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Chapter 198
by
Jjaymes94
What's next?
Dean opens up
Summer just opened up to Dean completely telling him something she probably hasn’t told anyone, ever. Their relationship was strong but now it made it even stronger. This was a big step for Summer to tell Dean. He could tell that it took a lot for her to admit all that had happened. Summer looked relieved to finally say it to somebody. Dean went on to tell her that he is proud of her and thankful that she entrusted him with this information. They shared a long hug.
While holding Summer, Dean couldn’t help think about his past that he hasn’t shared with her. Not to compare horrible things from their pasts but Dean believes that his past and events leading him to Summer are outrageously worst than her story.
“Summer, I should tell you something…” Dean says. He isn’t sure what he should tell her, she just shared something so meaningful to her, he should do the same. But he didn’t want to scare her off and telling the entire saga of Brooke and Richard would probably scare her off and tonight probably wasn’t the right time to unload all of that on her. So to start he would give her one thing.
“The reason I got a divorce was that my wife had a child with another man and I didn’t know until after the child was born. All through the pregnancy and the month after the child was born, I thought they were mine and I believe my ex knew I wasn’t the father and kept it from me.” Dean said. It wasn’t everything but it was a start.
Summer and Dean talked some more and comforted each other. They could now understand each other on a deeper level now, although Dean was holding some information back, eventually he would have to tell her, right?
Over the course of the next two years Dean slowly unveiled information about his past relationship with Brooke and subsequently Brooke and Richard. Summer was pretty shocked to hear about all the things Dean and Brooke did sexually together, all of this was foreign to her, she was a virgin and dared not look at porn either. Dean had to explain almost everything to her, she had so many questions. She may have thought some of the things were weird but she was willing to hear Dean out and come to an understanding on why they did those things together. One of the more shocking things to Summer was that Brooke used to share Dean with her friends, she couldn’t understand cause she always saw sex as a very intimate thing reserved for loved ones. Dean tried to explain how it can be different and that it is a mindset. That you can deviate your feelings and thinking that sex is just sex. This was also all before he even got to start explaining about the Richard saga. It took Summer time to understand but she understood eventually.
Dean was making progress on Summer, not sexually at all, but with helping her understand him and his past relationship. Summer was surprised to hear how sexual and kinky he was and couldn’t believe it because of how he is with her. He had to embarrassingly admit how he masturbates a lot but Summer understood. Dean told her that he respects her and knows she wants to take things slow and not push anything on her, she appreciates that a lot.
Now eventually he had to get to the Richard part of his story. He hoped Summer could understand, he was most nervous about this, he hoped this wouldn’t change the way she sees him.
Dean started off at the top of the story, he explained who Richard was, his nerdy roommate. He then went on to explain the Master Plan and how at first it was to help his roommate. Then eventually it turned into something completely different and out of control. Summer of course had a lot of questions and Dean answered everything as best as he could. She was very understanding and supportive, she could tell how big of a deal this was for Dean to tell her. Dean didn’t realize how much weight was lifted off his shoulders when he finally was able to tell someone about everything.
There were no longer any secrets between Dean and Summer.
It has been 5 years since the beginning of Dean and Summer’s relationship. Dean was now 32 years old and Summer was now 25. They have grown together as a couple, they know each other’s pasts, they understand each other, they have opened themselves up completely to each other emotionally. They were in a healthy relationship.
How about a sexually healthy relationship? Not so much. Summer was still a virgin by choice but there is nothing wrong with that. Dean has not seen Summer nude and has only touched her over her clothes. She has now given Dean 5 handjobs, one for every anniversary. Summer has never orgasmed while Dean orgasms frequently by jerking himself off. Something’s got to budge?
Dean was in the best and most healthy relationship he has ever been in, he obviously had to take the next step.
What's next?
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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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