Two Hundred Dollars

"Now?" he murmured.

"Why not?" she said.

"Alright," he sat up. "How do -"

"Wait," Bailey held up a hand. "You said it's only five if I pull my pants down, right?"

Kent felt a stirring below.

"Ri-ight."

"Just a sec," she said, and quickly left the room.

About half a minute later, she slipped back in and closed the door.

"Okay."

He sat on the edge of the bed with his legs on the floor and she crawled over into his lap. Underneath her body, he felt her unbuttoning her jeans while coincidentally grinding her knuckles against his partial erection. Bailey unzipped her fly and pushed the waist band of her jeans down at the sides, revealing a nicely cut pair of solid black panties.

"Far enough?" she asked.

"A little more -- get past your cheeks."

She obliged, pushing until the bottom of her cheeks were visible. "Good?"

"Uh, yeah."

"Uh, yeah," she mocked lightly, "I can feel you poking me underneath."

Bailey then lifted her hips to get away from his erection, exposing her cheeks a little better.

"How do you want to split them?"

"Split what?"

"The five spankings."

"Oh, that," she said. "Just do them on one side. We'll switch next time."

Kent reached out and laid a hand on her right cheek, his thumb over her panties and his fingers on her bare skin, giving her a little squeeze.

"Ahem," she snarked. "The deal was spanking, not groping."

"Right," Kent replied. "Ready?"

She nodded.

The sharp tone in her voice had brought out the best in him. He laid a hard smack dead centre on the part of her cheeks unprotected by her panties.

"Oh, you bastard," she retorted. "One."

"Too hard?" he asked.

"Screw you," Bailey replied, taking his remark for a taunt.

He let her have another strike, just as hard, but up higher where her panties covered her.

"Mm," she groaned. "Two."

"Panties don't help much?"

"Shut up."

A third whack.

"Three," she groaned in exasperation. Then, "Four!"

He let her have a last, solid whack right on the underside of her cheek, so she'd remember this when next she sat down.

"Five. Hah," she shouted and let her hips relax, falling into his groin.

She stood up immediately and looked down into his lap. "Turn on for you?"

"Yeah, it is."

Bailey eyed the bulge in his shorts. "Do you jerk off after?"

"Sometimes," he said. "Depends."

"Hmph," she replied, and pulled her pants back up before turning and leaving. She closed the door behind her.

Masturbating seemed like a good idea then.

He didn't see her again until late Saturday night. With only a severely dimmed light on in his room, he'd left the door open again while he played an RPG past midnight. He was in the middle of a hectic battle when he heard the upstairs door open, close and lock. Footsteps tapped stealthily down the stairs and paused outside his bedroom door. Kent ignored them, deep in an online battle with friends counting on him.

The door creaked open and he heard clothing brushing past the doorway. The virtual battle raged on as he delivered healing spells to desperate guild mates. In a corner of his awareness, he heard Bailey making two marks on the whiteboard.

"Just a sec," he told her. "Battle's almost over."

"Okay," she whispered, apparently patient.

Eventually, the oversized Ogre and his cadre of Orcs fell before the combined might of his guild and he signed off, trusting his guild mates. to share the loot properly.

Kent turned his chair around to deal with Bailey, and stopped short as he saw two girls in his room.

"Laura, was it?" he asked the girl with the long, dark hair.

The girl nodded. She was a bit heavier than Bailey, but that went for most of humankind, and she had breasts like Bailey didn't. Her features ran a little more rounded, where Bailey had sharp edges.

"You brought an audience?" Kent checked the whiteboard, confirming the sound he'd heard.

"Not exactly," Bailey said, carefully toe-heeling her way over to the bed. "Sober, see?"

"Uh-huh," Kent replied dubiously, eyeing Laura.

"I owe her a favour, alright," Laura said. "So she told me what she was doing, and I -- I wanted to help."

"Help?" he asked, then turned to Bailey. "You actually told someone what we're doing?"

"Help," Bailey confirmed as she sat on his bed. "I'll do one and she'll do one."

Kent turned back to Laura. "You're signing up to be spanked here. You know that, right?"

Laura giggled. Both girls, he realized, had been drinking. 'Sober' was a relative term.

"Alright," he resigned, "Who's first?"

Laura said, "Bailey" at the exact same moment Bailey said, "Me."

As Kent moved to the bed, he asked, "Jeans up or down?"

"Oh!" Laura exclaimed, "you said it was -"

"It's ten on top," Bailey spoke quickly. "But, um, five underneath."

"Oh, well. I'll do it on top," Laura said. "You didn't even mention -"

"I know," Bailey soothed her. "It's fine."

