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https://xhamster.com/stories/a-ladys-sissy-maid-parts-1-3-620129
A LADY'S SISSY MAID: PARTS 1-3
A Lady’s Sissy Maid - Day One

Steve was single and it had been awhile since he was in a meaningful relationship, so one Saturday afternoon, he was aimlessly perusing a local fetish contact newspaper when a particular ad caught his eye. It read:

“Sissy Maid Sought by Refined Beauty"

Classy, beautiful and refined lady is in search of a sincere sissy to perform my household duties and become my personal servant. Applicants must be docile, follow instructions and have a sincere desire to serve and satisfy this high class lady, who will only accept the best. A proper uniform will be provided. You must be well versed in all domestic duties as well as understand the role of a sissy maid. Perfection is expected therefore poor performance will be dealt with in an appropriate manner. Strict forms of domestic discipline are practiced in my household. Submit your resume to: Ms. Enya Box 41637 New Westminster, V3M 6L1

For some reason the wording of the ad intrigued Steve, he mulled it over for the afternoon and considering that since he was an only c***d and his mother taught him to be respectful to women, to cook, do household chores and to pamper any woman he was with, he felt that he had the credentials sought by Ms. Enya and had nothing to lose by responding to the ad.

He sat down and wrote about his upbringing and his experiences with the women in his life. He detailed his formal chef training and how nothing in the world would please him more than to make a beautiful lady’s life more pleasurable. He hurried to the post office to mail his letter and a week later a package arrived in the mail. It contained a book titled “A Charm School for Sissy Maids” by Mistress Lorelei and a note that advised him to read the book and if he was still interested in the position he was to call a mobile number to arrange for an appointment.

He read the book that evening and the more he read the more he realized that this was destiny, he was perfectly suited to be a Sissy Maid. He eagerly called the number and spoke with Ms. Enya, she provide him with some basic details and instructions to attend her residence on Saturday at 2:00pm sharp. Ms. Enya had a pleasant tone, yet it was clear by her demeanor that she would not put up with improper behavior.

He had difficulty finding a parking spot and when he rang the entrance buzzer to her luxury condo building he was a few minutes late. He was admitted and preceded to her floor, he rang the doorbell and within seconds he heard the distinctive sound of high heels walking on hardwood floors. The door opened slowly and before him stood a strikingly, gorgeous lady with her dark hair up in a bun and piercing green eyes, that looked as if they belonged to a Goddess. Steve always admired a lady with shapely legs and he immediately noted that she was wearing black stiletto heels and fine black stockings that accentuated her shapely legs. She wore a very classy and expensive looking black leather skirt and a crisp, white blouse that did little to hide the fact that she was wearing a black brassiere, which held her ample breasts high as they strained against her white blouse. Instantly Steve could feel something stirring in his pants as he gazed upon this beautiful woman.



“Welcome Steve, it is a pleasure to meet you”, Mistress Enya said smiling as she motioned him to enter and shook his hand.

Once the door was closed, she gave him a hug and playfully patted him on the bottom. With that, she turned around and motioned him to follow, instantly Steve’s eyes noticed that she was wearing seamed stockings and her shapely bottom filled out her skirt beautifully. To accentuate this, after a few steps she bent over to pick up some unseen object on the floor. This was clearly for his benefit as now her skirt rode up revealing her stocking tops and suspender belt tabs. She straightened up, looked over her shoulder, gave a wicked little smile that was almost a smirk and strutted into the living room while Steve followed along like a little puppy.

She walked over to the mantle and picked up a container that held numerous folded slips of paper.

“Steve, take a slip and have a seat while we chat a little.”

Steve took a slip and noticed that Mistress had gorgeous painted nails and wore tasteful, refined jewelry. The stirring in his pants was now becoming uncomfortable so he quickly sat down fearing that Mistress would notice the bulge in his pants. She glided past him and sat down on the sofa across from him, letting her figure hugging skirt slide up a few inches, then seductively crossed her legs revealing her stocking tops ever so slightly. Poor Steve was clearly falling under her charms; in embarrassment he caught himself staring at her shapely legs so he looked up towards her face, only now he staring at her breasts, he couldn’t help but notice the details of her black lace bra through the thin white fabric of her blouse.

“What time is it?”

Steve looked at his watch, “2:10pm ma’am”.

“What time were you to arrive?”

Before he could reply she answered her own question, “2:00pm sharp not 2:05pm!”

“I, I, had difficulty parking Ma’am.”

“I do not except excuses so consider yourself warned.”

