we talked. She was blown away at how thorough I was, especially my polished toenails and makeup skill. She asked flat out how long I had been wearing her clothes, so I confessed it was since I was 11. She said she suspected for a few years that I was playing dressup, but seeing me right then walking so easily in 4 inch heels and acting so normal as a woman sold it for her.
We talked for over an hour. I finally asked mom if I could continue dressing up, even when she was home. I told her it was important to me, and how much I enjoy it. She agreed, limiting me to just the clothes, shoes, jewelry, and makeup she no longer uses. Bur she did say I needed to be disciplined, as I had to that point been doing this on the sneak without permission. She grounded me for 2 weeks AND I wasnt allowed to crossdress.
Being allowed to dress everyday after school and not having to hide it is soooo totally awesome!! I am so convincing as a woman [being 5'4" and 120 lbs helps] and I also became an honor student. My 31 y/o F neighbor is like my best friend, and is helping me with all my fashion & sexuality questions, and gives me clothes too. When I am alone, I go to her apartment and she lets me wear sexy lingerie [and giggles when I get a stiffie]. I love my mom dearly for being so understanding with me, and letting me be Vanessa whenever I want.