Str8 Guy Loses Bet to Gay Roommate

For my junior year of college I had to move to the dorm for upper classmen. This meant that I had a new roommate. His name was Max and I met him the day I moved in. He had arrived before me and had already picked a side of the room. He was mostly done unpacking and settling in as I barged in with all of my things. We chatted and got to know each other a little while I unpacked.

Max was a nice guy. We seemed to have a lot in common. We both liked sports as fans but neither of us were an athlete ourselves. We both were Science majored and would be spending a lot of time in labs. We had overlapping tastes in music and movies. With our shared interests, we talked easily for hours. No weird silences. We became good friends right away. We were comfortable with each other.

There was one difference between us though. Max was gay and I was straight. Since we were roommates, and quickly becoming friends, Max had wanted to tell me this right away. He didn't want to have an awkward conversation later down the line. He just wanted to be open and up front from the beginning. I thanked him for telling me. I joked that this was great news! We knew we would never be in competition with each other romantically. Max laughed and we resumed a more casual conversation.

I had just spent a joyless summer working full time at my seasonal landscaping job. Right at the beginning of the summer, my girlfriend of the past two years broke up with me. We had started dating towards the end of senior year in high school. We each went away to different colleges, but kept the relationship going, mostly through texts and phone calls. During school breaks we would spend as much time together as possible.

I hadn't seen her since spring break. That first day of the summer, we met up, I thought for a date, and she gave me the news. She had met someone else. It was too hard for her to maintain our relationship while going to separate schools. She said that being her first love, I would always be special to her. She hadn't wanted to do this over the phone so she waited until now to tell me in person.

I was heartbroken. I really thought I was in love with her. I buried myself in my job, taking extra shifts and working overtime. I hardly spent any time with my hometown friends and I certainly didn't try to meet any other girls. I spent the whole summer mourning the loss of the relationship. By the time I moved back to college, I was getting over the loss and was ready to date again.

Having had a girlfriend during my first two years, I hadn't dated or even flirted with anyone here at school. I was starting fresh. I found it wasn't as easy as I hoped to meet someone and make a connection. Over the course of a couple months I had managed just two dates. Neither was successful and neither resulted in a second date.

Max hadn't been seeing anyone either, though I didn't think he was trying as hard as I was. He seemed more laid back about his social life, willing take things as they came. I, on the other hand, was on a mission get back in the game and I was getting frustrated by the lack of results.

One Saturday night in November, I was on just my third date of the semester. It had been so bad that we both decided to quit the date before the evening was over. I came back to our room at around 8:00 and Max was there playing a video game we both liked. I pulled my desk chair over next to his and watched.

Max completed the level he was working on and noted, "You're back early."

I filled him in on the awful evening. "Since Sheila, I am just not connecting with anyone. I feel like I'm over her. I don't know. Maybe my expectations are too high. I'm getting frustrated with the whole situation."

Max asked, "Frustrated? Like sexually frustrated?"

I answered, "Sure, that's part of it." I hadn't been with Sheila since last Spring Break. I was in an 8 month draught.

Max said, "If you want some private time to rub one out and relieve some tension, I could leave the room for a while."

I said, "No, but thanks for the offer. After 8 months of just my own hand, I'm bored with masterbation. It's always better when it's the touch of another person."

"Hey, if you want, I could lend you a hand," Max winked at me.

We both laughed. I said, "I know you're kidding, but you wouldn't be able to help me even if I said yes. I'm not gay. I couldn't get off from another guy. I probably wouldn't even get hard, not to mention...you know."

Max replied, "I was kidding. But, you're wrong. If I tried, I would get you. I would get you and it would be better than any time you with a woman."

"What? You're crazy." We held our gaze. "Look, I am sure you have mad skills, but I would have to be attracted to guys...to you, but I'm not. I love you like a brother, but I'm just not."

Max, a debate team member in high school, argued his point. "I'm not trying to get you to do something you don't want to do. I just want you to know that the fact of the matter is guys can satisfy guys better that girls can. It's only logical. Guys have the equipment. They know what feels good. They know what they're doing. Not only are girls unfamiliar with the equipment, they are usually reluctant performers. They don't want to be there. If they were honest, most of them are little grossed out by the penis."

