UMD Stories

The Game Chronicles I
Story by webcamplayer
Posted 1/18/25     841 views
A new story. Episode one, because it's rather lengthy.

*

I guess that my story begins on October 5th, the day of my twentieth birthday. My twin sister was at the same university, and so we decided to celebrate together. Neither of us were particularly fond of clubbing or pubbing, so we got our respective friends together and went bowling. Perhaps oddly, we didn't really share the same friendship group. Jane had hers, and I had mine, even if we were still vaguely aware of who was who in each other's. That night, I took the three people that were my housemates, and she took the three people that were hers, and we played against each other.

I had forgotten that one of her housemates was new. Someone had intercalated during the summer due to health reasons, and so could no longer take up the place in her house. I hadn't met the replacement before.

Stuart.

Stuart was how can I put this eye-catching. It might have been early autumn, but the temperature was way up in the mid-twenties, and Stuart was wearing a T-shirt that, it would be fair to say, showed him off in the best way possible. It was easy to tell that he was someone who worked out a great deal, and I took some considerable delight in watching his muscles bulge each time he bowled.

Jane could see me looking or maybe simply sensed that I was. We sometimes had that thing going on that twins sometimes do, where we knew what each other was thinking or doing. She came over to me at the end of one of the games.

"So, Richard, you like the look of our new housemate, do you?"

I said that I did. There was little point in hiding it. She knew it anyway.

"Do you want me to introduce you?" she asked.

"We don't need introducing. We've been here for the last hour."

"But you haven't even said hello to him."

"I kind of did."

"You kind of didn't. Go and talk to him. You're not going to find out unless you do."

"Find out what?"

"You know exactly what I mean."

I looked across at Stuart again.

"There's no way someone like that would be interested in me. He's probably not even"

"He is."

I should have known, really, but my "gaydar" has never really been in tip-top condition. In fact, I was hopeless at working out who was and who was not gay.

"He's probably got a boyfriend," I said.

"He hasn't."

"Sure?"

"I live with him. I know. There's never been as much as a mention of anyone. Talk to him. He's nice."

I didn't. We just carried on playing, with Jane's teaming beating my own time after time. I should have suggested that we mix the teams up after a while, but didn't want to. I don't like being forced into talking with someone I don't know. Sometimes I can do it, but other times I find it more than a little scary.

It was only when we were returning the shoes that I found myself next to Stuart. Virtually everyone else had gone to the toilets, and we were stuck there waiting for everyone else.

"Good game," he said, seemingly unable to think of anything more original to say. Perhaps he didn't find smalltalk easy either.

"Yeah," I replied. "I think you won all of them, though."

"Jealous?"

"Of your skills?"

"No, just of our team winning."

"Your team only won because of you."

"Ah, so now it's my fault you lost?"

He was smiling. Nice smile.

"Something like that."

I looked around, hoping that the others would soon be coming back. I was beginning to feel awkward.

"I don't know what they're doing. It's taking them longer in the loo than it did to play a game."

"You like playing games, do you?"

"Yeah. I guess so. We've gone bowling for a while now."

"I wasn't talking about those types of games."

I paused for a moment, not sure if I wanted to continue with the conversation, but something told me to carry on. Just for a little while longer.

"What kind of games do you mean, then?"

"Ones with stakes."

Now my instinct was to absolutely not carry on with the conversation. I didn't quite know what Stuart was getting at, but I was getting the general gist. And yet, I liked the guy. Besides, the others would be back soon, and then it would be over. What was wrong with a bit of flirting?

"What kind of stakes?"

Stuart smiled again, and then he leant in towards me, and whispered in my ear.

"Horny ones," he said.

I could feel my face blushingand my dick hardening.

"Do you want to play with me?" he asked.

"What games do you play?" I blurted out.

"Anything and everything." He moved in towards me again and whispered. "I like the thrill of the game. The chance of winning and making the other guy squirm - and the risk of losing, of course." He moved away, and continued talking. "Board games, card games, games of chance. I don't care, really."

