Seduced by a Sadist on Valentine's Day

“What are you still doing here?”

Eli turned away from his computer to see Cassia, a coworker, standing at the edge of his cubicle. Her hair was pinned up in a slightly messy bun, her blouse had come untucked on one side, and it looked like she’d unbuttoned it right down to her cleavage, all of which led Eli to believe that Cassia expected to be the only one in the office at 6:30 p.m. on Valentine’s Day.

“Working,” Eli replied. “Just like you, I suspect.”

Cassia put a hand on her hip and said, “But you never stay late. You’re almost never here on time, either. You’re not a hard worker, Eli. So again, what are you still doing here?”

Eli was taken aback. “Whoa, whoa, that’s not fair. I’m a hard worker.”

“It’s perfectly fair because it’s honest, Eli,” Cassia said. “I don’t care that you’re not a hard worker. In fact, I like it. It means there’s one less person for me to beat out for a promotion. So, what are you still doing at work?”

Eli stared silently for a few seconds in the hopes that Cassia would just go away, but it seemed that she had no intention of doing so. He couldn’t figure out why she wouldn’t walk away, but she was unquestionably his oddest coworker, so nothing she did was a surprise. “Okay, fine, I don’t have a date tonight and going home and sitting alone in my apartment seemed pathetic, so I figured I’d stay and get some work done.”

“You didn’t have a date last year, either,” Cassia noted.

“How do you remember that?” he asked.

She smiled. “I have a good memory. What about the year before? You weren’t working here then. Did you have a date then?”

Eli shook his head, though he wasn’t sure why. He could have just lied. It’s not like Cassia would have known.

“That’s kind of pathetic, isn’t it?” Cassia asked.

“Hey, what the hell?” Eli shot back. “What’s wrong with you? Also, you’re here on Valentine’s Day, so what business do you have calling someone pathetic?”

“I don’t want a man in my life. Not like that, at least,” Cassia said. “And certainly not right now. A man would only slow me down. Right now my only focus is on climbing the ladder here. I’m angling for a promotion and I know they reward people who stay late and work extra hours. That’s why I know you’ll never be promoted.”

“You really don’t want a man in your life?” Eli asked as he felt a sudden and surprising sense of desire for Cassia, though he recognized that it was almost certainly because they were both single on Valentine’s Day and she could be the answer to his loneliness.

“No, I don’t,” Cassia replied. “Men my age – our age, I suppose – are pathetic creatures driven almost entirely by a desire for sex. Most of them see women as little more than masturbation devices that can walk and talk, though some prefer a woman that does very little of either. Like I said, a man would just slow me down. Men can be useful, of course, but not for dating.”

“So I’m pathetic?” Eli asked. “Is that what you’re saying?”

Cassia nodded and took a step into his cubicle. “You’re more pathetic than most, in fact.”

Eli felt a little bit feisty as he asked, “Is that right?”

Cassia smiled and reached up to unpin her dark hair. It cascaded over her shoulders and she reached up to pull it to one side before gently running her fingers through it. She undid one more button on her blouse, bringing her cleavage into full view and drawing Eli’s gaze to the soft-looking flesh of her big breasts.

“I was lying,” Cassia said.

“What? About what?” Eli asked.

She bit her lower lip and said, “About not wanting a man. The truth is, I do want a man.” Cassia stepped closer, swung Eli’s chair around until he was facing her, and bent over to put her hands on the arms. “The truth is, I want you, Eli. I’ve wanted you for months. I think about you all the time, and when I saw that you were still in the office I just couldn’t get you off my mind.”

Her lips looked impossibly soft and all Eli wanted to do was lean forward and kiss her, and since Cassia had declared her desire for him, Eli saw no reason not to. He leaned in, closed his eyes, and a moment later Cassia’s hand met his face and Eli nearly fell out of his chair at the force of the slap.

“Pathetic,” Cassia said. “Just like I said you were. You are truly pathetic, Eli. I let my hair down and put my tits on display and suddenly you think you’re the kind of man I’d be so desperate for that I’d throw myself at you in the middle of the office?”

Eli reached up to try and sooth the astonishing pain emanating from his face and he couldn’t help but notice that Cassia hadn’t buttoned her shirt back up or pinned her hair once more. Her chest was a little bit red, too, indicating at least a little bit of arousal. “You didn’t have to hit me,” he said.

Cassia smiled, and this time it seemed genuine. “No, I didn’t. I enjoyed it, though. Did it hurt?”

“Yes,” Eli said.

She stepped closer and reached up to pull his hand away from his face. Cassia replaced it with hers and Eli instantly felt better as her warm, soft skin rested against his. “I want to do it again,” she said.

“What?” he asked.

