Chrissie The Saga of a Lovestruck Sissy Maid
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A LADY'S SISSY MAID: PARTS 1-3 free porn video
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.”
To be continued………..
A Lady’s Sissy Maid – Day Two
Following his initial interview with Mistress Enya, Steve now had to wait at home for a written critique of his interview. If Mistress deemed him appropriate he would be invited to return for additional training, she made it perfectly clear that if there were to be a second interview he would be thoroughly tested.
Almost two weeks passed and he had given up hope of hearing from this Goddess that he desired to serve. When he arrived home, there in his mailbox was a pale pink envelope; it was sealed with a gold stamp, embossed with the initials “M.E.” and he was addressed to Maid Stephanie which instantly made him blush, knowing that his mailman surely snickered at the name. Steve ripped it open and eagerly read the short note written in elegant handwriting almost as if it were written in calligraphy. It read:
“Maid Stephanie, I am pleased to advise you that you have been selected to proceed to the next phase of the interview process. I found your desire to please refreshing and it made up for some glaring flaws that I will correct at our next meeting. You are to attend to me at my suite located at #60, Columbia Street on Saturday at 12 noon.”
Steve spent that evening preparing his uniform and he decided to impress his Mistress by preparing a plate of baking for her to enjoy.
He arrived promptly at noon and rang the buzzer at the front door. He was instructed to wait at the front door while Mistress came down to admit him into the building. At the time, movers were in the process of assisting a new resident to move into the building, which oddly enough made Steve nervous. When the elevator door opened, Mistress Enya emerged looking even more refined and elegant than during his initial interview. She wore black stiletto heels, black stockings, a conservative black skirt, tight pink blouse that slowed off her magnificent breasts and a tailored jacket. She was such a sight that even the movers stopped to stare as she approached Steve, she took him by the elbow and lead him back to the elevator in such a manner that even though it was subtle, it was clear that she was in charge.
Back at the apartment she pointed towards the washroom,
“You may get dressed and report to me for inspection.”
Steve hurriedly changed into his uniform and in his rush he got a run in his stocking. He didn’t have time to change it, so he decided that it would be better to take his chances with a minor uniform flaw, versus taking too long to get changed. He dashed out into the living room where Mistress was relaxing and glancing at a coffee table book filled with dominant Mistresses and their slaves.
“You may present yourself for inspection.”
Mistress pointed to the middle of the room where he nervously stood.
“Slowly turn around so I can see your uniform.”
As he did he heard a disapproving sign, which he assumed, meant that she saw the run in his brand new stockings.
“Lift your dress up so I can see your knickers and slowly turn around again.”
Once again he did as commanded and then stood facing her with his eyes downcast. He could see her reach over to the coffee table and pick up a small notebook and pen. She made some notes and then in a sharp, controlled tone instructed him,
“You may prepare me some tea and clean up the dishes.”
For the next few minutes he went about his duties and tried to familiarize himself with the immaculate kitchen. He laid out a selection of various teas on a small plate and returned to the living room so that Mistress could make a choice. He was hoping that this little added touch would please her, but if it did she did not let on. Mistress merely made a choice and dismissed Stephanie back to the kitchen. Stephanie was mildly hurt by her lack of appreciation; he moved onto phase two and presented her with the plate of six different types of baking.
“Maid Stephanie please describe to me what each of these selections are.”
Stephanie explained each in detail and once again she coolly dismissed him back to his chores.
“Maid Stephanie I have brought along a very nice video tape that you may place in the VCR to watch while you complete your tasks. It’s a very erotic video and I hope that you take note of the maid’s conduct.”
As Stephanie readied the tea and cleaned the kitchen, he watched a very demure blond maid waited, on a seductive black and white video, of a Mistress with a strong resemblance to Mistress Enya. Stephanie noted that his Mistress found the nature of the maid very pleasing, he was fairly certain that this video was not just for his enjoyment, but rather a subtle indication of what she expected of him.
