a-very-pretty-boy: A Scary Halloween Story Your’s truly, November 2, 1991. Halloween fell on a
a-very-pretty-boy: A Scary Halloween Story Your’s truly, November 2, 1991. Halloween fell on a Thursday that year, so the Halloween parties were two days later, on Saturday. If I had a dime for every transsexual who’s journey began with a Halloween costume, I would be wealthy beyond my wildest dreams. In my case, this was not my first time in public, en-femme. I had been dressing and going out in public as a woman secretly, since I was 17-years old. But this was to be the first time I was to present myself as a woman to my friends and co-workers. I was 28-years old, single, but in a serious relationship with a woman, and thoroughly convinced that I was a heterosexual male, who merely had an unusual “hobby.” There was of course much more to it than that. But at the time, which was immediately after a 6 or 7 year period of not “dressing,” in an attempt to “man-up” and “cure” myself, it seemed like a reasonable explanation. My attempts to be masculine had resulted in me unwarily boxing myself into a very, very masculine life. The more masculine it got, the more I started needing the escape valve of dressing and making myself up as a convincing, attractive woman. It began, this time, not with sneaking out of my parents house in my sister’s clothes, as I did when I was seventeen, but slipping-away on my day’s off, renting a hotel room, and spending the next 12-18 hours being the person I really felt like inside. On this night, I desperately wanted to know how others would react to me as a woman, instead of the indisputably manly and masculine male I played in my daily life. A Halloween costume contest at a bar my co-workers and I often hung-out in, and that my best friend, and supervisor at my job at the time was working his night job as the bouncer at that night, seemed like the perfect opportunity. No matter what the reaction, I could always shrug it off the next day as “Halloween.” Though the big hair, the silk gown, and the high-heeled pumps would be considered a costume today, in 1991, that was how women often still dressed for a Saturday night out. And yes, I consider myself fortunate to have been able to Tranny in a time when women still bothered to dress like women, instead of the slovenly teenage boys so many of them dress like today. I was going for authenticity. I succeeded beyond all my expectations. My boss didn’t recognize me, even though he had watched me sashaying across the parking lot all the way to the door. Whereupon he started flirting with me! The same way he flirted with all the pretty girls, before letting them through the door. I looked him straight in the eyes, and asked him, in my best girl-voice, “You really don’t recognize me?” It took him about 5-seconds, but toward the end I saw the light beginning to dawn in his eyes When it did, his face instantly became a study in shock, and horror. He had just gotten a hard-on over his best friend wearing a dress. He had nothing to be ashamed of. Plenty of other men did too that night. I didn’t buy a single drink. I was flirted with, come-on to, asked to dance, had my ass grabbed twice. Then a group of girls invited me to join them at their table, because I was so obviously alone, and so obviously swamped trying to fend-off the so obviously unwanted male attention I was getting. When I told two of them I was actually a guy, and this was my Halloween costume, they didn’t believe me. Finally one girl, a pretty blonde sitting next to me, looked me seriously in the eyes, put her hand on my sexy, stocking clad thigh, and asked me with curiosity tinged with excitement, “Can I check?” I know exactly what she meant, and I simply nodded and shyly replied, “Sure.” Looking me in the eyes the entire time, her hand moved between my legs, up to my crotch, and though it took a little searching with her fingers over my pantyhose and panties, she quickly found it. I was watching her face too, and noticed her reaction, which started with surprise that it was actually there, then additional surprise at how substantial it was flaccid, which then softly coalesced into a knowing smile. All she said was, “Holy cow.” I had proven to her that I had a penis, but I hadn’t convinced her I was a man. Of course, one of the other girls, not wanting to take her word for it, also wanted to “check.” Her reaction was a giggle-fit at the enormity of the discrepancy between what was in my panties, and the gorgeous and glamorous blonde woman she saw with her eyes. Then the blonde wanted to dance with me. But she wanted to wear my 4″ pumps, because she had never worn heels that high and wanted to try them out. We slow danced. Even with me barefoot, and her 4-inches taller wearing my heels, I was still taller than her. So naturally, I put my arms around her waist. As you can imagine, the sight of two gorgeous blondes slow-dancing with each other had the attention of every male in the bar. My boss seemed both fascinated with how I had