Two Hundred Dollars More Ch. 02

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Day 2

Kent had put on a fresh pair of boxer shorts to cut down on the dripping, and knelt on his bed between the half naked bodies of his two friends. Bailey, freshly showered and therefore free of semen in her hair, kept her upper body covered in a towel which she had lifted far enough to expose her narrow cheeks. Laura, of the more ample rear end, had never removed her top in the first place. Both girls lay on their stomachs, exposing their spanking-reddened asses to him so he could gently rub them.

Bailey turned to look at Laura through calm, half lidded eyes, “This will set you straight for a while?”

Laura didn’t even open her eyes, but let out a soft moan as Kent’s thumb dug deeply into the muscles of her cheek, “Yes. I’m good.”

“You’re incredibly red,” Kent said, “That’s what you are.”

Laura moaned again, “If I… y’know, do it myself-“

“Do what yourself?” Bailey prodded, her voice insistent.

Laura inhaled sharply and looked at the wall.

“Use your big girl words,” Bailey chided.

“Even if I masturbate,” Laura emphasized. “Or make myself come-“

“Because there’s a difference,” Bailey turned to look at Kent, adding sotto voce, “it’s only masturbation if you use your hands. Not if you hump the arm of a chair.”

Laura put her face down into the mattress in embarrassment, recognizing this little lecture as a speech she had given to Bailey only a few weeks ago.

“You were saying, Laur?” Kent said, squeezing both her cheeks.

“Yes,” she hissed. “Even if I make myself come, my bum’s so sore it won’t bother me.”

Bailey shook her head and looked up at the ceiling, “Christ, Laura.”

“Hey!” Laura protested. “No blaspheming, remember?”

Bailey looked at Laura, so aghast that Kent could tell she hadn’t cursed on purpose.

“We’re still doing that?” Bailey protested.

“Never took the rules away, Bai,” Kent taunted. “You each owe an extra spanking.”

“Each?” Laura turned in confusion

“You just said ‘bum’,” Kent pointed out.

“Ugh,” Bailey groaned. “My ass is soooo done.”

“Crap,” Laura added, looking down over her own back at the redness there. Then she shrugged and lifted her hips up, “Mine, too, but… well, fair’s fair.”

“Hm,” Kent said. “What if I let you wait for next time?”

“Wait?” Laura asked.

“Yeah,” Kent said. “Neither of you wants a spanking now, right?”

They both nodded urgently.

“But, putting it off means it gains interest,” Kent explained. “Right now, it’s a bare-assed spanking, since that’s how you’re dressed now. Tomorrow, it becomes a naked spanking. The next day, a bare-assed paddling. And the day after, a naked paddling.”

Laura inhaled softly, then looked over at Bailey.

“He’s a loan shark,” Bailey’s eyebrows arched up a moment. “You want to give it up now, or…”

Laura squeezed her lips shut for a moment, looking at Bailey, then her own cheeks, then up at Kent.

“It’ll be at least a couple days before I can take more spankings,” Laura said, “or even need anymore.”

“More interest, then,” Bailey shrugged as Kent drew gentle circles on their cheeks.

Laura shivered at his touch, lowering her hips back to the bed, “I — I can’t take anymore today.”

Bailey nodded in agreement.

“Thanks, Kent,” Laura said. “For letting us wait.”

“Up to you,” Kent replied. “In three days, it’s a paddling, and you’re both completely naked.”

He returned to his quiet massage of their sore flesh.


“Did I mention how brilliant that was?” Bailey asked the next evening as they ate dinner.

“Which?” Kent wondered.

“The interest thing,” she explained. “My butt’s still too sore today, so it’s going to be a while before she comes back.”

“Uh-huh,” Kent murmured distantly.

“You’re calculating even more ways to charge us interest in your head, aren’t you?”


A short pause, after which Kent shook his head clear, and took a breath to speak.

“It works, though, doesn’t it?” he asked. “Really works.”

Bailey inhaled, “Yeah.”


“I don’t know,” Bailey said. “There’s just something about… her. Being there. I like…”

Bailey trailed off and Kent knew enough not to interrupt.

“I like the look in your eye,” she said. “When you’re spanking us. And when I see you doing it to Laura, I can see it way better than when you’re doing it to me.”

Bailey shivered.

“We could still use a mirror,” Kent pointed out.

“Yeah,” Bailey tilted her head thoughtfully, “but the mirror’s not the same. I don’t know why.”

