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Chapter 27
by
Jjaymes94
What’s the plan for tomorrow?
Sex
The only logical next step is sex, Richard is going to finally lose his virginity. Dean specifically remembers what he wrote down because it was a little fucked up.
Take Richard’s virginity... anally
What’s more kinky then his first time having sex being anal and not in Brooke’s pussy. That’ll be some experience. Dean’s shorts tighten just thinking about it.
Dean can’t help but smile, he looks over a Richard sitting on the couch, he has no idea that Dean knows about his affair with his girlfriend or the fact that he is orchestrating the whole thing and lastly, what is in store for him.
Dean runs upstairs before Brooke returns from her home office and leaves Richard in the room by himself. Dean can’t help himself, he needs to jerk off. It has become a regular thing now, a routine if you will. Every time he pictures his girlfriend cheating on him with his roommate he has to immediately jerk off, almost five times a day, his dick is it extremely sore all the time but he needs his release. Instead of jerking into the toilet he finds a pair of Brooke’s dirty panties to receive his spunk. Being that it is the numerous time today, it takes a little longer than normal.
Being gone upstairs for quite sometime, Dean wonders if Brooke and Richard are up to something naughty... when he went upstairs Brooke was still in her office and Richard was in the living room.
Dean sneaks his way to the stairs past Richard room, the door is closed now he tests the handle but not enough to alert if anyone was inside, locked. He wonders if Richard is actually in there... he peers into the living room. No one is there. Dean makes his way down the stair, they creak, it takes several minutes to get down the stair without making much noise, his penis sorely twinges with each step, it can’t take another beating. Making his way through each room downstairs he doesn’t know what to expect, the TV is still on. Dean walks to the kitchen, no one there either. He checks the hallway, he can see Brooke’s office door is shut, he approaches checking every room on the way. The bathroom door is open, nope... the laundry room, nope... the last place they can be is her office... unless Richard is actually in his room. Dean listens at the door.
“You said you’d be fast... I love sucking your dick but Dean could be down any minutes” Brooke is whispering.
Dean hears a faint slurping sound. Brooke is trying to be as quite as possible.
*slurp*
Dean tries to peak underneath the door. He can see Brooke’s calves on the floor and Richard’s feet, she’s kneeling in from of him sucking his cock.
Richard can be heard whispering, “This is the fourth blowjob today, trust me I’m not holding out, I’m trying.”
Fourth.
Brooke’s become a slut for his cock.
*slurp slurp slurp*
“I’m gonna cum.”
Dean hears a muffled moan. Afraid of being caught listening in he makes his way to the living room and plops on the couch.
A couple minutes later he can hear the door open. Brooke walks out looking around probably to see where Dean is. They make eye contact. Richard is not seen. “Hey Dean,” Brooke says with a little surprise. Then she sits down next to Dean.
She starts to rub his cock, “Want to go upstairs and have some fun?” Dean isn’t falling for her trick, between his worn out penis from himself jerking off and the fact she was trying to get them to go upstairs so Richard could sneak into his room, he wasn’t going to comply. Dean moves her hand off of him, “I’m okay, I’d like to finish this movie.” Brooke rolls her eyes, “okay.” She gets up and heads to her home office and a minute later comes back. Dean guesses she was telling Richard it was going to be awhile. This time Brooke sits on the opposite side of the couch.
Over an hour passes and the movies over. Dean is happy with himself. He felt in charge again because he made Richard stay in Brooke’s office for the rest of the night. Brooke unaware that Dean knows.
Dean grabs her hand and pulls her upstairs, time for bed. Getting ready for bed he can only imagine Richard sneaking back up to his room, he chuckles at the thought.
Nothing happens tonight between Dean and Brooke, which is pretty unusual in there relationship but they drift off to sleep, tomorrow is a big day.
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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