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Chapter 157
by
Jjaymes94
What did Dean see?
An empty room
Dean pushed Richard and the door revealing the guest room. Richard was naked, “Dude” He said. Dean looked around the room, Brooke was nowhere in sight. Dean caught a glimpse of Richard’s long flaccid cock before realizing he was staring. “Uh, sorry.” Dean turned around and exited the room, Richard shut the door behind him.
‘What the fuck just happened’ Dean thought to himself. Why didn’t he investigate more, Brooke had to be in there, right? Why did he just apologize to Richard? What was Richard’s game? He didn’t want to humiliate Dean by fucking Brooke in front of him? Why was he lying and where was Brooke?
Dean pulled his phone out of his pocket to pull up the camera in the guest room. Dean saw that Richard was still standing at the closed door, it looked like he was listening, Dean froze, was he was waiting for him to leave?
Dean decided to walk away towards his own bedroom but he made sure to watch Richard on his phone.
As soon as Dean started walking, Richard moved away from the door. Dean went into his room while Richard went and opened the closet door. Brooke was standing in the closet. Richard pulled her out, she was still blindfolded, gagged and still had her hands tied behind her back. It looks like their fun was about to start up again. Dean shook his head, the closet, of course.
Dean sat on the edge of his bed and watched his phone closely. Was Richard still going to fuck Brooke with Dean in the house.
Richard guided the blind Brooke to the bed and had her sit down, he was being very kind and gentle to her now. He got another piece of fabric and tied her legs together making her completely immobile. Now he was in complete control of her, he could do anything he wanted with her. Richard positioned and bent her body on the bed, she was basically lying in the fetal position. He positioned himself near her ass. Instead of fucking her roughly he slowly penetrated Brooke, making sure she was to feel every inch of his large cock. Brooke’s body quivered more and more the deeper his cock went. Richard was being extremely quiet while Brooke on the other hand was unable to make any sounds.
Dean made himself more comfortable on his bed as he watched Richard fuck his girlfriend for the umpteenth time today. Dean’s cock wasn’t quite ready for another round unlike Richard’s. Dean knew that Richard was going to cum in Brooke again for however many times it is now but couldn’t help think that this was overkill at this point. Richard’s cock had to be sore or at least his balls, cumming this many times in one day had to be unnatural. Dean thinks there has to be a certain point where it just couldn’t be pleasurable anymore. Richard has clearly marked his territory now, Brooke was his fuckdoll and her pussy was his, yet he keeps going, he is like a machine, his testosterone levels must be off the charts.
Dean felt utterly inferior to Richard in this moment.
Dean stared at his phone but his mind reflected on the past month and a half since the Master Plan started.
In Dean’s mind, Richard really did own Brooke, she seemed to no longer be his. Dean and Brooke weren’t dating a very long time before the Master Plan started. They were very comfortable sexually and explored there kinks together almost immediately after they started having sex, but the sex wasn’t immediate. Dean and Brooke went on dates for awhile before they went to bed together like a normal healthy relationship.
Richard and Brooke’s relationship on the other hand started off with a blowjob on day one and extremely escalated from there. Between the blowjobs and sex multiple times a day for almost two months, Brooke by now must have made Richard cum more times than Dean at this point in their relationship.
Dean tried to convince himself that that wasn’t true. ‘There’s no way’ he thought. The lack of sex or any sexual interaction between Dean and Brooke during the Master Plan and the multiple sessions a day with Richard start to add up. Dean felt even smaller if that was possible, Brooke, who is supposed to be his girlfriend, has made his roommate cum more times than him.
Dean let that fact wash over him, how could he have let this happen? He becomes frustrated with himself. He thinks he is dumb for ever starting this plan in the first place. He watches Richard tense up and squeeze Brooke’s ass, he is cumming in her again. Richard strokes his cock while slowly pulling it out of her. He wipes the cum left on the head of his cock on Brooke’s ass.
Dean tosses his phone aside, he’s angry with himself more so than Richard or Brooke.
Dean looks at his phone a couple feet from him. Well maybe not all is lost, he thinks. Richard does leave tomorrow, hopefully he will be gone forever. With Richard out of the picture, Dean can claim Brooke once again. Was he being foolish?
Dean’s thoughts run wild. He decides he needs a shower. He leaves his phone on the bed when he gets up and goes to the shower, leaving him with only his thoughts. He jumps in the shower and lets the water rush over him.
Dean tries bargaining with himself. His thoughts race on, Richard treats Brooke like an object, she will come back once he’s out of the picture tomorrow. Dean feels as if he is lying to himself, frankly he doesn’t know how Brooke feels about the situation at all.
There’s no use, Dean can’t lie to himself, Brooke is going to walk out of his life when Richard does. Dean doesn’t clean himself in the shower, he just lets the water run as he stands there. Coming to terms that he wasn’t enough for Brooke, maybe even go as far as to say that she deserves better than him. Dean just couldn’t provide what Brooke needed.
Dean felt numb.
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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