A gay story: Check Mate Jim was one of the first men I met when we came to live here in Asia 7 years ago. We had not found the right place to build our house yet, so we stayed in a guest house. On one of the first days, the owner introduced us to Jim, an English man, a little older than me, who had been living for over twenty years in what would become our hometown. We turned out to have the same interests, like in music and art, and both were not that interested in small talk. Out of the blue, Jim asked if I could play chess. I said I could, but hadn’t played in over 15 years.
“How about next Tuesday morning?” he asked.
“Why not… I’ll be there,” I replied.
That was the start of 6 years of weekly chess mornings on Tuesdays. And it was more than just chess. We discussed anything and everything. Sometimes an hour had already passed and we had only made our opening moves. Another time we were mostly silent and played 5 or 6 games.
Jim clearly played better than me. I was never completely out of luck, but he won 3 out of 4 games. And I suspected that he sometimes let me win that one game on purpose. After about 6 years of playing, he hinted that he was getting a bit bored. We switched to Cappablanca Chess for a while, a variant with 2 extra pieces. But Jim seemed to have had enough anyway.
One day we had left the chess pieces in the box and were chatting and joking and philosophizing how we could make chess more exciting.
“I have an idea,” I said with a mischievous grin, “but we can’t execute it here.”
“You make me curious, tell me,” Jim replied.
“No,” I laughed, “I should have kept my mouth shut. It’s really a silly joke.”
“Then I want to know for sure now”, was Jim’s reply.
“Okay, okay, I was thinking about a variant of strip poker, where you can buy back lost pieces by taking off a piece of clothing. Strip chess so to speak.”
Jim nearly fell off his chair laughing. “Have you thought about the rules yet?”
“Unlike strip poker, it shouldn’t be about getting the other person’s clothes off as quickly as possible. It should remain chess, so the goal is still to capture the other person’s king. But that has been captured can be bought back again. A shoe or sock for a pawn, a shirt for a knight or bishop, trousers for a rook and underpants for the queen.”
Jim thought about it for a moment and then asked, “What if you want to buy back your queen, but you still have your pants on?”
“I have also thought about that. In that situation you will have to take off your pants too. If you already lost a rook, you will get it back. Otherwise you are out of luck and it will be a very expensive queen.”
“Okay,” said Jim, standing up. “Come over to my place. Let’s play it.”
I never expected him to react like that. All things considered, it was just a bad joke on my part. But at the same time I found it exciting. So fifteen minutes later we were sitting at the table in his living room and Jim set up the Cappablanca chessboard.
I looked a little surprised. “For Cappablanca additional rules are needed”.
“I came up with something for that along the way,” he said. “We keep the rules the same for most pieces, except now you use your underpants to buy back the chancellor or the archbishop (the extra pieces of Cappablanca). If you want your queen back, you pay with a blowjob. And we left our shoes outside, so we can buy back a maximum of 2 pawns.”
I didn’t know what to say. Was he serious about the price of a queen? He knew as well as I did that the best chance was that I would end up having to give that blowjob. But he also knew that the chances that he would have to give me one were definitely not zero. Unless, of course, he intended to renounce his queen, if I had captured it.
“I can see you’re surprised at my proposal,” said Jim. “But I have to admit that your idea turns me on insanely. You know, I haven’t felt a hand other than mine on my cock in months. From the moment you started talking about strip chess, I knew that’s what I wanted to do.”
The game took its usual course. In the beginning it went pretty well. We traded a few pawns. I sacrificed a bishop for a horse, which is always one of his key weapons. And in typical fashion, I was so focused on beating his archbishop that I didn’t see him slowly mounting an attack. He let me take his archbishop, but promptly put me in check.
The only way I could avoid checkmate was to put my chancellor in front of the king. Jim hit him with his queen, putting me back in check. Now the only option for me was to protect my king with my queen. After Jim had captured that one too, I was able to move my king to where my queen had previously been, removing the threat to my king. But by moving my king, a rook was no longer covered, so I lost that piece as well.