“I want to slap you again,” Cassia answered. She didn’t wait for a response. She slapped Eli across the face before he could react. It hurt just as much as the first time, if not more. He reached up to try and sooth the pain once more and she said, “Keep your hands at your sides. And stand up.”

For reasons he didn’t entirely understand, Eli stood and kept his hands at his sides as instructed. Cassia unleashed a genuinely joyful smile and raised her hand, causing Eli to flinch out of fear at being struck again.

“Take your pants off,” she instructed.

“What?” Eli asked.

Cassia slapped him across the face before he could react. “Take your pants off.”

Eli did as instructed.

“Your underwear, too,” Cassia said.

This time she raised her hand before he could object and Eli lowered his underwear a moment later, leaving his cock and balls exposed in the office.

Cassia looked down, laughed, and said, “Pathetic. Just like I thought. Look at how fucking small you are.”

“It’s…it’s cold in here, and I’m in pain,” he said. “It’s not that small when it’s hard.”

“Is it big when it’s hard?” Cassia asked.

Eli shook his head. “It’s average.”

Cassia laughed loudly. “Do you think there’s a woman in the world that wants to be with an average man, Eli? Do you think the other women in the office talk to their friends about how badly they want to fuck a guy with an average cock?”

Eli shook his head. “No, probably not.”

Cassia stepped closer and reached out to cup Eli’s balls. Her touch was surprisingly gentle as she ran her fingers over the wrinkled flesh and much to his dismay, arousal flooded Eli’s loins. His cock grew with only incidental contact and soon enough he was hard.

“You’re not average,” Cassia said as she looked down. “And I think you knew that, Eli. I think you know you’re below average. I think you lied to me.”

“I’m sor…” Eli said before crying out in pain as Cassia squeezed his balls and pulled down hard. She maintained her grip as she dragged him out of his cubicle and down the hallway. Cassia pushed open the door to their manager’s office and pulled Eli towards the desk.

“Bend over the desk, right now,” she ordered.

Eli bent over without hesitation and Cassia stepped behind him and delivered four swift blows to his ass. He cried out from the pain, but she stopped before it overwhelmed him.

“Take the rest of your clothes off,” Cassia demanded.

Eli took off his shirt, tie, and undershirt and left them in a pile on the floor before bending over the desk once more. Cassia stepped closer and grabbed two handfuls of his ass. She squeezed hard and pressed her body against his. Eli felt the softness of her breasts against his back and the warmth of her breath against his neck. He couldn’t help but moan when Cassia kissed his shoulder, but then she bit into his flesh and he cried out at the intense pain that emanated from where her teeth met his skin.

“That one’s gonna leave a bruise,” Cassia said. “Don’t worry, though. No one will see it.”

“Why are you doing this?” Eli asked.

“Because you’re pathetic, and sometimes a pathetic man deserves to be abused,” Cassia replied. “And because you lied about the size of your cock, and liars deserve to be punished.”

Cassia smacked his ass twice more and Eli winced with each blow to his soft, exposed flesh.

“Your cock is dripping, Eli,” she said. “Why do you think that is?”

Eli looked down to see that his half hard cock was almost literally dripping precum. “I don’t know,” he said as a genuine sense of confusion filled his mind.

Cassia laughed. “You don’t know? Really?”

“No, I don’t,” he said.

Cassia stepped out from behind Eli and unzipped her skirt. He kept his hands on the desk as he watched her expose her creamy thighs and a surprisingly sexy pair of pink lace panties. He wasn’t sure why, but Eli figured Cassia as the sort of girl that wore a simple cotton thong to work.

Cassia sat in the manager’s chair and spread her legs, drawing Eli’s gaze between them. She reached down, pulled her panties aside, and exposed her pussy. “Do I look wet?” she asked.

Her pussy was glistening. There was no question she was wet and Eli nodded as he said, “Yes. You look really wet, in fact.”

Cassia slipped two fingers into her pussy and the sound of her wetness reached Eli’s ears and sent a shiver of pleasure down his spine and between his legs. “You like the sound of my wetness, don’t you Eli?” she asked.

“Yes,” he admitted.

“Do you like that slapping you around got me wet?” she asked. “Do you like that spanking your ass and slapping you across the face turned me on? Do you like that treating you like the pathetic man that you are left my pussy soaking wet with desire?”

Eli nodded as he watched Cassia play with her pussy. The sight of her fingers moving in and out of her pink, slippery flesh was mesmerizing, and for some reason he really did like that she’d found such pleasure in abusing him. What was wrong with him?

“Would you like to fuck me, Eli?” Cassia asked.

“Yes, please,” he said without thinking.

