Two Hundred Dollars Ch. 09

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Securing her man before she takes a long weekend.
6.3k words
4.85
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Part 9 of the 29 part series

Updated 06/09/2023
Created 09/14/2018
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xtorch
xtorch
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162 Dollars

Their schedules having collided horribly on Tuesday, with Kent getting stuck in some sort of post-project analysis with his horrid group-mates for the afternoon and Bailey having her evening booked up by some massive Physics demonstration everyone in her class had to attend, they didn't have a real chance to get together until Wednesday evening.

Carson, unfortunately, also came home and seemed intent on hanging around.

There are only so many times, Bailey reasoned, that I can go into Kent's room, close the door, crank up the stereo and not arouse suspicion.

So Bailey remained in her room, with the door open, hoping she would catch Carson leaving at some point.

Maybe he'll go for groceries, take off for a walk. Any damn thing at this point would be fine.

She found herself twitching hopefully every time a door closed, or that stupid bouncy ball he used instead of a chair creaked. The guy went for snacks in the kitchen, got himself water, did everything except leave the apartment.

Bailey tried not to panic, did her best to calm herself and keep her breathing even. She had no reason to rush through the matter. Any day which didn't give her a chance to pay back some of her debt just meant she paid back extra the next day. Her butt, she had conclusively proven, could suffer at least $3 every day.

She forced her body to relax, every muscle in her back and shoulder all the way down to her calves and her curled up toes.

Everything is fine.

Relaxation would have come easier if she could have played some music to herself, one of those streams supposedly designed to help you calm down and study. But, wanting to demonstrate courtesy to her housemates, she'd have to either close the door or put her earbuds in.

If I do either of those, I might miss Carson leaving, she frowned to herself, and I can't risk that.

The bouncy ball squeaked down the hall in Carson's room as he stood up. The ball bumped up against something and she heard Carson opening a drawer.

Is he leaving?

A moment later, she caught him, out of the corner of her eye, walking down the hallway, towel in hand.

Shower? He's taking a shower? Bailey's heart thumped in her breast. Is that enough time?

She decided it would have to do.

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

Kent had, likewise, spent a lot of time thinking about spanking Bailey for the past two days. Her offhand comment about a "blank canvas" had spurred a part of his brain into considering all the ways he'd spanked her and Laura over the past month.

He'd always looked at it from the perspective of their pain, discomfort and how embarrassing they found it to pose. If it seemed like one of them wanted more force used, in that sort of obviously ironic way they both had of complaining about him focusing on one part of their ass cheeks, he would continue to target one spot. When it began looking like he'd pushed them to their breaking point, Kent picked another spot.

He had also spent some of his energy trying to surprise the girls, so that the spanking, while not especially painful, might still shock them. As well, the idea of striking them in places that would cause later discomfort -- sitting down, obviously -- ranked high in his priorities. He wanted both Bailey and Laura to remember their spankings, to keep his actions, and their acquiescence, prominent in their minds.

In all that time, though, in all his horny rushes to get at their asses, he'd never really given a thought to how they looked afterwards.

For these reasons, when Carson locked the bathroom door and Bailey popped into his room a second later, breathlessly locking the door behind her, his heart did a skip, too.

"Hello," he said.

"A quick one?" Bailey asked.

He nodded and she put a mark on the board. A moment later she'd undone her jeans and dropped them on the floor in front of his door.

Kent inhaled in surprise. No matter how many times he'd seen her transparent white panties, the site of it still shocked him.

"I don't want to still be in here when he's done," she jerked her head behind her, indicating their house mate, "Too obvious."

Kent nodded in agreement, biting his lip, and Bailey walked past him to bend over his bed, putting first her elbows down on the bed sheets, then changing her mind and lowering her breasts all the way down to its surface.

"Nice," Kent complimented of her perched rear, seeing the thin band of her thong embed itself between her cheeks.

"What's nice?" Bailey's voice quivered with what Kent took for sarcasm.

The best part about this position, with her hips up higher than any other part of her body, lay in the fact that he had full and easy access to any part of her cheeks.

"Oh," Kent replied as got out of his chair and approached her. "I can still see the pink marks from Monday."

