Hurts so good, come on baby, make it hurt so good

Nick climbed on top of Gina and took a deep breath. He’d been doing a good job so far appealing to what Gina wanted; now he had to drive it home.

First, he started of gentle. He raised his hand and delivered a swift smack to her bottom.

“Hngg!” Gina’s body shook from the blow, and her ass rippled inside her tight skirt. But that wasn’t good enough.

“This skirt of yours is sexy as hell, you know that?” He leaned down to whisper into her ear. He caressed her butt through the thin material, getting a few good squeezes. “But you know… tight as it is, it’s really making it hard to see those cheeks clap properly.”

Shoot him. Fucking shoot him. Nick thought he’d die from shame saying something like that. But Gina seemed to love it; she squirmed with excitement beneath him.

“Maybe I should just… get rid of it.”

Gina had been saying how hot it was, the idea of him ripping off her clothes. Well, time to see just how true that was. He really hoped she wouldn’t get mad at him later.

It took some doing, but he managed to get his fingers hooked into the hem of her skirt. With a sharp tug, he tore it right down the middle.

RRRRRRIIIIIIIIPPPPP!

Nick was stunned at how easily the garment peeled off after the first tear, like unwrapping a Christmas Present. And he quite liked what Santa had brought him tonight. Gina’s fleshy white globes had a natural wobble to them, shaking slightly just from exposure to the air. He couldn’t help himself, seeing that spankable bubble butt, he just had to watch it in motion!

But before he brought down his hand, there was something else that caught his eye.

“No panties? You fucking slut.”

“Mmmmghmm… mhmhm…” Gina giggled, shaking her ass teasingly at him. He’d suspected, given the lack of panty lines beneath that tight skirt, but seeing was something else entirely.

“You’re such a fucking skank!” Nick shouted, slapping her right cheek hard enough to make her booty quake and her quim quiver. “Coming up to a man’s suite without panties on… wait, let me guess!”

He reached around and took two meaty handfuls of her breasts, squeezing them like stressballs. The pain made her squeal so loudly he broke character for a second.

“W-Wait, are you okay?” He gasped.

She shot him a dead-eyed glare over her shoulder and he shut right up.

Right. Right. Don’t break character. He cleared his throat to regain the mood.

“No bra, either, why am I not surprised? Did Sylvia even bother giving you any underwear at all when you got your new clothes?”

She shook her head, and for a second he wondered if she was just playing a long or if that was really the case.

The thought it might be true made the idea even hotter.

“No wonder you’re so fucking soaked then,” he laughed, jamming two fingers into her dripping pussy. She squeezed down tightly in response. “Walking around for days just begging for it. Well, if you’re not going to wear underwear like a decent human being, why bother wearing anything at all?”

He reached up to her collar and tried to rip off her shirt. It took a bit more doing as it wasn’t glued to her body the way her skirt was, but after a few strong pulls (which had the added benefit of **** her slightly, which she definitely enjoyed) he was able to get some tears in the fabric.

RIIP! RIP! RIIIIIIIP! He tore off strips of the black shirt, ruining it completely. Gina would be doing quite the walk of shame in the morning if she could still walk. But finally he had her, naked and helpless beneath him.

“Damn… that banging body really is the only thing you’re good for, isn’t it?” Now of course, that wasn’t true. As trashy as she was, Nick found Gina to be a lot of fun. But right now that part of his brain was taking a backseat. He was looking at her like the sextoy she wanted to be treated as, and he liked what he saw.

What caught his attention first were the tattoos. Not just the ones on her arm. The first time they’d had sex, Gina’s Good Girl transformation was still in place, so she’d lost all her original ink. But now it was back, and he had to admit- she had some damn sexy artwork.

The only one he could see from his current position was the pair of wings covering the entirety of her bare back. They weren’t faerie wings or angel wings, but something a lot more enticing. They looked like devil wings, inked on so beautifully it seemed they might spread out at any moment.

“Wlggn?” Gina humped back at Nick, snapping him out of his stupor. She looked back at him intently, waiting for him to get a move on.

