Best Friend, First Time

When I was eighteen I was going out with Jaclyn. We had been together for two years: I knew her family, her friends and her entire life story. Her older brother, Teddy, became my best friend. We just clicked, like we were brothers... which he always joked about because "if we are brothers, your girlfriend is your sister...dude, that's wrong..."

We laughed every time he said that stupid line, but some times it felt true though. Some times when Jaclyn and me were fooling around together I felt gross, not right.

Sorry to say this about her, but she loved to suck my 7' cock. She was almost obsessed. Soon every time we were together she would fondle me into getting an erection, drooling all over herself. At first it was fantastic, then slowly it became gross, boring and it took longer for me to get hard and get off. I wanted to end it, but I couldn't.

She knew something was on my mind and for a month it felt like we were just going through the motions, mimicking what we thought a relationship at seventeen was supposed to look like. Everyone thought we were so happy and in love. I did love her, but I realized it wasn't a sexual kind of love.

Then Teddy came home from college for winter break. I was amazed in the short span of a semester he had formed muscles everywhere... And it was hard not to notice. He took his shirt off any chance he got: when the heater rose above seventy-four, no shirt; something spilled anywhere (sometimes not even on him), no shirt, just out of bed or shower, no shirt.

His body was so hard, lean, and rippled. I wasn't attracted to him, it's not like I couldn't take my eyes off of him, or I jerked off to him... It felt more like envy or deep admire.

We started hanging out a lot more. Jaclyn and I were taking a little bit of a break...well she told me to see other people... and I was so happy Teddy wasn't "too old" or "too cool" to hang with me.

One day we were playing Halo, I was kicking his ass.

Then he started getting really into the game, sweating and breathing a lot harder: the shirt came off and I started losing. He was right next to me, sweating on my shoulder, yelling, rustling, moaning when he died, rubbing me, pushing me when he killed me. Laughing, sighing, jolting. Hot sticky breath all over me, my neck. I slowly started getting hard, sweaty and nervous.

My heart started beating like a giant drum, I could hear it and feel it in my throat. Then he killed me by surprise and got really close to my ear and whispered "Yeah, take that shit!" and "That's right, I just fucked you ass up!"

Then I was completely hard. I crossed my legs, using my hands and controller to mask my tent.

Then he won the whole challenge, and turned to me laughing, pushing me over and tickling/wrestling me, yelling "You suck, you suck," in my ear. His whole body rubbing on me.

I couldn't take it any more, I exploded in my pants. It felt like I came in seven shots, and I knew I moaned loud and shook. I just know I trembled a lot.

Then after my eyes stopped rolling back, I found his face, his shocked, almost terrified, surprised face. He slowly got off of me padding his crotch feeling my warm seaman.

"Did you just get off, dude!" He whispered loudly.

"I'm... so sorry..." I quickly got up trying to cover my soaking pants. "I haven't got off in a while, sorry" I started leave the room, when he grabbed my arm and pulled me back in, closing and locking the door behind me.

"You can't go out there with wet pants," He said in a condescending quiet tone as he searched for some shorts and threw them at me.

"Thanks," I said nervously, trying to avoid eye contact...I slowly started taking off my pants and was about to put the shorts on when he stopped me.

"You can't put those on wet underwear... it will show through!" he whispered again.

"Riiiigggght," I couldn't even look at him, I was so nervous and embarrassed. I just took my underwear off revealing my wet semi-hard cock still dripping with cum. I glanced up for a second and caught him looking at me.

I tried to hurry and put the shorts on, but he stopped me again. He grabbed my arm, and guided me to sit, still bare bottom, on his bed.

"Umm, so you an Jaclyn aren't going out any more right?" he said quietly as he slowly moved forward. His face was right in front of me looking at me, I could tell he was desperately trying not to look down. And I was desperately trying to look away.

"Yeah, that's why I was so trigger happy, we haven't fooled around in over a month"

"ew that's gross" He shuddered. "don't ever say that again." he smiled. Suddenly I felt at ease. I smiled too and I started to pull up the shorts, until he grabbed the elastic of the shorts and would not budge.

"Why...are...?" I started to ask, but he interrupted me.

"So you got off by me just roughing you up?"

"Well, we were rubbing, breathing and sweating on me for half an hour, foo' " I said in a sarcastic tone.

"So I got you hard?" he tilted his head and smiled.

"Well, more like you moving around on top of me" I reminded.

"Still you got off to me..." he scooted a little closer to me, then pulled into my space literally an inch from me lips. My heart started to beat fast again, I felt my cock getting hard... He looked down and saw my massive red shinny hard on. My cock head prodding out of my foreskin. "Dude, your gay..." He laughed as he looked back up at me.

