I'm a M, 29 and a crossdresser. I live with my mom in a nice garden apartment development. Every Halloween I help mom with the annual Halloween party for the kids in our development, which is in the community room. Every Halloween since I was 5, when I dressed like Red Riding Hood, I've dressed as a female. Snow White, Cinderella, Ariel, ballerina, witch, cheerleader, Elvira, Posh Spice, Madonna, you name it. Most folks in our development have no problem with seeing me dressed female every Halloween. Of course, as I get older, I tend to get more racy, but never vulgar or promiscuous. 2 years ago I caused quite a stir as I was a French Maid, complete with fishnet stockings under a very short skirt, and 5" spike heel pumps. Last year I was Katy Perry in The California Gurls video, with the blue wig, short shorts, smooth bare legs and high heels, and the cupcake bra. I find the tween girls are fascinated by my full-on feminine outfits. And some of the moms who know me a long time chat it up with me like I was a woman! I love it!
After Halloween '09, I confessed to my mom that I wanted to crossdress more often. She wasnt too surprised, knowing how much I enjoy every Halloween, and how easily I walk in heels and act female. At 5'5" and 120 lbs, many of moms clothes fit me, so she gave me some things she doesnt wear anymore. Mom was always very stylish, and she also gave me costume jewelry, accessories, and old makeup. Plus the jackpot, 9 pair of high heels. Her shoes are a bit small [womens size 8.5, where I really need size 9], but its worth the discomfort! She let me dress up once a week, and it was a blast. I gradually started buting my own womens clothes, got a good wig, and took makeup lessons. By last winter, I started going out to drag parties. Meeting other crossdressers is a great thing for me.
I'm dressing up more often, like 3 times a week, but since I do most of the housework, mom lets it go. I've started going shopping as a woman, and no one seems to know, except for those who know me a long time. And they kinda wink at me and tell me how womanly I am. This Halloween I'm dressing like an adult Bo-Peep - very short red, pink and white dress, pink garters, ultra sheer nude, sandalfoot hose, and red ankle strap platform sandals with 6" spike heels. Red toenails, OF course! I'm sure I'll be the hit of the party.
Oddly, the one thing mom bugs me about is my GF. I had a GF who broke up with me over a year ago because of my increased crossdressing. I met a nice lady last spring at a crossdresser party, and we became friendly and started dating. Obviously, she likes crossdressers, and we have a good time. But she is 49 years old, and thats what mom isnt too cool about [mom is in her early 50s]. But my GF and I are sexually intimate, where my last GF never had sex with me in the almost 3 years we went out. Truth is, before my current GF, I hadnt had sex in almost 9 years, so I'm loving this. She even dates me when I'm crossdressed, which is a blast! She is the "boss" of our relationship, but thats fine with me. I hope mom comes around on this like she has accepted my feminine side.