TRUE FIRST TIME TALES
Jason's Tale
This is the story of the first time I had sex with a guy when I was in eighth grade.
It was late in eighth grade. I had this friend who was pretty girly. We had been friends since I moved into the apartment building in Lisle when I was seven. We became friends, and stayed friends when school started. I was never one of the popular kids either, so we got along great. We made other friends at school and even in the apartment building. I had closer friends, but he didn't seem to.
He lived with his grandmother, because his parents had died in a car accident when he was four. She was pretty sick and weak, and almost deaf. She could hardly get out of the apartment. Hell, she could hardly get around the apartment. She had to use a walker to get to the bathroom or kitchen. So he did almost all the shopping, cooking, and cleaning. We both became nerdy students and got great grades. We helped each other with studies and homework and all that. We liked mostly the same movies and music and books our friends did.
He was always a little taller than me, and when puberty hit, he was first and stayed a little taller. We were both lean and trim, certainly not the jock types. As we hit puberty, and our friends got interested in girls, I know I faked that interest. Sometimes it seemed Jacob did too. My other friends said Jacob was queer, and he acted girly enough that it was hard to defend him. I started getting crap for even being his friend from some of my other friends. But I like Jacob, and I didn't avoid hanging out with him at school. Sometimes I picked hanging out with him at his apartment with his grandma over going out and hanging out with my other friends because I really liked him. Especially when puberty hit in seventh grade and I started to really be attracted to him.
He had curly blond hair, deep blue eyes, and a long, smooth face and body. His smile was nice, with nice lips and little dimples. Puberty made his ass fill out some, but it was never really round or anything. It also made his package fill out quite a bit. I had never had gym with him, so I had no idea what he looked like naked. I sure imagined it a lot though after I started getting horny at thirteen.
So during eighth grade I spent more and more time hanging out at his apartment. I even stayed to help cook and then had dinner with them several times a week. I started staying over on weekends more than with my other friends. They started saying we were being queer together. So I stopped being friends with some of them. I liked Jacob for a lot of reasons, not just that I was attracted to him. He was smart, and kind, and caring, and gentle, and didn't act high-and-mighty or superior. And he was pretty brave, too, in his way.
Sometimes after school, I would go to his apartment instead of to mine, so we could work on homework. He always changed out of his school clothes first thing. It was no big deal at first, but then puberty hit, and it got more interesting to me. He started puberty first, in seventh grade, and was bragging about pubes and his growing dick and squirting off when he jerked it. I finally could too over the summer after seventh grade. He never took off his underwear. In those days we all wore white Fruit-of-the-Looms, so I got a good view. In eighth grade, I pretty much went over to his place after school every day.
Late in eighth grade, I was staying over on a Saturday night. We cooked meatloaf and mashed potatoes and green beans with garlic bread. We watched a movie with his grandma, and she went to bed about nine. We watched the Saturday Night Chiller Feature at ten-thirty, then played some video games in his room. He always slept in his underwear, and I usually slept in my tighty-whities at home, but in sweatpants over at his place. I slept on the sleeping bag on the floor at his place, he used it at my place. I always beat it off after we turned off the lights, usually pretending we were beating each other off in the dark. Sometimes I swear I could hear him doing it. I promised myself that someday I would talk to him about it, and see if I could get him to with me. I was sure we both knew the other was doing it. I just wasn't sure if he was interested, even if he did seem kind of girly, or maybe gay. It was just too scary and too risky.
So that night, after the monster movie, we got ready for bed, and I decided to only wear my underwear. Then we played video games on his bed in just our underwear. His grandma never came to check on us after the first few times I stayed over. Besides, it was hard for her to get around, and her room was right across the hall from the bathroom, so we weren't worried she would come in and see us sitting in our underwear.
It wasn't a big deal if one of us boned up. It happened all the time anyway. We'd sometimes joke about it, but that was about it. But the last couple of times, he'd kind of looked longer than before. And I had noticed. And I had always looked as often as I could. So I wore just my tighty-whities this night. There was no mistaking he had a nice big one. Not very thick, but pretty long. And his balls looked pretty hefty, too.
He won the game we were playing, when I noticed he was boned up. I was getting desperate to find out if he was gay, or at least interested in doing something together. I'd heard about guys doing jerk-offs together, and I was trying hard to think of a way to get him to. So I was boning up too.
It was really awkward and weird, us sitting there, boned up, the game over, and us looking at each other like idiots. We were both laughing stupidly.
Then Jacob asks, "You ever thought about beating it off together?"
I was so shocked that I totally froze up. I was about to ask something like, 'What do you mean?' when he said, "I mean, you know, at the same time? Because I know you do after we turn out the lights. I do too."
I was pretty sure he knew I did. I sometimes thought I heard him doing it. That was something I had thought about saying to him anyway, in hopes something might happen if I did.
So I screwed up the courage, and said, "Yeah, I hear you beating off, too."
After a few seconds or so, he said, "So let's stop pretending we don't."
"Okay."
He got really red-faced, and smiled, and said, "I got something."
"What?"
He reached under his mattress, and pulled out a porno magazine. I was shocked.
"How'd you get that? And when?"
I was pissed he hadn't shown it to me before. I thought we shared everything, sort of.
"Lifted it from behind the counter at the drug store," he said, laughing. "When I knew you were staying over this weekend."
He opened it up, and we started looking through it. It was the first pornography I'd ever seen. Back then, cable was for the rich folks who owned a house, not everyone. And computers were clunky and had green text and no images.
We sat right next to each other, our arms touching, our thighs touching with just the thin material of our briefs between our warm hips, both of us holding open the magazine between us. Our arms closest to each other were on our own thighs. I thought of how close my hand was to his boner, and my own bounced and twitched.
We went all the way through it, giggling and pointing, and adjusting our pricks. Then we started through it again. The naked women were okay, but pictures with naked, hard guys were amazing. This time through the magazine, I noticed that he paused on the pictures with the guys longer than the ones with just the women. That really made me courageous and hopeful when I noticed.
"You like the pictures with the guys?" I asked, my face burning and my guts churning.
He laughed, got more red-faced, and nodded, then said, "It's sexier when there's action."
I agreed with him, and wondered if that was really the reason. A lot of my friends said he was queer, and he was kind of girly, especially when we were alone and he dropped his guard, I guess. Where the courage to say what I did next came from I don't know.
"I like the action, too, but I like seeing the guys, too."
I could barely look at him, but when I did, he was smiling his big smile, the one with the dimples.
Then he asked, "So, you wanna?"
"Jerk-off together?"

