Chapter 2 of All American Boys.
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Chapter 2
And so it went. We had found something that according to two horny 14 year olds was perfect...giving each other blowjobs. It was like when we first masturbated and couldn't stop, now we couldn't stop with the headjobs. I thought it was great that I could give my best friend such pleasure and I loved when he'd do it to me. I could tell that he wasn't as into doing it as I was, but he still did it. I took great pleasure in honing my skill. While Jeff was still stuck just around my head and threatened me every time about cumming in his mouth, within months of us starting I was able to take his cock balls deep.
It was perfect. School was out and we were on our way to high school. We were just a pair of all American boys..good looking, tanned, and ripped. We'd work out on the weight machines Jeff's dad had in his basement and if someone threw a bone, it would get taken care of. Midday we'd head to the swim club and chase the girls who were constantly after us. But this was a small city in the conservative south in the 90s. Girls weren't putting out. "Pure love waits" and all of that bullshit. We'd be lucky to get to cop a feel and even then we'd be instantly shut down. Things would have been different if we were 14 years old today, we'd have all of the pussy we wanted and then some.
But when we were done at the pool or elsewhere and blue balled from yet another uptight skirt, we'd have each other to relieve the built up sexual pressure. I liked it...I was making my friend feel good. From everything Jeff told me, I was good at it. The summer went on much this way because we didn't know anything else. We had no clue about anal sex and didn't know there were other ways to get pleasure. In our minds, we were still chasing the ultimate prize...tits and pussy.
It was the pursuit of that end that made Jeff ask me one day if he thought that's why we hadn't gotten any further with girls. Maybe we didn't know what we were doing. "You think we should practice kissing?"
I was leery...in my teenage mind, that was some serious gay shit. That's teenage logic right there...our cocks in each other's mouths wasn't gay, but our tongues was. I didn't want to do it. Jeff kept on...said that if we didn't like it we could stop. Eventually, like most things, I deferred to Jeff. I was on his bed, both of us already in just our boxers, and he came over to me and put his lips to mine. After a couple wettish pecks, I opened my mouth to his invading tongue. He pushed me back on the bed and laid down on top of me, our mouths stuck together, tongues exploring. My hands instinctively started to explore his body. That was new for us...usually it was just a mouth on his cock and hands on either thighs or ass.
I admit, I liked it. I was hard and leaking...we had our boxers on but were rubbing our cocks against each other. Our mouths were going everywhere...licking and kissing necks and ears. Our chests rubbing against each other was a new sensation...everything was new. Jeff grabbed my chest with his hand and the sensation on my nipple sent me into overdrive. I knew we were supposed to kiss girl's nipples but had no clue it would feel as good for us. I did the same to Jeff to show him how good it felt, he started griding harder into me. After about fifteen minutes, Jeff broke the kiss, stood up, and pulled his boxers off freeing his raging teenage manhood. I was prepping myself to suck him off but he pulled my boxers off and reached into the nightstand, pulling out some Vaseline.
I had no clue what he was doing but he took out a glob and coated his dick, then he took some and spread it on the inside of my thighs. I asked him what he was doing and he told me that he wanted to try something. With that, he lowered himself back on top of my and told me to put my legs together. We went back to kissing and exploring each other's bodies when I felt his dick start to go in between my legs. Jeff threw his head back and said, "I bet this is what pussy feels like." He started to thrust in between my legs which I held tighter together. His legs were spread on either side of mine and he was fucking in between my legs. I reached up and grabbed his nipples, watching his face as he moaned in serious pleasure.
He was thrusting harder and faster, I grabbed my cock and started jerking it, watching his every move. It was hot. I thought it was so hot to have this hot stud on top of me, ready to shoot at our pseudo sex pleasure. Jeff was starting to tense up and go faster, his arm shooting up to brace himself on the headboard with his armpit in my face. Still jacking myself and not knowing why I did it, I lifted my head up and sniffed his armpit. Thrusting in between my legs, he brought it down closer to my mouth and I started to lick it. It was sweaty and salty and I couldn't stop. We were both sweaty and I knew from the experience that he was getting close. I was jacking myself with all my might when suddenly Jeff buried his cock between my thighs and started to cum. He pulled his cock out and started to shoot all over me. He shot at least 6 good ropes of cum all over my stomach, chest, and even my face. I couldn't hold back and yelled out that I was cumming...Jeff jumped out of the way as I shot a load and mixed it in with his load.
