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Sissy and Missy II

"A sissy maid plots revenge against a dominatrix in training."

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Author's Notes

"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 here at Lush Stories."

Copyright 2020 Christopher D.B.

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's 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 perfectly.  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 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 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 the 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 washrag 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 that 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 hairbrush.  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.

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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.

“Missy, show him the menu and take his order,” Countess Tori said.

Missy picked up a well-worn takeout menu from over by the laptop computer and rudely thrust it into my hand.

It was a sandwich shop, not part of a chain, I had seen it a few blocks down the street when coming and going from the building, but had never eaten there.

Although there was a low padded stool by the small computer table, Missy opted not to sit down.  Her bright red freshly spanked ass looked incredibly hot as she logged into what I assumed was the sandwich place’s website.

I told Missy that I wanted a Philly steak hoagie with fries.

“Their onion rings are the best.  You should get those instead,” she told me.

“I want the fries,” I insisted.

“Sissy, I’m telling you, you really should get the onion rings,” Missy persisted.

“I want the fries,” I repeated with more emphasis.

“Now you two quit arguing or I’ll give you both a firm caning,” Countess interrupted.  “Missy, order the fries.  Sissy, get back to work.”

Not long after that I was wiping down the cabinets in the little break area alcove when I heard the door to the office suite open.  It was Missy, though at first, I didn’t recognize her because she was fully clothed.  Faded jeans, a sweatshirt with the name of a local community college on the front, and gym shoes.

“I’m going to pick up the sandwiches,” she explained.  “But first I’m going to whip your ass!”  Around her waist was a wide black leather belt, which she began to unbuckle.  “Take off your stupid girlie dress!” she commanded.  I just stood there, unable to move, I was surprised, and also afraid.

She turned me around and roughly unzipped the back of my French maid uniform.

“I said, take it off.  And take off those stupid panties,” she snarled.  “You got me in trouble with Countess last time you were here.  I was about to earn my knee-high boots.  She took my crop, you sissy bitch!”

My uniform, apron, and panties were in a heap around my ankles, and I was trembling.  Missy pushed me down over the counter and started whipping my ass with her belt.

I had never been whipped with a belt in my life, though as a kid I’d had friends that occasionally faced that punishment and feared it.  The pain was far worse than her little riding crop, and I didn’t just feel the pain, I also felt her anger.

The whipping probably didn’t last as long as it seemed, but I found myself sobbing, and then begging for mercy.  Mercy was supposed to be the safe word.

Missy did stop whipping me, but then pulled me by one ear over towards the window.  My eyes were still blurry with tears and I wasn’t sure what she was going to do.  Then she pulled her handcuffs out of a pocket of her jeans and secured me to the radiator below the window.

“You’re not going to run upstairs and snitch to Countess while I’m gone,” she said.  Then Missy turned to leave, threading her belt back through the loops on her jeans as she walked out of the office.

My body was still shaking, and tears were still flowing.  I knelt on the floor by the radiator, naked except for my chastity device, and my lacy pink bra, the padded breast forms now soaked in sweat.  I was only wearing one of my silver flats.  The other shoe had slipped off when I had been forced to step out of my girl clothes.

Looking at the handcuffs, they looked like real police issue.  Not the sex toy variety with the safety release latches.  The room was cool and I wished I had something to cover myself with.  I felt very ashamed of getting myself into this situation and started crying again.

Time passed very slowly.  I hoped that for some reason Countess might come down to check my work and find out that Missy had whipped me, but it didn’t happen.  Eventually Missy returned with several large paper sacks containing the lunch.  She left my food and drink on the counter in the alcove, then pulled the key to the handcuffs from a pocket of her jeans.

“Now you’ve been crying like a little girl and ruined your makeup.  You need to fix that right away before eating your lunch.  Don’t you think of snitching to Countess,” she warned.  “Just consider yourself lucky that I didn’t leave you cuffed to that radiator with a big butt plug up your ass.”  Then Missy left the office.

Putting on my maid’s uniform, I saw that my quick repair from early this morning had been ripped loose.  I was pretty sure I might cry again and really didn’t want to fix my makeup yet.  However, another client would probably come in just a little while, so this was the time to get my makeup bag from my locker.

I did my makeup in the small women’s restroom on the second floor.  There is a little shelf by the sink in there to set my bag on, and the jar of cold cream.  Looking at myself in the mirror, my pink ruffled maid’s uniform, the old pale pink tiles on the wall of the ladies' restroom, I felt foolish.  I had really enjoyed cross-dressing but Missy had made me feel guilty about it.  Somehow ruined it for me, at least for the day.  That little bitch!