"No, I am not!" I got so flustered I started to pull away again, then he put both his hands on my shoulders and tackled me down on the bed...

"Get off of me" I sorely said as my cock poked at his front while I tried to struggle away.

"Its okay, I am cool with it," He said trying to keep me down. Then, I felt something on my cock.

His cock....

He was hard too, rock hard, I could feel it on my stomach and legs as I struggle up and down.

"Your gay too..." I said in surprise...

He looked down and realized he was throbbing, then he got up off of me.

"I'm not gay..." he said in wonder as he took off his pants revealing a circus tent... He almost looked like a little kid discovering something amazing... He then took off his underwear, unveiling about a 9' monster cock. I couldn't look away. It was huge, dark, cut and throbbing...

I waited for him to put his cock away, but he just stared down at it, occasionally looking at mine. Then to my surprise he started to jerk off.

He held out his hand, "Spit," he demanded.

"What?!"

"Dude, I don't have a foreskin like you, I need some lube..." He said it like "duh," like it was common sense and no big deal.

"This wasn't happening" I said to myself as a took his had with both of mine, lowered my head and hawked a massive loogie into his hand. Then he wrapped that hand around his dick and started sliding up and down moaning "Oh yeah, that feels so good."

I just started at him, my cock throbbing, begging for someone to touch it... my mouth was open a little wide, my breath felt heavy. I couldn't look away.

"Go ahead..." he said sitting back down. "I think its okay, I mean you already got off on me, what's jacking off with me?" He laughed lightly.

I didn't touch myself... I just stood there, watching, in shock...

"This isn't happening."

Then he moved toward me, grabbed my cock and pulled me toward him... to his face. I could feel his clammy breath on my cock.

"Fine... if you won't jerk off..." he the started lick my shaft. I started to pull back, but he wrapped his arm around my hip, his hand on my ass pulling me closer.

"what are you..." I started to say until he slid his tongue under my foreskin, rolling it around on the tip. My mind stopped and all I could think about was how much better he was than Jaclyn. My heart was beating so loud and fast... I felt flushed and hot.

He started sucking. Deep, almost half way in. His tongue crazy and uncontrollable. I could hear him flapping away at his own cock, fast and furious. Both of us panting louder and louder, and slightly moaning.

Then he took his hand off my ass and raised it open toward my face. I immediately spat into it. I didn't want him to stop sucking! He moved that hand out of sight and for a while, I didn't even give it any thought...

Then I felt a small jolt. He slid a well lubed finger up my tight ass...

I let out a grant, as my legs started shaking. I think I wanted to pull away, but his mouth completely swallowed my cock...I couldn't stop.

Slowly in and out his finger felt so warm. He slowed down his jerking, into a small pulse up and down. He slowed down his sucking, then pulled my cock out of his mouth to lick it all over and swallow my balls.

Soon another finger... "Oh my god" I panted as they slid into me. Deeper and a little faster.

He sucked on my balls slightly jerking my shaft with his nose and upper lip.

I was so sweaty and dizzy at that point, I felt like falling over...

Then another finger... three, faster...it was starting to feel really good. I was moaning a little louder now, moving my asshole onto his hand, my cock into his mouth. It felt like I was the one fucking HIS fingers.

My eyes closed, but I swear I could see the back of my skull.

"Can I fuck you?" he whispered.

"No...!" I pulled away from his mouth, "No, way!" I said eyes open...in horror.

He stopped jerking and got up, he took his jerking hand and started jerking me off. His face on top of mine, nose to nose.

"Please," he whispered as he gently kissed nose then my lips.

"No" I whispered back, eyes slowly closing. I was panting a little more like a dog.

"Please..." he begged again kissing me harder and faster...

"No..." I muttered through his mouth...gently pushing him back.

He grabbed me, and pulled our mouths together.

Soon we were making out, hard and fast... his tongue counting my teeth, his cock digging into my hard stomach. My cock digging into his.

Both of his hands were on my ass. It felt like he was trying to make our bodies melt together, forcing me closer to him, pressing and sliding us together. His body was sticky and wet like mine... I felt so hot it felt like I was going to explode again... then he stopped.

"Oh, yeah, huh" I moaned...

He started to pull away... "No more," he smiled...

I wanted to cum so bad. I quickly grabbed him and tried to kiss him, but he pulled back...

"Nope..." He smiled wider, he knew he had complete control of me and my penis...

"Please..." I begged, trying to kiss him...

Then he turned me around, his lips on my neck his hands on my chest sliding, caressing me. I was so horny, "Fine...!" I moaned, "Just get me off before I pass out!" I slightly spread my legs apart. I closed my eyes tight, I knew it was going to hurt...but I wanted to cum.

