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Chapter 178
by
Jjaymes94
Who?
Leave it up to chance
Dean thought about it for a moment before saying, “Why don’t we leave it up to chance?”
“By chance?” Brooke said curiously, “how do we do that?”
“Like a game of chance… where the game will decide for us and we have to do what it says…” Dean says still nervous of what Brooke thinks of this new idea.
“You know of a game like this?” Brooke asks. Dean has peaked her interest.
“Yeah I was on the internet and I came across this website, it’s called fap roulette!” Dean says now with some excitement in his voice.
“Fap? What is that?” Brooke asked. “It means masturbating,” Dean explained. “Oh I see,” Brooke said with a smile, “So can you explain how it works?” She asked.
“Why don’t I just show you, let go on the computer in your office,” Dean says as Brooke follows him downstairs to her office computer.
Dean sits down in the office chair while Brooke leans over his shoulder. He types in the website and hits enter. “So this website is sort of like fantasy and sometimes not realistic… like people make up these scenarios and people don’t usually do them, they just masturbate to the thought of it… you’ll see when I show you.” Brooke’s eyes scanned the screen when all the words popped up, studying them. “So these are the categories you can pick from…” Dean says to Brooke. “Such as Anal, blowjob…” Dean starts saying before Brooke interrupts, “oh I love blowjobs!” Dean continues, “Yeah and cum lovers…” Brooke interrupts again, “That’s me!” She giggled a little bit. “Can we pick one of those categories?”
“Well not exactly…” Dean says. “Well why not?” Brooke copped a little attitude. “Because it’s not what we’re looking for…” Dean scrolled down a little, “We’re looking for the cuckold category because that is what we want you to do to me, you’re going to have all the fun while I watch or whatever this tells me to do.” Dean explained. “That makes sense…” Brooke eased her tone.
Dean clicked the cuckold category and scrolled down which brought up a bunch of pictures with words on them. “So some of these can be tame while others can be an ****, here let me show you.” Dean scrolled and clicked on a picture which made it larger.
The picture is of a blonde naked on her knees with a cock completely down her throat with words written on top. Numbers in the top right start to randomly generate.
“See the numbers in the top right Brooke? They correspond to the tasks in the picture, they are random and you’re supposed to follow them.” Dean says.
Brooke looks at the numbers then at the picture, “So in this instance… the first questions is… ‘who does she choose?’” She asks, Dean shakes his head yes. “And the first number is 3… which the answer says… ‘hot guy at the gym?’” She asks again. “Correct!” Dean says. “These plenty of hot guys at the gym,” Brooke giggles. Dean ignores her comment, so look at the rest of the numbers and tell me what it would be if we did this.”
“Okay,” Brooke says, “So I choose a hot guy at the gym… what we do is ‘she gives him a blowjob’ oh wow… what you do is… ‘you’re not there but receive humiliating texts and photos’ hehe and then we go… ‘to a bathroom’ where he cums… ‘on my tits!’“ Brooke finished reading the picture, “Wow that was exciting! What else do we have here?”
Brooke hit Dean’s hand off of the mouse and took control. She randomly clicked a couple different ones and started reading them. “Now don’t forget some of these can be a little too ****…” Dean warned her.
Brooke kept clicking different ones and made comments and questions along the way. “Gangbang? This one picks what I wear… what kind of protection? Different sex positions… this one has a length of time? A year? Wow… you do embarrassing things… bi temptation… this one talks about ovulation? Pregnancy? Wow you are right, there are some **** ones, how are we to choose?”
What kind of challenge do they choose?
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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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