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Chapter 230
by
Jjaymes94
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Everyone is a Winner
Dean, Summer and Ron all took a sip of their drinks and silence filled the room. They all seemed to be thinking about the deal they just struck and how it benefited them. In their minds there was no loser in this situation or maybe not an obvious one.
Dean had some doubts in the back of his head but this deal would be beneficial down the road for him. He may have to suffer in the near future but it’ll get better for him. Just a little over six months from now he wouldn’t have to share Summer anymore also not having to pay for the ceremony or honeymoon and Summer getting a full time job, they will have plenty of money for their future together.
Ron finished his drink, “Well this has been very productive, I’m going to head out now.” Summer also finished her drink, “I think I’ll go with you…” she stood up. Has it started already? Is this how it’s going to be?
“But wait,” Dean said, both Summer and Ron turned and looked at Dean. “What about dinner?” He asked. Ron was quick to answer, “I’ll feed her, don’t worry.” Summer chuckled, “There’s hot dogs in the fridge you can cook, I’ll be back before bedtime,” she grabbed her notebook and brought it over to Dean, “enjoy” she said with a smirk.
Dean stopped her once more, “Wait,” he stood up and embraced Summer in a kiss, as that is all that he is able to do, he should try to do it as much as possible. It was a kiss that lasted a little, there was some passion and a little bit of tongue. Summer blushed a little when it was finally over. Dean had to try to assert some dominance in the situation, Ron didn’t seem to care. “Time to go,” he said before walking out, Summer followed him close behind.
Dean sat down alone with Summer’s notebook, he was excited to read what she had written about her bachelorette trip with Ron. He flipped through the pages to see how many new ones there were. To his surprise there were 30 new pages! He decides he would cook dinner before he got started reading. He sadly cooked up his sad meal of hot dogs.
Dean started reading and eating but quickly turned to reading and jerking his cock. He couldn’t believe how in detail Summer was going on about everything that happened. Then he was in absolute shock that Ron fucked Summer in her ass and she liked it! Dean couldn’t control himself and came only after 15 pages, he was turned on but also jealous at the same time. He missed out of anally fucking Summer with this new deal they all agreed to, he will have to wait until after the wedding.
He had to take a break from reading for a second to collect his thoughts. He looked at his hot dog he didn’t eat, he couldn’t eat it now after reading in detail what Summer thought about Ron’s cock.
Dean’s break didn’t last long, he wanted to know what else was written. He read on about Summer wanting to have more anal sex in the morning in great detail. Dean of course came once more. Summer had a way with words, Dean could almost imagine all that was happening like it was right in front of him, sometimes he wishes it could be in front of him, or was that too much?
Dean looked at the clock, Summer wasn’t gone very long, she probably would be gone for the night and come in just shy of midnight. Based off what she wrote in the book, Ron was probably drilling her asshole and Summer would be taking it as long as possible before she would get back.
Dean laid in bed awake and just as he predicted, Summer came home within minutes of midnight. She got ready for bed. Dean made sure to share a kiss with her before going to sleep, making sure she wouldn’t forget about him. “I love you,” he said. “I love you too,” she responded. Day 1 and there was nothing to be worried about it.
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A story about being a generous roommate
Dean and Brooke have been dating for quite some time now, completely comfortable together. They love to experiment in the bedroom and try anything. Richard is Dean’s nerdy roommate, they have know each other most of their lives with their parents being friends and neighbors. Dean feels bad for Richard because he has had no luck with the ladies. A virgin nerd who use to live in his parents basement until Dean was convinced by his own parents to have Richard move in with him. Dean figures he could help Richard out once more and share Brooke with him and tap into another sexual fetish of his... win-win? Right?
Updated on Jan 28, 2026
by Jjaymes94
Created on Sep 12, 2020
by Jjaymes94
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