The usual disclaimers apply, if you're not old enough to be reading this, or if consensual sex between teenaged men offends you, please don't read on!
Hey there guys, this is my fourth story up here, it's a bit different from my other ones, this one doesn't have the usual domination subplot. It's actually based on a rather memorable sleepover I had in my teen years! As always, I love to hear any comments, questions, complaints or dirty stories! E-mail me at subboyns@gmail.com
I had long had suspicions about my friend Matt. He was very pretty for a boy his age, thick brown hair, very lush lips, long eyelashes. He was still masculine and all, but damn was he gorgeous. We'd been best friends for years, but lately my thoughts of him had turned from friendship to lust. We were having a sleepover to celebrate his 15th birthday, and his parents were going out for the weekend, giving us the place to ourselves. A plan had formed in my mind of how to take advantage of this, to finally determine whether he was gay or not.
Of course, my horniness wasn't helped by the fact that we were together almost all the time, at school, after school, the weekends. We were into all the same stuff, we played the same sports, liked the same video games, we even looked similar, even though I kept my hair a little shaggy and didn't have his gorgeous eyes.
Soon enough it was Friday night. It was a chilly February night, and Matt answered the door a sweater and jeans, looking preppy but sexy as hell. The tight black sweater showed off his developing form quite nicely.
"Come on in Joey!" He led me inside, and helped me get my jacket and shoes off. I had dressed similarly, a red sweater and khakis.
"So what's the plan for tonight?" I asked, already knowing what he had in mind.
"Video games and pizza till we pass out?" He said excitedly.
I laughed. "Sure thing buddy."
We headed down to the basement where his Dad's gigantic TV was, and Matt started to set up his Playstation.
"Hey, I'm gonna go toss my shit upstairs." I said, gesturing to my bag.
"Sure thing." He said, engrossed behind the TV.
Time for the first part of my plan. Matt had always worn briefs, even when all of our friends switched over to boxers. He said that they just felt better on him. I disagreed, I thought boxers were more comfortable, but I loved the look of briefs, especially on Matt. I had decided that tonight, I was going to wear a pair of his.
I tossed my bag into the corner of his room, seeing the air mattress set out for me on the floor next to the bed. I went to the top drawer of his clothes chest, seeing his underwear collection spread out before me. Briefs of all colors and styles. I knew what I wanted, a small pair of white briefs. I went right to the bottom of the drawer, trying to find an older pair, well worn in.
I found one, perfect for what I wanted, and went to the bathroom to change. I slipped out of my khakis and boxers, and stepped into the briefs. I was half hard already, so I tucked my dick off to the side of the briefs. I shoved my boxers inside my bag, and went back downstairs.
Matt was spread out on the floor in front of the TV, waiting for me.
"You get to pick the first game." He smiled. I could have jumped him right there. I picked a racing game that I knew I was much better at than he was. Of course, within the first few races, I won most of them.
"Gee Matt, you're awfully lousy today." I said jokingly. "Maybe we should up the stakes here, and maybe you can win a bit more."
"What did you have in mind?" Matt was never one to back down from a challenge.
"Why don't we do it like strip poker? Every time you lose a game, you have to take something off." I smiled over at him.
"I dunno Joey..." He sounded really nervous, it was kind of cute.
"Aw come on, I've seen you naked before, and you've seen me too, so what's the big deal? Not like your parents are gonna see."
"Fine. You're on." He said, picking up his controller and getting ready to win, so he thought. Of course, I let him win the first game, just to get his confidence up.
"What should I take off first?" I asked.
"The sweater for now." He said. I complied, removing my sweater to show the wife beater underneath. It was an old white one I'd had for years, very tight.
I won the next one easily. "Take off your pants Matt." I smiled over at him.
"Pervert." He shot back, standing up to undo his belt. His white briefs came into view as he dropped them. I couldn't have planned this better apparently, as he was wearing the exact same pair as I was. I could feel myself getting harder inside my pants.
We settled back in for the next race. It was a close one, but I ended up on top.
