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Chapter 105
by
Jjaymes94
What's next?
Let the game begin
Brooke crawled towards the boys on her hands and knees. Richard and Dean waited patiently for their little competition to begin. Dean didn’t dare to touch himself in hopes of prolonging his orgasm so he can win, Richard on the other hand had no problem stroking his cock hard in anticipation of Brooke.
Brooke reached the floor right in front of Richard and Dean. She used their knees to help herself up so that she was standing in front of them. She turned herself around so her ass faced them and she took a seat between the two of them, squeezing to fit her big ass.
Brooke noticed Dean still had his pants half on, so she helped pull them down. Dean’s cock didn’t spring to action though, it was still small and shriveled. But Dean could feel the blood rushing to it, he was going to have to try his best to ignore his sexual urges and try to keep his mind on things that were unsexy if he was to win this competition.
Both Richard and Dean were naked from the waist down. Brooke put her hands on their thighs, “Are we ready boys?”
“Can you take your shirt off?” Richard asked.
Brooke didn’t hesitate to strip herself of her shirt and freeing her heavy breasts from her bra. Dean tried to look away but the damage was already done, he started to get an erection.
Brooke sat between the two guys, Richard was on her right side, which happens to be her dominant hand. Dean was on her left, which bodes well for him as she is not very coordinated with that hand.
Brooke grabs a hold of both of their cocks, Richard was already at max length while Dean was maybe at half-erect.
Richard closed his eyes and tossed his head back relaxed and enjoying the pleasure Brooke’s hand gave him as she stroked it up and down. Dean tried to take his mind elsewhere and not think about what is happening. Brooke warm hand squeezed his cock pulling it trying to get it hard. Dean couldn’t help but look, shutting his eyes would only make him feel the sensations better.
Dean watched as Brooke stretched his cock upward coaxing it into getting erect. Brooke head moved back and forth looking between both of their dicks. Dean leaned forward to catch a glimpse at Richard’s handjob.
Richard was already hard so Brooke was able to stroke his cock normally from the start. Her hand looked so small compared to his size.
Dean couldn’t stay soft forever, the constant motion of Brooke’s hand made him erect. It’s a step towards cumming but Dean doesn’t feel close, he mostly is feeling sore from cumming minutes before this.
Dean continues to watch both him and Richard get jerked off, he can’t help but watch. Richard lay back relaxed with his eyes shut, not a care in the world. He might not even care if he wins the competition, he still get what he wanted, to be jerked off by Brooke.
Brooke looks to be going twice as fast with Richard’s cock or that might be because she has to cover twice as much ground considering the size difference. Brooke’s left hand is awkward, there is no rhythm to her stroking, it’s good for Dean. Her right hand on Richard’s cock is doing a lot better, she is clearly better using her right.
Brooke leans over Richard’s cock and spits on it. She then leans over Dean’s and makes a spitting sound but doesn’t spit. Dean knows appreciates that Brooke is on his side for this one.
Brooke is giving it her all to please Richard with a very deliberate lubricated handjob whole Dean is getting an awkward dry wank. Richard has his eyes shut so he doesn’t know that Brooke is cheating in Dean’s favor.
Dean watches and hopes that Richard will come first and hopefully soon that way he can fuck Brooke sooner. Brooke hasn’t looked over to Dean’s cock in a while, her hand slowing down as well as she is concentrating on Richard’s cock.
Dean starts getting turned on by the fact that Brooke is giving Richard an extremely pleasurable handjob while he gets a dry slow tug. He knows that this is a competition but he can’t help but be jealous of Richard, he is getting all Brooke’s attention. Dean’s cock twitched, oh no. He can feel an orgasm starting to come. Just a second ago he wasn’t even close and now he was nervous that he could cum soon. Brooke must have felt the twitch as well, she looked back at Dean with a concerned look and stopped stroking him, resting her hand.
Richard of course decided to stop relaxing at that moment and opened his eyes to look around. Brooke started stroking Dean again to not get caught cheating. Richard spoke up, “Are you going to cum soon?” Dean tried to ignore him. Richard continued, “We could just have a threesome, that way there would be no loser, what do ya say?” Richard grinned. Brooke looked at Dean for an answer.
Dean had to think about it. He obviously didn’t want to lose the competition, Richard would then get to fuck Brooke. But if Dean agreed to a threesome he would get to fuck Brooke but that would also mean Richard gets to as well. Lastly if he doesn’t agree and Richard cums first, he would get free reign of his girlfriend, clearly the best option.
The three scenarios ran through his head, all of them were turning him on.
What does Dean decide?
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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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