Sissy and Missy

Sissy and Missy II

Copyright 2020 Christopher D.B.

Note from the author: This story is part two of a series. Please read the original story, Sissy and Missy, which can be found at Literotica.com.

My black high heeled pumps made a hollow clonking sound on the worn marble treads as I made my way up the stairs with the ornate iron railing.

While my shoes looked like leather, they were from a discount department store and the label inside the uppers said they were all manmade materials. That didn't bother me because they fit well and were comfortable. The heels were three and a half inches tall, which I always think of as a good height for a woman to wear to the office. High enough to be sexy, but not so tall as to be slutty.

The French maid costume that I wore was another story. It certainly looked slutty with pink satin and white ruffle trim, all too revealing, but it was cheaply made and starting to fall apart. I had actually made some emergency repairs to it downstairs just moments ago, and I hoped that Countess Tori wouldn't notice. Now that I had a decent pair of shoes, it was time to get another maid uniform.

At the top of the stairs, I opened the door to the main room of her play space. Countess was seated on her throne. Missy was by her side, operating a laptop computer on a small wheeled table. They were discussing today's schedule.

I stopped just inside the door, my eyes cast downward, and waited to be addressed. From what I overheard, they would be very busy today.

Countess Tori is a professional dominatrix and does sessions for hire, mostly for wealthy male clients. I am a man of modest income, and had been able to work out an arrangement with her to get sessions at a discount, in exchange for working as her sissy maid every other Saturday.

"Sissy, are you ready to go to work?" Countess asked me at last.

"Yes, Countess," I replied as I approached her throne and did a modest curtsy.

She is a heavy set woman and today wore her thin blonde hair in a single long braid. Dressed in form fitting black leggings that had a leather look to them, and black leather thigh high boots that laced up the front, heels probably five inches tall. Most impressive though was the black leather and chrome studded busier, which shaped her large breasts amazingly perfect. It would have been easy to stare at them too long, which would have gotten me in trouble.

"My schedule is full today but I might be able to fit you in for a short session if there is a cancellation. Are you interested?" she asked. I was thrilled since it had been over a month since she had been available for a session.

"Yes, Countess, it would be an honor to have a session with you," I humbly replied.

She told me that today she needed me to do a thorough cleaning of the large office suite on the second floor. It had been vacant for a long time and a tenant had recently signed a lease and would be moving in soon.

"Missy has a list of tasks and will escort you downstairs," she explained. "Now I see you have a new pair of heels but you will be using a ladder for part of your work today so she will have you change into a pair of flats."

I'd been looking forward to wearing my new pumps, so I was disappointed to hear that.

"Now show me that you are secure and then get to work," she ordered.

I raised my apron and the front of my dress, and then briefly pulled the front of my panties down for her inspection. My penis was secured in a locked chastity device. As a sissy maid I usually worked unsupervised and Countess did not want me masturbating on her time, so I was required to wear it when I served her.

"Very good," she said with approval. "Missy, take sissy downstairs, and provide him with some reasonable inspiration to do a good job."

"Yes, Countess," she said with a submissive tone, and then headed eagerly towards the door.

As I followed Missy down the stairs, our high heels clattered loudly, echoing in the stairwell. She always wore the same pair of black patent ankle boots with a short set of laces up the front. They had tall platforms and the heels were at least six inches high, like the ones a stripper might wear.

Her sexy ass was proudly displayed with a shiny black PVC thong, and her modest breasts were also exposed with a matching open cup PVC bra. Missy was a few decades younger than me and was pretty, in a way. I always thought she could look hotter if she let her hair grow out and removed some body piercings, but then again she had too many tattoos for my taste.

Missy was a submissive personal assistant to Countess Tori, as well as a dominatrix in training. I also accidentally discovered the last time I served the Countess, that Missy might be her love interest, or at least be required to satisfy her sexual needs. I was supposed to obey Missy, though she was usually supervised by Countess Tori, and was not immune from being punished.

