Sabitha's Sissy Maid Pt. 01

General disclaimer: My stories revolve around both consensual and non-consensual domination. They are intended for erotic stimulation. Therefore, I take some liberties with realism. The actions, motivations and reasoning of my characters may therefore seem strange and irrational at times. The environments and settings in which my stories take place may be more or less realistic, but none of them take place in a world equal to our own. In non-consent stories, all involved characters (eventually) enjoy their outcome. English is not my first language and I apologize for my errors.

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Sipping coffee while staring down at the street from her spacious townhouse, Sabitha thought again of her many problems. Divorced since many years and retired since a few years, the days felt increasingly lonely. She didn't have many friends and made little effort to find new ones. Every day she would take walks around the neighborhood, finding that people avoided eye contact with her. Broad shouldered and with a rough, stern face, a pointy hook nose, small mouth, sinister eyes and a rather round dark bob-cut, Sabitha was no beauty. Only interested in younger men, preferably with soft features and slim figures, she knew her chances of finding a romantic partner were slim. And it didn't help that she rarely smiled at anybody. People found Sabitha to have a high degree of honesty and integrity, but also to be rude, direct and even cruel. Sabitha, in turn, did not care about how she was perceived, increasingly frustrated by empty small-talk, social jargon and niceties. Having finished her coffe, Sabitha sat down by kitchen table and opened her laptop.

As Sabitha checked her mail, she was pleased to note that her exciting plan seemed to bear fruit. The email was short, confirming that the young man Sabitha had named Cute wanted to meet. Sabitha had staged an accident where a "mistake" by Cute had led to a major power-break and supposedly harmed several people living in his building. It wasn't true that Cute had made any mistake of that people had been hurt, but in a series of devious information letters from fake authorities, Sabitha had convinced Cute that he was in serious danger of being charged and sentenced to prison. Cute had then been offered that charges would be dropped in exchange for community service. A list of eligible firms had been presented, all of them of course leading to Sabitha. After some correspondence, it was now time for Cute to meet his cunning supervisor Sabitha.

Sabitha put on some make-up, a long black leather skirt, a red blouse and ankle high black boots. A while later, she looked out from her window and could see Cute stand outside her gate. His gentle, slim look and friendly face pleased her. Sabitha walked out and let him in, cordially shaking his hand. She could sense that he was uneasy. They walked towards the door and entered the house, Cute a few steps behind. They immediately turned right into the living room where Cute was offered to sit down. Sabitha sat down on her sofa, crossed her legs and stared at Cute with a slightly annoyed face.

"It seems that you have gotten yourself into quite some trouble. I am obliged to inform you that community service is not what you may have heard of. There will be no half-measures. You will be dealt with in a continuously strict manner. This is to make sure that you honor your debt but also to teach you the value of discipline. Do you understand?"

Cute nodded, looking at the floor with a sad face.

"Look at me!" Sabitha commanded with her croaking voice, "You have been assigned household work and I am to supervise you. It is of course possible for you to walk out of here any time you like, but rest assured you will be in prison in no time, the judge has little patience for people bailing out of community service. And in prison there are many bad men waiting for someone like you."

Cute looked as if he was going to cry. "Anything miss, I will do anything, please don't put me in prison."

Sabitha spoke coldly, "You will find that I am hard but fair. Under no circumstances will you displease me. Now let's get you properly dressed for your chores."

Sabitha handed Cute a bag with clothes and told him to change in the kitchen. She leaned back and waited. After a while Cute returned, wearing a long brown wig, a tight black vest, a tight, short black skirt and a little maid hat. He looked uncomfortable and confused.

"Is this necessary, miss?"

Sabitha stood up, noticing that Cute avoided eye contact. "It is my firm belief that strict duty warrants strict clothing. And as my house keeper, your duty is to tend to my preferences. And it looks quite flattering on you, Cute. That's right, that is what your name here is. Understood?"

Cute nodded.

"Now, your outfit isn't quite complete yet. Get over here, Cute."

Sabitha placed a leather corset around his abdomen and carefully tightened the straps. Sabitha enjoyed outfitting Cute while telling him the rules.

"You will address me as mistress. You will never speak unless spoken to. Mistakes will be punished. Your only goal here is to please me until I judge that you have paid back your debt to society. Is that understood?"