“You liked telling me when to spank Laura,” Kent pointed out, hoping this would help Bailey understand herself.

Bailey, unbelievably, blushed at his memory, “Yeah. C’mon.”


“Bedroom,” she rolled her eyes. “I’m wet now.”

Bailey pulled him along to her room, probably chosen for its proximity. Kent, who always carried a condom around these days, slipped eryaman otele gelen escort into the room after her.

“Good to go?” he asked, pushing his body against hers so they could kiss.

He felt such a relief every time their lips met, knowing how long a path they’d walked to reach that first, workable kiss. For the entire time Bailey had owed him money, through all the spankings and grinding and hand jobs, every attempt at a kiss had failed miserably. Only when the debt had finally expired, and Bailey’s self-accusation of prostitution had evaporated, could they actually kiss and have sex.

“Aren’t you?” she prodded when they came up for air. “After talking like that?”

Kent nodded and, kissing again, they started pulling each others’ clothes off. What a joy he felt when he could remove her shirt without hitting that weird barrier she’d had about her breasts. The jeans, tight as always, took a moment, but he got them off too. Then, kneeling, he pulled her panties down and gently kissed her vulva, smelling the powerful, natural perfumes leaking out of her.

Kent stood up again and they kissed, and separated.

“Can you, um?” Bailey stammered and kissed him again.

“Um?” he murmured around her lips.

“From behind?” she asked. “We haven’t done that yet.”

“If you’re wet enough, I’m sure it’ll-“

“I’m wet enough,” Bailey promised, desperately meeting his eyes.


Bailey turned around and braced her hands on her bed, whispering, “Gently.”

Kent tore open the condom wrapper, squeezed the air out of the tip and rolled it down the entire length of his erection. He bent his knees a little to get a good angle and put his tip between her lips, against her opening.



With a gentle push, he slid inside her.

She wasn’t lying. That was wet and easy.

He slid all the way in, his pelvis bumping into her still red cheeks. Kent gripped Bailey’s hips and started slowly pumping in and out.

“Am I still red?” she breathed at him.

I know what she wants to hear.

“You ass is soooo red,” he whispered back to her. “Such a bad girl.”

“Mm,” Bailey murmured back and he felt her hand moving under her body to touch her clitoris.

They’d had a short discussion about this, whether Kent needed to play with her clit while he penetrated her, but every angle from which he tried this caused his erection to poke in the wrong direction. In the end, Bailey had decided that she just needed him inside her while she took care of it.

“Kent,” she breathed.


“Try just one.”

Kent gulped. “Just one what?”

“One spanking,” she whispered back.

“Are you sure?” Kent asked. “It might make make your insides, um…”

“Gently, then.”

This explains the new position.

At first, Kent had thought Bailey had simply wanted show off her red flesh, testimony to how she’d help Laura take her punishment.

Kent gasped for air, “I’ll try not to come right away.”

Already though, just with the offer from Bailey, he felt the head of his penis swelling. He knew he didn’t have much of a chance of holding out.

“S’okay,” Bailey muttered, and her hand sped up its masturbatory circles.

Feeling her vaginal muscles already tensing around him, Kent strove to hold out. With his left hand holding her hip in place, he reared back with his right and laid a light slap to the outside of her cheek.

If I don’t go too hard, maybe I can hold off better.

Bailey winced, “Yeah. It’s okay. A little harder… harder…”

Kent slapped her again.

“Ugh!” she squeaked and her body seized up.

“Huh?” Kent grimaced, hearing this unusual grunt of pain.

“Other way,” Bailey shook her head.

She slid her body forward with a little twist, a motion Kent interpreted as her desire to get his erection out of her. He lowered his hips and carefully slipped out of her vagina. In a moment, Bailey had turned around to sit on the bed and spread her legs in his direction.

“This way,” she clarified, holding her arms out in invitation, as if her splayed legs hadn’t made her desire clear.

Slowly, he once more penetrated her, feeling a lot more resistance this time. A small wince from Bailey told him she felt it, too. Bailey inhaled and exhaled carefully, her eyes unfocused, blearily aiming her gaze in the vague direction of Kent’s stomach. After a few deep breaths, she started squirming around in small circles.

“There,” she breathed in relief as her body relaxed, “it’s okay, now.”

“Made you too tense?” Kent confirmed.

Bailey nodded.

“How’s it now?”

“Softening up,” she whispered. “Just need to relax.”

With his feet firmly planted on the floor, he had solid leverage, and the snugness of the condom left his erection reliably stiff. Kent could hold out as long as she needed to get used to the feeling of the hardened rod she then worked around her insides.

