Page 167 of Prized Possession

I kneel down beside his head, making sure he can see me through the tears that are streaming down his face, mingling with snot and sweat.

“Make sure you relax. It really does help if you push against the cock. It’ll slide in much easier. You don’t want us to rip your arse this early on.

“Even if you’re bleeding, the fuck machine will continue, it’ll just be fucking excruciating for you. So, do yourself a favour, be a good fucking whore and let the dick in.”

I make my voice as taunting as I can, knowing whatever he said to Chloe would have been so much worse.

Jake chuckles as he loudly says, “What a fucking cock whore, he’s letting the dick in. I bet he’s done this before.”

I open my eyes wide, making an exaggerated gesture just for Frank. “Is thattrue? Have you had a big dick in your arse before? Is that why you rape women, because secretly you wish you could fuck guys instead?”

Frank tries to shake his head, but the tip of the dildo must have finally breached his rim as he lets out a scream.

“Stop,” he mumbles beneath the tape. It’s the only word I can clearly make out.

“How many times did Chloe ask you to stop? How many times did you ignore her?” I snarl, watching as Jake moves the machine, pushing the dildo further into Frank, who groans.

“It’s in,” Miles announces.

“Now for the fun part,” I tell Frank, before nodding to Jake to turn on the machine.

It starts slowly, rocking back and forth, no more than an inch, letting him get used to the feeling of being stretched out, which is more than he deserves, but we have a plan.

Jake then increases the speed, adjusting the settings, so that the dildo now pulls almost all the way out before thrusting back in, hitting Frank deep. Each time it does, he’s pressed against the table, his dick getting squashed against the edge.

After a few minutes like this, we see the moment it stops being painful for Frank, and the dildo begins dragging over his prostate, giving him pleasure. His eyes widen and his cries of pain turn to whimpers of enjoyment, which was our plan all along.

“Are you enjoying this? Does it feel good having a cock deep in your arse?” I ask tauntingly.

“I bet his tiny dick is rock hard. The little cock slut clearly loves having his arse filled,” Jake adds.

Miles chuckles. “Now he finally knows what a real man’s dick feels like. I bet if we were to remove his gag, he’ll be begging for more.”

We deliberately set the machine so he’d enjoy it, but it’s not going fast enough or deep enough to get him off. It’s just touching his prostate, not massaging it the way he no doubt wants it to.

The company we bought the machine from gave us a lot of help with this, no matter how embarrassed the three of us were when we asked about how to use it.

“Shall we take the gag off?” Jake asks.

I lean in closer to Frank. “Listen to me, cockslut. If I take this gag off, and you complain once, I’ll replace the dildo you have now with one twice the size. Do I make myself clear?”

Frank nods, and out of the corner of my eye, I see Miles’ brow raise in question. We don’t have a bigger dildo, but Frank doesn’t need to know that.

Jake reaches over and yanks the tape off, making sure it hurts. Frank screams before quickly clamping his mouth shut, biting on his lip as his eyes roll, and I know he’s trying to stop himself from making any noise.

“You don't need to keep quiet, cockslut. We want to hear how much you’re enjoying having your arse raped,” I taunt, a devilish smirk on my face.

“Tell us, does it feel good? Are you becoming a filthy whore for cock?” Jake asks, his voice just as mocking.

“Yes,” Frank whispers, making all three of us laugh.

“Is it making your little dick hard?” Miles asks.

Frank moans, closing his eyes as he gets lost in the sensations. “Yes, but it hurts as it’s trapped against the table. Will you…”

His words trail off, replaced by a loud groan when the machine hits a particularly deep part of him.

“Will we, what? What do you want, you dirty cock whore?” Jake snarls.

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