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“Why don't we make this game of ours more interesting?”
Pine looks up from a wordless study of his cards and demurs with a wry smile. “I don't have any money that isn't yours.”
Roper scoffs. “Who said anything about money? Money's such a dull thing to bet with, and besides I don't need any more of it.”
“Then what?” asks Pine, incautiously taking the bait.
“If I win,” says Roper, reeling him in, “you’ll fuck Jed.”
The moment of blind panic is beautiful, but it's only on his face for a split-second and when it has passed Pine has polite, amused confusion in its place instead. “If you win?”
“Yep. What do you want if you win?”
“Your house,” says Pine. It’s clear from his expression that he has decided this is all just a joke and nothing to worry about after all.
Roper nods. “Alright, my house if you win, sex with Jeds if I win. Agreed?”
The answer comes with a smile; “Yes. Don’t worry, I'll take good care of the place.”
Roper expects to win the game and, as usual, he does. The bet goes unmentioned after that, because one of them thinks it was only a joke.
It wasn't, though.
Three weeks later Roper calls in the debt.
“She's having one of her naps,” he explains when Pine follows him into the bedroom, still pretending to be loyal with his every step. “Don't worry about making noise, you won't wake her. Dead to the world. Aren't you, Jeds?” He adds the question in a much louder voice, getting not even a mumble from her in response. He turns back to Pine. “See?”
The other man looks more worried than he's supposed to be and much less worried than he should be. “Are you sure she's alright?”
Roper's reply is dismissive. “Oh, she's fine. She does this at least once every few months - takes a few extra pills to get away from the world for a while. I thought we could take this as an opportunity to settle our debt.”
“What debt?” He really doesn't remember, just as Roper expected.
“Come on, man, you can't have forgotten, it can't have been more than a fortnight ago, maybe a month. We were playing cards, we made a wager, you agreed that if I won you'd fuck Jed. I won and now I want you to fuck her.” He says all this like it's a perfectly reasonable sequence of events that only an idiot could fail to follow to its logical conclusion.
In some ways it is, but only if that idiot has misjudged the depths to which Richard Roper will sink, in which case the error needs to be swiftly corrected.
“But she's not awake,” objects Pine.
Roper shrugs. “Best time for it, if you ask me. You're not really her type,” he adds, lying spitefully. He nods towards the bed. “Go on, get to it.”
“But -”
“You owe me,” he says, dangerously softly. “We made an agreement and you're going to see it through. Otherwise I'll call Frisky in to see if he can find some way to convince you. One that you'll survive just long enough to allow you to keep your promise.”
In that moment, Pine finally spots the trap he walked onto three weeks ago.
“Just pay up,” says Roper, his voice now reassuring, “and you'll be forgiven. I like you, I don't want to have to kill you over something as trivial as this.”
He hadn't been a hundred percent sure about which way Pine would jump when confronted with this choice, but he's pleased to discover that he was right: with a carefully calm expression Pine takes off the jacket of the expensive suit Roper paid for and asks, “Are we going to tell her when she wakes up or is this something I shouldn’t mention next time I'm talking to her?” He unbuckles and removes his belt with hands so steady that Roper is genuinely impressed by his acting skills.
“I suppose that depends how much of an impression you make. Are you leaving the rest on?”
He shrugs. “Why not? I don't want to waste too much time on this.”
“You think sex is a waste of time?” Roper knows damn well that Pine wants to get this over with quickly and he's going to make him work for that privilege.
“That depends who I'm doing it with and whether I want to impress them. Have you got a condom?”
Shaking his head, Roper answers. “She’s on the pill and I had you checked out when I was paying your hospital bills.”
“Alright “ Pine gets onto the bed and Roper wonders if he's hoping for or even expecting a reprieve, a last-moment halt to a test of loyalty before he actually has to cross the line he's being made to walk over.
Roper gives no such pardon, staying unyieldingly silent until Pine is halfway into Jed's cunt and losing an obvious struggle to be just as quiet as Roper has been until now.
“Good?” he asks, to make Pine admit it.
The only reply is a quick glance in his direction and a curt nod, so Roper pushes again.
“Wet enough?”
“Yeah.” Pine puts his hands on the mattress and holds himself up with them as he starts to fuck Jed properly, panting with the effort of the quick, hard thrusts. He's racing through the task on purpose and when he closes his eyes to block some of it out Roper shows his capacity for mercy by not telling him not to.
Jed of course says nothing, oblivious to the power struggle being played out over, and with, and inside of her body.
After what seems to Roper like no time at all but probably felt like half an eternity to his wayward protege, Pine's thrusts grow erratic and then suddenly stop, a low groan as he comes one of the few sounds he hasn't been able to hold in through all of this.
Not bad, in Roper's opinion. It must have taken an impressive level of control to remain that quiet, never mind all the rest of it. He hasn't given up on Pine yet; the man's too good at too many things to be discarded without an attempt at rehabilitation. He can be brought to heel with enough discipline, Roper is sure of it.
Pine is kneeling on the bed, still between Jed's legs but not inside her anymore. His eyes are fixed on her cunt and there's tension in every part of his body. Hopefully he'll have learned his lesson: fucking with Richard Roper is a fool's game and the fool always loses.
“Put your cock away, man, we've got business to attend to. You've had your fun, now it's time to work.”
For just an instant Pine looks like he's about to kill Roper, and it's glorious. That kind of hatred isn't easily won, but Roper is the kind of man who tends to win and he has just ensured that Pine won’t ever forget that.

MidgardianLoser Fri 24 Oct 2025 03:02AM UTC
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Pornasquita Fri 24 Oct 2025 03:42AM UTC
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