Page 33 of Island Daddy

His eyes liven when he catches sight of my favorite riding crop unhooking from its place on the wall. “Is that—” he tries speaking, yet I interrupt him.

“Quiet, boy,” I command. “You’re to take this punishment without talking,” I hiss playfully.

He grimaces the moment I graze the switch against his exposed nipples, slapping them with a moderate amount of force. Another pang into this tightened chest of his doesn’t make him flinch in the slightest.Perhaps he’ll enjoy far more than a crop.I shuffle behind Kragen to a box of clothespins on the farthest wall. The boy’s expression matches precisely to that old guy in the wheelchair from Breaking Bad, yet remaining hushed as instructed.

All that being said, he tremors in what appears to be enjoyment at the slight pinching of his nipples. Another delightful groan follows the prior while I finish fastening them to his exposed torso. His skin seems thinner and much more tender after the fourth closure, as I get closer to his dick performing a ballerina pirouette.His hole needs some attention now.Without skipping another beat, I reach behind me to retrieve a golden-yellow ten-inch dildo from its shelf.

If Kragen grimaced at the sight of clothespins, he’s sure to sway back and forth in pleasure with the girth of this motherfucker in his hungry asshole. After a generous slather of Boy Butter, I slide a few fingers with remnants of the lube into his eager hole. A slight moan escapes his mouth as I prod deeper, rubbing straight up against his prostate.

“God da—” he wails, stopping immediately to obey my instruction.

His ass throbs as I grace the circumference with the tip of my silicone toy. The boy bites his bottom lip with another delightful wail. Apparently quite forcefully, because his dimples may be permanently frozen in place.

Another grunt from me. “Feels better than the one on Maui, yes?” I heckle the poor fucker who’s gritting his teeth by this point.

He nods in agreement, though I can tell it’s the widest he’s likely ever taken in his natural born life. I twist the dildo with a snicker, fully cognizant of where his pleasure spot is up there. The toy, appearing much like a pineapple, has blunted splinters of silicone protruding from the sides. Not sharp to cause any tearing, yet just enough pleasure to make the boy exult in place with vehemence.

Kragen winces. “Son of a—”

“What did I say about talking, little boy?” I shoot him a serious stare.

He glances down his naked abdomen to see the toy plunging into his asshole at the rate of a jackhammer, but the impact of a fucking freight train. “Ssss-ssorry Daddy,” he winces.

“Are you learning your lesson yet?” I thunder seriously. “Little boys don’t rub their noses where they don’t belong, do they?”

He returns my sentiments precisely how I intended for him to. A total look of relief washes his face, as I slowly pull the dildo from his ass. Color returns to his cheeks the second my toy retracts from his deep void. Almost as if the silicone cockblocked his ability to pump any blood through the upper half of his body. I’m no doctor, but I’m pretty sure the boy’s pulse could be read near his gaping hole.

Kragen nods with what appears to be absolute delight. Now is the perfect time to introduce the next element of my desire. Electricity. He huffs while trying to catch his breath, as I shuffle behind him to slip my hands into a pair of gloves. A snapping sound reverberates around the room when I tug on the last cuff.

Even though this is a completely soundproof space, anything can be heard bouncing from wall to wall. My Banana Boy whimpers in what I assume to be uncertainty. This next part will most assuredly come flying from out of left field.Perhaps he’ll enjoy it as much as I will.A brief, yet satisfying cackle wallows through my clenched teeth.

I retrieve the small sounding rod, a bottle of Surgilube, and sanitizing wipes from their shelf. Meanwhile, I juggle a voltage box with my other arm. The boy couldn’t appear any more frightened than he currently does, wincing loudly as if I’m wielding a hacksaw or a sledgehammer like Annie fucking Wilkes.If he were to be an author, this could make for quite the comeback sequel. Surely to rack up a few mil at the box office.

“What’s that?” He cowers at the sight of red and black cords intertwined with my fingers.

Another coarse grumble falls from my throat, as I shoot him a brooding look. “I’m pretty sure I asked you to take this punishment quietly, little boy,” I grunt, wiping the silver rod with a sterilizing pad. “Are you gonna come out of this Daddy’s champ—mmm?” I finish, my tone rising to the perfect upper octave.

He nods in agreement, appearing intent on seeing this through to the end.

“Okay then,” I reply, teasing the tip of his cock with the end of my lubricated sounding rod. “Remember,‘pineapple’stops it all,” I add sternly. “Do you trust Daddy to continue, Kragen?”

The boy nods again. Convincingly enough anyways. Surely if the roles were reversed and I didn’t know what this felt like, I’d probably have shat myself by now. Kragen’s quite the trooper, proving that he trusts me to test his capacity for feeling the most pleasurable pain he’s probably ever experienced. His dick twitches insatiably at the mere touch of metal, barely even a centimeter deep inside. Though my sight doesn’t fray from what I’m doing, I can hear the boy huffing and gasping as the rod gently glides down his urethra.

“Mmmmmm,” Kragen moans. “Huhhhhhhhh—”

I click my tongue. “You’ve not felt anything like this have you, boy?” I ask, catching a glimpse of his youthful aspect shuddering with an abundance of delight.

His flush face nods in approval, maintaining total silence at this point. There’s nothing quite like a narrow object being inched down the same organ which our sweet release propels from. But the first time is usually the most harrowing, because the sub isn’t certain how it’s going to feel until it happens. The fact of the matter is, insertion’s only part one. What’s about to follow will drive a strident pain to the veil of his very existence.

The boy’s eyes enlarge to the size of coconuts, as my fingers hover each tiny dial on the voltage box. It doesn’t take a telepath to know that Kragen has surmised wires and a metal dowel must mean electricity. Definitely not judging by the intensity of his facial contortions right this moment. He whimpers softly the minute my fingers grab hold of a knob, kickstarting the amperage just shy of 50Hz. Since he’s a total beginner, I don’t intend on exceeding more than three times that.I doubt I’ll push 100Hz before he’s singing the safe word like a fucking canary.

Kragen wriggles his body at the electric pulses being shot inside his dick. Meanwhile, his breathing picks back up to the rate of a steam engine firing on all pistons. Both eyes shut as he feels the intense throbs growing deeper and harder. One more slight turn of the dial compels me to reach in between his thighs to provide a helping hand.

“Uhhmmmm,” he yowls through gritted teeth.

“You’re doing so well, little boy,” I praise him, stroking his pounding cock. “I think we can go a little higher, yes?”

His cock jitters within my grasp at the sound of more praise. He’s liable to be compared to my Nani, when I admire her for not ruining my office if I’ve left her unattended for too long. He winces instantly, shaking his head in the process. But the safe word hasn’t been activated, so Daddy’s lesson persists.

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