Cassia stood and slapped him again. “Pathetic,” she hissed. “I would never let a man like you fuck me. You’d get all clingy and gross. You’d act like we were in love because I let you put your dick inside me. You’d beg for the chance to do it again. You’d beg and plead and you’d do it all without understanding that a man like you couldn’t possibly please me. ‘Yes, please’ was the wrong answer, Eli. The right answer was ‘that as much as you’d like to fuck me, you understand that you could never please me so you wouldn’t let me demean myself by taking your cock inside me’.”

“I’m sorry,” Eli said.

Cassia unbuttoned her blouse and took it off. Eli stared at her breasts in a pink lace bra that matched her panties, but Cassia quickly took that off too. He admired her curvy, splendid body in all its glory and he felt a desperate kind of desire to fuck her, a desire that he couldn’t extinguish.

“I’m too good for you, Eli,” Cassia said. “Far, far too good for you. I fuck real men, not pathetic boys like you. I fuck men that have dates on Valentine’s Day. I fuck men that have a long list of women that would happily go out with them on Valentine’s Day. I fuck men that know what it takes to satisfy a woman, and that will happily satisfy me and go on their way without forming some kind of pathetic attachment to the point that they become like a disgusting little dog following me around in the hopes that I’ll throw them a bone in the form of my perfect cunt.”

Cassia moved behind Eli and ran her fingers down his ass crack and between his legs. She grabbed his balls and tugged hard on them for a few moments before he felt her warm, soft flesh against his drippy cock. Cassia pressed her naked breasts against Eli’s back and stroked him until he sported a raging erection. He thought she might make him cum, but Cassia released his cock before he approached his orgasm.

“Stay right here,” Cassia said. “Keep your hands on the desk.”

Eli looked over his shoulder as Cassia walked out of the manager’s office without a stitch of clothing on her body. She disappeared around a corner and he was left naked, hard, and dripping precum as he wondered what his coworker was doing. The ding of the elevator had Eli worried that she was leaving him alone, but there was no way she’d leave the office without her clothes on.

“This is the kind of man I was talking about,” Cassia said as she returned to the office with someone Eli had never seen before walking behind her.

“What’s going on here?” the guy asked.

“This is Eli,” Cassia said. “He’s playing the part of my toy for the evening. I’ve been smacking him around as a little bit of foreplay for the fucking you’re going to give me.”

“Is that right?” the guy asked. “Can I get in on that?”

“Why not?” Cassia said. “Give his ass a few hard smacks. It feels good.”

The guy approached and Eli felt his chest tighten with panic for a moment before the hand of a total stranger struck his ass. Five more blows followed and Eli was ready to collapse from the pain by the time it was over.

“Damn,” the guy said. “You’re not kidding about him being a toy. He just takes it, huh?”

“He does,” Cassia replied. “I only discovered that tonight. I suspected he might be even more pathetic than I thought when he started working here, and it turns out I was right. I just wish I’d exposed him sooner. Think of the fun I could have had over the past year and a half. You should get naked. I need to get fucked.”

The guy stripped as Cassia moved behind Eli and ran her fingers over his ass. He thought she might beat him yet again, but she didn’t. Instead she soothed him with her soft touch and she offered kisses over his upper back and shoulders.

“I want you to watch,” she said. “Watch what it looks like when a real man fucks a woman. Watch how he makes me feel, and as you’re watching, try and be honest about whether or not you could fuck me like he does.”

Cassia moved towards the manager’s chair once more, but this time she hopped on the desk and spread her legs. The guy – who was now naked and sporting an impressively large erection – stepped between her legs. They kissed as Cassia grabbed his cock and rubbed the head over her pussy lips, producing that wondrous wet sound once again.

“Tell me you want me, Darren,” Cassia said.

“I’m desperate for you, Cassia,” Darren replied. “You know I love your pussy. You know I love fucking you. You know I love seeing you cum all over my big cock.”

Cassia took him inside her and moaned. “And you know how much I love to cum all over your big cock. Now give it to me. Fuck me hard.”

Darren leaned forward and kissed Cassia as he moved his cock in and out of her pussy. He grabbed her ass for leverage and fucked her harder. Her big tits bounced with every thrust and their mouths opened so their tongues could indulge in the same erotic dance happening between their legs.

Jealousy and awe mingled inside Eli as he watched someone else fuck the beautiful, buxom, sadistic woman that had battered his body and unlocked a kind of arousal he hadn’t known existed inside him. He wanted to be inside Cassia, and yet he understood that she was right, that he couldn’t possibly have fucked her the way Darren was fucking her. His cock was much, much smaller than Darren’s and he couldn’t provide nearly the same level of power, either.

Cassia came quickly. Quicker than Eli expected, in fact. She wrapped her arms and legs around Darren, pulled him deep into her pussy, and dug her fingernails into his back as she filled the office with wild moans of pleasure.

When she was finished, Darren pulled out and Cassia hopped off the desk. She collapsed into the manager’s chair, smiled at Eli, and said, “Go ahead and fuck him. Finish inside him, too.”

