Not a chance

Darryl frowns at your proclamation, but only briefly. "Fine," he grumbles, then snatches the condom back up. A few seconds later, it's securely in place over his cock, and he is once again lining up to enter you. This time you don't stop him, instead you moan softly at the glorious feeling of finally being filled again. Darryl seems equally happy. "Oh, fuck, Cindy!" Accurate.

Once he's fully inside, he leans down to kiss you again, and you respond in kind, wrapping your arms around his neck. He begins fucking you properly now, but slowly. Almost intimately. Oh, fuck, he's not developing feelings for you or anything, right? That could complicate matters. He can't hold himself back for long though, and soon speeds up. On any normal day his somewhat erratic thrusts would have left plenty to be desired. After such a long dry spell, though, they're more than plenty to get you worked up.

Your hands wander down his back to cup a feel of his ass, while his movements are getting faster and faster and your kiss is getting more and more passionate. Ah, now here's an area in which Darryl is much better than average: for a guy, that is a good ass. Encouraged by your squeezing hands, Darryl starts making longer, deeper thrusts. This does result in him slipping out a few times, though, but he eagerly fixes his mistake in a flash each time. He might be able to make you cum like this, if he could keep it up for long enough.

Without warning, Darryl pulls out of you and breaks of your kiss, giving you a final peck on the way. Did he cum? You didn't notice a thing... You look at Darryl, now kneeling between your legs, and spot no trace of any cum in the condom's tip. He smiles at you as he pulls it off, baring is still very hard, throbbing cock. You scramble back from him, and sit against the headboard with your knees pulled up to your chest. "What the fuck are you doing, Darryl?!" Surely he's not planning what you think he's planning? "Relax," he says, still grinning, "I'm not going trick you or anything. Well, I am, but not in that way. Here." He gets up from the bed and turns away from you, giving you a good profile view as he starts jacking off.

Just a few short pumps later, Darryl leans his head back and groans as he starts shooting ropes of cum all over his floor. What the hell just happened?

"Darryl, " you say in a demanding tone, "What. The. Fuck." He turns his head to look you in the eye, still holding his dripping cock, and shrugs. "Oops. Silly me." He grabs your pants - your pants, the bastard - and wipes the remaining cum off with it. "Why did you-" You fall silent as it dawns on you. The GAME was for him to cum inside of you while wearing a condom. He did not. Clever little shit.

"What the fuck, asshole! We had a deal!" "And I'll keep my end, " Darryl calmly replies, "You set a 1 hour time limit for the GAME. Looks to me like we still have some 50 minutes left. It'd be a shame to waste them, don't you think?" He grabs his desk chair, swivels it around, and sits down in it, facing you. He leans back and crosses his arms over his chest with an infuriatingly self-satisfied grin on his face. His cock is already growing hard again between his legs. Darryl inclines his head towards it, then back up at you. "Well? Go on, then."

"What, did you really think I was just going to go along with this?" Confident now that, at the very least, he's not trying to enslave you, you get up from the bed as well, grab your underwear up from the floor, and begin putting it on. "Fuck off," you continue, "I'll find some other way to get back at Mandy." Impossibly, his grin grows even wider. "No you won't. If I don't fill up a condom inside of you in the next 49 minutes, I win the GAME. Which means we go with my plan for Mandy." "Fuck off," you shoot back, "I'll find someone else." "Again, you won't. It's my prize for winning the GAME, remember? You said, 'we'll go with your plan', not, 'we might consider your plan if we feel like it'. The GAME will make you. Well, I sure hope you've got a good plan for getting Mandy to let me fuck her. Consensually, mind you. That was the plan, after all."

Well... Fuck.