Two Hundred Dollars Ch. 14

Oh, dear. She's not afraid at all.

Distracted, she didn't sense the eighth spanking coming and it took her by surprise, forcing an entirely unwelcome yelp before she even felt the sting.

"Eight," she chirped.

Her body relaxed then, and she looked back at Laura, still sweating in Kent's chair.

Is she quietly having orgasms during this whole thing?

Bailey turned back to Kent, "Should we do the inspection now, or after?"

Kent laid his hand on her right cheek and squeezed, "Isn't that up to you?"

She shook her head in response. "We choose how the spankings go. You choose how we pose."

"Fair enough," he gave her a last squeeze and then a gentle pat on the rear, "we'll do it after. Together."

Bailey wiggled in his grip to shake him off and stood up.

"How do you want yours?" she asked Laura.

Laura inhaled, coming to her senses, and stood up.

"I think, um," she trailed off, looking around the room. "Kent's way. But-"

Kent waited patiently while Laura examined his room with an uncertain frustration. The room didn't have the size to merit a lengthy search for whatever she wanted, so Bailey didn't understand why she kept scanning the small space. Finally, Laura opened his closet and found what she wanted.

"A stepping stool?" Kent asked. "That's not even mine."

"Why's it here?" Bailey asked.

"Some short person forgot it?" he offered.

"Well, some short person needs it now," Laura carried the plastic prop to the bed and dropped it at Kent's feet. "Out of the way, boy."

Kent obliged and watched as Laura stepped up onto the stool and leaned out over the bed. She locked her knees straight and then brought her upper body all the way down to the bed.

Well, Bailey thought, both eyebrows raising in appreciation, I wish I'd come up with that.

Laura stood a bit shorter than Bailey, but cranking the floor up by twenty centimetres did wonders for the shape of her friend's cheeks, which she'd perched well above the height the bed.

"Good?" Laura turned to Kent.

"Great," he complimented her with clear sincerity.

Bailey bristled, wishing she'd gone second, and carefully took a seat in the chair so she could face Kent in his place at Laura's left side. Even if Laura had turned her game up a little, she could still enjoy watching her get spanked.

"So..." Laura trailed off.

"So?" Kent asked.

"You'll really be able to see a difference," Laura asked, "when you, uh, inspect us."

"Don't worry," Bailey said, meeting Kent's eyes, "he'll make sure."

That's a warning Kent, she thought, we're both expecting you to go just as hard with her as you did with me.

"Here it comes," Kent taunted.

"Mm," Laura replied.

He placed his hand on her left check, deciding that she and Bailey ought to be symmetrical rather than matching. Since Laura had chosen to stand up, she'd made it a lot easier for Kent to go at whichever part of her ass he wanted. And the way she'd perched herself so high exposed absolutely everything.

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Kent understood this part of the game. Whatever else went on between the two girls, he knew exactly what Laura wanted. He smiled, realizing that the competition had already begun between the two of them and they'd only started one set of spankings.

He pulled his hand back and struck the lowest part of Laura's left cheek. A satisfying crack, higher pitched than Bailey's denim provided, echoed around the room.

"Ooh," Laura winced. "Nine. Is that harder than before?"

"It's as hard as I went on Bailey," Kent kept his tone neutral and waited.

Laura looked back at him and gulped before turning away.

"Well," she said, "Go on, then."

He had no intention of letting up, but if she wanted to stop, she knew to say so.

Kent whacked her again, hammering on the same spot.

"Ten," Laura spoke to the wall.

On the third strike, he watched her knees bend as she called out, "Eleven."

Kent glanced over at Bailey, but found her eyes locked on Laura's ass while she held her thighs clenched together.

He struck again and heard Laura moan, her arms stretching out to the corners of the bed.

"Oh, dear," Laura said slowly. "What's that? Twelve?"

"Half way," Kent said. "Are you going to make it?"

"I'm fine," she quipped quickly.

"Because you made three marks on the board," Kent reminded her. "It's early."

Taunting them remained a favourite sport.

"Keep going."

He gave her two shots in a row, slapping the left cheek hard and giving her no time to breathe between strikes.

"Thirteen and fourteen," Laura gasped.

Kent smiled as he looked at Bailey, and this time their eyes met. She smiled back and gave a little chin tick in the direction of her friend's cheeks, as if to say, "Finish her off."

