mishkhail:

“Sir, I concede my argument Sir. Sweatpants can be sexy, Sir. I should not have argued with you Sir.”
“No Kenny, I like when you challenge me. It gives me a chance to flex my creativity. Besides, you seem to learn better by doing than talking.” I walk around to the side of the bed so I can get behind him; I kneel on the mattress and handcuff his wrists together.
“Uhhh why did you do that Sir?”
I slide off the bed and pick the remote up off the desk. “Oh for this.” I turn on the vibrator buried deep in the tightness of his ass, from when I put it in there at breakfast.
“Nnnnggg!” Kenny squeals and squirms. “Oh you put it on high, Sir!”
I turn it down a notch. “Better?”
“I don’t know if that’s the word I’d use!” he gasps.
I grin and set the timer on my phone. I show him the numbers on the screen counting down. “You have five minutes to cum in your sweatpants. After that, you will finish tidying your room with a wet stain.”
Kenny gulps. “Five minutes – wait, why wet Sir?”
“So every time your loose cock brushes up against the wet, cold fabric, you will be reminded that your orgasms and pleasure are at my mercy, and my will.”
“I’m definitely at your mercy, Sir. Oh god,” he groans.

“Look, you’re getting so hard – must be tight, straining with the rope around it.” I run my finger across the length of his shaft. My boy whimpers.
“By the way I forgot to mention something.”
“What is it Sir?” Kenny asks. His face is becoming flushed.
I hold up my phone to show him the time. “If you don’t finish in five minutes, there will be punishment.”
Kenny gasps. The conflict of annoyance, horror, and arousal shows on his face and in his eyes, and my lust for him only grows. I watch him as he squirms and tries to manipulate the plug inside using his posterior muscles. A wet spot blooms on the heather grey fabric. I lick my lower lip and watch him. Three minutes to go… he hasn’t had an orgasm or permission to touch his cock in three days, this should be easy for him. But if not? It’ll be much longer than three for his next one.

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Captions are fictional.