We have both been vaccinated, and so the risk of adding to this pandemic are slim. It has been for too long since The Disciplinarian has had time with me. We both know this will be a harsh and long overdue session.
I arrive at the boutique hotel at precisely 1:00 p.m. To arrive either early or late will incur extra punishment. I let myself into the room and begin preparations. I lay out all of the required items on the coffee table – cuffs, three sizes of plugs, a flogger, a wooden paddle, ropes, a ball gag, a full bag of clothes pins, nipple clips, and 20 extremely small but strong and heavy magnets. I have no idea if he will use any or all of these, but I was tasked with acquiring and displaying these items, and so I do.
I open the French windows and lean out, per his instructions. Yes, it is possible that people could see me even up here on the 20th floor, but it is unlikely they could recognize me. This is not a city I frequent, and he has stated that while the doors must be open wide, I can remain standing inside the room.
I hear him come in, but do not turn around. He pours himself a glass of water and I hear a chair squeak as he sits to read my list of confessions: I have eaten junk food – often. I have sometimes worn pajamas all day long. I forgot my ask once and had to return home to get it before going to the grocery. I snapped at my assistant five times.
I hear him pick something up and whip it against his hand. The Flogger. He says nothing, but I know what’s coming. I brace myself.
Count, he demands.
I do, keeping my hands in place despite bending over a few times and dancing about on my feet. I must keep quiet otherwise the people below might look up.
I’m sobbing now, but properly warmed up and beginning to find that lovely land of humility I crave so much.
Bend over, he states.
I do, placing my hands on the balcony floor. Luckily, I’ve kept up with my yoga and am quite flexible. He inserts a nozzle and squirts very cold lube into my anus. I jump and squeal, but do not complain. Slowly so as not to harm my body, but firmly so as to let me know there will be no mercy, he presses in the largest of the anal plugs. By the time it is fully seated inside of me I am gasping.
I turn around and knee. His cock is already out and waiting. I am not allowed to touch him without permission, so I open my mouth. He grabs the back of my head and pushes it down until I’m gagging and my lips are brushing against his base. He holds me there, pumping his hips, fucking my mouth, until I taste the sweet hot cream shoot down my throat. He lets go of me and tells me to stand beside the bed. It has four posts and I am to hold on to them tightly. My arms are spread wide and he kicks my feet out to shoulder width.
He stares at me, looking disappointed. I begin to cry. Once again he takes up the flogger and begins to slowly whip my wide open pussy. I cry even harder, but don’t move. That would be disastrous. He stops after ten strokes and picks up the clothes pins. He begins with my nipples then goes down my sides, either side of my labia, and down my inner thighs.
He picks up the wooden paddle.
You will recite to me not your sins, but how you plan to make recompense for those sins. If I approve of your plan, I will knock one of the pins off with this paddle. If I do not approve, I will add another pin to the same area. Begin.
Forty minutes later, all the pins had been knocked off. Many times he had also hit my body with the paddle as well. I collapsed onto the floor, a mess of red welts and tear streaked face. To my further shame, the room was perfumed with my own healthy musk and my thighs were more wet than my face.
Stand up, he said. You did well, so I’ll allow you to come, but only after I do one more time. Bend over the bed.
I scurried to do so, joyful. He entered me from behind and slowly, gently made love to me I wanted to come, but had to wait for him. Since he had already come, this took quite a while. By the time I felt his hot seed on my back, I was sobbing and begging for release. The moment the first hot droplet landed on my skin, I exploded with relief, joy, passion, and any other descriptor one could think of in this situation. I lay there, stunned and exhausted while he showered and redressed.
You did well. Better than I expected after all this time. I’m pleased you haven’t moved. You may take a short nap – no more than thirty minutes – then dress and leave after you have cleaned up here. I’ll have a dinner prepared for you in the dinning room. Go there and eat. Speak to no one except the waiter and manager. After, go straight home. You may shower tonight, say after 10:00 p.m. Only after your shower may you remove that plug. I’ll text you with our next appointment.
I heard the door close. I sighed deeply and smiled, not realizing just how badly I needed this. I felt free.