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Chapter 108
by
Jjaymes94
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Dean can’t sleep
Dean laid in bed with his eyes shut trying to get some sleep. His thoughts kept him awake, in addition to the moans coming from down the hallway. He tried his best to ignore the sounds, he even tried holding pillows to his ears, they only helped a little bit. The pillows couldn’t block this thoughts that ran rampant with ideas of what Brooke and Richard were doing.
Dean gets Brooke back once Richard cums, but the problem was how long it was taking for him just to cum once, he has incredible stamina.
An hour or so passed and Dean still can’t sleep. He hears footsteps approaching his door. He kept his eyes shut to pretend he is sleeping. He hears the door open and then the heavy breaths of Brooke and a closet door opening. Dean peaks his eyes open to see what Brooke was doing.
Brooke was completely naked and out of breath looking for something in her closet. After a few moments Brooke found what she was looking for. Dean watched as Brooke pulled out a blonde wig and put it on. She stopped at a mirror to make sure it was on straight. Richard must have wanted her to wear it to pretend she’s Alexa. Brooke quickly exited the room again to rush back to Richard.
Dean thought their sex session would be over by now but he was wrong. He tried to sleep again but he laid awake restless.
Another hour passes and it’s eerily silent in the house. Dean just noticed the absence of moaning and wasn’t sure how long it’s been like that. Surely Brooke would be coming back to bed soon now that it seemed to be over. Dean thought there would be a chance she doesn’t come back but that wasn’t the rules of their little contest.
Minutes go be and Dean hears the door to his bedroom slowly creek open. It’s dark but his eyes have adjusted, Brooke is sneaking in the room as quiet as can be. Of course she thinks Dean is sleeping since it’s the middle of the night. Dean watches as his girlfriend takes off the blonde wig and drops it on the ground. She then slowly makes her way to bed, still completely naked. Dean’s penis rises to the occasion, not the best time.
Brooke carefully gets in bed to not shake the bed. She laid on her side facing away from Dean. Brooke had a long night of fucking.
Dean rolls over towards Brooke pretending to still be sleeping. He cuddles up against her, spooning her. He can’t help but feel how sweaty she was, he felt her clammy skin against his. She smelled of sweat as well, not just her sweat but a manly sweat as well, she did not smell good. Brooke reeked of Richard.
While Dean spooned Brooke he pushed his hard cock up against her butt. Brooke now definitely knew he was awake. Dean started to hump more, he didn’t care that she just had sex with Richard, he still wanted her. Brooke didn’t seem to mind she just laid there and accepted it.
Dean started to get more handsy with her, they both knew where this was leading. Before things got too far, Brooke interrupted, “No Dean wait.” Dean of course got a little frustrated, “Why?” Brooke paused and then said, “He just came in my pussy.” Brooke’s words lingered for a bit as they both were silent as if thinking about their options to go from here. There was a long pause. Before Dean said anything, Brooke broke the silence and continued, “You can fuck me in the ass, if you want.”
Those words did it for Dean, he was rock hard now. He gathered some saliva in his mouth and spit onto his hand he reaches down to massage Brooke’s asshole and lubricate his penis. Brooke just laid there waiting. Dean fixated himself, lining up his penis with Brooke’s ass. He presses the head in with ease, there wasn’t much **** needed. Dean groaned, it felt so good to have sex again, although not in her pussy her ass was good enough.
Dean slid his cock all the way in until he was balls deep, it was relatively easy. He started to fuck her ass, starting slowly and building up pace as he went. He couldn’t help think about how easy he slid in, Richard must have fucked her in the ass before him. Instead of deterring Dean, he fucked her harder. Brooke laid still and quiet, letting him do all the work.
Dean didn’t last long considering the last time he had sex. He pumped his full load into her ass. Dean pulled out and laid on his back catching his breath. Brooke rolled onto her stomach, “Good night Dean.” She wanted to sleep.
Dean was happy, a smile grew on his face, he got to have sex with Brooke again.
Brooke fell asleep with Richard’s cum in her pussy and Dean’s in her ass, not to mention she licked up Dean’s cum earlier. She had a productive night.
Dean could finally get some sleep.
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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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