My new roommate moves in today. I'm in my third year of college and I've had a different roommate in my dorm every year. The first one was Archie-Archibald Martin Van Cleeve,IV. A total nerd type, we clashed from the beginning. He was in college to learn, I was in college to party.
I had just graduated high school when my mother died. I couldn't stay home anymore and soon headed off for college, leaving my brothers, Rex and Ryan, at home with my dad Hank. My parents loved having all their sons' names start with the letter "R". I was named Reginald after my great grandfather, but I was always called Reggie.
Dean Young was my roommate my second year in college. He and I got along very well. He helped me find the balance between partying and studying. He also convinced me to try to join a frat-Chi Phi. It wasn't usual for a sophomore to rush a frat, but Dean convinced me to go for it.
Soon Dean and I were doing whatever we could to join the frat. We did lots of embarrassing things-eating bugs, licking armpits and made it to the second round of tryouts.
In the second round all the rushes were sworn to secrecy about what we would have to do. We were told that if we told anybody what happened there, we would get the shit kicked out of us and no one would believe us. Dean and I promised to keep the secret, not knowing what the challenge was going to imply.
The frat members got out several dice and handed one to the first several pledges in a single line. We were told that we would all roll and what we had to do would depend on what number we rolled. Those rolling an even number would have one thing to do, those rolling an odd number would have something different to do.
The frat members wouldn't tell us what the challenge would be. We would be taken into separate rooms one at a time, where we would roll the die and be told what we had to do. If we chose not to do it or failed to complete the challenge we wouldn't make it into the frat.
Dean rolled before me, he rolled a one. He was taken into a room with a frat member named Alan. The next several pledges rolled the numbers and were ushered into the remaining rooms. Some were in there for awhile, others not so long. When Dean came out Alan had a huge smile on his face and Dean was beat red. All the pledges were forbidden from speaking to the remaining pledges.
Soon it became my time to roll the die. I rolled a six and was taken into a room with a frat member named Vern. He was a tall, skinny guy. As soon as we walked into the room, Vern pulled down his pants and sat down on a chair.
"Suck my cock, pledge," he ordered.
"What the fuck are you talking about?" I asked.
"You rolled an even number," he said. "You have to suck a frat member's cock to make it in. You don't suck it, you don't get in."
I was floored. I had never had any gay fantasies my entire life. But I was desperate to get into the frat. Moreover, I didn't want Dean to get in without me.
I asked Vern what the pledges who rolled odds have to do. He said they had to jack a guy off. I pictured Dean jacking off Alan and understood why their faces had been the way there were when they came out of the room.
"You gonna suck me or not, pledge?" Vern asked me. I nodded yes, though I definitely didn't want to.
Vern's cock was already hard. It was a long, skinny prick, probably just over seven inches. Not very thick, but I wondered how I was going to swallow it.
I got down to my knees in front of Vern and wrapped my hand around his cock. I was surprised by how warm it was. I started to stroke it a bit, but he grabbed my head and shoved my face down on his peter.
I resisted a bit as he tried to force his cock into my mouth, but his dick soon broke past my lips and he was in my mouth.
"Bite it and I kick your ass," he told me as he pulled my hair a bit.
His cock was warm in my mouth and I started to do what I remembered girls doing to me when I got blow jobs. I began to lick his cock, swirling my tongue around the head of his dick.
Apparently, he liked what I was doing. I heard him moan and looked up to see his head roll back. He grabbed both sides of my head and began to guide me up and down on his cock.
He slid each inch slowly down my throat and I was floored when I was able to take it all. Soon my nose was pressed against his pubic hair. I started to swallow and covered his cock with my saliva. He moaned again and I found myself enjoying what I was doing.
I started to suck and lick his cock, sliding up and down on his hot pole. I realized I was getting hard myself, but I didn't care. I was enjoying sucking his cock.
"Yeah, pledge," he moaned. "Suck my prick. Eat my cock."
I bounced up and down on his cock for awhile. I felt him tense up and realized he was going to cum. I tried to pull off, but he grabbed my hair, jamming his cock down my throat and my nose deeper into his pubes.
"OH, YEAH!!" he moaned and I felt his cum spurt from his dick and slide down my throat. I tried again to get away, but he held me close.
"Drink it," he ordered. So I did. I drank his cum and found I liked the taste of it.