He scowled and slapped her ass hard.

“Turn forward,” he growled. “I don’t need to see your face, you're just a set of holes right now.”

Nick couldn’t believe how much she squirted when he said that. Judging by the frenzy Holly was working herself into, his little painslut was almost at orgasm just from a few words.

“You’re fucking pathetic. Getting off to something like this,” he growled, spanking her again. “Don’t you have any fucking respect?! Any dignity?!” SMACK. SMACK. “You used to be such a nice girl! And now look at you! You’re just a fucking skank!” SMACK.

“Hnggh! Anngh!” A tremor shot through Gina’s body and she bucked her hips, desperately pushing her ass up against him. He felt her pussy juice seep into his pants as she began to grind against his erection, and he needed to put a stop to that right now. So he wound back his hand gave her the hardest spank he had yet.

SMACK!

“HNNNNGAAAHHHGN!” Gina arched her back, biting down hard on her gag. She started coughing, but he ignored it. She wouldn’t die from that toy.

“Stop.” His order came down like an anvil and Gina froze, save the occasional twitch.

“You’re ruining my pants you whore. What the hell are you trying to do? This isn’t about you getting off, it’s about me giving you the punishment you deserve. What sort of ungrateful sextoy focuses on her own pleasure instead of her master’s?”

He scooted back so she couldn’t grind on him anymore. She bucked her hips instinctively anyway, trying to lure his dick back in place. He gave her another warning smack.

“Until I feel this ass has suitably paid for everything it’s done, your dick privileges are revoked, understood?”

The only response he got was a small spurt of girlcum and a moan. Good enough.

“Let’s start your punishment then,” he said, palming her ass. He wanted to get a good feel of it before they really got going, and that creamy white skin turned red from ****. Damn… even now he could hardly fight the urge to start whaling on her. It just felt so good in his hands, like they just sank right in. His fingers practically disappeared into her squishy flesh.

Nope. He had to give her another test spank. And then another. Just a couple more. Then we can get started for real…

SLAP SLAP SLAP SLAP SLAP SLAP SLAP

Gina’s moans brought him out of his haze, and he realized her cheeks were already starting to pinken. Holy crap… I kind of just lost myself there.

“You bad girl,” he growled, spanking her a little harder. “Your ass is so fucking dirty, you know that? I can’t stop myself. It’s not my fault. No one could resist spanking a fucking ass like this! Shaking, taunting me… yes, that’s the perfect place to start!”

It took every bit of willpower he had, but he managed to remove his hands from that wonderfully juicy ass. He wound back his hand, holding it high over her booty like an executioner’s sword before a beheading.

“Apologize!” He shouted, bringing it down with everything he had. “Apologize for having an ass like this that tempts everyone around you!

SMAAAACK!

Her assflesh bent under his hand, and his slap left a nice red mark.

“HMG! SHRMMNGH!” She moaned, her lower half convulsing as she arched back against her bindings.

“Sorry, what was that? I didn’t hear you.” He spanked her again, even harder this time. Her moans shook the room, but he still didn’t hear a “sorry” from her.

“I said, apologize! Apologize for having this huge fucking bubble butt that makes everyone want to spank it!” He punctuated his order with another slap. “You know, those are good girls who you’re goading into giving you spankings, you slut! Nice girls who wouldn’t want anything to do with you! But no, you’ve gotta wear those tight fucking jeans and microskirts, just to taunt them! That’s why you go without panties, isn’t it? To make it feel that much better when they spank you?”

“Ungh!” She groaned at that last sentence, and Nick paused. It couldn’t be, right?

He quickly recovered and continued the spankings. “You’re such a bad girl, to make even straight women want a piece of this ass! Well, they’re not going to get any! I’ll just have to leave you tied up in here forever, just to keep them safe from your teasing ways!”

SMACK! SMACK! SMACK! He kept going until her cheeks started to turn rosy. He worried that he might be causing real damage, but she seemed to love everything he did.

“Well? Are you going to apologize for having such a slutty, tempting ass? Because we’ve got a long night ahead of us, and there’s a big list of things I need to punish you for!”

