This was the best part — the first session. Mark was a 30 something once upon a time hockey guy with a love for satin and lace. I wore a green velvet wrap dress and patent leather heels. He had picked the dress out one our first outing. It hugged my tits and offered way too much cleavage when I was seated. I rather enjoyed the once over and grins from the concierge and bellboy as I checked in. The shoes were from my collection. You know the ones, with the ankle clasps and little heart-shaped locks — a subtle nod to the kinkster in all of us.
The clicking of the stilettos drew the notice of a couple waiting near the front doors. The three white-haired suits, previously deep in conversation, looked up in unison. One was ballsy enough to tip his glass to me. I smiled broadly and winked, never breaking stride – the elevator opened with perfect timing. I vanished through the looking glass as the mirrored doors closed. A swipe of the room key accesses the concierge floor, a pleasant surprise from Mark.
A bowl of white flowers was luminescent in the late afternoon sun. I repositioned them and laid my case on the table. I pulled my worn jeans and white tank top from my oversized bag and hung them on the bathroom hook. A girl needs to be comfortable when she is educating a sissy boy.
I went about setting things up. A plain t-shirt, a collar with a pink ribbon as a leash on the bed, and a silicone cock ring. A subtle but effective start in setting the mood. That would be after he set up my case and showed appropriate gratitude for my presence. An enema bulb and baby wipes in the bathroom. A long blond wig, a pretty dress with ruffles and bows, and a pair of white ruffled panties were hanging in the closet. He would earn those.
The view from this height was outstanding, yet as I skated my fingertips across the glass, I envisioned his hard cock arching as I pegged him spread eagle against it. The thrill of his naked body pressed against the unyielding coldness, the humiliation of his nakedness on display for the end of day commuters, gave me such a rush. I retrieved my crop from the case, leaving it open for him to unpack as instructed.
My phone buzzed. He was texting from the parking garage.
I texted, “the door will be open. I am going for ice. Come in, undress, your collar is on the bed, put it on. Kneel, facing the window, and wait for me.”
I grabbed the ice bucket and room key and trotted down the hall. I took my time returning to the room about ten minutes later. Mark was on his knees, his clothes neatly folded on the dresser. He was holding the ribbon leash in his hand.
“Give” I commanded. His hand came above his head until I possessed the ribbon. “What a good sissy, you listened so well.” I stroked his hair and moved in front of him, making sure my skirt brushed his naked arm. The velvet was dragging against his skin, awaking his sense of touch.
“Rise” He did as instructed and forgot himself meeting my eye for a moment. My raised eyebrows were enough for him to flush and blurt out, “Sorry, Mistress,” and he lowered his eyes.
“That’s three hairbrush smacks, keep count for later.” I traced down his side and under his balls, ensuring my cleavage was in his eye-line. I stroked his semi-erect cock watching it grow with every stroke of the soft leather.
“How sad you are, men are the weaker sex. Your cock is delicate and unprotected, and your sex organs are like accessories. Do you wish you could hide your weakness?”
“Yes, mistress,” he blushed and went to cover his hard cock.
I stepped closer to caress his head, “good sissy,” pressing my velvet wrapped tits against his bare waxed chest. “Are you ready to begin?
“Yes, Mistress,” Mark blushed and smiled.
“What are your safety words, Sissy?”
“Hamilton for stop, no more. Evita for a check-in.”
“Good sissy. I had given you a few tasks, time for an inspection. Pull out the chair and stand on it.” I sat on the couch, watched, and waited. I took a nail file from my bag, inspected my nails, and ignored him. I drank my water and sucked on a piece of ice, taunting him, allowing my skirt to stay hiked up as I maneuver to dig aimlessly in my bag. I began his inspection. He adjusted his stance.
“Is my little slut getting tired?” I lifted his balls to ensure they were hair-free, I cupped and caresses, his cock began to twitch.
“Almost,” I pulled a stray hair, and he fought the yelp. “Three for the hair, five for whimpering. Women wax without a word. How many is that?”
I stepped back and held my hand to help him down. He hopped down without a word.
“Oh, no! No manners, that’s five with my hand. You are going to have a very pink ass. On your knees, get the brush from my bag, carry it in your mouth to the couch. Place the pink vibrator and lube on the window ledge, let’s put the ball gag over there too. The crop, flogger, and paddle on the end of the bed.” I held his lead. Encouraging him to move quickly, ensuring he was thrown off, mocking the mistakes. Every so often tapping his ass with or balls with the crop. He was completely erect.
“You fucking little pansy. You should be ashamed of yourself, a sad little man, not worthy to touch my belongings. Just touching them excites you. Tuck your shame between your legs. I don’t want to see it.”
He dropped his head and kissed my shoe. He held the position waiting for further instruction. I didn’t move my foot. “Don’t stop.” He kissed and licked my shoe. Nuzzling his head gingerly against my calf. “Good sissy, now over to the couch to take your punishment.” I went to the closest and brought out the panties. “I think you should wear these while you take your punishment before you clean out your ass, and I take you against the window.”
