Two Hundred Dollars Ch. 26

34 Dollars

Bailey rushed into Kent's room on Thursday evening.

"I don't have much time," she said, "I've gotta head out for a thing."

"You don't have to do any if you don't want," Kent reminded her.

She waved him off and made two marks on the white board.

"Over top, okay?" she barely had enough air to breathe, looking at him with wide-eyed pleading.

"Sure, whatever," Kent said. "How you want it?"

Bailey took the stool out and put it in front of his bed. She climbed up on it and bent over until her breasts touched the bed.

"Quick," she begged. "Before Carson gets back or I have to leave."

"Alright, alright," Kent acquiesced.

What's her hurry, today? Why even bother?

Still, she owed him money, and she'd chosen this as her method of payment, so he felt like he had to get his money's worth.

Too bad there's no inspection. She's gotta look pretty red everywhere.

Not knowing which way to go, he started slapping her denim-clad rear, spreading out his assault as evenly as possible.

Breathlessly, Bailey gasped out the numbers from one to twenty, her voice slowly rising in pitch until she barely squeaked out, "Twenty" at the top of his hearing range.

She stood back up and turned to him, stepping off the stool, and said, "Thank you."

"Thank you, too?" Kent replied, peering at her carefully.

"That was good," she clarified. "Keep the count rolling, right?"

"Right," Kent agreed.

"Okay, I gotta head out," Bailey blurted and whisked out of the room.

Seconds later, she'd gone out the door into the cold November air.

That was weird. Even for us.

Kent sat for several minutes, looking back and forth between the white board and the doorway through which Bailey had exited. Did she feel obliged to get spanked every day? If so, why only two? If her ass felt too sore, why even do two?

He shrugged and returned to his work.

=============================

Friday afternoon, Kent eyed the same board while he tried to sort out all the emotions he felt every time he caught a glimpse of the number in the corner.

Just thirty two bucks left, he shook his head as a pang of something struck his heart. What is that?

Regret factored into it, certainly. The original two hundred dollars that had started this whole journey had seemed inexhaustible. Kent had thought he'd have months of time to try every damned way of spanking Bailey throughout their entire two semesters of cohabitation.

But Bailey had risen to the challenge in far too many ways and she looked to be plowing through the last of her debt ten dollars at a time.

I can't even slow her down, he realized. I don't have the right, even if I wanted to.

He wasn't even sure he wanted to moderate her pace. His own desire for speed, its roots originating in some place well above a base lust to redden her cheeks, brought the most confusion to the shock waves spiking in his chest.

She wants to get through it, and maybe so do I.

Bailey hadn't come by today, even though she usually managed to find time on a Friday afternoon, and Kent breathed with relief. It gave him a tiny bit of space in which to think.

Even if I don't get much of a choice, I should still know what I want, he declared firmly. Do I want to rush through this? Get past this debt to whatever lies beyond?

Kent's eyes widened and he glared at the floor.

Whatever lies beyond? He noted the gap in his planning. I need some of that spice from Dune. The stuff that turns your eyes to blue-on-blue and lets you see the future.

Instead of the future, Kent saw a wall and had no idea what happened once he climbed over, or dug under, or smashed through it. Shaking his head, he thought back to his last encounter with Bailey. He'd tried his tongue, knowing the risk, and it had almost worked.

I think I rushed it, he frowned. That's what Bailey said. I don't think she said it just to be nice. I probably could have made her come if I'd been more careful.

Kent resolved to take greater care in his next oral adventure, assuming Bailey wanted to try again, and then packed up to head off for his late lab.

=============================

Bailey grimaced as she entered the apartment. She'd dawdled at school all afternoon, studying unnecessarily in the library on a Friday, so she wouldn't run into Kent.

She didn't have any real need to hide from him, per se. But if she saw him again, she knew she'd feel a compulsion to make a few marks on the white board, and that meant more spankings.

I'm sore already and completely red, she moved carefully down the stairs in the dark. I could do one dollar, two if I'm lucky. And what's the point of that?

Knowing she wanted to move things along, Bailey wanted to pay ten dollars at a time. Once down the stairs, she suppressed a shiver and peeked in Kent's room. With the handover of the last picture from the bathroom and the twenty spankings on Thursday, he'd changed the total to thirty two dollars.

