The Penalty for Being Tardy

Muffled by the handkerchief shoved in her mouth, the words "Please, mercy," struggled to be heard.

"Mercy?" he mocked. "No, I don't think so. I may have forgiven your first orgasm. But the second... oh the second was a willfully disobedient act. I cannot have that from my secretary. Willful disobedience must be met with a harsh response. You took the pleasure, you can take the punishment."

And with that he brought the cane down hard against the soft flesh of her ass and the pain shot through her like a bullet. A scream caught in her throat as her eyes watered and mouth hung open. Her arms which had been stretched out in front of her shot up, palms stretched open, fingers spread as if trying to spread the pain through as much space as possible to minimize it.

A second and third blow fell on her, and her legs quaked, knees buckled and she began sliding to the floor, until his strong hand reached between her legs and cupped her mound, pushing her back up onto the desk.

"Don't you dare whither on me on you disobedient slut," he growled. "Take your punishment or it will double."

Her sobs were now as uncontrollable as her orgasm had been. He ass burned, and she wasn't sure how many more she had to endure, or if she could endure it. She could always shout out one of her safe words, and a part of her begged her to do so. But another part wanted to take everything he could give, show that she could be his obedient girl, make her Sir proud.

The smacks of the cane became almost indistinguishable, the sharp jolts of its impacts moving through her body like waves. The pain so intense, that her entire body clenched and even her cries stuck in her throat until a moment had passed and she wailed until a new pain befell her punished ass. Her eyes were a mess of tears and smeared mascara. Her head lay on the desk, on her cheek, mouth open, the handkerchief unable to catch the puddle of drool forming beneath her head as she sobbed her regrets.

But through it all, with every new strike, the clenching and relaxing of her thighs and ass, and her own thoughts of service and submission, kept her pussy wet. Her thighs gleamed even as the welts and bruises formed.

Between the pain and humiliation, she suddenly realized that she was close to cumming again and her eyes shot wide in fear. Gritting her teeth through the cloth in her mouth, she held on as the blows kept coming, but now, the struggle was between her concentration and the interference of the pain. She couldn't let it happen again. Who knows what he would do? And the worst thought that passed her mind is that he would dismiss her and want nothing more to do with her.

Suddenly the blows stopped. Had there been 10? 20? Her face and pussy both a sloppy mess, she held still as she waited for some instruction, thighs quivering, ass burning from the brutal attention. She remained bent over the desk, her hands stretched out before her gripping the other edge. Then she heard his zipper lower.

"Ms. Welsh," he spoke calmly as she felt the cool slickness of an oil slide over her wounded ass and slip down between her cheeks. "You are a disobedient little bitch, and I cannot abide disobedient little bitches."

She felt his hands take firm hold of her hips and the head of his cock press against the tight opening of her ass. He had taken her ass before, but only when he wanted to show her that she was nothing but a collection of holes for him to fuck at will. The thought made her dizzy with desire.

As the head of his cock pressed into her, his hips brushed her tortured ass and she clenched, gripping his cock like a vice. He stopped for a moment and said. "Whether difficult or easy, whether clenched or relaxed, I am going to fuck your ass. So I suggest you relax."

She did her best to open herself, but true to his word, he held her hips and pressed forward. She was tight, but the lubrication allowed him to pry her apart, and her tight little hole stretched to accommodate him. Soon her ass was obscenely distended as the length of his thick cock opened her and she writhed under him at the not too unpleasant feeling.

Buried deep inside her, he reached forward and grabbed a fistful of her short blond hair, pulling her back onto him, stretching her neck and making her arch her back. She let out a squeal as she gave herself over to being taken. Each thrust reminding her of her caning, each thrust reminding her that she is his. Every part of her body is his. Every orgasm welling up inside her is his.

She winced as he thrusts, not from pain, but to fight off the growing need for her own release. When he had first taken her ass, she didn't understand how any woman enjoyed it, but now, accustomed to the invasion of his cock, she relished the feeling and ached to touch her clit and finish herself. But she didn't dare ask. Two stolen orgasms were more than she deserved, and if she asked, she feared he would just torture her with the edge.

Soon she felt his cock swell inside her, the tell-tale sign that only a few months before she would have never recognized. Her eyes lidded as she reveled in the feeling of his hand in her hair, forcing her back, the pleasurable soreness building inside that would soon be washed over and away with his hot seed. She moaned whorishly as she wriggled her hips as he slammed into her. She was his demure little kitten, now. The obedient fuck toy he wanted her to become.

His cock exploded inside her, filling her ass as he pumped into her. The size and girth of his cock forcing some of his cum to spill from her ass as he emptied himself. She remained wet and now his seed added to the sticky, sloppy wet that was her thighs.

When he pulled out of her, a river of semen flowed from her gaping ass, and when he released her hair, she slumped forward, panting hard and heavy, her ass sore and well fucked, unfulfilled again, but nonetheless happy to have been used by this man who signed her checks.

He took the handkerchief from her mouth, and again used it to clean himself, before tossing the expensive silk carelessly in the trash as though it were a common tissue. He put his cock away, zipped up his pants, checked himself in the mirror and straightened his tie, all while his secretary remained bent over his desk, naked and sloppy wet from the waist down, her skirt bunched around her waist, her mascara a teary mess, her ass striped with welts.

She was quite the sight.

He reached into his desk and returned behind her. Using all the various fluid already there, he shoved a vibrating plug into her well fucked ass, and she winced and grunted at the unexpected invasion.

"There you go," he said, helping her to her feet, "That should keep you nice and filled for the rest of the day. Pull you skirt down, use the restroom to fix your makeup, and return to work Ms. Welsh. We have a busy day."

She was about to protest. The mess on her legs, the soreness of her caned ass, how could she work like that? But she instead dutifully smoothed her skirt down her legs and stepped into the restroom. Looking at her tear and mascara stained face, she felt herself moisten anew as her ass squeezed the plug inside her.

As she fixed her makeup she smiled wickedly and thought, "I wonder what he'd do if I came at my desk today?" And then walked gingerly back to her desk and responsibilities.