Beaten by Sherry by Kirk (EKIRKK@aol.com) Sherry gets fifty dollars richer at the physical expense of Kirk. This story and the following stories are true and happened when I was dating my wife. I was lucky enough to have a few wrestling encounters with her Aunt Shirley, her cousin Sherry, Sherry's friend Dawn, and my sister-in-law Kim. During the dating period of my wife, she and myself we would go over to her aunt's house on Friday and Saturday night and play cards all night. Also on most Sundays we would gather at their house or mine and grill and relax. Depending on the night, sometimes we would drink while playing cards. The job I had at this time was a physically demanding job that worked Monday through Saturday, 5:00 AM to 7:00 PM. So you can imagine at the end of the work week I was pretty beat and usually needed a relaxing evening on Saturday and Sunday to unwind. The card game we played is Rook and the teams were always my wife and her aunt, Shirley, against myself and my wife's uncle, Joe. During the course of one of these card games, the discussion got onto wrestling. It was no secret that I enjoy female wrestling. These card games were wild and no quarter was given by anyone. Shirley boasted that she could beat my butt in a wrestling match and then make me kiss hers. Shirley is a very well endowed lady, 5'5" tall and approximately 12 years older than myself at this time. I am 26 years old, 6'7" and weigh 260 lbs. and am in pretty good shape given the work I do. Shirley's daughter, Sherry was walking through the room at this time and she said she could also beat my butt and make me like it. Sherry is a brunette that is 5'7" tall and has a lean physique. Sherry has always been known by me as my wife's wild cousin. Sherry worked at a country club and worked most nights and usually got off on Sunday at 3:00 PM. I told Sherry if she could beat me in a wrestling match I would give her fifty dollars. Sherry asked where we were grilling Sunday and when she got off work she was going to make herself an easy fifty dollars. We decided to grill at Shirley's house Sunday and the match would take place then. We agreed that If Sherry could pin me or make me submit she would win the fifty dollars. Shirley stated she wanted a piece of me too and would wait until her daughter had kicked my butt first (this is another story). Sunday arrived at approximately 12:30, my wife and myself arrived at Shirley's house. I had blown off the challenge issued by Sherry two nights ago and really didn't give it much thought. We immediately started playing cards with an extra incentive thrown in that the losing team had to do shots for each lost hand. During the game, Joe and myself were also trying to get the grill ready and start the food also. Later I learned that my wife and Shirley were fixing the cards when we would go check the grill. By the time we figured something was up, we were to drunk to care. We were trying to have the food ready around 5:00 PM so that Sherry could eat when she got off work. At approximately 3:30PM, Sherry walked through the door. She asked if we were almost through playing cards cause she was about to get her fifty dollars. Shirley and my wife, with big grins, said I think he is about ready. Sherry went into her room and took off her uniform and came back in tight blue jeans, a tight mid drift top and barefooted and said she was ready. Needless to say my current condition was going to be a big liability but I outweighed her by almost 140 pounds and figured that I would just get her to the floor and lay on top of her till she gave up. The living room furniture was pushed against the four walls and my wife and Shirley sat on the couch while Joe was running back and forth checking the grill and sat outside most of the rest of the afternoon. To try and even things out, I started on my knees and Sherry started the match standing. I grabbed for her legs and tackled her to the floor and was easing up on her body to just lay on her till she gave up, I had just got into a cross body pin position and Sherry swung her legs up and caught my head and took me over onto my side in a side head scissors. Sherry yelled that she was going to squeeze my head off. I was twisting and rolling trying to pull my head free from her legs. Sherry was laying on her side laughing at the effort I was having to use to get free from her scissors. Naturally, my wife and Shirley was yelling for Sherry to knock me out. Sherry kept trying to get me to stay still so she could really lock down the head scissors. The only thing that kept me from going out right here was that I immediately started squirming and twisting when her thighs first closed on my head. Finally I managed to pull my head out of her scissors and my head felt like it was on fire and about to explode. Shirley commented on how red my face was. They told Sherry to get me back in the scissors and that would finish me. I just layed on the floor a few seconds trying to get my bearings and then rose to my knees to face Sherry again. I knew I needed more rest so I complained that her blue jeans were