Bailey laid herself over his lap and twisted her hips to present her left cheek better to his right hand.

"Like that?" Laura sounded surprised.

"Yeah," Bailey looked at her. "How else?"

"Oh, that's fine," Laura said.

Bailey looked back at Kent in the dim light and nodded.

He delivered his first spanking to the lowest part of her left cheek.

"One," she said calmly.

A desire seized Kent, that he should make it hard for her to sit down in the morning, and he struck the same spot again.

"Two," she winced, then, "Three! Four! Five! Okay... okay... the left side."

Occasionally, Kent looked up at Laura, who stared in fascination at her friend's rear. For one spanking, he looked away from Bailey's body to see Laura's reaction at the moment he struck. The girl bit her lip with each strike he delivered.

"Nine... and... Ten!" Bailey announced.

She stood up, rubbing the underside of her cheeks. "Thanks," she told Kent. "I won't be able to sit for the entire weekend. How do I explain it to my parents?"

"You're going away?"

"Yeah, just until Monday."

Kent knew that Bailey had arranged her schedule to have no classes until late Monday afternoon, just so she could take weekends like this.

Bailey turned to Laura, "Still want to take one for me?"

"I -- yeah, sure," Laura stammered as she walked over to Kent.

Kent held up a hand and stopped her more directly, almost putting that hand on her stomach. "Are you sure?"

"Yes," her voice came out steady and confident.

"What did you mean when you asked 'like that'?" he asked.

"What?"

"Before, when Bailey laid down," Kent replied. "You said 'like that?' What were you expecting?"

"Oh, nothing, nothing."

"Honestly, what was it?"

Laura sighed and looked up at the ceiling. "I just didn't think that was how you did it."

"How did you think I did it?" Bailey interjected.

"Well, you know," Laura wiggled her head side to side. "Sort of... well... bent over."

There was a pause then and Kent realized he'd let Bailey dictate how they handled the whole thing, from a mechanical point of view.

"Well," Kent said. "It's your butt. How do you want it to be?"

"Well, it doesn't matter," Laura flustered. "It's just the way... y'know... when I was a kid."

"If you want it that way," Kent said softly, still sitting down patiently. "Just show us."

Laura looked at Kent's lap, then at Bailey.

"This is embarrassing," she declared.

"If you don't want -," Kent started.

"No, no, it's fine," she waved him off. "Here, like this."

She turned her back on him, stuck her ass out in his direction, and put her hands on her knees.

"This is how you were spanked as a child?" Bailey asked.

"Yeah, my mom and my dad would make me stand like this."

"When were you raised?" Bailey asked. She shifted her stance and her tone turned almost maternally judgmental. "Was it the 1950s?"

"It was Utah, alright?" Laura complained.

"That's how you want it?" Kent asked, eyeing the way the khaki material stretched over her cheeks.

"Yes," she said. "Go ahead."

Kent stood up, moved to her left side and laid a hand on her left cheek. "Here?"

"Just like Bailey," Laura said. "Five on each side."

"You should count," Bailey said, taking a seat on Kent's desk chair, right in front of Laura.

"I know," Laura rolled her eyes. "You told me already."

She took a deep breath, waiting expectantly.

Kent squeezed her cheek first. Bailey had taken this for a grope, which it was, but it also performed as a check, to make sure she hadn't slipped some padding under her clothes. In truth, Laura's khakis would protect her a lot less than denim.

He pulled his hand back and let it fly, striking a loud, high pitched snap off her left cheek, a much different sound from than he produced against denim.

"Ooh," Laura huffed. "One."

He struck again, trying to find a sweet spot where he could catch a lot of flesh at once.

"Two", she hissed out.

Kent moved lower, gave her two in rapid succession on the lower part of her ass.

"Three, four!"

He gave her one more hard whack, just above the thickest part of her butt.

"Five!" she cried out. "Now the other side."

Kent moved in closer, brushing his pants up against the side of hers, so his right hand could reach across her body to get her right cheek. This he squeezed and caressed too. Unlike Bailey, Laura didn't complain.

"Ready?"

"Mm-hm."

He decided to focus on one spot this time, striking low under her right cheek over and over again.

"One! Two?" she cringed. "Ooh, right where I sit... three!"

As much as she complained, Laura never wiggled or moved her hands from her knees.

"Four!" she cried out.

When he paused for a moment, she looked over her shoulder. "Well? Finish up."

He let her have one more, hitting her harder than all the spankings before, square in the centre of her cheek.

"Ow!" she called out. "Five."

As she straightened up, Kent looked at her.

"What?" she asked.