"Are you talking about" I lowered my voice. "Are you talking about strip poker?"

Stuart laughed.

"You make it sound like it's some heinous sin," he said. "It's just a bit of fun. I'm sure you've done something similar. Everyone has."

The problem is that I hadn't. I'd always been an introvert, really. Nobody had seen me naked, other than in the changing rooms at the swimming pool. And I was still a virgin.

"Sure," I said. "Everyone's done that."

"There you go, then. Give me your phone."

I handed my phone to him, and he created a contact and entered his number.

"Text me when your house is free, and we'll see how competitive you are."

"Are you competitive?"

"I think you already know the answer to that."

Just then, the others started walking over towards us, and the moment had passed. My sister spoke to me as we left for him.

"You two seemed to be getting on quite well back there."

"Is that why you took so long?"

"Of course," she said, and went back over to her housemates.

*

I told my sister about how Stuart wanted to see me again I left out the bit about playing games, I thought there were some things that she didn't need to know. And so, a week later, I texted him to let him know that my house would be free the next night.

I wondered if his talk about playing games was just that talk. A way of making himself seem approachable. I hadn't played anything like that since I mooned at a friend in a rather tame game of truth or dare .

Needless to say, the game of Trivial Pursuit that I had that night with Stuart was a very different affair. He brought the game with him, and had his own rules ready. He was oddly serious about it. Both players start off with seven items of clothing, and they take one off each time their opponent got a wedge. The last item comes off when someone wins the whole game.

As we played the game over the next hour or so, I realised that Stuart wasn't just playing to get my clothes off. He actually enjoyed the game itself, it seemed. He was getting off on the risk. And I also began to realise that he was nervous about losing just like I was.

Everything was lighthearted enough to start with, with general silliness when the first couple of items of clothing came off. But, as the game wore on, it got a bit more serious. We didn't care about taking socks and shoes off, but neither of us wanted to be the first one to show some actual flesh. For that reason, I realised that my best course of action was to pursue getting the colour wedge that corresponded to the subject of which I had the most knowledge. If I got it right, he'd have to take his shirt or jeans off. I was keen to get his off before he got mine off.
I could see his disappointment when I got the question right, and he had to remove something. I wondered what he was take off jeans or shirt. I know what I would have gone for if it was me in that position. He thought about it for a few moments, and then reluctantly took his shirt off.

"Are you enjoying the view?" he asked, as he put his shirt down on the bed.

"Yeah," I replied. "But I'm more thankful that it's not me losing."

Stuart smiled.

"You're learning," he said.

"I get the impression you've done this before."

"Not as often as you'd think. A couple of times a couple of years ago. Just for a laugh. But I've thought about it ever since."

"What made you think that I'd play?"

"I don't know," Stuart said. "I'd only just met you. If you brushed me off it wouldn't matter quite so much."

"Thanks."

"I didn't mean it like that."

"I know."

"You don't have to carry on if you don't want to."

"You say that when I'm winning?" I said, grinning. "Nah. I want to get you naked."

I suppose I could write here that it was a close game, blah blah blah. But it wasn't. I beat him conclusively. By the end, I was worrying far less about losing and much more interested in gently mocking Stuart for suggesting the game and then sucking at it. Yeah, I was hard by the time he was sitting in his boxers, but Stuart knew nothing of that as my jeans were still on and so was my shirt, for that matter. When he pulled his shorts off, he stood there with his hands over his dick.

"I don't think that's allowed," I said, laughing.

He took his hands away, and blushed. It was a very nice view, but I was more satisfied that I had kept my dignity, and I realised the whole thing wouldn't have been as much fun if one of us didn't care about losing. We had both wanted to win, and that was key to our enjoyment.

"Thank you for a fun evening," Stuart said, when we were standing at the front door, and was about to leave. "I had a good time."

"I did, too."

"My place next time?"

I nodded.

"If you like. Does that mean you want revenge?"

"Of course."