I thought about this. I remembered back to some of my experiences with Sheila. She was totally into traditional intercourse but anything different, like hand jobs or oral, she was timid and brief. Was Max right? Even if he was, it was irrelevant. I am not gay.

I said, "You're saying, like what? Girls don't know to not use teeth?"

"Sure, that's one example." Max continued, "They lack expertise and technique. Consider this. When you perform orally on a girl, have you felt like an expert down there? Do you know where everything is and exactly what to do to maximize her pleasure?" He paused.

I assumed the question to rhetorical. The truth was I did blunder and fumble around down there. I didn't reply, but Max saw the answer in my expression.

He went on, "You can't say I'm wrong if you've never tried it. Another guy could give you the orgasm of your life."

"I just don't see it. Technique is not enough. For the best orgasm of my life, I would need to be in to it, turned on. Guys don't arouse me. That is a big part of it."

Max said, "You are so sure of yourself. You want to make a bet?"

I got a little nervous. "What do mean?"

"I mean prove it," Max said. "The only way to know that another guy can't get you to cum is to prove it by giving him a chance, and you successfully hold off."

I swallowed hard. "I, uh, don't...I, uh"--

"Look, you said I couldn't even get you hard, not to mention bring you to climax. What's the worst that could happen? Win or lose, when it's over, just think of it as having spent the time getting a good massage."

"I'm only 20 years old. I've never had a real massage." I was deliberately not responding to the challenge.

Max smiled, "I'll take your 'no' as a victory. You won't play along so you must not really believe what you said. You are afraid you'll lose. Like I said before, I do not want to force you into doing something you don't want to do, but now we both know you don't think you'd win the bet."

Being a competitive person, I wasn't quite ready to walk away. "What would we bet for?" We were both broke college students, so money was out.

Max said, "Oh, I don't know. You and I are about the same height and build, right? How about the winner gets to borrow something of the loser's at any time? It could be an article of clothing, or video game, whatever."

I am just shy of 6 feet tall, and 150 pounds. Max does look to be about the same. I said, "Okay. If we were to do this, there would have to be some ground rules."

Max said, "Okay. Go ahead."

Me: "No toys or objects of any kind. All you get to use is you."

A surprised laugh almost exploded out of Max. "Wow, that's where you went first? I don't even have anything—Okay, no problem. No toys. My turn. I get to have access to your whole body. I will have the chance to set the mood with a full experience that begins with some foreplay."

Me: "But nothing above the neck. Kissing has nothing to do this."

Max: "Agreed."

Me: "And nothing goes into either of our assholes. No anal. Just mouth and hands."

Max looked shocked but I wanted to be sure there would be no loop holes or surprises. He again said, "Agreed."

Me: "Also, I hope you aren't expecting me to return the favor. I mean, I'm not going to," a pause, "reciprocate by trying to get you"—

Max cut me off: "No, no, no. That's not what this is about."

Me: "Oh, and there has to be a time limit. This can't go on all night. After a certain amount of time, I win. I was thinking like 30 minutes."

Max: "I was thinking more like an hour. If you are as immune as you claim, you can give me more than 30 minutes, can't you?"

We agreed to split the difference at 45 minutes. A compromise.

Max: "Any other 'ground rules' you're forgetting?"

Me: "Probably, but nothing else I can think of right now."

Max: "Well, I have a few more. First, I get the whole 45 minutes. No matter what. There is no quitting allowed. It doesn't matter if you feel a loss coming on. You can't forfeit the win over to me. We are going to see this through."

Me: a sheepish "Okay."

Max: "Also, you may not physically block or deflect my efforts in any way. You can do whatever you want mentally, you know, think about grandma, or piles of garbage, whatever distracts you from arousal, but no twisting or moving of any kind. You only move when, where and how I say to."

Me: "I understand."

Max: "No matter who wins, this is just between us. I don't want our other friends or the other people on or floor to know about this. Bragging rights are just between us. Even between us, it might be better that we never mention this again. This is a one-time only thing that begins and ends tonight."

Me: "Agreed."

