My sister, who is a year older than me, always had good taste in boyfriends. I liked every one of them, but a few of them stand out.
When I was sixteen she had one named Richard who was nineteen. Mom normally wouldn’t have approved because of the age difference, but she said Richard was a nice boy from a good family, which meant they had more money than us. Richard wasn’t nearly as nice as she thought, but he was gorgeous. At that time I was in my pre-jock phase and no one had any idea of the thoughts in my head or the desires that stirred my loins.
Richard lived on the other side of town and Sis had met him at a basketball game between the two high schools that were in our small town. He had a driver’s license, but it had been suspended for driving with too many kids jammed into the car. Therefore he had to take the bus to visit our house, and since Sis had an early curfew most of their dates were weekend afternoons or just at the house.
One Friday night they had been sitting out on the porch necking. Mom was busy doing something like straightening out a bank balance problem or taxes or something that had her mind completely occupied. She had forgotten Richard was there or some such, or they wouldn’t have gotten so deep into petting, and Richard would have been sent home long before.
When she became aware of the time it was too late to make him take the bus home, so she told him he could spend the night if his parents said it was OK, but he’d have to sleep on the downstairs sofa. I said he could share my room, I didn’t mind. She asked him if he minded sleeping in the same bed as me, and he said no. BINGO!
When I came out of the bathroom after brushing my teeth he was sitting on the bed in his briefs and so instead of putting on my pajamas I stripped down to my briefs.
“Which side of the bed do you prefer?” he asked.
I grinned, “I don’t care. I’ve never had to choose before.”
He stood up and I was blown away by his body, and the huge bulge in his briefs. He saw me gaping and said, “Your sister is so HOT. My dick is so stiff it might break off.”
He pulled down the covers and said, “Hop in. I’ll sleep on the outside so you can’t escape if I decide to rape you.”
I climbed in the bed and turned to get a last look before he got under the covers.
He climbed in and said, “If you feel something poking you during the night, that’s just my hard dick.”
I realized my dick had already gotten hard, and I was dying to see his big hard dick. After all, something like that had been the intention of getting him in my bed. I just hadn’t had a concrete plan. This was my very first experience with another guy, and I didn’t really have any idea of what I was doing. I was lucky that I was with a dirty minded horny guy.
Richard continued, “If I wake you up it’s just I might have to jack off to get rid of this hard-on.”
I said, “I don’t care if I can watch.”
“Oh hey, that’s a hot idea. You really wanna watch me do it?”
I threw the covers back. He had pushed his hand down under the waistband of his briefs and was squeezing his dick.
I said, “Do it.”
He pushed his briefs down almost to his knees and his big dick sprang free. I reached over and wrapped my hand around it and he took a quick hard breath.
“Wow, you like it?”
“It’s really big,” I said.
He moved my hand away and began jacking his dick, slowly at first but quickly doing it fast and hard, his whole body tensing. I was fascinated, but I wanted to be part of the action, not just a spectator. I scooted over nearer to him and when he slowed down I again put my hand on his dick. He let me take it and after a minute of jacking it, when I thought he was going to take back over, I bent forward and covered it with my mouth. He gasped and moaned and I bobbed up and down on it.
He said, “oh yeah, suck it. Make me cum,” and put both hands on my head, sort of using my mouth to jack his dick off.
I hadn’t even thought about his cumming, but when he did I liked it, both in the way it felt and in his guttural sounds of satisfaction.
When we could talk again he said, “Holy shit, that was super fantastic. D’ ya like it?”
“Yeah, that was fun.”
“Fun? Huh, it was more than that. Nobody’s ever done that to me before. Thanks.”
He pulled his briefs back up and turned his back and was asleep before I dropped off. The next morning he didn’t say anything, but I jacked off to the memory for a long time.
The thing with my sister was a typical teenage romance, and by fall when he had gone away to college my sister had another boyfriend. Over the next two years, she had half a dozen, none serious, but all nice to look at and dream about. But I did more than dream. I had two of them.
One was Gerald who was eighteen and a tall lanky basketball player. He also had a long dick. Sis wasn’t too into him, but he kept hanging around, hoping. I got him to show me how to make some shots, and he was happy to show off. Then I started blocking him and bumped and rubbed up against him so much he got an erection…and the message. When his hard-on was clearly visible and he couldn’t hide it, I groped him.
He froze and I said, “Let’s go in the garage.”
Once there he put up no resistance while I felt him up and then unzipped his pants. He pulled his dick out and I got on my knees and started sucking. I unhooked his pants and he let me pull them and then his floppy boxers down. He grabbed my head and I thought he might collapse on top of me, so I got an old blanket that was wrapped around a piece of furniture and we lay down on that. He humped his hips, jabbing his dick into my mouth. I didn’t have much experience, but he had less. He really didn’t know how to do it, but I still liked sucking him off and eating his cum.
But he never came around again. I think he was probably embarrassed, which is funny since I was the one who sucked him.