His dick softened and it plopped from my mouth. He stood up, and pulled up his pants. "Good job," he said before he left the room and I followed.
I sat next to Dean and we gave each other knowing glances, we both knew what the other had done. We were there for awhile as the other pledges were taken into the room. Several came out with guilty looks on their faces, others came out and were thrown out- they had either refused or failed.
Soon there were just ten of us left, including Dean and I. We were told that we had all passed the challenge, but there was one more. We would be given instructions later.
Dean and I said nothing as we studied in the dorm room that night. We went to sleep without any conversation.
In the middle of the night, I woke up as Dean shook me.
"Man, I gotta talk to you," he said. I sat up and asked him what was up. He said he was flipping out over what he had done to Alan. He asked me to tell him about what I did. So I relayed the story of me sucking Vern and him dumping his cum in my throat.
Dean then told me his story. He said he walked in with Alan and was told what he was supposed to do. Alan asked him if he was going to do it and Dean said he reluctantly agreed. Alan had then pulled off his pants and laid down on the floor. Dean said Alan had a thick cock, he could barely wrap his fingers around it. He said he was surprised by how warm it was. He said he jacked Alan off for a bit and also had to fondle his balls. Dean said it didn't take Alan long to cum and when he did it shot everywhere. Alan had then ordered to Dean to lick off the cum. Dean said he had to clean off Alan's dick, and lick the splatters of cum from Alan's balls, chest, stomach, arm and nipples.
After his story, Dean sat there silent for a minute. I decided to speak up. "I kind of liked it." Dean stared at me, absolutely floored. Then he spoke, "So did I." Feeling relieved, I said I liked the dick in my mouth and loved the taste of his cum. Dean said he loved Alan's warm cock in his hand and also loved the taste of his cum.
We sat there silent after a bit. Dean broke the silence this time. "I wouldn't mind doing it again. And maybe trying some other stuff, too." I admitted I wanted to do it again, too. "Of course it doesn't mean we're gay or anything," I said. I agreed.
I was already half naked, wearing just a pair of boxers. I pulled off my boxers and was already hard. My dick is six inches long. Dean stripped-he had a five incher. We stood together and rubbed our cocks together. His cock felt so good against mine, I knew I had to suck it.
Without a word I slid to my knees, took Dean's cock in my hand and then slid it into my mouth. I swallowed it all and buried my face in his pubic hair. I reached around and grabbed his hips and tried to push his cock even deeper.
"Oh, fuck, man," he said. "That feels so fucking good, Reggie."
I started sucking Dean and he moaned in response to my hot tongue all over his cock. Soon his hands were on the side of my head and he was fucking my mouth.
"Oh, yeah, oh yeah," he repeated again and again.
I took his cock out of my mouth for a moment and said "Give me your cum, Dean. Shoot your fucking load down my throat."
Dean smiled. He grabbed the back of my head, slammed his cock as deep as he could down my throat and froze. As he made short jerking movements and made little grunts, I felt his cock spurt his jizz. I willingly swallowed it all and sucked him until he was soft.
Dean laid down on the floor and I laid down next to him.
"Damn, that was a good blow job," he said in between breaths.
I was still rock hard and my cock was standing straight up in the air. Dean was still short of breath as he reached over and started playing with my cock. His hands felt so good around my dick.
He stroked me for a bit as he worked to get his breath back. Then he was between my knees and was swallowing my cock. He was a good a learner and was an excellent cocksucker. He fondled my nuts as he sucked me and it didn't take me long to reach an orgasm point.
I let him know I was gonna cum and he didn't move. I shot my cum into his mouth and he swallowed. Now it was my turn to be short of breath.
"Wow," was all I could see. Dean agreed. I closed my eyes and fell asleep on the floor. I woke up a few hours later and Dean was still asleep next to me. He was pressed up against me and I realized I liked him being close.
Dean and I started sucking each other off all the time. We were horny 20 year olds and could cum and cum again. And we did. On a side note, we didn't make it into the frat, we failed the final challenge.
After a few months of sucking each other's cock, I brought up the idea of anal sex. I told Dean that I really wanted to fuck a guy's ass, in fact I wanted to fuck his ass.