Max: "My last and most important ground rule. This cannot affect our friendship. This silly bet is just for fun. You are a good roommate and friend. That's more important to me than winning a bet. I want you to know that I am not trying to convert you. I respect your heterosexuality. I am going to win this bet, bet, but after, we have to go on as normal. After tonight, this never happened."

He had clearly given this some thought. I said, "Deal."

Max said, "Go lay down on your bed, on your back."

I asked, "Should I take off my shorts or anything?" Despite it being November, like many other resident college kids, I wore shorts most days.

Max walked over to our door and turned the lock. We were friends with most of the other guys on our floor and sometimes they felt free walk right in without even knocking. Tonight would not the night for that surprise. Max answered, "No. I'll take care of everything."

He went to the sink and wetted a small wad of paper towels. He placed the wet towels, a dry towel and a bottle of massage oil on my nightstand next to my bed. He looked down at me and said, "Slide down a little and put your feet up on the bar at the foot of the bed. Now reach your arms up hold onto the bars of the headboard. Don't let go until I tell you to."

This was an awkward situation. What had I gotten myself into? I already felt vulnerable. With my arms raised over my head, I felt my shirt ride up a little, exposing a strip of bare skin above the waistline of my shorts. Max noticed it too and couldn't resist swiping a finger across my tender lower abdomen. I flinched and gasped at the sensation. I said, "Hey, we didn't talk about that! I think we need to make 'no tickling' one of the ground rules."

Max giggled. "Sorry. I saw that and couldn't help myself. Don't worry. This isn't about tickling. I promise."

He took his phone out of his pocket, tapped at the screen and showed me the display. 45 minutes had begun to count down. He set his phone down on my nightstand by the massage oil. Then he went and got his desk chair and set it at the foot of my bed. He sat, untied my right sneaker, slipped it off and began to massage my foot. This must be part of the foreplay he had mentioned. He soon did the same with my left foot. The massage was feeling good. After a minute, he removed my socks. My feet had been trapped inside my shoes all day. Now they were free, exposed and sensitive. I don't generally have a foot odor problem, but I had a flash of worry as Max's face was just inches away. He didn't seem to react so I guess I was okay. Max gently stroked up and down my arches. It was a very light tickle that felt nice. He wasn't torturing me. He kept his promise.

Next, he began working his way up massaging my calves. He worked his way higher and higher while rotating between my left and right legs. When he made it up to my shorts he continued inside the legs. He worked my thighs. I was relaxing more and more. He was good at this and I couldn't help but enjoy the attention. Either his knuckles or fingertips grazed my scrotum a couple of times causing me to jerk a little with each shocking touch.

He stood and unbuttoned and unzipped my shorts before pulling them completely off. He moved his chair to the side of the bed and sat. My underwear was still on, but he turned his attention higher. He began to unbutton my shirt from the top down. After undoing the bottom button, he spread the shirt completely open, revealing the full expanse of my smooth, lean chest and stomach. He let me lay there a moment, feeling both the cool air of the room as well as his peering eyes on my exposed skin. Max and my round innie belly button were staring at each other. Well, my belly button was usually round, but with my arms reaching up, it was more like a vertical oval.

He began to run his fingers around my chest. I was worried about what was to come. He had promised no tickling. Soon his fingers slid down to my sides and stroked lightly up and down from my arm pits to my hips. Again, it was just a light tickle, but I couldn't suppress a physical response. Goosebumps sprang up over my whole body. I saw Max smile, pleased with himself.

Next, he lightly swiped strokes across my lower tummy. This didn't help the goosebumps go away and I quivered with each pass over the sensitive area. Then he drew circles with his fingers around my navel. He hooked a finger under the waistband of my underwear. At this point I was surprised and ashamed to realize that I had a growing bulge just south of where Max was currently focusing his attention. He was sliding his finger across my skin under my waistband and working lower. He eventually made it to my pubic hair, which I kept neatly trimmed to a quarter of an inch, and he explored the region.

Max stood up, moved to foot of the bed, reached up and pulled my underwear off. He cast the underwear aside as my partially erect penis sprang free. He climbed onto bed, kneeling between my spread legs, and stared down his awaiting prey. He reached over to the nightstand and grabbed the massage oil. He lubricated his hands and then, leaving my shaft alone for time being, he surprised me by stroking my balls. My sack instantly tightened in response and my shaft grew another degree firmer. He continued to work on my scrotum, careful not to mishandle the sensitive organ.

