My Roommate Jake

After a few minutes of me sucking is dick and him rimming my hole, Jake rolled off of me. Slightly disappointed as his dick came out of my mouth but full of anticipation on the prospect of having it in my ass. Jake pulled a bottle of lube and a condom from his nightstand. He prepared himself and then put a bit of lube on my hole.

"This may start a bit painful, but as your ass relaxes it will become highly enjoyable. I will make sure to take it slow.... At first." And with that he crawled on top of me, looking me in the eye, he lined up his cock at my asshole.

A little pressure at first, and then he backed off.

A little pressure again, and then he backed off.

A bit more pressure, I felt my asshole began to relax and a part of him start to slide in. He then backed off.

A bit firmer this time and I could feel my asshole stretch to fit just the tip of his cock. I would be lying if I said it didn't kind of hurt, but with each rendition of him pressing and relieving, by asshole became more accepting to the idea of his cock going inside.

"Oh an inch and a half that time." Laughed Jake.

He then looked me in the eyes, brought his lips down to mine and he firmly pressed his cock into my ass. My mouth opened up wide as I felt his massive cock begin to fill me. 1 inch, 2 inches, 3... 4.... 5.... 6.... 7. 8. 9. And with that final barrier passed, Jake began to fuck me. Slowly at first but with every thrust it became more determined, more focused, quicker and harder. The initial pain was gone at this point. All I felt was pleasure as he railed my ass. I felt as if I had been waiting all of my life to be fucked, and now that a hot big black cock was in my ass, I never wanted it to leave.

"You like that bitch?" looking down at me. "Are you more than my cocksucking slut? Do you want to be my personal fuck toy?"

As he continued to rail me, my moans became louder, more feminine and more submissive in their tone.. "Oh.... Fuck me like that...... Oh (higher pitched) ...... Oh... My god, your cock is so big..... I love your cock....... Fuck your little cumslut... Fuck your bitch..." If I hadn't been enjoying myself so much, I may have been shocked at what I was saying. "I will be your personal faggot....... Oh, fill me up with your massive cock...... Fuck, it feels so good."

Jake kept fucking me and he reached down and grabbed my cock, still with a bit of lube on his hand, began to rub my cock in unison with his fucking. After 5 minutes of this, I kept getting closer and closer to cumming.

"Jake... I am ...... I am getting close."

"As am I."

Jake continued to fuck me but increasing the velocity of how he was jerking me.

Closer.

Closer.

I felt my body begin to tense as I reached orgasm. And then my load shot. I had gotten distance before, but nothing like this. I didn't know if Jake had planned this and if he was aiming, but the string of cum hit me square in the face. Three pumps did. Though the thought of a self-facial had never crossed my mind, now that it had happened I giggled with delight. This was the best orgasm I had ever had to date.

Jake released my cock and pulled out of me. I was half expecting him to finish inside me and I was almost sad when his cock left my ass.

"I think I am going to have to add to that." Referencing the cum on my face. I leapt up as he took the condom off, and started to suck his, at this point, throbbing cock.

"I am not going to last long...." Moaned Jake ask I worked my magic with my mouth.

I began to feel the throbbing quicken and heard a moan escape from Jake's lips. His first shot landed in my mouth. A slightly salty, yet in no way un-pleasurable taste entered my mouth. I would have been happy taking it all, but Jake pulled his cock out of my mouth and shot at my face for the remaining load. My mouth open wide, I felt the cum go all over my face, some in my mouth, on my cheeks, on my lips. I felt and I am sure I looked like the slut I always knew I was.

As Jake let go of his cock, he came down on me, locking his lips against mine. After sharing the taste of his cum, I felt his tongue work around my face, helping to clean up the mess that he had contributed to making. One additional kiss and, we once again, shared in the fruits of our labor.

I laid back with my head racing. We laid their and talked. Unsurprisingly, I had a few questions of where this came from. He went into details about his conversations with Jessica and her catching me trying to skinny dip with another guy. How he was bisexual (kind of obvious now) and how he would occasionally hook up with guys if he was in the mood on his business trips. He had planned on telling me about his bisexuality but hadn't decided how to tell me.

As we laid there and talked, I was still basking in the glory of my first time with a guy.

Jake finally looked at me and stated, "Well I did tell you that you would get laid more often if you expanded your horizons." I had a hard time disagreeing with that.

"Now that my horizons have been expanded, I think I will be getting laid quite a bit more often."

With a smile Jake began to lean in, "That you will. I intend to exploit the cocksucker in you as much as possible." He kissed me and we began round two for the night.