“I won’t go any lower than twelve.”

I was sweating, but Mr. Johnson looked calm. He’d been calm for the whole fucking negotiation, all forty-five minutes of it. He was slouched in his black leather chair behind his large, elegant desk, with the faintest hint of a smug smile on his face. No matter how hard I pushed or what threats I made he kept that smug smile.

“I do believe you’re lying, Mr. Henry,” he said, as I felt the sweat collecting at the ridge of my brow.

“I… I… okay. I can do ten, but no lower, honestly.”

He broke into a real grin.

“I think that will do nicely. Shake on it?”

I thought I heard a faint zipping sound, like a fly being done up, but I dismissed the thought as ridiculous. A second later he stood up, hand outstretched. I reached over the desk and took the hand with a sigh of relief.

Finally that nightmare was over.
____________

That pompous fool Henry droned on and on about meaningless things. I mostly ignored him. I was focused on the sensation of my slave’s lips on my cock. No one has ever questioned why I wanted such a big desk. They thought it was an ego thing. They were wrong. I have a large desk so that I can fit a fucktoy inside of it.

The fucktoy was locked inside the desk with only her hands and lips free. There’s a false panel on one side through which she crawls in and a system of stocks that lets me lock her arms and head in so that she can do nothing but suck me off. I get her nice and horny in the morning and she knows that the only way she can get off is if she does a good job.

Some days she gets lucky and I get off her off at lunch, but that’s a rare treat for her. Most lunches I get myself off in one of her holes with no regard for her pleasure.

The days I relish the most are those where she gets careless though. If she makes even the slightest noise I give her a punishment she remembers for weeks.

Finally, Henry came to some sort of offer. He was sweating profusely, terrified by my smug insouciance. He didn’t realize I was too busy being sucked off to care about most of what he had to say.

His offer sounded reasonable, but I wanted to see how far I could push him.

“I do believe you’re lying, Mr. Henry.”

I saw him crack before he realized it. A decade of breaking people had taught me what the moment looked like.

“I… I… okay. I can do ten, but no lower, honestly.”

I broke into a happy grin. Not only had I talked him down, but also here was an occasion to test my slave.

“I think that will do nicely. Shake on it?”

I felt the pause in her bobbing and then the frantic heat of her fingers on my cock, as she pulled up my underwear, zipped up my fly, and did up my button and belt. Her fingers were practised at this task and fast, but I heard a slight sound as she did up my fly.

Herny looked down at the desk for a confused moment, but shrugged it off when I stood up and offered him my hand.

He then beat a hasty retreat out of my office.

I sat down and hummed to myself. I felt the fucktoy’s fingers on my pants, but I didn’t give her the chance to try and placate me. I locked them in a steely grip.

“Now, now, pet, none of that. You know the rules.”

I felt her hands begin to tremble. I leaned back in my chair and began to hum. There was no point in rushing things. Proper form required me giving her some time to panic.
____________

I don’t have a name anymore. I had one once, but now I answer to fucktoy. My job is simple: keep my master happy. When he’s happy, I’m given pleasure. And when he’s angry, I’m punished.

I spend my days locked up in his desk, sucking him off and providing him pleasure on his breaks. Some days I am good and he gives me pleasure in the mornings and at nights. Most days I face a long, exhausting, frustrating wait before I finally feel his fingers inside of me and get the feeling I crave.

And some days I am bad and get the punishment I deserve.

I was hoping today would be a good day. I kept my master hard and close to coming throughout a business meeting that felt like it was going on forever. I sucked him even though my throat was sore, even though my tongue was tired, even though the rough wood dug into my side and I wanted to cry. I tried to be a good slave and do what I was supposed to.

I heard happiness in his voice and I knew I was doing well. I’d learned the signs to watch out for since this became my life. If master did most of the talking, if I could feel tension in his thighs and hear it in his voice, then I knew I wasn’t doing well enough. But if master let the other person do most of the speaking, if he was relaxed in the chair and I could here smugness in his voice, then I was doing my job right.

I always half-listened to his conversations. Not to eavesdrop, but because sometimes I had to stop in a hurry. Sometimes he stood up. These were the times I dreaded because it was so hard to get his pants done up quickly without making any sound.