Jeff laid down beside me...we were both spent. He put himself up on his elbow and looked at the cum covering me. He traced a finger through the cum and scooped some up, then tentatively held it in front of my mouth. I looked at him, opened my mouth, and sucked it off of his finger. He grabbed more and continued until all of the cum was gone. He looked at me, "I can't believe you like that shit."
I laughed and told him that it wasn't all that bad and that he should try it. "I'll leave that fag shit to you," he said. I gave him a look but right about that moment we heard the sounds of the garage door coming up, meaning his mom was home from work. Jeff disappeared into the bathroom while I threw on some clothes. Jeff came out of the bathroom wiping himself down with a wet washcloth.
"I have to go to football practice, you still spending the night tomorrow night?"
"Yeah man, that's the plan."
"Good, we'll play more then. I have some ideas."
"Like what," I asked."
"Just wait and you'll see then."
I rode my bike home to an empty house...thinking about what had happened at Jeff's I got boned up and started jerking it. It was different than before, I could still smell Jeff and the cum on me and thought about nothing but the way he looked on top of me and about how good I made him feel. I came as hard as I ever had.
Friday afternoon and I had swim practice after school so it was probably 7 before I got over to Jeff's house. His parents were dressed up and getting ready to leave when I got there, they were headed to a party. Jeff told me that his sisters were both having sleep overs at a friend's house so we'd be alone until late that evening. Perfect for us. The pizza had just arrived and we were eating when his parents left. I asked Jeff about his ideas and he said to finish up and we'd head to the basement.
We undressed in his basement and laid down in his bed. We were both horny and started making out...a days worth of pent up sexual frustration coming out. Jeff was on top of me, our cocks grinding together. I was hoping he'd do what he did yesterday again. I had been thinking about little else but him on top of me, how powerful he was when he was fucking between my legs. Jeff flipped us over and I started to work my way down his body, stopping at his nipples, sucking and kissing them. Jeff moaned and continued to push me down his body. He was already hard when I got to his cock which I engulfed into his mouth. He grabbed the back of my head and pushed his cock into my throat. I had already reached the point where I could do this without gagging but this time Jeff wasn't letting me up. I struggled against his hands trying to pull off by he held me and thrusted his cock as deep as he could. After what seemed like 5 minutes but was probably no longer than 20 seconds he let me up.
"What the fuck, dude?"
"You know you like my cock in your mouth. I'm just making sure you get all you can."
"Fuck man, take it easy."
With that I went back to sucking him. Jeff continued to keep solid pressure on my head but didn't pull down like that again. After a couple of minutes I could feel him tensing up so I increased my pace and worked my fingers on his balls. He was close, throwing his head back and fucking into my mouth. He was more aggressive than he had ever been and I was enjoying it. I loved to make him feel good. After another minute Jeff forced my head down on his cock and I felt him shooting deep into my throat. Only the last rope or two hit my tongue...I gulped the last of his cum down greedily and kept sucking on his dick until he pulled me off.
Jeff laid there for a minute spent, my head was resting on his thigh staring at his deflating cock. I thought it was beautiful and couldn't believe how good it felt. Jeff told me he wanted to show me something on the computer. We threw our boxers on and went out into the common area of the basement where the family computer was. He booted it up and started logging onto America Online. I had heard of it before but never seen it. Jeff showed me what he had found and started pulling up pictures he stored in a hidden folder. Pictures I had never thought about and never even thought possible.
"Dude, there is no way those guys are really getting fucked in the ass," I said.
"Yeah they are, you see the pictures. I want you to try it."
"You want me to put my dick in your ass?"
"No, dumbass, I'm going to put my cock in your ass."
"No way. I can't do that! You're crazy."
"I can and I will. Look at these guys, they love it. I've been reading up on it and they say it feels great. Hurts a little at first but once they're going at it it's amazing."
"I'm not doing that, Jeff."
"Haven't you said you want to make me feel good? If you really cared about making me feel good you'd try this."
