I slipped into bed and ran the evening's delicious events through my mind. Kent had made me a beneficiary of his latest conquest. But there was more to it than that. Kent had once again done what he likes doing best, showing off in front of other guys. I reasoned that he didn't care much who was serving him, just that he was getting it while being watched, or photographed, or both.
For my part, I didn't mind being a party to this anymore. The pictures of the first event were a shock, but they didn't actually cause me any trouble. Quite the opposite was true. Since Kent passed around those photos of me covered in his cum, I'd had more sex than ever before. That wasn't saying much, but still I'd gotten used to the idea that Kent could show off his success with me whenever and to whomever it pleased him. It gave me a little bit of a rush to think that Kent could relate how he'd had his pleasure with me, and then make sure his friends met me. Jim had known the score when we met, and it was actually fun.
When the video turned up from the second event, I found it exciting. Deep down, it turned me on that the other guys had seen it before I arrived. I was comfortable with these guys, and felt that Kent wouldn't let it go too far since he was involved himself. Sure, he was on top, but he was still having sex with another guy. This is not something he'd want absolutely everyone to know anymore than I did. He had an image to maintain as a rugged frat jock. Sure, I could understand Kent's interest in having an audience. This turned me on too. But I knew that this had its limits. With this realization, I hoped I might be able to turn it to advantage somehow. This was for another day.
Mike, by contrast, did not like being watched. He did not like being watched serving Kent, in particular. He'd done his job well enough on the other three of us, but it was merely that. He hated doing Kent. He struggled more with Kent's dick than with the rest of us combined. Maybe it was just his first taste of a man than was unnerving, and by the time he'd gotten to me he was used to it. I didn't believe it, though. Kent was harder for him.
Mike had made a bet, and he lost. He honored his obligation and got down on his knees to suck Kent and Kent's choice of friends. I had to admire him for keeping his word. As far as his choice, he preferred sucking four guys to getting fucked by one. Was it getting fucked at all, or just getting it from Kent? If I understood Mike, he was bitter about losing to Kent. I left him just enough of a hook tonight to get him thinking about evening up the score. This, too, was more work for later.
Recounting the sequence of the last couple of hours had my cock swelling up with pleasure. Mike had just taken care of it, to my instructions, but it was ready for more. My roommate, a nice enough fellow but not someone I spent much time with, was sound asleep. I thought of Mike chugging his beer while watching the tape of Kent mastering my ass. Surely Kent had planned even this. He'd left Mike in front of the video to consider his options. He could take my place as Kent's friends cheered Mike's submission. He'd grab onto the couch, surrendering his manhood for a few humiliating minutes as Kent pounded him from behind. Or he could degrade himself by taking the same crowd to orgasm in his mouth, one by one. No matter what Mike chose, Kent won.
Imagining myself in Mike's predicament as I ran my palm over my crotch roused my penis to a full force hard-on. In a moment I'd be stroking myself to orgasm, the covers thrown down and open to the night. The added excitement from the chance of getting caught beating off helped tighten my balls. I picked up speed on my shaft. I started to draw deeper, less frequent breaths as the precum glistened from my dickhead. I paused briefly to watch the moisture shine in the light coming through the window, and to enjoy moving close to and then back from the edge of orgasm. I drew a deep breath and started my final push, beating hard and fast as I imagined telling Kent that I'd let him fuck me in front of his friends. I was Mike, and I'd decided to pay off big time.
"Yeah, guys, gather around the couch. You're going to see this stud claim his prize. Go ahead and cheer him on. Watch him bury a load of hot manhood inside my ass," I mouthed to myself as I whipped my meat and ground my hips against the sheets. The fantasy mixed supremely with the recent memory of actually taking it. I recalled how it felt to get it in the locker room in front of Jim as I imagined pleasing Kent in front of his crowd. I was going to have a good one coming, even if it was the second in an evening.
I arched my back upwards and aimed my cock to spray down my chest. It was as if I stood at the edge of the diving board, inching my feet backwards until my toes were no longer strong enough to hold me. I had begun to fall towards the warm water, out of control and readying for the splash. In a second I'd be in the pool, decelerating with a flurry of bubbles as I sank below the surface. I'd watch the sun through the waves on the surface, and for just a moment feel as though I was floating. Anticipation is always the best part of sex, and I was relishing the moment. This would be a good one.
The telephone yanked me out of my dive. I was shooting an above average load of cream onto my chest as I crashed back onto the mattress. I flailed my arms up onto the desk to grab the receiver. As I grasped it and hit the talk button, I rolled over. I felt another discharge, and felt the semen that pooled in a fold of the sheets next to my glans. I was ejaculating into my sheets, and also smearing the goo that had splattered across my chest onto my pillow. It had been a good orgasm indeed, and now the blockheaded lifeguard was screaming at me for doing yet another back flip off the high dive. Busted again.