He presented the tea to his Mistress and then obediently stood by her side while she sipped her tea, nibbled on the sweets and enjoyed the remainder of the video. She took particular delight with the ending where the Mistress administered a severe spanking on the white bottom of the maid. Stephanie grew nervous at this time, because as it was unfolding on the TV screen, Mistress Enya had reached up under his skirt and was teasingly rubbing his knickered bottom.
“You may eject the video and return it to me.”
Stephanie did as he was told; he then kneeled at her side, not because she instructed him to, but rather because he sensed it to be appropriate. Mistress opened up the coffee table book again and for the next 15 minutes she slowly leafed through the book, which was filled with gorgeous Mistresses putting slaves through very humiliating and sometimes painful training. All of this visual stimulation was too much for Stephanie; as he kneeled beside Mistress Enya, he could not help but to stare at her ample bosom, he desired to reach out and touch them because he had a strong bra fetish and could only imagine that she was wearing a very sexy brassiere. Looking at the photos in the book only made it worse and she tormented him further by continually crossing and uncrossing her legs. What he wanted more than anything in the world was for her to allow him to worship her body.
Without warning she closed the book,
“Go place that chair in the middle of the room!”
Stephanie did as he was told and then stood beside Mistress Enya.
“Now then Stephanie I have made some notes that will require correction. Firstly, stockings with runs are unacceptable; you must stop purchasing inferior quality stockings. Secondly, 2 ½” heels will not do, your comfort is secondary to your appearance. I require 4” to 5” heels that will improve the look of your legs. In addition your uniform is incomplete; you need gloves as well as a maid’s cap to be a proper maid. I expect and so do my guests, that a maid is feminine and appealing to the eye, your posture is also far from acceptable. I have a very special way of improving your posture which I will reserve for another day should you not improve it on your own.”
Mistress then stood up and walked over to the chair, she sat down and without a word Stephanie knew his place was across her lap. He nervously lowered himself across her lap, she flipped up his skirt and without a word his knickers were pulled down around his ankles. Mistress then delivered a long, slow spanking on his bare bottom, allowing enough time between each smack to let the sting set in. After what seemed like 50 smacks it was over.
“Thank you Mistress.”
“You may stand in the corner Stephanie and think about what I have told you today.”
Stephanie quickly pulled up her knickers and stood in the corner with her nose firmly pressed against the wall. Mistress chatted on the telephone for a few minutes and only stopped when there was a knock at the front door.
“Stephanie!! You may answer the door!!”
Mistress was clearly annoyed by Stephanie’s slow response to the door and even slower response to her command. She walked over to her maid who had a shocked look on her face, a quick sharp slap across the face followed by 4 or 5 across the bum were enough to get Maid Stephanie moving.
Mistress pointed to the front door and without a word Stephanie nervously walked over.
To be continued……………
A Lady’s Sissy Maid – Part 3
Maid Stephanie apprehensively walked over to the door and opened it, the lady on the other side was initially shocked at the sight of this maid, but the shocked expression was quickly replaced with a smile.
“Aren’t you a dear, I do hope you’re better than the last maid Mistress Enya had in her employ? Take my bag won’t you?”
She held it out, then simply dropped it on the floor, forcing Stephanie to bend over and retrieve it. As she did, she felt the firm grasp of a hand reach under his frilly dress and fondle his bottom.
“Well you do have a nice bottom don’t you?”
Stephanie blushed, “Thank you ma’am.”
Mistress Enya and her guest greeted each other and retired to the living room to chat while Maid Stephanie prepared some tea for his Mistress and her guest. She presented a tray with tea for the ladies and immediately Mistress Enya’s guest asserted her wishes.
“Maid, you may call me Frau Schmidt. Now I’ve been on my feet all day and I need to put my feet up.”
Stephanie was confused so he looked at his Mistress for guidance, with a flick of her wrist she signaled him to get down on his hands and knees. Maid Stephanie realized then that he was expected to be a footstool. She did as she was told and Frau Schmidt, who was a larger lady, roughly put he heavy legs across Maid Stephanie’s back and relaxed while she and Mistress Enya chatted about the benefits of having a maid.
Frau Schmidt was completely different than Mistress Enya; Ms Enya had a reserved and refined manner about her that commanded respect without it having to be implied. On the other hand, Frau Schmidt was much more direct and forceful and Maid Stephanie already feared her.