cutting into my skin. Sherry said she could fix that and my wife and her went into her room and Sherry returned wearing a tiger print bikini. Sherry has a very tight body and her body is not over muscled but her lean physique shows the muscle with the least little effort. So you can imagine I was gawking and liked the idea that I was going to get to touch her. Looking back though, what a painful price to pay to do that. Sherry has a reputation as a tough girl and you could very easily se why. Sherry sarcastically said that she was not going to let me have any excuses after she whooped my butt and in addition to the fifty dollars, I would have to kiss her butt and she turned and showed me her butt. Any other time if she would have asked me to kiss her butt, I would have been more than willing to do it, but not under these circumstances. Sherry asked if I was ready to start back and I nodded yes. Sherry turned sideways and sent a side kick into my back. The kick almost knocked me down. Being the arrogant he-man I thought I was, I said do it again. Sherry turned and kicked me with her barefoot again. Sherry repeated this barefoot kick three more times, one right behind the other and the third one sent me to the floor. I was not dazed and starry eyed, but the force of the kicks successively actually knocked me to the floor. I was amazed Sherry could do this, given the fact that I have had my fair share of scraps growing up and have always been known as a pretty tough guy. After falling to the ground, Sherry jumped on my back and applied a camel clutch minus the locking of my arms. Sherry was grinding her butt into my back and pulling my chin back. Sherry held this hold for a few seconds and then got off me. Sherry told me she was going to take her time and wanted to enjoy putting me through pain cause she wanted to earn her fifty dollars. Sherry jumped to her feet and started with the kicks again. This time the kicks came to any place that she could land her foot. A thought entered my mind that she had not kicked me in the head yet, I should have kept my thoughts to myself. Sherry delivered a bare foot to the left side of my face and knocked me onto my side. Sherry yelled that she liked kicking me in the head better than the back. I don't know if this was a ploy because I started protecting my face and her feet started connecting with my stomach, sides and back. I never knew Sherry to taken any kind of martial arts before but when I tried to recover from one kick she was already in position to deliver another to a different part of my body. Just the sight of those gorgeous legs beating on me would normally have been very exciting but not with Shirley and my wife watching and the toll those legs were having on me. I got back to my hands and knees and Shirley told Sherry to get me in that hold she had me in with her sitting on my back. I was taking a lot of punishment and Sherry kept up with the kicking. Sherry shot a kick to the back of my head that caused me to fall onto my face and Sherry jumped onto my back. This time she hooked my arms over her thighs and pulled back on my chin. Once again Sherry was grinding her butt into my back, this time it was very uncomfortable from the kicks she had just delivered to my back. If it wasn't for the pain I was in, this would have felt great. Sherry pulled my chin with a rocking motion and then held it at the top position and leaned down and whispered in my ear that she was going to sit on my face in front of everybody. Sherry giggled a little and said there was nothing I could do about it. Sherry then let my head fall to the floor but remained on my back. Sherry kept trying to pull both my arms behind my back but I still had enough strength to stop this. Shirley jumped off the couch and grabbed my right arm and Sherry grabbed my left arm and together they bent both my arms behind my back. Sherry then sat on my arms pinning them in place. Sherry then grabbed my hair and pulled my head up so that she could look into my face. Sherry grinned real big and said "you know it's only a matter of time before I wrap my legs around your head and knock you out." I could not just lay here and take this beating, so with my last burst of strength, I got to my hands and knees with Sherry still on my back. Sherry tried wrapping her legs around my waist and wrapped her arm around my chin in a chin lock. She was barely able to lock her feet in a body scissors. Sherry released the body scissors and chin lock and slid up my back, grabbed my hair and pulled the back of my head into her crotch in a standing head scissors. I had seen these executed before and could not figure how people could get caught in this hold. Sherry crossed her feet and kept both hands in my hair and squeezed her thighs with pulsating thrusts. This was starting to make my head feel hot but it didn't hurt near like the first head scissors Sherry had put me in. Sherry has really smooth thighs and stays in the sun or sun bed. This position really wasn't that bad, I could feel Sherry's thighs and her skin was soft and this was a perfect fit for