It all started one day when I was invited to my best friend Dave’s house for a house warming party. He had just purchased the house after a harsh divorce and he wanted to break it in the right way. So, he invited a few friends who in turn invited friends.
It turned out to be a bigger party than what he was expecting. The more the merrier was all he could say. There were at least 60 people in all running throughout his house, in the back at the pool and it even spilled over into the front yard. It was not a rowdy party, so there were no police called. Thank goodness for that.
Anyway, Dave and I were like brothers, we grew up together and always watched each other’s back. As the day wore on, the party slowly started to break up; it was about 10 or 11 that night. There were around 10 people left and Dave made the suggestion that he take everyone out to the local bar. This was only due to the alcohol having run out. He said that he was buying.
Everyone was up for that, with the exception of Tyssa and me. We had a game of pool going and we really did not want to stop. So, I approached Dave and said that I would like to stay and finish our game of pool. Of course he had no problem with that and he tossed me the keys and said for me to meet him at the bar once we had finished.
Now, I am not what I consider to be a good looking man. I am 5’8” tall, slight belly but still fit. I have greying hair, mustache and beard. I am somewhat fit for my body type. I didn’t like to work out, but I tried to make up for that with daily walks and hikes.
I had met Tyssa while walking through the house introducing myself to people I did not know and saying “Hi” to those I did know. Tyssa was sitting outside on the patio. Tyssa was a beautiful lady. She stood about 5’9” tall, with long sandy blonde hair, pert double D breasts and very sexy legs. She was wearing a jean mini skirt, which showed off her legs very well. She had on a black lacy top in which one could see her breasts. She did not seem too embarrassed to have worn such a revealing top. She was also wearing black nylons and shoes to match her outfit.
I approached her and we introduced ourselves. I then asked her how things were going for her today. She said that she was just waiting for her turn to play a game of pool. We talked with each other until she was called to take her spot at the table. I followed her inside and I sat back and watched her play her game. They were playing winner keeps the table. Well, I decided to put my name in the pot for my turn at playing.
Tyssa was a very good player; she had beaten everyone who had come up against her. Finally it was my turn to play against her, the party had been breaking up slowly up until the time I finally got my chance to play. I approached the table and racked the balls. As the game got started, that was when Dave had called out for a party at the bar.
I looked over to Tyssa and asked, “Would you like to join us and go to the bar? It’s not very often Dave offers to buy.”
“No, I am not much of a crowd person. I guess I will just head on home,” she replied.
I didn’t want her to leave because she was the only one who wanted to carry on a conversation with me. “Would you rather just hang out here and play some pool?” I asked.
She looked over at me and asked, “What about your friend? This is his house, isn’t it?”
“Yes, it is but we are like brothers, he will not mind if we stay behind for a few games,” I replied. “Hey, Dave is it all right if Tyssa and I stay here and play a few games? She's not much into crowds and we are just getting started.”
He tossed me the keys and replied, “Sure. Here are the keys lock up and meet me at the bar when you're done.”
I turned back to Tyssa and smiled. “See, I told you he wouldn’t mind. Shall we begin? Let’s say best of five for starters.”
“You’re on!” she replied. She lined up for the breaking shot and the game was on.
I was really beginning to enjoy just being alone with her as we played. We talked as the games wore on. I ended up beating her 3 games to 1. I was starting to put away my cue when she asked, “What would you to say to 5 more games but we make it a little more interesting?”
“What do you have in mind as the stakes? How about 10 a game?” I asked.
“I was thinking something more along the lines of, if I win, you do what I tell you to do. If you win, I do what you tell me to do. Nothing is off limits. Sound interesting enough to you?” she finished off.
She definitely caught me off guard with that one. I stood there for a minute and thought about it. I was always told that if someone made a bet with you that it ended up being a sucker bet. I figured what the hell. I would be willing to do what she would want me to do, but I really had to make a stipulation. “I can go for that, but there has to be one rule to this. We do not make the other do anything that could get them hurt or thrown in jail.”
“I figured it would just pertain to the confounds of this room and nowhere else,” she said.