What's the faster way to drop that? Should I let myself heal a bit and do big chunks at a time? Bailey wondered. Besides, Laura should be back tomorrow.

It made sense to take a break if that sped things up in the long term. If she took efficiency as her goal, just like Kent had said, she should make the best use of her resources.. Taking spankings in exchange for money counted as wisdom from her perspective and their arrangement was 'good' in that sense. But if she saw Kent, Bailey knew she'd feel the urge to take a few more dollars off the board, just like she had on Thursday, and work her way through her debt. In fact, just imagining Kent coming down the stairs in a few hours started the tingling and warmth between her legs, setting her stomach churning with anxiety.

I need another option.

=============================

Arriving home late, in the cold and dark, Kent came down the stairs with fresh snowflakes covering the shoulders of his jacket. Looking past his own open bedroom door, he saw that Bailey had left her bedroom door open as well. After getting rid of his winter kit while making as little mess as possible, he adjourned to his room and turned on his computer, knowing very well that Bailey would come if she wanted.

Should I say 'hi' or something? Kent hesitated. I don't want to make it sound like I'm expecting something from her. But people can just say, 'hi', can't they?

Deciding too much time had passed for any greeting to sound natural, Kent called up his favourite MMO and prepared to set up a solo mission.

"Hey, Kent."

Damn, that was soft footed, Kent looked down to see Bailey's white socks flowing gently over his bedroom's carpet.

"What's up?"

Despite her grace, her movement to lie on his bed looked awkward.

I expected her to make a mark on the board, he realized. Is Carson home? I didn't even check.

Bailey laid on her stomach, more or less facing him with her chin propped up on her palms.

"Yes?" Kent prodded again.

She took a deep breath and he prepared himself to negotiate a new proposal.

What's she into now? he wondered, his eyes sliding along her body toward her denim jeans.

"Kent," Bailey turned her head and her eyes to the side. "Is there anything else you'd like?"

"Anything I'd like?" he tried not to stammer.

"To do," she prodded. "Or see."

"Instead of spanking you?" he clarified.

"Obvi," Bailey couldn't roll her eyes because she'd fixed her eyes on the ceiling to avoid his gaze.

"Your butt too sore?"

"Basically," she replied, deadpan.

Now her eyes did meet his, full of challenge.

Oh, crap, Kent tried to keep the fear out of his eyes. Alright, what are her rules?

"You're asking me," Kent drawled out. "What sort of thing I would pay for, that isn't spanking."

"Right," Bailey tilted her head slightly.

Feels like walking a tightrope here, Kent noted. I can't say a hand job or a blow job. That's right out. I can already tell.

His eyes wandered over her body, looking down her shirt.

She's got a thing about her boobs, he remembered, but I really don't know what to do there. Bailey's never even remotely suggested she's into that. I'd rather work my way up through whipped cream before we try crazy stuff with her tits.

With her ass, things had broken easily for him because she had started with spanking as the opening offer.

Besides, would I pay to suck on her nipples? Or pinch them? I dunno.

Kent shook it off. If her butt was offline for now and he didn't know what kind of boob stuff she went for, what body part did that leave him?

His eyes lit up.

"Can you make yourself come?"

"Pardon?" Bailey jolted out of some reverie.

"Do you, y'know, masturbate?"

"I, uh," she stammered. Her eyes darted around the room helplessly. "Well, yeah. Doesn't everybody?"

"I assumed so," Kent replied. "Just thought I'd check."

"So?"

"So," he went on. "I want to watch you, naked, while you, y'know, take care of yourself."

"Masturbate?"

Kent nodded, watching Bailey's thighs nervously twitching under the tight grip of her jeans.

"I have to come?"

Holy shit, is she actually going to do it?

"Yeah, no faking."

Bailey chewed on her cheek, her eyes coming in and out of focus.

"While you're watching?" she intoned. "For you?"

"That's right."

"Okay," she whispered. "How much?"

"Five bucks," he shrugged.

"Ten."

"Seven and a half."

"Eight," Bailey speared him with her eyes. "And I need to keep my panties on."

"Have to?"

"It's how I do it," she continued to stare straight at Kent.

"Alright," Kent held his hands up in surrender.

