Winning Team

I don't think Joe and I even knew what we doing. We were just swept along with an intense friendship and a good dose of teenage lust.

We'd spent a lot of weekends and summer evenings over at each other's house. My parents considered Joe family and the Massaros did the same with me.

It was between sophomore and junior year when we first started fooling around. It had been a long day, working out, practicing throwing, hanging out in Joe's pool, and dinner with the Massaros. I spent the night over there as I often did, and Joe and I stayed up late in his room, talking. Our talk turned to sex and pretty soon we decided we'd experiment. We gave the other our first blow jobs. We didn't know what we were doing, but we both came quickly and knew we wanted to do more.

No one thought anything about how close we grew. We were two jocks and the pillar of a winning baseball team. Rockford might have been a football town but five years ago Kyle Collins' kid Tony lived up to his major-league dad's potential and put our baseball team on the map. Coach Helson continued to deliver championship teams, even after Tony graduated right into a big fat MLB signing bonus.

Neither Joe Massaro nor I were that caliber of player, but we were the best on the team. Joe a power-hitting second baseman, me a catcher with the best record in the state.

Joe was an incredibly handsome guy. Tall at 6'3", with a disarming smile and soulful brown eyes. He'd put on more muscle the summer before senior year and was close to catching up with my 195 pounds. I had a typically endomorph catcher's build and my growth spurt had hit a year before the other guys, aided by my love of working out.

It was the first week of senior year when we tried fucking. We'd sucked each other off in my bedroom after dinner, while my parents thought we were playing video games. Afterwards, we talked about girls we wanted to date, about how bad our football team sucked, and about colleges we were going to apply to.

"Think we're going to get scholarships to play, Zach?" Joe asked, reaching down to adjust the genitals lying softly in his shorts.

"No doubt, Mas'," I said. "Just a question of where."

"Probably not at the same place," he said, a little sadness in his voice.

"Probably not," I said. "But that would be cool."

Joe looked at me with a look I could only describe as affection. Our faces inched together and we kissed, for the first time. This felt different than the blow jobs and mutual stroke sessions we'd shared before. Or maybe I was just owning up to the emotion that was already there.

Massaro's strong hands were already tugging my shorts down, and I did the same. Pretty soon, our bodies were nude and pressing against one another as I rolled on top of Joe, my thicker cock pressing against his longer one.

"Wanna try fucking, Mas'?" I asked. I was keyed up, sexually and emotionally.

He nodded. "Sounds pretty wild, but yeah... I wanna try that with you." He gave me a concerned look. "You got stuff?"

I hadn't thought to plan anything. "I got some vaseline I use to stroke off with. That's it."

He looked at me thoughtfully. "That'll do," he said softly. It was a trip seeing my stud second baseman friend beneath me, looking up in sexual excitement. "Um... so who goes first?"

"Flip a coin?" I said. "I wanna try it both ways."

Joe seemed relieved by my answer. And I knew why. Neither of us wanted to be the other's bitch.

I got up off the bed and grabbed a quarter. I probably looked ridiculous standing there with an erection getting ready to toss a coin. "You call it, dude."

"Heads," he said right before I flipped the quarter in the air. It landed in my hand and I flipped it on my forearm.

"Tails."

I was secretly glad I wasn't taking dick first. Joe looked nervous but had an expression of agreement. He wasn't the kind of guy to back out of an agreement.

The vaseline felt thick on my finger tips but it softened as I applied it to Joe's hole. He lifted and spread his legs to let me get at his ass, and he even seemed to enjoy it when I pressed my finger inside him.

I don't think I'd been truly excited to fuck Joe Massaro until I felt the heat and tightness of his hole. It seemed to suck me in and I anticipated how snug it would feel along my bone. I pressed a second digit in. Joe hissed but nodded up at me, telling me he was OK. "Another," he finally instructed me.

Finally, I knew I wanted to try this. Wanted to get inside Joe's ass. I greased up my prick and guided it to the jock's hole. He was tight and gave me some resistance but I was surprised at how easily I sank in.

"Fuck," I grunted as I bottomed out.

"Jeez, Elliott," he said, using my last name. "You got a fat cock."

I leaned down and kissed him. The romantic connection was still there, but our horndog excitement was now front and center. We made out and I fucked my best friend. He took it, too, feeling up my body and guiding my hips through the thrusting, tell me he was good for what I could dish out.

Knowing that, I went at him harder. This was the best sensation I'd ever felt, his baseball jock hole practically milking my hard cock, sucking the load from my balls. I spurted good and heavy inside Joe. The orgasm was so good I felt like I could pass out.

Instead I held myself steady above my teammate and best bud, savoring the emotional weight of our first fuck.

"You good, man?" I asked, concerned maybe I'd gone too hard.

"Fuck, yeah, Elliott. Only I need to get off. And I believe it's my turn."

I nodded and pulled out, feeling the sticky slickness of petroleum jelly and my cum mixed into a froth. I plopped down on the other side of the mattress and spread my legs like Joe had done. He was eager as fuck and quickly scrambled into place, dipping his fingers in the tub of Vaseline.

Thankfully the sex had loosened my inhibitions and Joe didn't have to finger me for long before he pushed my thighs back and pressed forward, penetrating me in one smooth motion.

