Sissy and Missy

I listened at the wall, hoping to hear sounds of their intimate session in the next room, but was denied. For a while I pondered whether or not Countess Tori and Missy were lovers, or if part of Missy's duties involved pleasuring the Countess whenever she desired. They seemed to be an unlikely couple as the Countess was closer to my age. Eventually I lay down on my side on the bunk and got as comfortable as I could.

Not sure if I'd dozed off, the door to the room suddenly opened and a dejected looking Missy walked in. I couldn't see Countess Tori, who was standing outside the open door and told Missy to lock herself in the other cell. Missy obeyed, and tossed the key out to the Countess, who told us she would return soon and closed the door. I was still getting the deadly stare from Missy until she was certain the Countess had walked away from the door, and then she laid into me.

"You really fucked up, sissy," she said in an angry whisper. "You should have lied and said you forgot to do something like clean the bathrooms."

"Why would I do that for you?" I asked quietly.

"I'd make it worth your while, but now I'll make your life miserable. I know you're green lighted for anal training," Missy threatened. "First chance I get, I'm going to strap on the biggest dildo we have and make you squeal like a pig."

I had to stop and think if she would actually do that.

"You're an ugly girl, sissy. I'm the pretty one," she said, and that hurt. It might have been unwise to talk back to her, but at that point I didn't care.

"I hope that Countess Tori punishes us at the same time. She's going to beat your ass until you cry like a little girl, and I'll enjoy it," I told her. I thought I saw her eyes get a bit teary.

"You're a filthy old pervert," Missy responded, and then reached under her bunk for a bottle of water.

"I'll bet there was no orgasm for you. Just denial," I taunted. "Finish where you left off and then locked up with me to wait for your punishment." She mumbled something that I couldn't understand, so I told her, "You dress like a stripper, not a dominatrix."

"I have to wear what I'm told, but I'm close to earning my knee high boots, and when I do," Missy's words were cut off as the door to the room opened and Countess Tori walked in slowly. We both looked at the floor and Countess stopped in the middle of the aisle.

She had put on another pair of thigh high boots, this one of what looked like soft black leather, heels probably four inches high, and Countess had also put her spandex pants back on. I didn't dare raise my eyes any higher as she stood there with hands on her hips. Countess Tori stood there for a long and painfully silent time. Who knows how long she had been listening at the door.

"I'm surprised to see the two of you in here," Countess said sarcastically. "I thought I heard two little children squabbling. Do I need to go over the rules again about you two speaking to one another?" Her voice now raised, and I assume the question was rhetorical so I remained silent. "If it doesn't pertain to work or a session, keep your mouth shut!"

I heard Missy give a few light sniffs, and thought she might burst out crying. I knew we were both going to be punished, and while I wasn't looking forward to that, I also feared that I might be banished afterwards. This had been a nice arrangement and I might have blown it. Exchanging trash talk with Missy had been a bad move on my part. Disrespectful, but I suppose that since we had both been locked up in the jail it felt at the time we were equals.

Countess Tori turned towards Missy's cell and I heard her unlocking the door. Then my cell was unlocked and Countess grabbed each of us by the ear and led us across the hallway to the school room.

The school room was like another stage set used for domination sessions. There were only two old fashioned school desks, one on either side of the door as you walked in, and a teacher's desk at the front where a blackboard was on the wall. In one front corner of the room was a tall wooden stool, and resting upon it was a high cone shaped hat with the word Dunce written on it in bold lettering.

Countess marched us to the front of the classroom. Someone recently had the punishment of writing, 'I will not masturbate with porn', on the blackboard many times, and for just a moment I thought that was funny.

Missy was put into position first, bent over one end of the teacher's desk, and then I was dragged around by the ear to bend over the opposite end. We were told not to look at each other so I looked down at the desktop.

I already knew what was on the desk from walking up to it. A long heavy wooden paddle with rows of large holes drilled in it, along with a slim bamboo rod.