Quietly, her face calm and serene, Bailey stood up out of his bed and walked past him to the white board. The marker thumped against the board, over and over.

"You made ten marks?" he pointed out when she'd finished.

"Oh," Bailey inhaled deeply, "you'll need to do a few spankings, too. It'll be weird if you don't."

"Weirder?"

"Weirder," she agreed and held out her hand. "Come on."

"Where we going?"

"My room, obvi."

Kent allowed himself to be led by the soft, tenuous grip of her fingertips upon his. Swallowing nervously, he felt his heartbeat pick up.

I'm really going to see what she does? he realized. We know what Laura does, after all. What's the big deal?

Kent knew the difference: they'd never watched Laura pleasure herself.

Bailey closed the door and looked at him.

"This will be a bit more fair," she said, "if we're both in our underwear?"

"All right with me, I guess."

She grabbed the hem of his shirt and quickly lifted it, forcing him to raise his arms.

"Good," she nodded, and raised her arms while sticking her chest out at him.

There's no bra under her shirt. I didn't even notice until now.

He removed her t-shirt, looking down at her little breasts and their cold hardened nipples.

Winter has its perks.

Bailey had already set to work on his jeans before he even finished the thought. She knelt on the ground and managed to take his socks off at the same time. As soon as she stood, Kent took a knee and worked on the button of Bailey's jeans.

Whether she'd expected a spanking or not, she'd worn the white panties with the transparent, lacy front.

When Kent rose, Bailey stood before him in her panties and her socks.

"My socks?" she wondered aloud.

"I like them," he smiled.

Bailey shrugged, "All right. Let the show begin."

There's a chance I could learn something here, Kent realized, recalling his oral over stimulation. Maybe I'll see what she likes.

She held her palms together thoughtfully, her fingers touching her chin as she turned her back on him, looking at her bed.

"I suppose you need to be able to see, at least a little," she spoke softly. "And spank me."

Having made her decision, she climbed up on the bed on her hands and knees, then turned to his left to present herself in profile. She reached for the head of the bed and pushed aside one of her pillows to reveal a firmer, stiffer one she'd hidden under the covers. Kent watched in amusement as she fit this between her thighs, the corner pressing against her panties.

"You need to help a little," Bailey prodded, her hips rotating gently to rub the pillow against her pussy.

"This is one of those modern, interactive productions, then?"

"Uh-huh," she patted the mattress next to her and Kent took a seat, putting his hand on her right cheek.

He rubbed slow circles on her bright pink cheeks, listening carefully for the moans of appreciation that might guide him.

"Mm-hm," Bailey nodded, "Like that."

She's really going to come, he realized, listening as her breathing turned to panting.

"You should, um," Bailey gulped and took a breath. "You can start, y'know, the spanking."

She must have been turned on before she even came into my room, Kent realized. She didn't even know what I was going to ask her to do.

"Seven?"

"Yeah, seven," she blurted back at him.

He delivered the first spank the moment she agreed, hitting her right cheek low and hard.

"Oh!" Bailey cried out. "One."

Kent struck her left cheek next.

"Two!" she called, moaning out her next plea, "Faster, Kent."

Bailey doesn't want any spankings left over after she comes, and she'd going to come very, very soon.

Kent started hammering on her cheeks, back and forth, spreading his strikes around her pink flesh.

"Three! Four! Five! Six!"

He waited, then, watching as she dropped her shoulders to the bed and used her hands to force the pillow into right up into her lips. From his vantage, he could see the way the corner of the pillow rubbed along her panties and then pushed its edge into her vagina as she drove her hips down on it.

Over and over again, he watched the white fabric of her underwear dimpling into her body.

Wow, she's just barely penetrating herself with it.

Bailey moaned softly, her pitch rising, and Kent raised his hand off her cheeks.

Three last grunts issued as her cheeks clenched and she held her breath.

Right now.

Kent laid his seventh spanking across both her cheeks, a delightful echo reverberating off the walls of her bedroom as Bailey screeched out her orgasm and fell shivering onto her side, her reddened ass cheeks facing away from him.

Her hands shook as her bleary eyes reached out for his.

"Seven," she gasped out. "Seven."

Kent laid his hand on her hip and gently ran his fingertips over her thigh as Bailey curled her arms up in front of her chest.

