Kenzie learns she likes it rough

"Jake, can we go somewhere a little more comfortable?" Kenzie looked like she wanted to say more, but she glanced at the other girls and decided against it.

"Sure, why not." Jake pointed in the direction of the bedrooms. "Janie, we're going to go make a mess in your parents' room."

Janie held up her hand to stop Jake. "Let me get something to help you on the way."

Janie, Kenzie, and Jake stopped in Janie's room first. Janie took a bottle of lube and a small box of condoms out of a drawer. She handed them to Jake, winked at Kenzie, and walked out.

Jake led Kenzie to the master bedroom. It was a nice, large room with a fancy bathroom attached. It was very tidy and clean, as though the owners cleaned it up before traveling.

Nobody in Jake's family put in that much effort before going on a trip. It seemed weird. Jake got the idea of doing something about it, but he was naked in the room with a bottomless girl and he had a bet to win.

Jake started by stripping Kenzie fully naked. The power behind his bet wasn't giving him any hints so he just pulled her shirt and bra straight up over her head.

Jake admired Kenzie's figure. Her tits were, uh, DD? (Jake didn't know anything about cup sizes.) She was roughly Jake's height and not fat by any real measure. She looked good. Healthy. Well-proportioned. Very fuckable, not strictly eye candy.

"Jake, are you going to touch me? Did you really break your dick in the living room? You've been holding it weird and it's not even hard now."

It did still hurt a bit.

The power took control here and Jake slapped Kenzie on the side of her body, right below the ribs. It was hard and loud, and Jake felt as surprised as Kenzie looked. His hand hurt, so how did she feel?

"Yeah, I'm just admiring my new toy," said whatever was pretending it was Jake. "Not much jiggle to that belly. Why do the other girls bully you?"

"We were friends in Middle School but then they started working out more. I..."

"...Jake, you're hard again."Jake snapped to alertness. Kenzie had been trauma-dumping for ten minutes or so and Jake was getting a little invested in the drama, but he didn't understand half the stuff he was saying to encourage her. The whole thing sounded overblown to him, and bet-powered "Jake" seemed to agree because he was starting to give advice like "sometimes friends just drift apart when they mature."

He was still on autopilot. "Oh good. I hope that conversation counted as foreplay to you, because now you're going to get pounded through the floor."

"What--"

Jake interrupted her by putting his arm behind her back and throwing her face-first off the bed they were sitting on. He was unnaturally strong for the motion and the low-carpet floor wasn't very soft, so the impact was worse than the one in the living room.

"WHAT ARE--"

"Shut up, we did the talking already." Jake kicked her in the right elbow as she tried to prop herself up with the result of dropping her face into the floor again. That had to be getting painful.

Jake dumped lube all over his aching cock but avoided the condoms. He positioned himself behind Kenzie on the floor, spread her butt with both hands, and put his tip near her virgin little slit.

"W-WHAT--"

"What do you think I'm doing, Kenzie?" Jake reached over with his thumbs and tapped on the edges of Kenzie's asshole. She squirmed against the unfamiliar feeling. He was still on autopilot but her really wished he could thrust in.

"Um... I.... Um..."

"Say WHAT again, bitch."

Kenzie paused. She held her breath for a few long moments and then whispered a fearful, "What."

Jake didn't split her pussy open. With only a slight adjustment, he pulled up and plunged himself balls-deep through Kenzie's unprepared anus.

She screamed. The power let go of Jake and he didn't move, he was just as shocked as Kenzie.

"I, ooh, please, how are you, I, uh, please."

Jake stayed frozen. What was she getting at? Pleasure, pain, both? Was she a masochist? Was she becoming one now?

"Jaaaake." Soft, slow, breathy. That came out like pleasure. "Jake, do it, teach me! BREAK ME!"

Jake started pistoning as hard as he could, mindful not to pull back too far for fear of hurting his privates again. It was unskilled and it looked painful to Kenzie. Jake could see shit and blood splashing onto his pelvic area but he was afraid of what would happen if he stopped now, so he looked away and kept going. No power helped him or guided him.

About two minutes in, Kenzie started talking between gasps. "You are. Going deep. It feels. BAD. I love it. I love it. I bet you. You fill me. Shoot deep. All inside."

"Oh it's a bet alright. I bet your ruined asshole will leave cum leaking out on Janie's mom's floor. And when I win, you have to clean my dick off with--" Jake stopped. He had been talking on his own but the power wouldn't allow him to have her lick it off.

Kenzie finished the sentence: "My mouth?"

"No, that's what you get if you win the bet, you filthy whore. I want you to clean me off on Janie's mom's pillow."

"Haha, that's fucked uuuuuh, uuuaaaAAAGH!"

Kenzie launched into a screaming orgasm and it was only now that Jake noticed she had been fingering herself with her left hand. Jake also came, and dumped what felt like a big load into the inexperienced girl.

But when he pulled out, she was leaking onto the floor.