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Chapter 33
by
Jjaymes94
Where does Dean look?
The bathroom
One stop that Brooke made before unlocking her drawer and after putting everything away was the bathroom. Dean searches in every nook and cranny. He goes through the cabinet checking everything. He comes along a box of condoms, he doesn’t remember the last time they used condoms... if ever. He looks in, a key! What a clever girl, hiding it in a spot he wouldn’t stumble upon normally.
Dean practically runs back into his room hops over the bed and gets to the table. He opens it up, grabs the paper and starts reading away. He slowly remembers everything that has been written. There have been additions written in pen by Brooke, there’s check marks next to the days that have been completed, multiple check marks next to a day that said one blowjob, with one being crossed out. One thing is certain, they didn’t have sex yet.
The word anal has been circled multiple times, Dean was correct, today was the day. Dean wrote down notes on another paper on what was to come in the following days, he was tired of not knowing.
Upon further inspection in Brooke’s secret drawer, Dean finds pictures of Brooke... Dozens of Polaroid pictures with Richard’s cock in her mouth.
Dean figures he has some time, he lays on the bed, pulls his pants down and flips through the pictures. He gets through five or so pictures before blowing his load onto his chest.
Dean cleans up and carefully puts everything back into the drawer the way he found it.
With an unknown amount of down time, Dean finds himself not sure what to do. An hour or so has passed since Brooke and Richard left so it’s possible that they come back soon and it’s too early for him to leave and fake coming back from work, he didn’t want to sit in his car for that long. Dean settles on snooping a little more. Taking advantage of the empty house, he decides to investigate Richard’s room for anything, Dean isn’t really sure what he’s looking for.
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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