Dean was a bit reluctant to let me do it, but I swore to him that I wouldn't hurt him. I wanted so bad to fuck his ass I could taste it. I had tasted his ass a few times when we played. Finally, he agreed after I promised that I would stop if he asked me too.
We got ready for the night with a thorough scrubbing and cleaning. We started off as we normally did, playing with each other through our clothes and then slowly undressing. My cock was rock hard at the idea of fucking his ass.
Dean laid on his back on the floor and I crawled between his legs. I sucked his cock for a bit and also licked his ass, getting his hole wet with my saliva. I then poked one finger one and then another. I had done this before and he loved to jack off as I finger fucked him.
I finger fucked him a little longer and harder then I normally did. Then I pulled them out and slathered his ass with lube. I lubed up my own cock and prepared to fuck him. I lifted his legs and put my cock on the outside of his ass. With one hand on the floor beside him and one hand on my cock I began to push in. He held his legs in the air and I saw his face grimace as I tried to get into him.
I started to think that there was no way I was getting in when all of a sudden My head slipped past his ass ring. His mouth shut open.
"Oh, fuck," he said. "It hurts. I don't think I can do this."
His ass felt wonderful around my cock and I didn't want to stop. I knew he was about to tell me to pull out so I leaned forward and kissed him. We had never kissed before, it had been taboo. He was shocked, but he didn't resist for long. Soon he was kissing me back and our tongues were dancing.
"Your ass feels so wonderful, Dean," I told him. "It feels so good to have my cock in your ass."
His fears went away. I began to push slowly into his ass. His tight ass felt so good. Better than anything I had ever felt. I fucked him slowly and lovingly. I whispered in his ear how much I loved his ass and surprised us both when I told him I loved him. He replied that he loved me, too.
Our fucking got quicker and soon I was pounding his ass and he was begging me to do it harder. I felt myself getting close to cumming and couldn't stop it. I shot a load deep in his bowels and collapsed on top of him. My dick softened and I slid from his ass.
I laid on top of him for some time. We were both breathing heavy. I slid off of him and laid next to him. I wasn't sure what to say.
Finally, I rolled over and whispered in his ear. "That was awesome, man. Really fucking awesome."
I was thrilled when he smiled and said -"Yeah, it was."
Dean told me that it hurt at first and then it felt good. He said he loved having my dick in him, it was different than anything he had ever felt before. Then he asked me a question.
"Did you mean what you said?"
I knew what he meant. He wanted to know if I meant it when I said I loved him. I hesitated to answer, but told the truth.
"Yeah," I said. "I meant it."
Dean hadn't cum yet and he was still rock hard. He sat up, swung his legs around and straddled my stomach. His hot cock sat on my stomach. He leaned down and we kissed warmly and lovingly. I wrapped my arms around his neck and pulled him close to me. We kissed as he rubbed his cock on my stomach.
He then sat up and started jacking off. With one hand he stroked his cock, with the other hand he pinched my left nipple. I ran my hands up and down his sides and told him how much I loved being with him.
I could tell he was getting close to cumming and I told him to shoot his load on my stomach. He let loose with a gigantic spurt that shot all the way to my cheek. He leaned down and we kissed again, the sperm on my stomach rubbing on us both.
We cleaned up and got ready for bed. Dean asked me if I would sleep with him that night and I did. We soon began sleeping in the same bed often. I fucked his ass and made love to him every day and often more than that.
For Dean us being together answered a lot of his questions in his life. For me, it brought about more answers. He was ready to settle down with me and thought we could be together forever. Although I loved Dean, a lot, I wasn't ready to settle down. I wanted to try more things, specifically I wanted to fuck more guys.
Dean hated the idea of letting me play with other guys, but gave me permission. For me it was the best of both worlds, a loving relationship at home as well as having hot and horny encounters. It didn't take long for both of us to realize it wasn't going to work. He came back to the dorm room one time and found me pounding another guy's ass. He broke down in tears.
Dean told me he couldn't share me. I said I couldn't have a monogamous relationship. We decided that when the school year ended we would go our separate ways. I expected to see him on campus, but learned that he had joined the Marines. I didn't think I would ever see him again.
And so today I get my third roommate in three years. I wonder what he'll be like....
Feedback and comments are welcome.
Dean offers to suck Reggie off first. They both love it. Reggie sucks Dean off. Reggie wants to fuck Dean's ass. Takes some convincing. Both love it.