Steve was a little stunned at how her pleasant demeanor quickly changed to being more authoritative yet remained refined. At this point, she began to explain the position and her requirements,

“The position is plain and simply, the position of house and personal maid, the successful applicant will handle all household duties that are beneath my attention. It is your objective and desire to humbly and respectfully serve a Dominant in the objective of cleaning, servitude and housekeeping. This means all cooking, cleaning, laundry, ironing, answering the telephone as well as serving me in all manners that I choose. The sissy maid is expected to learn from her mistakes and take punishments as required from misbehavior, incorrect application of training or attitude adjustment. Each day upon your arrival, you will receive a typed list of tasks to be completed and other miscellaneous duties that I may desire you to perform. Let me make myself perfectly clear because I never want to have to repeat this to you. The sole duties of my maid are to please me and make my life more enjoyable. After a long difficult week I expect to be pampered, as a lady of my stature deserves, this may include massages, pedicures, bathing me or even allowing me to take out my frustrations in my own special way. Please understand that I am a fair and loving Mistress but I also expect nothing less than perfection, upon the completion of each task it will be inspected and graded depending on my level of satisfaction or dissatisfaction you will either be praised or more importantly corrected. Correction may be immediate or some time later, my methods of correction are fair and in line with the level of dissatisfaction. Now on to some basic rules:
1. You may only speak when spoken to.
2. I shall be addressed as Mistress, Madam or Goddess.
3. Upon entering the room you must curtsy before me.
4. When I arrive home I am to be greeted at the door with my favorite beverage.
5. Your uniform will always be properly worn and subject to inspection.
6. All duties are to be performed without question.
7. Following your punishment you must thank me.

Now I am going to give you a moment to think about my rules and expectations, if you do not feel that you can live with these basic rules you are free to leave.”

Mistress then got up and left the room so Steve could ponder his fate. The erection in his pants was now raging and although he was scared to death, there was no way that he could get this gorgeous woman and her curvaceous body out of his mind.

Mistress returned and before she could say anything Steve said, “I wish to continue my interview to be your Maid.”

Mistress smiled, “Very well Stephanie, follow me.”

Although she said it in a kind and loving tone she grasped him firmly by the elbow and led him down the hallway, as if he were a c***d.

“You may remove your clothing, place it in this bag and report to me in my bedroom.”

Steve did as he was told then anxiously and cautiously entered her bedroom where Mistress was busying herself in the closet. Steve was both scared and aroused and to maintain his modesty he covered his genitals with both hands. Mistress turned around, put her hands on her hips, which only extenuated her womanly figure and authoritative demeanor.

“Put your hands behind your back”, she snapped.

Steve was shocked at her tone and immediately did as he was told, his erect penis jumped out and Mistress Enya’s only reaction was a short sigh of disgust. Without a word she inspected him by slowly walking around him and Steve instinctively lowered his head in shame. She playfully patted his bottom and whispered,

“You have a lovely bottom that will look lovely in some frilly knickers and perfect for some other pleasures.”

While she still stood behind him she continued to tease and torment him by reaching up with both her hands and running her manicured fingers playfully over Steve’s swollen nipples and massaging his fleshy breasts causing him to give out a gasp.

“Hmmm, my oh my, you have lovely breasts that are even more sensitive than a woman’s, an added bonus is that they are fleshy enough to almost fill out a bra, without even adding some padding. Only a true sissy would have such girlish breasts. Are you a virgin Stephanie?”

“No, Mistress I am not”, he responded in an insulted tone.

“Oh you silly thing, I think you may have misunderstood the form of virginity I was referring to”, she said with a little chuckle.

Mistress walked over to her dresser, picked up a wooden hairbrush, playfully patting it against the open palm of her hand. Steve was now looking up and admiring her beautifully rounded bottom. Without turning around to face her perspective maid she began a short but stern lecture.

“In my advertisement I mentioned that I expect perfection and in order to begin our relationship on the proper footing I am required to maintain consistent control by administering correction for all faults so that they never happen again. Unfortunately, you have put me in a position where I must correct a problem already. I asked you to pull a piece of paper from my crystal bowl earlier that is what I call my “Punishment Bowl”. Your punishment will consist of whatever is written on the slip of paper. Before our next session you will be required to prepare twenty slips containing various forms of punishment that you think would be appropriate for various misdemeanors. Now I am going to assist you with putting you in this girdle and stockings, the remainder of your uniform you can do yourself. Once properly attired, you will present yourself to me for inspection and your first taste of correction.”

Mistress smiled to herself when she saw that “Stephanie” was sniffling softly, she ignored him and proceeded to slip him into the open bottom girdle, then attach his sheer black stockings to the suspendes. A playful slap on the bottom followed and without a word Mistress left the room while he quickly got dressed. Once all the clothing was on, he caught a glimpse of himself on the full length mirror, although he was clearly male in facial features, the bra, filled with silicone breasts combined with the girdle and finally the very short skirt, complete with puffy crinoline, gave him a sissy look.

