📚 me & shari Part 6 of 7
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GROUP SEX STORIES

Rough Edges

Rough Edges

by Jpro56
20 min read
4.0 (1300 views)
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Me & Shari - Pt 6 - Rough Edges

I basked in the afterglow while soaking in the warm water of the hot tub reflecting on all the great things that had taken place in my life over the last six weeks. I had just been fucked silly and senseless by four beautiful women and over the last three days had enjoyed having sex with three of their husbands as well. Of course, the fourth one was with me, but this widower sworn off to marriage was suddenly not so put off by the idea.

I climbed from the tub and headed back to the house. The warm breeze dried me as I walked. Jim and Kurt were deep into a timed game of chess with a fifteen-minute limit. I asked what the wager was, and they both just smiled at me, meaning that one of them was getting a blow job or fucking the other. I poured myself a bourbon and went to watch the chess experts.

Chuck and the girls were nowhere to be seen but the light was on down in the last room on the south end of the house. The guys noticed me looking and Kurt said that Shari had told them to let me know that she would see me later tonight. Their hands were flying over the chess board not wanting to run out of time before the game finished. Jim was a better player, but Kurt could beat him if given enough time to plan his moves. I told Kurt that Jim had stacked the deck with the bet, but Jim told me that this was the rubber match, meaning that they had both won once.

I am not sure if I had distracted them or if Kurt was ready to give up because he was nearly out of time and losing but he made one wrong move and Jim had him checkmated in two more. Kurt acted upset but went with Jim to the lounger and started giving him an earnest blow job. I enjoyed the show. I do not think that I had ever just sat and watched one man giving another head. Kurt was good at it too. I speak from experience as I had enjoyed Kurt's oral minstrations many times. I figured that since that was the rubber match, Jim had cum a short time ago and this time was going to take a while. Surprisingly, Kurt was using a few tricks and had Jim moaning in pleasure quickly.

Kurt worked Jim's cock head sloppily with his mouth while his hands tugged on his balls. Jim was holding back trying not to grab Kurt's head and shove his cock into Kurt's throat. Kurt sensed it as well and wrapped his hands around the rigid shaft of Jim's dick to make sure that did not happen. Jim threw his head back as Kurt's tongue worked over the sensitive underside of his dick. The fact that Jim had recently climaxed did not matter because Kurt was already edging him, getting him close to orgasm then backing off till it subsided.

Soon Jim was begging to be allowed to cum. Kurt released his grip on Jim's dick and let it slide back into his throat. He felt Jim swell up and prepare to unload. He timed it perfectly for Jim to dump cum right onto his tongue. Kurt held the load in his mouth till Jim was ready to watch him swallow it in one gulp.

I got us all drinks and we sat and enjoyed ocean sounds and the tropical breeze. It was easy to sit and forget about the outside world but the knowledge that it was coming to an end was working its way into the back of my mind. Not that I wanted tomorrow to get here sooner, I also did not want to sit here and think about it. I told the guys that I was going to bed and headed off to the room that Shari and I had claimed when we first got to the island.

I slept restlessly alone in the big bed. I woke once and Shari was still not there. I thought about trying to stay awake waiting for her, but my body opted for a very long blink. I was dreaming of having sex on a beach when I heard Shari in the bathroom. I let her think I was still sleeping while she tried to silently get into bed. I had turned facing her side of the bed and when she leaned over to give me a kiss, I grabbed her, pulled her close, and made sure I got a proper kiss. She snuggled in against me and asked how I was doing. I told her that I did not want to leave paradise. She laughed and said that she felt the same way.

My hands started roaming down along her side, but she stopped me. Another kiss and she told me that she was tired and a little bit sore because she had a round two that was every bit as fun as the round one that I got and had two more rounds in the morning, all she needed now was to be held in the arms of the man she loved. I just held her tighter and told her that I loved her too.

Morning came much too soon for my liking although waking up to warm lips wrapping themselves around my dick made it worthwhile. Shari lovingly caressed me with her mouth until I was fully hard. She looked up at me and slid around and climbed on top of me. I took her in my mouth and worked getting her hard as well. She would not let me do some of the things I knew she normally liked for me to do so I asked if she was alright. She told me that she had a big morning coming up and needed to be ready for it.

