Checkers with a Gorgeous TS

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How I became hooked on checkers.
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This story is part fiction AND part true. Any resemblance to anyone in the story to anyone in real life is just coincidence. It is about black domination and gay oral sex. If it is not to your liking do not read it.

Growing up most of us have played the board game of checkers. Ever since I was a little boy of about ten years of age I became involved with it and enjoyed beating my opponents. Later on in life, however, as I grew older I enjoyed even more so losing the games especially if my opponent was a female.

At about the age of twelve I entered a checkers tournament at the local elementary school playground where there were organized activities run by young adults to give the kids something to do while there was no school during the summer. Those same activities were at the other seven elementary schools throughout the town. The way the whole thing was set up was the winners in the different age groups at each playground were taken to a central park in town to compete against the winners from the other playgrounds. For me it was a great joy to be allowed to go on a car trip with someone other than my dad, and of course I was proud to go as the winner of my local playground.

Going into the grand tournament I was very confident and knew for sure I would have no problem winning first place, just like I did at my own playground where I had no trouble at all beating the others. And all went very well up until the championship game, which was a best-of-three series. I was very surprised and humbled when I lost two in a row to my opponent who was a cute little GIRL! So I had to settle for the second place trophy, which was about half the size of the winner's trophy, and of course my playground leader tried to console me on the way home but I was crunched and humbled. A GIRL?? How in the world could I let that happen? In reality I didn't let it happen because she simply beat the snot of me! During both games when she knew she had the game won she would have the cutest smile on her pretty face, and although at the time I wasn't happy about losing I believe that's where it began with me liking the idea of losing to a female.

As I grew older and into my middle age years the interest for the game of checkers faded away. I had other things to do until one day as I was on a search engine on the internet I noticed several places that offered 'free online checkers'. I thought to myself how cool could that be if I could actually compete again in a game that I hadn't played for a long time. I didn't want to play against a computer and I was happy to see an invitation to actually play against other people!

So I registered on a site under the name 'sub-mate' since I was feeling somewhat horny and submissive at the time. And sure enough as advertised there were hundreds of people from all over the world playing checkers online.

My first opponent was listed as 'guest', which was an option for anyone who didn't want to register. After a pretty even match he or she beat me and I had a lot fun playing. I was hooked! Then I thought to myself that I would like to play against women so if I lost I wouldn't feel so bad, unlike when I was much younger and that cute little girl beat the pants off me in that playground tourney. I had grown to love Femdom especially if she had great legs, and losing to a woman, whether she's Femdom or not, would be an excitement for me. Of course it was a fantasy since I had no way of knowing if my opponent was a woman or a man whenever I played online. I could only guess by the username if it seemed to be female. For example, if the username was 'melissa' or 'maryann' I figured they were female.

There were many people ready to play whenever I went on the site so I would always pick out a name that at least seemed to be a female. And if I was wrong and the opponent was male, so what? I would then just play on and fantasize that HE beat me and sometimes pretend that I had to suck his cock as a 'penalty'. It also was a submissive thing for me because I had never even been close to another man's dick.

Playing checkers online became almost an addiction to me, sort of like the many people who can't go anywhere without their cell phones 'stuck' to their ears. It was very hard for me NOT to jump on that checkers site when I had spare time. It got to the point where I was ALWAYS looking for spare time so I could play.

One day as I was on the site ready to play looking for an opponent I noticed a name that read 'Tina-T'. I wanted to play against that one because I was sure 'Tina-T' was a woman. So I challenged her to a game and she accepted. I was planning to take it easy and not try hard to win to make sure SHE won, which was how I approached all those games because it was more exciting to lose than to win, at least for me when I was in a horny submissive mood.

By the time that first game with Tina-T was over I realized that I didn't have to LET her win at all! If you know how the game of checkers goes it's always best if you can get kings because you can then move them in any direction you want instead of just forward as it is with the regular pieces. I was unable to get even one king while Tina-T jumped me so many times she wound up with seven kings and three regular checkers. That means that I only was able to jump TWO of her pieces.

After that whipping a box popped up on the screen and said I lost, as if I didn't already know that. Another box popped up and said my challenger requested a rematch. I was stunned at first but I accepted the challenge and we began another game. Tina-T seemed much better than me and I was surprised that she wanted to waste time playing me.

