How I Became A Faggot, Chapter 4

I still wasn't a transvestite I tried to convince myself as I drove home, my new high heels shoved under the passenger seat of my mother's car, my whole groin drenched with cum. I was just into shoes. I wasn't some dress-wearing, cocksucking faggot. I liked girls. I wasn't gay. I had a fetish for saddle shoes. And high heels. And maybe women's clogs. That's all.

But that wasn't all. A week at most passed before I found myself standing in line at Walmart with a pair of thigh highs in my sweaty sissy hand. The cashier was a young girl and, like the clerk at Payless, barely older than myself. She smiled broadly and almost giggled when I put the stockings - my only purchase - down in front of her. Who could blame her? I would have laughed at me too. A sixteen year old guy buying sexy black thigh highs and nothing else? What a fag!

But I was desperate to know what it felt like to wear my new pink pumps in pantyhose. I wasn't a transvestite I still thought. Pantyhose was just part of being into women's shoes. I didn't want to wear other lingerie or dresses. I wasn't going to end up on all fours in some cheap motel room while a hairy forty-five year old man shoved up my miniskirt, pulled down my panties, and whispered into my pierced ear "Are you ready for some fat cock, you little sissy bitch?" That wasn't going to happen to me.

And for a while all that was more or less true. I managed to get through the rest of high school without ever trying on a bra or a pair of panties. I even had a girlfriend my senior year. Before I went away to college I threw out my women's shoes and pantyhose and told myself that I was normal again.

Of course, it was already far too late for me to ever be normal again. I didn't know it yet, but I had forfeited my right to be a real man the night I ejaculated for the first time in my life while wearing girls black and white saddle shoes. I sealed my destiny again and again in a thousand beat-off sessions in my saddles and high heels. That cheap motel room and that hairy man were waiting for me. Waiting for a little sissy bitch in fuck-me lipstick and fuck-me pumps to climb onto a dirty bed and spread his shaved legs. My shaved legs. My red lips. My stripper heels. Me.

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.

How I Became A Faggot, Chapter 2

After first grade at the all boys school in black and white saddle shoes, I switched to a more "manly" blue and brown pair of saddles for second grade. But the teasing continued and finally became too much for me to take. So I started third grade in regular boys' shoes and threw my saddle shoes away. Today, in hindsight, I desperately wish that I had never worn saddle shoes again. If I hadn't, I might not be writing this pathetically perverted blog while wearing Steve Madden four-inch pumps, sheer black stockings, tight pencil skirt, white low-cut blouse, black bra and breast forms, matching black panties, wig, jewelry, makeup and perfume. If I had just never worn saddle shoes again I might know what it's like to have a wife and self-respect, instead of what it's like to have another man's cum in my mouth and dick in my ass.

But of course I did wear saddle shoes again. The desire never left. In eighth grade I asked my mother to drop me off at our local library. When she drove away I walked to a nearby shopping center and bought a pair of girls black and white saddle shoes. I told the saleswoman that they were for my sister and I'm sure she believed me. I mean, odd as it was, she could never have suspected that I wanted the saddle shoes for myself. She could never have guessed that I would bring them home hidden in my bookbag. That I would wait for my parents to go to sleep and then try them on, feeling their stiff, uncreased black and white leather on my feet for the first time in five years. That I would become almost instantly aroused and instinctively start rubbing my tiny penis, still in my underpants, against the sofa in our living room. That I would suddenly and unexpectedly explode in the first orgasm of my life while kicking the air in girls black and white saddle shoes.

Random Public Humiliations

In no particular order...

1. Having a large black woman sing "Tutti Frutti" when I walked by her wearing Bakers high heeled boots at the mall.

2. Watching a college-age woman whisper to her boyfriend in the next aisle at a DSW shoe store and then having the boyfriend laugh out loud and make a beeline for me. The woman had noticed my high heels and now I had to just stand there and "take it" as the boyfriend checked out my pathetic public sissiness. I felt like such a faggot.

3. Having the salesgirl who had just fitted me for "fuck me" black pumps ask if I was interested in one of the purses they had on sale. I'm not sure why exactly, but it caught me off guard and drove home what a total fairy I really am.

4. Walking up a staircase at the mall in high heeled women's loafers while four or five teenaged girls followed behind me giggling and guffawing. Then, when we reached the second level, one of them said very loudly "Nice shoes fag!" and they all broke out in hysterics.

5. Trying on a wig in a wig store when the male Fed-ex delivery person stops in with some packages and looks at me like I'm the biggest queer he's ever seen.

6. Having a very attractive middle-aged saleswoman at an upscale women's clothing boutique stare at my black and white saddle shoes and say"I'm sorry, but we don't cater to crossdressers" as I was standing in front of her holding a little black dress and before I could ask to try it on.

7. Being asked in the lingerie section of a department store by a cute salesgirl if I was looking for "Bras, panties..." When I answered "Just panties" she smirked and said "I thought so. There some nice pink panties over here."

8. Being told I had to use a different dressing room at a women's clothing store after I had tried on a tight, short skirt and having to walk across the store to another dressing room while wearing the skirt and carrying my pants and knee-high women's boots in front of half a dozen female customers.

9. In my early days of public sissiness, catching my reflection in a wall of mirrors at the mall and being shocked at how sissified I looked in a pink blouse, tight women's bootcut jeans, and barely concealed high heeled clogs. I felt instantly mortified and simultaneously wildly aroused and started walking for the nearest exit almost in a panic, only to ejaculate in my panties without touching myself before I'd managed half a dozen steps.

10. Having to walk across a mall food court directly in front of a huge group of high school male athletes while wearing black women's pants that fully exposed the three and a half inch heels of my noisily clicking and clacking pointy-toed women's boots. Utterly humiliating.