Missy wore her usual a law enforcement style utility belt of wide black leather, with two rows of large chrome grommets and several leather snap pouches. She had a pair of shiny handcuffs worn on the belt above one hip, and a small round rubber paddle hung on the other side.

In the past, Missy had always had a stubby riding crop hanging from her belt, but today that little chrome snap hook dangled empty.

The last time I had served the Countess, Missy had given me a harsh whipping with her little crop. That had been discovered by Countess Tori, who must have taken away her crop for now.

I followed Missy down to the second floor and towards what I thought of as the locker room. It was a tiny narrow room at the end of the hallway, near the restrooms and fire escape exit. A group of metal lockers along one wall, and a metal folding chair were the only furnishings. This room was where I changed into my sissy maid outfit. It was also where men who came to Countess Tori for sessions would disrobe and lock up their clothes.

At this time there were no locks on the other lockers, and no clients waiting, so I assumed Missy got to change clothes upstairs, a privilege of her position.

"Those are nice new heels, sissy. I know you're disappointed that you have to take them off. Are you going to cry?" Missy taunted.

I just fumbled with my combination lock in silence. Missy and I weren't supposed to speak to one another unless it was related to a task or session, and she knew that.

There is a narrow window at one end of the locker room, it overlooks an alley below, and Missy opened that window as I changed into a pair of silver metallic flats.

I was somewhat surprised when she pulled a pack of cigarettes and a lighter from a pouch on her utility belt.

"Get over here and lick my boots while I read your list of chores, you sissy bitch," Missy ordered as she lit a cigarette, and then turned her head to blow a plume of smoke out the window.

Now I assumed that smoking wasn't allowed in the building but it wasn't my place to say anything to her about it. I just got down on my hands and knees and crawled over to Missy to lick her ankle boots.

The black patent finish was scuffed in a number of places, and had light cracks in others. If they were mine I would throw them out and buy a new pair. I think this was the only pair of boots I'd ever seen Missy wear.

She continued to smoke her cigarette and read aloud my list of chores. It was really only working in the large vacant office suite on this floor. The usual vacuuming and dusting, but I also had to get out the step ladder to clean light fixtures and wipe down the wood trim.

Surprisingly I wasn't required to wash windows, but as I slowly licked the heel of one of Missy's boots, the rubber tip mushroomed out from heavy wear, I thought that I would clean the windows if I had the time.

Missy then tossed her cigarette butt out the window, closed it, and dropped the list of chores on the floor.

"Now let's go to that office," Missy said, unclipping the paddle from her utility belt.

She led the way down the hall, periodically slapping the round rubber face of the paddle in the palm of her hand.

I was pretty sure that Missy was looking forward to spanking me, and I was a bit nervous about that. Every paddle has its own unique flavor of pain, for the lack of a better term. I know Missy has spanked me with that paddle in the past but I couldn't recall how bad it had been, since she preferred to use a riding crop. The paddle would have to be easier to endure than the crop.

Inside the office suite, the main room still had an L-shaped secretary's desk, along with an uncomfortable looking wooden chair. Missy ordered me to drop my panties around my ankles, and then pull up my maid's dress and lean over the desk.

She placed one hand on the small of my back, holding up the hem of my dress, and started to swat my bare ass with her paddle. There were no pauses to tease me, or swirling caresses of the paddle on my butt cheeks. Just firm snaps of the rubber paddle on one cheek of my ass and then the other. It hurt a bit more than expected, but to my surprise, she didn't give me that long of a spanking.

"Get to work, bitch!" she said, clipping the paddle back onto her belt. "Countess may have me check on you, so don't be lazy." With that, Missy left the office, and moments later I heard her high heels ascending the stairs.

After pulling my panties up, I looked through the office suite, walking off my spanking, in a sense. It was part of my regular sissy maid work to dust and vacuum in the vacant offices, so really the place was clean enough for the average tenant.

Flipping on the lights in each room, I saw that most of the fixtures had light cobwebs on them or a dead fly inside. I thought I might clean light fixtures first, since that would be easily noticed. Then maybe the trim, which was all stained and varnished wood. A nice classic look in this old building located in the historic district.

