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Chapter 65
by
Jjaymes94
What's next?
The Airport (Main Storyline)
Dean has a lengthy drive to the airport, he eases his mind and his boner by listening to the radio.
An hour or so passes and Dean arrives at the airport, he texts Brooke to let her know he made it to the airport. She doesn’t respond, she was probably still sleeping, resting off her hangover.
Dean makes his way through airport security and to his terminal, he takes a seat to wait for his plane to board. He checks his phone and sees a text from Brooke, he must have missed it buzz while getting through security.
Brooke: Have a good flight!
Dean: I haven’t boarded yet lol I’ll let you know tho
Out of curiosity Dean decides to spy on Brooke, he pulls up the camera in his bedroom. Of course Richard is there. He was standing next to the bed just talking to Brooke while she was laying on here side facing him. Both of them surprisingly fully clothed. Dean grabs his headphones out of his backpack and listens in. He also looks around making sure nobody is looking over his shoulder.
Dean watches as Brooke looks at her phone. Richard asks who she is texting, she explains that it’s Dean. “Forget about him, he’s gone, I’m the man of the house and I make the rules now.” Richard was being cocky again. Brooke still sent the text message. Dean’s phone buzzes and he reads the message:
Brooke: okay!
Dean doesn’t respond and watches while Brooke and Richard interact. Richard asks about Alexa, “So how does she feel about me? Did you get her interested?” Richard is demanding. “Well... she’s coming around, I’m working on it, don’t worry.” Brooke didn’t sound sure of what she was saying. “Try harder!” Richard was being a dick. “Listen I’ll talk to her this week, we could set up another double date again.” Brooke pleads with him. Richard thinks for a bit, “I guess that’ll do, for now.”
Dean overhears that his boarding group has been called, he puts his phone away but keeps his headphone in to listen.
Brooke is telling him what Alexa likes in a guy and what she doesn’t and also why the date didn’t go well and what he could improve on. Richard didn’t take this very well, he seems to think that she is wrong and Alexa should conform to him since he’s the man.
Dean has his ticket scanned and he walks onto the plane. He finds his seat and quickly sits down, his row empty for now. He pulls his phone out and peeks at it making sure no one else can see his screen. He makes a quick text to Brooke:
Dean: boarded the plane, text you when I touch down in FL
Dean quickly looks back at the camera. Brooke picks up her phone, this makes Richard unhappy, “What did I just say about him, forget him, I’m the man of the house now.” Brooke obliges and puts her phone down without texting Dean. “Okay man of the house, now what?” Brooke says in a flirtatious tone.
Dean watches intently.
Richard was taken aback that she didn’t try to fight him at all. He pauses to think for a bit. Brooke is still laying on the bed, she looks up at him waiting patiently, “So more rules? I haven’t done anything sexual with Dean since you told me not to. What now?” She says. “I’ll do anything with you.”
This was news to Dean, he was unaware of this arrangement. He pulled his backpack to his lap to conceal his boner.
Richard finally speaks, “Well first things first.” Richard pulls down his pants exposing his long limp cock. Nothing else was needed to be said, Brooke, still laying down inched to the side of the bed, opening her mouth. Richard moved his body closer to her head and lowered his balls into her mouth, his cock rests on her cheek, Brooke starts sucking away.
“As I was saying...” Richard begins to speak again. He must have noticed the lingerie sprawled out on the bed that Dean bought for Brooke. “...you must only wear this lingerie around the house, nothing else allowed.” Brooke makes an mhm sound while licking Richard’s nuts. Dean watches as he can see Richard dick starting to rise and become hard.
Dean was now joined by a stranger in his row, he quickly puts his phone face down on top of his backpack on his lap, he continues to listen on his headphones.
Richard can be heard talking still, “Also don’t text Dean anymore, he’s gone, he doesn’t exist.” Brooke can be heard saying okay followed by the sound of her moving to suck his cock now.
*slurp slurp*
Richard continues, “And you keep ‘this’ a secret from Alexa” he is obviously referring to himself and Brooke being sexually involved. “I don’t want you ruining my chances with Alexa.” The sounds of Brooke happily sucking his dick ring in Dean’s ears.
“And...” Richard starts to speak.
“Sir” the flight attendant gets Dean’s attention, “Please but your bag underneath the seat in front of you and turn your phone to airplane mode.” Dean nods his head, he puts his backpack away, he pulls at his pants and tries to conceal his boner. He takes one quick look at his phone before putting it in airplane mode. Richard had a fistful of Brooke hair in one hand and his other hand was fondling her breast while facefucking her. Dean turned his phone into airplane mode. That image stuck in his head for his flight. Two hours to think about what just happened and what is to come.
What's next?
Sharing is Caring
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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