Moneybags and Scumbags - Sex Stories

Moneybags and Scumbags

I don't think she knows quite how much of a thrill it gives me, hearing her describe to me how she's going to tell everybody how worthless I am, how little gratitude I give her, how unworthy of her presence I am and how gracious she is to bother treating me like shit when she could just as easily ignore my every word and I'd still give her every penny. The harsh yet swiftly confident bite of her voice was a sign that she meant every word; you can't fake such sincerity. I adore her punishments, her gifts to me. Every time she pulls my hair so hard my head can't help but be forced that same direction, I thank her as much as my weak, feeble voice can choke out. I kiss and massage her feet every time she gifts me with a spanking session with her wooden paddle, or a wooden spoon. I'll never forget the time I tried to push the boundaries. She'd always told me that rule #1 of our encounters was that I was to act as if my penis didn't exist. I made the unforgivable mistake of telling her how hard my penis was getting as she spit in my face. It was at that moment that she hit it with her paddle. My hands were cuffed behind my back and my legs were bound together while I was lying on the ground, so all I was able to do was grunt and tremble like the pathetic loser I am. "For today's activity, you will wear a spider gag until you drool a puddle on the floor. You will be face down ass up, obviously with your face in the puddle." She spoke to me as she held the spider gag by the ...

... mouthpiece in the crook of her left index finger. "Now, shall we negotiate how much you will pay me?" The corner of her mouth turned up slightly. There was always a glint of excitement that lit up her face when she talked about the money I was to give to her. "Of course, mistress." I handed her the briefcase I was holding. She took it in her arms, clutching it to her chest with a cheerful grin on her face. She sits down on her massage table as she put in the combination to unlock it. She lifted the lid slowly. Contemplatively, she pulled out each stack of twenty dollar bills, counting. "Two thousand, four thousand, six thousand..." Just the sound of her counting my offering made me impatient, thirsty for my punishment. I was relieved as she finishes up counting, stopping at twenty-four thousand. "Oh, look at that. More than usual. I suppose I'm obligated to blackmail you as well." My heart was pounding, and I could feel my face flush with excitement. "I'd love it if you blackmailed me! Assuming I behave accordingly." I got on my knees, an invitation for the punishments to begin. A small smirk lit up her face for a split second before she came towards me with the spider gag. She hooked both sides into my mouth. How excited I was only increased my salivation. "I'd hate to see that pretty dress shirt get messy. Why don't I take that off of you?" She inquired, rather rhetorically as she unbuttoned first the wrists, then the placket. Pulling it off of me and setting it on the massage ...