After 15 minutes of idle chit chat, Frau Schmidt announced,
“Well Enya, I think it’s time to do some evaluating of your little maid to determine where she needs improvement. Maid Stephanie, kneel before me.”
Frau Schmidt lifted her legs and Stephanie quickly repositioned herself at the lady’s feet. Frau Schmidt raised her shoe up towards Stephanie’s face and she instinctively knew that she was to remove the shoe. He kissed the top of the shoe before removing it, Frau S. presented her other foot and she repeated the procedure.
Mistress Enya spoke from the sofa beside her friend,
“Maid Stephanie you may attend to Frau Schmidt’s feet as she has had a long day.”
Stephanie admired Frau Schmidt’s immaculately pedicured foot through the flesh colored stockings and slowly kissed each of her toes, she then took Frau’s foot gently in her hand, as if it were a delicate piece of jewelry and leaned forward to take her big toe between her lips, to suck on it as if it were a male sexual organ.
“Oh my sissy, you seem to yearn to use that mouth of yours, don’t you?”
She reached down took Sissy’s chin in her hand and guided it up towards her face.
“Fetch my purse dear, while I chat with Mistress Enya for a moment.”
Stephanie returned with the purse, curtsied and handed it to Frau S.
Mistress Enya stood up and announced to Stephanie,
“I’m going to leave you with Frau Schmidt while I run down to the store to pick up some items so that you can prepare us an adequate meal this evening. While I’m gone, you are to follow her instructions and pamper her as she is a valued guest. If she reports any misconduct or poor behavior you will be dealt with like never before. Do you understand?
Stephanie helped Mistress Enya on with her coat and opened the door for her; it was the wicked little smile that Mistress Enya gave Frau Schmidt that had Stephanie worried.
“Maid Stephanie; come with me, would you?”
Frau Schmidt’s already forceful tone was even more dramatic now. She turned and headed towards the spare bedroom. Maid Stephanie followed and Frau S. closed the door behind her once Stephanie was in the room.
“Maid, I have some washing for you to do, you may remove my knickers, hand wash them in the sink and blow dry them while I lie down and relax.”
Maid Stephanie was not sure what to do next because Frau S. just stood there with her hands on her hips.
“Come come you sissy, remove my clothing. Can’t you perform the most basic of domestic chores?”
Maid Stephanie hurriedly unbuttoned her blouse and unzipped her tight, form fitting skirt. As she was helping Frau S. step out of her skirt, Maid Stephanie lost her balance ever so slightly and to steady herself, she accidentally placed her hand on Frau Schmidt’s rear end. Frau Schmidt was shocked and accused Maid Stephanie of inappropriate behavior. Maid Stephanie apologized profusely but Frau S. cut her off.
“You may remove my knickers with your lips, then carry them to the sink in your mouth and wash them. Then report back to me once they have been rinsed and dried.”
Stephanie carefully removed her delicate knickers and scurried off to the adjoining bathroom to do her assigned task. Frau Schmidt laid down on the bed, wearing just her bra and suspender belt set, to browse through a selection of magazines on the nightstand.
Once the knickerss were dried, Stephanie reentered the bedroom and was shocked to find Frau Schmidt quietly pleasuring herself with a vibrating dildo that she had discovered in the nightstand. With one hand, she massaged her breast through the lace bra, while the other slowly glided the flesh colored dildo between her legs. Maid Stephanie had never seen anything so erotic in her life and she could feel her penis grow hard in her panties.
Frau Schmidt suddenly opened her eyes to discover Maid Stephanie standing there with one hand under her frilly skirt.
“How dare you!” Frau Schmidt snapped.
Frau S. quickly got up, walked over to the maid who was now shaking with fear and grabbed her by the ear.
“I’ve never seen such a disgraceful thing in my life! Your role is to serve and pleasure your Mistress and her guests not spend your time peeping on a guest and to make things worse, you were seeking personal satisfaction. I can only imagine how Enya will deal with you but in the meantime, you will need to make yourself useful. Lie down on the bed, facing up and remove your knickers.”