"You'll have to do better than you did tonight. But won't the fun have gone once we've both lost?"

"There are other things to play for than just getting naked," Stuart said, with surprising seriousness.

"Oh?"

"It's a fun way to explore things, don't you think?"

"I do."

With that, he said goodbye and walked off into the night. I wondered if I would hear from him again.

*

It was five days later when my mobile phone started vibrating at eight o' clock in the morning. I swore to myself as I reached out of bed and picked it up, but my bad mood lifted when I saw the message was from Stuart: "Hey, Wanna play? Tonight at 8pm. Bring a change of clothes."

I was intrigued. Why would I need to take a change of clothing? Whatever the reason, I was pleased to hear from Stuart, and was feeling more relaxed about meeting him for a second time. I felt I could trust him not to get me doing things I didn't want to do.

I spent all day thinking about what he might have in store if, indeed, he had anything in store at all. I found myself outside his door at ten minutes to eight. He opened the front door before I had time to press the bell.

"I thought you'd be early," he said, smiling. "You'll be glad to know that everyone is out for the night. Including your sister."

"That's good," I said, as I walked in. "I didn't want her walking on me sitting there naked in front of a trivial pursuit board."

"No trivial pursuit tonight," Stuart said, shutting the door behind me. "Did you bring some spare clothes?"

I said that I did.

"Good. Ready for some fun?"

I followed him upstairs into his bedroom. He picked a pack of playing cards off his computer desk and held them up in the air.

"Happy to play a game of chance tonight?" he asked.

"Is that because you can't win a game of skill?" I asked, grinning.

"You won't be smiling later."

Stuart had in mind a straightforward game of guessing whether a card was red or black. When your opponent got three right in a row, you took off an item of clothing. It all seemed straightforward, until he said:

"The first one to be down to their boxers will then pick a card to see what their punishment is. If they pick a heart, then they have to guess for twenty cards, with a hole being cut in their boxers for each one wrong."

"Hence why you wanted me to bring some spare clothes."

"Exactly. If it's a club, then it's a cold shower."

"With or without boxers?"

"Either. If it's a diamond, then they get spanked over the winner's knee."

I wasn't sure I wanted to do that, but I trusted him.

"And if it's a spade, they go out in the back garden and roll around in the mud."

They were things I wouldn't normally do, or even think of doing, but the thought of them got me surprisingly excited.

"OK," I found myself saying. "But this is insane. How do you come up with these ideas?"

"Don't know. They kind of just come to me when I'm"

"OK. I get the idea."

We spent the next half an hour calling out whether the next card was going to be red or black. It would have been the most boring thing imaginable if it wasn't for the fact that clothes were slowly coming off, and there was a chance of real humiliation after.

I had already realised that if I kept playing games with Stuart, I was eventually going to lose. A winning streak can't go on forever, especially in inane games of luck that we were now playing. And yet, despite that, I was doing pretty well. I still had my shirt and jeans on whereas Stuart was once again shirtless. I just had to get his jeans off, and then he would have lost. That wouldn't have been so bad if it wasn't for the possibility of getting covered in mud in my sister's back garden. It all seems so ridiculous now. And stupidly risky. What would happen if she and her friends came home early?

And then, as was bound to happen, my luck ran out and Stuart had a run of good fortune.

"Do you mind if I help you get out of your jeans?" he said, just as I was about to take them off.

I would have been something of a spoilsport if I had said no, but I could already feel myself blushing. I felt my dick getting harder and harder, and when my trousers were lowered past it, my boxers could hardly contain it.

"Well, well," Stuart said. "Looks like you've been looking forward to this, after all. So, which of the forfeits are you hoping for?"

"None of them," I told him.

That wasn't strictly true. While I didn't want to make a fool of myself in front of him, I was rather liking the fun dynamic of the games probably more than I would have done had we been having sex.

"You need to pick a card," Stuart said.

