Page 166 of Prized Possession

Miles gulps, and the tension in the air quickly grows. I look between them, not entirely sure what I’m witnessing, but it feels like something I shouldn’t be a part of.

When neither of them says anything, I clear my throat awkwardly, and that’s enough for them to both spring apart, looking a little uncomfortable.

“We don’t want it to be pleasurable,” I say, just because the silence was becoming too fucking deafening.

“I know that,” Jake snaps, glaring at me.

“So, what? It’s just a case of parting the guy's cheeks and letting the machine do the rest?” Miles asks, and we both look to Jake, since he’s the one who knows the most about the machines.

Jake shrugs his shoulders.

“Honestly, I’ve got no fucking clue. Porn doesn’t really show a lot of the prep work. I’d assume we need to get him into position, hold his arse cheeks open, and then ease the head of the dildo in. Then the machine can do its job after. Getting the head in will be the hard bit.”

Me and Miles look at him with disbelief on our faces, and he flips us off.

“It’s common sense. I’ve fucked girls in the arse before, and getting the head in is always the hardest bit. Once it’s in, everything is fine after that. With this guy, it will be even tougher, as he’s not exactly going to be cooperative and do all the things we tell girls to do when we’re pushing in,” he adds.

I nod as I take another swig. “He’s right. Getting his arse to loosen up enough to let the head in isn’t going to be easy. If we were doing it to a girl for fun, we’d prep her fully, stretch her out with our fingers, and she’d do as we say when we tell her to push back against us and relax as we first enter. None of that counts here.”

“Thank fuck,” Miles says, breathing a sigh of relief. “I thought one of us was going to have to stretch his arsehole, and that did not appeal.”

“So you don’t like having your fingers in someone’s arse?” Jake asks, his tone much more flirty than it should be.

“Erm…I-I… I mean… I have, it’s just?—”

I take pity on Miles trying to splutter out a response and cut him off.

“He just means he doesn’t want to do it on this fucker, not that he never has or wouldn’t. Now, shut the fuck up, stop annoying each other, and help me come up with a plan.

“If we rip this guys arsehole open too early, we won’t get as much satisfaction out of this. We need it to be pleasurable for him.”

“So we use lube,” Jake says with a shrug of his shoulders, before an evil smirk spreads across his face as he adds, “We just don’t tell him.”

“Someone still has to get the dildo into his arse though,” Miles adds, and we all grimace.

“I think, if it’s lubed up, the person could just spread his arse cheeks and push slowly, wiggling it around a bit if he tries to resist,” I state, looking between my friends.

“So, how do we decide who gets the honour?” Jake asks, sarcasm dripping from his words.

“Let’s do it how we always do. We’ll play a round of poker. Losing hand has to do it,” I suggest, and both my friends agree. Though we’re all quick to point out that none of us actually want to do it.

After a very intense game, we’re ready to show our cards. Each of us slowly turns them over, and my heart is beating out of my chest. I don’t have the greatest hand, but I’m hoping it’s enough.

Once all of the cards are down, I breathe a sigh of relief as Miles groans loudly. I only just beat him, but it’s still a win.

“Motherfucker,” he snaps, slamming his hand down over the cards.

Jake chuckles. “Don’t worry. Think of this as a good thing. Learning how to be gentle as you fuck someone’s arse will come in useful in the future, I’m sure.”

Miles looks like he’s about to throw his bottle at Jake, so I cut in.

“So, we’re agreed on the plan?”

They both mutter their agreements, no matter how unhappy Miles is, and as we finish our drinks, we look forward to putting the plan in place.

I’m pulledout of my daydream by Miles swearing and chuntering under his breath. Just because Jake thought it would be funny, Miles is wearing a pair of bright yellow cleaning gloves as he parts Frank’s arse cheeks just enough for Jake to push the machine in closer.

When Frank feels the tip of the dildo at his hole, he freaks out even more, screaming into the tape, trying as much as he can to thrash around, even though he can’t move at all.

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