Maid Stephanie did as she was told, seconds later Frau Schmidt climbed on the bed and straddled his face with her warm, sweet smelling womanhood inches from his face.
“Now then Sissy, you are to use your lips and tongue to please me and while you are, you will also masturbate yourself at the same time. You are to continue to please me until I reach an orgasm and as an added incentive, should you orgasm before me, you will face the consequences.”
She lowered herself down onto his waiting mouth and for the next 20 minutes or so he feverishly did his best to complete his assignment. Frau S. ground her sexuality into his face and literally made love to his mouth, at the same time, she added to his torment by instructing him to pump his penis faster and faster until to his dismay, his cum squirted out.
Instead of feeling pleasure he let out a moan in despair Frau S. laughed softly,
“Very well Sissy wipe up your mess with your fingers and lick them clean.”
Stephanie did what she was told as Frau S. watched, once satisfied that everything was cleaned up, she grabbed Stephanie by the ear and lead her out into the washroom. With one hand she pressed Stephanie’s chest down against the vanity as she reached into the medicine cabinet for a jar of Vaseline she dipped her fingers into the jar, gathered up a thick glob, pressed it against his virgin bottom spreading it around his tight opening. Stephanie was expecting the obvious but instead, Frau Schmidt raised her hand up and began giving him a nasty, bare bottom spanking for the next 5 minutes. She smacked his bottom with a steady rhythm and didn’t even pause or lessen the impact as Stephanie squirmed and cried out in pain. She finally stopped when she was satisfied that Stephanie’s soft, white bottom had the perfect warm, rosy glow to it that signaled a well learned lesson.
“Follow me!”
Frau Schmidt went out into the living room as Stephanie followed, she then took Stephanie’s ear and lead her to the corner, pressing her nose against the wall, but before leaving she slipped a penny between the wall and her nose.
“You can stand her until Enya returns; if the penny falls, you’ll be over my knee.”
Frau S. straightened out Stephanie’s uniform and retired to the sofa to watch TV in her lingerie and await the return of her friend.
Respectfully submitted by Mistress Enya’s Sissy Maid
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.”
To be continued………..
A Lady’s Sissy Maid – Day Two
Following his initial interview with Mistress Enya, Steve now had to wait at home for a written critique of his interview. If Mistress deemed him appropriate he would be invited to return for additional training, she made it perfectly clear that if there were to be a second interview he would be thoroughly tested.
Almost two weeks passed and he had given up hope of hearing from this Goddess that he desired to serve. When he arrived home, there in his mailbox was a pale pink envelope; it was sealed with a gold stamp, embossed with the initials “M.E.” and he was addressed to Maid Stephanie which instantly made him blush, knowing that his mailman surely snickered at the name. Steve ripped it open and eagerly read the short note written in elegant handwriting almost as if it were written in calligraphy. It read:
“Maid Stephanie, I am pleased to advise you that you have been selected to proceed to the next phase of the interview process. I found your desire to please refreshing and it made up for some glaring flaws that I will correct at our next meeting. You are to attend to me at my suite located at #60, Columbia Street on Saturday at 12 noon.”
Steve spent that evening preparing his uniform and he decided to impress his Mistress by preparing a plate of baking for her to enjoy.
He arrived promptly at noon and rang the buzzer at the front door. He was instructed to wait at the front door while Mistress came down to admit him into the building. At the time, movers were in the process of assisting a new resident to move into the building, which oddly enough made Steve nervous. When the elevator door opened, Mistress Enya emerged looking even more refined and elegant than during his initial interview. She wore black stiletto heels, black stockings, a conservative black skirt, tight pink blouse that slowed off her magnificent breasts and a tailored jacket. She was such a sight that even the movers stopped to stare as she approached Steve, she took him by the elbow and lead him back to the elevator in such a manner that even though it was subtle, it was clear that she was in charge.
Back at the apartment she pointed towards the washroom,
“You may get dressed and report to me for inspection.”
Steve hurriedly changed into his uniform and in his rush he got a run in his stocking. He didn’t have time to change it, so he decided that it would be better to take his chances with a minor uniform flaw, versus taking too long to get changed. He dashed out into the living room where Mistress was relaxing and glancing at a coffee table book filled with dominant Mistresses and their slaves.
