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Chapter 53
by
Jjaymes94
What should Dean do?
Push through
Dean decides to keep moving forward with the plan. It is still not complete and he believes he can last a little while longer. If things don’t start progressing by the time his business trip is over then he might have to pull the plug on everything.
For the mission to become a complete success, in Dean’s opinion, the following needs to happen for Richard:
-Get his own girlfriend or at least sleep with other people besides Brooke
-Get a job
-Move out
These things don’t necessarily have an order to them but once these goals are all accomplished Dean can say the experiment was a success and then it will finally be over. He might have to guide Richard in this direction subtly. Dean gets a little hard on thinking about his plan, there’s new excitement about it especially the feeling that it could all be over soon.
Once the master plan is done, Dean can move on with his life but for now he can just daydream about it.
Dean can hear someone coming down the stairs. It’s Richard walking down, Dean is not surprised at all, he always comes down before Brooke does. He doesn’t blame him, Brooke is sexy and he wouldn’t pass up an opportunity to see her. Dean thinks Richard looks a bit more muscular than normal or it’s just his imagination. Richard takes a seat on the couch.
Dean doesn’t let the time he has with Richard by themselves go to waste. Dean instantly starts to chat up Richard, trying to get a feel of where he is at in his life. Dean asks Richard about a job without telling him ‘get a job.’ Dean asks about turning his interests into making money. Richard admits not thinking about it and liking his life the way it is right now. Dean rebuts that having some money can be used for cool things. Dean then turns the conversation to dating and leaving the house to meet girls. Richard obviously doesn’t say anything about fucking Dean’s girlfriend. He just kind of shrugs. Dean points out that he could set him up with one of Brooke’s friends. Dean is coming along too strong with the questions and backs off a bit. Dean has at least started to plant the ideas in his head.
The guys are interrupted by Brooke making her way down the stairs. She’s excited because it’s her last day of this schedule. Her make up is all done up and her upper half is dressed nicely while her bottom half is just yoga pants, but they are very tight, they can see through them and know she isn’t wearing any underwear. Brooke makes her way to her office. Dean hatches a plan and follows her.
Dean had a new idea and this one he could tell Brooke about.
What’s the plan?
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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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