He nodded and slapped her twice more, making the last one harder than any of the others.

"Oh, god!", Laura cried out. "Fifteen and sixteen."

She rose up on her hands, still bent over, and panted. Turning around, she sat down tenderly and looked at Kent.

"You would think," she said and took a deep breath, "I'd be used to it by now."

"Now the end part," Bailey looked at Kent expectantly but didn't rise from her chair.

"Right," Kent stroked his chin and starting imagining how he could arrange them.

The key here is that, when I did this last time, I massaged Bailey's butt where I'd smacked her hardest. She's probably expecting that again, maybe even assuming it's part of the whole deal.

"Alright," he made his decision and pointed to the bed. "Laura here on the right, Bailey over here on the left. Lie on your stomachs."

Part of him had wanted to get them into nicer doggie-style positions, maybe with their legs spread so he could get a good look at them, but he'd decided to save that for later.

I can find a way to see their pussies later if I really need to.

Once both girls had lain down, he crawled over Laura and knelt between them, sitting on his heels. Bailey had to squish over against the wall on the small bed but she made just enough room.

"Whenever you're ready," he said.

The girls looked at each other, shared a brief nod, and reached under their bodies to undo their pants. With some awkward wiggling and hip raising, they got their pants and panties off. He set his right hand on Laura's cheek and his left on Bailey's. He'd positioned them this way on purpose, so that their reddest cheeks would be closest.

"Can you see it?" Laura asked, a touch of eagerness in her voice.

"Right here," he said, squeezing her left cheek hard, eliciting a moan of pleasure of pain.

He squeezed Bailey's cheek, too. She didn't need to ask how she looked.

A curious effect then came to his attention and he had to evaluate the situation before him.

Bailey is wearing tight denim, he noted, while Laura is wearing a loose pair of khaki pants. They still look pretty good on her ass, but they definitely give her more room to move around.

Despite this, however, he could easily see the difference in their poses.

Laura has her thighs clamped as tightly together as she can manage. Bailey, though, is straining as hard as she can to spread her legs apart, even though the wall is in her way.

So while he kept his right hand on Laura's cheek, sinking his fingers in with a deep massage, the left hand on Bailey's cheek he let... wander.

How daring is she feeling right now?

His index finger came around the inside of her cheek, sliding down toward her thigh and under. Laura let out a moan of pleasure, enjoying the massage. But when his fingers just grazed Bailey's short hairs, she let out a moan of an entirely different calibre, her back arching and her legs straining so hard against her jeans that the denim creaked.

Encouraged, two of his fingers wandered across her hair to touch the cleavage of lips, feeling a moistness leaking out.

Bailey let out a wistful sigh and, with obvious regret, gently closed her legs against his touch. He returned to his massage, working both girls over the same way.

"This is the inspection?" Laura's voice had gone soft.

"It was the last time," Bailey sounded tranquil as well, squirming lightly in his grip.

"How long does he get to grope us?" Laura added, as if Kent couldn't hear her.

Bailey shrugged, clearly enjoying her half of the 'inspection'.

I think this just turned into a spa for them.

Kent didn't mind. It became another opportunity to compare their butts, watching the way their muscles worked as they squirmed under his grip.

Bailey doesn't want to come yet, not while Laura is around at least. Maybe later.

"We still have more to do," Laura said.

"Yeah," Bailey agreed. "Alright, Kent. That's enough."

With some regret, Kent gave up his hold on their cheeks, patted both of them gently and dismounted from the bed. As he sat his chair, Laura started working on her pants, carefully keeping the front of her body faced down and hidden while she pulled everything back into position.

Bailey waited until Laura sat up before she even moved. Without making eye contact with either of them, she rolled over on her back, swung her legs over the edge of the bed, planted her feet on the ground, and only then whipped her pants back into place.

She let me see her on purpose, Kent thought, one-upping Laura for sure, almost mocking her friend's shyness.

Out of the corner of his eye, Kent saw that Laura had clearly seen Bailey as well, and he noted the touch of envy in the other girl.

It won't take much longer for Laura to dare some similar act, he knew instantly, and Bailey only did that because Laura got up on the stool.

"Okay," Laura admitted, facing Kent while rubbing her cheek, "I definitely agree that you can make my butt look different with just eight spankings."

