Upping the Stakes

"Hey, can we try that one?" Ashley held her latest find up in the air.

Tanya regarded the shiny wooden cane with a raised eyebrow. "I don't think you're ready for that one, yet. Maybe find something more beginner-friendly."

It might've been a mistake to show Ashley her kink box already. Barely a week had passed since Tanya had asked Ashley if she was willing to try some not so vanilla stuff and since then there'd been no stopping her girlfriend. Turned out, Ashley had been a closeted sub for all her sexual history and what she was lacking in experience, she more than made up for in enthusiasm.

Not that Tanya was such a veteran herself. Her track record were a three month relationship with Mary, which had run its course when it'd become clear that Mary really wasn't a sub at heart. And, of course, the best night of her life: The play date with Layla. One night of, in equal parts, kinky sex and cuddles. It would've turned into more than a one night stand, if not for the fact that Layla lived on the other side of the planet and had only come over for a convention weekend.

So, truth be told, most of the toys in her box hadn't seen much use, if any, but Tanya liked having them around nevertheless. It felt good to own five different spanking implements. And you had to be prepared in case an opportunity presented itself. Like it was doing now.

"It can't be that much worse then the flogger, can it?" Ashley asked. "And the flogger was no problem at all."

Tanya gave her a weak smile. Sweet inexperienced Ashley. The cane had made even Layla scream, and that girl had had a remarkable pain tolerance. "Believe me, you wouldn't survive five strikes. Two if I don't hold back. How about we try the belt today? That's also fun and we can work ourselves up from there."

"Wanna bet?" Ashley asked before Tanya had even finished talking.

"Bet what?"

"I say I can take five hits. Easy." Ashley twirled the end of her ponytail around her fingers. Even in the short time they'd been together, Tanya had learned to recognize the gesture. It always lead to things happening, none of these things being innocent.

"And I say you're overestimating yourself there." Tanya already knew that she couldn't dissuade Ashley that easily, not when her girlfriend had already gotten so exited. But then again, did she really need to? A quick demonstration couldn't hurt. Well, it would hurt. A lot, actually, but that was the point. "We can give it a try, but if I'm right, you've got to clean the kitchen. Still in?"

Ashley gave her hair a last twirl before she threw her ponytail back over her shoulder. "Okay, but if I win, you'll have to clean it."

Tanya tried and failed to make sense of that. "It's my kitchen. I have to clean it anyway."

"Yes, but I'll be watching. And you'll be naked."

"Oh." Tanya looked at her grinning girlfriend. "That's not very subby of you."

"But it's fun." Ashley came closer. Close enough that their noses almost touched. "Scared that you might lose after all?"

A bit, maybe, Tanya thought. She was still convinced that it was too early to break out the cane, but Ashley was so eager to push her own boundaries, she might just make it. Especially if she had additional incentives. However, Tanya wasn't going to chicken out just because there was a chance of losing. That only made it more interesting. "Wanna up the stakes?"

Ashley giggled. "Sure. If I win, I get to spank you. And then you'll clean the kitchen. Naked, so I have a good view of your red ass."

Maybe Tanya had labeled Ashley the wrong way. Seemed like she'd stumbled upon a switch after all. The idea exited her more than she would've thought. Ashley's deliciously kissable lips so close to her might've clouded her judgment a bit, but at the moment she wouldn't have minded being put over her girlfriend's knees. She also didn't mind showing Ashley who was the boss, though.

"And if I win, you clean the kitchen. Naked. And you'll wear nipple clamps while you do it."

They'd played with the clamps once and that had been enough for Ashley to develop an intense love-hate relationship with them.

"Deal!" Ashley closed the gap and kissed Tanya.

She only stayed in control for a second. The moment their lips touched, Tanya wrapped her arms around Ashley and shoved her tongue into her mouth. All the talk about the bet had turned her on to the point where she'd have been ready to postpone everything and drag Ashley into bed with her right away. Well, almost. Getting to use the cane again was definitely worth having to wait for the sex.

"Get ready," Tanya ordered as she let go of her girlfriend.

"Right away. Mistress." Ashley giggled at the last word. Tanya let it slide. There was enough punishment on its way already.

With swift movements Ashley took off all of her clothes. Not that she had to be naked for a caning, but Tanya had already learned about this particular kink of her girlfriend: Ashley loved showing off her body and she especially loved being nude while Tanya still had her clothes on. Tanya saw no reason not to indulge her. It did add to the dominating aspect and as long as she could take off her clothes when the real sex started, she didn't mind staying dressed a bit longer.

"Bend forward, hands on the bed!"

Ashley twirled her ponytail once more before she followed the command. Tanya picked up the cane.

"Remember: You can give up at any time. But if you do, I win."

"And if I take five hits, I win." Ashley grinned. Her hips shook slightly. Tanya was sure, if she'd reached between her girlfriend's legs, her fingers would've come back drenched.

"Your hands need to stay right where they are."

