Eric into Clarissa, Jake into Kenzie. Here and now.

"I bet Kenzie and Clarissa would have a great time fucking me and Eric," Jake stated confidently.

Eric looked confused but everyone else had a good laugh.

"Careful with those odds, kid," Janie said with concern, "Clarissa hates men more than any other lesbian I know. Kenzie has a terrible time with men. Don't bet too much."

Amazing. The bet itself seemed normal to her and she was worried about consequences if Jake lost.

Jake felt like a supervillain. He needed to monologue. "Janie, please, a good wager is what makes it fun. We wouldn't be having such a grand time if the stakes weren't exciting. In fact, if I win, you all have to help me think of bets when I want you to, including the vict-- Hmmm. I mean, including finding some interesting people to gamble with." He pulled off his shirt and walked toward Kenzie. "If I lose, then of course Eric becomes the personal **** of your friend group."

Janie gasped. "Jake! You're not going to win that bet! We all hate Eric, but he'll be your enemy forever if you do this!"

Eric looked gloomy. He pulled off his own pants and underwear in one rough, angry motion, like a child throwing a fit. Jake had already noticed Eric wasn't well-endowed, but comparing to Jake showed he really was small. Probably not a "micro-penis" but getting close. Eric was expecting to lose, but he wasn't fighting back.

The other girls watched and chatted as though this was the most casual thing in the world. They displayed mild interest, showing open disdain for Eric and a bit of curiosity about Jake. Janie remained nervous and watched Jake more closely, clearly concerned over the big stakes (even though Jake had spared himself). Jake didn't answer her, and she didn't push it.

Jake finished undressing and reached for Kenzie, who was visibly nervous. Jake was, too, but he tried not to show it.

"What's wrong?" Jake asked tenderly. He surprised himself by how sincere he sounded, since he didn't really care.

"I--I--I--I'm still a virgin. My parents always say sex is so sinful. I don't think I really believe that God stuff any more but I don't know, I don't... I don't... I don't...."

She was clearly about to cry. Instead of comforting her, Jake unzipped the ugly shorts she was wearing and then yanked them to her knees. He didn't take time to savor the shock on her face. He stepped sideways while pulling her around and then grabbed her hair to pull her toward the coffee table. She caught her balance by putting her hands on the table, which was short enough that it left her leaning over quite a ways. She reflexively bent her knees to drop out of her clumsy pose but this slammed her hairy pussy straight onto the tip of Jake's erect and waiting cock.

Jake didn't quite penetrate because Kenzie reacted too fast. She yipped like a hurt dog and popped back up and tried to move her feet for balance, but she made it worse because her shorts restrained her knees. Her hands slipped and she only avoided faceplanting because Jake grabbed the hair at the back of her head and yanked hard, which looked painful and brought out a strained, **** gasp from poor Kenzie.

Kenzie was paralyzed with pain and confusion just long enough for Jake to throw up a rock star "horns" gesture with his free hand, which... Oh, which Kenzie could see (barely) in the reflection of the big TV. They were facing the TV. OK then.

Jake yanked back on her hair harder than he even knew he could and slammed his own hips forward. His cock, perfectly aimed, slipped right into the defenseless pussy lips and impacted the top of the vaginal canal too directly to adjust and slide in which sent shocks of sharp pain crashing down the length of the shaft and "oh god oh fuck what the fuck ow ow ow ow ow ow ow"

Jake reeled backwards and landed on his ass with a dull thud at the same time that Kenzie pitched forward onto the carpeted floor, bare ass **** into the air by the coffee table.

Jake didn't choose to do any of that. In one moment he was delivering the smoothest **** penetration in the history of sexual ****, and a split second later he was suffering the most painful and embarrassing defeat of his entire life.

WHAT THE FUCK WAS THAT, he thought.

He looked at Janie, who was nervously giggling. Janie met Jake's eyes and blinked with some emotion that Jake wasn't sure of. She finally peeled her eyes off of Jake and walked over to Kenzie, where Kenzie was sobbing with--

No, Kenzie was laughing. She was laughing hard. "Oh Jake. How have you ever won a bet with skills like that? You really had me going there for a second, but I can't--" Her laughter increased to the point where she had to wait before talking again. "Oh my gosh I don't know why I was afraid of boys. You're as useless as Clarissa says. And you are one of the good ones!"

Kenzie continued laughing and Jake's mind raced to catch up. Why? WHY? And actually, did he need medical attention for his dick, because it hurt like crazy, can you break your dick that way?

The earlier question answered itself first. Jake realized he had only bet on the girls having fun.

Oh no.

He looked toward Eric and saw Eric glaring at his own manhood in shame. Clarissa was standing in an exaggerated dominant pose with her feet shoulder-width apart and her hands on hips. Both of them were completely naked, not a stitch of clothing on either. There was some white cum dripping down the tanned skin of her slim, toned thighs, but Jake assumed a lot of it had gone onto the floor.

How'd they do all that so fast?

"Say goodbye to your friend, Jake," Kenzie said playfully. "He'll be busy as our ****."

Kenzie seemed far more confident than she had when she arrived.

"Oh, I'm not done yet," said Clarissa. She cocked her hips to one side, spread her bald cunt open with two fingers, groped a B-cup breast with her other hand, and made a kissing motion. It was a very strange gesture that seemed menacing somehow, like a taunt that a fighter would use in a hentai video game. "Men always stop too early, but in the spirit of the bet I insist on a round 2."

Eric frowned and Kenzie chuckled again. "Yeah, I'm starting to like Jake, he's at least got some confidence. Let's give them a fair chance."

Jake was starting to think he didn't have serious medical damage, and he wanted to keep it that way.

"Damn right. And I bet fifty bucks I'll show you how real skill feels this time." Jake stood up. He noticed Janie giving him two thumbs up. He looked into Kenzie's eyes with what he hoped was a passionate stare and said, "Let's go."