“You may present yourself for inspection.”
Mistress pointed to the middle of the room where he nervously stood.
“Slowly turn around so I can see your uniform.”
As he did he heard a disapproving sign, which he assumed, meant that she saw the run in his brand new stockings.
“Lift your dress up so I can see your knickers and slowly turn around again.”
Once again he did as commanded and then stood facing her with his eyes downcast. He could see her reach over to the coffee table and pick up a small notebook and pen. She made some notes and then in a sharp, controlled tone instructed him,
“You may prepare me some tea and clean up the dishes.”
For the next few minutes he went about his duties and tried to familiarize himself with the immaculate kitchen. He laid out a selection of various teas on a small plate and returned to the living room so that Mistress could make a choice. He was hoping that this little added touch would please her, but if it did she did not let on. Mistress merely made a choice and dismissed Stephanie back to the kitchen. Stephanie was mildly hurt by her lack of appreciation; he moved onto phase two and presented her with the plate of six different types of baking.
“Maid Stephanie please describe to me what each of these selections are.”
Stephanie explained each in detail and once again she coolly dismissed him back to his chores.
“Maid Stephanie I have brought along a very nice video tape that you may place in the VCR to watch while you complete your tasks. It’s a very erotic video and I hope that you take note of the maid’s conduct.”
As Stephanie readied the tea and cleaned the kitchen, he watched a very demure blond maid waited, on a seductive black and white video, of a Mistress with a strong resemblance to Mistress Enya. Stephanie noted that his Mistress found the nature of the maid very pleasing, he was fairly certain that this video was not just for his enjoyment, but rather a subtle indication of what she expected of him.
He presented the tea to his Mistress and then obediently stood by her side while she sipped her tea, nibbled on the sweets and enjoyed the remainder of the video. She took particular delight with the ending where the Mistress administered a severe spanking on the white bottom of the maid. Stephanie grew nervous at this time, because as it was unfolding on the TV screen, Mistress Enya had reached up under his skirt and was teasingly rubbing his knickered bottom.
“You may eject the video and return it to me.”
Stephanie did as he was told; he then kneeled at her side, not because she instructed him to, but rather because he sensed it to be appropriate. Mistress opened up the coffee table book again and for the next 15 minutes she slowly leafed through the book, which was filled with gorgeous Mistresses putting slaves through very humiliating and sometimes painful training. All of this visual stimulation was too much for Stephanie; as he kneeled beside Mistress Enya, he could not help but to stare at her ample bosom, he desired to reach out and touch them because he had a strong bra fetish and could only imagine that she was wearing a very sexy brassiere. Looking at the photos in the book only made it worse and she tormented him further by continually crossing and uncrossing her legs. What he wanted more than anything in the world was for her to allow him to worship her body.
Without warning she closed the book,
“Go place that chair in the middle of the room!”
Stephanie did as he was told and then stood beside Mistress Enya.
“Now then Stephanie I have made some notes that will require correction. Firstly, stockings with runs are unacceptable; you must stop purchasing inferior quality stockings. Secondly, 2 ½” heels will not do, your comfort is secondary to your appearance. I require 4” to 5” heels that will improve the look of your legs. In addition your uniform is incomplete; you need gloves as well as a maid’s cap to be a proper maid. I expect and so do my guests, that a maid is feminine and appealing to the eye, your posture is also far from acceptable. I have a very special way of improving your posture which I will reserve for another day should you not improve it on your own.”
Mistress then stood up and walked over to the chair, she sat down and without a word Stephanie knew his place was across her lap. He nervously lowered himself across her lap, she flipped up his skirt and without a word his knickers were pulled down around his ankles. Mistress then delivered a long, slow spanking on his bare bottom, allowing enough time between each smack to let the sting set in. After what seemed like 50 smacks it was over.
“Thank you Mistress.”
“You may stand in the corner Stephanie and think about what I have told you today.”
