How I Became A Faggot, Chapter 3

Well, you don't need me to tell you what happened next. After discovering the joys of masturbation and the key to my arousal in one fell swoop, I repeatedly beat off while wearing my new saddle shoes. And somewhere deep in my psyche a terrible, unbreakable bond was formed. You see, I didn't have the good fortune of masturbating for the first time while looking at pictures of naked women. I got off for the first time while wearing women's shoes. And for the second time, and for the third time... and for the 100th time.

As guilty and ashamed as I felt about my behavior then, I consoled myself with a temporary truth. I was only interested in wearing saddle shoes. I couldn't be a transvestite because I had no desire to wear any other article of women's clothing. Saddle shoes and that was it. It could be my little secret.

But that comforting truth didn't stay true for long. By the time I entered high school I was tormented by powerful urges to wear other types of women's shoes. I went to a co-ed high school and I would look at the girls in my class and wish I was wearing their suede clogs or their pointy-toed flats. After school, I would masturbate in my saddle shoes and fantasize about wearing high heels. But they were only fantasies then. I couldn't act on my perverted impulses because I had no way to shop in secret. And my mother's shoes were both unappealing and too small.

When I finally turned sixteen my world truly changed forever. Normal guys can't wait to get their driver's license so that they can go on dates and drive around with their friends. For a budding sissyboy like myself, though, it meant something entirely different. I could finally buy my first pair of high heels. I can still remember almost everything about that day.

I went to a Payless shoe store not far from my house. The store was completely empty except for the salesclerk, a young black guy probably only a few years older than myself. I remember how nervous I was to leave the men's shoe aisle and walk down the women's aisle. I remember willing myself to do it because I wanted to wear high heels so badly. I remember hurriedly scanning the shoes in what I thought was my size, wanting desperately to get out of there but wanting equally desperately to stay until... until I saw them. The object of my desire. Not a new video game, or a hot car, or a busty girlfriend. No, not for me. Here was what I wanted. Sissy pink three inch pumps. A fairy's first high heels.

I picked up the open shoe box and clumsily put the lid on it, hoping this might somehow conceal what I was buying. I could literally hear my heartbeat as I walked to the register. I put the box on the counter in front of the black guy. He looked at me, then at the box. And then, without saying a word, he opened the box and looked back up at me. Although I've seen it many times since, I'll never forget that first time, that first look. He looked at me and he knew. His look said I know these high heels are for you, fag. I know exactly what a sick, pathetic, crossdressing homo you are. You disgust me, queer. He picked up one of the high heels out of the box and checked its size. Then the other. Then he put them both back in, closed the lid, and rang up the sale. My whole arm was shaking when I handed him the money. I was utterly mortified at what I was doing. At what I was becoming. And then, before I could even really process what was happening, the transaction was completed and I was out of the store, racing back to my car.

As soon as I started to drive away I knew I couldn't wait a minute longer. I'd been jerking off in anticipation of this moment for almost two years. I had to know what it felt like to wear women's high heels. I had to put them on right then. So instead of leaving the strip mall I circled around behind it, to the back of the stores where the trucks unloaded and no one parked. The coast looked clear, so I parked next to a large dumpster, pushed the driver's seat back as far as it would go, tore off my socks and sneakers, and picked up my new pink pumps. It isn't just saddle shoes anymore, I thought to myself. But I didn't care. My pathetic excuse for a cock was harder than it had ever been. I put them on.

There I was, just turned sixteen, sitting in my mother's station wagon parked behind a strip mall, wearing normal sixteen-year-old guy's clothes, and bright pink three-inch high heels. I was no normal sixteen-year-old guy I suddenly knew. I looked around to see if the coast was still clear. I had to know what it felt like to stand and walk in high heels. I got out of my car and took a few terrified steps. And then, without so much as touching myself, I came as hard as I have ever cum in my life. It literally caused me to double over as if I'd been punched in the stomach. What an unbelievable pervert I am, I can remember thinking immediately after I came. Standing there in the empty lot in women's pink high heels. My warm, sticky spoo soaking through my underwear and my pants. The door to any sort of a normal life slamming shut behind me. I am a fucking pervert, I realized with astonishment. I am a sixteen-year-old sexual pervert.