"You never flinched or moved," he said. "Not even once."

"I... well... no," Laura stammered.

"Your parents trained you that way?" Kent asked.

"Yeah, I guess so," she said. "You weren't allowed to move when you got spanked. Didn't your parents spank you?"

Bailey shook her head. Kent said, "No."

"Well," Laura puffed out. She turned to Bailey, "Are you all caught up now?"

"Caught up?"

"You said you fell behind," Laura said. "And I owed you a favour, to help you catch up. So you're caught up now?"

"Oh, right," Bailey murmured.

"Bailey missed Monday, Tuesday and Wednesday," Kent explained, "But she did Thursday and Friday."

"But today's Saturday," Laura sighed in exasperation. "So you've still got today and Wednesday to do?"

Bailey's eyes came back into focus and she stared at Laura.

"Stupid," Laura chided Bailey. She walked over to the white board and grabbed the marker. "What do I do? Put two more marks here?"

"Um, yeah?" Kent looked at Bailey in confusion. Bailey shrugged in helpless reply as Laura made two more tick marks in red marker.

Laura returned and took Bailey's hand. "Come on. You're first, right?"

She tried to pull Bailey upright and gave her confused friend a nudge toward Kent.

"Well, okay," Bailey said.

"Tell you what," Laura said. "You try it my way and I'll try it yours."

Bailey shook off her bafflement and looked at Kent. He raised his eyebrows and shrugged.

"Okay," Bailey agreed and turned her back on Kent, bending over to put her hands on her knees.

When he touched her left cheek, she suddenly stood up straight, "Wait."

Kent withdrew his hand, "What?"

"Five underneath, right?" she asked.

"Sure," he said. "But do you want to do that with your friend watching?"

"Yeah. Why not?" Bailey shrugged

She unbuckled her jeans, unzipped them, and pushed them down. She wore a pair of dark blue panties this time, shaped with a bit more of an inward curve so they sloped down to a very thin section at her crotch. They covered almost none of the parts of her cheek he wanted to spank. Even in the dim light, he could see that both of her cheeks were red from the spankings he'd already delivered.

As Bailey bent over and touched her knees, her jeans fell farther down her body, only the stiffness of the material stopping them about halfway down her thighs.

Kent put his hand back on her bare left cheek. "Ready?"

"Go."

The sound his hand made slapping her flesh was even higher-pitched than the when he'd spanked Laura through her khakis. A delicious snap echoed through the room.

"One."

"Do you think you'll be able to sit down tomorrow?" he asked.

"Depends if you go lower or not," she kept her voice calm.

Laura came around and sat on the bed. "Okay if I watch from behind here?" she asked.

Bailey looked over her shoulder and said, "Whatever."

Kent pulled his hand back and slapped her cheek again, low and hard.

"Twoooo," Bailey whistled softly. "You're trying to make it so I can't sit down?"

"Isn't that what you asked for?"

"Hmph," she replied.

A third slap echoed in the tiny bedroom.

"Three."

"Sooo red," Laura commented.

Kent delivered his fourth strike, charitably striking higher. It didn't get the same reaction, but the vibration travelled through her bare flesh most deliciously.

"Four," Bailey remarked. "At least that was a different spot."

"I'm going low again, for the last one."

"Okay," Bailey bit her lip.

Figuring it his last shot, he let her have it low and hard, letting his fingertips catch and graze off the uppermost part of her thigh.

"Five," Bailey breathed out in relief. She gingerly pulled her pants back up, buckled them, and carefully sat down on his -- thankfully soft -- desk chair.

Kent sat back on the bed, admiring the look on Bailey's face. At least he felt like he was getting his money's worth out of the deal. It wouldn't make sense if it was easy for her.

"Across your lap?" Laura asked, sitting next to him but not moving yet.

"However you like it," Kent reminded her. "Or not at all, if you don't."

Laura hesitated. "No, I'll do it. But, um -"

She stood up and leaned over to whisper something in Bailey's ear. Bailey's eyes widened and her eyebrows went up.

"I don't know," Bailey replied. "We never -- um -- Kent?"

"Yes."

"What if she does it, you know, bare?"

"Bare?"

"Like, naked," Laura put in.

"Naked?" Kent asked. "Like all your clothes off?"

Laura held up both hands, palms facing him and frantically waving, "No, I just mean, my panties pulled down too."

"Oh," Kent said. "I was going down to three if you're naked. But, bare-ass, okay... let's say four."

"Just four?" Laura asked.

"This is about paying for money owed," Kent explained. "Like a punishment, sort of. And spanking a bare ass isn't much different from panties."