"Time to lose that sweater too bro." I said, gloating. I was a little upset, as he did look really good in the sweater. He looked a lot better in the black muscle shirt he had on underneath of it though.
I was a little distracted the next race, watching his cute ass in the briefs, and his nice arms sticking out of the shirt. Without meaning to, I ended up losing that one.
"I think we should even things up a little here." Matt said. "Lose the pants."
"Who's the pervert now?" I asked, dropping my khakis.
"I thought you wore boxers." He said as I laid down next to him on the floor.
"Oh, well I wear briefs sometimes." He didn't even recognize them. Perfect. I was nervous that he might.
"I keep thinking I'll try boxers one of these days." He mused. "My dad keeps buying me briefs though."
"Next time you're over at my place I'll let you try on some of mine." I said.
"Sure thing." He said, and paused. "So what happens when we get down to nothing?" He asked. The question I had been waiting for.
"Whoever loses has to suck the other one off." I smiled at him.
"Gross dude!" He laughed.
"Seriously." I said. "That's the only fair way to do it."
"Serious?" He asked.
"Yeah, so unless you want to be slobbering on my balls, you better win."
"Fine, you're on." He still didn't think I was serious.
I let him get ahead in the next one, think he was going to win. At the last second I overtook him, and with a laugh I said "Lose the shirt buddy."
He blushed a little and took off his shirt. I watched as his pale pink nipples came into view, along with the beginnings of a six pack.
"Ready to suck my dick?" I teased him during the next race. He was getting nervous, and his driving was sloppy, which worked out better for me. He lost that race as well.
He stood up, blushing, and hooked his thumbs into the waistband of his briefs. It looked like he was half hard inside of them.
"You can leave those on for now." I said. "But remember, if you lose the next race, it's blowjob time." He swallowed, and laid back down to race. I wondered if I should just end it now, or let him win a few just to get him more comfortable. He solved that problem for me, being so nervous he practically lost the race right from the start.
"Nice one." I said. He looked almost ready to cry. "Get on your knees bro." Surprisingly, he did. I could tell now that he was more than half hard in his briefs, they looked ready to explode. I stood up.
"Looks like you were looking forward to this." I said, rubbing his package with my foot. He looked up at my crotch.
"Looks like I wasn't the only one." He smiled, looking at my hard cock in the briefs. He leaned in, and started to kiss my dick through them. I let out a low whistle as his kisses became harder and faster, soon his lips were massaging my cock through the briefs.
"Wow." Was all I could say as he started to lick and suck harder. There was no mistaking it now, this boy loved cock. I pulled my wife beater up over my head and tossed it into the pile of our clothes.
"Are these my briefs?" He asked, still kissing and nuzzling at them.
"Yeah, I took them when I went upstairs earlier."
"That's hot." He said, going back to work. He was working himself into a frenzy on my crotch. I looked down and saw how much spit was covering my briefs.
"Damn Matt, slow down, you'll wear a hole through them." I said somewhat jokingly.
"I don't care Joey, I want at your cock."
"Take it out." I said. "It's all yours." With that, he pulled the briefs down to my knees, my six inch cock flopping out in front of his face.
"Wow." He said, echoing my statement earlier. "It's beautiful." He was transfixed on my cock.
"Go on man, you know you want it." I egged him on, finally getting rewarded as his luscious lips opened up and took in my cock. I was in heaven. I'd fooled around with a few guys before but they were nothing compared to this.
I could feel his tongue swirling around my cock head, his hand keeping a firm grip on my shaft. He was using his free hand to rub his own hard on inside of his briefs.
"Are you sure this is your first time?" I asked, barely able to keep standing up. He smiled up and me and nodded. "Shit you're amazing Matt." I breathed out.
"I've wanted to do this for so long." He said, pausing long enough to say that before going back to sucking. I stopped him for a second, stepping out of the briefs and sitting down in his dad's chair. He was in front of me in a matter of seconds after I sat down, his mouth back onto my rod.
His head moved down lower and I felt his tongue on my balls. I let out a gasp as he kissed and lapped at my nuts, the whole time moving down lower.