I stopped trying to make her cum and focused on making her feel good while letting her make me cum. My hands found her soft fleshy tits and I rolled her nipples with my fingers. She moaned over my cock. She grabbed my hands and placed them on her head pushing downward. I took the hint and began forcing her up and down on my cock. She reacted by squirming and groaning encouraging me to do more. Holding her head firmly, I began thrusting my hips up, driving my cock into her throat.

I held her down and made her deep throat me until I heard her start to gag. I let her up to catch her breath before forcing her down on me again. This time I held her down until I filled her mouth with my cum. She willingly took all I had to give and wanted more. I finally had to beg her to stop.

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She rolled off me and turned to give me a kiss and cuddle before hopping up to shower and get ready for her morning activities with the girls. I gave her a few minutes then joined her. I made sure that her back and bum were good and clean by rubbing my body against hers until she made me stop. As she stepped out of the shower, I gave her plump round rump a good smack that left a reddened handprint. She noticed as she was drying off and told me that I was going to pay for that one later with a mischievous smile.

She told me that she would see me later and headed out the door. I finished my shower and joined Jim and Chuck out at the table for coffee and more of those magical muffins that appeared every morning. Kurt and the girls were nowhere to be seen so I assumed that he was first on the menu for the girls today. I asked the guys what was on the schedule for the morning. Jim said that it was up to Chuck and me because he had a feeling, he was going to be very busy later and wanted to be ready. Chuck and I both chuckled a little because we knew exactly what he meant.

Chuck and I headed down to the beach to enjoy our last morning in the surf, leaving Jim at the house for his turn later. We noticed a large fishing boat about a quarter mile out, largely because it was the only one we had seen that close to the island. It was there only a few minutes when we watched a police boat rapidly advancing on it from the other side of the island. The police pulled alongside and within moments the other boat was speeding away. The police boat turned toward the island and flashed its spotlight at the south end of the island and then sped back toward the mainland.

By the time they were out of sight we noticed that Jim had walked out to the beach with us. He told us that they were either lost fishermen or paparazzi thinking someone worth taking pictures of was on the island and if it were the latter, there would be an opening for a new investor later because somebody talked. I said that the response time was amazing and that if we had not been walking toward the beach, we would not have even noticed it. Jim said that there was an alarm up at the house that sounded when they stopped for too long. A warning for those guests and owners that needed to be aware of them.

The security at this place was amazing, and so were the precautions to ensure the privacy of everyone here. We stayed at the beach for a while kicking a volleyball around and playing in the surf. Eventually, Kurt came strolling down to the beach looking quite proud of himself. He told Jim that the girls wanted him to give them a few minutes to grab some food and they would be ready for him then walked out into the surf to soothe his abused body.

Jim waited half an hour and headed up to the house. Kurt followed him telling us that a nap with his name on it was waiting on a lounger. Chuck and I stayed down at the beach watching the boat that had moved well out to sea nearer one of the fishing spots that had been marked on the map for us on our fishing trip. I asked Chuck if he was feeling horny again yet. He said that Billie had taken care of him that morning but, yes, even with all the sex we had been having all weekend, he was feeling horny. I told him that I was as well.

A bit later we heard the girls up at the house giggling and laughing. Jim waved us up to the house. He asked us all to gather round and pulled out a small iPad and set it on the table. He said that before he showed us his new game, he had a question for us. He said that this game would pair us all up for a random amount of time then switch us all around. Then he told us that, if we were willing, he would like to add someone to our group. Miguel and his wife had been making sure that all our needs were taken care of this weekend and that they would like to join us for our some of our final full day on the island. Without hesitation we all agreed. Jim picked up the phone and told whoever answered to come on up, then began setting up the game.

It took a couple of minutes before Miguel, who piloted the boat from the mainland, and his wife Anya came around the corner. Miguel was an attractive thirty-ish guy. Well-built, muscled and dark skinned. Anya, however, was a Mayan goddess. Huge high set breasts and wide full hips.