I was his for the taking...

Then I heard him spit, a quick slicking sound and then I felt his cock on my crack sliding down.

"Please," I begged... "Hurry..."

That was it, the limit to his restraint. He quickly rammed his entire monster cock into me. He hooked my arms into his and plowed deep, his chest on my back, his head over my shoulder and his breath down my chest.

He just left it in there for a minute. I could feel it throbbing in me, like it was close to my heart... beating. I was breathing wildly, we both were.

"Please, fuck me..." I said, surprising myself. "Fuck me" I loved this.

"oh yeah," he panted as he started to thrust in and out of me, picking up the rhythm.

"Yeah, fuck me." I moaned, again. "fuck me" I wanted it.

It was starting to feel so good, just like jerking off.

He started fucking me faster and deeper, moaning and panting louder and louder. I felt pre-cum drip on my toe. I really wanted to touch myself, but I couldn't move my arms. We were locked. My cock felt like it was going to explode.

"Harder" and "harder" I begged... "fucked me harder," and I was closer, and closer to cumming. It was like I was falling and running at the same time, I was so close.

"Oh god," he nuzzled my neck, then kissed it deeply... "I am going to cum!" he shouted.

I was shocked back to reality, I couldn't let him cum in me...! I tried to struggle free, I shouted

"No, don't you cum inside..." too late...

He trusted deep into me forcing my head onto the bed, like he was trying to pry me in half. He moaned in my ear "Yes, god yes, oh, ah, yes, ummm, god...yes"

His body shaking. His voice in ecstasy and agony.

Then he stopped thrusting... "I'm fucking cumming" he moaned.

I felt it inside me. His huge cock pulsing in my tight hole, I counted twenty-two contractions before he stopped. He just shot his massive load into me without moving his body.

We stood there for a couple of minutes. Until I felt his cock slowly move in and out as he subtly fucked me. I felt warm inside, and soon I felt that warmth dripping down onto my legs. Drops lead to a small stream. A lot of cum dripping out of my butt.

I was speechless... he then started sliding his arms down until they grabbed my hips. He then turned us around and sat us down on the bed, his cock still very hard in my ass.

We started getting a good rhythm down, my body was bouncing and tingling, my mind was numb. The wet sounds of ass fucking became even louder with cum as lube.

Then he laid on his back bringing me down with him, still fucking and picking up the pace. I then started jerking off vigorously, I wanted to cum so bad it felt like I was going to die if I didn't.

Then he pounded my ass harder and deeper and stopped.

"Oh god, ah," I panted... I was going crazy, I was cumming....

"Yeah, cum all over us!" he moaned as he jolted his cock deeper into me, thrusting into the air. Harder, stronger...faster!

"GOD! UH!" I shouted loudly, "I'm cumming!" I let out several shots all over my stomach, neck and even my face. My whole body out of control, jerking and pulsing. "Yes, Uh!!!!"

He kept fucking me, even though I just screamed, probably waking up everyone in the house. Harder, harder, harder....and I wanted it...

"Deeper!" I demanded...and he fucked me deeper...

Then he rolled me over on the bed and grabbed my legs flipping me face up. He quickly stuck his cock back in me, my legs on top of his hips and we both were moaning crazily. We were fucking impossibly harder like we were trying to start a fire...

My cock was leaking more cum, as he trusted into me. He was fucking me so hard it looked like my cock was trying to escape my body.

He brought his body on top of mine, hugging me deeply. His face berried into the pillow behind us.

Then I heard muffled moans, and then a giant "Oh yeah, oh my god!!!"

His cock even deeper in my ass, like it was touching my soul... or something...

And he keep thrusting, cumming deep and moaning loud.

"Oh god," he yelled as his body shock uncontrollably. "Oh god, uh, yeah, uh I'm cumming!" It felt like the longest cumshot ever.

I quickly rapped my lips around his to keep him from moaning louder. He screamed into me, my whole throat shook, he just keep thrusting until he emptied every last drop.

Then his body went limp on top of me.

Flushed, wet and red we just laid together for what seemed like forever. His cock started to shrink inside me, I felt it slowly make it's way out soon followed by a river of warm, white, wet mess. My whole butt was soon moist, so much cum, I thought I could float on top of it. My cock shrank too. I felt so drained and relived and perfect.

I passed out with him on top of me, then I woke up with him spooning my back. His arms wrapped tight around me, his lips on the back of my neck.

I fell back to sleep. I remember having a huge smile on my face as I kissed his forearm.

I remember falling in love with that night and every day for the next two months...