Sissy and Missy

Copyright 2019 Christopher D.B.

*

The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week.

My feet were hurting, as the toe box on my pumps fit a little snug. I'd hoped they would stretch out just a smidge after wearing them a few times but it didn't seem that would happen. They also fit a little loose in the back, though I'd been able to partially fix that with moleskin strips. I was determined to master walking in four inch stiletto heels, but I think I was going to have to invest more money in a quality pair that fit right, as opposed to the low end costume variety.

The pink satin French Maid outfit that I wore was also a cheap costume. It seemed that each time I washed it I had to make minor repairs. Good thing I was handy with needle and thread, though if I continued to serve Countess through the end of the year, I was going to have to find another outfit of better quality.

Before leaving the apartment, I checked my makeup in a bathroom mirror. Missy was supposed to be teaching me how to do makeup, but she always insisted on doing a few final touch-ups, which resulted in me looking like a cheap whore of a drag queen. I was always concerned about the heavy makeup smearing or running when I worked up a sweat doing housekeeping, but it looked presentable.

Leaving the apartment, I made my way up the stairwell. My heels echoed loudly on the old marble treads. The stairs had an ornate iron railing, and there was a peaked skylight of wire reinforced glass above the stairs on the fourth floor.

This top floor of the building had been two apartments, but was now partially converted into Countess Tori's play space. She did female domination sessions for hire, and I was getting a deeply discounted rate by working as her sissy maid every other Saturday.

As I let myself into the main room, Countess Tori was seated on her elaborate throne as expected. Her blonde hair was long, thin, and straight. She wore her black leather biker jacket with the diagonal front zipper open enough to show off the cleavage of her large breasts. Missy was kneeling to her side, looking at her fingernails, as the two chatted like good friends about a nail salon here in the historic downtown area.

"Are you finished with your vacuuming, sissy?" Countess Tori asked.

"Yes, Countess," I replied softly, avoiding eye contact and looking at her boots instead. They were made of red and black leather, thigh high, with long laces that wound through a seemingly infinite number of small shiny hooks all the way up the front of the boot shafts.

"I'll allow you to worship my boots before your next assignment," she said, and I quietly thanked her as I slowly approached her throne and then knelt before her.

Countess Tori was a heavy set woman, though the boots fit her thick legs perfectly. I'll admit that I look up fetish boots and shoes all the time online and I had never seen a pair like these. I suspected they were custom made, and very expensive. Up close I noticed they had no zippers up the inside of the shaft for easy on and off, like so many front laced boots do. That would be no inconvenience for Countess, who probably always had a submissive at her disposal to handle the long boot laces.

Taking my time, I slowly licked the pointed toes of her boots, and then gently sucked on the spiked heels, which may have been about five inches high. The two ladies continued their conversation, ignoring my presence.

I had only been serving Countess Tori for a few months and hadn't quite figured out their relationship. Missy appeared to be both a submissive personal assistant and dominatrix in training. Early on, all I was told was that I must obey Missy, though she was carefully supervised.

The few times Missy was ordered to give me a spanking or flogging, she did so with a bit more enthusiasm than I liked. However, Missy was not immune to being punished by Countess Tori, and I'll admit I was delighted the one time I'd seen her get paddled.

I was slowly working my way up the shafts of Countess Tori's thigh high boots, lingering at the knees, where the laces were stretched taught. She wore some tight black spandex pants that disappeared inside the tops of her boots.

"You've enjoyed yourself long enough," Countess said, pushing me away. "Missy will take you down to vacuum the second floor." Turning to Missy she instructed, "Give him some incentive to do a good job while you're down there, and assign a few more tasks to keep him busy."

"Yes, Countess," Missy replied quietly, and we both stood up to leave the room.

"You're wobbling in your heels, sissy," Countess told me. "I think you've had enough of your big girl shoes for the day. Missy will see that you put on your flats while you are down there."

