by Livia Grant
“Twenty! I’m sorry for being disrespectful, Professor Romeo.”
Sometime between ten and twenty, the sass had completely left Juliet’s voice, and she’d actually started to sound remorseful. Orlando grinned. Five more to go, then another ten with the ruler, and she should be more than ready for his cock. There was a glistening sheen of her juices already coating the tops of her thighs, just below her pussy.
For the last five, Orlando decided to switch things up a little. He wanted to leave her stinging and throbbing all over, and spanking her swollen, needy pussy would accomplish that and more.
He angled his hand, bringing his palm down on her pussy with a wet thwack. Juliet shrieked, much higher than before, and for the first time, he actually had to use his hand between her shoulder blades to keep her in position.
“Ow, fuck!”
“That’s not what you’re supposed to say, Miss Kaplan,” Orlando reminded her wickedly. He brought his hand down on her pussy again before she could protest.
“Shit! Twenty-one! I’m sorry for being disrespectful, Professor Romeo!”
Smart girl. She hadn’t tried to skip ahead to twenty-two, accepting the fact she’d be getting six swats to her pussy. It wouldn’t make Orlando go any easier on her, but he would have added additional punishment if she’d tried to count the one she’d missed.
Juliet
Fuck.
She was so hot and wet, and every slap of Orlando’s hand on her pussy got her a little closer to orgasm. Tears had gathered at the backs of her eyes, but none were falling yet. It hurt, but not enough to push her over the edge.
Now that she was expecting the sizzling snap of pain, immediately followed by a hot rush of arousal, she didn’t yelp again. She whimpered. Squirmed. Moaned. His fingers slapped her clit, making the tiny bud swell and throb even more.
“Twenty-five! I’m sorry for being disrespectful, Professor Romeo.”
She was so turned on, she didn’t even mind calling him that anymore, not the professor part, not even the ‘Romeo’ part. Who cared what his name was? She just wanted him to fuck her.
A rose, by any other name, blah blah blah, whatever, as long as it could dick her good.
The sudden cessation of painfully pleasurable torment was far worse than the spanking. Juliet groaned, panting and waiting for him to pick up the damn ruler. The feeling of satisfaction when he did was almost as good as actually being spanked. Her anticipation wound around her.
“Five with the ruler.” The hard wooden length tapped gently against her bottom, teasing her with the promise of pain. “Count them out the same way, starting from one.”
Before she could say ‘Yes, Sir,’ he drew the ruler back and brought it crashing down against her already stinging ass. Fire licked across her skin, and Juliet cried out, her pussy clenching in response to the lash of pain, even as worry rose she wouldn’t be able to bear it.
“One! I’m sorry for being disrespectful, Professor Romeo.”
Crap, that was totally going to leave a welt.
As was the one that landed right underneath it.
A little sob hitched Juliet’s voice as she counted that one as well. Fuck, that hurt. The third one landed right beneath that, just above her pussy lips and sit spot. Juliet stomped her feet as the fiery agony seared her.
“Three! I’m sorry for being disrespectful, Professor Romeo.”
Tears slid down her cheeks. The ruler stung far worse than his hand, covering more area, and with a far harsher bite than his palm.
The fourth blow was the worst—rather than laying it down horizontally beneath the others as she’d expected, it crossed the three diagonally, right over the welts he’d already give her. Juliet stomped her feet again, dancing with the pain as she wailed out the fourth count, her tears dripping onto the desk before her.
Why did that turn her on? She didn’t know, but her pussy was hotter and wetter than ever. When he landed the fifth swat of the ruler vertically over her swollen labia, the end of it snapping against her sensitive clit, she almost climaxed, even as she screamed from the pain.
Orlando
“Please, please, please,” Juliet chanted, her bottom waving up and down in the air as she danced, trying to soothe the punishment.