Introductions were made and Jim set to explain his latest gaming creation. He told us all to draw a number from the box on the table without peeking. I drew number 9, Shari drew 8, Kurt drew 1, Becky drew 5, Jim drew 4, Jan drew 6, Chuck drew 7, Billie drew 3, Anya drew 2 and Miguel drew 10. The numbers were on a wristband, so we did not have to remember them.

Jim entered the number of players into to iPad and told us that it was set to pick numbers at random, pair us up and tell us a time frame from 15 minutes to one hour and we would all pair off for the prescribed length of time. Since everyone there, including Miguel and Anya were bi, same sex pairings were included, we all were fine with that.

Jim hit the start button and the female voice told us that the first round was to last 20 minutes. An alarm would sound when there were 3 minutes left before another alarm ended the round. She then read the numbers for round 1.

Chuck was paired with Jim, Shari was paired with Kurt, I was paired with Jan, Anya was paired with Becky and Miguel was paired with Billie. Everyone found their partner and moved to the loungers. I was not able to watch everyone as I really wanted to focus on Jan. We had all been naked together for so many days that there was not the awkward undressing stage. We just cuddled up together on the lounger. Jan was a completely different person to the one I knew just a few short weeks ago. She glowed with the new enlightenment and power of her sexuality. I gently touched her face and told her that I genuinely wanted to thank her and Jim for the weekend. It has been so much fun getting to build friendships to a new level and learning to love while being loved back so unconditionally.

She said thank you but shut up and make love to me, I shut up and did just what she told me to do. I started with nuzzling her neck and shoulders, light soft kisses and gently nibbling her ears. She melted against me. I could feel her small hard nipples on my chest and her growing clit pressed against my hardening cock. I slowly kissed my way down her lithe athletic body, spending time giving her red swollen nipples special attention. I lifted her arms above her head and kiss/licked my way down her side from her elbow to her waist. I spent time massaging and kissing her flat hard stomach slowly working my way lower.

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Her huge clit pressed against my chin and her hips were trying to work it closer to my mouth and tongue. I moved to the sides of her hips, finding a few ticklish spots in the crease where her legs met her pelvis. I finally moved my mouth over her clit but just let my warm breath tease it. She pushed her hips up to me, but I stayed just out of reach until she took her arms and forced my mouth down onto her throbbing clit. I sucked hard and buried it in my mouth while lapping her juices with my tongue. She ground her crotch into my mouth until she came with a scream and a gush of cum.

I gave her a few moments to collect herself and then rolled her over on her stomach. I took a moment to admire her slim firm ass then I lifted her hips up, placing her on her knees and let my mouth work on her privates. I used my mouth and tongue to lick from her still throbbing clit to working her tight pink asshole. Slowly I focused only on her tasty ass. When she started grinding it back against my tongue and mouth, I knew she was ready. I moved in behind her and at first, slid my cock easily into her hot wet pussy. I reached under her and stroked her long clit making her juices really start flowing. Without stopping stroking her clit, I pulled back and pressed my cock against her well lubed ass. She reacted by pressing back against me, so I let her set the pace. I watched the head of my dick slip into her. She stopped pushing so she could let herself adjust to the invasion. Never stopping stroking her clit, I felt her clench, then relax and shove herself fully against me. I could feel her ass again clench my cock as it slid deep into her hot ass. I felt her relax and then she told me to fuck her hard.

I drove hard into her ass. She grabbed the cushions and screamed into them while cum flowed from her pussy onto my hand squeezing her clit. I heard the iPad alarm tell us that there were three minutes left. I didn't feel like I would be able to recover for round two, so I decided to hold back and make sure that Jan was well taken care of.

Jan began shaking from cumming so hard for so long. I shoved my cock deep inside her and held it while one more orgasm racked her body. As it subsided, I lowered her to the cushions, let my cock slide from her still spasming ass and cuddled her close to me. Holding her and gently caressing her until the iPad alarmed to tell us that time was up for this round and the next round would start in ten minutes if we needed to clean up and get something to eat and drink.