"Yes, Countess," I answered. Although my feet hurt I was a bit disappointed that I'd been ordered to take my high heels off. Demoted to flats for the rest of the day. As I followed Missy out to the hallway, Countess called after us,

"Don't take too long, Missy. I need you back up here as soon as you get him situated."

Missy was wearing some black patent leather ankle boots that laced up the front. The heels were easily six inches tall, maybe more, with thick platforms. Of course she could walk effortlessly in them, and our high heels clattered loudly on the stairs as we made our way down.

Following behind Missy, I had a great view of her sexy ass. She always dressed in skimpy, revealing outfits. Today Missy wore a shiny black PVC teddy, cut high at the hips with a thong back, which left her perfectly round cheeks exposed. As she turned on the first landing I got a quick view of her small breasts, as the teddy's neckline plunged below them, forming into an open front shelf type of bra. Although I thought her outfit might be more appropriate for a stripper, Missy wore a law enforcement style utility belt around her waist, leaving no doubt that she had a position of authority.

The belt was wide, black leather, with two rows of large chrome grommets. A stubby leather riding crop hung from the belt at her right side, and a small round rubber paddle hung at the left. Of course she had a pair of shiny handcuffs worn on the belt above one hip, and there were several leather snap pouches, though I had no idea what she carried in those.

In what I assumed was her mid twenties, Missy was a few decades younger than me. She was pretty, in a stern sort of way, but I thought had the capability to be even hotter if she let her short dark hair grow out, removed some of her piercings, and didn't get any more tattoos.

"Get your hose, sissy," she ordered as we stopped at the third floor for me to retrieve the vacuum. She always put a heavy condescending tone on the word, sissy. The long vacuum hose was cumbersome to deal with. "I hope you enjoy fondling that, since your junk is locked up," she taunted.

Missy was referring to the chastity device that I was required to wear while serving as Countess's sissy maid. I wasn't permitted to masturbate while on the job, and since I was often working out of sight, she said it was a necessary precaution.

"Let's go, sissy! Move it!" Missy ordered like a drill sergeant as I tried to get the long central vac hose quickly wound up in my arms, along with the chrome wand. She unclipped the riding crop from her belt and whacked it a few times on the iron stair rail. "Chop, chop, sissy! I don't have all day!"

I followed Missy down to the second floor and was able to drop the tangled mess of vacuum hose in the long hallway by one of the wall connections. I had only paused a moment, but Missy impatiently pointed down towards the back of the hallway with her riding crop.

"No big girl shoes for you, sissy. Now let's go take those off. I know you're disappointed. Are you going to cry?" I didn't answer her, but headed 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.

I fumbled with my combination lock while Missy periodically slapped her riding crop on the door of an adjacent locker. This room was where I changed into my sissy maid outfit and did my makeup. It was also where men who came to Countess Tori for sessions would disrobe and lock up their clothes. There were no locks on the other lockers, and no waiting clients at this time, so I assumed Missy got to change clothes upstairs, a privilege of her position.

Slipping off my pink pumps, I retrieved a pair of silver metallic flats from my gym bag.

"Oh, those are so pretty," Missy said flatly. "I'm sure you feel really sexy when you wear those."

I didn't respond. We really weren't supposed to have any small talk between us. After slipping on my flats, I closed my locker and started to leave the room.

"Not so fast, sissy," she said, moving to block the door. "You need some incentive to do a good job." Pointing her riding crop at me she ordered me to turn around and drop my panties.

Missy was all too eager to whip my ass. If I delayed it and Countess came downstairs to see what was taking so long, I'd be in real trouble. I turned around to face the metal folding chair, pulled my panties down to my ankles, and bent over, placing my hands on the cool seat of the chair.

"Such pretty panties. Are those special, made for a man, to accommodate your junk?" she asked, sounding serious for once.

After a bit of hesitation, I told her they were. While I didn't elaborate, I will tell you that they were one of the few items of my limited sissy maid wardrobe that I had actually spent money on. They were a nice comfortable fit, even when I was wearing the chastity device on my penis.