"Oh FUCK!" I grunted. Not in pain, but it was a weird, not entirely pleasant sensation.

Joe's cock was long and I felt it deep inside my guts.

"Shh..." he admonished. We had to be quieter. I think Joe wanted to slow down but he was real turned on now. He humped excitedly, and the insistent pressure of his dick up inside me was starting to feel pretty amazing. I thought this would be about turning the tables and that was it. But as Joe fucked me I got hard, real hard, and knew I was going to cum again.

It was Joe's kiss that did it, sent my second load firing out between our heaving bodies as my teammate and friend dumped his inside me.

We fucked a lot after that. Usually once a week, on the weekends when we thought our parents wouldn't catch us. Luckily our folks generally respected our privacy. During the week Joe and I might swap blow jobs, but if we had that time together on the weekend, we'd flip a coin and the winner got to do the fucking.

I hadn't admitted it to Joe but as much as I loved fucking his tight Italian jock ass, I think I even liked it better when he did me. His long prick seemed to hit a spot inside me that got me off big time. I'd jerk my dick as Joe shafted me with long strokes, his handsome face looking down on me, lusty and encouraging at the same time. As soon as I came, he'd go for his nut, too.

Occasionally Joe would come while getting fucked, too, but usually I went down on him after I got off inside him, or maybe would kiss him as he stroked to his climax, our sweaty bodies side by side.

It took a special occasion for us to fuck on a weekday. It was a spring Tuesday, and I had received a scholarship offer. I called him up after announcing the news to my parents.

"Dude," he said before I gave him my news, "I just a full ride from Florida State."

"You're kidding," I said. It was so incredible as to be unbelievable.

"You don't think I'm up to snuff, Elliott?" he said, half teasing but maybe a little annoyed.

"Bro, you're definitely up to snuff. It's just.... I got the same phone call today."

"Shit.... really? Fuckin A!"

I knew immediately what I wanted. "OK if I come over?"

"Let me check." Joe was definitely on the same wavelength. After asking his parents he said, "Yeah come on over."

I greeted Joe's mom when I got there.

"He's up in his room. He's been excited as a kid all afternoon," Mrs. M beamed.

"Yeah," I said, trying to contain my enthusiasm. "I got some similar news today, too, Mrs. M."

She gave me a hug. Like I said, the Massaros treated me like family. "We'll have to take you boys out for a nice dinner to celebrate. I'll talk to your mother."

"That'd be awesome, Mrs. M. Thanks." As much as I enjoyed sharing my news with her, I was itching for something more. "OK if I go up and see Joe?"

"Go right ahead."

"Thanks, Mrs. M. I wanted to tell Joe the news in person."

I rapped lightly on his bedroom door and opened it. My teammate was there waiting for me, an excited look on his face.

"Holy shit, bro," he said, stepping up to me and giving me a deep kiss. It felt right. The best way to mark the occasion.

"I'll lock the door," he said. "You can flip the coin."

I pulled down my shorts and stripped off my shirt. I was erect from the kiss and the anticipation alone. "Forget the coin, Mas', you can take heads."

Joe's eyes twinkled. "Yeah? You gonna be my catcher buddy?"

Part of me groaned at the comment. When you're a baseball catcher you hear that joke like a million times. But I was horny and in heat for my friend. "Yeah, Joe. I really like being on the receiving end, if that's cool with you."

Joe was now naked and hard, and smothering vaseline on his long beautiful cock. "That's way cool with me." He got up on the bed, his thick hardon leading the way. He was ready to fuck for sure. "So... we talking just this time, or...."

"Any time, Mas. No more coin flips."

That brought a big smile. "Awesome." He scooted forward and entered me. Normally he took his time. Joe was really good at prepping me. But today I didn't need it, and Joe somehow knew. He sank his long dick right up into me, where I wanted it. Where it belonged.

Our lips met as he bottomed out. "You're so good at this, buddy," he growled as he started kissing along my cheek and the side of my neck and as I held on to his strong body. "You feel so good around my cock."

"I was afraid you'd think I was your bitch or something." I was torn. I wanted to bottom for Joe Massaro and to tell him how I preferred it that way. But I didn't want him to think less of me.

He gave his first thrust into me, gentle but insistent. "Buddy, you can be what you want to be with me. I'm grateful every time I fuck you."

The honesty and directness of his words turned me on. And soon he was raising himself back into a kneeling position, my legs on his shoulder, his dick nailing me. God, it felt exquisite. My own prick was rockhard and leaking on my belly.

I'd always been attracted to Joe, but the last year he'd really become an unbelievably hot fucker. Tall, with the right amount of muscle for a college-bound player, impressive cock. He was gonna fuck me off, past the finish line, and soon.

"I love you, Zach Elliott," he said, his own rising orgasm clear in his voice.

"Oh fuck, I love you too, Mas'," I grunted and then I felt it. Hot spurts of my semen jetting out all over my chest and up to my neck.

Joe growled quietly and leaned forward for his final hard thrusts, coming deep inside me.

He didn't pull out right away, not like usual. Instead he held himself buried in me and looked down on me with a smirk. "We're gonna have a lot of fun at college, Elliott," he said.

And like that he started thrusting into me once more, gently, and I had a good feeling that both of us were going to get off again before I headed back home.