The game was closer than the first one but Tina-T ended up trapping all four of my remaining men in a corner where I didn't have a move and I had to concede. It was similar to being tied up where you are completely immobile with no way to escape. When the box appeared that told me I lost I again I hit the OK button and waited for Tina-T to issue another challenge. But she surprised me and left the game. I played Tina-T many times later and it always wound up the same way with her winning easily. I played her so many times it seemed like I knew her personally. I played her perhaps 15 times and never won one game. But that was fine because of my fantasy and my 5 inch dick (erect) got hard thinking about her.

The checkers site also had an option where the players could chat with each other while they played. Tina-T and I chatted often and that made the games much more fun. She enjoyed rubbing it in when she won and I enjoyed reading her messages. Playing checkers became much more fun whenever we played against each other.

Yesterday I was playing against another young lady who I believe was from the Netherlands. There was a picture of her next to her name and if it was truly her she was a gorgeous young blond. We played three games and even though they were close she won all of them. I was learning how to lose and to my surprise it wasn't so bad. All my life, other than the checkers games, I hated to lose and sometimes it would make me very upset. But I've matured a lot and now don't mind losing at all.

*******

One Saturday evening shortly after dinner I was sitting on the sofa in the living room playing online checkers on my laptop. My wife had gone away for a few weeks to visit her mother in another state and I was alone. I had just started a game when the doorbell rang. I quickly exited off the site to answer the door.

Standing at the door was a beautiful brown haired woman of about 35 years of age and who stood about 5'7" tall. She was wearing a short flowered sundress with a hem that stopped just above her knees. I was able to sneak a quick glance at her legs and I was impressed. This young lady was gorgeous.

"Good evening. May I help you?" I politely asked.

"Sure," she said, "I am looking for 'sub-mate."

"Sub-mate?" I asked. I didn't know what she meant so I asked her to repeat what she said.

"Yes, sub-mate. I'm Tina-T on the checkers site," she nonchalantly said. "Are you going to invite me in?"

She was not only beautiful but very pleasant. I was stunned!

"Oh, sorry. Please pardon my manners. Come right in. How did you ever find me?" I asked.

"It wasn't hard, no pun intended. I just searched under your name and your information came up," she said.

"How did you get my name?" I asked her.

"All I did was go to your profile on the checkers site. One thing led to another and I was able to find your address and other things about you too. Is your wife Debbie at home? I would love to meet her too," Tina said.

"No, she's away for awhile to see her ill mother. So it's just me for now," I told her. "And how do you know her name?"

"Because it's part of your files. Anyway, I didn't come here to discuss your history. I came here to play some checkers with you in person. Are you interested?" she asked.

"Well, I wasn't exactly planning that tonight but since you made the effort to come here to my house, sure, I'm ready. I would love to play you. I have a checkerboard right here in the closet," I replied. I went to the closet and got the game out and put it on the coffee table in the living room. "Tina, this is a huge surprise. I didn't know there are women on that game site so pretty as you."

"That's very flattering, Robert. Thank you," she said. "But before we play would you like to put any wagers on the game, you know, just to make it more fun?"

"This is a big surprise, you showing up at my door, so I hadn't even thought about anything like that. What do you have in mind?"

"Well, how about this: if you win I will suck your dick, but if I win you go down on me?"

"Okay," I said cautiously, "anything else?" I asked her. "I mean, we just met and already we're going along so fast. But it does sound like fun."

"Okay, how about this. You tie me up if you win, then you can do whatever you want," Tina said. "But if I win I get to tie you up. Sound fair?"

"It isn't too likely that YOU will lose. You have already beaten me 15 times in a row," I said to her. "But, you know, Tina, I'm feeling kind of horny and you look very sexy. Let's do it!" I exclaimed.

"Great!" she said and we set up the checkerboard in the living room. "You go first since I beat the pants off you when we played online. But first we each must tie one wrist to the chair in case someone wants to back out in the end." So we each tied a piece of rope to the chair we were on then made a loop with the opposite end. We then slipped a wrist into the loop and pulled it tight to fasten it. I tied my right hand and she Tina tied her left hand.

"You don't have to rub it in!" I replied. "But if I'm going to lose I would rather it be to someone so pretty as you." As she sat there next to me I couldn't help but to sneak several glances at her great legs as her dress's hem sneaked up a few inches. Wow, I thought, they are gorgeous!

"You like what you see?" Tina teased.

"I didn't think you noticed. But, yes, you have very pretty legs!" I said.