He drew a line with his fingernail, gently dragging it from the upper part of her right cheek, across her ass, to the lower part of her left.

"Still faintly there," he said. "Can you feel it?"

Bailey shrugged, "Maybe a little."

"What about here?" Kent scratched at the paler portion of her left cheek.

"A little less... sensitive, I guess."

"Mm," Kent thought carefully. "Ready?"

"Yes."

He made his decision then and slapped his palm down hard on the palest part of her left cheek.

"Ha!" Bailey hissed out. "One."

Kent struck the same spot again, watching her flesh go from pale white, to pink and then to red.

"Oh. Two."

He handed out a third spanking the same spot. The flesh there now stood out more red than the pink remnants of Monday's spankings.

"Three," Bailey said.

Without further warning, he struck at the untouched flesh of her right cheek, low where he hadn't touched it. Knowing he only had two spankings he could deliver there, he went even harder than he had for the left side.

Bailey moaned for a couple of seconds at this, and Kent wondered if he ought to take a bit off.

"That'll be red," Bailey whispered. After a deep inhalation, she added, "Four."

There's a subtle hint, there, Kent realized. A line between encouragement and discouragement.

As it stood, the newly struck flesh of her right cheek matched the colour of the pink slash. He needed one more good strike to get it as red as the part of the left he'd just worked on.

"I can make it redder," he kept his voice halfway between offer and threat.

Bailey took a deep breath. "Your dollar," she said, pushed her hips back toward him.

Kent knew he didn't have to hold back then, and slapped her right cheek with the same power he'd just used. The slap echoed in the room and Bailey bent her knees, wincing and groaning as her body twisted.

"Five," she said, adding almost instantly. "How do I look?"

"Pink," Kent smiled, touching the centre part of her cheeks. Moving to cup both cheeks with both hands, he added. "And red. Quite a bit of red."

Bailey stood up, touching her hot flesh with her fingers, feeling for the new sore spots and comparing them to untouched, pinker areas.

"Nice," she said, with a touch of what Kent took for admiration.

"Just one today?" he asked.

Bailey turned around and walked past him, punching him in the shoulder as she passed, "Yeah, I'd rather Carson not, y'know, know about this."

"Right," Kent drawled in return, then raised an eyebrow as he watched her do the strangest thing.

Given the shape of the human body and all the possible arrangements its owner could put it in, what with all the joints and all their degrees of freedom, a girl could pick up her clothing off a floor and redress herself in any number of ways.

In Kent's mind, however, Bailey had made a decidedly decision, a choice which almost looked awkward.

She walked to her jeans, still in a pile of denim by the door, stepped past them, then turned around to face Kent. He had expected, if Bailey still felt like shining him on, that she would bend over in front of him while facing away.

Maybe I've just spanked her so many times, Kent thought, that I'm used to seeing her that way.

Still, the movement and pivot seemed awkward to his eye, an ungainly choreography. Bailey stepped into her jeans, then leaned over, facing him, her knees unbent, and slowly pulled them on. Looking down her loose sweater, he realized with a bit of shock that she wore nothing underneath -- neither shirt nor bra. From his viewing angle, he saw the cleavage of her little breasts, jiggling slightly as she worked the jeans on. As she twisted, one of those little mounds came fully into view, its dark red nipple clearly visible even in the room's dimmed lighting.

As Bailey stood up, she looked directly into his eyes, a gaze full of inquiry and concern.

Kent raised his eyebrows at her as she buttoned herself up, as if to ask her what she was asking.

She shrugged back, unlocked his door, and left the room.

No matter what's going on here, Kent thought as he sat back at his desk, whether it's her, or her together with Laura. No matter what. I always feel like I'm three steps behind and I have no fucking clue what's going on.

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

Bailey closed her door behind her, safe and secure in the knowledge that Carson had heard nothing from under the spray of the shower's water. She disconnected her camera from the Internet, dropped her jeans and her panties so she could look at herself in the mirror. Forced to make do with artificial lighting, she worked the mirror as best she could.

The pictures, however, came out majestic and, furthermore, worth every bit of prodding she'd done to get Kent to deliver that last sharp slap.

