Chapter 199
by
Jjaymes94
What's next?
The Next Step
Dean wanted to take his relationship with Summer to the next level. While he didn’t have control of their relationship sexually, he did know where they were emotionally. The next step could lead to sexual advancements as well, he know what he had to do.
Dean got down on one knee and proposed. “Summer, will you marry me?”
"Oh my stars! I can't believe it! Yes Dean, Yes!" Summer excitedly said.
Dean and Summer were excited for this next chapter in their life together, they were now in love and now engaged.
Dean and Summer were hanging one night as usual just enjoying one another’s company. They were watching a movie that had some sexuality in it, there were some boobs shown and sex scenes but nothing to ****. Dean was thinking about how he was seeing these actresses boobs but not his own fiancé’s. Summer started the conversation out of nowhere, “Are my handjobs good?” She asked. Dean was wondering where that came from, is was not close to their anniversary at the moment. “Yeah babe, of course…” Dean said. Summer was on to him, she could tell he was trying to make her feel good and give a little white lie.“I’m sorry, I know I don’t have the experience,” Summer was being hard on herself. “No no, it’s okay baby really!” Dean said. "I just wanna be the best I can be for ya,” she said somewhat sadly. “Hey it’s okay, you just need some practice that’s all, you’ll get there, don’t worry about it,” Dean said. The conversation stopped there. Dean thought maybe she would initiate a handjob so she could get better but that wasn’t the case. They didn’t talk about it again that night.
A few months later Dean and Summer are in the process of finding a wedding venue and all that goes into a wedding. Summer sleeps over more often but nothing sexually happens. Dean left for work one day that she slept over leaving her in the house by herself. While at work Dean was receiving a call from Summer. He answered it, “Hey!”
“Hey Dean,” Summer said. Dean could hear in the tone of her voice that something was wrong. “Everything okay?” He asked.
Summer let out a sign, “Well, if them shades in your bedroom are open, can your neighbor see on in?” Dean knew his house was close enough to his neighbors that they could see in if he opened the shades but he never opened for that reason, he never told Summer. Dean thought, what did the neighbor see? “Yea I think so… that’s why I just keep them shut…” Dean said nervously.
“Oh shoot…” Summer said. Dean quickly asked, “What happened?”
“Well…” Summer started, “Well when I woke up, it was dark, so I opened them shades to let some natural light in. Then I went and took a shower, dried myself off completely and then left the towel in the bathroom. Saw your big ol’ mirror by the window and couldn't help but check myself out. Then I Decided to do my makeup after that. So I was standin' at that mirror for 'bout a half hour, totally exposed. I looked out the window and saw an older gentleman near his window on the computer facing my direction. I quickly shut them shades. Couldn't tell if he was lookin' or not.” Summer said.
All Dean could think of is Summer naked and didn’t say anything. “Well?” Summer asked again. Dean shook out of it, “He probably didn’t see you, he was on a computer right?” Dean thought she was worrying about nothing.
“But that’s not all…” Summer said.
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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