scored a slow dance with the most gorgeous woman in the bar, while appearing to be the second most gorgeous woman in the bar, and worried that he was going to have to break-up an attempted gang rape, if the guys in the place got any hotter and steamier over us. It didn’t help that she was sexily rubbing and sliding her body up and down mine, and teasing me with sexy looks and smiles. She was trying to see if she could make me hard. She failed. Or I should say, I failed. Miserably. Every man in that bar had a raging hard-on, except me. And I was the one holding this angelically feminine creature in my arms, while they merely watched. But when in my female form, I had already learned, women held absolutely Zero sexual interest for me. I could appreciate their beauty, I could even feel jealousy towards them. But erotic lust, no. Which didn’t bother me as much as it should have, because I had a girl friend, and was able to perform the required male function with her, when I was a man. But the blonde had tested her hypothesis, and confirmed her original suspicion: I may have had a penis, but I was no more of a “man” than she was. At that discovery, she had actually managed to learn more about me, than I knew about myself at the time. From that discovery on, those girls were my guardian angels for the rest of the night. They kept me at their table, and invited me to dance with them in their girls-only group dances, protected me from the males in the place whom they could tell wanted to do to me, what they never had to worry about me trying to do to them. Two of them even insisted on escorting me to the Ladies Room, when I mentioned I was going to use the Men’s. I became one of the girls. They even named me, deciding that “Jill,” was the perfect name for me, because they said I looked like Jill Monroe, Farrah Fawcett’s character on Charlie’s Angels. In between that they pawed all over me, checking my clothes, discovering that my breasts were actually water balloons (Internet shopping for breast forms did not exist in 1991), marveled at how well I had done my make-up, and talked about how cute I would look in such an outfit or another. It was a magical night for a tranny. I was a huge success as a girl. I even won the costume contest. Fifteen hundred bucks, or an all-expense paid 3-day cruise in the Caribbean. I took the money. A girl can always use more shoes. After getting on the stage when it was my turn, I twirled-around a couple times like a fashion model, to a combination of wolf-whistles, hoots, and some confusion as to what my costume was, since I just looked like any other dressed-up woman in the bar. I then removed my wig and held it up in one hand, then pulled one of the water balloons out of my bra and held it aloft in the other. There was dead silence for a moment. Then the women in the bar started cheering and hollering, and applauding. The DJ, announcing the proceedings from his booth uttered “Holy fucking shit, and the faces of the men I could see had that same look of shock and horror my boss’s originally did. I of course put the wig back on - ain’t no tranny born who woulda gone around without it the rest of the night - and my water balloon boob back in my bra. Though I had ended the illusion, I still got funny, confused looks from the men for the rest of the night. Though a couple of co-workers did come-up and pat me on the back and tell me what an amazing costume it was. A few men even bought me drinks, and told me what a “great joke” that was to play. But not the ones that had bought me drinks before. Those guys wanted to kill me, and I could clearly see it in their eyes. I had made them doubt their heterosexuality. That is the last thing you ever do to a man. I don’t know what happened to the girls, or the blonde. I have no recollection of our parting, or any memory of the night after that, except my boss, the bouncer, ended-up having to walk me to my car, because he saw the way a few of the guys were looking at me too. The epilogue to that story is the next 23-years. And here is me, today. And it’s all real, honeys - the hair, the boobs. Oh, I still have the penis, I haven’t gone that far… yet. Not that there’s much I can do with it, besides pee standing up. It works, but nothing like it used to. And that has nothing to do with hormones, but rather my mind. Women don’t need penises. And it plays no role in my life, rather than sometimes making an unsightly bulge in my jeans. Oh, don’t get me wrong, I can fuck like a rabbit. Or rather, a Bunny. But I’m the fuckee, not the fucker. Couldn’t do it to the old way to save my life. If you want to make something happen, to effect some change in your life, then think solely of that thing. Your dream will become real. Just be careful it doesn’t turn into a nightmare. All I can say is, be careful how you play on Halloween. It could happen to you, too. That’s where it always starts. The boys put on the dresses, then don’t want to take them off again the next day. Trick or treat. great story -- source link