She had a perfect red slash across her rear, a testament to the eighteen spankings she'd taken on Monday. This Kent had highlighted by turning the upper left and lower right parts of her ass into a bright, fresh red.

Bailey kept two pictures of that, stashing them away in a safe folder.

Next, she went to her notebook, adding the very simple notation for her five spankings that day.

She sat in her chair, slouching down to grind the sensitive parts of her cheeks into the rough fabric of the seat, leaving herself perched on its edge.

I don't need the pillow tonight, Bailey realized as she pushed her fingers between her lips. Now, about that look down the shirt I gave him...

She couldn't come to a conclusion as to what it had meant to Kent. She knew there was no way, given the low cut of her sweater and the amount of jostling and twisting she'd done, that he hadn't seen at least one of her breasts.

But did he care? Did he look? Did it matter? Was he excited?

Grinding into herself with gusto, she realized she couldn't tell. Observing him caused him to know she observed him, which caused him to change his behaviour. If she could hide her phone in his room and make a video that captured his expression while he didn't realize it, then she could get his honest reaction. But she had no intention of making a spanking video which contained any identifying information.

What I need is a friend to watch him while I flash my boobs at him, Bailey realized, making little circles around her clitoris.

But she couldn't ask Laura - couldn't ask her friend with larger breasts to help her get over her issues with her own smaller breasts.

It didn't impede her orgasm, but she spent the rest of the night wondering what Kent thought of her.

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

Her problem throughout Thursday lay in living with the consequences of having encouraged Kent in delivering those hard, low spankings. In the end, she just decided to sit down, whenever sitting became necessary, as quickly as she could and savour the sensation while trying her best not to let any of her classmates see her wince.

That said, she arrived back at the apartment Thursday evening to find herself still extremely aroused by the soreness of her cheeks. Kent sat furiously typing away at his PC, and Carson's room stood empty.

Bailey decided immediately that she didn't care where Carson had gone or for how long. His lengthy stay the previous evening had made her value these moments all the more. She ditched her backpack in her room and walked on to the kitchen. With a deep breath and a deeper determination, she snatched the wooden spoon from the drying rack and went immediately to Kent's room, still wearing her jacket and boots.

"Hey, Bailey," Kent said, a bit distracted. "I, uh... whoa, really?"

She'd interrupted him in mid-sentence by holding out the wooden spoon. Without a word, she made two tick marks on the board before handing the spoon to him.

"No more than half with the spoon, okay?" she explained.

"Okay," Kent replied slowly, "but why at all?"

"What?" she asked, unbuttoning her jeans and revealing a blue pair of panties.

"The deal is for spankings with my hand," he explained, watching her kick her boots aside. "If the spoon hurts too much, why at all?"

Bailey twisted her lips thoughtfully and then turned away to climb up on his bed. She had decided, this time, to show him something a bit different, and put her knees up on the bed before bending over, waiting for Kent on her hands and knees. It wasn't much different from what she'd done with Laura, except she didn't have Laura beneath her to straddle.

"Nice pose," Kent complimented her.

"Woof, woof," Bailey replied sarcastically.

"But you didn't answer the question."

Bailey turned away, facing the wall, jogging her head side to side in thought. Kent sat on the bed on her left side, lining up his right hand with her cheeks and began running his hands over the pink and red portions of her flesh, waiting patiently.

"I guess I want to see what you'll do with it," Bailey told him.

Kent inhaled sharply through his nose, and Bailey hoped she'd cleared the matter up for him.

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

Kent surveyed Bailey's ass once she'd turned her back to him again. The way she'd bent her hips and knees had stretched out her panties and mostly tucked them out of the way between her cheeks, letting him see most everything a thong would have shown.

He could still see the pink slash across her rear from Monday, but it had mostly disappeared and existed only in contrast to reddish tinge on the upper left and lower right. Here she'd given him a chance to expand on his previous efforts, and offered him a tool.

The spoon, he knew from her previous reactions, hurt quite a bit more. But Bailey had, for reasons he couldn't completely understand, offered it anyway.

But where should I use it? And how? he wondered.

Even though he found the stinging sensation in his own hand to bring a great deal of satisfaction, Kent also liked the effect the spoon had and the mark it made. Done properly, obviously, Bailey might allow its use again. He needed to tread carefully.