I was just dreaming about the feeling of master’s fingers inside me, teasing me, making me beg him for permission to come when I heard the words that started me trembling.

“I think that will do nicely. Shake on it?”

I stopped sucking immediately and moved my head back to the extent my painful restrains allowed. I pulled up his boxers and his pants and zipped his fly. In the silence beneath the desk, it sounded loud, but surely I’d been quiet enough. Surely I’d done it right. I trembled as I did up his belt.

He stood up as soon as I was done. I heard footsteps out of the room and then I saw him sit back down. I reached for his pants, eager to keep up my ministrations and earn my reward, but his hands reached out and stopped mine.

He gripped me so hard it was painful. I stifled a cry. Maybe if I was quiet enough, he wouldn’t hurt me. Master forgave me sometimes, if I was being good before I made a mistake. He was a merciful master; maybe he’d let me go with just a warning.

“Now, now, pet, none of that. You know the rules.”

My heart sank. He let go of my hands. Walked to the door and said something through it to his secretary. She responded and he began to chat with her.

She knew about me of course. I’d even serviced her on occasion, if master was feeling generous. She’d been a slave once, but master had been pleased enough to promote her. Now she didn’t have to worry about being punished.

He talked with her for ten minutes while I quietly cried. Finally, he closed the door. There was a dull finality to the sound. He didn’t sit back down, didn’t give me a chance to plead with him.

“Please…” I whispered.

I felt the breeze as the compartment I crawled in through opened.

“For that, you’ll count an extra twenty.”

I began crying in earnest, but I didn’t let any sound escape.

“The total count will be one hundred. Then I will use both of your holes. You’ll also spend the rest of the day with a butt plug in. Hopefully this will encourage you to learn your lesson.”

There was only one thing to say. “Yes master, thank you master.”

“You’ll count out each slap and beg me for more. If you make any noise beyond that, I’ll add five. And you’ll beg me to let you clean off my cock once it’s been in your ass.”

“Yes master!”

I heard swishing sounds and braced myself. Nothing came.

Once he’d gone this far only to forgive. I couldn’t help but hope that this would happen again. I relaxed, I couldn’t stop myself. Master was a good master. He loved me.

That’s when the smack came. From the agonizing fire, I could tell he was using his cane. I was instantly bruised. I knew the welts would only grow, that by the end I’d beg for anything if it would just make it stop.

As I dutifully started counting, I remembered that master’s love meant he sometimes had to punish me.
____________

“Ninety nine master! Please one more!”

I sipped from my glass of water. Whippings were hard work and my arm had begun to get sore. I’d taken a few breaks and used those breaks to slowly take off my clothes. At my last break, I’d gotten myself hard by rubbing my cock all over her slit and ass. She ground into me without being able to help it, desperate for pleasure and my cock despite the pain.

“I’m not convinced you’re genuine. Beg me some more”

Beneath all the welts and thin lines of blood that decorated her ass, I could see her shaking. She was terrified of what would happen if she didn’t convince me.

Just as it should be.

“Please master! Please punish me! I know that you love me and that you know best! I know you do what you do so that I can become better! Please punish me! I want to be better for you!”

I rewarded her stirring speech with one last slap. It left another bloody line. Her tough skin had held up almost to the very end.

“One hundred master!”

I dropped the cane and walked over to her.

“Does your ass hurt slave?”

“Yes master!”

I grabbed it roughly. I massaged the flesh roughly between my hands. More blood welled to the surface.

“Then here, let me massage it.”

“Thank… thank you master!”

I could hear the pain in her voice, sweet music to my depraved ears. Her shaking legs made me smile.

I took a break from my torture and rubbed my dick up against her from behind. She could feel how hard I was and began to beg me to take her, hoping to stop the torture for good.

I teased the entrance to her slit with my cock. She moaned and begged, even though she wasn’t quite wet yet.

I worked myself in more roughly than I would have normally. If she wanted to divert me, I was going to make it hurt. The friction produced a lot of wonderful sensations for me and some delightful whimpers from her.

