In late middle school I knew I had a problem. I knew I was quite attracted to boys my age, and not so much to the girls. Frankly, I wasn’t attracted to girls at all. They scared me because I didn’t know what to make of them.
I remember wearing sunglasses so that I could look at the boys swimming in the public pool without them knowing that I was looking at them. On the rare occasion when I saw some pornographic pictures, I’d like seeing the erections, but when I saw a woman’s vagina, it looked like a wound to me.
Once I learned to masturbate, which I figured out on my own, it was images of boys that turned me on. The first time I orgasmed, only one clear drip came out. I wasn’t very informed about sex, but I sort of knew what it was. I was also freaked. Like most kids in those times, I was under the impression that masturbating was a very bad thing. I didn’t quite know why, but I knew it was bad. Everyone said so. “Thanks parents, thanks society!” – I say cynically, now.
As “bad” as it was, it didn’t stop me from jerking off pretty much every day. That first time I came, I had done it by pressing the thumb and first finger against each hand against the sides of the shaft of my penis and moving up and down. For several months, I thought that this exact same grip was required, and did it that way every time.
Nothing happened with anyone but myself until high school. Then, I started jerking off with this very heavyset friend of mine. We took it to the point where we’d give each other handjobs. That’s all. I believe it was he who approached me about the idea of jerking off together. I wasn’t attracted to him, but he was a good friend. We did lots together, like talking endless about when we’d have cars someday and what kind they’d be. We both talked very authoritatively about girls, trying to insinuate we had experience, without actually saying anything.
Sometimes, while jerking the other guy off, we’d pretend his penis was a gearshift, and we were driving a car.
Diane came along. She was always talking about sex, and I know in retrospect she wanted to get into my pants. I was so oblivious that it never happened. But her brother, he was a late developer, he and I masturbated each other all the time. Soon he could get to the point where a drop of cum came out of him. By then, I had hairs around the base of my dick, and could cum in greater quantity. He and I would take the hollow pieces of a plastic chess set, and see how much semen we could pump into them. The last time I saw Benny, he was able to fill a pawn. I could almost fill a queen.
In my last year of high school, by now driving a beat-up old foreign car with a worn out transmission that required double-clutching, I met June. She was five years older. She was a small Asian chick who had the unlikely job of driving an 18-wheeler. I fantasized day and night about driving a big truck, and here she was actually doing it. I dreamed of trucking almost as much as of sex – still mostly with guys, however. That bit, about guys, was my big secret.
June looked a lot like Lucy Liu
One day, June said the company needed co-drivers, and the only thing required was a truck driving learners permit and being 18-years old, since there’d be a fully licensed driver in the truck. I was all over it, and got my permit the next day.
The first time out, we had a ten-wheeler with a ten-speed transmission. I was disappointed that it wasn’t an 18-wheeler, but so totally happy to be driving any sort of truck. June drove the first hundred miles. I was wondering if she’d let me drive at all. Then she pulled over and we switched seats. Because the old car I had, and because I had studied up on it, it didn’t take me long to figure out how to shift gears in that truck. June was very careful to instruct me in how to take corners so as not to run the back wheels over curbs, or worse. Still, I almost clobbered a stop sign while making a right turn. After that first 100 miles, she never drove again. She was delighted to have me do all the work.
They were two-day runs. We had to stay in a hotel overnight. All the first afternoon, I was trying to figure out how that was going to work, and assuming we’d rent two rooms. It turns out the company would only pay for one room. Interesting, eh?
By the way, I have to tell you, I was finding Junie rather attractive. She was more like a boy than a girl in many respects. She had short hair for a girl, and fairly small tits. I especially enjoyed her mouth. She could swear up a storm, which I found rather impressive at the time.
So that night, we were in our separate beds, and talking. She kept bringing the conversation around to sex, which I was fully on board with. I was too shy to do anything more, but not Junie. Suddenly she threw off her covers, and climbed into my bed. Awkwardly removing our clothing, we started rolling around and kissing. She totally wanted to fuck. So did I. However, I couldn’t get it up. I know now it’s called ‘performance anxiety.’ Plus, all my life up until then, thinking I had to keep my gay side secret, I was very careful not to spring boners at inappropriate times, like in the boys’ shower at school. So, I had accidentally taught myself not to get hard around other people, even when it’s OK. June was disappointed, even though I was able to bring her to orgasm with my fingertips. To say I was disappointed would be a huge understatement.