His face turned crimson, and his breath drew hard. He was surprised. Every detail of our conversations was creating this session. As promised, the pain was subtle. What he had not expected was how his humiliation promoted his submission and complacency. The bikini briefs were satin and soft, increasing his sense of arousal. His cock pushing over the top. He struggled to tuck it, but it was so hard all he could do was push is to the side. He fumbled to hide his excitement. I would not acknowledge his effort. I wanted him to own his shame. He knelt next to me, waiting for instructions. I pointed to the table.
“Pass me the brush.”
He extended his reach as he placed himself across my velvet lap. As I slide my hand under the edge of his panties to pull them down, his cock pressed into my thigh, weeping onto the fabric. I could feel his humiliation as I brought his panties down and exposed his bare bottom. Rubbing his lily-white ass, letting my nails brush his balls until he whimpered.
“Eleven with the brush and five with your hand, Mistress.”
“And how many for soiling my dress?”
“But I,” without thinking, he kneeled up. He instantly realized he had not been given permission to move. His mouth was on my shoe again.
“You’re learning, but soiling my dress, your dirty little piss ant. Velvet, do you know how to clean velvet?” Before he could speak, I cut him off. “If you can’t answer, I will discipline your stupidity. Five more! Now, you are wasting my time. Tuck the cock and get across my knee. Count for me.”
I rubbed his ass, letting my fingers hesitate on his asshole, pressing and rotating my finger until an involuntary moan. “That’s it slut show me your weakness.” With my hand, I slapped his ass in quick succession, each smack harder than the one before. He whimpered a little. I cooed his name and rubbed the pinked ass cheek. Without prompting, he checked his cock, was tucked, and reached for the hairbrush and put it in my open hand.
“Why am I spanking you?
“Because I’m a slutty sissy who keeps messing up…Mistress.”
He counted each smack. His ass was red, and he was silent.
I checked in, “need to talk to about Musicals?”
“No Mistress,” he fumbled the panties back up, he was flustered and attempted to cover up. His humiliation was palpable, he knelt at my side, fingering the fabric of my dress.
“You did well, my little sissy, now we can start. Into the bathroom and bend over.”
“How do you want me?” he asked. I removed the collar and place it on the counter.
“Turn on the water and pass me the showerhead.” I retrieved a pair of rubber gloves and opened a bar of soap. “Remove your panties, I’m going to wash your ass.”
Mark got in the tub. “Lean forward and spread your cheeks.” He looked back towards me but did not speak. I soaped his ass and used the showerhead. The humiliation and stimulation engorged his cock. “That will do, dry off, and wait here for me.” He stood in the tub, drying off. I retrieved the lube from the windowsill. The sun was setting. A dusk pegging would have to be next time. Nighttime would have to do. I flicked on a light and returned to the bathroom.
“Are you ready?” he nodded and went to kneel again. I stopped him. I filled the bulb with warm water and a drop of shower gel. I lubed the top of the oversized bulb. “Spread your checks.” He did as he was told. As I inserted the bulb, he drew breath. “I washed you and now I am cleaning out your pathetic ass, and you don’t thank me. Ingratitude is an insult. Ten more smacks with the brush.” My voice was the sternest it had been all session. I left the bulb in his ass. “Hold that there.” I removed my panties, balled them up and stuck them in his mouth.
I emptied the contents of the bulb into his ass and waited. He was fully erect with a mouth full of worn panties. As he stood in front of me, I began to stroke his cock until he was utterly engorged, and he was unable to stay still. I caressed his ass; he was holding it tight. At least 30 minutes had passed since I had filled him with warm soapy water. “You can sit on the toilet, but I will be very disappointed if you use the toilet without permission.” He sat, and his ass began to leak. His eyes widened in acknowledgment that he had failed. I kept going with my plan. I pulled perfectly pink nail polish from my bag on the counter.
“My sissy must look her best before we continue. Give me your hand.”
His ass continued to leak, and he continued to blush. As I finished painting his pinky, I told him to release it. Mark was mortified, but out of options, his bowels evacuated as I continued to paint his nails. He had no control over his body. His cock had been torturously edged, his gut gurgled and squirted. He had a mouth full of dirty underwear, all the while I painted his nails, made ugly faces every time he passed gas. I explained how lucky he was that I was willing to raise him up from being a dirty pig to a pretty little sissy who I was going to peg for the whole world to see. When I finished his nails, I removed the underwear from his mouth and left him sitting there, unable to do anything except wait for his nails to dry. I put a piece of gum in his mouth, turned off the bathroom light, and closed the door.
I put on my harness and dildo, under my jeans and pulled the tank top over my braless tits. I grabbed the dress and wig and brought them to the bathroom. Time to turn things up a notch.