The other boyfriend I made out with was also eighteen. He was a more serious boyfriend than Gerald had been, and he was always grabbing and wrestling with me, calling me a pest and a punk. When he had his arms wrapped around me in a hold I couldn’t break free from I’d push back against him, trying to feel his dick with my leg or butt.
It was all in fun and I loved it, but I think Sis was annoyed with the attention he gave me. Since Sis was a little older Mom gave her a little more freedom. I told Gabe if he stayed too late and missed the last bus home he could always bunk with me. It was an open invitation and he seemed interested, or was it my imagination?
He had said “Thanks.”
It wasn’t long after when he somehow managed to overstay his time and then loudly fretted about how he was going to get home. Mom wasn’t too happy, thinking she was going to have to give him a ride, but I jumped in and said he could share my bed like that other boyfriend of Sis’s had done once.
When we were in my room he was getting undressed when he told me he hoped it wasn’t a problem but he always slept in the nude.
I said, “Really? That’s amazing, me too.”
His body was even better than Richard’s, but his dick was smaller than his and Gerald’s. Not little, just smaller. Before we even got in bed he started punching, pinching and tickling me, and then got me in one of his wrestling holds, pressing and rubbing his dick against me. My dick was beginning to grow, and I was afraid it was going to get hard and embarrass me. I loved his holding me, but I broke free and jumped in bed.
He got in too, but still tried to grab me. I was laughing so hard and loud Mom yelled for us to knock it off and go to sleep. We stopped wrestling and sort of giggled and he found my hand and put it on his dick, which was hard.
“Do you like how that feels?”
I nodded.
“I thought you would.”
I was curious. “Why did you think that?” I asked. Nobody had ever even hinted at it before.
“My cousin likes to do it to me.”
I hadn’t done anything to him yet, but I knew what he meant. “Do you want me to?”
“That’s what I’m here for.”
I scooted down under the covers and took his dick in my mouth. He almost at once grabbed my head and made me go up and down while shoving it in and out, but not like Gerald did. He knew how to do it, and I learned some things.
After maybe ten minutes he asked, “Do you have any Vaseline in the bathroom?”
“Yeah, why?”
“Just go get it and I’ll show you something new.”
I jumped out of bed, opened the door and peeked out to make sure the hall was clear and ran to the bathroom with my hard dick bouncing around.
When I got in the bed he said, “Get up on your knees. No, like this.”
When I was in the correct position he smeared the Vaseline all around and in my butt hole. I was so green I didn’t know what he was going to do, but I soon found out. It turned out I was glad his dick wasn’t as big as Richard’s because when he pushed it in I felt a definite burning pain.
I said, “Ow! That hurts Gabe, stop it.”
He stopped pushing but didn’t take it out. “Wait a moment. Try to relax and it won’t hurt. That’s what my cousin does. Isn’t it getting better?”
I thought about it. “Yeah, a little.”
“It’ll feel good in a minute. Push back.”
I did and the rest of his dick went in.
He kind of croaked out, “Damn, that feels good, you’re so tight. I’m gonna fuck you good.”
He started slowly pulling his dick out and then pushing it back in.
“Doesn’t that feel good to you? Don’t you like my cock in your ass?”
I didn’t answer because I was too busy thinking how great this was. He picked up speed and was fucking me so hard I couldn’t stay on my knees and collapsed onto my stomach. He spread my legs wide and continued until he suddenly stopped going in and out and made a series of short jabs, each time going, “Unh, unh, unh.”
When his dick went soft he pulled it out slowly. “You got anything I can wipe my cock with?”
I got out of bed went to the bathroom again, feeling cum coming out of my abused butt hole. I used a couple wads of toilet paper to wipe me clean and then took several dozen sheets back to him.
“Here,” I said.
“No, you wipe me off.”
I did, but then he took the wad and did it to his satisfaction.
He looked at me and grinned. “Did you like that?”
It was my turn to grin.
As we got under the covers and I turned out the light he snuggled up to me and said, “Next time I’ll show you how to sit on it.”
There was never a next time. Sis broke up with him and refused to talk about it, and I couldn’t question her too much. But I was soon seventeen, and she went off to college. Then a new guy moved into our neighborhood. He was a couple months younger than me, his name was Dan, he wasn’t gorgeous but he was nice and we became friends.
I guess there was some sort of secret unspoken code or something because it wasn’t long before we were sucking each other’s dicks and a little more before I told him about Gabe fucking me and we tried that. It took some doing, but we learned how and would take turns fucking each other.
Dan and I continued doing everything for two years, until we graduated from high school and also went off to college, but different colleges… and I grew into a functioning gay guy.
When I look back on it, it’s amazing to me how all of this just sort of happened with no instructions. I mean I did everything on my own with no foreknowledge or guidance, except for what Gabe taught me. It just came natural, I guess.
When I graduated from the university I was given the opportunity to do post-graduate work in Europe for a year. During that year Sis got married and moved to Houston. I was told he was a really nice guy, but I never met him because less than two years later he was killed in a car crash by a drunken driver. Sis was devastated and went into a long period of mourning.