"It's all about feeling pretty and sexy, right? You men that like to dress up, it's just about the clothes, not wanting to be a girl, right?" she asked a serious question again.

"Yes, it makes me feel sexy, even if you think I look foolish. It's an escape from reality," I told her.

"That's what countess says you dresser guys do. I just wanted to hear it from you," she said as she lifted the back of my maid's dress, exposing my bare bottom.

Her riding crop gave a sharp snap on the back of one thigh, just below the cheek of my ass. I couldn't help gasping in pain. There was another quick snap of the crop in the same place on the back of my other thigh.

That was how it went, alternating from the back of one thigh to the other, right below my ass. I didn't bother to count the strokes, I was too busy trying to keep still and not cry out. Thankfully her so-called incentive was over quickly. She ordered me to pull up my panties.

"Now get on your knees and lick my boots," Missy ordered.

As I gave her boots a quick once over with my tongue, I could feel the deep burning in the backs of my thighs. She had been strategic in her whipping, and I knew it would be uncomfortable to sit down for the rest of the day, and maybe the next.

"Take your time, you little sissy bitch," Missy scolded. Savor them like you do Countess Tori's boots.

Her patent ankle boots had a lot of scuffs, and the shiny finish was cracked in several places. I tried to remember if I'd seen her wear any other boots before, but thought this might be her only pair. I knew Missy really couldn't see what I was doing, standing over me like she was, but I lovingly licked her beat up fetish boots just like she told me to do.

Perhaps Missy realized she had gotten carried away, dominating me for this long, as she suddenly turned away and told me to get to work, before slamming the locker room door behind her. It was then that I realized Missy didn't give me any other work assignments to do, but I wasn't going to call her back, and waited until I heard her clacking up the stairs to the fourth floor where an impatient Countess might be waiting for her.

Walking down the hallway towards the tangled pile of vacuum hose, I could feel the backs of my thighs burning even more. If there was any consolation, my flats felt so comfortable on my feet, and I'd always had a fetish for metallic clothes and shoes, so I really liked this pair even if they didn't have high heels.

There is a central vacuum port in the front portion of the hallway, where I connected the hose. Several other ports were located in offices on this floor.

The first floor had two rental spaces with street access, and they were both occupied with trendy little boutique shops, which are popular in the historic district and I never had to do anything 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.

On the second floor, where I vacuumed a bit slower than normal thanks to Missy's vicious incentive, there were a number of rental offices. Some were single rooms, and others were suites of several rooms. 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 kept weird hours, and I'd heard what sounded like an old manual adding machine rattling away in there at times. I wasn't responsible for cleaning their spaces.

Countess Tori had owned the building for several years, and kept the vacant offices spotless so they could be shown to prospective tenants at any time. In the event that I encountered anyone in the hallway or on the stairs, I was instructed to ignore them and go about my business. I assumed the engineer and accountant knew what sort of kinky things the Countess did upstairs, and didn't care, and for that matter might even be clients.

It was peaceful working on the second floor. There had been times in the past when Missy would be sent to check on my progress, and usually torment me some for her own amusement, but I felt I could relax for a while.

Since I had pretty decent access to the building and often worked alone you might think it would be easy to get the spare key for my chastity device out of my locker so I could quickly jerk off somewhere. I'll admit I was usually under some sexual tension, as I was constantly exposed to most of my sexual fetishes like high heels, leather, and cross dressing. I also like to be dominated by women, and spanked or whipped to some degree.

That said, I had been warned by Countess Tori when I first began working for her, that if I was ever caught masturbating without permission, I would be banished. It had taken me such a long time to find a good professional dominatrix that I wasn't going to risk ruining our arrangement any time soon. Best to keep myself locked up.

When I finished and had stowed the vacuum in the closet by the small restrooms, I made my way up to the fourth floor for my next assignment. My silver flats padded softly up the stairs, and the backs of my thighs burned a bit more as I reached the top floor.