“Please what, Miss Kaplan?” Orlando asked, dropping the ruler and dipping his hand down to brush his fingers over her pussy. She shivered, making a whining noise, and pushing her ass back at him. His cock throbbed. Fuck, he wanted to be in her so damn bad.
The purplish welts stood out on her skin, imprints of where the ruler had landed, and her puffy pussy lips were slick with cream, despite the abuse he’d inflicted on them. He barely touched them, teasing her, wanting to hear her beg.
“Please, I need to come.” She went up on her tiptoes. With his hand between her shoulders, pinning her down to the desk, she couldn’t do much more. Her palms were flat on the desk on either side of her, letting her brace herself, but she couldn’t reach for him. “Please, Professor Romeo!”
Orlando chuckled. She really was desperate.
“I’d hate to be accused of harassment, Miss Kaplan,” he intoned, gently stroking her clit before pulling his finger away. “You’ll have to be more specific about what you’d like me to do.”
“Oh, just fuck me, damnit!” She squirmed, trying to reach his hand again with her eager pussy. “I want your cock, Professor Romeo!”
Far be it from him to ask twice.
Opening the front of his pants with one hand, he moved behind her as his cock sprang out, eager and ready. Precum already seeping from the purplish head, the length was a darker color than normal from denying himself satisfaction. He quickly pulled a condom out of his pocket and rolled it on, giving Juliet a quick, hard smack on her ass to keep her primed and ready.
Fully gloved, he lined his cock up with Juliet’s pussy and shoved in deep and hard. She squealed, bucking as half his cock sank into her wet heat, forcibly stretching her muscles. Leaning forward, Orlando thrust again, shoving his full length into the silken tunnel, groaning with pleasure as he finally got inside her. His hands slid under her body to her breasts, releasing the knot between them with quick tugs, filling his hands with her bounty.
Her pussy clenched around him as he gently squeezed. He didn’t want to open any of the cuts he made, so he concentrated on her nipples, pinching and rolling the sensitive buds as he drew his cock back and thrust in again. Tugging her nipples, he used them to pull her back against him, feeling the heat of her punished ass against his groin, her pussy clenching around him as he rode her.
This is wrong. This shouldn’t feel so good.
But it did. It felt more than good, it felt right. He was so fucked… but there was no way in hell he could stop fucking her now. And damn the consequences.
Juliet
Fuck, fuck, fuck.
That felt so damn good.
Orlando’s cock filled her, the very tip nudging against her cervix in a way that teetered on the edge between pain and pleasure. Juliet moaned as he moved, his hard muscles slapping against her ass, reigniting the pain from the welts, even as his cock filled her with pleasure. Trapped between him and the desk, there was nowhere to go, nothing to do but take his cock and ride the waves of alternating agony and ecstasy.
Her nipples pulsed between his fingers, the tight pinch adding to the tumult of sensations, her breasts extra sensitive after their first scene. Every slap of his body against her ass left her whimpering, though the tears had ceased as soon as he’d shoved his cock in her.
Every stroke of his dick made her knees quiver as her hands braced against the force of his thrusts. He was fucking her as if there was no tomorrow—and there wasn’t, was there? He was her stepbrother.
It was the utterly filthy thought, the shameful acknowledgment she’d begged her stepbrother to fuck her that tipped Juliet over the edge. She screamed out her orgasm, her pussy clamping down on his cock, and Orlando groaned. Straightening, his hands slid down her si
des until they reached her hips, gripping hard.
She cried out again as he fucked her even harder, riding her through the initial waves of pleasure, sending her soaring even higher as another orgasm wracked her senses.
“Oh, fuck, oh, fuck, Orlando!” She screamed his name, sobbing again as the intense sensations overwhelmed her, the mix of hellish torment and erotic nirvana sending her flying.
When she said his name, she heard his own shout, his hands tightening on her hips, cock pulsing inside her, filling the condom with his cum… making her scream out again as a third orgasm drowned her senses.
