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Chapter 68
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I Make a Choice
It was a very hard week for me.
Emma didn’t **** me to make my choice on Monday, but she did want an answer before the Friday night game night. I either had to pull her out of the prize pool by Friday, making her mine and mine alone, or I had to accept that Owen would take her to prom and then take her, in the hotel room after prom. If I couldn’t accept either of those two options, then we were done.
Of course, being done meant that Owen would still get her anyway.
It was surprised at how difficult the decision was, actually. Things had changed so much since I first started tutoring Emma. Then, she had seemed completely unattainable. The mere suggestion that I might some day be dating her, and even having sex with her, would have seemed like the fulfillment of my wildest dreams.
Now, months later, that was exactly what she was offering, and I found myself unsure that it was enough. Emma had shown me a side of myself that I hadn’t known existed. It was confusing and frightening and sometimes painful. But it also turned me on like nothing else I had ever known.
I struggled to come to terms with these strange feelings. I couldn’t really understand why they would turn me on the way they did. My logical mind argued that the best course of action was to leave these seemingly deviant feelings behind forever and enjoy the fact that Emma had agreed to be all mine. She’d had sex with lots of guys, but none of them had captured her heart like I had.
It should have been easy, right?
But desire often trumps logic, especially powerful sexual desire. There is a reason men have gained the reputation for thinking with their penises. Arousal often completely overpowers rational thought and makes us do things that make no damn sense at all.
What kept me from going insane that week was my time with Emma. We were officially dating again, so I took advantage of that and took her out on a date every night that week.
On Tuesday we just went out for ice cream and then took a long walk in the park. On Wednesday it was dinner, and on Thursday it was a movie. She never once brought up our discussion from Monday night. She never once brought up the decision I was supposed to be making. We just talked and held hands and reconnected. It was good to reestablish the fact that we had, in spite of all the drama surrounding our sex life, become very close friends.
When I sat down at our usual table for lunch on Friday, I was reminded that the clock was ticking on the decision I needed to make.
“Isaac,” Ryan said to me with a big smile on his face as he gave me a fist bump, “good to see you man!”
“Good to see you,” I echoed back to him.
It really was always good to see Ryan. He had a way of making everyone feel like they were his best friend.
“Hey Issac,” Grant said looking in my direction as I sat down next to Emma, “the rumor is you’re thinking of pulling Emma from the Prize Pool. That true?”
“It’s true that I’m thinking about it,” I replied.
“That would kind of suck,” Cameron chimed in.
“Yeah,” Ryan agreed, “but good for you if you to. We all support you if that’s what you want to do. Don’t we guys?”
“Yeah sure,” Grant said, “congrats.”
I could tell he wasn’t really all that excited to have one of his favorite toys taken away. None of the other guys really even pretended to not be sad that Emma might not be an option in the Prize Pool.
“So you haven’t decided yet?” Justin asked.
I shook my head.
“Are you going to decide before we play tonight?” Zach asked.
“Yes,” I said.
“You okay with being pulled from the prize pool, Emma?” Grant asked. “Won’t you miss me?”
“As if,” Emma said, teasing him. “I might actually be able to walk on a Saturday morning from now on.”
That brought rounds of laughter from everyone at the table. I noticed more than a few of the girls nodding their heads in agreement. Grant had quite a reputation for being able to stretch a girl out. They seemed to joke about it a lot, alternating between swooning over how big he was and complaining about how big he was.
The lunch conversation put pressure on me to decide what I was going to do. I wasn’t sure I liked the pressure.
It was the middle of the afternoon that I had an idea come into my mind. I was pretty sure it was a really crazy idea, but I had to admit that the thought of it kept me really distracted for the rest of the afternoon. By the time I left to go to Justin’s house for the Friday game night, I’d pretty much decided on a rather reckless course of action, but one which turned me on a lot. I figured I was pretty much equally torn between my choices, so it was as good a method as any to determine my answer.
When we had all arrived at Justin’s place, picked because his parents were out of town for the weekend, Ryan spoke up.
“I’m sure everyone wants to know what Isaac decided about Emma, but before he tells us,” he turned at looked at Justin. “Since it’s your place, you pick the game. What’s it going to be tonight?”
“Texas Hold ‘Em,” Justin announced.
Internally I was grateful for his choice. It meant I actually had a chance to win, which made my plan much more interesting. If it had been a sports related activity, the outcome would have been predetermined before we even started. I knew I could hold my own playing poker.
“So what’s it going to be Isaac?” Grant immediately asked. “Is Emma in the pool or not?”
“Yeah Isaac,” Emma said, smiling at me expectantly, “what’s it going to be?”
I knew she was the only person there that knew that I was deciding on so much more than just the Prize Pool. I wondered what she would think of my crazy ass idea.
“We’re going to play for it,” I announced.
“What do you mean?” Ryan asked.
