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Chapter 64
by
Jjaymes94
What does Dean wake up to?
A text message
A text message wakes Dean up, he checks the clock, it about 2am. The text is from Brooke’s phone but it is Alexa.
Alexa: hey it’s Alexa, Brooke got really drunk, her phone died so I drove her car and she is staying at my place tonight.
Dean doesn’t bother responding, he’s just annoyed that he didn’t get it in tonight. He falls back to sleep.
Dean sleeps in pretty late, he checks the clock it’s almost noon. The lingerie he bought Brooke is sprawled out in her side of the bed, he flips the covers over them in disgust. He sits up at the side of his bed and checks his phone again, nothing. He doesn’t have lots of time, he has to pack and get ready to go to the airport this evening.
As soon as Dean gets up to go to the bathroom his phone rings. He turns around to go answer his phone, the caller ID is Brooke.
“Hello?” Dean answers. “Hey can you pick me up, I don’t feel well.” Brooke whines on the phone. She also explains that she needs Dean to drive Alexa’s car to her and then drive her back home in her car. Dean doesn’t understand why they can’t just come and get Alexa’s car. Brooke just says please, Dean caves.
Dean doesn’t rush but gets dressed and ready to go. Brooke sends him a text with Alexa’s address and her car keys should be on the table by the front door. Dean locates the keys and plugs the address into his phone for directions. Alexa’s house is about 20 minutes away.
Dean arrives at Alexa’s house with her car, he shoots Brooke at text that he’s here and leaves the car to give the keys back to Alexa. A minute later Brooke emerges from the door she gives Dean her keys and takes Alexa’s keys. She tells Dean to go start the car, Brooke closes the front door on Dean. Alexa didn’t bother to come to the door.
Dean starts the car and waits for Brooke. She eventually comes out wearing the clothes she wore yesterday, her hair was a mess and had makeup smeared on her face. Brooke looked like she was taking a walk of shame right now. She greets Dean and thanks him for picking her up. She shuts her eyes, she clearly doesn’t feel well. Dean drives them home I’m silence.
Arriving home Dean wakes up Brooke who fell asleep in the car and helps her get inside.
Richard is sitting in the living room but doesn’t pay any attention to Brooke and Dean coming through the door. Dean helps Brooke up the stairs and into bed. He lays her on his side because her side of the bed is occupied by the stuff he bought her yesterday. Brooke closes her eyes to try and sleep off her hangover.
Dean quietly packs his things for his business trip he will be on for the week. He makes sure not to forget his porn that he bought yesterday, he peaks at Brooke to make sure she is still sleeping and not looking at what he’s doing. Dean’s dirty mind gets the best of him and takes some of Brooke’s panties that were in the hamper. He goes into the bathroom to collect his toiletries, he makes sure to pack tissues and moisturizer too. Satisfied that he has packed everything he carries his luggage out of the room.
Dean makes his way down the stairs to put his luggage by the door. Before Dean could make his way back up the stairs, Richard stops him, “Where are you off to?” Richard asks. “Upstairs?” Dean is confused. “Duh, no where?” Richard puts to the luggage. It slipped Dean’s mind that he didn’t mention it to Richard. Dean explains he has a business trip for the week in Florida and will be back Friday. Richard says, “Don’t worry I’ll keep the fort down.” He smiles. Dean didn’t like that comment and the grin that followed. Dean continued up the steps. He didn’t have much time before he had to go to the airport so he wanted to spend some time with Brooke.
Dean entered the room and Brooke was still asleep on the bed. He had some time to kill so he sad down next to Brooke and looked at his phone, checking every so often if Brooke had woken up.
Growing tired of this and the fact that he had to go to the airport, he gently rocked Brooke awake. Dean tells her he has to leave now for the airport. “Already? Aw I’ll miss you, have a good trip.” Brooke’s eyes can barely stay open. “Good bye Brooke” Dean says and gives her a kiss on her forehead.
Dean goes downstairs and says goodbye to Richard. Richard gives a wave. Dean leaves his house. He won’t be back for an entire week. His mind runs wild with ideas of what is going to happen here while he is gone. Will this week help or hurt his master plan. Dean will just have to wait and see. His pants have become tighter, he can’t take care of that now. He gets in his car and drives to the airport.
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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