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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.
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"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.
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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.
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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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