It became clear that I had to do something now in order not to lose the game very soon.
Now I have to tell you that for me one of the biggest turn offs during sex is a man who keeps his socks on. From a chess point of view it was absolutely unwise what I did, but in the prospect of ending up completely naked I couldn’t avoid my next step:
“I want to buy back 2 pawns,” I said, taking off my socks.
“Why that?” wondered Jim. I told him that I would explain it later.
It soon became clear how unwise it was to let my cock dictate my choices instead of my mind. When replacing the pawns, I paid too much attention to the possibility of earning back my queen “for free.” Jim immediately punished that by capturing my archbishop as well. Now I had lost my 2 valuable cappablanca pieces, my queen, a bishop and a rook, while he only lost 1 cappablanca piece in addition to some pawns and a knight.
I moved one of my pawns forward, trying to reach the last row, where it would turn into a queen. But Jim saw through and positioned his chancellor to cut off the road. The only way to protect my pawn was to put my “white” bishop in the right place. But I no longer had it.
I took off my shirt. “I’m buying back my bishop.”
Jim’s reaction was about the last thing I expected. He took off 1 sock and put his bought back pawn on the space in front of mine, blocking the way to the last row for my pawn. Of course I again didn’t think enough and immediately attacked the new pawn with a rook. Jim paid no heed, but positioned his queen to threaten both my newly repurchased chancellor and my king. I was one move away from checkmate.
My only way out was a move that could avoid checkmate for me and at the same time would attack Jim’s king. And there was only one piece that could do that.
“I need my archbishop.” I handed over my pants and undies to Jim and was completely naked now.
Once again Jim had a simple but effective response. He exchanged his other sock for a pawn and placed it so that it threatened my archbishop. But if I would move my archbishop he could capture my king and it would be game over. So I had to use my last resort.
I got up and pushed the table aside. I walked over to Jim, who still had all his clothes on except for his socks. As my cock slowly grew in small jerks, showing that I didn’t mind what was happening at all, I dropped to my knees. I unzipped Jim’s pants and belt and unbuttoned his pants. My hand disappeared into his underpants and pulled out an almost completely hard cock.
Jim moaned softly as I grabbed his cock. “Ooohhhh, I’ve missed this feeling for so long, mmmmm.”
I played a bit with the now rock hard pole. Jim seemed to lose all control. He moaned and squirmed, nearly slipped off his chair, and finally grabbed my head and pulled it toward his cock. It was obvious that he hadn’t experienced this in a long time and could explode at any moment.
With my tongue I licked the skin just behind his head. Then I increased the tension of my lips and pushed forward with force, so that his entire cock disappeared in my mouth. I relaxed my lips a little as I moved my head back again. When only his head was left in my mouth I tightened my lips again and pushed forward forcefully. His balls bugged against my chin, his cock head crashing deep into my throat.
As I repeated those movements, his moans grew louder. He gripped my head tightly, and began to jerk more and more wildly, finally seeming to freeze, then, with a loud scream, squirted a large jet of cum down my throat. A second shot followed quickly. I couldn’t keep my mouth on his cock because of all that cum, but had to let it slip out. Immediately a third wave of cum came, which I was just able to catch in my mouth. Two smaller waves ended in my beard.
After Jim came to his senses he stared at me blankly. “Wow, that was the most heavenly blowjob I’ve ever had,” he moaned. “Where did you leave my juices? My clothes are still completely clean.”
I smiled. “I had to catch everything, otherwise you would get stains in your clothes.” As I said that, Jim’s cum gushed out of my mouth, dripping through my beard onto my chest. In slow trickles it seeped down into my pubic hair. A trickle continued down my semi-erect cock and dripped from my cockhead to the floor.
“So now tell me, why you bought back those pawns first?” I laughed and told him of my resistance to men wearing only socks. He had a good laugh too then.
I got up and pushed the table back into place. I took my repurchased queen and put it in the place I had already planned.
“Checkmate!”
An unforgettable game that we both won.
(Thanks to Literotica members Nudeinthewild and A13579 for their comments and editing)