the saying, "if you got to go". Sherry worked the head scissors and continued to tell me how much she was enjoying kicking my butt and what she was going to do with her fifty dollars. Sherry uncrossed her feet to get a better stance and grip and I saw my opening. I grabbed both her feet and sent Sherry to the floor. I hesitated just a second and had plans to jump on Sherry and hold her down. I jumped but Sherry had turned over onto her back and was able to snare my neck with her thighs in a front head scissors. I mean how stupid, I just jumped right into a perfect head scissors and Sherry didn't have to work to get it. My head was buried deep into her thighs and I knew it was just a matter of time, or whenever Sherry wanted to end it. Sherry grinned and said this is better because she wants to watch me pass out. Sherry started with a pulsating squeeze and grinding motion. Sherry kept just enough constant tension so that I could not pull free and would give the bursts occasionally. The feel of her thighs was so provocative I couldn't help but get hard as a rock. This had to be a sight to see, a 6'7" grown man lying on my belly with this 5'7" bikini attired babe with her thighs locked around my head. Sherry was eight years younger than me and weighed half as much, so imagine the size difference. The grinding motion was beginning to take effect and my head felt like it was on fire. When Sherry would squeeze, I felt her thighs with my hands and the muscles would bulge. Sherry kept this perpetual smirk on her face and kept squeezing with pulsating thrusts. Sherry said it was time to finish this, she leaned back, gritted her teeth, grabbed my hair and pulled my head deep into her crotch. Not only were her thighs killing my neck, but now my mouth and nose was covered by her crotch. Sherry said this is it and grunted with a tremendous squeeze. I saw black dots and the last sight I saw was Sherry's stomach muscles ripple with the final squeeze. It seemed like I was out for hours, but they said it was only a few seconds. When I came to, Sherry told me it was time to pay up and told me to crawl to her and kiss her butt. I was very shaky but managed to crawl to her and she presented her butt, which I kissed with a long french kiss. Sherry said there was something that she did not do, but would wait after dinner to take care of that. I had a tremendous headache and had been humiliated by my wife's cousin. Sherry and my wife went into the back and when they emerged, Sherry said that my wife had given her the ok to use the face sitting hold. I thought I could get out of this but there was no escape. I was still laying on the floor and didn't think I could move and knew I couldn't put up much resistance against Sherry, but I was not going to let her sit on my face with my wife and Shirley watching. As I attempted to get up, Sherry grabbed my right arm and put her foot on my face. Sherry started twisting my arm for all she was worth. At the time I didn't know, but later Sherry told me she was taking away my arm so I couldn't use it to defend myself. Sherry then moved her foot to my throat and was cutting my air off. Sherry then dropped my right arm and grabbed my left arm and did the same twisting to it all the while cutting off my air with her foot. Sherry then dropped my left arm and jumped onto my chest in a high schoolboy pin. Sherry smirked at me and kept sliding higher and higher on my chest. All I thought was how did I get in this position. My arms felt like jello and they hurt to move. Finally Sherry slid her crotch onto my face and started grinding. I heard both women ask Sherry how it felt, and Sherry said she was fixin to come and asked my wife if she could. My wife told Sherry yes and make me lick her to finish. Before they could finish the sentence, Sherry began to orgasm and I thought she was going to grind my head into the floor. Sherry rolled off me and told me there would be a re-match, but next time she would make sure I was fresh because she thinks she can take me anytime. I overheard Sherry telling my wife and Shirley she knew she had me when I was in the front head scissors and went from trying to pry her thighs apart to massaging them. Sherry said that was the perfect sign of surrender. I think Shirley wanted her match right then but was overruled and agreed to wait until later in the week to wrestle me. That is another story and I will write it later. I was very humiliated and aroused and the same time, a very funny feeling. All three ladies promised to keep this amongst themselves. Sherry said she had to tell her best friend Dawn, which it was later learned that Dawn had helped Sherry with some of the holds she used on me. Late that night, my future wife and I made love for what seemed like an eternity and we were both very aroused and were able to maintain it. My wife said she was going to get Sherry and Shirley to wrestle me more often if this was going to be the result. Overall, I wrestled Sherry four times, her friend Dawn twice, and Shirley six times. I will try and write all the stories and send them when I have time.