"Yes," Cute responded neutrally.

Sabitha grunted, "Yes, who?"

"Y-yes mistress," Cute responded, clearly stressed.

"Good maid," Sabitha answered while moving her hand down his back, over his buns, "when you work for me, you are a little sissy maid. What are you, Cute?"

"A little sissy maid."

Sabitha was surprised by how little resistance Cute offered, although she had targeted him partly based on his soft and naive agreeability. He was clearly afraid of his fake predicament and willing to do anything. Sabitha took slow steps around Cute, declaring that she expected perfect manners and decorum. While tying a white apron with a bow around his lower back, she continued,

"You will courtesy me whenever you see me. You will keep my house impeccably clean and ordered and ensure minimal noise. Breakfast will be served at 8 am sharp, lunch at 1 pm and dinner at 6 pm. In the kitchen you have a list of my preferences."

Sabitha put her hands on Cute's shoulders while standing behind him.

"That will be all for now. I have a final gift for you. At the kitchen table you will find a pair of very beautiful white pumps and white over knee socks suitable for your outfit. Put them on and get to work, my bedroom needs tidying."

Cute turned around, curtsied and walked towards the kitchen. Sabitha admired his body, noticing his legs had very little hair for an adult male. She would soon make hair removal a part of his morning routine. Even with the profound pleasure and lust that the thought of her sissy maid brought, Sabitha walked up the stairs to the second floor with her usual cold facial expression. Cute's and Sabitha's eyes met briefly as Cute walked into the hallway, but he quickly looked in another direction. He seemed nervous and uncomfortable walking in high heels, but there was plenty of time for him to learn his mistress' ways.

Sabitha spent the day out and returned in the late afternoon. In the bin she found the lunch that Cute had made for her as instructed. Together with other observations of mistakes in the cleaning process, Sabitha decided it was time for some serious talk with her maid. She heard Cute working upstairs and went up to fetch him. He curtsied and looked at her, looking terrified.

"Come with me," she commanded him, then sat down in a heavy chair, "time for us to talk. Get on your knees in front of me with your hands behind your back."

Cute obeyed, looking nervous. Sabitha stared at him, "I see that you have wasted my food on your very first day. And the cleaning is obviously beginner's work. I'm afraid it is my duty to correct your behavior. Do you agree?"

Cute answered, clearly stressed, "Yes, mistress, I am sorry mistress."

"Since it is your first day I will be generous. Get over here and bend over my lap."

The sight of Cute bending over her leather skirt aroused Sabitha so much that she gasped.

"I want you to keep your hands firmly on your back and your legs together."

"Yes mistress."

Sabitha carefully and slowly pulled Cute's short skirt over his pale bottom. Her fingers moved gently over the buns. She then gave one of them a heavy slap. The whacking sound filled the room and had Cute instinctively jerking.

"Be still!" Sabitha said in a vile voice.

"I am sorry mistress," Cute replied, sounding anguished.

Another slap followed, and then more, with steady intervals. Sabitha was in no rush, taking time to carefully inspect her sissy maid between every spank. She was surprised by how soon his buns started to turn pink, and how hard it was for him to stay still and silent.

"This pain is necessary, it is for your own good."

The spanking continued for a long while, and eventually Cute couldn't help whimpering, louder and louder. His torso and legs jerked with every slap as the buns turned to darker shades of pink. Sabitha loved the sight of her maid's battered tush together with his degrading outfit.

"That will be all for now, Cute. I have many ways of correcting you, so be good now little sissy."

Cute stood up, curtsied, thanked his mistress and walked out of the room. His white pumps made loud noises against the creaky wooden floor. Sabitha's head was spinning from excitement over the complete control she had established over this man turned into her personal toy.

The next morning Cute served Sabitha breakfast at the assigned time. It was surprisingly perfect, Sabitha could not find anything to complain about. She enjoyed watching him work, the little skirt stretching against his tush when he leaned forward, the little apron bumping against the skirt, the white socks stretched around his lower thighs. A sissy of her dreams. She pondered why she had not done this before. One thing was certain, she would never let him go. Eventually, she would tell him about the hoax and still keep him. She had some ideas: chaining him in the apartment, using distance-operated collars, hiring guards or locking him up in a dungeon. It was a wonderful thing to think about. The sissy maid was hers, under any circumstance.