"So?" she asked, after some time had passed.

"So?" he wondered what she meant.

"Was that worth it?" Bailey clarified.

"Not what I expected," Kent drawled as he smiled, "But yeah, worth it."

Bailey perked up, "What were you expecting?"

All of the pictures in his head, Kent suddenly realized, had come from watching porn. On the Internet, women performed for a camera, whereas he had asked Bailey to perform for herself. That made him pose a question.

"You probably don't even have to be naked, do you?"

"Not really," Bailey shook her head. "I probably couldn't wear jeans, though. Never bothered to try."

Recalling the way the pillow had poked at her entrance, Kent understood that.

"But you didn't answer," she pointed out, spearing him with her eyes again.

"No, I didn't."

"What were you expecting?"

"Not sure," Kent shrugged. "Do you ever use your fingers?"

"Once or twice," Bailey looked aside. "But I started with a pillow. When I was younger, I mean. I'm more comfortable with it."

She rolled over on her back, relaxing beside him.

"Is that what you thought I'd do?" she mocked him as she laid her right hand over her panties, "finger myself while you watched?"

Kent shrugged, putting a hand on her bare thigh, "Possibly."

"Like this?" Bailey pushed her fingers into her panties, the fabric delving between her lips.

Her eyes closed as she did this, and she exhaled hard as he stroked the inside of her thigh.

Is she going to do it again?

"It feels, different," Bailey spoke slowly, stroking herself, "I did it once, this way."

"When?"

She continued pushing her middle finger into her lips for a while, her back arching slightly, before she changed her movement. Kent watched avidly as Bailey started a gentle rotating motion over her clitoris.

"After you spanked me, one time," Bailey admitted, "Can't remember which time. I think I was looking at pictures."

"Pictures of yourself?"

Bailey nodded, not meeting his eyes. He squeezed her leg with one hand while running the other over her stretched out abdominal muscles.

"Ever put a finger inside?" he wondered aloud, looking at the way her panties shifted

"No," she whispered, shaking her head frantically. "Could never. Do that to myself."

"Oh," Kent whispered back.

Bailey continued to stroke herself with her right hand as Kent rubbed the rest of her body, working upwards until he could make little circles around her nipples. She murmured her approval and her left hand wandered down her body to push her panties aside.

Kent hadn't thought his erection could get any harder, but it somehow managed to swell painfully against his shorts as she exposed herself to him.

If she even touched me right now, I'd come all over her hand.

"You," she whispered, not an accusation but some other imperative.

"Me?"

Bailey opened her blurry eyes and a moment and then ticked her chin towards her crotch, repeating, "You."

Kent laid his right hand over top of hers, three fingertips touching her vulva and the soft hair covering it. He felt her hand, underneath his, working her clitoris.

"Go ahead," she whispered.

"I, um?"

"Just one finger."

Ooooh!

Bailey's lips gave way easily as his middle finger delved wetly between their softened masses and he found her entrance. She moaned, the speed of her stroking speeding up, and Kent pushed his middle finger inward, as slowly as he could. Kent's finger slipped in as far as the first knuckle before the muscles of her vagina constricted around it.

Deep enough, then?

It seemed so, for Bailey began moaning more loudly and frantically hammered at her clit. Her back arched to its maximum as her thighs clamped around his hand.

"Yes!" she screeched out, and Kent properly felt her orgasm clenching and squeezing at his finger.

No question about the authenticity of this one.

When Bailey relaxed again and spread her legs, Kent carefully withdrew his finger, causing her exhale softly with a near whistling sound.

"Is that new?" he asked.

"Something inside me?" she replied. "Yeah."

Bailey turned to glare at him.

"What?"

"Your turn."

=============================

I'm going to keep my brain turned on this time, Bailey told herself. Not going to miss a thing.

"My, uh, turn?" Kent replied.

Bailey jerked a nod at him, "I came twice, didn't I?"

"Yeah," Kent trailed off.

"For you?"

"Yeah."

"And you only paid for one," she pointed out.

"So?"

"So," Bailey rolled her eyes. "You show me."

She saw him get it finally, and noted the nervous gulp.

"You're hard," she tilted her head playfully. "It should be easy."