With that, Jeff stood up and walked into his bedroom. I stayed at the computer and flipped through a couple of pictures. Was. Not. Going. To. Happen. But I kept looking at the pics and how the guys looked like they were in heaven, and I thought back to yesterday with Jeff on top of me. I got up and walked into Jeff's room but didn't say anything, just laid down on his bed beside him. We laid there staring at each other, not saying a word. Jeff was on his back with his arms behind his head, looking at me like he couldn't give a fuck. I was on my said with my elbow propped up and my head on my hand. Jeff wasn't breaking eye contact and I finally looked away.
It wasn't until later in life that I learned that the first person to break eye contact loses and gives in.
Jeff reached over and started kissing me. This time he let me stay on top and his hands ran down my back to my ass which he started to knead. He put a finger on my hole and started to apply pressure. Like a coy little schoolgirl, I grabbed his arm and brought it further up my back. This went on a couple of more times but the truth hurts...I was hard as a rock and his finger back there felt good. When I didn't pull his arm back up he knew he had won. He played around with my hole but didn't try to go in. Jeff worked his way around so I was laying on my stomach and he was behind me playing with my ass.
He tried to work his finger in but it wasn't going anywhere, so he reached into the drawer beside the bed to get out the Vaseline. This caused him to stretch out and when he did his dick was right at the entrance to my ass. He trust at my ass a few times and I moaned...if Jeff was in any doubt what was going to happen, this ended that. Jeff leaned back onto his haunches and took out a glob of the jelly, smearing it on my ass. He played around with my asshole and without warning jammed a finger in.
I about flew up off of the bed but Jeff grabbed me back down. "Dude, this isn't happening."
"Yes it is. You can do this."
"Then slow the fuck down."
Jeff let me settle down then heeding what I said, slowly inserted a finger in. He let it sit there and after a few seconds I couldn't believe how it felt. When I pushed back against him Jeff pulled his finger out and pushed it back in. He kept this up until I was moaning and he asked me how it felt. I liked it and told him so he went in with as second finger. The pain was good and the fullness was amazing. Jeff kept up the pressure and I kept pushing back into his fingers. I moved up onto my knees and Jeff put a third finger in. He waited a second for me to become accustomed to it when started fucking my ass with his fingers in earnest. I didn't know what he was hitting and why it felt so good but I had to have more.
"Oh man, fuck me. Shit that's good...fuck me please. Put your cock in me."
Jeff needed to encouragement. He grabbed more Vaseline and coated his cock with it. I looked back at my best friend...this teenage stud...this stud with his glistening cock who was kicking my legs apart with his knees to give himself room. This stud with his hot body who was lining up his cock with my ass getting ready to fuck me. And I wanted it, I wanted it bad. My stud was going to fuck me like I had seen in those pictures and I wanted it...I wanted him thrusting away at me. I wanted to give him the ultimate pleasure. His dick was applying pressure to my ass begging for entrance. He pulled back and slid his cock up and down my well lubed ass crack, teasing me. Each time I felt his manhood at my door I pushed back hoping he would go in. I was feeling empty without his fingers and was worried that the longer I went without the more it would hurt.
Jeff stuck his thumb in, opening me up one more time. "Aww fuck man...come on...fuck me...please...Jeff...fuck..." And with that, his cock was back at my backdoor, pressing for entrance. I started to give way and his cock made it a few inches in me. Holy shit it hurt. I tried to pull off of him but Jeff grabbed my hips and held me there.
"Don't move, get used to it." He was right. After a minute or so I started pushing back. It was slow going but I had never felt so full or so great. Jeff kept the pressure up and kept slowy going into me until finally I felt his pubic hair against my ass. I felt amazing and looked back at Jeff with lust in my eyes.
"How's it feel," Jeff asked.
"It feels amazing...I didn't think it would feel this good."
Jeff reach up and put his hand on my shoulder, "Good...I'm glad you like it. Now get ready to get fucked."
In part 3:
Jeff looked down at me, "look, I've been reading up on this stuff on the computer and usenet...there are guys in this world that like this gay shit like you and there are guys in this world like me that don't care where they get their nuts off. You can't expect a guy like me to worry about how a guy like you feels."