When I returned to the office suite and took my lunch from the paper sack, I saw that instead of the fries I had asked for, Missy had gotten me the onion rings.  They turned out to be really good, but as I finished my lunch, I vowed to somehow take my own revenge against Missy.  As I resumed cleaning, a plan came together.

I waited until I heard the next client come in the door and up the stairs, and then head up to the top floor after changing in the locker room.  Then I waited about ten more minutes to be certain a session would be underway.

In the locker room, I opened the window and looked into the narrow alley below.  Missy’s cigarette butt had to be on the pavement down there, but I didn’t see it.  Maybe she had given it a good flick with her fingers instead of dropping it.  Still, it would be down there, and I was going to retrieve it.

Now I thought about removing my makeup and changing into my normal clothes.  Going out the front door but leaving it slightly propped open with something, but that would take too long.  Going out the front door in my maid’s uniform might attract unwanted attention so that was also not an option.

At the back end of the hallway is a large window with a few short steps up to the sill, and outside is a metal fire escape anchored to the side of the building.  The window opened easily and I looked at the small parking area below.  My old Mercedes was down there, along with a few other vehicles, but all were unoccupied.  No one from the shops on the first floor took a smoke break out the back door.  The surrounding buildings, their back windows were blank, vacant, or closed for the weekend.

I momentarily went back to the janitor’s closet.  Hanging on the wall, coiled up, was a thick bright orange extension cord.  Slinging it over my shoulder, I went out onto the fire escape.

The thin soles of my silver metallic flats felt a little uncertain on the metal grating of the fire escape.  From the metal landing outside the window, I descended a short flight of steps to a second landing.  Here there was a stairway that went down to the ground, but it was raised and would hinge down as you walked upon it.  I had never used one of these before and only seen them operated in movies and TV shows.

I took my first cautious steps out onto the tilted stair treads.  The fire escape stair began to swing down slowly, and with surprisingly little sound despite the heavy rust.  I paused on the bottom step.

Shrugging the heavy extension cord off my shoulder, I uncoiled it and started to tie one end of it to the base of the railing.  Knowing the stairway had a counterweight and would swing back up once I got off, I would be stuck outside the building.  Having a rope to pull the stair back down would have been perfect, but since I had none I thought I could improvise with the extension cord.

The thick wire was difficult to tie and really couldn’t be pulled into a snug knot.  I retied it in a sloppy double knot.  Stepping off the bottom stair, I let the cord slide through my hands as the stairway raised up off the ground.  I wasn’t sure how long the extension cord was and was afraid it might slip out of my hands and end up dangling just out of reach.  That didn’t happen though.  The end of the extension cord hung about six feet off the ground.

Feeling I had taken a lot of time rigging the fire escape, I went right into the alley, only then thinking that I should have peeked around the corner of the building first.  It didn’t matter.  No one was there.  While cars passed on the street, it was unlikely that I would be seen.

Standing below the locker room window, I began my search for Missy’s cigarette butt.  There were a few butts on the ground here, however, all of them were weathered, and none were smeared with Missy’s lipstick.

The search seemed to take forever, but at last, I found a fresh cigarette butt, clearly imprinted with Missy’s distinctive reddish-black lipstick.  It had somehow bounced and landed partially hidden behind a downspout on the building across the alley.  Carefully picking it up, I went back to the fire escape.

My knot held firmly as I pulled down the metal stairs as planned.  I got back inside the second-floor window and returned the extension cord without incident.  Thinking that I had taken too long, I left the cigarette butt on a high shelf in the janitor’s closet and went back to my chores.

I waited until the next client was upstairs and some time passed to make sure his session had begun.  With Missy’s cigarette butt in hand, I went up the stairs as silently as I could to the third floor.  The door of the landing was locked as expected, but I knew that a key was hidden under a potted plastic plant off to one side.

Countess Tori has a spacious apartment that occupies the entire third floor.  It’s fully furnished and has some of her personal items, but I know she only stays here a few nights a week.  I usually dust and vacuum in here on days that I serve the Countess.

I went to her bedroom at the back of the apartment.  It has a private bathroom with a small window.  I opened that window a few inches and placed Missy’s cigarette butt on the sill in clear view.

Sure that smoking was not allowed in the building, if Missy had been caught in the client’s locker room, I doubt that her punishment would be severe.  However, I doubted that Missy would even be allowed to use Countess Tori’s private bathroom, so smoking in there would be a serious offense.  It was a shame that I would likely not be around to witness Missy being punished.  I locked the apartment and returned to my office cleaning.

There might have been only an hour left before I would be dismissed, and as that time went by I thought of holes in my plan to get Missy in trouble.  I had been so obsessed in my planning of how to get in and out of the building undetected, that I gave little thought to how credible my frame-up job for Missy would appear to Countess Tori.