On the next drive, two weeks later, we had an 18-wheeler with a Spicer 13-speed transmission. I was delighted. It was larger and harder to manage than I imagined, but I loved learning to drive that thing. We stayed in a hotel again, and that night everything worked perfectly! To my surprise, I found Junie very attractive, and had a great time. That first time, I kind of thought of her hairy vagina as unattractive. Not this time! I was happy to lick it, and loved the taste. I fondled her breasts for a long time as well, which not only did she like, but I loved. I ejaculated inside a vagina for the first time in my life.
During the next few years, I still thought I was hopelessly gay. In those years, that would have been a bad thing, or so I believed. Homosexuality was not as accepted, at least in my circles, as it is today. To satisfy my desires, I had occasional experiences in bathhouses, and with the occasional guy. I met a gay plumber. Unlike me, he wasn’t keeping it a secret. I was surprised he could be so open about it and remain functional in society. Carl was very attractive to me. Slight of build, and blond-haired. He was rather feminine in build, but didn’t act that way. In all other respects, he was a ‘guy,’ drinking beer, following sports, swearing, working hard at manual labor, and so on. When we got into his bed, I was suddenly very uninterested in kissing or oral sex. All I wanted to do was handjobs. Fortunately, he was understanding. We got together a few more times, and then drifted apart.
Carl bore a resemblance to David Spade
In my late twenties, I had sold a business, bought a motorhome and traveled around the country. I met various guys, and the occasional girl. One was Amy, a very small, curly-blond haired woman, not unlike a young Meg Ryan.
Amy was a handjob expert. She liked sticking her skinny little finger into my peehole, which kind of hurt, but felt very exotic at the same time. One time, I ejaculated while her finger was in there. It scared me, because I thought the cum had to come out, or I’d burst something, but no, it was just fine. In fact, the orgasmic contractions lasted twice as long. She wanted me to put a finger in her ass, which I did reluctantly. When I pulled it out, I noticed a sweet odor, not at all what I would have expected. I put it back in, and felt her contractions when she orgasmed from the attention my other hand was giving her clit. From then on, I was a big fan of anal fingering.
I met a rather overweight Inuit (Eskimo) woman. She was great fun, but I thought I deserved better, so I cheated on her. She threw me out instantly, which I’ve always regretted, because she was great company. The best conversationist I had ever met. Also, a sexual monster. She loved having cucumbers shoved into her ass, and taught me to enjoy that as well.
I hadn’t been doing much of anything with guys, except for Larry. He was 18 years old, mostly heterosexual, although still a virgin. He and I started giving each other handjobs on a fairly regular basis.
Then I met Cindy. She was a true nymphomaniac. Every guy’s dream, right? Not so! She wore me out. She’d want to fuck at 11pm when I was sleepy, but I’d comply. At first it was fun. But then she’d wake me at 3am begging me for more sex. And then at 7am, she’d gently wake me again, and – you guessed it – wanting more. I tried to dump her several times, but the tears would come, and I would relent. I introduced her to Larry, figuring he’d get his first experience with a woman, and I’d get some relief.
The first time was a three-way. I probably should have held back so Larry could have a normal first experience, but I didn’t. I put my finger in her vagina while he was fucking her, which she loved. He probably wanted it simpler, but didn’t complain. I mean, after all, he was having a great time. Then, when he was about to cum, I stick my finger in his ass. He orgasmed so hugely that he was shaking all over, and practically fell off the bed, almost taking Cindy with him.
They hit it off big-time. I lost Larry as a wank buddy, but also got rid of Cindy who was becoming a big problem. As the two of them rode off into the sunset, I cooled down for a year or so, being happy just to jerk off once or twice a day.
Then I met Carol, who drove me fucking crazy. She was a perfectionist, and it overflowed into trying to control me. Like while having sex, she’d keep saying, ‘unh, uhh,’ or ‘yes,’ guiding me in exactly what she wanted. The prudent thing would have been to dump her early, because she was rather bothersome. But instead, I found myself more and more drawn to her. She was very intelligent as well as intuitive, and although she could get intense at times, she was a great and helpful companion. That was 26 years ago. Carol and I are still happily married with two beautiful grown children, who, due to Carol’s way of guidance, are already very successful adults.
A few years ago Carol went through menopause and lost interest in sex. She knows about my bisexual background, and has encouraged me to play with guys whenever I like. She absolutely doesn’t want me to get sexual with any women, however. I’m not sure why the double-standard line exists in her mind, but it does. So, every month or so, I hang out with Tom, who is a few years younger than me, built like a Greek god, and loves exchanging handjobs.