“Then you have yourself a deal. Best of 5 games and winner controls the other. I guess I will break, I was the winner of the last 5.”
I watched as her demeanor changed into a more serious player. I thought to myself that I was in for the games of my life, so to speak. I broke and started off real well. I had a run of the table going, which was up until she came up behind me and blew into my ear. I scratched.
“So, that is how the games will be played then, huh?” I asked as a sly grin crossed my face.
“Do your best, I think I can handle you and what you can dish out,” she said as she smiled back at me.
“Does anything go here as well? I mean, in short of hitting their cue or arm in order to make them miss,” I added.
“I’ll agree with that. Shall we begin the run of the gauntlet?”
It was her turn and I moved in behind her, but before I could do anything, she pulled back and poked me in the stomach with her cue. I laughed and told her that I wasn’t expecting that one and that she shouldn’t do it again.
She lined up for the next shot and I hurried over and grabbed her ass just as she was shooting. Her ass was so firm in my hand that I got an instant erection. I had never played a game of pool in this way before and it was really turning me on, especially knowing that anything goes while playing. Anyway, she didn’t miss. She was just as steady as if I hadn’t done a thing. I knew I was in for one hell of a game. She beat me badly, I never stood a chance.
We played the last of the games and as we did it turned more and more into a very touchy-feely game. She had grabbed my ass, played with my cock and balls (I know that she had felt the stiffness in my jeans when she had done that), kissed my neck and she had even exposed her breasts to me while shooting.
Needless to say, I had my ass handed to me in more ways than one. I laid my cue on the table and looked over to her. “Well, it was a sucker bet and I lost to you, fair and square. I am yours to command,” I said.
She just stood there and said nothing. I walked over to her and as I did she lowered her head. I asked her what was wrong.
“I don’t think I can go through with this, I have deceived you and I do not think it fair. If you truly knew the truth about me, I really doubt you would have made this bet with me,” she said.
“I don’t understand. We were both in agreement before these games ever began. I knew what I was getting into when I made the bet,” I stated.
“No, you really didn’t know what you were getting into. I am not like any girl you may have been with. I am different,” she commented.
“Now I am lost. You were so excited to play and now it comes down to claiming your winnings, you are backing down.”
She slowly began to unzip her skirt, but she would not look up at me. “Here, I will show you. I just hope that I do not get hurt once you see what I am talking about.”
After unzipping her skirt, she bent down to remove it. It wasn’t until she stood up that I noticed the bulge she was so desperately trying to hide. I just stood there in a state of shock, not knowing what to say but at the same time I was really getting turned on. I never thought of myself as being gay in any way, but seeing her in this way was making me rethink my life.
I walked over to her and I lifted her head up so that she was looking into my eyes. I didn’t know what came over me, but I leaned in and began to kiss her on her mouth. She was a little resistant but slowly relaxed and allowed my tongue to penetrate her mouth.
We kissed passionately and I slowly began to run my hands down her waist and back to her nice firm ass. I pulled her into me and I felt our cocks start to rub against each other through our clothing. I was harder than I could ever remember being in all my life. She hugged me and pulled me into her as we continued to kiss.
I stopped kissing her just long enough to lift her up and sit her up on the pool table. I started kissing her again and I let my hand roam between her legs until it brushed against her cock. I felt as it flinched from my touch, so I reached inside her nylons and set her cock free. It began to stiffen under my touch.
I stepped back and when I did she looked up at me. “Well, It looks like I know your secret and as I have just showed you, I do not have a problem with it. Again, I lost our bet and I am yours to command.”
“You really mean it, don’t you? Bill, forget I just asked that. I know you meant what you said,” she stated.
“Command me, Tyssa. I want to pay my debt and I want to pay it in full,” I said.
She looked at me and said, “Remove my clothing, help me to get undressed.”
I slowly removed her nylons and I made sure to rub her smooth, sexy legs as I did. I then stood up and helped her to remove her top. Once I had it over her head, I looked down and saw her big perky tits and I was just about to lean in and suck on them, but I stopped because I was hers to command. I would not make a move until she commanded me to do so. I stood there waiting for my orders to begin.