Stephanie quickly pulled up her knickers and stood in the corner with her nose firmly pressed against the wall. Mistress chatted on the telephone for a few minutes and only stopped when there was a knock at the front door.
“Stephanie!! You may answer the door!!”
Mistress was clearly annoyed by Stephanie’s slow response to the door and even slower response to her command. She walked over to her maid who had a shocked look on her face, a quick sharp slap across the face followed by 4 or 5 across the bum were enough to get Maid Stephanie moving.
Mistress pointed to the front door and without a word Stephanie nervously walked over.
To be continued……………
A Lady’s Sissy Maid – Part 3
Maid Stephanie apprehensively walked over to the door and opened it, the lady on the other side was initially shocked at the sight of this maid, but the shocked expression was quickly replaced with a smile.
“Aren’t you a dear, I do hope you’re better than the last maid Mistress Enya had in her employ? Take my bag won’t you?”
She held it out, then simply dropped it on the floor, forcing Stephanie to bend over and retrieve it. As she did, she felt the firm grasp of a hand reach under his frilly dress and fondle his bottom.
“Well you do have a nice bottom don’t you?”
Stephanie blushed, “Thank you ma’am.”
Mistress Enya and her guest greeted each other and retired to the living room to chat while Maid Stephanie prepared some tea for his Mistress and her guest. She presented a tray with tea for the ladies and immediately Mistress Enya’s guest asserted her wishes.
“Maid, you may call me Frau Schmidt. Now I’ve been on my feet all day and I need to put my feet up.”
Stephanie was confused so he looked at his Mistress for guidance, with a flick of her wrist she signaled him to get down on his hands and knees. Maid Stephanie realized then that he was expected to be a footstool. She did as she was told and Frau Schmidt, who was a larger lady, roughly put he heavy legs across Maid Stephanie’s back and relaxed while she and Mistress Enya chatted about the benefits of having a maid.
Frau Schmidt was completely different than Mistress Enya; Ms Enya had a reserved and refined manner about her that commanded respect without it having to be implied. On the other hand, Frau Schmidt was much more direct and forceful and Maid Stephanie already feared her.
After 15 minutes of idle chit chat, Frau Schmidt announced,
“Well Enya, I think it’s time to do some evaluating of your little maid to determine where she needs improvement. Maid Stephanie, kneel before me.”
Frau Schmidt lifted her legs and Stephanie quickly repositioned herself at the lady’s feet. Frau Schmidt raised her shoe up towards Stephanie’s face and she instinctively knew that she was to remove the shoe. He kissed the top of the shoe before removing it, Frau S. presented her other foot and she repeated the procedure.
Mistress Enya spoke from the sofa beside her friend,
“Maid Stephanie you may attend to Frau Schmidt’s feet as she has had a long day.”
Stephanie admired Frau Schmidt’s immaculately pedicured foot through the flesh colored stockings and slowly kissed each of her toes, she then took Frau’s foot gently in her hand, as if it were a delicate piece of jewelry and leaned forward to take her big toe between her lips, to suck on it as if it were a male sexual organ.
“Oh my sissy, you seem to yearn to use that mouth of yours, don’t you?”
She reached down took Sissy’s chin in her hand and guided it up towards her face.
“Fetch my purse dear, while I chat with Mistress Enya for a moment.”
Stephanie returned with the purse, curtsied and handed it to Frau S.
Mistress Enya stood up and announced to Stephanie,
“I’m going to leave you with Frau Schmidt while I run down to the store to pick up some items so that you can prepare us an adequate meal this evening. While I’m gone, you are to follow her instructions and pamper her as she is a valued guest. If she reports any misconduct or poor behavior you will be dealt with like never before. Do you understand?
Stephanie helped Mistress Enya on with her coat and opened the door for her; it was the wicked little smile that Mistress Enya gave Frau Schmidt that had Stephanie worried.
“Maid Stephanie; come with me, would you?”
Frau Schmidt’s already forceful tone was even more dramatic now. She turned and headed towards the spare bedroom. Maid Stephanie followed and Frau S. closed the door behind her once Stephanie was in the room.
“Maid, I have some washing for you to do, you may remove my knickers, hand wash them in the sink and blow dry them while I lie down and relax.”
