A Thief's Submission

The wooden spoon scraped against the bottom of the bowl as Tessa finished her porridge. Being locked up didn't trouble her as much as it did many others. And she wasn't completely abandoned here. A servant stopped by several times a day to give her food and water and empty her chamber pot. Sometimes they spoke a few words with her.

Tessa was used to being by herself. In fact, she liked it better that way. She had found her way to the guild at a young age. It wasn't so much a choice as it was her only option. She had proved herself despite being the youngest and smallest, and they had taken her in. Tessa had kept out of the way as much as she could, trying not to get too much attention. She had been known as the quiet and serious one. One of the other young thieves used to make fun of Tessa and called her "the silent assassin". It was silly but she hadn't minded the jokes. It was just a part of their hidden society.

Over the years, Tessa had watched and learned. She graduated from being a lookout and picking pockets to taking on her own jobs. Most often she worked alone. Even so, she had taken care to always keep up with the others to get the latest information and, just as important, to make sure she didn't step on anyone's toes.

During the weeks in the cell, Tessa had slowly lost her excitement over trying to solve the puzzle of her predicament, even with the mystery box she had discovered. All she could think was, why her? There were plenty of courtesans and pleasure slaves more beautiful than Tessa. Many of them wouldn't scoff at serving a master like Rudi despite his tastes. But here she was and no one else was going to help her.

Tessa was still sitting there with her legs crossed when she heard noices outside. The door opened and Rudi bowed his head to get through. He looked down at her for a moment before he spoke. "Tessa. My naughty thief. I shouldn't be so hard on you because I could see this coming from a mile away. Old habits die hard. But I still have to know why you decided to rummage through my things. What did you hope to accomplish?"

Tessa was ready for this. Of course he would demand to know. She looked at him defiantly. "I'm a thief, remember? I was going to find the master key so I could escape. You have no right to keep me here!"

Rudi raised his eyebrows. "Oh really? I think I have all the right in the world. I remember signing your sentence myself. But I really must caution you against escape. Whatever you may think, I have no desire to see you hurt or worse. However, actions must always have consequences. I will see you soon Tessa."

After that, Tessa knew it wouldn't be long before she was allowed back up again. She wasn't sure if she was looking forward to it or if she would rather eat porridge and stare at the walls for a bit longer. There had been a dangerous gleam in Rudi'd eyes. It was strictly forbidden to cause lasting harm to a slave unless they were guilty of a serious violation. But she certainly didn't underestimate the ability of her master to come up with something unpleasant.

Just as she had expected, a servant came for Tessa the very next day. She brought Tessa to the servants' quarters and made sure she cleaned herself very thoroughly. Rudi arrived before it was finished and watched with quiet intent. She felt the urge to cover herself although he'd seen it all before. Afterwards, Tessa stood before him with goosebumps on her skin.

Rudi gestured for Tessa to kneel in front of him and bent down to fasten a leather collar around her neck. Then he attached a thin chain to a metal ring on the collar. He tugged on it and turned to leave. Tessa started to rise to follow him. "What are you doing? You will crawl on your hands and knees until I say otherwise." She knelt down again, then placed her hands on the floor in the humiliating position. He was going to walk her like a dog! But if this was to be her punishment then so be it.

The hard stone floor hurt her knees. Tessa made small careful movements to make it easier. Rudi didn't pull on her leash and let her decide the pace. When they reached the soft carpets of the main areas, she sighed with relief. Other members of the household snuck glances at Tessa in her naked splendor. Some looked at her with pity, some were indifferent. If they enjoyed seeing her youthful forms bent in submission, they certainly didn't show it in front of the master. Rudi walked just behind Tessa now. She was aware of her butt swaying when she crawled, probably seductively. She tried to stop it but quickly decided that it wasn't really possible. Not if she wanted to keep moving forward.

There was a sudden agonizing sting on her buttock. Tessa arched her back and whimpered from the pain. She turned her head and saw Rudi holding a long thin switch in his hand. He raised it again and Tessa's stomach lurched as she embraced for the inevitable. The pain was just as bad on the other side. "Stop wasting my time time. I will teach your little ass what it means to disobey me." Tears were welling up in Tessa's eyes but she angrily blinked them away. She wouldn't give him the satisfaction. Rudi went ahead of her and pulled on the leash. She scrambled to keep up.

They continued to a part of the house that was seldom used. Rudi led her into a room and closed the doors. It was sparsely furnished with a few balloon back chairs along the walls and a worn sofa with embroidered cushioning by the opposite end from the door. A portrait of a solemn man looked down on them. Perhaps an ancestor or even the father. This was where Rudi would make her perform whatever lewd act he had in mind. "Are you going to be a good girl or do you need another taste of the whip?" Tessa winced, she did not want that. It wasn't too hard to swallow her pride. "Please master, I will be a good girl. I promise."

Rudi removed his clothes without any hurry while Tessa knelt beside him. He sat down on the sofa and unhooked the chain from Tessa's collar. He pointed to his lap. Tessa clambered on top of him, her ass in prime position for whatever he wanted to do. Strong hands squeezed and stroked Tessa's bottom for a while. She felt his manhood rising under her.