Ashley nodded and bit her lip. "Do it!"

Swish. Tanya hadn't even put much force behind the strike, but the moment the cane connected with Ashley's cheeks, her mouth opened in a silent scream and her hands twitched. Technically they left the bed for the fraction of a second, but Tanya wasn't going to point it out. She was impressed that Ashley had managed even this amount of self control.

"Sure you wanna go on?"

Ashley took a moment before she answered. A thin red line was already forming across her butt. "Yeah, I can do this," she finally said.

"Even if I don't hold back for the other ones?"

"You were holding back?" Ashley laughed in disbelieve. "That hurt like a bitch."

"Believe me, you've seen nothing yet." Tanya gently tapped Ashley's ass with the crop. She giggled at how much that made her girlfriend twitch. "You could save your ass a lot of pain if you went to the kitchen right away."

"You wish." Ashley dug her fingers into the pillow. "Come on! Show me how bad it gets."

Well, if she asked for it so nicely... This time Tanya flicked her wrist as quickly as she could. The cane cut through the air and connected with a sharp snap.

"Ah, fuck, fuck, fuuuck!" Ashley almost screamed. She rose up on her toes and grabbed the pillow as if trying to strangle it. An angry red welt bloomed across her cheeks. It made the first one look pale in comparison.

"Everything okay?"

Ashley made a sound somewhere between a laugh and a gasp. "The strike wasn't so bad. But, God, it still keeps going." She wriggled her butt in an attempt to soothe the burning.

"Yeah, that's what makes the cane so fun." Tanya felt a lot more giddy than she had any right to be. It was too cute how Ashley kept twitching, but still managed not to reach back. And she'd almost forgotten how satisfying it was to swing the cane. Losing the bet sounded totally worth it, if it meant she got to use her toy a few more times.

Ashley didn't tap out, which was all the encouragement Tanya needed. She hit again and, after giving her girlfriend just enough time for the pain to fully register, a second time, right on the same spot.

Tears shot into Ashley's eyes and this time she screamed for real. It was such an adorable noise. Tanya had made her whimper before, but never to this extent. She could really get used to these high pitched wails.

"Fuck, that hurts!" Ashley's knuckles were white from grabbing the pillow so hard, but she was laughing. Maniacally so. "Again!"

When Tanya raised the cane she realized that she'd already lost the bet. This was the fifth strike. Ashley had let the last chance to give up pass. Well, if she couldn't win anymore, she could at least make the most out of her loss.

Several bright stripes already decorated Ashley's cheeks. They'd definitely bruise. Ashley would have a lot of fun trying to sit comfortably the next day. And Tanya would have a lot of fun spanking her already tender ass. She let the cane sing once more.

The last strike hit diagonally, so it crossed all the previous bruises. The pain made Ashley jump and she let out another long, high pitched scream, but still didn't break position.

Tanya was just about to congratulate her on her bravery and her victory, when Ashley said "I give up."

"What? Why would you do that? I've already lost."

"Yes, you have. And now I've also lost. Guess we'll get to work on the kitchen together." Ashley straightened up, very carefully as to not upset her glowing butt. She reached back and winced at her own tender touch.

"You're unbelievable." Tanya pulled her into a quick kiss. "Is your butt okay?"

Ashley snorted. "It's pretty fucking far from okay. That cane is the devil. I only pulled through because I knew I'd get my revenge in the end."

Right, there'd been another part of the bet. One that wasn't about the kitchen. Tanya swallowed hard. Her girlfriend looked remarkably composed for someone who'd just went through presumably the most painful experience of their life. More than that, she had a mischievous grin that Tanya had never seen on her before. This wasn't going to be a playful spanking. Then again: Was a playful spanking really what she wanted?

"Will you need that?" Tanya asked and offered the cane.

Ashley's grin got even wider. "I wasn't going to, but now that you ask..." She took the cane and gave it an experimental swing.

The sharp hissing as it cut through the air sounded a lot more threatening when you were about to be on the receiving end. Soon Tanya would find out if these red welts were as painful as they looked.

Until this day, Tanya had been convinced that she was a pure dominant. Nothing got her going faster than raining punishments down on her girlfriend's ass. Or so she'd though. But seeing Ashley standing self-assuredly in her nakedness, the cane raised threateningly, brought that familiar warm tingle to her pussy. Whatever was going on inside her, she needed to get to the bottom of it.

Tanya took Ashley's place at the bed. She didn't even bother getting fully undressed and just pulled her jeans and panties down to her shins. "No need to go easy on me."

"Even when you scream?" Ashley stepped behind her and gently stroked her ass with the thin wood.

Tanya didn't know if she'd ever been this wet before. She knew, if she didn't use this opportunity to its fullest, she'd regret it later. "Especially when I scream."

Ashley laughed. "Let's see how long you'll keep up that attitude." She swung the cane.

That evening, Tanya did scream. A lot. But her attitude didn't change. The only thing that changed was how her relationship with Ashley played out, going forward.