He examined her thoughtfully, touching here and there to gauge her reaction. Did she have something specific in mind? It didn't seem so, for she made vaguely appreciative noises wherever he touched her.

"Before Carson gets home?" she admonished him after a while.

"Right."

With that little boost, he suddenly came up with an idea. He hoped she liked it.

First step: freshen up the dark spots.

He delivered three hard spankings to the darkest parts of her left cheek, the upper most part, spreading the redness around so it wasn't the exact same spot, but still mostly confined to the upper left.

"One!" she shouted. "Christ! Two! Ah! Three!"

Gasping for air, Bailey looked back at him with wide eyes.

He raised an eyebrow, waiting for some kind of comment.

Instead, she sucked in her breath and turned away.

Quietly, Kent drew the wooden spoon, lined it up with the very centre of the redness he'd just created, and let her have a stinging swat.

She sucked in air, hard, just like he remembered from the last time, and breathed out, "Four."

Kent put the wooden spoon in his left hand, then laid it on the bed right next to her head so she could see it.

He then put his hand on her right cheek, on the lowest part, the part that he'd reddened the night before. Bailey, understanding his intention instantly, shivered as if a cold breeze had just run through her body.

"Uh-huh," she murmured.

Three more spankings struck her right cheek in rapid successions, with Bailey moaning from beginning to end, holding back the counting until several deep breaths later.

"Five, six, seven," she said quietly through gritted teeth.

Her head turned a little toward, her eyes clearly on the wooden spoon. She had to know, now, what Kent had planned.

He took the spoon, transferred it to his right hand, and gently patted it on lower right part of her cheeks. Bailey inhaled just as the spoon whistled through the air and struck her.

She sucked air again and said, "Eight."

Kent stepped off the bed and took a look at what he'd done. The pale pink slash still existed, but the red areas had grown redder, and each now hosted a sharp, slightly darker red oval in its centre.

Now to finish this off.

He sat beside Bailey again and lined the spoon up on the high part of her right cheek, the pale pink part of her flesh. The spoon whistled again and struck the fresh flesh.

Bailey's response came faster this time, a defiant, "Nine!"

He went low on the left with his last strike.

"Ten!" she shouted triumphantly.

"Now you know," Kent said.

"Know?"

"What I'd do with it."

Bailey nodded, "Alright, I gotta see this."

She checked both ways in the hallway and ducked into the bathroom. Kent followed, carrying her jeans, and leaned against his doorway while he watched her. Bailey turned her back on the mirror and stood up on her tiptoes to look at her cheeks in the mirror.

"Crazy," she whispered, turning side to side. "Oh, my pants?"

"Mm-hm," Kent tossed them across the hallway to her and watched her pull them on.

"Later, Kent," she passed him by and went back to her bedroom.

"Later, Bailey," he replied as she closed her door.

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

Bailey had a tight schedule Friday afternoon.

Her last class ended at half past two which she knew would work out fine. It meant, if she moved her butt back to the apartment, she'd have plenty of time to grab the large carry-on she'd already prepared and catch the bus just four blocks from their apartment and then head home for weekend at four o'clock.

As the minutes on the clock ticked by, she tried to focus on the lecture but her thoughts kept straying.

What if Laura comes by while I'm gone?

For this, another part of her mind chastised her, She promised and she won't do that. Trust her.

But as the second hand on the ancient wall clock swept around, minute after minute, the thought began to occupy and eventually conquer her brain.

I can get back to the apartment fast enough, Bailey decided, I have an hour and a half.

If she could sate Kent's hunger, slake his thirst, might that suffice to keep him and Laura apart for three whole days? She'd return Monday morning, after all.

Three days without a spanking, she exhaled through her teeth, How will I handle it? How will Kent?

Bailey made her decision. She needed to get to him one last time before she left for the weekend. If not, she'd worry about him the whole time of her absence.

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

Kent, desperately seizing the opportunity presented by the oddly warm weather that late October afternoon, had chosen to go for a run. Running outdoor felt a lot better than using a treadmill while staring at a television his eyes could never track properly. Plus, if he ran in the gym, he always had to contend with a bunch of people around him.

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