SMACK!

“SHRMNNMGRY!” He finally heard some real contrition in her muffled moan. Well, he had from the start, but now seemed like the best time to take it seriously.

“Now that’s what I like to hear. Let’s move on then.” Nick glanced down at her ass, taking note of the rosy hue of her cheeks. He saw that the right was a lot deeper than the left, probably because he’d only been using his right hand. Hm. He’d need to change that. He wanted her to get a nice even color, after all.

“Let’s move onto this outfit of yours. Or what’s left of it, anyway.”

Gina flinched, not expecting things to go in that direction.

“Oh yeah. You think I wouldn’t have any thoughts on that? You were such a good girl before, Gina. I liked those nice pretty dresses you wore. And you just went and got rid of them? Without even asking me? That’s rather naughty of you, don’t you think?”

“Mhng…” Gina mumbled, nodding slightly.

“And a naughty girl needs to be punished, right?”

Frankly, as cute as she was dressed nice, he found her a little bit sexier in her old style. There was a bit of a tradeoff, but that wasn’t the point.

The point was showing Gina that her body didn’t belong to her. That’s what she wanted… right?

“Well? Are you going to apologize for not asking permission to go back to your old look?” Nick asked, smacking her hard with his left hand.

“YSHHHN!” She grunted.

“No, I didn’t really feel that.” He gave her an even harder smack. “Swear to me that, when we’re done here, you’ll only wear what I tell you to wear.”

“AH SHWRR!” Gina managed to get out something that sounded like an affirmative, but it wasn’t good enough. So he spanked her again. “AHSSSSSSSSHHHHHEWWWRWR!”

“Nope, louder. Give me a little nod to go with it,” he ordered.

“SMACK!”

“AH! SHHWEER!” She nodded this time. At least it looked like a nod. It could have just been the way her back arched.

“Really? Even if I told you to wear nothing at all? Even if I tied a collar to you like Holly over there, and walked you around the hotel for everyone to see?”

She froze. For a second, he wondered if he’d gone too far.

That was dumb of him.

Gina began to shake, bucking her hips wildly. “AHYSH! AHSH! YSHHYSHS YSH!” She panted frantically, wiggling her ass to get him to spank her again.

“Good! Then we have a deal! Starting tomorrow, you’re going to pick out the nicest, sweetest dress you can find, and wear that!” Nick demanded. “No matter how much it clashes with your usual style! That’s the only way to prove your devotion to me, got it?!”

SMACK! SMACK! SMACK!

Her left cheek was about at parity with her right at this point. Time to switch it up.

Nick leaned down and whispered in her ear. “If you agree, then I promise I’ll spank you hard enough to make you cum.”

She didn’t say anything clear, she just moaned frantically into her ball gag. Judging by the way she was biting down, she was probably **** herself too hard to be coherent. But the frantic way she nodded her head up and down made it clear she had given in.

“Sounds like he have a deal then.” Nick wound back his hand and slapped her as hard as he ever had, making sure to hit both cheeks equally.

“HMGMNNGNGG! ANGGHGHH!” Gina’s moans deafened him. Her body started to convulse as she arched her back and strained against her bindings. For a second Nick wondered if she’d rip the bed apart. Her pussy juices sprayed out like dam had burst, shooting so far some actually landed on his pants again.

Oh yeah. These are definitely ruined.

But Holly was the real star of the show.

“Ahh! YES! FUCK! YES, FINALLY!” She knew she should keep her voice down. She had bitten the hem of her skirt for the sole purpose of keeping her voice down and not distracting the master while he played with his other sex toy.

But it felt so good. She’d only been in chastity for a few days. Not even long enough to constitute a full week in the real world. But for Holly it was a lifetime. She’d finally been able to play with her pussy again, going at it like an old friend she hadn’t seen in years. And now, finally…!

Wait. Wait, no. What’s happening!?

She was right there. Right on the edge. And yet it just didn’t come! Why?! Why wasn’t it coming?! She pawed frantically at her pussy, trying to get the edge off, trying to get that sweet release she’d been chasing this entire time, and yet…

Nothing. She just couldn’t come.

