On Halloween night during my senior year in college, I went to a costume party in a broken- down frat house dressed as a self-appointed character I'd been inventing for months, years, if you really want to get technical. I looked like any normal guy in college by then; short sandy blond hair, blue eyes, white polo shirts and khaki slacks. Though I was only five feet six inches tall, there was nothing about me on the outside you would have considered peculiar. Most people would never have guessed that I was even gay or that I had a secret passion for lipstick, earrings and very high heels.
It's not that I didn't like being a man. I did and wouldn't have changed that for the world. But the thought of shaving my entire body to the point where every conceivable inch of skin was smooth and soft, and then putting on a tight corset, black stockings and dangerous stilettos gave me an erection that lasted for hours.
Good sex for me was all about dressing up. All this was only fantasy back then, and though I'd once had the courage to buy a pair of cheap, size eleven, four-inch high heels at Payless (buried at the bottom of my suitcase and only worn while I masturbated in private), I'd never actually had the guts to go out in public dressed as a sexy woman.
Not until the night of the costume party, anyway. I wasn't cruising for guys either. I just wanted to dress up and feel sexy for once.
I'd spent months ordering the most precise items on the internet, things I knew would make me appear and feel really hot. The general costume consisted of a black—beaded evening bag, a short black taffeta skirt, a skintight, black lace corset trimmed in silver, a black mask that covered half my face and six- inch black stilettos. But it was the small details that really made the costume work: rhinestone earrings with a matching necklace and bracelet; long, red fake fingernails and full makeup; a pair of realistic vinyl boobs with big nipples that actually felt real when you squeezed them. I'd signed up at a tanning salon a month before the party so my legs would be smooth and brown...no need for stockings. And best of all, a long, blond wig with a snug fit so I could toss my head around without worrying about losing it. Actually, my only real worry was holding my eight-inch penis down all night. So I found a strong black thong-sock (no string so my ass would be bare) with a heavy waistband to keep my junk concealed. I knew if I got really hard, I could point my dick toward my stomach and the waistband would hold it in place.
Though I made a few mistakes (I didn't need eye make-up with a mask...when the wig was on my head, I realized all I needed was a little red lip gloss to pass), my first time going out in public was actually quite professional. And it was supposed to be outrageous. After all, this was a costume party. The high heels made me feel sexy and empowered, and as I strutted across campus to the frat-house party, a couple of guys turned to stare at my bare legs. They weren't the best-looking boys on campus, but they were real men, they were pussy hounds, and they liked the way I looked. I concentrated on my movements, very carefully so that I wouldn't appear masculine. I didn't want to come off as quasi feminine either, so I simply restricted each movement to avoid anything awkward or too calculated. Then I smiled and said, "Hey guys."