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Introduction: Loser has to pay up!!! I had been away with work for 3 long weeks and I still had another 3 weeks to go before I was due to fly home. Luckily Jen had agreed to fly out to stay with me that Saturday night to go out for the night. I collected her from the airport and we went back to the hotel for Jen to get changed. About an hour later Jen emerged from the bathroom looking amazing. Wow was all that I could say. I bought this dress just for you said Jen. I looked her up and down. She was wearing a striking tight halter neck blue dress with 5 high heels. It was the shortest dress I had ever seen her wear and it accentuated every inch of her 56 130lb frame especially her 32E breasts.

I suggested we try a bar called Barneys, which was just down from the hotel. When we walked in there was a good crowd inside there and the barman suggested we go into a side room, which was a lot quieter and had a pool table. When we went in there were 2 guys playing pool inside there. As I ordered a few drinks the guys were complimenting Jen on hot she looked and how I was a lucky guy. They challenged us to a game of pool so I suggested that Jen play as I was not really into pool. OK said Jen. Be careful with that dress I joked they may see your knickers. Jen smiled at me and whispered in my ear oh dont worry about that, Im not wearing any. She winked at me and walked over to the pool table wiggling her sexy ass as she did so. She sure knows how to turn me on. What are we playing for? asked Jen. How about your dress? quipped one of the guys we win and you have to give us a strip tease. And what if I win? asked Jen. Honey, you win and you can have anything you want he exclaimed confidently. Sounds good to me said Jen with a smirk. The balls were racked up and the game began. 9 ball it was. The first guy broke and potted a ball. He then missed the easy second ball. He winked at his pals as he handed Jen the cue, no doubt looking forward to watching her bend over the table in that short dress, as indeed was I. Jen took the cue and leant over the table, her dress writhing up as she did so, but not far enough for the guys to see anything.

She walked back over to me for her drink and said Babe, this is fun, I think I can win. As she walked back over to the pool table I saw the guys wink to each other again. They left a few balls hanging on the pockets for Jen to pot. Jen potted them and said I wonder what I am going to ask for when I win. She missed her next shot and the guy went to the table saying get ready to strip honey, because this game is over. With that he played the 6 ball off the 9 ball potting it and winning the game. Strip, strip, strip chanted the guys. Jen looked at me. I shrugged my shoulders and said you took the bet. She smiled, turned to the guys and said ok guys, get ready for a show. She stood up on the pool table and started dancing to the music in the background, her hands rubbing her fit, toned body. She knelt down on the table and asked one of the guys to unzip her dress. He did not need to be told twice. With her dress now unzipped Jen stood up still dancing sexily. Her hands were now on the top of her dress and she slowly slipped the top down over her 32E breasts and rested it on her waist. She unhooked her bra and cupped her breasts in her hands. Off, off, off came the chants from her eager audience. With a big smile from Jen, and a loud cheer from the guys, Jen flung her bra at one of them exposing her big firm breasts with her nipples erect. Thats it guys, thats your show said Jen as she went to get off the table.

I could see the disappointment on the guys faces and decided to take control. I was enjoying watching the 5 guys drooling over Jens incredible body and I could tell from her erect nipples how horny Jen was. You are not finished yet I shouted over to Jen you promised to strip, so strip. Jen smiled at me. If you say so said Jen as she stood back up and started to dance sexily again. Her hands grabbed the bottom of the dress and she slowly inched it up along her thighs finally exposing her bald shaven pussy to her encouraging audience. It was a sight to see Jen standing on the pool table with her tits and pussy exposed, her dress more like a belt around her waist. Remember what we arranged guys? She is all yours I said to the guys. What do you mean? asked Jen. I replied I organised for these guys to be here tonight. Do you remember telling me about your fantasy of having 2 guys fuck you? Well now it is going to happen. Lie down on the pool table and get ready to be fucked hard. She smiled at me and said wow, turned to the guys and said you heard my husband, get your cocks out and fuck me.

She lay down on the pool table and one guy started kissing her passionately on her lips while the other guy started sucking her erect nipples. Jen let out a moan as his mouths surrounded her sensitive nipples. He then moved down and gently parted her legs, kissing up along both thighs before flicking his tongue on Jens clit causing even more moans from her. The 2 guys continued to ravage Jens body with their mouths as they stripped. When they finished stripping one of the guys stood at the end of the table with his 9 cock in his hand. Stand back he exclaimed as the other guy stepped away from the table. He looked Jen in the eyes and said time to sink the 9 into the hole. I had to laugh at this pool/cock size analogy. He climbed onto the table. As he moved into position, Jen moved her pussy lips apart and smiled this hole is open but it is a tight shot. He smiled Oh Ill get it in there alright as he slowed eased every inch of his 9 cock into her well stretched pussy making Jen moan loudly in pleasure.

