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Chapter 195
by
Jjaymes94
What's next?
Summer
Dean and Summer talked with each other all the way until the restaurant had to close. He learned about her.
Summer is 20 years old, she is originally from Oklahoma which is quite far from where she is now. She moved here about 2 years ago for a job that didn’t pan out, she didn’t elaborate much on that. She only has a high school degree and since she came to the city for a job she never went to college. She works almost every day and doesn’t have time for much else, she’s just a waitress so she has to work a lot to afford her place. Talking with her Dean can tell she’s a very positive person, she can see the positives in everything. She is also extremely nice and friendly, probably the kindest person he has ever met. Probably not a bad bone in her body. Summer was also raised in a religious household although she doesn’t practice anymore she still holds some of those values she learned.
Dean told her about himself as well, he vaguely talked about Brooke but didn’t tell her the reason why they got a divorce and he definitely didn’t tell her about Richard. Some of Dean’s secrets maybe should stay secrets, after all he couldn’t unload this all on her, they barely know each other.
The restaurant was closing and they needed to leave. Summer wrote her number down and gave it to Dean, “It was so nice hangin' out with ya! How 'bout we plan another date? What do ya say?” She touched his arm while saying this. Dean smirked, “Sounds like a plan!”
Over the next few weeks Dean tried to plan a date with Summer but her work schedule was so hectic that they were having trouble finding a mutual open date. Dean didn’t want to miss a chance with her so he thought of the next best thing, he would go to her restaurant and when she was done her shift they could hang out just like their ‘first’ date.
Dean did this repeatedly over the course of a month, he would sit in her section, have dinner with her as his waitress and then when her shift was over they would chat and hang out until the restaurant closed. It wasn’t the best but it was better than not seeing her at all.
As far as relationship status goes? There wasn’t a label put on it at the moment. Dean didn’t want to rush things with Summer, he knew she was quite reserved and he didn’t want to make her feel uncomfortable at all by being too forward. Dean hasn’t even kissed her yet, they only hug when they say goodbye. He hasn’t even seen her outside of the restaurant… Dean started thinking about the past month with Summer, was he in the friend zone? Was he putting himself in the friend zone? Was he being too slow about this? Maybe he needs to make a move? Dean has gotten too up in his head, this time at the restaurant will be different.
Dean and Summer are on another one of their ‘dates’ just chatting and talking about things with one another after her shift that day. Dean started thinking about whether or not Summer thinks they’re just friends or dating.
“I really like hanging out with you,” Dean says. “Aw, shucks! I sure do enjoy spendin' time with ya too, Dean!” Summer smiles. “So I was just thinking… what is this?” Dean said as he gestured to the both of them. “Honey, what in the world do ya mean by that?” She said in reply. Dean shyly asks, “well, are we just friends?”
“Well, Dean, do ya just wanna be pals? Or is there somethin' more on your mind?” Summer said, she looked at him with such kind eyes. Dean couldn’t take the direct eye contact and looked away, “I’d like to be more than just friends,” Dean said then looked back a Summer. She smiled, “Well, darlin', if that's the case, I reckon it's high time you ask me somethin'.” She says while having a big grin.
“Summer,” Dean pauses and grabs her hand on the table, “will you be my girlfriend?” He asks seemingly nervous even though he is quite certain of her answer.
“Well, sugar, I thought you'd never ask! Of course, the answer is a resounding yes!” Summer said, she leaned over and gave him a kiss on the cheek. They sat holding hands at the table, they were both giddy and excited to start this new adventure together.
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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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