Cassandra's Summer School

Continued from: The Receptionist

By Tuesday morning, Cassandra showed up for her shift as usual, on-time and dressed professionally. I noticed her sitting a little more delicately but she had a new-found hop in her step, she was happy and looked energized. 

"Mistress, I took the liberty of laying out your "woodshed" outfit for you. This morning you have Lauren booked. She indicated in her online form that she needs "Daddy's" belt.  

I didn't worry about Lauren for the time being. I pulled Cassandra in for a hug. I was happy to see her looking so content and not upset anymore. 

I squeezed her tightly and spoke. 

"I'm sorry I had to punish you Cassandra. I hope I never have to do that again".

"Don't be sorry Ma'am, you helped me immensely. You truly did! It was like being plunged into an ice bath, yet my heart and my soul remained warm". 

Her eyes welled up a bit. 

"You gave me exactly what was missing in my life Ma'am, thank you again! I even went home last night, after my spanking, and apologized to my parents. I put them through hell last year", Cassandra explained. 

"Well I'm proud of you Cassie! For knowing and admitting what you need, even if it hurts a little". I softly told her. 

She then placed her hands on the seat of her skirt and rubbed. 

"I'll say! I had to sleep on my tummy last night Mistress", She whined. 

 As she continued to rub I could see her face blush deeply. I could tell she wanted to say something. 

"What is it Cassie?" I urged her to open up. 

"Ummm....the spanking was horribly humiliating and painful Ma'am. I hated ever second of it, in the moment... 

But later, when I was home in my room, is it normal to feel....ahhhmmm". She hesitated and was stammering over her words. I think I knew what she wanted to say. 

"Like later on Ma'am. when I was forced to sleep on my stomach in my bed, I ended up...."

"Oh...Mistress, your first client is here. You better go disappear into your office while I prep her". 

"Ok sweetie". I said, as I snuck off into my office to wait. 

Cassandra prepared and displayed Lauren, and took her seat at the desk to give Lauren some humiliating, exposure time. 

I gave them about 15 minutes together, in silence, before I made my grand entrance. 

"There's my naughty little girl!" I declared out loud, while wielding a black, leather strap. 

"I understand Daddy needs to march you out to the woodshed again Lauren, for a good belt-whoopin'?" 

The poor thing was bawling from her eyes and drooling from her gag, all while trying to say "yes Daddy" through her ballgag. 

Ohhhh the things people pay me for...

After Lauren's session had finished, Cassandra and I sat to talk about the session and how it went, yet I took things back to before the session. 

"Cassie, huni. When Lauren arrived you were about to ask me something?" I urged her to open up once again. 

"Oh it was nothing Mistress, it's not important", she stated. 

I kinda crinkled my nose at her in disappointment. I hoped she would trust me enough to open up and tell me what emotions she experienced, post spanking. 

"Alright babygirl, well that's us for today", I dismissed her. 

" I think we have clients on Thursday and one on Friday, and that will be it until I see you in my office on Monday. Your new ritual and 'summer school', I guess we can call it". 

I tried to sound enthusiastic, to motivate her. No one wants to hear the term "summer school".

"Should I wear my work attire on Monday Ma'am?" Cassandra asked.

"No, no. Just dress casual Cassie". I told her.

The rest of the week kinda dragged on. Cassandra and I hosted our clients at the end of the week, the sessions went well and Cassandra was still in great spirits.

My sissy maid (Sissy Maid) was back for the weekend with a huge list of chores, training and humiliations in store for him. 

Summer was back at work and on an international flight, with a few legs to the trip. We sexted a bit and she sent me some slutty hotel-room pics, but that was about it. (Summer the Flight Attendant). 

Looks like it's just Cassandra and I, when Monday rolls around. 

She showed up on time, early actually, and I greeted her at the door on Monday morning. 

We sat at the kitchen island so I could explain my expectations to her. 

"Cassandra, this is only one day a week, as you know. But I want you to know that while you're here, on your summer school days, there will be rules, there will be structure and you will have consequences for your actions, is that understood?"

"Yes Ma'am", she squeaked out, still feeling ashamed in herself that all of this is even necessary. 

