Story by youknowwho on 13 Jul 2011
Readers: 7184 Score: 4.2 (40 votes)
I never would have thought I would have sex with another guy, let alone enjoy it. But that all changed on that one sleepover with Derek. It was a few days after my 17th birthday and I decided to have Derek over to play some video games. We went up to my room, sat on the couch and turned on the TV. We played for hours, and soon it got pretty late, so he asked if he could stay over. It was cool with his parents, so i agreed. Little did i know, that this would be a sleepover i'd never forget.
We played for another hour until Derek supposedly got tired. He ended up 'falling asleep' on the couch. I wasn't tired at all, but i didn't want to wake him up. So i turned the game off and pulled out my phone. I ended up on a porn site, and got pretty hard watching the two chicks make out. I started to unzip my pants when I looked up and saw Derek looking right at me, and my bulge. I quickly zipped my pants and said 'Oh my god, sorry dude. I was just watching some porn.' he smiled and said 'Seems like you were enjoying it, huh?' and motioned to my crotch. I laughed nervously and we both sat there awkwardly. Then, Derek said something that shocked me:
'Want me to take care of that for you?'
I stared at him, thinking it was a joke I laughed and said 'No way man, i'm no homo, and neither are you!'
He looked at me, with a smile on his face and said 'No, but I have experimented.' i stared at him, shocked, but the thought of him sucking someone else's cock didn't make me go soft, in fact, my boner was still throbbing in my pants, harder than before.
He said 'it feels better to have your cock sucked by a guy, because guys know what feels best.' I thought about it, and it made sense.. but there was no way I was gonna let him suck my cock, i mean, thats wrong!... isnt it?
I looked at him, and hesitated before saying 'But what about.. you know.. the other thing gay guys do?' he looked at me with a smile 'you mean anal sex? it feels crazy good to stick it in someone's ass. its way tighter than pussy.' I was getting a little excited, but i tried to hide it when I asked 'But what about.. you know, having it inside you?'
He laughed and said 'It hurts at first, but it ends up feeling like... well.. you can't explain how good it feels.' i considered it, and looked down at my now rock solid boner, that felt like it was gonna burst out my pants. I looked back up at Derek, and was about to decline his offer and just go jerk off in the bathroom, but he was already walking towards me.
He got me up, shoved me down on the bed, and began to unzip my pants. I began to protest, but when my 8 incher popped out of my pants, stiff as a board, he got to work. He began to suck on the tip of my penis. I moaned with pleasure as he began to work his way down the base of the shaft, massaging my balls as well. i moaned again, as he started to suck harder and faster on my stiff cock. I lost all control and it wasn't long before I bust a huge, creamy load in Derek's mouth. I panted and looked down at Derek, and I could tell by the huge boner in his pants that he loved that.
He licked the cum around his mouth. I shuddered, this was so wrong.. but it felt so good! He simply said 'My turn.' I started to go on 'no.. no I cant do that!' he just gave me a seductive smile and said 'you owe me, dude.' He pulled down his pants and out flopped his massive cock. It was at least 10 inches.
I felt myself getting hard and was shocked. Me? Getting hard over a dude? But i didn't have anytime to say a thing, because before i knew it, he shoved my shoulders down so i was kneeling, grabbed the back of my head and made me suck his huge cock. he pushed and pushed my head further and further down his shaft. I pulled away and said 'no, dude, let me do it.' he smiled and leaned against the wall as i stared down his great big piece of meat. i started to lick the tip of it, and he instantly groaned with pleasure. i started sucking down the shaft, and he started moaning even more 'oh yes.. yes.. YES.. keep going ben... oohh keep going... ughh yesss.' i started to go faster, and faster. i began massaging his ballsack too. I found myself enjoying this. i started to rub my own dick, too. soon he was there, he screamed with and i his cum filled up my mouth. i was surprised to find out how good it tasted.
He looked at me and my boner and asked 'Well, now that you're hard, do you wanna see what else guys can do?' I nodded, desperate to cum like I had before. He opened my dresser drawer and started looking for lube. As he was bent over, I noticed his ass, and how nice it looked. Was I really going full on gay? No.. i'm experimenting! Thats all! He found the lube and turned around. He handed me the lube and then
laid on the bed. He said 'I want to see your face when you fuck me.' he turned around, pulled his legs up and motioned towards his asshole. I looked at it, and nervously stuck the tip in his hole. his face lit up and he pulled his head back and screamed 'More.. MORE!' i started to push farther in, and he was right, it was tighter than pussy, and it felt much better. I started pulling in and out faster and he clenched the bedspread and wailed 'oh GOD it feels so GOOD! Jesus christ Benny dont stop.. oh yeah dont stop! it feels too good don't slow down!' i was so excited i kept thrusting my cock in his ass and we both started screaming.
Finally it was almost time for me to cum. I think Derek could tell because he said 'oh yes ben, cum on my face! i want to taste your sweet cum!' I reluctantly pulled my dick out of his ass and started jerking off over his face. I jizzed all over his face, and it was the biggest orgasm i've ever had.
I laid down on the bed, panting, cock throbbing. I could've fallen asleep right there, when i heard Derek opening the cap of my lube. I turned around and saw him rubbing lube all over his cock. 'W..what are you doing, derek?' i said, although I had a pretty good idea what he was intending to do. He simply said 'Your turn.'
I was so excited, i turned around and held my legs up like Derek did before. he smiled and sat down on the bed. he put some lube on his finger and stuck it up my ass. It hurt so bad and I screamed in pain, but Derek ignored it and proceded to pull his finger in and out of my ass. It started to hurt less and i started to get used to his finger protruding my asshole. i laid back and protested when he pulled his finger out, i wanted more! he said, 'just wait to see how this feels.'
He then stuck the tip of his cock in my ass. I winced but then remembered how good it felt with the finger, and tried to relax. He got to about 6 inches in before I tensed up again. He asked me ' Want me to stop?' but I insisted he keep going. I relaxed and he stuck the rest of his ten inch cock in my ass. He let it sit before pulling it out a little, only to shove it back in. I groaned, this felt so good! He started to go a little faster, and I started to scream out 'Oh.. god no, don't stop! This feels amazing! ive never felt anything like this- ahh!! Yes!! Shove it in my ass! Deeper!! harder! HARDER!!' My cock started to rise and I began to rub it furiously, feeling intense sensations coming from both my ass and my cock. Derek was screaming too 'Yeah baby your ass is so tight, I love it' we were both about to cum when derek screamed 'Oh YES BEN!! I LOVE YOU!! TELL ME YOU LOVE MY COCK!!' i hesitated. Was I gonna be gay for Derek? My girlfriend never pleasured me like this, and i had to admit- i was falling for Derek. i yelled 'YES... YES DEREK I LOVE YOU AND YOUR COCK!! CUM INSIDE MY ASS LIKE A GOOD BOY' he pushed harder and faster inside of me before exploding a huge load in my ass. I cried out as my cock busted a huge one all over Derek's face.
He looked at me, breathing heavily and said: 'Dude... do you really love me?' i looked at him and pulled his head over to me and kissed him. We made out passionatley until our cocks got hard and we went at it again. That was the night I became gay, and the first time i had gay sex. But it certainly wasn't the last. ;)
*Note: i hoped you enjoyed the story! I got really hard and it was hard to concentrate on the story sometimes so please excuse the grammar and punctuation errors :)