Str8 Guy Loses Bet to Gay Roommate

Next he placed his mouth right on my chest and began a slithering tongue action that traveled down my sternum. His journey continued lower and lower. When he reached my belly button, he plunged his tongue right in. He continued his path south, down my treasure trail, into my pubic region and finally reached his target destination. I had already rebounded to another partial erection.

I had always wondered about my size and maybe had even been a little self-conscious. I knew I wasn't tiny down there, but the few times I saw other guys in change rooms or at the gym, I felt like I was a bit smaller. I even googled it once. After measuring myself, I determined I was exactly average. Obviously Max had more experience with penises than I. Since I was lying there naked anyway and we were never going to speak of this night again, I took the opportunity to get Max's assessment. I told him of my concern and asked what he thought.

He said, "You have nothing to worry about. They come in all sizes and shapes. Girls don't care or even usually notice. You are as big as most guys I've seen. I think you and I are about the same size."

He was being generous. I knew he was bigger than me. One night a few weeks ago he went for a late night shower. When he got back to the room, he thought I was asleep. He dropped his robe and for a moment I saw him naked through squinted eyes. In his flaccid state, he had me by a good inch or so.

Max parted his lips and slipped that warm, wet mouth over my still growing cock. I continued to grow in his mouth as work me expertly. He easily swallowed my entire length, wrapping his lips around the base at my pubis. I had never been deep throated so completely before. Next he teased me some by slipping on and off of me a few times. Then his tongue danced and slithered along the underside of my shaft and I'd never felt such a sensation before in my life. He changed back to the full deep throat position, held in place and began to suck in earnest.

I couldn't believe the pleasure I was experiencing. Sheila had given me my fair share of blow jobs over our two years together, but it was never like this. Of course I never felt Max's teeth, but also, his technique, the variety of maneuvers... I was amazed. I was also about to cum again. As Max continued his relentless attack, my dick pulsed, my toes curled and I convulsed in the most intense orgasm of my life.

There was still three minutes left on the timer, but Max let that go. I spent those minutes lying there panting and flushed. Eventually I gathered myself and got redressed. Things could have been awkward at this point but Max made everything easier. He was acting like the normal Max. He asked me, "Hey, are you hungry? I am. You wanna get a pizza?"

It was probably about 10:00pm. I actually was starving. We ordered a mediocre pizza from the nearby Dominos and stayed in our room. We ate and talked. Max and I were already friends. Being roommates for the past 3 months, we probably spent more of that time with each other than with anyone else. That night though, for the first time, we really talked. We talked to each other about our childhoods, our families, friends back home, intimate details of past relationships, even hopes and fears for the future. It was 3:00am before we called it a night and went to sleep.

The next morning, despite only 4 hours of rest, I woke up at 7:00 and couldn't fall back to sleep. I got up and looked down at the sleeping Max. I felt an odd affection for him. He was in his standard sleep attire; boxer briefs and an old undershirt. It was warm in the room and his blanket was cast aside. His undershirt had ridden up a little, revealing a strip of lean lower abdomen. I was tempted to swipe a tickling finger across, like he had done to me the night before, but I decided not to wake him. I discreetly pushed his shirt up a little higher, revealing his round innie. Just like mine.

Over the next few days, I couldn't stop thinking about the night of our bet. To some degree I thought about the physical experience. How natural and comfortable I felt in Max's hands (and mouth). But more than that, I thought about after. How we stayed up all night talking and bonding. I found myself wanting to be with Max more and more. How? Physically? I didn't know.

As I looked around campus and our dormitory in particular, I didn't find myself attracted to other guys. I had always been a confirmed heterosexual. But I felt an undeniable pull toward Max. I felt an emotional connection. I wanted to explore it.

To Max's credit, he kept his word and honored the ground rules of our bet. It seemed to me that to him, that night never happened. He never mentioned it, not even when we were alone. No comments, no bragging, no veiled references. Not even a knowing wink or look as part of an inside joke. Me, on the other hand? I thought about it constantly.

I thought that Max and I had bonded enough that night that I could raise the subject with him. We could have a conversation about what I was feeling for him and what it meant. I just needed to find the right time. All during the week, we were both too busy with labs, assignments, other guys from our floor popping in, etc. Maybe over the weekend things would be more chill.

Saturday finally arrived. I had spent the morning in the library and in the afternoon, I didn't know where Max was. Finally around 6:00, Max walked in. I was surprised to see he was wearing my new black jeans and my favorite high top Osiris sneakers. Well, he did win the bet. I guess we really were the same size. It gave me an unexpected thrill to know that his feet were in my shoes and my clothes were wrapped around his body. As he walked into the room, I realized that he wasn't alone. Max saw me and smiled. He said, "I want you to meet Franco."

It turned out that Max and Franco had begun seeing each other. Max seemed really happy, so I was happy for him, but I couldn't help but feel a sense of sorrow and loss. I didn't understand why I was feeling this way. How could I talk to him now? Max was my friend. I was happy for him. And I was straight, right? Why couldn't I stop thinking about being with him again? This time, me touching him the way he touched me. I wanted Max and now I couldn't have him.