Straight Man Wins Gay Boy in Poker Game [MM]

Straight Man Wins Gay Boy in Poker Game

I was invited to play high stakes poker. It was all middle aged or older men who had made fortunes. Some of them were in businesses that were barely legal. Legal or not I would never admit knowing. They would get together for poker once a month. I had been somewhat successful over the last few years and someone had noticed. I was a little surprised when I received an invitation. I was not even close to their level of wealth. However, it was an opportunity for me to mix with them. I had been invited by a business associate, Tom Hallan. He had several businesses, real estate property and he was a lawyer. Tom had reassured me that everyone could only bet a maximum of one hundred thousand. He did say that we could raise the stakes but that it would have to be unanimous. If I lost it all, it would hurt me but I could handle it. These guys had been known to make million dollar deals in minutes.

Tom introduced the other four to me. Vito Manucho, Caspar Edvin, and Chad Garrison. Tom did not tell me what business they were in and I knew not to ask. There were three twenty-something women with large breasts who appeared to be there for decoration. They wore very little and were only there to smile and serve drinks if asked. Then there were two very feminine boys, around the same age. I guessed they were also there as eye candy. That was not my style.

We got to playing and it was very even for a while. The girls and boys served us drinks and snacks. The men would blatantly grope them and the servers didn’t seem to mind. They encouraged me to do the same. “You can touch all you want,” they said. “They expect it.” But I wasn’t into that. As the night progressed, I got the upper hand and it got to the point where I would win it all. Chad had was the only one remaining that had close to enough funds to match me. It was obvious that he would need more. I wasn’t up to raising the stakes. Chad called for a pause. Someone proposed raising the stakes. This meant that Chad would be allowed to bring in his vast fortune and simply outbid me. That got shut down right away. Everyone felt that Chad could be allowed to have one more chance. It was to be a double or nothing. So there I was, one last play, win it all or lose it all. I was hesitant and they sensed it. The Chad proposed that I could have his boy for the night if I wanted. I wasn’t gay so having his boy meant nothing to me. But I got the sense that I should accept. If I won I would take all the money and I would get his boy that I didn’t care for. If I lost this last one, I would walk away with losing one hundred grand which I was fine with losing when I walked in the door. “Let’s do it,” I said. Well, it came down to one card. Breaths were held. When the final card was flipped I had won. Emotions were varied. Chad was disappointed of course. The others were smiling. Chad motioned to the boy. He walked over to me. He tended to keep his eyes downward. He was a skinny lad, short and very white skinned. “Shall we go?” he said.

When I got him back to my room, I asked him about himself. I got the impression that he wasn’t really being truthful. Perhaps he was trying to tell me what I wanted to hear.

“You need to know you are in charge,” he offered looking up at me trying to be coy. “You can do anything you want.”

I had to be direct. “You can just spend the night,” I said. “Nothing is going to happen. I’m not into men.”

That seemed to disappoint him. His demeanor changed. He looked at me.

“Look at this body,” he said. “I’m not sure I should be referred to as a man.”

I thought about that and I had no answer.

“You have to use me,” he continued. “Think about it. You win a prize then don’t claim it? You’re sending the message that what he offered has no value. You will look weak and it will be an insult.”

“So. Just lie,” I retorted. “Just tell him I fucked you.”

“He didn’t get to where he is by being stupid. He is a master at human nature. He will know. Then I will be in serious trouble. I can’t lie. Not about this!”

I could hear a whimper in his voice. I could see tears forming in his eyes.

“No,” he continued. “You have to take me. You must. And you have to fuck me like I have never been fucked before. Maybe you aren’t into guys. But tonight, you have to be into me. He must believe that you had the experience of your life. Or the blame will fall on me.”

He put his hand on my chest but I pushed it away. He ignored my gesture and put it back and started to rub my chest, looking up at me. This time I let him do it. My arms were at my side. He took one of my hands and and placed it firmly on his ass. I squeezed it a little and he let out a little moan like a girl. I had never ever been with a penis carrying creature. I had never intended to. I placed my other hand on his other cheek. He moaned again. “That’s more like it,” he muttered.