He teetered out into the living room, curtsied as required and presented himself for inspection. He stood perfectly straight, with his head bowed and his arms as his side while Mistress Enya carefully inspected every detail of his uniform for what seemed like ten minutes.

Finally she broke her silence, “Very well, you may go put on the water for my tea as well as prepare a proper tray for my enjoyment, then while the tea is infusing, you are to report back for your punishment.”

Stephanie quickly retired to the kitchen and readied the tea and tray with selection of baked goods he prepared. Although there were nagging fears in the back of his mind he was amazed at how at peace he felt with serving such a beautiful woman who commanded both respect and devotion. In less than thirty minutes he learned what it felt like to be in the presence of a Goddess. Once the kettle was turned on, he straightened his uniform and returned to the living room, thankfully, he remembered to curtsy as he entered. His only error was that he had left the slip of paper in the washroom with his “boy” clothing. Mistress Enya was clearly annoyed when informed of his over sight as she merely pointed down the hall.

Stephanie dashed as quickly as he could in his heels, then to make matters worse, he couldn’t find the slip of paper, the sound of Mistress’ heels clicking on the floor towards the washroom created panic in his heart, then when they stopped, he sensed she was behind him and he dreaded to look.

“Is there a problem?” she snapped.

Before he could respond, she grabbed him by the ear as if he were a c***d and led him into her room.

“Turn around, face that mirror, lean forward and place your hands on your knees. I want you to see your own face as you receive your first punishment.”

He felt a shiver through his body as he felt Mistress Enya flip up the back of his uniform to expose his ruffled panties, then without a word, she placed one hand against his back while the other lightly caressed his knicker covered bottom, slowly worked it’s way down to the tender part of his naked thighs and stocking covered legs. Just when he was beginning to relax and enjoy the tenderness of her touch, he saw her reflection in the mirror as she raised her hand and delivered 5 or 6 solid smacks on his knicker covered bottom.

Stephanie squirmed and yelped as her smacks suddenly transformed the loving gentle touch of seconds ago to sheer pain. She stopped for a moment causing him to think that she lesson was over, but once again that momentary sense of relief was shattered when she roughly grabbed the waistband of his knickers and yanked them down around his ankles.

“Oh my goodness, you are such a baby!! Be quiet or I’ll stuff those knickers into your mouth and give you a spanking that you’ll never forget. Do you understand?”

Stephanie sniffled and nodded and once again the spanking continued with 10 more smacks on his bare bottom. The whistling of the kettle most certainly saved him from a longer spanking.

“Pull your knickers up and serve the tea for me in the living room when I arrive.”

For the next few minutes Stephanie waited in the kitchen with everything prepared but his Mistress did not arrive. He could hear rummaging in her room but that was all, she retired to her luxurious sofa and rings a small bell signaling him that she was ready to be served .She appeared pleased by the effort he made in providing some small desserts for her to enjoy with her tea. Once her cup was poured, she instructed him to kneel at her feet. Once she finished her first cup, he refilled, then she said in a more loving tone,

“Stephanie you may worship my feet and legs, I will leave it to you to decide on what will bring me the greatest pleasure.”

He did his best by combining both gentle kisses and caresses to her feet, which were still clad in gorgeous heels and her calves were amazing! She appeared to enjoy the attention and as he approached her knees she parted her thighs signaling him to kiss and caress her luscious, stocking covered thighs. His penis was on the verge of exploding and he just about lost it when she said softly,

“Lean back and close your eyes I have a special surprise for you.”

As she said this, she stood up, there was the unmistakable sound of her unzipping her leather and of her stepping out of it. Stevie could only dream that he was going to be given the opportunity to worship this Goddess in the most intimate way. Even though his eyes were still tightly closed he could sense that she was moving closer and he opened his mouth slightly, at that moment she took his head between her hands guiding it closer to her body.

“It’s time to worship me, you may open your eyes and mouth.”

As he did she forcibly filled his mouth with the strap-on dildo she had slipped on under her skirt while following that initial spanking. He struggled for a moment, but there was no use and for the next while he received lessons in how to service a cock.

Eventually his Mistress allowed him to a “release” with the warning that he must catch it all in his hand or suffer the consequences. He reached an intense orgasm and was relieved that none had escaped but that relief was short lived because he was ordered to smear his cum onto the head of her strap-on dildo and then lick it clean. Once complete she added,

“Some day soon these lessons may come in very handy.”

Tillagd 12 feb 2019   Noveller   #Man #Kvinna

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