"As if there was any doubt," Bailey rolled her eyes and swept her short, reddish hair back over her ears.

"Proof of concept," Kent said. "Although it really depends on the rest of your plans."

"The rest of our plans?" Laura asked.

"He mean," Bailey explained, "it only really makes sense to do an inspection if we weren't going to take off our pants at some point."

"Yeah," Kent agreed, his eyes narrowing dramatically on Laura, "Bailey uses it when she's only doing over-the-pants type stuff that day. But if you were doing that, I suspect you'd have done all three dollars over top of your pants, and done the inspection at the very end."

"Oh, right," Laura nodded, her eyes glazing over in thought. "We could do that. I'll remember next time."

Bailey waited a moment before nudging Laura. "Are we ready for the next round?"

Laura shook herself and nodded, then faced Bailey and let out a little giggle.

"Go ahead," Bailey told her, raising her arms in the air.

Laura knelt down in front of Bailey, fought with the button on her jeans for a moment before getting it undone, then forced the waistband down over her hips, and finally let her pants fall to the floor in a pile of denim. Bailey, now wearing only her blue, athletic pair of panties, kicked aside her jeans as Laura stood up.

The khakis came off much more easily since Laura didn't like her clothing that tight. A moment later, two girls in their panties turned to face him.

"You should know," Bailey faked a whisper to Kent, "she didn't have to change underwear before we came."

"You're suggesting this lacy white thing she's wearing," Kent replied, "isn't normal women's wear?"

"I'm saying, she's started dressing to be spanked all the time."

Laura smacked Bailey on the shoulder, eliciting another awkward giggle between the two of them.

"Alright," Bailey said. "You go first this time."

"Five, right?" Laura confirmed, directing her question at the ceiling.

Her left hand traced over the red spot on her rear.

"Okay, okay," she breathed, her brow furrowing in concentration. "Okay, got it."

She took Kent by the hand and stood him up, then pulled him across the room and settled him in with his back to his dresser.

"Hold me up," she said, "Like before."

Like before, Kent knew exactly what she meant, she wants it the way we did it at the Halloween party.

The difference, this time, lay in her courage. As she bent over his left arm, she put her breast directly into his hand, discarding the coyness with which they'd reached that point on the last occasion.

She's not wearing a bra under there.

The thickness of the sweater had hidden her lack of undergarment, but he felt it now very clearly in the soft, liquid way her breast moved under his hand. He met Bailey's eyes over Laura's back and saw a smile on his roommate's face. She nodded to him and made a claw-like motion with one of her hands.

'Squeeze,' she mouthed to him emphatically, adding a wink.

They talked about this? This was part of 'the plan'? It must have been.

Experimentally, he shifted his grip on Laura's breast, gently rolling it around in his hand, feeling for her nipple. He gave her a good squeeze, drawing a moan from her throat, and laid his right hand on her farther, right cheek -- the only one on which he could get a good spanking angle.

"Ready?" he asked.

"Uh-huh," she breathed shakily.

Timing is everything here. What exactly would make her feel the most here?

He swung his hand back and, just before it came crashing down, he tightened his grip on her breast. That squeeze, done just right, surprised her into tensing up her entire body in surprise, which meant the spanking landed on a tightly wound muscle.

Laura groaned, "Seventeen."

That's it, Kent thought, now she knows what's coming. If she doesn't want to tense up when I grab her tit, she won't do it for the next one. But if that's what she wants, I'll keep doing it that way.

The right hand swung back, the left squeezed, a girl's body tensed up entirely voluntarily, and a swat landed on a fresh, pale piece of ass cheek.

"Eightee-een," Laura moaned.

On the other side of Laura, Bailey smiled cheerfully, nodding to Kent and egging him on.

He continued extracting his dollar from Laura's cheek, spreading the red around instead of focusing it too much. Kent didn't want to wear her out, and he knew they had another set to go.

"Nineteen," Laura said softly when the next one landed.

Her nipple had hardened enough, given his stimulation, that he could feel it through the material of her sweater. Turning his hand a bit, he managed to capture it between his thumb and forefinger.

"Oh-" Laura managed to squeak when he squeezed it, given her just a fraction of a second before he struck her cheek again.

"Twenty," she chirped.