Countess Tori had owned the building for several years. The first floor had two rental spaces that were little boutique shops and accessed from the street. I never had to do any work down there. The upper floors of the building are accessed through a locked door to the street on the first floor of the stairwell.

Countess has a buzzer and intercom upstairs and can discretely let clients into the building, and when I was out in the second floor hallway to get my cleaning supplies and the ladder, I heard someone come in and start up the stairs.

There were a number of rental offices on the second floor. At this time, only two of the smaller offices were occupied, and I had never seen the tenants.

One of them was a mostly retired architect or engineer that supposedly only worked when he was bored. The other was a private accountant that also kept odd hours. I wasn't responsible for cleaning their spaces and had never met them. It could have been one of the tenants coming upstairs, but I thought it was most likely Countess Tori's first client of the day.

I had been instructed that if I should ever encounter one of the tenants or a client, I should avoid eye contact and was not allowed to speak to them. If some dude saw me all dressed up in my frilly maid dress here in the Countess's building, I really didn't care. However, if it was a client I assumed they would want discretion and prefer not to see anyone other than Countess Tori and Missy.

Going into the small janitor's closet by the restrooms, I left the light out and pulled the door shut. There was the sound of approaching footsteps. While I expected the person to go into the locker room, they went into the men's restroom instead, so maybe it was a tenant.

They were in there for a long while, and as time passed I got really uncomfortable standing there in the closet. I started to lightly perspire and while earlier I didn't care if someone saw me all dressed up in girlie clothes, I now felt ashamed. There was no reason for this stranger to open the janitor closet, but I wished the door had a lock that I could slowly twist shut.

At long last I heard the muted flush of the toilet, and then heard the man go into the locker room. I thought I could just grab all my cleaning stuff and go down the hall, but I didn't know how long it would take that guy to get undressed.

The empty lockers have bathrobes in them. A client is required to be naked, but he is allowed to wear the robe when walking up to the play spaces on the top floor. It took this guy an agonizingly long time to get naked and into his robe. Finally I thought I heard the metal on metal sound of a locker door shutting. Not long after that I heard the locker room door open.

Knowing the man would be walking in bare feet and that I wouldn't hear him on the stairs, I waited in the dark for a few more minutes.

It took me several trips to get everything I needed down to the office. This office suite was the only one that had a small alcove with space for a little refrigerator and microwave, along with a sink, so at least I wouldn't be walking the hallway all morning filling and dumping my wash bucket at the big sink in the janitor's closet.

I felt like I had lost a lot of time, hiding in the closet and waiting on that client. I fought the urge to hurry into my work, and just started at a reasonable pace, trying to be thorough without rushing.

Working alone and in silence, dressed in women's clothing, is a very peaceful experience. My life can be hectic at times. Coming to work for Countess Tori is an escape from the real world. While painful at times and with its own unique stress, spending a day here in her building clears my mind.

Several hours passed and I made better progress than expected. The door to suite opened when I was wiping down the baseboards in a small private office.

"Sissy, report to me. Now!" I heard Missy command. Draping the wash rag on the edge of the bucket, I walked into the front office.

"Countess Tori has a no-show," she explained. "She'll give you a short session now. Let's get your frilly little ass upstairs."

Missy escorted me up to the top floor. There had been two apartments here originally, but they were now partially converted into play spaces.

I noticed right away that Countess Tori had changed into a tank top of black spandex and lace, which was probably more comfortable after a morning of sessions, but I didn't think looked as flattering on her.

A piece of bondage furniture which looked like an oversized padded sawhorse was in the middle of the main room, and I was told to take my position. I bent over one end of the horse, and while it was fitted with anchor points for binding a submissive in place, I was not tied or cuffed since I was not into bondage.

"We have time for a short session, sissy. We'll just get to it," Countess said. She then told Missy to bring her the ping pong paddle.

While Missy walked over to an open cabinet where an amazing collection of different paddles hung on display, Countess raised the back of my maid's dress and lowered my panties. I sensed that she was inspecting my buttocks to see if Missy's inspiration to do good work had been too severe.

