His Hardcore Punishment

I never expected when I had agreed to go over to her house at 3 am on Christmas morning I’d be receiving such a interesting Christmas gift. Anna was sitting in her living room on the couch when I finally stepped into her cozy little home. Her shaggy multi colored haired going nicely with the dark make-up she was wearing, it was the usual make-up I saw her in after she’d gotten home from handling a client.

“Anna whats up?” I asked “Tinsley i’m sorry to have called you so late but….a old friend from school gave me a strange request and I knew it was something you’d like to help me with” she explained shifting up off the darkly colored sofa.

Instantly I found myself intrigued and merely nodded my head as she glided past and had me follow her into the backroom. I knew Anna’s back room was off limits because it was what she used for clients who were spending the night at her home or a guest room after wild parties. Stepping in, there was a rather lithe and tall male on all fours. His hands had been cuffed and had a chain leading from the middle of the cuffs to the bottom of the bed keeping him from moving much. There was a spread bar between his legs, moving closer I could see a ball gag in his mouth and a blindfold covering his eyes. The thing that caught my interest the most was the ear plugs in his ears. “He cheated on his girlfriend….she knows what I do for a living and requested I make him pay. He agreed because he wants her to take him back” Anna told me filling me in on the details.

I nodded my head smiling softly, now I understood fully why Anna had called me. I’d told her all I wanted for christmas was some good old fashion naughty fun. Anna went about getting me the necessary items I needed for this punishment. Taking hold of the riding crop I felt it fitting to start off small while Anna moved over to his prone form with a piece of red ribbon. She tied it carefully on his cock, he would not be cumming anytime soon. Taking the tip of the reading crop I dragged it slowly and lightly over the flesh of his shapely tiny little ass. He shifted obviously nervous and so I merely moved the crop back and brought it down swatting his ass hard. Every time he moved I allowed the crop to connect with his soft flesh, it took 6 swats for him to finally realize if he stopped moving i’d stop hitting him.

With the lesson learned I lazily dragged the riding crop over his body nice and slowly and discovered he was ticklish on the back of his thighs, that was too bad for him. As soon as he moved I once again began my round of punishment upon him. Tickling him just to force him to either keep still or take the punishment, by the time I was done his body was littered here and there with beautiful red marks. He was breathing heavily into the ball gag his body taking in ragged breaths. I picked up the smallest buttplug that had been taken out  before going over to his ass and having anna spread his ass cheeks open. The only lube he’d be getting was spit, I spat on the butt plug and then again on his tightly puckered hole.  Slowly forcing the plug into his tight little ass letting it stretch out, he struggled but I didn’t care because his attempts to stop me were just that…pathetic little attempts.

Taking out my phone and glancing at the time I had at least 3 hours to play before I needed to be home. I didn’t want my brother waking up to discover me missing. Looking at the male before me, the back of his legs quivering I couldn’t tell if it was from fear or pleasure but either way by the time I was done I knew he’d never be the same…..

You wanna know what happened next?