My First Time

It started out as one of those nights where you're really bored and have no clue what you want to do. I was hanging out with my best friend Ben at his apartment in Boston. Ben and I have been best friends since we were little kids and had hung out for many a night since. After a long period of "what do you want to do," "I don't know what do you wanna do," we finally decided to rent a porno and get a little shitty.

We walked down town to the adult bookstore. Ben and I browsed the racks of blowjob tapes and "barely legal teens" that looked like they were almost thirty. I looked at my watch and realized that we had been in there for almost an hour. In a hurry to get to the liquor store before it closed we grabbed a tape at random. I paid and we left to pick up some beer.

After getting the beer we went back to Ben's. He put the beer into the fridge while I popped the tape into the VCR. He came into the living room and handed me a beer. We watched the first segment. Just a guy fucking a girl, nothing too spectacular but it got me a little horny. The second segment started as I started my second beer. Ben was on his third.

At the fourth segment things started to get a little weird. There were two guys fucking this girl. Things were going fine until they cut to this one shot. One of the guys was banging the girl on the floor. The other guy came in and stood over the girl putting his crotch in the other guys face. The guy fucking the girl then did some thing I wasn't exactly prepared for. He sucked the guy's dick. The even weirder part was neither Ben or I could look away. Pretty soon the girl had left and it was just the two guys going at it. Finally Ben got up and turned it off.

The two of us just sat there in silence for what seemed like half an hour. Ben was the first to say some thing.

"I can't stop thinking about that," he said, "I don't really think I am gay but I feel like its some thing I want to try."

Being as drunk as I was or maybe I really felt the same way, I don't know, I said, "Ok, why not"

With those words he walked over to where I was sitting. He sat down next to me and began to rub my very hard cock. It felt really weird to have a man touching my dick but it felt good. He stood up and pulled me off the couch. He got down on his knees and undid the fly on my pants. I was eager for him to release my raging cock from the somewhat confining pants. He pulled them off quickly as I pulled off my shirt. He rubbed my balls some more before pulling off my boxers and exposing my eight incher. He immediately began to jerk me off and rub my balls. He brought his head closer to me and started to lick my nut sack with vigor. I couldn't believe how much pleasure I was getting from having a guy. He began to work his way up my shaft, licking and kissing his way up to the head. He swirled it around his tongue for a minute before he took it all in. I began to seriously moan as I was in ecstasy. As he continued his up and down motion, he looked up at me and I could see he was enjoying it too. It didn't take too much more of this before I felt like I was ready to shoot my load.

"I'm cumming," I managed to get out before shooting my load down his throat. I could hardly believe that he would swallow it all like he did.

"Did you enjoy that," he asked

"That was the most pleasure I have ever had sexually," I replied. "I'd like to give you the same pleasure you just gave me."

He stood up and took off his clothes as I knelt down in front of him. He had an eight incher like mine only a little thinner. I wasted no time going to work on his nut sack. I could tell from his moans that he was enjoying it. I worked my up to his head and quickly engulfed it. He began to move his hips towards me as I sucked him in. The taste of his dick was strong and salty and wanted more. As he fucked my face other things started going through my mind. I was about to say something when he blurted out, "I gonna cu…"

He shot his load before he could finish. I tried to swallow as much as I could but some still went on my face. I wiped it off on his shirt before sitting down next to him.

"I want to fuck you," I said.

"I am not sure," he said apprehensively. "It might be kinda painful."

"I have done it to Katelyn (an ex girlfriend) before. She said it only hurt a little bit in the beginning."

"There should be some ky in the bathroom behind the mirror."

I went and got it. I came back and proceeded to squirt some around his butt hole. I inserted a finger and then two and finally three. He winced a little at first but let out a little moan as he relaxed. When I was satisfied that he was lubed enough I rubbed some more KY on my ever hardening dick. We positioned ourselves into a doggy style position. I placed my rock hard dick at the entrance to his virgin hole and gave a bit of pressure. Seeing him wince a little I told him to relax and that the pleasure would come soon enough. It wasn't long before I as all the way in and I began my strokes. I started out long and slow and was enjoying the pleasure his tight virgin ass was giving me. He started pushing back against me and moaning with ecstasy.

"Fuck me harder," he moaned.

I proceeded to pick up the pace and I fucked him a little harder. He kept saying "harder, harder," I so fucked him harder and harder.

"Where do you want it?" I asked.

"Let it go in my ass," he replied.

It took about thirty seconds before I shot my load up his ass. I had never shot more cum in a load in my life.

It took a few minutes for my dick to soften and I could pull out but before I did I knew what I wanted to happen next.

"Fuck me," I told him.

"With pleasure," Ben replied.

He lay me down on my back and spread some lube on my ass hole. I winced when he stuck a finger up my ass. As I began to relax he put in two and then three. After lubing his dick he threw my legs over shoulders and felt his cock pressing at my hole. As he pushed if felt him sliding into me. The pain was incredible. It felt as though I was being ripped apart. I was wishing it would be over when I felt him pull out a little bit. I released he had gone all the way in and the pain began to subside as the pleasure took over. I moaned as he moved in and out like a piston. I began to buck in sync with his movements and wanted more. I couldn't believe how much I loved this. He pulled out shortly and told me he wanted me to suck him off the rest of the way. I happily obliged and he quickly came in mouth as I swallowed every last drop.

We collapsed on the floor and stayed there till morning. When I woke up the next morning I knew that what had happened the previous night was not the first time we would hook up and that there would be many sexual adventures in the future and I couldn't wait till the next time.