"Spread your legs." He said. I sank down in the chair and spread my legs, giving his tongue access to my ass. I had to grab the arms of the chair and bite my lip to keep from crying out, as his tongue made contact with my tender hole.
His tongue worked it's way deeper into my ass, the warm, pulsing feeling driving me mad. I soon gave up on trying to control myself, and started to moan and gasp as he tongue-fucked me. I let out cries loud enough I was sure the neighbors heard, but I didn't care, I was so horny.
"Matt, let up for a second." I said, panting. He smiled up at me from between my legs. "Stand up, it's my turn." I said.
He stood in front of me, his organ standing at attention inside of his briefs. It was smaller than mine, probably closer to 5 inches. I knelt down in front of him, and repeated his performance on me, kissing and stroking his briefs.
"I didn't know you were such a fan of briefs." He sighed, running his hand through my hair.
"Only on you." I said softly. He chuckled, and soon started to groan as I sucked harder and harder on his cotton covered crotch.
I didn't wait for his permission though, pulling his briefs down slowly, enjoying the sight of his 5 inch prick coming into view. I pulled back the foreskin that was covering his head, and licked up the beads of precum that were hiding there.
He gasped as I took his dick into my mouth, giving this teenaged stud his first blowjob. I took his entire cock into my mouth, wrapping my tongue around it again and again. Soon I was pumping my fist up and down his shaft, slicked with my spit and his precum.
"Oh my god Joey." He said, bucking his hips in time with my mouth. "We should have been doing this for years!" He exclaimed, holding me by the hair and fucking my face. I was surprised at how into it he was getting, a big change from the shy boy taking off his pants earlier.
He stopped me. "Lay down." He said, kicking off his briefs. He laid down with his face at my crotch, his dick at my face. "Let's 69." He said with a grin, swallowing my dick.
"Sure thing bro." I took his dick back into my mouth, loving the sensation of having a cock in my mouth and a mouth on my cock. We worked together for a while, at the same tempo, before going wild. My lust from earlier was boiling over, I had to taste his cum.
For his part, Matt was an excellent cocksucker. He was deepthroating me, and keeping me close to the edge without sending me over.
"I'm gonna cum soon." He sighed, jacking me off. I thought about saying something, but I redoubled my efforts to suck him off. He was moaning louder and louder now, I knew he was close.
At the last second when his body was tensing up, I moved my hand to his hole and started to play with it. He let out a loud cry, and he shot in my mouth. He was spasming the entire time, as it seemed a never ending supply of jizz spewed forth from his dick. It tasted salty and sweet all at the same time.
He barely gave himself a minute to recover before he was back on my dick, moaning and groaning the whole while. He was so into it, his eyes closed and lips sucking at my rod. I laid back and enjoyed his mouth.
It wasn't long before I was edging closer myself. I grabbed him by the hair and started to control the rhythm. He let me.
"Shit Matt, I'm gonna cum soon." I don't know what I expected, I guess I figured he would pull off and jerk me off to finish. But he dove down onto my dick, his tongue flicking all over my head. My hips shot off the ground and I shot my own load, which Matt managed to swallow all of. I flailed around for a few seconds, letting my orgasm wash over me.
I opened my eyes to see Matt's face above me. In the biggest surprise of the night, he leaned down and kissed me on the mouth. His tongue gently probed at mine. He leaned down on my chest, and we cuddled there on the floor.
"Happy Birthday." I said finally. He laughed at that.
"It was the best present ever."
"No, it was the start of the best present ever." I looked down at him and smiled.
"Guess we won't need the air mattress tonight." He said, standing up and grabbing his briefs.
"Were these the ones I had on, or you?" He said, looking them over.
"Who cares?" I responded, grabbing the other pair. We both put them on at the same time.
"You look... amazing in those." He said, his eyes fixed on my bulge.
"You too bro."
"Why don't we head up to my room? We can try on a few more pairs." There was a mischievous glint in Matt's eye.
"Whatever you'd like to see me in." I made a fake bow to him.
"Let's go." He said with a smile, kissing me before we went up the stairs to his room.