But after a few strokes she was as wet as a splash pad. I began to pound into her, burying myself fully.

I’ve always loved the feeling of burying myself in a woman. There’s such a release of tension. As her pussy squeezes my cock and I feel the intense pleasure, I can finally relax. This is what I was made for. Everything else is just a game.

The point of this wasn’t to hurt her – although she was giving tiny whimpers every time my groin banged against her tortured ass – I’d have time to do that with her asshole. No, the point here was to get her as horny as possible. The real torture would be the rest of the day, with a gently vibrating butt plug keeping her constantly aroused and focusing her mind on the memory of my cock inside her.

Soon enough her whimpers were replaced by genuine moans. I kept banging into her faster and faster, but she was ignoring the pain in favour of the pleasure growing inside of her. I was beginning to get close to coming, which meant it was time to stop. I still had to fuck her ass after all.

____________

After the spanking, master began to massage my ass. I thanked him as best I could, despite the horrible pain. My knees wanted to give out, but I couldn’t let them. The restraints in the desk were sharp and uncomfortable; if I let my weight fall on them, I’d only be hurt more.

Just as the pain was almost unbearable and I prepared myself to cry out and accept the consequences, master stopped. I felt his dick pushed up against me and tried to grind into it. If I could distract him with fucking me, I could earn a reprieve.

It was going to hurt a bit, but it would save my mauled ass from yet more pain.

“Do you want my cock inside of you, fucktoy?”

I seized the opportunity as best I could.

“Yes master! Please put your hard cock inside of me! Use me as a hole!”

He grunted and began to push into me. I bit my lip against the sharp pain of his entry, but kept myself silent. After a few strokes, it stopped hurting. Even him slamming against my ass was only a small note of pain in the symphony of pleasure master’s cock was playing inside of me.

As he sped up, I pushed back into him. I was soaking wet now and I could feel the distant glow of an orgasm, visible but not yet close. Before it had a chance to get any closer, he pulled out of me.

Then I felt his hands on my hips and his cock at my asshole.

“Beg me to take you in the ass dry. Make me believe it, or I’ll give you another fifty strokes so that I can use your blood to lube me up.”

I swallowed. I hated dry anal sex. It hurt and it kept me aroused without any hope of orgasm. But I knew I couldn’t take any more hits of the cane.

“Please use my asshole! I’m nothing but holes! I want you to use me like the toy I am! Please fuck me like I’m worthless! Fuck me in the ass!”

I said whatever I though would work. The searing pain of his cock pushing past my hole greeted its success.

This time there was no gentleness. He furiously fucked my ass and all I could do was bear the pain silently. I didn’t grind into him or try and take him deeper. It wasn’t about my pleasure.

As he ravaged my ass, I let the shame of making a noise overwhelm me. This was the punishment I deserved.

____________

Her asshole hadn’t had any chance to relax and was extremely tight. It was a wonderful. And she couldn’t relax into my thrusts thanks to the pain, guaranteeing that it would keep feeling this good.

Within a minute, I felt myself close to coming. I redoubled my pleasure, delighting in my slaves pained breathing.

As I fucked her as fast as I could, I began to feel the orgasm starting deep inside my balls. It slowly overtook me, until my knees became weak with the pleasure of it and I saw stars behind my eyes. My cock began to shoot ropes of cum into her ass and her tight asshole seemed to suck every last drop of it out of me.

I collapsed against the side of the desk for a second, but quickly recovered. There was one last thing I needed to do.

I quickly pulled my cock out. Before she could relax, I grabbed the waiting butt plug and forced it inside of her. Her breath caught violently from the pain, but she didn’t make any other noise. She was well trained. I set it to vibrate gently and then closed the door of the desk. The thick wood of the desk blocked the sound of the vibration.

She didn’t even let the pain of that violation throw her off her game. As soon as the butt plug was inside her, she began to beg me to let her suck my cock clean so that she could earn my forgiveness.

I gingerly sat back down in my chair and yanked on my fucktoy’s hair. She got the message and began to slowly suck me off. I thought I could feel a few tears falling on me.

I began to whistle jauntily. It had been a good day and it wasn’t even lunch yet.

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