I pulled him closer and his lips approached mine. Maybe it was the alcohol. I had never considered, not even remotely, that I would ever have sex with another male. But here I was. I leaned down and tried to kiss him.

“You don’t have to kiss me,” he said.

“You said I was in charge.”

“You are.”

“Then shut the fuck up.”

That seemed to light a fire. Because he came at me with intensity. He had his hands on my neck. Then he locked onto my mouth like an industrial strength suction. He reached down and started to grope my package. He could not wait to touch my cock. I pulled off his shirt. He had a nice body for a boy. It was smooth and very feminine. His nipples were pink. I touched his nipple and he jumped. “They’re really sensitive,” he muttered. All I know is that when I have sex, there are nipples involved. And this time it won’t be any different. I pinched them gently which caused him to squirm. He undid the buttons to my shirt which I helped him remove. He ran his hands over my stomach and chest almost drooling. Then he knelt down and started to undo my pants. He popped out my cock. “Oh fuck,” he said. “This is huge!” He started sucking and licking the head. For someone who was supposedly gay and had experience sucking cock, he was unable to take it all. “I thought you gay guys could deep throat,” I said. He got the sarcasm.

“Not when they are this big,” he replied.

“Well, you want me to have the time of my life you better figure out how to get that down your little throat.”

The one thing he had was enthusiasm. And he gave it a go. As much as he tried, he could not get it down his throat. I had an idea. I got him on the bed with his head off the end of the bed. That way the throat lined up directly. I entered his mouth and started to pump. Then I pressed and forced it down his throat. It popped. He struggled a little, trying to push me off but I was way stronger than him. I only held it there for 5 seconds then pulled out.

He was breathing deeply. “Fuck!” said. “I’m sorry.”

“Don’t worry,” I said. “We are only just starting. Next time, do not try to push me off.”

I hope I said that with a stern enough voice.

I entered his mouth again and pushed on. I felt him tense as I started entering his throat. I pushed in and he was better this time. He was obviously struggling with my cock deep in his throat. I held it for three to five seconds then pulled out. Then I did it again until I was entering and pulling out at will. “Good boy,” I said. “You can do it.”

I pinched his nipples as my cock slowly tunneled down his throat. He was gagging off and on but I could tell he was really trying. Then I stopped to get him fully naked. He was completely smooth as I thought he might be. He had the a tiny uncut penis which I actually thought was cute. I got between his legs ready to give it a few licks. When he realized what I was about to do, he got all tense. “You don’t have to do that,” he protested.

“Who is in charge?” I asked.

“You.”

“Then shut the fuck up and let me do what I want to do,” I said. “Isn’t that how this works?”

He was erect and it must have been three inches. Even erect, the foreskin remained forward, covering the glans. I held it with my thumb and a finger stroking it as best as I could. I tried to pull the foreskin back and it peeled back with some difficulty. The tiny glans was purple and shiny. I licked it a few times and he squirmed. I have to admit that I was enjoying it. I licked his tiny balls. He really seemed to like that. Usually, when I had sex with women, I licked their pussy. How could I do that here? I pushed his legs up and his ass opened up to present a stunning pink hole. Damn, I thought. I want to fuck that. But it looks impossibly tight. I applied my tongue to it and he moaned loudly. “Oh fuck!” he said loudly.

“You like that tongue slut?” I asked.

“Yes,” he said. “I love your tongue. Tongue me deep.”

I went crazy tongue fucking him. I never understood how someone could fuck a dude. At least I had an idea now. As my tongue did its magic I could feel his hole opening and relaxing. The I positioned myself to get into him.

“No wait,” he said. “Lube me.”

He pointed to his bag. There was a tube in his bag. I put some on my cock and his hole. Then I pressed my cock to his pink center. I pushed and he resisted. Never mind, I just kept the pressure on his tight sphincter. I moved back and forth a little and I could feel it giving. “Fuck,” he screamed. I could not tell if he was enjoying it or in pain. That didn’t seem important.