Chapter 9
Orlando
This time, he got to cuddle with Juliet a lot longer than after the first scene. She was flying high—maybe not quite in subspace, but pretty close—and too muzzy to protest when he wrapped her up and cuddled her, still dressed in the schoolgirl outfit. He’d loosely wrapped the shirt around her breasts, but not nearly as tightly as before.
Not that he was trying to preserve her modesty, but he was hoping being a little more covered might make her feel less vulnerable about snuggling in his arms. Either it worked, or the impact of two scenes in a row was taking her longer to recover. She stayed cradled against him without protest, and when she did finally sit up, it wasn’t with a jerk of realization. This time, she pushed herself up almost reluctantly.
Or maybe he was projecting because he was reluctant to let go of her.
The night was flying by faster than he’d thought it would, and they only had one roll left.
Shifting nervously on his lap, Juliet tied the shirt between her breasts, still keeping it loose, before finally meeting his eyes. There was a seriousness in her gaze that hadn’t been there before. Some of the heat had been banked, but anticipation remained.
“So…”
Orlando gave her a lopsided smile.
“Ready for round three?” he asked, curving his hand over her lower back. Juliet nodded and got to her feet.
Settling his hand on the small of her back, Orlando silently escorted her to the main room. They passed a small crowd around one of the other scenes but were too far back to see what was going on. Several people in the bar caught his eye and gave him a thumbs up—likely voyeurs from one or both of his and Juliet’s previous scenes.
Normally, he would have enjoyed the silent accolades, but right now, his gut was too twisted. He’d come to Roulette anticipating a hot night of pushing a submissive’s boundaries—and there wasn’t much he wasn’t willing to try at least once, so he hadn’t expected any of his own boundaries to be pushed. He especially hadn’t expected his emotional boundaries to be in danger.
As always, everything having to do with Juliet was a little more fraught.
Juliet
Walking back up to the roulette wheel felt a bit like walking to her doom. What would she and Orlando have to do this time? How much would it change them? Things between them had already changed. She felt it and knew he did as well, even if neither of them was willing to verbally acknowledge it.
How were they supposed to go back to real life after this?
That’s a problem for the future Juliet. Focus, sister. Present Juliet is about to have another round of filthy, hot sex with her stepbrother. Might as well enjoy it and let future Juliet figure out the rest.
Sound advice from the crazy voice in her head, though she was pretty sure Future Juliet was going to curse the hell out of Past Juliet. She could only live for Present Juliet right now, and her wild side wasn’t wrong. Might as well enjoy the chance while it lasted, since—a quick glance at the clock confirmed—it was only going to last another hour.
This time, when the wheel spun around and the ball landed, the anticipation was tinged with a bit of regret it would be the last time.
“Humiliation!” Mistress Madison said gleefully, and Juliet couldn’t help but feel a little disappointed. She’d hoped for something… more. Something edgier. Something that would hurt more.
Turning back to Orlando, she was a little surprised by the thoughtful look on his face. He didn’t seem disappointed, if anything, the expression on his face was calculating. Her stomach did a little swooping thing, but she raised her eyebrows at him questioningly.
They’d known each other long enough he should know she didn’t embarrass easily. She didn’t even know if humiliation was a kink or not because she’d never experienced it. Call her bitch, slut, whore, none of that phased her, but it didn’t turn her on, either. ‘Neutral’ would be the best way to describe her feelings. Insults just made her laugh. Yeah, she might have a few areas of her body she wished were better, but she loved herself and knew—as a whole—she was a damn fine catch.
“Get undressed. Completely.” The order almost made her roll her eyes again. They were in Black Light. The theater wasn’t even close to full, although several people had come to see what the wheel would land on, just as they had before, it was nothing compared to how packed the theater had originally been. She’d already paraded around the club completely naked tonight. Hopefully, he didn’t think a little public stripping was going to humiliate her. She was a freaking exhibitionist.
With a glance at Mistress Madison, who seemed more intrigued than anything, Juliet inwardly sighed and started to undress.
