Saddling the Sadist

John didn’t feel any different as he popped the pill. That was to be expected, though. “How long will this take to kick in?” he asked the blonde in his lap. As unlikely as it was, the blonde in question was Vanessa Hawthorne.

“Depends,” Vanessa replied shortly and with a slight sulk to her voice as she watched the rest of the room exhaust her supply of the mysterious pills. Sharing with the entire posse had clearly not been her intention, but as far as John was concerned, she could suck it up. It was going to be a long road for her to truly make amends for all the shit she’d put him through. “You owe me, Newman,” she scowled. ****, John’s magical charm, and the promise of sex had done a lot to soften the girl, but she was still twisted inside.

“Hey,” John said forcefully and cupped her chin in his hand to turn her head towards him. “Whatever you think I owe you is going to be repaid in this bedroom tonight.”

Vanessa opened her mouth to protest but all that came out was a wavering moan as John’s hands went to work on her body. “I think,” John began as he gave one of her hard nipples a twist. “That it’s time,” he continued as he sunk two didgits of his other hand into her velvety cunt. “You repent,” the blonde tensed as John’s teeth scraped across her earlobe. “For all the shit you’ve dragged me through,” he finished as his mouth trailed down to her shoulder. He bit down sharply, causing Vanessa to release a sharp yelp of pain, though one not entirely absent of pleasure, either.

“What the fu-aaahck!” she cried as John stood up and flipped her onto the edge of the bed so that her juicy ass was presented to the room. He thrust his dick forward and found a home in the cleft of her cheeks, causing Vanessa involuntary shiver in excitement. She was no stranger to anal, that much was clear. John grinned, and then shook his head. Her enjoyment was far from his highest priority right now.

Captivated by the touch and sight of her plump ass, John pulled a hand away from her breast to give it a light smack. Then he hit it harder, causing a sharp crack to resound through the room. Her porcelain skin bloomed a bright red where he hit her and she’d actually lost a point of health from the hit.

“Oww, fuck, Newman,” Vanessa turned her head and snarled at him; that all-too-familiar side of her personality reared its ugly head again. “Quit with the shit and just fuck me already.”

John answered with another, harder, slap to the same cheek before pressing her roughly into the bed. “Beg for it,” he shot back smugly, without a trace of sympathy for the sadistic bitch as she squirmed helplessly under him. She let out a whimper of pain in response. Vanessa was probably so used to dealing pain she rarely experienced it herself.

“What was that?” John leaned his head forwards.

“...P-please,” she muttered, still glaring at him.

Another slap echoed across the room. “Louder.”

“Please!” The blonde’s eyes were watering.

“What exactly do you want me to do?” John leered as he slapped her again. Her ass was a flaming red.

“Oh, god, who the fuck are you, John Newman?” Vanessa’s defiant tone had been quelled to whimpering submission. “I can’t believe I’m here… with you… oh go-ahh-d!” she moaned aloud as his fingers danced across her sore rump. “I want you to fuck my ass…” the cheerleader cried. “Like Frank never could… like nobody on that shitty football team could.”

John let out an amused grunt before digging one hand firmly into her ass while lining up his cock with the other. ‘How many exactly have come through her back door?’ he wondered briefly before discarding the thought. It didn’t matter, he’d outdo them all tonight. Vanessa let out another whimper as he pushed his head against her anus. The tongue-fucking she’d received and his own finger had done a bit to prepare her, but his girth was far bigger than what her butt was accustomed to and they weren’t using lube.

It took several forceful thrusts to bottom out inside her, the effort leaving them both momentarily breathless. John recovered first, and - not caring whether Vanessa was ready or not - began to jerk his hips roughly. Her fingers curled tightly into the bed sheets as she released a strangled wail which teetered into blissful moans as John’s abilities began to work their magic. With each thrust her inner walls constricted around his cock, drawing out a strangled but intense kind of pleasure. John couldn’t decide whether it was better or worse than wet pussy, but he was certainly enjoying it. The rawness, the dirtiness, the roughness of it… he wasn’t just fucking Vanessa-fucking-Hawthorne in the ass, he was dominating her. She was his bitch now. John was euphoric.

Vanessa moaned receptively as he laid down on top of her, nibbling on the flesh along her shoulders, marking her as his. She was coming to accept her role as the submissive now, melting into his rough play and doing her best to match the rhythm of his thrusts. “Oh, John,” she whimpered, her voice slightly muffled by the sheets. “U-use your hands again… please. You’re so goda-ah-mn, fuck!”

