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Chapter 44
by
Jjaymes94
What's next?
Brooke goes to work
Dean comes out of the bathroom and finds Brooke already dressed for work, only she isn’t wearing any pants. She is wearing a dressy shirt and only a thong. Dean questions this, Brooke says that they only will see her from the waist up in the video so why not be comfortable. Dean can’t argue with that logic and she walks out the bedroom to go start her work day.
Dean gets dressed as he was still naked from before. It’s too early to go to bed so he decides to go downstairs.
Dean reaches the bottom of the stairs and sees Richard sitting on the couch, he forgot he left him down there when he went to go wake up Brooke. Richard must have gotten a good show since Brooke had to pass him in her thong.
Richard and Dean make small talk as they watch TV. Dean can hear Brooke talking away in her office.
It starts getting late, Dean is feeling tired and probably should go to bed soon he has work in the morning. Richard usually would leave and go upstairs before Dean but tonight he was still up looking wide awake. This made Dean suspicious, but he couldn’t do anything about it anyway at this point and he doesn’t want to. Dean wants to continue with the plan, he really is helping Richard out.
Dean heads up to bed while Richard continues to watch TV in the living room. Upon entering his room, Dean decides to not close his door all the way, just in case their are any sounds in the middle of the night he would like to check out.
Dean falls asleep.
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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