To her surprise, Orlando didn’t stick around to watch, although some of their audience had settled into seats to see what was going to happen. Orlando hopped off the stage and went over to the DM hovering just inside the theater door. A quick conversation and the DM trotted off.
Turning around, Orlando met her gaze, and a slow smile spread across his lips. Flip. There went her stomach again. He was up to something, but Juliet couldn’t imagine what. She also worried whatever it was, it couldn’t match the anticipation building inside of her. Wouldn’t it be awful if their third roll was a total letdown? Maybe they should have just ended it already.
“Turn around and bend over,” Orlando ordered her as he walked up the stairs onto the stage. “I want your hands on your cheeks, spreading them open. Show the nice audience your delicious ass.”
Oooh, anal sex was in her future. Big surprise. Still, the fact it would be with her stepbrother… that added something. Maybe her third roll had been a bit of a letdown, but at least that part would be fun.
Bending over, Juliet spread her cheeks and held the position. The braids in her hair still hung down on either side of her head, making her feel even naughtier for some reason. Her fingers dug into the welts the ruler had left behind in a pleasurably painful way, which wasn’t exactly a hardship. So, she held.
And held.
And held.
To her surprise, her cheeks—the ones on her face—started feeling warm after a few minutes of showing off her asshole to the people in the audience. It was the length of time that was starting to make her feel a little off-kilter. There was literally nothing happening other than people staring at her ass. It turned her on to know everyone was staring at her pussy and asshole, but somehow, despite that, it was starting to affect her.
Someone in the audience giggled, and Juliet’s blush heated. Thank God her skin wouldn’t show it too much. Yeah, okay, this was kind of embarrassing.
She turned her head to look at Orlando, and he stared passively down at her. Juliet dropped her gaze again, ignoring the growing whispers in the audience. Well, trying to do her best to ignore them.
The DM finally came back through the door and hopped up onto the stage, handing something to Orlando, who murmured his thanks before turning back to Juliet. She saw a small flash of silver in his hands before he moved to her side, obviously positioning himself so he wouldn’t block anyone’s view of her ass.
“Stay very still, Juliet,” he said, only a hint of amusement in his voice.
Juliet closed her eyes and took a deep breath. A moment later, she jumped a little when his finger, covered in cool, slick lubricant, touched her ass and began to push in. She bit back a moan as he frigged her asshole, probing
and slicking the entrance. Her fingers dug into her cheeks more.
It was a totally different sensation from having her pussy fingered, but just as enjoyable. The ring of nerves around her entrance was exquisitely sensitive, sending tingling sensations through her, and the stretch to accommodate the girth of his finger was only a little uncomfortable.
When his finger retreated and was replaced by something much harder and colder, the discomfort grew. The muscle around her entrance strained, burning with the stretch before the plug popped inside. It was metal, that much she was sure of from its heavy weight and complete lack of give. Her muscles rippled around it, clenching and pushing, but it was securely lodged. Juliet panted from the sensation of being filled, even if it wasn’t quite enough.
“Alright, down on your hands and knees, Juliet. You’re going to crawl for me.”
Heat, need, and, yes, a tiny flicker of embarrassment licked through her.
Something tugged on the plug when she got down on all fours, startling her, and she glanced over her shoulder. If there’d still been a bit of blush in her cheeks, it hit full bloom when she realized it was no regular butt plug. Nope. This plug had a metal chain coming from it, which dangled down from Orlando’s hand, connecting them.
He had her plug on a leash.
Juliet’s pussy clenched even as the surprising feeling of humiliation slid through her.
Twitching the leash, Orlando knocked the chain against her ass, his eyes glinting with amusement.
“Get going, Juliet. We’re going back to the play area.”
Which meant crawling down from the stage, out of the theater, through the side of the bar, and past the curtain, where people were actually playing. Orlando intended as many people as possible saw her with a leash coming out of her ass.