"Hello-uh," I panted into the phone.
"You didn't have to run for the phone, did you?" asked Mike. I decided not to tell him anything.
"No problem, Mike. What's up?" I couldn't have sounded more collected if it were a Tuesday afternoon. In truth I was throwing on a bathrobe and letting myself out the door. If we were going to have the conversation I expected, I didn't need a groggy roommate listening. I certainly didn't care him to realize that I was talking about man-to-man sex with another guy, and that the room reeked of fresh cum. The floor lounge was empty. I settled in without turning on the light as Mike began to explain.
After a few false starts, Mike said he wanted "in." I thought for a moment. I recalled promising him that he could practice on my ass, but I hoped that's not what he meant. Not right now, anyway.
"I want to get even with Kent as much as you and the others do." Mike said that so sharply that it seemed to bring him some relief when he'd gotten it out. Now it was my turn.
"Yeah, okay. I thought you might. First, let me ask you a few questions." This had all hit way too quickly. I'd wanted some time to think about this and plan it out. I needed to buy some time. "How was it that you got into this situation anyhow? I mean, what was this bet all about?"
Mike went on to explain that he'd run into Kent at a party. Mike had been bragging about his basketball abilities to anyone who would listen, and it caught Kent's attention.
"Kent comes up to me and says he'll bet anything he can beat me at a game of one on one. Hell, I have trouble finding opponents! I've been playing basketball - and winning games - since I turned 6 years old. Now this smartass wants to make a bet." Mike paused for a few seconds. I heard a bottle pull clear of his lips and enough time for a swallow. Mike was having another beer, on top of quite a few beers and a few cum shots earlier tonight.
"I told him that he could just blow me now, because he was going to loose. So he says he'll take that bet, but make it a blowjob for the winner and three of his friends." Mike stopped for a breath. "My buddies were standing there with me, and they counted themselves off, one, two, three. I had to shake on it."
"So how did Kent beat the basketball star?" I asked.
"He psyched me out. It doesn't happen much, but he knew how to do it. Every time he made a shot, he'd brush his hands a little lower on his shorts. I couldn't concentrate and just fell apart. I kept thinking of how awful it would be to be going down on this guy, and that made it happen."
"Do your friends know that you lost yet?" This time I used a deliberate and concerned tone, wanting him to think I was completely on his side. The plan was coming together.
"No. And I want to get my payback before I have to tell them. Got any ideas?" Mike was hot to get moving.
"Yeah, I do. But one more question before we get to that." I was enjoying the story, and probably would be hard again if I wasn't twice spent and a little chilled in the dark lounge room. "Where did the alternate of taking it up the ass instead of going down on four guys come in?"
"Oh, that. Kent threw that in at the last minute. When I went over to, uh, pay up, he offered me that choice. I thought about it. I probably would have done it, but I saw the tape of you getting reamed by Kent. I realized that I didn't ever want to take it like that. Almost anything but getting it in the ass!" Mike was playing right into the plan I'd scrambled together in the last couple of minutes.
"How about being on top of Kent?" I asked. "You know he's never given it up. Wouldn't it be sweet to hold him down and make him take it for a change? I think all of us would like to see that." I paused to let him savor the thought. "I think you'd go first. You deserve the biggest payback. I'd love to see Kent's face as you creamed into him."
"Oh fuck, yeah! I'd love to crack his ass open. I want him to beg me for it and take it for an hour." Mike sounded more awake with the idea than he had all night. "Now how do I get him to take it?" Funny he should ask!
"You're sure you can beat him in a rematch?" I asked tentatively. "If you're as good as you say, you should be able to win. You have the height, the skill, and the practice. I wouldn't go against him in softball, but he should be out of his league with you on a basketball court." I laid it on to encourage Mike to jump at the idea. It worked perfectly.
"Sure thing! I'd nail him now. I'm pissed off enough to win on that alone. But he'd never agree to it. Why would he?" Mike was speaking more quickly, obviously excited.
"Leave that to me. I can talk him into it. If you're willing to bet an evening of total sexual submission, including an hour-long fuck, I have all the bait I need. He'll take it. He's arrogant enough to fall for it." I said it like I believed it, but in truth I was amazed as the words came out of my mouth.
"Do it! Set it up! I'll call you tomorrow night." Mike no sooner finished the words and he hung up.
I sat for a moment in the dark and wondered what had just happened. Would Mike sober up and forget it all? Would Kent, in fact, go for a rematch? Most importantly, how could I get something no matter how the game went? The only thing clear is that I'd have to sleep on it. I was starting to sober up and my dick hurt from doing overtime. Sleep, already!