As he continued to pound her pussy the other guy moved to the side of the table and Jen took his cock in her hand and started to stroke up and down along the shaft. Before long the guy fucking her let out a loud grunt as he filled her pussy full of cum. As he moved away the other guy quickly replaced him. He stood at the end of the table and grabbed Jens legs pulling her close to him, her ass now resting on the cushion of the table. As he easily slid his cock into her cum soaked pussy he whispered in her ear time for you to cum. He drove hic cock hard and deep into Jen with a loud groan on each thrust. Jen began panting loudly and beads of sweat started rolling down her tits. She wrapped her legs around him and pulled him closed with every stroke he made, determined to get every inch of his cock. Before long she put her hands in her hair, arched her back off the table pushing her chest into the air as she came with a loud moan. This was as much as the guy could take as he added his load to that of his buddy.

Jen stood up and walked over to me, her dress still around her waist and cum running down her leg. She caught my hand and placed it on her soaking pussy. There is room for more cocks there she said lets go back to the hotel so you can take care of that, and just maybe I will tell you about out another fantasy of mine a gangbang with 4 or 5 more guys. With that she pulled back up the top of her dress and pulled down the bottom of the dress as she walked to the door.

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In the fall of 1996, computer program software was exploding, and, as a freelance code chopper, I was raking in the bucks. So I was hard at it when 13-year-old Betsy walked in and cheerfully announced. “I just had my period, Daddy.” “Uh, aha, um, well… right. Did you use the stuff we bought?” “Of course; I’m not mentally challenged.” She grinned all over her plump, pretty face. “You know what this means, Daddy? Now we can really do it!” Oh boy. To be plain about it, my...

Pool Cleaning Day

POOL CLEANING DAY I woke up late Tuesday, and suddenly remembered it was pool-cleaning day. I could hear the locusts, and knew it was going to be another hot day. I put on a jockstrap and my swim trunks, the black denim ones made like shorts with the Red Cross Swim Instructor’s badge sewn on, and dug around in the bottom drawer for a tee shirt that wasn’t full of holes. A pair of tennis shoes, and I was dressed for the day. On my way to the back door, I stopped and grabbed the pitcher of OJ...

Pool lessons

Like most boys of 12 I had been more interested in football, swimming and mucking around with my mates than girls, sure I knew they were around and in fact I had a fair few friends that were girls, I just hadn’t taken much notice of them. As school went on I join the football team and then the swim team, our PE teacher coached both of them and had seen me swimming and after a long chat had got me to agree to swim. Joining the swim team gave me more chances to use the local pool without...

Pool party cousin fuck

Now how did this happen well it was during the summer and her mom was hosting a party. I didn’t like her mother much she always liked to brag about how great her children were. They were geniouses though Katie being the smartest. She wasn’t the prettiest but I thought she was cute. They got a pool in their backyard and told us to bring our bathing suits. So my family and I got in the car and took the 30 minute drive to my cousin’s house. We got there and were greeted by Katie’s mother her two...

Pool Hang Gang Bang

Me – 27 year old man Mary (my wife) – 23 year old blonde Them – strangers in a pool hall in the wrong part of town. This story is true, our names are real (I am Kevin, she is Mary). This is told from my (Kevin) perspective. It was a Friday night in summer. We had partied many times before. I love watching Mary suck and fuck guys other than me. We prefer strangers cause it is scary and nastier than regular fuck buds etc. We will from time to time visit nearby cities and do this. We live in...

Betsy

Betsy and I had been married for a little over twelve years. We were living the American Middle Class Dream. Three great kids, our own home, two cars in the garage — the whole bit. I had always thought that ours was the perfect marriage. I loved her and I'd always thought that she loved me, but I recently found out that my loving wife had a secret life — a life that cast doubt on whether she had any feelings for me at all. I'd be insulting Betsy if I said she was a stay at home mom who...

Pool Fuck Fun

“So, did you have a good time in Cape Town?” asked Maria, as she manoeuvred the Mercedes out of the airport car-park, narrowly avoiding being mown down by an enormous truck carrying a teetering load of timber that seemed to be secured with little more than string and a prayer.“It was awesome,” I said, truthfully. What had seemed like an opportunity to spend a relaxing week in the company of an old friend from university had turned into something of a sex-fest, with much fucking and fun with...

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