"Simmer down dear reader, probably nothing here to really get excited about. I'm just thinking back on moments that led me down my personal path. I guess I can call these 'woulda shoulda couldas'. Having grown up in a seemingly average small midwestern town, my story probably isn't unlike a lot of guys' stories.
I knew pretty early on that I wasn't quite like the other guys. Around age 10, I remember seeing an article in a magazine about The Rocky Horror Picture Show. To say I was fascinated was an understatement. No, I didn't want to dress up or anything...but I was very aroused by the thought of a guy in fishnets. This led to many years of fantasies about such things. But, in a small midwestern town, was such a thing really any sort of reality? I figured it probably wasn't, so I kept telling myself "Girls, stupid! You're supposed to like GIRLS!"
When I started high school, there was a kid in choir with me who really got the ol' fantasies popping up again! He was a black kid, but damn...effeminate isn't even the right word to describe him! 'Flamboyant' barely scratched the surface! 1st day of school, he showed up wearing a very loud floral shirt, jelly shoes, and Gloria Vanderbilt jeans! My goodness, how good his ass looked in those. It's tough enough for a 14 year old to contain a hard-on on the best of days, but seeing someone who would become the subject of years of masturbatory fantasies, in the flesh, made matters...er um...hard to not notice. But again, this was the 80s, in a small town, in the Midwest, and to add insult to injury, interracial romance of any kind was highly frowned upon. So of course, I was finding myself attracted to everyone I shouldn't be (according to the norms of the day). Yes, there were lots of pretty girls in my school and yes, I had my share of fun with them, but none were really what turned me on. Like the average teenager, I was perpetually horny, and being considered good-looking (although I have yet to understand why) I had no problem getting almost any gal I wanted. One gal used to practically molest me daily on the bus home. She eventually got a taste of my sexual appetites, but that's a different story. Mercy, she had a great ass.
During freshman year, my best friend came out to me. We all had pretty much figured he was gay, and honestly, none of us really cared if he was or wasn't. He was a nice kid, fun to hang out with, and we both like smoking pot. Hell, he gave me my first blowjob. It wasn't great but it was a release. He knew I liked black girls, so after a while he would bring a few around if we were hanging out and getting high. Yep, I had some fun with them too. Looking back, I was an oversexed little weirdo. But I wasn't getting the sex I wanted, so it often felt like an exercise in futility.
I fucked my first guy in high school. He was black, my age, and damn...that ass was about perfection! There's a story about it online somewhere. But, this was just a fluke. A one-off. In our town, we both would've been killed had word got out.
There was a gay bar in town, and at night it wasn't unusual to see black 'trannies' (not a fan of that word but it's better than what the locals called them) out and about near the bar. Needless to say, this got my motor running every time I'd see them. But, as a white suburban kid in a small midwestern town in the 80s, there wasn't much I could really do about it.
For those not old to remember such a time, anything 'trans' was unheard of for the most part. If it was mentioned at all, it was usually in disgusted, hushed tones. You couldn't even find that sort of porn. Oh sure, you could find almost anything else. Even gay porn. But nothing like that. If you did find it, it would be in the seediest dirty book store among the seediest stuff...bondage, S&M, etc. I wasn't into that (still not really into it, although I've had my experiences). There was no internet. No Jerry Springer. Video stores definitely didn't carry it. Even in the big city an hour or two away, it was almost impossible to find.
Speaking of the city, I'd go there any chance I could. A round trip bus ticket was maybe $10. My grandmother lived in the city, so I'd catch the bus, go to a concert, lurk around downtown a bit, go stay the night at grandma's, and catch the bus home the next day. Every now and then, while lurking around, I'd meet a 'tranny', and being considered good-looking, usually at least got a blow job, sometimes more. Finally! Good sex! But it wasn't anything sustainable, so frustration became a normal part of my life.
One evening, on the bus ride back home, I found myself sitting in the last seat on the bus with the hottest black 'tranny' I'd ever seen. To this day I still remember what she was wearing. She had her hair in a long, twisted braid, coming down over one shoulder. She was wearing all white, a Flashdance sort of top, and white leggings. OMG! That ass! I still dream about it. She was really sweet. Maybe 30 (so she was probably worried about getting busted), but obviously interested. One of those woulda shoulda coulda moments. There were 2 reasons I didn't act on the situation. One, my best friend was with me (but sitting in a different part of the bus - it was crowded). Two, I had to get to my part time job as soon as we got back to town. Yep, the old anxiety and self-loathing kicked in. Rather than just be myself and risk having fun, I stayed in the safe zone. I could still kick myself for that. If on the extremely rare chance she should read this, please know I doubt I've ever wanted anyone as bad. Hell, she'd have to be 70 by now! Probably still hot.
Another of my woulda coulda shoulda moments happened in a restaurant. A friend's uncle owned a chippy, and I used to hang out there if I had nothing better to do. It was downtown, and maybe not in the best part of town. One night, a black guy came in to order, I think it was, chicken wings. Mind you, back then, most white folks hadn't quite figured out how awesome hot wings were...but the black folks knew. Anyhoo, I remember him like it was yesterday. About 5'11, dark skin, Jeri curl, a pullover, and some incredibly tight jeans. Nope, no need for imagination with that outfit. He made sure anyone who looked knew he was packing and packing big. I also remember his cologne, which he had liberally doused himself with.
I've always been a friendly sort, and if I was hanging out at the chippy, I'd usually greet everyone who walked in the door. As usual, I greeted him and he locked eyes with me. It was clear from the get-go, he was liking what he saw. He began a bit of chitchat. I guess maybe he was testing to see how I'd react. He was pretty effeminate, flamboyant, whatever, and was making sure I noticed. At one point, he started licking his lips while talking to me. While yes, this was turning me the fuck on, my friends at the chippy were all getting a chuckle, and making snide little comments. Dude didn't seem bothered, but it was, admittedly, getting under my skin. I excused myself, and ducked in the back, saying I needed to use the restroom. I told my friend I was gonna bolt out the back door, because I was obviously about to be stalked. Dammit! If only I'd allowed myself to be who I am. Who I knew I was, even then, I can pretty much guarantee he and I would have had some memorable times. I've had plenty of fantasies about him over the years.
There've definitely been more of those moments in my life, but by age 18 or 19, I'd had enough and started acting on my instincts, rather than trying to bury them. I've had a great sex life, and still do. My partner and I are married. I'm still considered good looking, and still not sure why. Lots of folks flirt with me still, every now and then some young, hot, black guy (or transgender) will, and I stop for a moment and think "Should I?"...but then I go home to my partner. I'm happy, I just wish there was a way to let my younger self know how it all turns out. "