Chess: Winner fucks loser

Heavy drops of rain came pouring down my face as I reached the pinnacle of my new found happiness. Everything seemed surreal; all I could remember was we were playing chess. Then here I was in the corner of the pool with my trunks yanked down my ankles and my face pushed down the ground as my buddy Will invaded my tight little pucker with his cock. How I got into this situation is quite a story actually. 

“No stupid! You don’t just do that! He’s gonna take your Queen, dumb-ass!” A guy yelled as I put my horse on a black square obviously trying to attack my opponent’s King. I looked for the guy and realized he was standing behind me. He was small compared to me. 

“Aww shut up! I’m the one playing here dude!” I thought. But he was right; my Queen was gonna get taken if I moved my horse but since I had so much pride in me, I still stuck with my plan – and, yes, I lost the game. 

After the game, the guy with a big mouth still kept on babbling about how I could have used my rook instead of the horse for cornering the King and stuff until I got fed up with his I-know-better-than-you talks. Lucky for me, the morning bell rang and our teacher went on with her daily stuff and introduced me to the class. 

It was just a week ago when I set foot in the country which I had never thought existed. It was somewhere down the Pacific area close enough to Australia and Indonesia. Anyway, I got a hard time adjusting with my schedules and all. First, we had swimming for sports and I wasn’t comfortable at all being naked and taking a shower with guys. Second, it meant that I had to speak full-on English since I was in an international school. Well, speaking English was a piece of cake although I was extremely shy during my first few weeks; however showering naked with cute guys was a bit scary and exciting for my part. 

I don’t know why but I always got hard whenever I saw guys showering naked; probably because I wasn’t that exposed to that idea. My happy or should I say ‘hiding’ days came. I started doing swimming classes with them and often see my classmates’ ass and sometimes if I was lucky enough, I would see a little bit of their tool. I, horny as hell, easily got a boner from this and often times had a quick wank inside a shower stall. 

I went like this until we all graduated from senior high school fantasizing about my cute classmates sucking my cock or them fucking my mouth. Well I didn’t really get into action until I befriended Will, the natural born bugger, who by the way was the one telling me what best to do in chess.

After two years…

I couldn’t quite remember why but my other mates had gone home a day before the day we all agreed on leaving. We all stayed over at Will’s place and since the other two had gone home, it was just basically Will and I. 

I had been secretly in love with my best buddy Will for more than a year now and didn’t do anything about it knowing that the guy was straight. Will is cute. He has long jet black hair that somehow covers his eyes, a toned body, and possesses a huge member. While I, on the other hand, has trimmed jet black hair, nearly-toned body and a pretty much around average size dick. (I normally have this innocent look that makes girls feel comfortable with me but like they say; looks can be deceiving…)

I don’t know if he knew – or at least suspected a bit – that I was into guys as well (I guess that makes me go swing both ways) because he would sometimes flirt with me or have his leg rub against mine during Geo. 

Anyway, he protested a bit. “Guys, you gotta be jokin’. C’mon, you don’t want me to get stuck here with Dwain, do you? He’s gonna take advantage of me!” Will joked making our mates feel sorry for him.

“Oh hell I would!” I thought but I muttered “Aww c’mon Will. As if I’d waste cum on you!?” Actually I do love to. 

Later that day…

“Dude, wanna go for a swim? C’mon it’s so fucking hot in here! I feel like my ass is burning!” Will tugged my arm to get my attention. 

“Oh well, I guess that’s a good idea.” I said enthusiastically. 

“Just go there. I’ll be with you in a sec.” He grinned. 

In my mind, “what is he up to this time?” and off I went to the pool area in the compound. 

I had stripped down to my trunks and was just waiting for Will to bring his ass up in the pool. I was left curious and was excited a bit on what he was planning on doing so. I mean, there’s gotta be something I just didn’t know. 

For what seemed like 3 minutes, I saw Will making his way to the pool shirtless. How I love seeing him without a shirt on! And I noticed he was carrying something – I guess it was a chess board. “So now we gonna play chess?” I thought.

“How ‘bout a game o’ chess?” He asked.

I just nodded.

So we went in the pool and placed the board on a floating raft. 

“What’s the point of playing this, Will?”

“Well, whoever wins gets to dare or make the loser do whatever the winner wants.”

This excited me a bit. I thought of humiliating dares like Will running round the compound butt naked or he’s got to climb up a tree and start yelling stuff… anyway, the thoughts just drove me off. I couldn’t concentrate on the game. I started to lose piece by piece until Will took my Queen. (I so much rely on Queens.) And just after he had gotten my Queen from me, I lost the entire game. 

But of course, I didn’t want to lose – I didn’t wanna do stupid things that I would regret. But too bad, I just lost which meant I had to do whatever Will ordered me to. 

“So, Dwain, are you ready for this?” 

“I’ve never backed off from anything.” For once, there was uncertainty in my voice.

So swimming to my sides, he got really close to me. He looked at me lustfully and whispered to me ears. “How would you like the winner to fuck the loser eh?”

I was taken aback. I so didn’t know what to say or more likely do in this situation. Trying to maintain my composure, I said with no trail of doubt “I’m up for it boy.” 
And so he moved his hand down to my crotch and gently cupped my balls. His other hand headed to my face and moved it closer to his and we started kissing. He pushed his tongue inside as I hungrily sucked it. I felt his hand walk slowly up my now erect cock and gently jerked it a bit. I was feeling the sensation of his touch on me. 

Without any delay, he swam into the shallow end and pulled me after him. He aggressively yanked down my trunks and exposed my tight ass. He pushed my face on the ground as he kissed my ears, then my neck and my back. 

I felt water droplets on my face and realized it was starting to rain. In spite of the rain, Will still kept going at it. His now hard member (8 inches of meat) started poking my backside. My face still on the ground, he rammed his thick cock in me in one push actually ripping my tight little hole. I felt pain and screamed as loud as I could and tears formed in my eyes. Will, being concerned, asked if I wanted him to stop. 

“No, just keep going.” I was able to mutter.

“Okay, just relax. I’ll go slow.” He said while caressing my back relaxing me. (I guess)

He waited until I wasn’t tense anymore then he moved rhythmically. He started pounding my ass so bad it felt like I had a broom up my ass. I could feel his balls slapping against my thighs and his pubes tickling me. From then on, I just realized he had his whole cock in me. 

It was still raining fairly moderate. By this time, Will was jacking me off while ramming his cock in me. His hand was such a blur under water and I could feel my cum boiling in my balls. I was literally grasping for air since his left hand had pinned my head on the ground. 

Moaning, I told him I was near. I felt him fuck me faster hitting hard on my prostate. (I think) 

“Ahh…ahh….aa…I’m gonna cum, Dwain.” He said as I was about to come. He jerked me off frantically which triggered my own cum to spurt out of my spent cock. 

“AHHH…Ohhhh…aahhhh…” was all I could say.

“Here it goes! Ahhhhhhhhhhhhhhhh!!!!!!!!!!!!!!” Will screamed as he pump his seed in me. 

I could still feel his rock hard cock in my hole even though he’d cum. Still inside me, he kissed me again and licked my ears. 

Out of breath, he asked, “Fancy another game, Dwain…?” 

I couldn’t be bothered to talk; I felt so spent and exhausted.

“…only this time, the loser takes it all in…” He forced his tongue in me again and we kissed. He broke off and continued, “…in his mouth.”