Even if Missy had a smoke in the Countess’s private bathroom, she wouldn’t be so careless as to not flush her cigarette butt down the toilet or flick it out the window.  Countess Tori would have to know I was trying to set Missy up, and who knows what effect that would have on me.

Unless Missy had smoked in Countess Tori’s private bathroom sometime today, once confronted by the Countess, it would be obvious to Missy that I had tried to frame her.  She would be all too delighted to whip my ass again.

I was seriously contemplating slipping back up to the apartment and knocking that cigarette butt out the window, but then both Countess Tori and Missy walked into the office.  Although I’m sure I visibly jumped, Countess calmly told me to continue my vacuuming while she inspected the suite of offices.

Missy just stood by the door to the hallway with a menacing look on her face.  Were sessions over for the day and both of them had made a stop in the apartment already?  I tried to remain calm but felt my level of anxiety rising.

Countess Tori came back into the room and made a slow inspection.  At last, she said that my work was satisfactory and that I was to follow them upstairs to help Missy straighten up the play space.

The Countess walked slowly up the stairs.  Thinking that my plan to frame Missy may have been busted and I might be walking into some punishment session, the slow pace was agonizing.  Countess was in the lead, of course, followed by Missy, and I brought up the rear.

Countess Tori was wearing a different pair of thigh-high boots now.  Black leather with elaborate stitching in dark blue swirls all the way up the tall shafts.  I also noticed that Missy’s ass, bare except for the narrow strip of shiny black PVC wedged between her butt cheeks, had a few small red welts on it, as if she had taken a few licks from Countess Tori’s riding crop.  Not enough evidence of a serious punishment session.

It was then that I realized that if Countess intended to punish me, she would likely discover some welts on my ass, still visible after the whipping that Missy had given me earlier in the day.  There was some comfort in that, thinking I might get an opportunity to explain my motive for revenge and plead for forgiveness, or at least leniency.

Countess led us to a large open area on the top floor.  It had been partially under construction for as long as I had worked for her, and it served as sort of a general-purpose dungeon.  There were a few pieces of bondage furniture and a number of whips and paddles hanging on the wall.

An antique chair, refinished in glossy red vinyl padding and metallic silver paint served as a throne on a low raised platform in one corner of the room.  A number of pairs of high-heeled boots and shoes were scattered around the base of the throne, whips and paddles seemed to be lying around at random.  The last session here had been something intense, possibly with more than one submissive.

“Missy will put away the footwear and equipment,” Countess Tori explained.  “Sissy, you will sweep the floor and wipe down the furniture.”

“Yes, Countess,” we both answered quietly.  Countess Tori then walked out of the room.

Missy gave me an ice-cold glance, then went over to the throne and began to pick up shoes and boots.  They went on some open shelves off to one side.

The floor in this room is of wide wooden planks in desperate need of refinishing.  Although the floor looked clean, the cracks and crevices always held grit and dust, so sweeping always took a bit more effort than expected.

The two of us worked in silence.  I had expected Missy to make some sort of whispered threats or trash talk, but instead, she would periodically cast quick glances at the open doorway to the hallway, as if she thought Countess Tori might be listening to make sure we were working and not chatting.

When Missy finished her work, she knelt in front of the empty throne.  I was done a short time later.  Though I wasn’t sure what to do next, kneeling beside Missy seemed like the right thing to do.

“We’re finished, Countess Tori,” Missy called out.

Countess Tori quickly appeared all too quickly.  She must have been standing just around the corner hoping to bust us for talking.

Her high-heeled boots sounded wonderful as she walked across the wooden floor, and then took her seat on the throne.

“Worship my boots, children,” she ordered.

I was all too happy to worship her boots, and I could feel the swirled stitches with my tongue as I gave the shaft long slow licks.  It was odd to be literally rubbing shoulders with Missy as she worshiped the other boot.

Missy had a different boot worshiping technique, a quick series of light pecking kisses.  It made me wonder if Countess Tori preferred that and maybe I should use that fashion in the near future.

“Sissy, you are dismissed for the day,” Countess said.

“Thank you, Countess Tori,” I replied softly, and I got up to leave.  When I left the room, Missy was still worshiping her thigh-high boots.

Descending the stairs, I remembered what I thought were all the flaws in my plan to frame Missy for smoking.  I paused on the third-floor landing and looked at the potted plastic plant where the key to the apartment was hidden.

Perhaps I could enter quickly and snatch that cigarette butt off the window sill.  However, if Countess Tori came down the stairs and caught me in her apartment, I’d be screwed.  Of course, I could slip out onto her fire escape and get down to the second floor that way, though I was pretty sure I had locked the escape window on the second floor.

Should I go for it, or just leave my original plan in motion?  As I stood on the landing, my mind racing, I knew I was losing valuable time.

-To be continued-

Published 
Written by ChristopherDB
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