This was the bit I wasn't looking forward to partly because I didn't know which of the forfeits was the worst. The cutting of the boxers would probably be the least worst. Stuart was going to get me naked at some point, that was for a certainty. But the others? I didn't fancy being spanked I wasn't good with pain of any kind. A cold shower? No thanks. Rolling around in mud? That was just weird. I wondered how he had even dreamt that one up. Unlessunless he wanted to do it himself. That kind of made sense. Perhaps he was disappointed that he had lost.

It didn't matter now. A forfeit had to be done, and I had a horrible feeling that the mud one would be the one that I picked. It was somehow inevitable from the outset.

We went outside. Stuart had got dressed, but I was still in my boxers. We walked down the garden to the sizeable muddy area.

"How have you get this much mud?" I asked.

Stuart smiled.

"Luck," he said. "A pipe that runs under the garden burst a week or so ago. It's been like that ever since."

"Have you been in it yourself?"

"Why would I want to do that?"

"It's what you're into, isn't it?"

Stuart didn't reply, but waited for me to go in the mud.

"What do you want me to do?" I asked.

"Dive in."

I walked gingerly into the mud, squirming at the feel of it on my feet.

"Lie down in it," Stuart said.

I turned to face him, and had an idea.

"Make me," I said.

Stuart stared at me, not really knowing what to do.

"That's what you want, isn't it?" I went on. "You want to come in here and mud wrestle. Now's your chance."
Stuart hesitated for a moment or two, and then stripped down to his boxers and wandered in to join me. The mud was slippery, and I saw him lose his footing, and went over to catch him before he fell down. We held on to each other, not quite sure of what we were to do next.

"First one to have their boxers removed is the loser," Stuart said.

I hesitated a moment, and then nodded. We were on the ground within seconds, covered in mud from top to bottom before we even knew it. We writhed around in the mud for a minute or two, both of us turned on by the experience. And then, I found myself pinned to the ground, with Stuart straddling me, mud dripping from his hair onto my face.

"Having fun?" he asked.

"Well, it's not exactly what I had planned for the evening, to be honest."

"Surprises can be good, though, right? Besides, seems to me that you're enjoying yourself."

He reached behind him and took hold of my dick through my boxers. I squirmed, partly in pleasure, and partly in embarrassment, and I also knew it wouldn't take much to make me cum. Half a minute of his hand around me and I'd be done. That worried me a bit. I didn't want him to think I was a lightweight and came at the least little thing. He pulled on my dick a little, a threat of perhaps doing it harder. Was that what I wanted? I wasn't sure.

I had to get him off me if I was going to win, and he was undoubtedly much stronger and heavier than I was. There was only one tactic that I thought might work, and so I reached up and ruthlessly started tickling his chest. He jerked back instantly, screaming with laughter. I managed to push him off me, and then I was the one pinning him down on the ground, tickling with one hand and trying to pull his boxers down with the other. It didn't take long for me to get them down far enough to reveal his throbbing dick. I'd seen him naked before, but that was a tentative game, where he'd been or at least pretended to be embarrassed by being naked. Now, however, he was simply turned on and ready to explode.

I put my hand around his dick, and moved it up and down slowly, the mud acting as the best lubricant possible.

"Do it," he said, quietly. "Make me cum."

I kept wanking him slowly, and he whimpered beneath me.

"I'm going to cum," he said, almost to himself.

And then I realised that everything between us had been about games and playing, and it should continue that way. There was plenty more mileage in it yet. I wasn't going to make it that easy for him to cum, and so I stopped wanking him, and smiled.

"You have to earn that," I said.

With that I pulled his boxers off completely and dropped them on his face. Then I stood up and made my way out of the mud.

He tossed his boxers into the mud beside him and sat up.

"You've got to be kidding me?"

I turned back around to face him.

"You've got to win the next round for that," I said, grinning.

Then, I took off my boxers, threw them at him, and went to get showered.

(End of part one)
Tagged male
Comments:
Slimon:
1/22/25
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This story is HOT. would love to play with those two.
Longing for part 2
washme01:
5/7/25
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Hot story.
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