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Chapter 19 by GuerrillaShark GuerrillaShark

What's the next challenge?

Anal

You haven't even driven home yet before you get his text.

  • Prepare your anus. First to cum wins. Come at 10 -
  • Im cuming at 10 but we aint playin til 3 -

Prepare your anus? No way are you going to let him cheat again. Five hours should be enough for him to calm down. Still, you should edge just in case. After all, he didn't cum today, so he does have the advantage.

At night, your thoughts turn to the reward. You were finally going to have sex! Anal sex! You can already imagine everyone's face when you tell them at school. Tony was the only guy at school who had sex yet, but it was just vaginal with that thot Angelina. When they find out you did anal, you'll be king. Of course, you'll have to keep quiet that it was with Bob. Not because you don't want to embarrass him, but because you don't want to embarrass yourself.

Speaking of Bob, you're surprised he's gone so far with the game. He can't honestly imagine he'll win, can he? Not after the way you humiliated him this morning. So does that mean he actually wants to get fucked up the ass? Doesn't that shit hurt? Why any man, or woman for that matter, would want to do that is beyond you.

As you sleep, all you dream about is the way Bob submitted to you. It makes you feel real tough knowing that you got a larger guy on his knees for you. And you just know you'll do it again and again....


You edge three times the next morning, driving over to Bob's as soon as you're soft enough to fit back in your pants.

You arrive promptly at 10, and make sure to keep your eyes on him at all times. He doesn't want to leave you either, guessing that you're up to the same thing as him. Even when he goes to use the bathroom, you're knocking at the door 2 minutes later. Of course, you then make sure to take two minutes for some stimulation yourself.

You get along reasonably well with each other, considering what happened the day before. At 3, though, Bob drops a disheartening revelation:

"Oh dude, I forgot to tell you - my parents called and said they were going to be coming back in a few days."

"Damn. We'll have to stop playing then, won't we? You're one lucky son of a bitch, I tell you." You're surprised at how annoyed the news makes you. You were really enjoying using him. "You better not be making this shit up, you know. I'll be here to check that they really do come back."

"You need to stop acting like a fucking KGB agent. You might have convinced yourself that you're some unbeatable tough guy, but I'll show you. C'mon, 1 v 1 me!"

As you begin, you find yourself completely ignoring the porn. Instead, you focus on Bob's dick, trying to guess who is winning - based off the past games, it seems you're both neck and neck. You need to do something to get an edge.

"Look at that ass getting pounded on the screen. A nice muscular ass. It looks just like yours. How does it feel knowing you'll be loosing your cherry tomorrow?"

He grimaces, but tries to ignore you.

"Yeah, you can make all the faces you want, but I can tell what you're up to. Choosing anal as the next challenge? You knew you were going to lose. And even if you won, you would have just asked me to punish you again, wouldn't you? You'd find any excuse just to get my fat cock up your ass."

He really picks up speed now, going as fast as his hand will allow him.

"Don't even bother trying, dude, I'm way too close already. Don't you see you can't win? You don't have the sexual prowess of a real man."

You don't know whether its because your words ruined his confidence, or because they made you feel real cocky, but you definitely blow your load before Bob. It's close, but it's clear you've beaten him yet again. You allow yourself to relax as you watch him finish. I'm the man.

"What the fuck! How the fuck do you keep on winning? It's not fucking fair! Fuck this fucking game!" Bob explodes. He's like a ten year old playing Dark Souls.

"I've never seen someone's idea come back to bite them in the ass so bad, dude! You know this game was the best thing ever - I'm real glad you came up with it."

"And fuck you!" He's mad, but at least today he doesn't make you leave.

You leave of your own volition after a few hours, though, his pouting mood driving you away. With no idea what to do, you call up two other friends - Mike and Tony - and make plans with them. They ask if Bob is coming, but you tell them he's not feeling well. You don't want to hang out with him when he's like this.

The Next Day

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