We all started untangling and putting ourselves together. I glanced over at Shari and Kurt, they both looked flushed and happy. Shari caught my eye and gave me a loving wink which I returned. I found Anya as she hurried away to one of the many bathrooms. I was sure hoping that I was going to get a chance to spend some time with her, that ass was calling my name.

I met Shari in the kitchen area. She handed me some water and gave me a loving hug. She told me that everyone had noticed me fucking Jan and enjoyed the show. I apologized that I had been too involved to notice. I gave her a quick kiss, allowed if you are newly dating, and a pat on her ass. I realized that I was developing some pretty deep feelings for this ray of sunshine that had dropped into my life.

The iPad informed us that round two was beginning in two minutes. We all gathered to see who our next partner would be. The machine announced the next pairing would be Anya and Billie, Jan and Chuck, Jim, and Miguel, Me and Kurt and Becky and Shari. This round would be fifteen minutes with a three-minute warning before the end of the round.

Kurt and I headed off to one of the loungers as did everyone else. I asked Kurt if he had cum yet and he told me the Shari had made him come twice in that last round while he had only gotten her off once. I told him that I held back and did not cum with Jan, but I thought that she had cum at least four times that I counted. Kurt then told me that he was going to change that and leaned down to start sucking my cock. I hardened quickly and Kurt tried all his tricks to get me off. Finally, he looked up at me and told me that I would recover if I went ahead and came. I agreed and just laid back and enjoyed the feeling he was giving me. He had gotten enough saliva on my balls that he used it as lube and slid a finger into my ass. I lifted my hips and gave him better access. He found my prostate and gently massaged it while deep throating my cock. His tongue worked the sensitive underside of my dick, and I quickly reached the point of no return. My balls drew up close and I filled his mouth with cum. Five or six hot ropes went straight down his throat.

Kurt slipped his finger from my ass and let my softened cock slide out of his mouth. When I recovered some, I started down to return the favor, but Kurt stopped me. He told me that he was still trying to recover from my girlfriend for the next round. We did the un-guy like thing and just laid close while I stroked his cock. He was starting to react, and I thought about going down on him anyway when the alarm sounded the three-minute warning. That made up my mind and I leaned down and took his cock in my mouth. He made a feeble attempt to stop me but let me continue. I had him hard and ready when the alarm signaled the end of the round.

The iPad announced that round three would begin in thirty minutes and suggested that we all eat something. Once again, we all gathered in the kitchen and pulled out drinks, the stuff to make some sandwiches and some fruit. I found it interesting that none of the small talk was about sex. Anya and the girl's kind of stood in a group and the guys were talking with Jim about his game invention and what he was going to do with it. The iPad interrupted us with the announcement that round three would be starting in two minutes.

We gathered to be given our next assignments like good little perverts. Our new taskmaster, might be a good name for it, chirped that the next round was going to be two sets of five. The round would be one hour with the same alerts as before. Group one was Chuck, Shari, Jim, me, and Miguel. Group two was Anya, Kurt, Jan, Billie, and Becky.

Shari and her four guys moved to one of the loungers. Chuck and Jim each moved to side of Shari and started caressing her breasts and stroking her cock. I sat in front of Miguel and took his generous cock in my hands. His big full balls hung lower than his still soft cock and I fondled them as well. I asked if he liked them played with and he replied the more and rougher the better. I gripped his ball sack and lifted it to my mouth and sucked them both in. My finger pressed against his slippery asshole, I assumed that it had already been well used by his earlier partners.

I released his balls but kept my tight grip on them and lined his growing cock up with my hungry mouth. I opened my throat and let him feed his rigid seven inches deep into my mouth. I took several hard thrusts before he pushed me down on my back and straddled my chest, then refilled my mouth with his hard brown cock. He asked Shari if he could suck her sweet looking cock while the guys fucked them both.

The three disengaged from their activities and Shari stood in front of Miguel and teased his waiting mouth with her precum dripping cockhead. Chuck moved behind Miguel and Jim took his place behind Shari. Jim knelt behind Shari and started rimming her sweet asshole. I released Miguel's cock and took Jim's in my mouth. I wet him well with saliva and sent it on his way to fill Shari with cum.

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