Maid Stephanie was not sure what to do next because Frau S. just stood there with her hands on her hips.
“Come come you sissy, remove my clothing. Can’t you perform the most basic of domestic chores?”
Maid Stephanie hurriedly unbuttoned her blouse and unzipped her tight, form fitting skirt. As she was helping Frau S. step out of her skirt, Maid Stephanie lost her balance ever so slightly and to steady herself, she accidentally placed her hand on Frau Schmidt’s rear end. Frau Schmidt was shocked and accused Maid Stephanie of inappropriate behavior. Maid Stephanie apologized profusely but Frau S. cut her off.
“You may remove my knickers with your lips, then carry them to the sink in your mouth and wash them. Then report back to me once they have been rinsed and dried.”
Stephanie carefully removed her delicate knickers and scurried off to the adjoining bathroom to do her assigned task. Frau Schmidt laid down on the bed, wearing just her bra and suspender belt set, to browse through a selection of magazines on the nightstand.
Once the knickerss were dried, Stephanie reentered the bedroom and was shocked to find Frau Schmidt quietly pleasuring herself with a vibrating dildo that she had discovered in the nightstand. With one hand, she massaged her breast through the lace bra, while the other slowly glided the flesh colored dildo between her legs. Maid Stephanie had never seen anything so erotic in her life and she could feel her penis grow hard in her panties.
Frau Schmidt suddenly opened her eyes to discover Maid Stephanie standing there with one hand under her frilly skirt.
“How dare you!” Frau Schmidt snapped.
Frau S. quickly got up, walked over to the maid who was now shaking with fear and grabbed her by the ear.
“I’ve never seen such a disgraceful thing in my life! Your role is to serve and pleasure your Mistress and her guests not spend your time peeping on a guest and to make things worse, you were seeking personal satisfaction. I can only imagine how Enya will deal with you but in the meantime, you will need to make yourself useful. Lie down on the bed, facing up and remove your knickers.”
Maid Stephanie did as she was told, seconds later Frau Schmidt climbed on the bed and straddled his face with her warm, sweet smelling womanhood inches from his face.
“Now then Sissy, you are to use your lips and tongue to please me and while you are, you will also masturbate yourself at the same time. You are to continue to please me until I reach an orgasm and as an added incentive, should you orgasm before me, you will face the consequences.”
She lowered herself down onto his waiting mouth and for the next 20 minutes or so he feverishly did his best to complete his assignment. Frau S. ground her sexuality into his face and literally made love to his mouth, at the same time, she added to his torment by instructing him to pump his penis faster and faster until to his dismay, his cum squirted out.
Instead of feeling pleasure he let out a moan in despair Frau S. laughed softly,
“Very well Sissy wipe up your mess with your fingers and lick them clean.”
Stephanie did what she was told as Frau S. watched, once satisfied that everything was cleaned up, she grabbed Stephanie by the ear and lead her out into the washroom. With one hand she pressed Stephanie’s chest down against the vanity as she reached into the medicine cabinet for a jar of Vaseline she dipped her fingers into the jar, gathered up a thick glob, pressed it against his virgin bottom spreading it around his tight opening. Stephanie was expecting the obvious but instead, Frau Schmidt raised her hand up and began giving him a nasty, bare bottom spanking for the next 5 minutes. She smacked his bottom with a steady rhythm and didn’t even pause or lessen the impact as Stephanie squirmed and cried out in pain. She finally stopped when she was satisfied that Stephanie’s soft, white bottom had the perfect warm, rosy glow to it that signaled a well learned lesson.
“Follow me!”
Frau Schmidt went out into the living room as Stephanie followed, she then took Stephanie’s ear and lead her to the corner, pressing her nose against the wall, but before leaving she slipped a penny between the wall and her nose.
“You can stand her until Enya returns; if the penny falls, you’ll be over my knee.”
Frau S. straightened out Stephanie’s uniform and retired to the sofa to watch TV in her lingerie and await the return of her friend.
Respectfully submitted by Mistress Enya’s Sissy Maid
India
- 14.06.2022
- 50
- 0