"Missy, spank sissy with that paddle. Now be mindful to pace yourself."

"Yes, Countess Tori," Missy responded submissively, though I sensed a slight tone of delight that she would get to give me some swats, as opposed to just handing the Countess various paddles.

Now some hardcore player might consider the ping pong paddle to be too common or tame, but for me, in the hand of a skilled dominatrix, it hurts just right. Missy spanked me a bit harder than I would have liked, but I knew this would be a short session so I'd be able to endure it.

Missy had been swatting me on one cheek of my ass and then the other. Countess Tori told her that she should mix it up and not be so predictable, and then took the paddle away from her to demonstrate.

Countess Tori's swats were not just random as to where they landed, but also in number and intensity. I might get two light swats on the left cheek of my ass, followed by one stinging blow on both butt cheeks, followed by four light swats and a heavy one on the right. It was easy to get lost, my mind disconnected from everything but being spanked with her paddle.

She then lightly caressed my ass with the rubber face of the paddle in slow circles, explaining to Missy that not only would that allow a submissive some time to recover from the pain so they could endure a longer session, it would also give her a break so the session wouldn't be such an intense workout.

After another burst of random swats, Countess Tori ordered me to worship her boots. I knew this was another tactic that allowed a session to continue by taking a break in the physical activity, while at the same time allowing a submissive to enjoy their fetish for high heeled boots, and Countess Tori had such a delicious collection of boots.

The black leather was soft and warm under my tongue. When she ordered me to lick the heels she didn't raise a foot off the floor, so I had to lie down on my side behind her to slowly lick the tall stilettos from bottom to top. I knew Missy was standing close by, but Countess rarely had me lick her battered ankle boots.

"Missy, get another paddle," Countess ordered. I heard Missy walking over to the cabinet as I continued to worship the spike heels. "Not that one, it's too severe," Countess corrected, and I thought I heard Missy give a soft huff of disappointment.

After making a few more poor choices, Countess Tori walked over towards the cabinet, leaving me there on the floor. She took a paddle from a dejected Missy, some slender wooden thing with a single row of large round holes, and placed it back in the cabinet.

Countess then took out a small black paddle shaped like an old fashioned hair brush. From my vantage point I couldn't tell if it was made from leather or rubber. Countess Tori spun Missy around by the shoulder and swatted her exposed buttocks with two loud blows on each cheek of her ass.

I was thrilled to hear Missy gasp with pain after each swat, and I'm sure she felt humiliated being spanked in front of me. Then to my surprise, Countess Tori handed the paddle to Missy.

"Now remember. Random, and restrain yourself," Countess instructed. I was then ordered to get back in position on the padded horse.

The spanking that followed was certainly more random, but not very restrained. The light swats were few and even then a bit on the heavy side. I know I've been spanked with this paddle before, but didn't remember it hurting as badly.

Although I tried to keep myself calm and quiet, before long I found myself letting out brief low grunts each time the paddle landed on my bare bottom. I was then aware that I was becoming sexually aroused. My penis trying to swell within the confines of my chastity device. Something that hasn't happened during a session in a while.

"That's enough," called out Countess Tori. I was thankful that the spanking was over, at least for now. To my surprise, Countess told me to stand in the corner and face the wall.

"You need to learn to keep yourself under control, young lady," Countess scolded Missy as I pulled up my panties and then walked to a corner of the room. Missy mumbled some response that I couldn't hear. Perhaps it was a smartass remark, because Countess Tori ordered her to bend over the end of the horse. Missy huffed in protest and was soon crying out in pain as I heard the paddle firmly slapping her ass.

Knowing Countess Tori's back was towards me, I dared to look over my shoulder. Missy squirmed, the tips of her tall heels slightly lifting off the ground as she was firmly paddled. It was over quickly though and as soon as Countess stopped spanking Missy she turned around to look at me.

I was sure that she saw me quickly look away, and a bit concerned that I might face some real punishment. Instead she told me that she was going to order lunch from a place down the street.