I was trying to think of anything else. I really was. Any type of mental distraction. It wasn't working. I was fascinated by what Max was doing to me. My cock jumped up another notch. My partial erection was now close to a full and he hadn't even touched the shaft yet. Max was looking at it, though. Appraising it and proud of his accomplishment. I began to think for the first time that I might lose this bet.

Done foundling my balls, he reach both hands back up to my armpits and slowly dragged his fingers down my sides, strumming my rib cage, across slight mound of my lower belly and finally he ahold of my awaiting shaft. The touch of someone else's hand, to me, is so much more exciting that of my own. Maybe it was because I've never been touched this was by a man before, but Max's touch was electrifying and I gasped. It felt like a jolt and I had now completed my journey to full erection.

He began with simple up and down strokes with his well-oiled right hand. It felt amazing. He reintroduced his left hand to my ball sack, twirling lightly. I was definitely going to lose this bet. His strokes began to change. He was now continuing up over the sensitive mushroom cap and finishing with a swirl. This was driving me crazy and it was killing me to maintain my grip on the headboard bars. Next he pressed his palms together and enveloped me inside of this makeshift cavity created with his two hands. He slid up and down and used a twisting motion that almost did me in. He must have realized I was close and, possibly not wanting his fun to end too soon, he changed tack.

With Max kneeling between my legs, the sensitive underside of my throbbing shaft was facing him. He gripped my shaft in his right hand again and began twirling his thumb in clockwise circles around my most sensitive spot - just under the head. The fingers of his left hand resumed a light tickle on my scrotum. The combination of the two sensations was proving to be too much. I was about to burst and powerless to stop it. I threw back my head into my pillow and arched my back as I exploded my load onto my stomach and chest. Max kept up his relentless circles until I was milked dry. He seemed to know exactly when to stop, before pleasure turned to pain.

Without a word, he reached to the night stand for the wet and dry towels and cleaned up the mess I had made. It was an oddly intimate act. To this point neither of us had yet spoken. I began to sit up and Max said, "Where do you think you're going?"

I said, "What do mean? You got me. You clearly won the bet."

He said, "Yes I did, but," he leaned over and picked his phone up off the nightstand, "my 45 minutes isn't up yet."

I was confused. "But you won. The bet was that you had 45 minutes to make me cum. You did it." I tried sitting up again.

He gently pushed me back down. "We agreed to list of ground rules. One of those rules was that I would get the full 45 minutes. No matter what. No quitting." He turned his phone to show me the display. Only 23 minutes had passed. Almost half of the time still remained.

I stammered, "Right, but... Didn't you... What do you..."

Max said, "I am not done with you yet. You're mine for another 22 minutes. I am going to get you two times!"

I couldn't believe what I just heard. "That wasn't in the rules."

"Me having the full amount of time, no matter what, was in the rules."

I glanced down at my spent, shriveled cock. It was still recovering from the events of a few moments ago. "Dude, you drained me. I've got nothing else to give."

Max said, "You let me worry about that. Now I want you to slip your arms out of your shirt and flip over onto your stomach."

I looked at him with concern on my face. He said, "Don't worry. I will not be breaking any rules."

I rolled over. Max straddled me and began giving me a back massage. I'd never been massaged by a man before. He expertly worked my neck, shoulders, arms and back. His strong hands dug deep and it felt good. It was far superior to any feeble back rub I'd been given in the past. As he kneaded my muscles, I began to tingle and even my frightened penis began to come back to life. He must have used up a good 10 minutes of his remaining 22 on the massage.

Max instructed me to roll over again. I did so. My refractory period had ended and, while I was still soft, my penis had returned to a more normal flaccid state. He spread my legs apart and, once again, took position kneeling between them. He leaned forward placing his palms flat down on the bed, flanking my sides, lowered his head and sucked a nipple. I had never been a fan of nipple play in the past, but when Max did, my nipples hardened in affirmative response. He moved across and addressed the other nipple.