Stupid Bets


Hailey and Dylan were outside, beside his pool, drinking and sunbathing. At least, they were sunbathing as much as anyone ever did any more. They were half in the shade, and covered in sunblock, so mostly what they were doing was being outside and lying in the breeze because it was hot indoors. Hailey had her top off, and was mostly on her front, but she knew whenever she sat up or turned over, Dylan looked at her tits.

He looked at her a lot, and she didn’t especially mind. They had sex sometimes, but neither of them really made a fuss about it when they weren’t. They probably would today, though, she thought, because she was in half a bikini, and they were drinking.

Dylan had started talking about sex already, which was usually what got them started.

He was going on about lapdances, and how he didn’t get why people paid for them. You wouldn’t get off, he said, so what was the point. Why even bother.

“You could get off,” Hailey said.

“Nah, not just from…”

“Of course you could.”

“Don’t be stupid, it isn’t enough…”

“Yep,” Hailey said, confident.

“Yeah, and how do you know?”

“I know.”

“Did you work as a stripper.”

“Don’t be a dickhead,” Hailey said. “And I’m still right.”

He was thinking now. “Have you done that or something? And got someone off?”

“Nope. But you still can. Both of us could, I’m pretty sure.”

“Nah,” he said. “I don’t…”

She sat up, and folded her arms over her chest, and looked at him for a moment. “I will,” she said. “Keep talking, and I promise, I’ll prove it’s possible.”

He looked at her, thinking.

“I will,” she said again.

“Okay, go on.”

“It’ll cost you,” she said. “If you’re wrong.”

“Of course it will. What?”

“I don’t know. You’ll owe me something. Something big. I’ll tell you what it is when I want it.”

“Something like what? Cleaning your bathroom?”

She grinned. “Um, nope. Something like some really perverted sex thing no-one else will do with me.”

“I’m not going down on you when you’ve got your period.”

“I know you aren’t. You’ve said, a lot.”

“Okay, so not that.”

“Maybe that. Because how it’s owing me something really big. But maybe if you’re nice I won’t make you do that.”

He thought about that. “Okay, fair enough. And what do I get if you’re wrong?”

She looked at him for a while, and knew exactly what he meant. She sighed. “Fine,” she said. “Yes. That.”

He grinned.

“But don’t get too smug,” she said. “Or it’s period head if I win.”

“Okay,” he said. “But it’s my dick up your butt if you lose.”

“I know,” she said. “Fine. So, bet?”

He thought for a moment, then shrugged. “Okay.”

She glanced around. It was mostly private out here, but she still wasn’t sure she wanted the neighbours watching. “Come inside,” she said.

They went into the lounge, and she got him to take off his shorts and then sat across his lap in just her bikini bottoms. She put her hands on the couch-back, and leaned towards him, so her tits were almost in his face.

He started to get hard, and she grinned.

She slid herself down onto him, catching him so he pressed between her legs. She shifted, so he was right on her pussy, and then slid slowly up and down. He felt good, there. He was sliding right against her, already hard, and she could feel herself getting wet. She slid faster, moving carefully up and down. He was pushing her bikini against her, making a soft hollow of silky cloth that slipped against her all warm and sleek. She slid herself along his shaft, getting faster, watching him. Feeling her breath get rough, hearing his get that way too.

“Okay,” he gasped. “Point taken. I think I can.”

“Yep,” she said, and kept moving. “It’s me that’s tricky, not you.”

He came suddenly, with a groan, in a thick spurt that mostly went on his tummy. She watched, liking that he had, liking she could make that happen, still sliding herself along him, even as he got softer. Some of it had gone onto her bikini, as she slid up into it, making it a little sticky on the front and she liked the warm dangerous feeling of that, too.

She slid herself, and he watched her. She’d never mentioned to him that she’d been with women a few times, because she knew exactly how he’d react. She’d never mentioned it, but it had helped, knowing what to expect, with this. Sex with those women had been pretty much the sex she was having now. She’d known she could fuck like this, and had known what to do.

She kept sliding herself. It was almost easier, she realized, as he went soft. He was a squashy supple thing to press down against now, something which fit neatly against her shape, making her feel him more. She slid, gasping, and fairly soon, she came as well.

Still breathing fast, she got off him, and pushed her bikini bottoms down.

“I’d better wash these,” she said.

He was looking at her naked. As he would, she supposed. Looking at her naked, and looking at her while she was all turned on and sexy too.

“Oh,” she said. “Not done yet?”

He grinned.

“Head?” she said.

“All right.”

“Um, for me?” she said.

“You as well.”

He pulled her onto the couch beside him, and she dropped the bikini bottoms on the floor, and let him turn her around into a sixty-nine.