John scowled. “Do you really think you have the right to ask anything of me?” he growled into her ear. He felt a heat bubbling in the pit of his stomach. Not the kind born of sensuous passion but a vile hatred. One of her arms shakily began to stray southward. John slapped it away. “You don’t get to touch yourself, either. Not unless I say so. You are one of the most horrendous sacks of filth to have unfortunately graced my life. I despise you, Vanessa,” John laughed cruelly, enjoying that there was an audience to watch the girl’s humiliation. “I used to fantasise about this, you know? Do you know how it always ended? Guess.”

“I… ah!” Vanessa writhed underneath him. “I can’t… I don’t know.”

John put his lips to the girl’s ear. Vanessa shuddered as she felt his warm breath right over the canal. “I would **** you.”

Her body stiffened at his words and the heat in her face seemed to dissipate a little. John couldn’t help but laugh at the discomfort in her eyes as her head grappled with the arousal of her circumstances and the **** of his words.

“You’re lucky then, I suppose, I’ve developed a strong distaste for killing,” John continued as a half-hearted attempt to ease her mind. “But I think I know of a far better way to punish you instead.” He didn’t bother asking her to guess this time. “I’m going to give you the greatest fuck of your life. I’m going to do you so well you can’t think about anything else. I’m going to ruin you. There will be no substitute for me when I’m done with you… but I will never touch you again. And it’ll drive you mad, pining for something you can never feel again, knowing it was your own cruelty that buried the possibility of ever experiencing something like this again.”

The girl’s body shook underneath him. He slowed his thrusting slightly, running his hands along her quivering form. She felt so small now. He could break her if he wanted to. It was amazing that not long ago she could have had him under her shoe. Briefly John wondered whether he was going too far. ‘No,’ he shook his head of the doubt as vindication and retribution won over. ‘If anything, I’m being magnanimous.’

“Now, what are you?” he asked her after a moment’s pause.

“...I-I’m sorry!” she cried. “P-please forgive me.”

Her voice was too riddled with fear and lust to tell whether it came from a genuine place or not. It was not the answer John was seeking, in any case. “No, we’re past that point,” John shook his head and slapped her violently on the ass once again. “What are you?”

There was the slight sound of tearing fabric as Vanessa’s clenched fists tore the bedsheets. John doubted the girl was in control of her own body, she was just trying her best to endure the violent fucking. “I’m a-ah… a…”

“You’re a sack of filth,” John said helpfully. “Repeat it.”

There was a moment’s pause. “I’m a sack of filth,” she mumbled, either unable or too afraid to face him.

“That’s right,” John agreed, quickening the pace of his thrusts again. He could feel himself nearing his peak.

Vanessa could sense it too. “P-please, John, cum in my ass. I need your cum… because I’m filthy.”

“I’m going to cum in your ass, alright,” John sneered. “And then I’ll cum in your mouth. And your cunt. I’ll cum where I please, and right now that means all over you. You’d like that, wouldn’t you?”

“Yes,” she replied with another whimper.

“Good girl,” John laughed. “You can touch yourself now.”

Vanessa’s body lurched in response as one hand immediately flew to her crotch. John laughed as he watched her fervently masturbating, betraying just how high she was getting off the submission. It didn’t take her long to climax. Her muscles tensed and her teeth bit into a pillow as the orgasm crashed over her. The muscles in her ass were no exception. John let out a gasp as her anus clenched down on his shaft, signalling to his heavy balls it was time to release the load he’d been steadily building over the course of his hate-fucking.

“It’s so thiiick,” Vanessa cooed as she felt him spurt up her back door.

Once the fog of the climax lifted, John slowly pulled out. His cock was covered in thick globules of his own cum, and more was dribbling out of Vanessa’s raw and gaping anus.

“Clean me up,” he ordered her, flipping the cheerleader on her back and thrusting his cum-soaked cock against her lips. His cum smeared over her flushed face as he did, but she eagerly obliged, opening her mouth and giving his sensitive head an obedient lick. John grinned at her submissiveness. His hands clenched into her now dishevelled blonde hair and thrust his shaft into her mouth. Vanessa gagged, and John felt spittle trickle out from between her lips and his cock, soaking his balls. He pulled back a little, allowing her a brief respite to recover and prepare herself. Soon he felt her tongue caressing his shaft and the back of her throat as she **** herself to swallow more of his cock. She moaned as she took him in her mouth. She was well and truly broken now.