Biting her lower lip as she sincan escort twisted around, a smile slowly came to Bailey’s lips.

“There,” she sighed in true contentment, “there. Hoo, that’s hard.”


Recovering, Bailey’s hands move down her body, her left spreading her lips while the middle finger of her right hand moved smoothly over her clitoris.

“Oh, yeah,” she whispered, her muscles clenching around his erection once more.

Kent worried this might cause her problems, but it seemed this sort of muscle tension worked better than the kind his spanking had elicited. With a shrug, he started slow thrusts, working the angles until he got the appreciative moans that told him he’d found the right spot.

Bailey twisted her hips, sideways and downward, sinking him completely into her as she jabbed her clit one last time.

“Yeah!” she grunted as her face contorted and her body cringed, her vaginal muscles gripping him in spasms.

With one eye closed, she winced, her body holding Kent’s erection tightly inside her. His erection throbbed, wanting release, but Bailey had grown so tight inside he couldn’t move, never mind ejaculate.

I didn’t know this was a thing, he realized in horror. I can’t even come — can’t even pull out.

“Don’t move,” Bailey begged.

“Can’t,” Kent breathed his admission.

The next thirty seconds felt like an hour until Bailey relaxed again, allowing him some movement.

“Alright,” she sighed. “Alright. You can, um…”


“Fuck me,” she rolled eyes. “Fuck me some more.”

Kent pulled out, very slowly, and pushed back in. Bailey inhaled in startlement, but caught herself and kept her body from seizing up too much. A look of worry creased her brow.

“You okay?” Kent asked, already starting to ease out of her.

“Yeah,” she looked around nervously, pulling him back in with her hands. “Just come quick. I don’t know how much I can take.”

Kent nodded, wondering what strange brew of dedication, pain and pleasure had worked out to that answer. He eased outwards until the swollen head of his erection met the tight ring of her entrance, realizing quickly that he shouldn’t try to force his way any farther in that direction.

And what if she says it’s too much and I need to get out now? Kent wondered.

Fortunately, Bailey wanted him to finish inside her. Kent hoped, once they both relaxed a bit, he’d find a way to slide out without hurting her and without losing his protection.

He exhaled softly as he pushed back into her, eliciting a soft moan.

“Faster,” she said, her teeth tight together.

Keeping his movements short, Kent made small, quick thrusting motions in the limited space, backing up into the ring of her entrance and pushing forward until he met too much resistance. Bailey moaned, her eyes widening as his tip swelled inside her.

At least I’m going to come pretty qui-

With a violent and involuntary surge, his penis spasmed and spewed forth its first volley. Bailey let out a squeaking grunt of dismay at the sudden thrust of his hips into her body. Kent felt his eyes cross as his jerking erection fought for space inside her body.

Eventually, the surges calmed and both of them took deep breaths. Kent began to pull out, but couldn’t get past her entrance, still tense against the back of the head of his cock. For safety, he got a hold of the base of the condom. Whatever happened, he remained determined not to lose that inside her.

“Just wait,” Bailey breathed, motionless.

Kent nodded, delaying his withdrawal until some flaccidity to kick in.

“Spanking didn’t work?” he muttered, passing conversation in the meantime.

“No,” Bailey agreed, stifling a laugh. “Those weren’t even hard ones, either. Everything inside me just clamped up. Super uncomfortable.”

“You recovered, though,” he pointed out.


Kent found himself softer at that point, and slowly pulled down and out of Bailey. She still winced at the sudden emptiness, but didn’t cry out in pain.

“You’ve never gotten stuck inside me before,” she pointed out, looking down at his dwindling erection as he removed the condom.

“No,” Kent admitted. “That was weird.”

Wrapping the condom up in a couple of tissues, he tossed it in her wastebasket. Bailey laid down on the bed and Kent, perforce, laid beside her, one arm under her neck as she curled her hands against his chest.

“Too bad,” Bailey sighed. “Spankings don’t work, but sex still does.”

“We can both come,” Kent agreed.

“Mm-hm,” she breathed softly into his shoulder, her voice drifting off.


Kent thought that Bailey and Laura might take one extra day to pay off the extra spanking each owed him, just to lighten things up so he could surprise them with extra “interest” on their spanking debt. From Saturday, that should have put them eagerly in his bedroom on Wednesday. Instead, they’d waited until Friday to finally gölbaşı otele gelen escort drop by.

