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Chapter 191
by
Jjaymes94
Now what?
Leave
“I need you to leave,” Dean said. He pulled up his pants and walked away from Brooke who was on her knees still.
“What?” Brooke said.
“I need you to leave my house and take your baby with you. We’re done, this is over.” Dean said. He went to his closet. “You’ll have a week to get everything out of this house and when I come back you better be gone.”
Brooke and Dean argued for awhile but nothing would change his mind. By the time they stopped arguing she was no longer furious. Brooke was more calm, more so sad. Dean thinks she has now seen the error of her ways and maybe understands. He packed a bag and decided he was going to leave town while she got her things together from the house. Dean wished her all the best.
Dean drove aimlessly, not really sure where to go or what to do. He felt a sort of weight lifted off of him but was still nervous of what his future held. He drove a couple towns over before realizing he was hungry and needed to stop somewhere to eat. Dean stopped at the first food place he saw, it was named ‘Tap That’ it was a restaurant and bar.
Dean opted to get a table as opposed to sitting at the bar. He sat there and looked around, the place was pretty dead, not a lot going on. Dean had a lot going on in his head. A random waitress came up and introduced herself and asked what he wanted. Dean was too distracted to even bother to look up and grumbled about not looking at the menu and asked for some whiskey. The waitress left him alone and Dean went on his phone, if he was going to not be at his house for a week, he had to make arrangements with work and where he was going to stay. He emailed work so that was covered.
The waitress brought back his whiskey, Dean still didn’t pay attention to her. “Did you get a chance to look over the menu?” She asked him. Dean a little frustrated raised his voice, “No I didn’t look yet…” Dean looked up for the first time since he entered the restaurant and saw his waitress for the first time. Dean’s waitress was a beautiful blonde with the most innocent face he’s seen, she looked like she was college aged. Dean couldn’t help but look down her body, her breast were hidden under the shirt she was wearing but it got tight right at her tits so you know they were large. She looked to be standing about 5’2” and her name completely slipped Dean’s mind since he wasn’t paying attention when she introduced herself in the beginning of dinner. He quickly apologized for the small outburst, “Sorry… it’s been a long night.”

“Don’t worry sweetie, just wave me down when you are ready,” she said. Oh and she was nice and sweet too, Dean thought. He watched her walk away, and a nice ass to go with everything. Dean looked down at the menu to decide what to get while subconsciously spinning his wedding ring.
Dean eventually comes to a decision and looks around for his waitress, he sees her at the bar collecting drinks for another table and he waves her down. She smiles and puts her pointer finger up signifying she will be with him in a minute.
Dean’s waitress arrives after a minute and pulls out a pen and paper, “So what can I get ya?” She says with a smile. Dean tells her his order and she goes on his way, Dean checks her out as she walks away, she really is cute.
Dean sat on his phone and wondered where he would stay for a week, there was a hotel he could walk to from the restaurant he was in, maybe he could stay there and maybe get to know his waitress some more. She comes back a half a dozen more times to bring him food and refills on his drinks. At this point it was too long into the night to ask her her name and she didn’t stick around at his table long, always running back and forth even though the place wasn’t that busy.
Dean sat there for quite some time, so long in fact the waitress came up to him. “I’m sorry darlin'. It's been mighty nice havin' ya here but my shift is done, you can get more drinks at the bar if you’d like.” She hands Dean the check and leaves once more. Dean looks at the check to see if he could find her name on the bill but it doesn’t say.
Dean takes out cash and includes a nice tip and waits for her to come back. The waitress comes back, “I’ll be back with your change…” Dean interrupts, “Keep the change!” She smiles, “Why thank you sir.” She starts to walk away, Dean blurts out, “Want to join me for a drink?”
"Oh, thank you kindly for the offer, but I must politely decline. I'm only 19, you see. Have a good night sir.” She said. Dean watched her walk away for the final time. Dean decided to book a hotel room at the place pretty much next door for the week while Brooke moves out. He may have been turned down for a drink but that doesn’t mean he can’t get to know her during this week.
Dean got more drinks at the bar and got pretty drunk before he headed over to the hotel for the night.
What's next?
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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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