“I mean,” I said, trying to avoid Emma’s rather intense stare, “that if I win tonight, I will pick Emma, and she will be removed from the Prize Pool for the foreseeable future, hopefully forever. If I lose, however, then Emma can stay in the prize pool as long as she likes. You’re all playing for the chance to keep her in the prize pool.”
There were hoots and hollers around the room from the guys, who loved having a good competition to determine an outcome. They also loved that they were going to get the chance to keep Emma in their pool.
I glanced at Emma. She did not look nearly as happy as the guys in the room.
“Just a second, everyone,” she said standing up and grabbing my hand. “We’ll be back in a minute.”
She dragged me out of the game room where we were gathered and into the kitchen.
“What the fuck are you thinking?” She asked me, clearly much more upset than I thought she would be.
“What do you mean?” I asked.
“You’re leaving out entire future up to chance? One poker game decides the nature of our relationship from now on? How could you be so callous about this, Isaac? I put a lot of thought into how we were going to make all this work, and you’re leaving it up to a fucking game to decide?”
Hmmm. That did feel a little awkward, didn’t it? But I had my reasons.
“It’s not quite like that, Emma,” I said.
“Then what is it like?” She asked.
“I’ve put a lot of thought and effort into this as well, I swear to you that I have. Every day I’ve thought about it. Every night, I’ve thought about it. I’ve weighed the options. There was only one I was able to eliminate.”
She cocked her head to the side questioningly.
“I am not breaking up with you, no matter what happens at prom,” I said. “Or any other time for that matter.”
I could see that calmed her down considerably.
“But no matter what I did,” I went on, “I simply couldn’t decide between the other two options. On the one hand, I really don’t want to give up this new side of me that you introduced me to.”
“The deeply perverted side?” She asked. I could see she was starting to replace her anger with a little humor. It was a good sign.
“Yes,” I said, “that one. But on the other hand, giving it up and keeping you to myself seems like the much more logical choice, the safer choice.”
“Safe can be boring,” she said.
“Exactly,” l agreed. “And I’ve always liked you precisely because you are seldom boring.”
My talking her through my thoughts had changed her demeanor. I think she needed to see that I had actually given her ideas some serious thought and that I wasn’t just recklessly leaving it all up to chance.
“So there’s my dilemma,” I said. “I want both options. And I want them both very badly. So I am simply unable to pick. I finally decided that as long as I was with you, it didn’t really matter which one I picked.”
“Just piling on the shit now, eh?” She said with a smile.
“It wasn’t until this afternoon, late in the day, that I realized I was never going to be able to decide. And that’s when I had this wicked thought. What if I had to win you? Suddenly the thought of playing the game tonight with real stakes turned me on a hell of a lot. Win and you’ll be mine forever. Lose and you will get your pick of men. I have to admit the idea was a huge turn on to me.”
“Because you’re deeply perverted,” she said again. Her smile seemed quite genuine at that point. I guess she had gotten over her anger.
“So I figured, what the hell? Since I’m good with both outcomes, as long as I have you, why not turn tonight into an exciting adventure?”
“Deeply, deeply, perverted,” she said with a sigh, but an even bigger smile.
“Let me turn this back on you,” I said.
“What do you mean?” She asked.
“I’ve already told you that I’m happy with and will accept either choice. That would allow you to be free to choose what your preference would be. I would be perfectly happy with that. Do you want to choose, or do you want to go out there, knowing that I am going to fight like hell to win you forever, and that there will be seven other guys trying like hell to stop me and earn the right to keep fucking you?”
“Mmmm,” she said, “I see what you mean. That is really twisted, in a very delicious way.”
“It makes me hard just thinking about it.”
“Because you are deeply perverted,” she said. “I think that’s already been established.”
“So what’s it going to be? Do you have a preference? Do you want to pick, or do you want me to play to win?”
“Tell you what,” she replied.
“What?” I asked.
“You win and I am going to find the nearest bedroom and fuck you until you simply can’t get it up anymore.”
“I like the sounds of that,” I replied.
“But if you lose,” she said with a long pause, holding it out until she knew I could barely stand it, “then I’m not going to let you have me until after prom night. How’s it going to feel knowing you didn’t get me until after two of your friends had me? Maybe I should fuck Ben and Trent too, so that every … single … one of your friends gets me before you do?”
Oh god!
I probably shouldn’t try to come up with devious little schemes in the future. I think it only encourages her to one up me.
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Beauty and the Nerd
A rose with a thorn, or a cactus with a flower?
The school slut gets involved with the top-scoring nerd. (Main story completed)
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- Slow Burn, Teasing, Femdom, Voyeurism, Slut, Cuckold, Cuckolding, promiscuous woman, Swinging, Humiliation
Updated on May 2, 2025
by white_horse
Created on Dec 31, 2021
by Vox121
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