Public Humiliation Chronicles, Volume 1

Well, I did it again. Matching bra and panties. Pantyhose. Orange women's button down shirt open low enough to show my white cotton camisole underneath. Tight women's flare-legged jeans. Women's waist-length black winter coat. Oh yeah. And these boots from Victoria's Secret.

I always feel the same reluctant anticipation as I approach the mall's highway exit. Part of me doesn't want to go through with it. Part of me wishes I had just beat off at home instead of deciding to expose myself to the humiliating ridicule another part of me craves. Sometimes I say little mantras out loud as I look for a space in the parking lot. You're a sissy. This is what sissies do. Face the shame.

Getting out of the car is often the hardest part. I usually have to wait - nervously, pathetically - for whoever is nearby to pass. I can't just "hop out" and stroll inside. I need a minute alone, standing between parked cars, to pull my jeans down so my high heels are as concealed as possible. I need to adjust my bra straps from the car trip. And I have to push my tiny, half-erect, half-limp dick down in my already-damp panties. I'm such a fucking pervert, I think, as I wipe the precum from my panties off my hand and onto my jeans. God, I hate myself.

And then, when the coast looks clear, I'm off. Out in the open. Heels clicking loudly on the pavement. Eyes focused on the mall entrance. Trying not to look to the left or the right. Trying not to notice if anyone's noticed me. If I'm already being gawked at. If some college-age woman and her boyfriend have stopped dead in their tracks to stare at the fag in women's clothes. At the sissy transvestite on parade.

How I Became a Faggot, Chapter 1

A lot of transvestites with webpages have a section discussing how they started crossdressing. Offering an explanation seems natural enough. After all, what guy wants to end up in a gold dress, blond wig, lipstick and high heels? I know I didn't.

But I did anyway. I ended up trying on 4-inch white pumps at Bakers while two giggling teenage girls took my picture with their cell phones. I ended up with my first serious girlfriend walking in on me while I was masturbating in her bra and panties. I ended up on my knees with another man's dick in my mouth.

So how did this happen to me? How did I ruin my life?

It started with a pair of saddle shoes. I went to an all-boys school. We didn't have uniforms, but the all-girls sister school did. White blouse, plaid skirt, and black and white saddle shoes. The two schools ran a joint, co-ed kindergarten at the girls school, which I attended. In black and white saddle shoes. Yeah, that's right. Thanks to my mother's fashion sense, I began my education as the the only boy wearing saddle shoes amid a sea of girls in them. At first I hated my saddle shoes and the teasing they brought me. But slowly, over the course of the school year, I began to like wearing them. So much so that when I went to the boys school the following year for first grade, I asked my mother for another pair. Somewhere inside of me, in some way I didn't understand, a switch had been flipped.

But was it really that simple, that innocent? Did being made to wear saddle shoes in kindergarten turn me into the sissyboy I am today? If I'd worn sneakers instead of saddles then, would I be wearing boxers instead of panties now? Would I fantasize about fucking women instead of being fucked by men? Would I never have become what I am: a humiliated transvestite faggot?