I started his bootblacking like I had many times before. Lightly lifting his right boot onto my thigh. Cleaning it twice. Scrubbing the catwalk with a toothbrush. Checking for frayed threads to singe down. He, however, decided to not treat me as he had before.
He lifted his left boot and placed it on my free thigh. He pushed into my flesh. When I lifted his right boot to clean in close, he lightly rubbed my face, my chin. I kissed and caressed his leather as I continued to work.
He brought his left boot from my thigh to my chest. He pressed into my breast, stepped into my nipple. He kicked my chest, rocking me back. He used his left boot to spread my legs and began lightly kicking my pussy. I had no choice but to pause my work, marveling in the arousal from his torment. His kicks subsided mere seconds away from my orgasm.
“I was a few breaths away from asking permission.”
“Then I did you a favor because I would have said no.”
Finished with his right boot, I began cleaning his left.
“I was hoping I’d make you loose your place.”
I smiled to myself, happy to have again risen to a challenge. He continued to press into my flesh, torturing me as I loved his leather.
When I finished cleaning, I asked if I could kiss his boots. He replied, but I couldn’t hear him. Grabbing me by my nipples, he pulled me up and into his arms.
“You can after you kiss me.” Again our lips met, playing as we liked. Again he grabbed my hair and pushed me down to his boots.
My lips softly caressed his leather. My hands massaged him through the barrier. He punched my ass, my back. For a split second, I found it funny that he attacked me from behind while Jim had attacked from the front.
He reached down and started fingering me. He teased my clit before easing his fingers into my pussy. As his digits entered me, I immediately asked permission. He gave it, and I rode his hand hard through my orgasm.
Removing his hand, he began slapping my pussy. Over and over stingy pain mixed with my hot arousal. I took his strokes, one after the other, not knowing if I ever wanted him to stop. Hit followed hit; I moaned with the pleasure. Eventually the pain went far beyond my pleasure, and I rolled my body over to avoid his slaps.
Grabbing my hair, he brought me again to his face.
“Kiss me. Kiss me. Once you kiss me, you can suck my cock.” He held my hair, keeping my lips from his. When he sought fit, we kissed once again.
He pulled my head down onto his cock, and I gladly enjoyed his dick in my mouth. Within moments of my glee of finally having his cock in mouth again, I felt the first of his wicked cane strokes. He aimed for my ass, one of his favorite targets. He said he would stop when I stopped sucking his cock.
I took his hits. In a moment of desperation, I switched to sucking his balls, hoping this was a loop pole in his order. I was given a moment of respite before he began again with his stingy strokes.
I sucked and sucked, wiggling and squirming my body about trying to avoid his hits. I switched back and forth between his cock and balls, happily sucking away. He grabbed my hair, pushing me down further onto his cock. I practiced my deep throating as he fucked my face.
He pulled me off of him. Sadly, he tucked his dick away.
“You made my Punisher face uneven.”
“He can’t be smiling; he’s the Punisher.”
“As if you couldn’t have a big grin on your face as your inflicting pain.” The vision of him torturing me with his Twisted Bitch during our first play date burst forth in my mind.
I went back to his boots. Using my Huberd’s, I conditioned his leather. There were a few especially dry spots that I focused on.
In a moment of pure silly, he used the toes of his boots to push on my breasts and nipples, jiggling them for his amusement. We both laughed.
“You getting anything out of this?”
As I continued my conditioning, he again pressed himself into my flesh.
Finished, I rubbed his chaps, asking if I were to move onto them next. He sadly declined. He had another play date that evening.
Grabbing my hands, he started to pull me into his lap. Releasing my hands, he grabbed me by my nipples.
“Having trouble getting up?”
“No. No. No trouble at all.”
I straddled his legs; he rested his arms around my waist. Once more we kissed. Again he pinched my nipples. Gripping my breasts, he squeezed hard. With the pain and pleasure rising, I rocked my hips in his lap and asked permission to cum. He granted my request. I breathed hard, and he kissed me as I came.
He asked me if there were any classes I planned to attend in the morning. I wasn’t certain, as my brain was rather foggy. We agreed to text to coordinate when on Sunday I’d be able to finish my service to his leathers.
We stood. Surprisingly, he came in close and grabbed my breasts again. I leaned into his body, his chest, gasping. I begged permission. He said yes. I rested in his arms as I breathed heavy and came hard. We hugged.
On my hands and knees, I collected my kit into my cigar boxes. Ever one for the wacky, he took his rolled up yoga mat and began smacking my ass with it.
Our things collected, we set off in search of his next play date. With her nowhere to be found, we separated. Not a minute later, she found me. Searching the Dungeon and the Champagne Room, we did not see him. She said she would wait at the bootblacking station.
I tried upstairs and found him in the lobby. Grabbing him, I brought him to her.
They set off for their play date. I headed back to my room to grab my rope, and took a moment to journal.
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