My personal favorite domination fantasy is to be spanked with multiple paddles. Starting with softer ones, mild swats with the pain enough to be real but not so hard that I can't endure a lengthy session. The drilled wooden paddle on the teacher's desk might be the last type of paddle used, and I would only be given a few swats. However, I was about to be punished, and that is different.

For punishments, Countess Tori liked to inflict the maximum amount of pain in the shortest time possible. While the safe word could be used, she had stressed before that it was best for a person in my position to endure a severe punishment.

I had never been caned before, and that bamboo rod would certainly give maximum pain for minimal effort by the Countess. She slid the paddle off the desk and walked behind me, then ordered me to drop my panties and lift up my dress.

Doing as I was told, I expected a hard swat to immediately follow. Instead, she lightly probed with her fingers at the welts left by Missy's crop on the backs of my thighs. I flinched involuntarily. Missy's tall heels scraped lightly on the tile floor as she fidgeted while her work was being inspected.

"A bit overzealous," Countess Tori said quietly. There was a catch in Missy's breathing.

Then three powerful swats boomed across my bare ass. I groaned loudly with each one. Countess Tori's heels clicked on the floor as she walked around the desk. Missy was breathing heavily with anxiety before her punishment even began.

I heard the clicking of a small metal clip, and then Missy's little riding crop was tossed onto the desk.

"You can have that back when you learn to be a bit more responsible," Countess told her. Missy also received three heavy swats, and to my surprise, only let out a yelp of pain on the last one.

While I love the sound of high heels on hard floors, during a time like this it really built the tension as Countess circled the desk to give me the next round of swats. It was another salvo of three, they felt harder than the first time, and she paused for a few seconds between swats just to let them sink in. I grunted with pain each time and my eyes were tearing up.

Looking down at the desktop, I saw a few teardrops had fallen from Missy's eyes. She was quietly sobbing, but as Countess Tori walked slowly over to her, Missy began to cry out loud. Countess Tori administered three heavy swats in slow succession, and Missy howled as each one landed.

It had been a number of weeks ago when I'd seen Missy punished, and I had thought she was a bit of a drama queen. However, being this close to her when she was paddled, it was clear that she had a low tolerance for pain. It was somewhat surprising to me that Countess didn't show her assistant and possible love interest any preferential treatment when it came to punishments.

After taking my next swat, my tears were also flowing, though I cried in silence, only grunting loudly when the paddle smacked my ass squarely the next two times.

As Countess walked back over to Missy, I could hear the tall heels of her ankle boots clattering on the floor as she sobbed and squirmed uncontrollably. While I will admit I got some satisfaction out of seeing Missy take a punishment, I was almost to the point of feeling bad for her. The first swat left her mumbling something I couldn't understand.

"Mercy, Countess!" Missy called out after her second swat. That was the safe word, and her paddling stopped. Countess Tori set the paddle down on the desk, then took Missy by the ear and led her around behind me. At first I thought in horror that she might let Missy give me a few swats, but then I heard the legs of the dunce stool momentarily scrape on the floor, and it seemed that Missy would have to sit in the corner as my punishment continued.

"I'm not finished with you, Missy," Countess warned her.

I gasped in pain at the next few heavy swats and then realized I would get no break since Missy was no longer being paddled. Did Countess intend to use the cane on me after this painful spanking? While I tried to cry in silence, I couldn't hold it back any more. Losing count of the swats, crying freely, I just tried to endure my punishment. Eventually Countess told me I was free to go.

After pulling my panties up I headed for the door as quickly as I dared. Before leaving I took a quick look back into the school room. Countess Tori's back was turned as she arranged the paddle back on the desk. Missy was uncomfortably seated on the stool in the corner, the tall dunce hat balanced on her head. Her makeup was streaked from her tears, and she gave me a lethal stare.

My own makeup was in just as bad of shape but I washed it off in the second floor ladies restroom. I changed clothes and left the building, walking slowly and uncomfortably to my car. I would most likely be back in a few weeks to serve Countess Tori, and having taken my punishment that arrangement would continue as normal. Whether or not Missy would hold some sort of grudge and what she might do to me behind the Countess's back was unknown, and that anxiety lingered in the following days.

The End