Later the same day, Cute was massaging Sabitha in her bedroom. She was lying stretched out on her bed, dressed in khaki trousers and a white shirt. Cute massaged her back up and down, gently and carefully to not upset his mistress. He was suddenly commanded to stop. Sabitha sat up and gave him a cold, stern look.

"Now that was terrible."

"Mistress, I don´t know how to, I mean sorry mistress, I will learn to do better."

Cute swallowed nervously. Sabitha stood up.

"Help me put on my shoes and then I will show you something important."

Sabitha pointed Cute to a pair of black riding boots at a shelf, he fetched them and carefully helped her put them on. Sabitha walked out of the room with Cute following behind. They proceeded through the upper floor hallway and through a small wooden door, then ascended steep stairs. They entered a large attic. Sabitha had covered the windows and equipped the room with winches, chains and a padded trestle with several large ring-shaped shackles. Cute looked terrified. Sabitha walked towards a large cupboard and opened the large doors.

"This, my dear little maid, is where I will implement most of my punishments."

Cute could see a variety of whips, paddles, toys, collars and other tools.

"The more you protest, the more severe will my punishments be."

Sabitha took a pair of thick, brown leather collars, connected by a short and thick rope, and calmly strapped them around Cute's wrists. She then positioned Cute under the roof winch. She walked over to a crank and started cranking down a thick steel chain with a large hook.

"I know it can seem cruel but I think that an efficient house maid needs clear incentives. You will probably spend a lot of time in this room, particularly in the beginning."

Sabitha told Cute to bend forward and placed the rope connecting the wrist collars inside the hook. She then cranked up the chain until Cute's arms were stretched upwards behind his back. She inspected her sissy maid carefully and folded his skirt over his pink buns. She took a white inflatable rubber gag ball from a drawer and put it in his mouth. She used an attached hand pump to inflate it, noticing that Cute struggled as it grew in his mouth, forcing him to stretch his jaws. His breathing appeared affected, with occasional coughs and facial expressions revealing distress. Sabitha looked at Cute in a sense of complete superiority. She then attached leather collars to his ankles too, connecting them to a steel bar separating his legs. Sabitha then cranked up the chain a few more notches, stretching Cute´s arms further, forcing him to bend over even more. Faster breathing and slight twitching revealed that he was affected by the treatment. Sabitha put on a tight black latex glove and poured lubricant over it. Resting her left hand on Cute´s lower back, she moved her right hand fingers in between his buns, up and down, eventually resting her index finger against his anal hole. He whimpered.

"A little tight virgin maid," she observed in her usual croaking voice, but with a slightly vicious tint.

In her fantasies, penetration of men had always served a limited humiliating purpose, but as she started working her finger into her sissy maid, to the sound of his whimpering, Sabitha was overwhelmed by the sense of complete and deep assertion of her dominance. She moaned slightly.

"Mmmm, such a tight little maid."

She began using two fingers and was surprised by the effect it had on Cute. He moaned loudly as Sabitha's fingers digging deep inside him seemed to overpower his senses. Adding a third finger, Sabitha couldn't get very deep, but the attempts at stretching the hole had Cute breathing intensely. Sabitha calmly walked over to the drawer again, fetching an oval shaped rubber toy with a leather leash. She poured lubricant over it.

"And now, my little sissy, something that will distract your mind for the next few hours, but also serve as a reminder in your further attempts to please me."

Sabitha started working the toy into Cute´s hole. Already at half its width, Cute grunted loudly.

"There, there," Sabitha calmed, looking with excitement at her sissy´s widening hole.

Cute's anus squeezed tightly around the toy, making the lubricant trickle around the part of it still outside his body. Steadily, Sabitha continued the insertion process, fascinated by Cute's muffled crying and whimpering. As the widest part entered the sissy maid, he grunted desperately, his body fixed in it's exposed position. Sabitha worked the whole toy in. She expected Cute to calm quickly but fully inside the rectum the toy still affected him greatly. Sabitha looked with pleasure at the thin leash hanging out of him, dangling between his legs. She found the entire scene a masterpiece, a fulfilled desire.

"You will stay here for a few hours, then I expect a sincere apology for your behavior."

Sabitha descended the stairs, hearing Cute's panting and whining wearing off.