The two girls came straight to his room out of the deep, windy winter, their faces red from the blast of cold air they’d endured on their trek either all the way from campus or a shorter jaunt from Laura’s place.

“We’re a little late, aren’t we?” he asked, when they walked in, all smiles and coy downward looks.

“A little,” Laura giggled.

“An awkward situation, for certain,” Kent intoned, rising from his chair before his erection could pop up and make his situation awkward.

“It’s December,” Bailey sighed theatrically. “You know how hard it is, with the snow… and the exams coming up.”

“Right,” Kent twisted his lips, knowing the part he had to play. “I’m not really interested in your excuses.”

Laura coughed lightly and straightened at his tone, as if coming to attention. “So, um, what did we owe you?”

Kent had known it would come to this, so he’d already spent plenty of time considering his — and their — options. All the same, he wanted to draw out their tension a little, so he began pacing in the small space as if still in the throes of calculation.

“So,” he said, turning about suddenly, “I believe I was owed a bare-assed spanking from each of you. One for blaspheming, the other for poor word choices?”

Both Bailey and Laura nodded, trying to look humble while suppressing smirks.

“But that was Saturday,” Kent swivelled to face away, taking two steps toward the window before facing them again. “On Sunday, they became naked spankings. On Monday, bare-assed paddlings.”

He turned once more, speaking to the window, “And on Tuesday, bare-assed paddlings.”

Kent faced them again, motionless, “But now we’ve passed Wednesday, Thursday and we’re on Friday.”

“Sorry,” Laura averted her eyes downward. “We made you wait.”

“Very sorry,” Bailey didn’t try nearly as hard on her obsequiousness, failing her downcast look by simultaneously rolling her eyes.

“Now I suppose,” Kent drawled a little, walking up to Laura so he loomed over her, “I could just add more naked paddles.”

Laura gulped.

“One on Tuesday,” he said, “becomes two on Wednesday, becomes four on Thursday and eight today.”

Bailey’s eyes widened in what appeared to Kent as honest surprise. Eight strikes with that little silicone spatula would make it a night to remember, depending on whether or not he spread them around.

Unfortunately, Kent had realized early on in his weekly musings, eight of those across their rears would start the night off too hard.

Where would I go from there? he’d wondered. Nowhere at all.

The amount of pain caused by the red, Betty Crocker spatula would go straight to extra, especially on a bare ass. On top of that, he would have to make both girls take off all of their clothes as a first step, without all the preliminary stages of nudity. It hadn’t given Kent the proper sense of theatre.

No, we need to start off the night a little bit kinky, a little bit painful, just to get them in the right mood.

Kent had delivered the interest calculation that way, explaining each day of interest as a doubling, to impress upon them the enormity of the punishment debt. Kent figured that if he could raise the stakes that high in their minds, the next thing he told them to do would seem so much more generous.

“But I thought about that,” Kent turned back to the window pensively, “and it didn’t seem quite right.”

He felt more than heard the sighs of relief from the two girls, still in their winter jackets. Maybe the thought of stripping down to complete nudity while still chilled from the weather had frightened them too much. If so, he intended to use their relief.

“Instead,” Kent said. “Your completely naked paddling on Tuesday grew into a very special kind of spanking on Wednesday. Then two such spankings Thursday and -” he turned to look them in the eyes one by one -“four such spankings today.”

Both girls gulped and he could see that he had snared them both. Even Bailey had a look of wary trepidation in her eyes and Kent knew that both she and Laura would do whatever he told them next — within some sort of unspoken limit out on the fringes.

“These spankings are so special,” he added, a jerk of his chin toward the lower halves of their bodies, “that you only need to remove your pants.”

As if shocked with a cattle prod, both girls moved their hands to their belts.

“Mm,” he held up a cautioning hand and both froze. “Remove each others’ pants.”

Bailey twisted her lips then, the spell he’d cast partially broken at least for her, and turned to Laura, her open hands indicating that her friend should go first. Laura undid Bailey’s belt, reverse-feeding it through the buckle, and then unbuttoned her jeans. After a quick zip, she knelt and pushed Bailey’s jeans all the way down to the floor, revealing Kent’s favourite white panties, the ones with the transparent front.

After Bailey stepped out of her jeans, Laura stood and Bailey got to work on her friend’s much looser khakis. Underneath, a black thong threaded Laura’s cheeks.

“From now on,” Kent put in, watching Laura step out of her pants, “you should always take care of each others’ clothing, got it?”

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