Chapter 18

Jimmy grimaces, fighting the pain in his ass but, as I force another inch inside him, he cannot hold on more than 3 or 4 seconds before a low howl escapes his lips, followed by panting gasps. I use my hold on his hips as leverage to angle my thrusts down, hoping to find with firm silicone the same little gland I found earlier with my fingers. Now 4 inches into his rectum, I jerk in and out sharply, but no more than half an inch. Little grunts and groans accompany my rhythm, and as I speed up the groans turn into squeaks. With careful movements, keeping up the pattern of thrusts as I move, I release one hip and lean forward, reaching my hand around Jimmy’s waist to his dick. It is still very hard as I brush my fingertips against it. Hot and dry and smooth. I dance my touch down the shaft, over the freshly shaved balls, plucking gently on the loose skin of his scrotum before travelling back up the shaft and gripping the foreskin with thumb and forefinger, pulling it together over the tip of his glans, causing a little jerk as pressure is applied to the sensitive head beneath. Even with the movement of my thrusts I can feel Jimmy’s pulse racing, blood thundering through the vessels in his dick. I keep my hold on his foreskin but wrap my other three fingers around the top of his shaft, squeezing more and more firmly. At the same time I drive my pelvis forward, applying my force to my thrusts. Jimmy lets out a whinny of pain and tries to shuffle forward away from the purple sparkly invader.

“None of that, Jimmy.” I deliver a hard slap to his butt cheek before reaching forward to grab the chain of the cuffs attached to his collar. I haul on it, his squeaks and grunts replaced by gurgles and panicked choking sounds as his head is forced back and I use the leverage to force my way further into his ass. I can’t see right now how far in I am, but I’m almost past caring. My own arousal has been quietly building and my clit is begging for attention. I adjust my hips and realise that the right angle can put pressure on my g-spot and Jimmy’s prostate at the same time.

My strokes now switch to long, slow and inexorable, pushing in as hard as I can on the downstroke, hauling on Jimmy’s collar with one hand, the hand on his dick pressed into his abdomen, holding him tight. He gurgles and sputters and groans, not getting to scream as his air is restricted. Then for the upstroke I press down between his muscled shoulders, tug on his shaft and hear him moan at the waves of sensation crashing over him. Giving 2, perhaps 3 seconds for each stroke I maintain this for several minutes, my own arousal mounting agonisingly slowly. I notice Jimmy’s breathing getting heavier and more ragged, more noises of pleasure and fewer of agony despite the abuse he is enduring. I decide to be generous and turn my grip on his dick into a vigorous handjob, continuing my thrusts into his butt even as the little squeals and gasps build. It is barely thirty seconds before Jimmy spasms, quivering uncontrollably as he squirts a small amount of cum onto my fingers. I cease my thrusting, releasing his neck, and the dildo from my crotch, letting him collapse sideways, his chest haulling in ragged gasps, his tanned face red-purple from exertion and oxygen deprivation. His eyes are glazed and he is weeping again. I raise my cum-filled fingers to his mouth and smear his semen over his lips before pushing them into his mouth. Jimmy’s tongue rises instinctively, licking and sucking on my fingers even as his gaze remains unfocussed somewhere in the corner of the room. He licks me clean and I push my fingers a little further in, testing the spasm of his gag-reflex before withdrawing. His face looks very cute smeared with semen. Still, much as I like looking at it, I can think of better uses.

I glance down at Jimmy’s ass and see barely 6 inches of silicone sticking out.

“Nice job, Jimmy” I say, patting the exposed portion.

“Thank you Mistress Santos” he responds, on automatic, still well out of it.