Chapter 51
by
Jjaymes94
What's next?
Middle of the night
Dean wakes up in the middle of the night, there is no particular reason for this, it’s almost as if it’s a routine now. Realizing what time it was Dean knew that his girlfriend Brooke and his roommate Richard were probably having sex.
Dean grabs his phone to check the cameras. To Dean’s surprise his cameras he set up were still updating, that means he wouldn’t be able to spy on Brooke and Richard. This makes Dean mad and little bit frustrated. He waits a little longer to see if it’ll finish but it doesn’t look like it will be for awhile.
Dean yawns, he has been slacking on sleep lately. Between that and his laziness, he doesn’t want to get up and spy on them like he used to. He decides he can sit this one out, he doesn’t care to watch tonight. Dean happily goes back to sleep.
Hours later Dean’s alarm goes off and wakes him up to start his day. Two more days and it’s the weekend. He goes into the bathroom to shower not waiting for Brooke to come upstairs for her bedtime. She has one more day of this until her weekend gets started.
Dean relaxes in the shower, he for once got a full nights rest. Almost like a routine he feels himself getting a hard on. It’s been a routine for him to jerk off in the shower and today wasn’t any different.
Sexual thoughts filled his head, but this time he thought about himself and Brooke together like they used to. Dean doesn’t even remember the last time they had sex, but it hasn’t been that long, has it? While still pumping his cock he thinks, they had anal sex that one time but he was really just being used to stretch her out to fit Richard later that day...
Dean changes his thoughts because that was getting sad, instead he thinks about having sex with Brooke. Fucking her from behind and then cumming on her face. Imagining this, Dean ejaculates, his cum runs down the drain. He finishes up his shower.
Dean wants to have sex with his girlfriend again soon, maybe this weekend before he goes on his week long business trip. He hopes there is time for it. He hopes Brooke will let him fuck her.
Leaving the bathroom, Dean sees that Brooke is already in bed. The covers of the bed only come to her waist, she is completely topless. Her perfect boobs exposed, Dean takes a second to stare at her lovely breasts. He can’t stare any longer or he would risk getting to work late. He leaves to go downstairs to eat and go to work.
At work Dean gets his mind off of the things happening at home from the past couple weeks. Luckily for him he has a lot of work to do today.
Eventually the end of the work day comes and it’s time for Dean to head back home.
What's next?
Sharing is Caring
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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