I felt my cock pop in. It was the tightest grip I had ever experienced. It took a while, but slowly, I pushed deeper and started to pull out and push in. We were doing it. I fucked him steadily until he loosened up a bit more.

He moaned uncontrollably. “Your cock feels so good in me,” he said.

I fucked him deeper and longer. It was tight but I was drilling into him at will.

I fucked him even faster and harder. To my surprise he suddenly uttered “I’m cumming” then he squirted on himself. It wasn’t much liquid. His body shuddered but I continued to plunge into him. I was a long way from orgasm. It was going to be one of those times where I take a very long time to cum. I must have fucked him for another thirty minutes before I pumped my load into him. When I pulled out, his ass was open like a fucking cave. He put his fingers into it feeling around in the gaping cum filled hole. I moved his hand away. I wanted to see my handiwork. The muscles contracted somewhat but it was still very open.

He popped off the bed and got a towel which he used to clean me before cleaning himself.

He looked uneasy. “What happens now?” he asked. “You want me to leave?”

“What?” I shot back. “I have you for the night. You aren’t going anywhere.”

I wasn’t kidding. He was right. I had to use him to the max.

That seemed to make him happy although there was something he wasn’t telling me.

I turned off most of the lights, leaving on a small lamp so the room was dimply lit. “Sleep in the bed with me,” I said.

He smiled as he got under the covers, seemingly contented.

I dozed off. I woke up about two hours later. I reached over and he was still there. I rolled over behind him placing my hand on his ass. I started to squeeze it. He stirred. My cock was hard. It knew what it wanted. I didn’t like that he had put his underwear on. It was getting in my way. I pulled them down enough so that his ass was out. I squeezed and rubbed then slid my hand towards his entrance. I was surprised when I found it to be a little wet and my finger entered easily. This little schemer was expecting me. Well, no matter. I fingered him and I heard him moan. This wasn’t going to be fancy. Just get it in and fuck until I had enough. I put my cock to the gate. It was not as tight as it was the first time because of the earlier activity. I pushed a little and I felt him push back at me. Again a moan. This time it was more of a casual fuck. I relaxed and slid into him repeatedly. It took a while and I eventually shot my load into him. I stay on top of him for a few minutes then rolled off and fell asleep. Around 5:30 he woke me.

“I need to go soon,” he whispered.

I could sense something; disappointment, fear, anxiety. He didn’t seem to be the type to really show such emotions.

“What’s up with you?” I asked.

He hesitated. “Nothing really.”

“Let’s not waste time,” I replied.

He sighed. “It was too good. The sex. I am not going to be able to hide it. Garrison gave me to you as a poisoned gift. You weren’t supposed to like it. He paid you with something that was supposed to have little value to you. It was like paying his bill with play money just for spite. What made it even worse was that I enjoyed it too much. Garrison never made me feel like that or cum like that. It’s a challenge to his manhood. This will not go well.”

I wasn’t sure what to say. What he said made sense.

“What are you going to do?”

“I have been with him for three years. No one has ever lasted that long. It’s because I make him think that I don’t like it. It makes him feel powerful that he can force someone to do something they don’t want to do. So I have to pretend I don’t want it. But I also have to be enthusiastic. So I have to act as if I like it while at the same time convincing him that I don’t like it and that he is forcing me. I am going to play the same game. If someone held you down and jerked you off, you might not like it but you will likely still cum. So you can enjoy it and not like it at the same time.”

I was shocked that this kid had such insight.

“You think it will work?”

“Yes,” he replied.

He played an interesting but dangerous game. I wondered what his long term plan was to get out.

He got dressed and left.

I was fully awake. I laid there thinking about what had just happened. I willingly had sex with a guy and it wasn’t bad. It wasn’t that I was suddenly gay. Far from it. However, the door was opened and it would always be open just a little bit in the future.

Source: reddit.com/r/eroticliterature/comments/uta0y2/straight_man_wins_gay_boy_in_poker_game_mm