I slipped into the room and quietly set the phone down. The bathrobe fell to its usual place on the floor as I settled onto the bed. In a moment I had my face buried in the pillow, realizing moments later that I had cum on my face once again.
The next morning, I showered with a vengeance. Then I called Kent. All I left in the message was that he wouldn't believe what had happened, and that he should call me right away. He did, an hour later.
"Let me guess, Mike let you fuck him on the lawn in front of the house." Kent was his normal, cocky self. Just right.
"Almost as good. He wants a rematch. The prize will be an evening of total submission, including a good, long fuck for the winner." I declared it like I was reading an award letter. There was no immediate response, so I continued. "Kent, the dumb bastard didn't learn the first time. How'd you like to add another notch to your belt and claim Mike's ass like you did mine?"
"So he is crazy. I whomped him good the first time. I can do it again. Seems too easy." Kent wasn't nearly as enthused as Mike was last night.
"Just for grins, I get to help with the evening. I trust you'll make Mike blow me while you fuck him. I'd love to see him take it in both ends." And so would Kent, I bet. He liked being watched; maybe he'd really like having help.
"You're sick! I like it." Kent was on board. We set the event for Monday at 7 pm. The outdoor courts at the gym center were sure to be open at that time, and it would allow a leisurely evening for the winner.
When Mike called that evening, I relayed the news and set the date with him. As I hung up, it did all seem too easy. Here were two guys dead set at keeping their assholes safe from intruders, yet each gladly willing to bet this element of their masculinity on the chance to defile a rival. Didn't they realize that someone was going to loose? I needed some insurance that the loser would go though with the deal.
On Monday evening we met a Mike's apartment, and I explained what this safety catch would be.
"I brought my camera for some pre-game photos. I'll take a few incriminating photos of each of you. Mike, if you loose and don't pay up, Kent gets the roll. Kent, if you bail, Mike gets the film. If you guys keep your bargain, then nobody ever sees the photos. Fair enough?" I asked as I looked at each of them.
"I don't think pictures were in the deal." Kent protested. "We can shake hands on it. That's enough!"
"Mike, are you happy with that?" I asked, all the while projecting the word "NO" into his head. "Do you trust Kent to let you have him if you win, or do you want insurance on it?"
"As long as the roll never gets developed, I think it's a good idea to have it." Mike looked squarely at Kent as he said it. Kent looked completely shocked.
"No big deal guys. Just enough to make sure you keep your end of the deal." I offered, and then turned to Mike. "Get on your knees in front of Kent, and put your fingers on the band of his sweats."
Mike did as I directed, and Kent took a step forward so that his crotch was only a few inches from Mike's face.
"Get comfortable, buddy. You'll be back there tonight, just like that." Kent sneered at Mike. I snapped a picture of Mike about to undress Kent.
"Now pull the sweats to his knees and move your lips right up next to his jock." I directed.
Mike paused, but Kent egged him on. "You've done all this before, you know how to do it, cocksucker." A shot from over Mike's shoulder made it look like he was kissing Kent's pouch. The excitement was getting to Kent. He no longer hung loosely in his jock. Having Mike on his knees again obviously pleased him. I decided to go for one more.
"Okay, Mike, pull down Kent's jock far enough that his cock flops out." I couldn't believe how well this was going.
"Yeah, baby. Do it for me. Let me out. Check out your dinner, boy!" Kent was enjoying this. As I framed the shot and released the shutter, it looked through the viewfinder that Mike was going to be having a sperm snack again. Mike even had his lips parted a bit as he was starting to speak. Perfect.
"That's as much as you'll get tonight, you fucker!" Mike protested. Kent did not object to his title.
"Okay, enough boys. Now switch. Same sequence, trade places." Kent could hardly object, and Mike was clearly thrilled. When it came time for the jock to come down, Mike was fully erect and aiming right for Kent's nose. I really wanted to see that picture.
"Hey, anyone for stale cheese puffs?" I hoisted an aged and open foil packet out of my camera bag. No takers. The guys packed up and we headed over to the gym. I tossed the bag into the trashcan just outside the main door. Right on time, 7:00. As the interior door opened ahead of us, I briefly caught the image of my roommate. Right on plan. The game could begin.
In about half an hour, we three would know which man would surrender his cherry. We'd know which man would be enjoying an evening at the expense of the other, and who would have bragging rights and leverage the next time he wanted a sexual favor. One of these fine studs would become a bottom before the night was out, submissively enduring the penetrations of the other, and eventually accepting the orgasm of his victor. In any case, I would be on hand to enjoy it. I frankly didn't care who won.