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Chapter 232
by
Jjaymes94
What's next?
The Months Leading Up to the Wedding
A month passes and It’s gotten a little bit harder for Dean now that it has been just over a month of this new situation with him, Summer and Ron. Dean still tried to kiss and make out with Summer as much as possible but now she gets slightly annoyed with him and telling him that she’s not in the mood from time to time.
Summer has had a decent steady schedule between work, spending time with Ron and spending time with Dean. She sees Ron probably 4 to 5 times a week and Ron fucks her in the ass about once a week on top of countless blowjobs and about everything else you can do without vaginal sex. Since Ron has been about to kiss her now, Summer has been complimenting him in her notebook about how good of a kisser he is. Summer kisses Dean almost every day now, she’s been saying that Dean has been very needy lately so he has reeled back attacking her with kisses every day. Summer and Dean spend 2 days together without distractions but see each other almost every day. Summer spends less and less time at her apartment with Ron and Dean being next door neighbors, she wanted to spend as much time with them as possible.
Less than 5 months to the wedding and Dean doesn’t really know much about it, he wasn’t all that involved with the planning, Summer was in charge of that and occasionally would ask questions for Dean’s opinion. Summer mainly would plan the wedding with Ron since he was the one funding it.
Dean regularly masturbates to keep himself sane. He mostly jerks off to imagining Summer and Ron together, doing only what he wishes he could do with Summer. The thought that really starts to get Dean going is the thought of his wedding night, the thought about Ron taking Summer’s virginity, Dean doesn’t last long after that.
The months go by quicker and quicker. Dean was in a rut. Every week that passed was like clockwork, it was predictable and not varying to any degree. It’s been six months since Dean and Summer struck the deal with Ron, Dean reads the paper they all signed:
What Ron gets:
1. Summer’s Virginity on wedding night.
2. Allowed to Kiss Summer, no limits
3. Invited to Wedding, marries them
4. Invited to Honeymoon, gets Summer for 2 days out of 2 weeks
5. Dean and Summer abstain from anything sexual for 6 months until after wedding, only kissing allowed.
What Dean and Summer get:
1. Wedding and Honeymoon Paid for >$100,000
2. Summer’s debt paid off
3. Summer gets a full time job, pays $75K salary
4. No more lessons, sexual contact between Summer and Ron after honeymoon.
“It will all be worth it,” Dean talks to himself. It’s been six months of **** for him, in a way. Dean has been able to kiss and make out with Summer for the past six month but that’s it, it’s better than nothing. Having Summer around, strutting her amazing body and knowing what she was doing with Ron the whole time was the real ****. Dean hasn’t seen Summer naked since the beginning either. Dean just has to remind himself of the deal, the last six month will all be worth it.
Dean reads over the section of what him and Summer will get. Wedding and honeymoon paid for, Summers debt paid off, Summer gets a full time job… Dean really was setting themselves up for a good future, a bright one, they would be debt free and have great jobs going forward. The last part of the deal was selfishly Dean’s favorite part, Summer and Ron would be done all sexual contact after the honeymoon, Dean would be about to rid his marriage of Ron and they would be able to be a normal couple.
And just like that… it was the night before the wedding…
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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