Tessa drew in a sharp breath as he spanked her. First one side, then the other and back again. He didn't use as much force as he could have, but it still burned a fair bit. Even so, Tessa couldn't help herself. "Do you really think you can teach me with a simple spanking?" He barked a short laugh. "Well perhaps not. You are such a hardened criminal after all. But there's no harm in trying. Now spread your legs a little more and open up your ass for me."

Tessa knew that a slave couldn't expect her asshole to be protected from her master's attention. It was just the way of things. But she had never before been forced to give up this most private part of herself. Tessa reluctantly reached back and parted her soft asscheeks. She felt exposed and a shiver ran through her. Rudi touched her senstitive opening with his finger. He rubbed it and pressed just a tiny bit. It tickled, and Tessa fought to keep from squirming.

With a sinking feeling she felt him applying a generous amount of lubrication both on the inside and around the rim. Rudi pressed a little harder with his finger and her anus allowed it to slip inside. He pushed the finger in and out, twisting and bending it. The intimate and somehow dirty pressure against her inside just felt so wrong.

After a while, Rudi gave her ass a light slap to indicate that the preparation was done. "You know what comes next darling. Get on top of me, and face the room." Tessa really didn't want to do this but she had no choice. He would use the whip again and then he would just take her anyway. Now that surrendering her anal virginity was finally about to become reality, it felt like a point of no return. Rudi applied lubrication on his cock, which stood in stiff anticipation. Tessa steadied herself with a hand on his leg. Awkwardly she eased her butt down backwards with her legs spread.

With a gasp, Tessa felt the tip of his cock against her lubed up asshole. Rudi teased and rubbed against the opening. "Don't worry, I'll be gentle." Tessa's valiant ring muscle gave way with effort. "Ooh, ouw!" That hurt! It was just so big and her ass hugged it very tightly. Tessa felt the invasion with her whole body. She shifted carefully to find a better position, leaning back into him and trying to let her sphincter relax.

Rudi sucked on her earlobe and fondled her breasts. "Mmm Tessa, your ass is so tight. Go on and ride me." Tessa's face was hot but she started moving up and down slowly, with tiny motions. Her asshole was stretching in place rather than sliding along his cock. There was a strange feeling in her ass now, almost like an aching but not quite. She really couldn't describe it.

Her thoughts were interrupted by Rudi's voice. "Oh I almost forgot. I have a visitor today. I'm sure you don't mind if we welcome him right now, my pet." He rang a bell and Tessa felt a jolt of panic. An unremarkable man in maybe his late twenties soon entered and approached them. He took in the scene with obvious appreciation. Tessa was burning with shame. She thought he had the posture of a guard, while lacking the uniform. The boots were right though. There was something about him, but she didn't want to look at him for anything in the world. She wanted to disappear.

Rudi greeted him. "Welcome my friend. Since you serve me so well, I thought it only fitting that you should be allowed to admire my wonderful new little thief. Say hello to the good man Tessa." Rudi hugged her waist and pushed his dick further in, almost as far as it could go. Tessa only moaned.

The newcomer spoke. "She is truly something my lord. And she is learning well already. You will enjoy her plenty I reckon." He kept staring at Tessa. She could imagine what he was seeing. The former thief with a grimace on her pretty face. The slave riding her master, her obedient tight ass almost swallowing the whole length of his shaft. The humiliation of it made Tessa close her eyes.

But there was definitely something about him. As they kept talking, Tessa forced herself to look at him again. Suddenly she knew. She had seen him a few months back with Jasmine in a tavern. They had been sitting with their heads close together in a corner where they could see everyone who came near. Jasmine was one of Tessas least favorite members of the guild. She never seemed to do any jobs herself, but she stuck her nose into everying. Even the scruffiest and meanest thieves became meek as lambs when she smiled at them, with her velvety eyes and rosebud lips. What was happening here? Just then Rudi had apparently had enough. Their visitor took a last glance at her and left.

Rudi turned his full attention to Tessa once again. The utter humiliation of being seen like this had somehow melted her defenses. Rudi played the part of a gently lover. He let her decide the pace and kissed her behind the ear. They settled into a slow but steady rythm. Like the divination cards with one fate on each side, they belonged together but their roles were the opposites. For him it was the ultimate conquest. For her, the ultimate surrender.

Rudi reached to rub her clit. Tessa caught herself clenching hard on the dick massaging her inside. Sickening slivers of pleasure ran through her body. It would have been so easy to just give in and welcome the humiliation, to let it become fuel for a twisted desire. But she couldn't, there would be no going back.

Rudi started working with his hips to accelerate their anal lovemaking. He was grunting and breathing heavily. Now there was pain mingled with pleasure. Tessa's body responded by trying to follow his movements up and down to soften the penetration. But it was hard when her parted legs dangled helplessly above the floor. Rudi didn't let her get away. He hugged her from behind and fucked her ass with deep strokes. Tessa panted fast. Her yielding asshole was now all that existed. She felt like it would keep on being stretched by his slick cock forever. But at last, after a few twitching thrusts and a spasm, Tessa felt him pulse inside her. There was a warm squishy feeling in her bowels.

Tessa leaned back into her masters embrace. Right now, she didn't have the strength to think about anything, least of all the implications of what she had just discovered. She only felt like a slave, a lover, an exhausted woman with her master's half erect cock still buried in her ass. His caresses and soft whispers didn't bother her, they were just a part of the here and now. Tessa closed her eyes and rested her head on his shoulder.