“What?” Eli said as he backed away from the desk. “No. No fucking way.”

Cassia stood and moved towards him with stunning swiftness. She grabbed a handful of his hair, pulled hard, and slammed his head down on the desk. She moved to Eli’s side and smacked his ass a dozen times. The pain resonated down his legs and up his spine and his knees trembled as he wondered if his strength would falter.

“I know what you are,” Cassia said. “You don’t even know it, but I do. I know that you’re a masochist. I know that you’re a sub. I know that you’re destined to be nothing more than a toy for a woman to use as she sees fit. Tonight, you’re my toy. You will suffer any abuse I desire, and right now I want to see Darren fuck your ass and cum inside you. Now keep your head on the desk and reach back to spread your ass cheeks so he can put that big dick of his inside you.”

Fear and a shockingly potent form of arousal filled Eli’s body as he reached back and spread his ass cheeks. His pulse raced as he did exactly as Cassia desired despite knowing that great pain would follow.

“Fuck him,” she said. “Make it hard and fast.”

Eli heard Darren spit and stroke his cock. He felt those same spit-laden fingers move over his asshole. The head of Darren’s cock then pressed against his anal opening. Eli’s body tightened up, but Darren didn’t stop trying to fuck him.

“Oh, fuck, it hurts,” Eli said.

“Yes, it does,” Cassia replied. “That’s the point, Eli. It hurts. You’re going to suffer and you’re going to do it for me. But you know what? You get to watch me masturbate while you suffer. You get to see me take pleasure in your pain. You get to see me cum while your asshole gets wrecked by a massive cock.”

Cassia released her grip on his hair and sat in the manager’s chair. She wheeled it a little closer, spread her legs, and slipped two fingers into her pussy. Eli focused on the sight of his beautiful coworker penetrating her slippery hole and did his best not to think about the intense pain emanating from his asshole.

“Fuck, he’s tight,” Darren said. “This feels so fucking good.”

“I always take care of you, don’t I?” Cassia asked. “I always make you feel good. Sometimes I suck you off after you’ve fucked me. Sometimes I let you cum inside me. Sometimes I let you cum on these perfect tits of mine. Sometimes I let you fuck a pathetic little bitch and cum in his ass.”

Darren grabbed Eli’s hips and fucked him harder, deepening the burning pain in his asshole. Eli gripped the edge of the desk and watched Cassia rub her clit and play with her tits. The pleasure on her face was real. She was getting off on watching him suffer through such deep, painful anal penetration.

“Fuck him harder,” she said. “Destroy his ass.”

Darren did as instructed. Eli didn’t think the pain could get worse, but it did. He gritted his teeth and he took it, though. He could have stopped it, but for some reason Eli didn’t even consider doing that. He just let Darren fuck him while Cassia watched and masturbated. He let himself be used as a toy. He let it all happen.

“Fuck!” Darren cried out before burying his cock in Eli’s ass and cumming.

“Cum in his ass!” Cassia said. “Fill his whore ass with your load. Breed this disgusting little bitch!” She climaxed a moment later. She grasped her breast hard, closed her eyes, and buried three fingers in her pussy while her legs trembled with pleasure. Juices dripped out of her and onto the manager’s leather chair, all while Cassia had what seemed to be a better orgasm than her first.

Darren pulled out, smacked Eli’s ass, and said, “Thanks.”

“You’re welcome,” Cassia replied. “And thank you as always.”

Darren got dressed with remarkable swiftness and left as Eli felt the other man’s cum begin dripping out of his ass.

“Thank you, Eli,” Cassia said. “You were quite the playmate tonight. I have more work to do, though. You’ll have to clean up in here. Make sure you lick my juices off his chair and clean up any cum that leaks out of your ass and onto the carpet. Do you understand?”

“Yes,” Eli said.

Cassia grabbed her clothes, smacked him on the ass, and left.

Eli turned to watch her go and then grabbed a handful of tissues from a box on the manager’s desk and stuffed them between his ass cheeks to soak up the cum dripping out of him. His asshole was astoundingly sore, but his cock was still dripping a tremendous amount of precum and he felt alive in a way he’d never felt before.

Eli turned around, leaned against the desk, and grabbed his cock. He stroked furiously as the fresh memories of the abuse he’d just suffered ran through his head. An orgasm rushed out of his body in less than thirty seconds and it left him so weak in the knees that he collapsed onto the ground. He made an absolute mess with his cum, but none of that mattered. It was the pleasure that mattered, and the pleasure was unlike anything he’d ever experienced. Maybe Cassia was right. Maybe he really was a masochist. Maybe he really was meant to be controlled by a woman. Maybe that’s what he’d been missing his whole life.