Walking into the main room, I saw it was empty. They might be downstairs in the apartment, or across the hall in the other suite of rooms that was partially under construction. Then I thought I heard something in the next room, which was set up as a small lounge, and quietly went to check it out.

At first I couldn't believe what I saw. Countess Tori lay naked on the chaise lounge, her eyes closed and open mouth moaning softly. Missy, still wearing her scanty pvc number and ankle boots, knelt beside the lounger and had her face buried between Countess Tori's legs.

I'd seen plenty of girl on girl scenes in porno, but never seen it happen in real life. They were relaxed and completely lost in their moment. Countess Tori's breasts were enormous, and though they sagged heavily to the sides they were spectacular. As a submissive I had never been allowed to see them. My penis tried to swell within the confines of the chastity device.

As if it would stop my body's natural reflex to get an erection, I glanced around the room. Countess Tori's boots lay open on the floor beside Missy, along with her spandex pants. These items looked as though they had been hastily removed in a moment of passion. My penis ached as it tried to get hard, and I tried to somehow consciously subdue it.

I watched in agony until Countess Tori began breathing in a quick rhythmic pattern, her orgasm getting near. Then I realized I had been standing there for much too long. As I started to ease back out of the doorway, my flats moving silently on the hardwood floor, one plank gave a faint squeak.

The Countess opened her eyes widely and briefly screamed as she tried to cover her breasts from view. Missy, her lips glistening, looked over her shoulder and saw me easing away from the door, but then I froze in my tracks.

"You're supposed to be working!" Countess Tori scolded, as she reached for any item of clothing to cover herself. I covered my eyes with my hands.

"I finished vacuuming and came up here for more work, Countess Tori. I just got here," I added hastily. She probably knew I was lying.

"Didn't Missy give you some other chores?" she demanded to know. Peeping through my fingers at Missy's face, I saw a look that was a strange blend of fear and anger.

"She didn't give me any other work, Countess," I had to answer honestly. There was the sound of shuffling clothing. Countess asked Missy if what I said was true. Missy was silent for an awkward moment, and then tried to stammer a reply but Countess Tori cut her off.

"Put him in a jail cell, Missy." Countess told her. "I will punish both of you later."

Missy got up, and when her face was turned away from Countess Tori, she gave me a killing stare. She grabbed one of my hands and pulled me out of the lounge. My destination was in another room next door.

It was one of the smaller rooms in this suite, and had been fitted with a jail cell on either side of a narrow passage.

"Way to go, dumbass. Watching us like that," she whispered to me. "She's going to beat the shit out of us." Missy slammed the metal bars shut and snapped the padlock, then walked out of the room and closed the door. I heard the sound of her high heeled boots tapering off as she returned to the lounge, presumably to continue pleasuring Countess Tori.

I had caught brief glimpses of the jail room before, but this was the first time I'd been in here. You might say it was more like a stage set than an actual prison. The cell door with the metal bars and horizontal opening to pass in a tray of food was authentic enough. However, the rest of the bars across the front of the cell, upon closer inspection, were made of wooden dowel rods painted to match the cell door.

There was no way a prisoner could slip out for some reason without damaging the wood bars, but if there was some emergency like a fire, escape would be easy enough.

As you might expect, there was a narrow cot with a thin mattress on it. I tried to sit down there but it hurt the backs of my upper thighs. Adjusting my position, sitting right on the edge of the cot, was about as comfortable as I could manage. Missy was probably licking Countess Tori's pussy right now, but it would likely take the Countess a while to get back in the right frame of mind for an orgasm. Who knows how long I might be locked in here.

There was a five gallon plastic bucket with a lid at the foot of the bunk. A roll of toilet paper was on the lid of the bucket, indicating the intended function. Looking across the aisle at the other cell which was furnished like mine, I saw that under its cot were a box of granola bars and some bottles of water. I found my cell stocked with the same provisions and opened a bottle of water.