Holly raised her head in pathetic failure, staring up at the bed. She met Nick’s eyes, and suddenly she remembered.

His Favorite Unfavorite: Holly has been removed from the harem and deemed unsuitable to be bonded with the master. She has relinquished all claims to being in a relationship with him, but still desires him nonetheless. She will have an important part in the master’s life moving forward, not as a girl in his harem, but as a tool to enhance his sex life. From this moment on, Holly will be unable to achieve physical stimulation through contact, whether by her own hand or someone else’s. The only thing capable of arousing her is the sight of the master with another woman. The only time she will be able to achieve orgasm is when another woman is brought to orgasm by the master, and only upon receiving verbal permission from that woman.

Holly needed Gina’s permission to cum.

Permission Gina couldn’t give with that ball gag on.

“Is something wrong?” Nick asked coolly, and that’s when she realized that he knew. He’d known all this time. Everything he said about letting her finally orgasm, going until she satisfied herself, it had all been a lie. A trick to get her hopes up, when he never intended to let her cum at all.

She fell in love with him all over again.

Oh master! You’re perfect! Just perfect! Knowing that orgasms were off the table tonight, Holly redoubled her efforts on her pussy. She might not be able to cum, but she needed to make full use of this chance while she had it. Who knew when she’d get the opportunity to play with herself again?

Maybe never.

God that would be so hot.

“I love you!” She blurted out, startling Nick for a second. He quickly shook that thought free and turned his attention back to Gina.

“Hear that, slut? That’s how a sex toy properly expresses her gratitude. She knows she’s not going to be able to cum tonight, but she’s still telling me she loves me. And you, well… you’re only thinking about yourself. Maybe I should switch, hmm? Leave you locked up in the cage, and have Holly take your place up here?”

He wondered what she’d think of that. And judging by the way she trembled underneath him, he knew she was imagining it too.

But while the list of things he could punish Gina for was extensive, they needed to get a move on. His dick was getting impatient.

“Not tonight, slut,” he growled, spanking her again. “Tonight I need a hole I can actually take pleasure in. And as worthless as you are, at least your body’s a little better than hers. So tonight’s your lucky night!”

Before she could react he unzipped his pants and fished out his cock, and slammed it inside of her as hard as he could.

“HHHHHHHHHHHHNNNNNNNNNNNNNGGGAAAAAAAAGGHHHHNGG!” Her walls clenched down tighter than they ever did that first night together. That response helped Nick feel a little more certain about what he was about to do. Gina clearly wanted him to just hump away at her to get himself off; she got off on him fucking her as brutally as possible.

That was a relief. Because he was thrusting into her so hard he felt the bed shake, and if she wasn’t cumming her brains out then he’d start to feel like a ****.

“Ugh, tighten up you fucking skank!” He shouted, swatting her ass as he buried himself as deep inside her as he could go, bashing his head against her cervix and making her scream. He doubted that Gina could get any tighter, but she clearly responded to the thought that her pussy somehow wasn’t good enough for him.

“How many men have been inside of you, anyway?!” He growled, tearing into her like a wild beast. He mauled her ass, no longer just spanking it but squeezing it so tightly his nails dug into the enflamed flesh. “Ten? Twenty? A hundred?! Can you even remember any more, you fucking slut?!”

“NGH! NOAHHNG!” She moaned, shaking her head frantically. Nick saw tears in her eyes, but he couldn’t back down now. She wanted this. And deep down, he wanted this too.

“Well it stops now,” he hissed, backing out as far as he could without pulling out completely. “You’re MINE!” He slammed himself all the way to the hilt and she screamed, bending so far back he thought she’d break her spine. He felt her walls clench around him in orgasm, fighting every second to keep him inside as he pulled back for another go.

“MINE!”

WHAM!

“MINE!”

WHAM!

“MINE! MINE!”

WHAM! WHAM!