“Kiss my breasts; I saw how you were looking at them. I know you want to. Kiss them and then I want you to suck on each one, bite the nipples gently because they are very sensitive.”
I did as commanded and I began to suck each breast and bite each nipple as I did so. She began to moan with each suck and nibble I gave to her. She ran her fingers through my hair and pulled my mouth tight over her breast. “Suck it, Bill! Suck it harder!” she let out. Again, I did as commanded.
She released her grip from forcing my mouth on her breast and leaned back. “Have you ever sucked a cock before?” she asked.
“No, I never really thought I would be put in this position to do so. I never thought of myself being gay let alone bi,” I replied.
“Then, I will make this as enjoyable as I possibly can. You are my first virgin, so to speak. I want you to enjoy it and at the same time come back for more.” She jumped up off the table and stood before me. “Kneel down and take my cock into your mouth,” she commanded.
I slowly sank to the floor and I was staring at her cock as it twitched, coming to life. She pushed her hips forward towards my mouth. I reached up and grabbed her cock and…I couldn’t believe what I was about to do...I opened my mouth and I let her slide he tip in.
I could taste her pre-cum as it slid past my lips and onto my tongue. She tasted salty but sweet. Slowly she pushed her cock into my mouth until I started to gag a little. She was testing to see just how far she could get her cock down my throat. As I began to take more and more of her cock down my throat, I felt it grow some more. I tried to pull back but she grabbed my head and began to fuck my mouth. Slow and steady, with each thrust I found myself taking damn near the entire length of her 8.5” cock into me.
“Yessss, that’s it Bill! I will go slow and easy. You are sucking cock like a pro. When you think you are truly ready for the face-fucking of your life, just moan out loud and I will take that as a cue to really fuck you good,” she said.
I let her work her length into me until I did finally have it all in with very little gagging. I moaned out loud and I let her take it from there. She again grabbed my head and began to force feed me her cock. She was picking up her pace and I felt her balls slap my chin with each thrust. She would go slow and then pick up the pace again. This went on for what seemed like eternity.
While she pumped her cock into my mouth, I reached up and slid my hands to her ass. I spread her ass, found the entrance and did everything I could to slip a finger up her shitter. My finger found its mark and when she pulled back, my finger broke through her entrance and went in up to my second knuckle. I started working my finger in and out of her ass at the same tempo as she fucked my mouth.
She moaned out loud as she pushed back into my mouth and held it there. “I’m cumming, Bill!” That was when I felt the head of her cock expand, her balls tighten and a thick warm gush of cum blast the back of my throat. I swallowed what I could, but the pressure was just too much that it escaped through my nose and out the sides of my mouth. I swallowed as fast as I could, but it wasn’t enough. Tyssa was shooting tons of cum for me to swallow.
When she finished shooting her load, she slowly withdrew her softening cock from the back of my throat. She pulled me up to her and she began to lick her cum from my face and chin. “You are the best cock sucker I have ever had the chance to be with. I am not just saying it, but I really mean it.”
“Thank you, I was scared at first, but you did what you said you would do. You were gentle up to the point I said that I was ready,” I said. I grabbed her head and I began to kiss her again, only this time there was a lot more passion behind the kiss.
“Did you really like that? Would you ever think about doing something like this again?” she asked.
I looked at her and replied, “I would love to do this again, but only if it can be with you. I would also like to reverse the role from time to time and maybe someday have my virgin ass taken.”
“I would love to get together again. I have so much to teach you and I know that there are things you would love to do to me, but until then…”
With that she dropped to her knees and gave me the most intense blow job I have ever had. We went into the restroom and cleaned up. We exchanged numbers and she left. I locked up and headed to the bar to meet my friend and to give him back his keys. While en route, Tyssa called me and said for me to drop by when I left the bar. I wrote down her address and was so looking forward to getting there.
But that is another story!
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<a href="https://www.lushstories.com/stories/trans/hustled-at-pool-1.aspx">Hustled at Pool</a>