Chapter 42
by
Jjaymes94
What's next?
End of the Weekend
Dean wakes up and checks the clock. It’s almost noon. He faintly remember waking up in the early hours of the morning. He second guesses himself, was he dreaming? Did that even happen? Thinking harder about it, what did he even hear? Was Brooke moaning? These were many unanswered questions Dean woke up to.
Dean rubs his eyes to wake himself up more. Brooke hasn’t come to bed to sleep yet but she’s probably due to come soon. Thinking about Brooke made him remember the master plan. He pulls out the notes he scribbled down when he snuck a peak at the plans.
Yesterday was supposed to be anal for a second day but that didn’t happen, Brooke was way too sore to walk let alone get fucked in the ass again. Dean searches down the paper for what is on today’s agenda:
Sex.
Dean didn’t have to elaborate on this one, sex meant they were going to fuck normal, vaginally. But wait, Brooke’s day is about to end... she needs to get up at 8pm for work and she’s going to bed soon... Dean puts the pieces of the puzzle together.
They already had sex.
He missed it. It must have been the noises he heard that woke him up. If Brooke followed the plan, he already missed it. Upset with himself, he puts his notes away and sulks for a little bit.
Noon hits and Brooke comes into the room on cue. She starts to get ready for bed, she’s exhausted. Meanwhile Dean is getting up for the day, well-rested. Fully clothed, Brooke flops on the bed, grabs a sleeping mask, puts it on and immediately tries to sleep. She didn’t even bother to say anything to Dean in the process. He decides to go downstairs and leave her be.
To Dean’s surprise he finds Richard already downstairs in the living room watching TV. Richard was usually a night owl and Dean never usually saw him until the evening if at all, maybe it’s the new normal. Dean takes a seat and talks to Richard and tries to get information out of him. Obviously Richard won’t confess about the affair but that’s not the information Dean was searching for. Dean wanted to know if he has changed up his life, like how his room is cleaner, he actually talks to Dean and is out of his room more than he is in it. Richard just brushes off the question and says he isn’t any different than before. Maybe he wasn’t aware himself that he was changing for the better.
Richard let’s out a big yawn and says he going to go upstairs to play some video games. Dean is suspicious, he could be telling the truth or he could be lying. Dean suspects that Richard is going to sleep so his schedule will match up with Brooke’s. Why wouldn’t he, it’s not like he has a job or anything better to do than to fuck Dean’s girlfriend. Dean waves bye to Richard as he walks up the stairs to his room.
Dean blankly stares at the TV not actually processing, just zoning out. He has so much time and nothing to do today. He flips through his phone to pass time.
Dean makes himself dinner and eats it by himself, he continues to vegetate in the living room. Richard doesn’t come downstairs again until almost 8. This reminds Dean that Brooke should be waking up soon for work. He decides that he should greet her so he goes upstairs leaving Richard behind in the living room.
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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