I was determined to beat her this time and not be so submissive. But after about five moves by both of us I could see her plan developing and it didn't look good for me. She had taken most of my pieces and had the others trapped in corners. Five minutes later I was through as she jumped my last piece. She still had eight of her twelve checkers on the board and I was once again whipped.

She quickly reached behind her chair and loosened the rope to set her hand free. She then got up from her chair and came to me and easily tied my left wrist behind my chair. She also tied my ankles to the legs of the chair to complete my capture. Well, I thought, at least I was going to lick some pussy.

Tina then held my head still and kissed me deeply on my lips. I couldn't have turned away even if I wanted to. But why would I?

"Well, well, look what we have here!" she said. "Have you ever sucked cock, Robert, because you are about to suck mine," she continued as she began removing her dress and panties.

"Wait a minute!" I shouted. "I thought you were a woman! You didn't tell me you're a guy." I struggled to get free but it was no use. She had me tied pretty tight.

"I also didn't tell you I am a WOMAN!" she replied calmly. "I'm a transgender and I LOVE being in control. So open your mouth and pay your debt."

When I tried to keep my mouth closed Tina put her thumb and forefinger on both sides of my cheeks and squeezed. It hurt a lot and I was forced to open my mouth, and when I did she slipped her gorgeous 8 inch cock in. I had never had another man's dick in my mouth before and I was really surprised how pleasant it felt.

Sitting on a chair with my hands tied behind my back prevented me from stopping her and she gently slid her cock in and out of my mouth. The texture of her smooth penis was like nothing I had ever felt before, and I was very surprised of the sweet taste. Then I began to wonder what her cum tasted like because I was sure I was going to find out soon. She continued fucking my face, sliding her big dick in and out of my mouth, and I was powerless to do anything about it as she held my head still. It was sooo erotic and I could feel my cock getting stiff.

Soon Tina tensed up and I knew she was about to empty her load in me. She moaned a bit and her baby juice shot into my mouth and for the first time in my life I tasted another person's cum. Yummy! It was kind of sweet but also a little tangy. It was fabulous! When she was finished filling my mouth and after I swallowed all of it, Tina sat on my lap with her sexy thighs resting on me and kissed me on my cheeks and said, "How was it?"

"That was great!" I said to her. "That was the first time I ever had a dick in my mouth and the first time I ever tasted another's cum. I loved the texture of your smooth cock and I want more of that tasty cum."

"Your mouth was made just for my cock!" she said as she reached behind me and started to untie my hands.

"And I can see you're excited by it. But I'm not going to relieve you of your stress," she said as she gently touched my shorts and my swollen cock..

"You don't have to untie me just yet, you know," I said to her.

"Oh, I see," she replied. "You like it the way it is. That's good, I will just leave you like this for awhile. That way if I get in the mood again I can easily make you open your mouth and feed you."

"You won't have to force my mouth open," I said.

"So you really liked that, did you?" she teasingly asked.

"Absolutely!" I replied. "You know, we have at least three weeks until my wife gets home. Would you like to stay here until then?"

"Sure! That's a GREAT idea," she said. "But that's going to be a lot of cum to eat!"

"As long as you can produce it I can enjoy it," I said as my eyes couldn't stay off her magnificent legs. "Did anyone ever tell you that you have great legs?"

"Of course they did!" Tina replied. "I pride myself in my beautiful smooth legs."

Tina and I enjoyed oral sex almost every night for a few weeks, but the time was getting close that my wife Debbie would be getting back from her mother's.

"Tina," I said one evening, "my wife Debbie will be getting back this Friday afternoon. What are we going to do about all this cock sucking and cum eating?"

Tina very calmly asked me, "Does she play checkers?"

It made me laugh when she said that and I replied to her, "Why? What do you have in mind, you devious sexy thing?"

"If she doesn't play then I am the perfect one to teach her. Wouldn't you agree?" Tina said.

"Oh, boy," I chimed in, "this is going to get very interesting."

(to be continued)

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vietnamvetvietnamvetover 3 years agoAuthor
Maybe?

But if his wife was off running to her mom for a month, and how do we know how often that happened, maybe, just maybe, he was out looking. Besides, it all happened so fast and with his love for checkers he was vulnerable.

TheKrrakTheKrrakover 3 years ago

He really quickly agreed to cheat on his wife, must not be much of a marriage...

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