If not for the chains he would have fucked her right into the headboard. Hell, she’d probably be into that. She was so fucking twisted she might find brain damage sexy, who knew? But one thing was for sure, she was his.

She just needed to admit it.

“You understand?!” He shouted, squeezing her ass tight enough to make the flesh ooze through her fingers. “No other man is going to have you again! I’m not giving you away to anyone! You’re MINE! And if I have to keep you locked up in a cage right next to Holly, that’s what I’ll do! I already lost you once! I’m not losing you again!”

Wait… where did that come from?

Nick didn’t know why he said that, or what he should say next. So he just kept thrusting, reveling in the delicious warmth of her soaked insides. He humped away at her, tearing at her ass with his hands as she screamed and moaned and squeezed around him.

Then he had another idea. The way her tangled curls bounced in front of him was so tempting that he just had to reach out and-

“HYUNNNNGHGH! AAHHHHHHHHHHNGGG!” Gina came like crazy, squirting all over him. He couldn’t hold it in anymore; he’d been driven purely on instinct and lust, and it was all coming to a boil. But he remembered Sylvia’s warning this morning about morning sickness and pregnancy; he doubted Gina would be on any kind of birth control at all, given how little she cared about responsibility.

It took everything he had but he managed to pull himself out of her hungry hole, and sprayed his load across her back. Her devils wings were stained in white and some even got in her hair. Not that she’d care all that much.

“Hng… guagh…” The heat between them began to cool, and Gina stopped spasming. She was still struggling to breathe, but whatever **** effects the ball gag inflicted seemed to have worn off.

But he was still hard. Damn. Even after releasing a load like that, seeing her tied up in front of him hadn’t softened his dick in the slightest.

“Well? What do you think, Holly?” He asked, turning to his other little ****. She was still digging frantically into her pussy, her face flushed and her dilated eyes jonesing for more. He knew what her answer would be before he even asked.

“Has she earned her freedom yet?”

Holly practically tore her head off with how fiercely she shook it.

By the time Holly finally relented and let Gina go, Nick thought his dick was going to fall off. How many times had he cum on his little tied-up ****? Four? Five? It couldn’t have been more than that… could it?

He wasn’t sure. He could barely think straight with how worn out he was.

But somehow, he managed to trudge over to the cage and retrieve the key from Holly, making sure she was locked up tight in her chastity belt for the night. The blissful look on her face surprised him; she hadn’t been able to orgasm, but it appeared that, somehow, she’d been satisfied.

He wondered if she had reached the point where just getting to the edge of an orgasm was enough. That was a scary thought.

“Good night,” he whispered to his little caged pet as she nestled herself down into her mattress.

Nick returned to his bed, not risking a glance at the clock. Frankly he didn’t want to know how late into the night they’d been fucking. But he undid Gina’s bindings and took the ball gag out of her mouth, waiting to hear what she thought of his performance.

“Haagh… ang…” She had to work her jaw a little bit. He realized how sore it must be. Never mind her ass; she’d have trouble sitting down for a while. He doubted she’d be able to heal before their next night together!

Maybe she wanted that.

“How, um… so how was that?” Now that his libido had cooled, he didn’t feel as dominant or aggressive anymore. He was just concerned about whether or not Gina had gotten what she wanted.

She smiled up at him.

“Perfect…” She whispered, her voice strained. Maybe from the ****, or maybe from all the screaming. Either way, she was exhausted.

He crawled into bed beside her and pulled her into a hug.

“H-Hey, what-?!”

“I love you,” he whispered into her ear, feeling her stiffen up.

“Dude, you don’t have to-”

“I love you. You’re amazing. I would never, ever think you’re worthless. You’re perfect just the way you are, I love you.”

Nick had no idea where that aggressive, dominant side of him had come from. But he said everything he could think of to offset whatever ideas might have been planted into Gina’s head about his feelings for her in this session. She needed to know that whatever he said in the bedroom, that didn’t reflect how he really felt about her.

She mumbled something under her breath and he thought he saw her face heat up. But he was too tired to be sure. He drifted off to sleep with her soft body in his arms, hoping she didn’t take his repudiations to heart.