"Thank you for keeping me on track Ma'am, I won't let you down",

"You better believe you won't Cassandra, now get yourself into my office and wait for me. You're not dressed appropriately for MY school!"

Cassandra sat quietly in my office, a bit puzzled over what this "attire" thing meant. 

I wasted no time in showing her. 

"Your proper school attire is in the closet young lady, go in there and change for me", my tone becoming strict with her. 

She appeared a short time later, pouting and telling me she felt ridiculous in these clothes. 

"You will be in uniform, like a proper young lady, while attending my school Cassandra, do I make myself clear?!" I was not fooling around now. 

"Before we begin the day, I am going to put you over my knee and give you a spanking Cassandra. This is not a punishment, like you experienced last week. Think of this more as maintenance, to ensure you remain focused on our goals, does this make sense?"

She huffed and crossed her arms. 

"Do I have a choice Ma'am?" She back-talked in a snooty tone. 

"Yes you do Cassie. You may choose to not accept my help, flunk the rest of your school program and get kicked out of your dance program", I said. 

I sat and patted my hosed lap. She huffed again, considering her options. 

"Get that skirt off and get over here young lady, stop wasting time. Get over my knee". I snipped. 

Cassandra reluctantly unfastened her skirt and shuffled over to my right side, before draping herself across my lap. 

I gave her a light spanking over her panties. Again, this was not for punishment. She is definitely going to feel like she's been spanked, but not with the ferocity of a punishment spanking.

I gave her 12 swats with the school paddle over her panties and made her count each one out loud and thank me for them.

I was using encouraging words and telling her that I was proud of her, while her spanking continued. I peeled off her little knickers and continued on the bare. 

I think she was more embarrassed than anything, having to be "reminder-spanked" or "preventative spanked", as a 19-year old, young woman. 

Her attire certainly didn't help with her level of humiliation and shame either. 

No tears this time, that wasn't really the goal. Just a very rosy bum and a red face. 

When her spanking concluded we got her uniform back in order and I directed her to the little, school desk. 

"Alright huni, get down to business please. You have all your extra credit materials here, you have your laptop and each and every Monday you will be taken over my knee, just like today, understood?" 

This was to be her strict regiment of maintenance spankings, every Monday, no exceptions.

"Yes Ma'am, I understand. Thank you for helping me". She groaned out, totally ashamed. 

"I'll come check on you at noon Cassie, and you'll have an hour for lunch break ok?" 

I explained my itinerary for the day, which was also written on the blackboard beside her desk. 

"Yes Ma'am", she replied. 

When noon arrived, Cassandra enjoyed her lunch at the bar, while I had to run out for some errands. I told her I'd be back at 1:00PM. 

Cassandra couldn't help but notice the little rack of keys to her right, tucked away in the corner of the bar. It was new, she hadn’t seen this rack before. 

One set of keys had a high-heel charm for a keychain, the other key was just fully red in colour. 

Curiously, she went in for a closer look.

She was only aware of two rooms in this facility that remain locked. One is in the basement, and the other is on the upper floor. Cassandra decided to take the key with the high-heel charm on it and try the door on the upper floor. 

Much to her surprise, the key worked and the door unlocked. The door creaked slightly, as it opened. 

"OH my!" 

Her mouth opened wide, slack-jawed. 

She scanned the room...

It was like a hidden little Speakeasy, tucked away on the upper floor of of Mistress' facility. Everything looked so classy and sparkling new!

Cassandra checked the time, she still had a half hour in her lunch break and Mistress was out. What would be the harm, besides, she's studying and training to be a professional dancer right? 

She knelt down and picked a song, flipping through a few different options. There was certainly no Swan Lake or Nutcracker ballet loaded into this machine.

She giggled, "hehe, this will do". <Problem - Natalia Kills> 

Cassandra then geared off her sweater, untucked her shirt and tied it up above her belly so it wouldn’t hinder her movement. 

She started to work that pole like she's done it before!

Cassandra was having a blast in this secret new room!

The song was so loud however, that she didn't hear the door creak and Mistress Andrea walk in...

To be continued...

Continued in: A Star is Born

Mistress Andrea

xoxo