It's a war of attrition

Your preemptive start lets you securely tug the room service boy a fair distance, and after a short struggle, you're pretty certain that you've crossed the line that Mistress Jessica prepared for you...Despite that, she shows no sign of ending the game, and you're left pulling against the room service boy, your balls aching terribly.

"Keep pulling boys. If I see either of you slack off, you'll lose right away. And you really don't want that...my first seat was **** and missed it, but I had quite a few bottles of rather expensive wine sent up earlier as well. Neither of you slaves seem like the wealthy type, so it might be tricky for you to pay for everything."

She laughs in amusement as she motivates both of you to pull harder, though you can't help but wonder if the game will actually end short of one of you giving up or breaking...the pain is unbearable, and the fact that you have to contribute to inflicting it on yourself is pure ****. It's probably less than a minute of tugging, but you feel like you've already spent an eternity struggling against your rival.

Walking over in front of you, Mistress Jessica squats down and puts her ass in front of you, just out of your reach. The gorgeous round surface is mesmerizing, and you lose several inches of your hard-won distance to the room service boy while you're captivated by it.

"Kiss it and you win." Sounding very amused, Mistress Jessica taunts you with her ass, and you struggle more fiercely than ever, your lips puckered as you strain to get closer. The room service boy is clearly just as **** to stop you though, and after some time, you can't manage to close the gap, and Mistress Jessica stands up, leaving you frustrated and in agony.

You see her walk around and repeat the same offer to the room service boy, who seems like he'll tear something for one or both of you with his **** pulling. You manage to hold him back too though, and the two of you continue your struggle. Your balls have never hurt so much before, and the only things keeping you going are the carrot (Mistress Jessica's ass) and stick (debt you'll end up with if you lose) she's prepared.

Both you and the room service boy seem dedicated to winning, and even though the pain has two sets of whimpers filling the room, it doesn't seem like the game will end until one of you passes out or decides the health of your balls is more important than winning...