Laura leaned over and whispered in Bailey's ear again.

Bailey nodded in sympathy and stood up. "We'll be back in a moment."

The two girls quickly slipped out of the room and went next door. It took Kent a moment to realize what the girls had gone to do, once he remembered that Bailey had done something similar the first time she'd pulled her pants down for him. Laura, he realized, hadn't thought she'd be showing her underwear to anyone tonight. Consequently, she'd worn boring underwear she didn't want him seeing. He thought it a very strange anxiety for someone getting spanked.

If he had it right, Laura had access to Bailey's underwear drawer and picked through her offerings while he waited.

"Okay," Laura said, entering ahead of Bailey. "Ready."

Bailey sat down in his chair too quickly, winced and hissed, then seated herself more carefully, whispering, "Bastard" under her breath.

Laura, unlike Bailey, unbuckled her belt and unzipped her pants while still standing in front of him. Once she had them undone, and the little red lingerie tag was sticking out above the waist of her pants, she got up on the bed and laid herself over his lap.

"Like this?" she asked, and pushed her khakis down until her cheeks were uncovered and a pair of red panties, probably Bailey's, were revealed.

"Push it down a little farther," he told her, "So I can see your whole butt."

Laura wiggled a big, inching her pants down. The red panties were edged with lace and dove between her cheeks, obviously a little too snug for her more generous frame.

"Which side?"

"Um," Laura hemmed. "Maybe go back and forth?"

"Alright," he said, and nudged at her hips. "Lift up a little so I can get the closer side."

She lifted her hips, given him a better look at her, and he tilted her a little away from himself as he laid his hand on her right cheek -- the one farther away.

"Ready?"

"Uh-huh."

He slapped her hard and low, watching the undulation move up her cheeks, shaking the panties.

"One."

Kent squeezed her left cheek and let her have one low and hard there too.

"Two," she said.

Back to the right. He gave it to her higher, just to watch how differently her muscles shook. Bailey was skinny, but Laura had just enough weight on her to give a nice wave of flesh.

"Three."

On the left, he struck dead centre, observing a similar vibration.

"Four," she said. "Are you trying to make me red everywhere?"

"Yes," he admitted, "But I think I want you to remember me every time you sit down."

Bailey snickered, but Laura said, "Do it lower, then."

He gave her right cheek a good squeeze, then spanked her hard on her upper thigh.

"Hooo," she whistled and stood up in sudden reaction, saying, "Five."

But she'd been in such a hurry to stand, she hadn't grabbed her pants, so they fell down to her ankles, giving him a good look at the scant coverage Bailey's panties gave her pubic triangle. Kent, therefore, discovered that Laura kept herself trim, but not shaved, through the transparent portion of those borrowed panties. Slightly embarrassed, she pulled them right back up, giving Kent a good look down her shirt at her breasts and the white bra that contained them. If not for the dim lighting, he imagined that, with such a loose bra, he might have seen her nipples inside the cups.

A moment later, she had her pants back up and started work on the buckle.

"Well," Laura said as she zipped up, "I promised to get you caught up. Are you sure you're caught up now?"

"It's Saturday," Bailey said, "I was behind by 3 days and I'm caught up."

"Although you're going away tomorrow," Kent pointed out.

Laura glared at Bailey again, "So you'll fall behind again?"

"Well -" Bailey stammered. "I can just catch back up on Monday."

"No, no!" Laura waved a stubborn finger in the air. "I won't have you saying I didn't keep my promise, or that I still owe you one."

"I really -" Bailey stood up to block Laura as her friend brushed past her and took the white board marker.

"One more," Laura ticked it off on the board, "Together. Then we're done."

Bailey looked at the mark in exasperation. "But my ass -"

"What sort of favour does she owe you?" Kent wondered aloud.

Bailey sighed in admission, "I did help her out. It was kind of a big deal."

"Okay," Laura ignored Bailey's declaration. "Your way or my way? We'll do five each."

"I don't know," Bailey shrugged, fully exasperated at this point.

"What about Kent's way?" Laura turned and looked at him.

"My way?" Kent asked. "I'm not sure Bailey even wants -"

"No," Bailey put in. "I'm fine if she's fine."

Laura waved a hand between them.

"Which way do you want to do it?" Laura emphasized.

"I've always let you pick."

"Well, you decide," she insisted. "But make it so you can do us both at the same time."

"Alright," Kent said, "Then just stand side by side and -- sort of -- lean over the desk."

Bailey took a deep breath and turned her back to him, leaning her body over about forty-five degrees and putting her hands on the desk. Laura took a place just to her right, so her khakis rubbed up against Bailey's jeans.