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Chapter 28
by
Jjaymes94
What's next?
The next day
Today is the big day, Richard is going to lose his virginity... kind of.
Take Richard’s virginity... anally.
The words pop into Dean’s mind immediately when he wakes up. Brooke has loosely been following Dean’s ultimate plan, so he believes today is that day.
Instead of his alarm waking him up it’s Brooke, she’s got a look to her, she has an idea. She smiles and bats her eyes at Dean, she is so adorable cute.
“Fuck me in the ass?”
Dean’s cock instantly gets hard. They haven’t had any kind of sexual activity together in about 2 days, she’s been a little busy... Brooke takes the look on his face as a yes. She takes the leads and pulls his pants down, his dick whipping out almost hitting in her face.
A thought crosses Dean’s mind... is Brooke only doing this to get her ass ready for Richard’s giant cock...? He figured out her plan. Instead of sucking on Dean’s cock, she spits and strokes it a couple times to lubricate it. Although being used to prepare her ass for something bigger, Dean doesn’t refuse, it’s been awhile since they had sex.
Brooke and Dean trade positions, she lays down on her back and he gets up on top of her. She moves her legs up all the way behind her head, she is extremely flexible. This position reveals her tight asshole, her pussy already gushing wet. She reaches down and spreads her pussy juices down over her asshole fingering herself readying for his cock.
Dean readies his cock lubricated by Brooke’s spit. He slowly pushes the tip of his penis into her ass, she lets out a small moan. Dean moves in and out slowly pushing ever so deeper with every thrust. His cock gets swallowed by her perfect ass, already use to his size that was easy for Brooke. Her ass grips tightly to his pulsating cock.
Dean recently being use to his hand is overcome with the tight sensation of Brooke’s ass and can only last five minutes, he cums as far as his cock reaches into her ass. “Already?” Brooke sounds disappointed, she continues to play with her clit as Dean slowly pulls out his cock. “Sorry I have to get ready for work” he says. Brooke continues to finger fuck herself and pulls out a dildo to replace Dean’s cock in her ass... “You don’t mind right?” Brooke says not really waiting for an answer. Now plunging a large dildo into her ass. “No” Dean answers not really having a choice in the matter and he goes to shower.
He comes back into the room to see Brooke passed out with the dildo between her legs and the sheets soaking wet. Her body glistening with sweat, she gave herself a good fucking. After getting dressed, Dean kisses Brooke’s forehead waking her up a bit, he says goodbye.
While eating his breakfast he can’t help but think about the events that are going to unfold today with Brooke and Richard. He doesn’t want to miss his roommate losing his virginity to his girlfriend. He thinks of a plan.
Dean unlocks the back door and leaves for work, shutting the door loud for all inside to hear. He gets in his car and starts to drive. Dean makes up an excuse and calls out of work, parks around the corner from his house and walks back to his house. He sneaks around to his backyard and checks in through the back door, no one can be seen in the kitchen or through to the living room. It has only been 10 minutes or so since he left so he didn’t expect to see anyone, he slips inside.
Dean can hear the shower in his bathroom running, he assumes it’s Brooke cleaning herself up. He makes his way up the stairs, Richard’s door is shut like normal. Dean decides the best way not to be caught home is to go into the guest bedroom next to Richard’s, no one has any reason to go into there. He leaves the door cracked so he can hear out into the hall. He hopes he can hear through the wall too.
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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