Kent had her nipple then, and rolled it gently, giving her a little twist. Laura panted in his grip, threatening to hyperventilate. He released her for a just a moment, and she sighed in relaxation before he squeezed her entire breast again, delivering a simultaneous slap to the lowest part of her right cheek.

"Oh!" she cried out. "Twenty-one."

She stood up immediately, only to have a regretful look come over her face as she looked down at his hand.

She wanted more of that, Kent thought with chagrin, at least the tit-squeezing part. So did I, but the moment's lost now.

"My turn, my turn!" Bailey hopped up.

"And what do you want?" he asked.

She sat on the bed and looked at him, "Remember the offer Laura made?"

"Which one?"

"Two extra spankings," Bailey clarified, "But she tells you which side to do it on?"

"I remember," Kent nodded.

Bailey looked at the floor, her teeth clicked against each other twice in thought, and she shook her head.

"No," she said, still looking downward thoughtfully. "No. I owed you two hundred bucks, right?"

Kent nodded.

"And this whole 'offering my butt' thing was my idea," she added, now looking at Laura. "So if you want to spank the sorest part, that's... well, that's only fair, right? I have to pay off my debt."

Laura's lips twisted slightly and she sighed.

Without waiting for anything else from Laura, Bailey turned around, stepped up on the stool and bent over the bed until her breasts touched the bedsheets.

She, at least, is wearing a bra, Kent noted the perkiness of her breasts as she leaned over. But wow, look at what she's offered.

With her back arched and her legs up so high, the muscles of her rear had stretched and tensed. He could clearly see, even in the room's dim light, the two reddest parts of her ass. The left still bore the marks of the thirty spankings she'd taken the night before, but the right glowed freshly red with today's efforts.

And she just basically told you that she wants five more, right there.

Kent checked his peripherals, noted that Laura watched with wide-eyed shock bordering on horror.

The stool, though, is brilliant. It's even better with a naked ass than a-

"Too bad we don't have a second stool," Bailey said, moving her feet to the edges. "We could put them farther apart."

Oh, god, she's killing me.

He took his spot to her left and laid his right hand on her right cheek.

"You ready?"

"Another day," she quipped, "another dollar."

Egging me on.

He struck without hesitation, slapping at her cheek just above the reddest part.

Does she want that one spot to hurt even more? Or should I make the spot bigger?

"Yes," Bailey hissed, and followed with a moaned, "Twenty-two."

Alright, then.

He moved his hand lower and slapped her again.

"Twenty-three."

Hard and fast, is that it?

Kent delivered two more hard cracks off her ass.

"Oh, god," Bailey shivered. "Twenty-four and twenty-five."

"Last one," he warned.

She pushed her cheeks out at him, waiting, and he delivered a final sharp strike.

"Twenty-fix," she breathed, and rolled onto the bed on her back. Her hands went to her panties, pressing down on her lips as she moaned.

Kent watched her body heave, wondering if she planned to make herself come.

Would she really masturbate right in front of us? Maybe. Both girls obviously have a bit of exhibitionism in them.

After a few gasps, however, Bailey got herself under control.

"You two need a minute?" Laura let out another giggle.

"I'm fine," Bailey admonished her friend with a glare, not altogether convincing given the heavy blush running through her entire face.

Bailey rolled out of bed gingerly, then sat back down, carefully supporting her body on the least abused part of her cheeks, leaving the lower, reddened parts hanging over the edge. She crossed her ankles and faced Laura.

Kent looked back and forth between them, wondering what they had planned next, but the girls only looked at each other. When he shifted his stance, nursing an uncomfortable erection, it broke the spell. Laura stood up and drew him over the to chair, bade him to sit. She then dropped down in his lap.

"Oh?" she blurted out, then wiggled in his lap.

The tip of his erection, through his pants, poked directly between her legs. She moved her body around a bit until the bulge settled against her a bit less intrusively.

"Well," she sighed, then inhaled and looked at him. "Okay, let's put that aside a moment."

"Put what aside?" Bailey chided her.

Laura frowned, clearly having trouble deciding how she wanted to describe her situation. Instead of speaking, she just twisted her ass in his lap, causing Kent to groan.

"That," Laura said with a roll of her eyes.

Kent put his arms around her, interlacing his fingers around her bare hip, half under her sweater.