Toby And The Tentacle Beast

The human was bound to the chair as I had requested. He was blindfolded for the benefit of the audience in attendance. He would receive a handsome commission in return for his participation. And hopefully a pleasant experience, though he likely wouldn't be telling anyone about it. I was told just before curtains that his name was Toby and the safe word he had chosen.

The house lights dimmed and the audience grew quiet. The curtains pulled back to reveal an empty stage, aside from Toby. Spotlights focused on my "assistant". I let them take in the spectacle for a moment. The bright lights quickly produced a sheen of sweat over his muscles, which stretched against the white rope binding him across thick thighs and under his chest. A cloth had been placed over his groin and his dick was already pushing up against it. He was eager. And so were several of the audience members, touching themselves and each other.

The music began. I took to the stage, slowly entering the circle of light. The crowd gasped. Most had not seen the likes of me before. I slowly unfurled each of my tentacles, swaying in time with the instruments. Toby's chest heaved slowly as he took deep breaths. I just barely touched him with the tip of one tentacle, gently grazing a nipple. He was pleasantly surprised. I traced a line down from his neck, through the dense hair of his chest, feeling his skin ripple in goosebumps.

"Do you like that?" I stage whispered to him. He smiled and nodded. "Say it out loud for our friends to hear."

"Y-yes," Toby said, "I like it." A whistle from the crowd.

I moved behind him, draping several tentacles over him at once. I wound them down along his arms and legs, tasting him. I drew them taut and felt him squirm against them. Toby's breaths became more shallow. I wrapped one around his neck and gently squeezed. He moaned softly.

With another I traced his lips before slowly pushing it into his mouth. Drool pooled and dripped from the sides of his mouth. I pushed a little further and he gagged, trying to fight the urge. I held it pressed against the back of his throat for a long moment. His stomach clenched. Pulling back, I allowed him to breathe.

"Isn't he a good boy, folks?" I asked the audience as I patted Toby's sweaty head. The audience clapped and cheered. Toby smiled and panted.

His cock jumped beneath its sheet, a small circle of precum soaking through the fabric. Taking a corner of the cloth, I drug it away. His cock curved upward, moving with his pulse.

I wrapped a tentacle around his balls and the base of the shaft, squeezing softly so his dick was as thick as possible. Toby leaned his head back against me, his breath hot against my skin. I rubbed the precum around and along his cock, stroking it slowly. I could tell he was already getting close.

"Not yet," I said and he whimpered.

"Please?" Toby asked. I started to stroke faster. His body tensed and he bucked into the closed coil of my tentacle. "Oh fuck!" he shouted and I stopped. He moaned and grunted. I pulled back a tentacle and snapped it against his chest, just hard enough to leave a red streak. I did it against his thigh. Another on his stomach. I stroked him again, quickly now. His moans grew deeper, so I stopped once more.

"Please! Please!"

"Please what?" I asked.

"Please let me cum!"

"I don't know," I said, "do you think he's been good enough?" The audience cheered again.

I wound Toby up in all my tentacles. I felt every muscle in his body strain as I stroked him faster and faster. "You going to cum for me?" I asked loudly.

"Yes! Yes!" he yelled. He clenched his jaw and grunted as cum shot from his cock out onto the stage in long spurts. The audience went wild. I kept stroking, squishing a tentacle against the head of his dick, tasting his cum. He laughed and twitched, causing the chair to jerk and scoot across the boards.

"Thank you," Toby said breathlessly.

I released his dick and it flopped against his thigh, still pulsing and trailing cum. The audience was now making their own fun. Another successful show.

I began to undo Toby's ropes. "You did great," I said, taking him into my many arms.

"You were great," he said, wrapping both of his arms around me.

The curtains drew closed on Toby's first foray into performance. And somehow I knew, or at least hoped, it wouldn't be his last.