#3 Chapter 23

Book:Payment To The Mafia Published:2024-6-3

While the various paddles and even several canes drew my attention, my favorite would always be the quirt. I owned several, every purchase from almost eight years before, but my favorite had been broken in many times. I sighed as I wrapped my fingers around the braided lash, another block of memories surfacing.
This was an entirely different situation.
I noticed my collection of anal training plugs, the varying sizes positioned in a row. There was nothing I wanted more than to fuck her in the ass. I ran the tip of my finger over several, finally selecting one that would be a definite reminder that I was in charge. I grabbed the tube of lubricant, slathering a decent amount over the rubber end, satisfied this would be the perfect training device.
For now.
There would be others, fulfilling my sadistic desires.
When I turned around, she stood in exactly the position I required, her legs wide open. As if she’d been through a typical interrogation before. Everything about this woman was becoming more fascinating by the moment.
She seemed to stand taller, clenching her butt cheeks as if anticipating a spanking.
“I’m going to train you in several ways,” I said quietly, no inflection in my tone.
After sucking in her breath, she dared to dart a glance in my direction. I eased the handle of the quirt into my pocket, moving in front of her in order for her to see the rubber plug, red in color, the hue I anticipated her bottom would be after the intense round of discipline. A single whimper slipped past her mouth before she pursed her lips, blinking several times.
“You will wear this until I say otherwise. As time moves forward, the plugs will become larger.” I held the anal toy in front of her eyes, twisting and turning the piece in the dim light. I could see her increasing anxiety, could hear her ragged breathing. “Do you understand?”
“Yes. Sir,” she hissed after a few seconds.
I allowed an exaggerated breath before moving behind her. “Bend over and open your ass cheeks for me.”
“But…” Her expression shifted into one of stubbornness again, her mouth twisting in order to hold back a retort. Her actions stiff, she bent over, reaching around and pulling her delectable cheeks apart, exposing her rosy hole.
My cock ached to the point I was forced to adjust, my balls tight as drums. I ran the tips of my fingers down the crack of her ass, pressing my thumb against her asshole. The moment I pushed the tip just inside, her legs quivered. “Relax, Willow, and this will be much easier.”
Goosebumps had popped along her skin and she dipped her head low. There was no doubt she was completely embarrassed, humiliated about the upcoming experience.
Allowing a slight growl, I positioned the rubber end at her entrance, pressing my other hand on the small of her back as I guided the plug in slowly, twisting back and forth gently.
Willow was unable to hold back a whimper, almost falling forward as I pushed the toy past her tight ring of muscle.
“Oh, God,” she whispered.
“Breathe for me. The pain will subside, leaving you with a delicious and very full feeling.” I took my time until the plug was completely in position, turning once more before tapping her bottom. “Excellent. You can stand. Remember, you’re not to remove this other than when necessary.”
“Yes, sir,” she barked, straightening up and taking several gulping breaths.
I eased the quirt into my hand and took a step back, admiring my work. She would learn soon enough that I was her master. I coiled a portion before moving around to face her again, eager to see her reaction. Once again, there was no obvious sign of distress of any kind. “Do you know what this is?”
She allowed her eyes to fall. “I believe that’s a quirt, sir.”
There was no avoiding the smile that crept along my face. “And how do you know that?”
“You’d be surprised what I know, sir.”
I shook my head, barely able to contain my desire as I brushed the leather portion across her chest, allowing the two ends to fall close to her pussy. Almost instantly, goosebumps popped along her arms, a slight skip in her breath.
“This is a very special implement, one I’ve owned for many years,” I half whispered, my tone huskier than normal.
“To use on all your arm candy. Sir?”
I rolled it under her arm, moving around behind her, tracing her backbone in a slow and steady motion. When I reached the crack of her ass, I allowed the two strands to linger, rubbing them up and down.
Crack!
Her yelp was more out of surprise, but she rolled onto her tiptoes from the single slice across her bottom.
“I suggest you remember your place, sweet Willow.” I continued my path, sliding the ends down the length of her leg and back up the other. “As I mentioned before, I can provide you with pleasure or pain. You’d be surprised how much of both this simple leather strap can bring.”
“Yes, sir.”
So conceited.
So full of herself.
“But you just may learn.” I slid my hand between her legs, swirling my fingers around her clit. “You’re so wet and hot, cherie.”
I could almost feel her gritting her teeth, biting back every nasty comment that she longed to spout.
Willow’s breath caught and there was a slight sway in her body, but she remained rigid, unyielding.
Fueling every cell to the boiling point.
I rubbed back and forth, taking my time, enjoying the ripe scent of her and the way her juice slickened my fingers. “Does that feel good?”
“Fine, sir.”