Chapter 14

Jimmy whimpers as I stack my pointer and middle finger together, carefully applying pressure to the slick rectal muscle, gradually kneading it. Slowly it relaxes, not smoothly but stuttering, clenching with every muffled sob that comes from my little bell boy, sounding now much younger, the years falling off as his fear and pain and humiliation mount, stripping his bravado, reducing him to a small, scared child.

I push my fingers in, forcing his tight pucker out to maybe half an inch wide. I twist my fingers, trying to spread that clenched ring of muscle, to stretch it without tearing it. I want to break Jimmy, but I don’t want to be taking a kid to the ER and have to explain a torn anus or, worse, a perforated bowel. I feel my fingers start to catch on the tender membranes of his rectum, and squirt more lube directly at his hole, using my fingers to work it in and enjoying the little grunt as the cool gel hits his hot insides.

A few more minutes work and I am able to squeeze my ring finger in as well, clustering the three together, twisting and turning to stretch him out to a full inch. I now start to withdraw my fingers, right out to the tips, letting Jimmy’s little pucker start to pull in again and plunging back in, encouraging the muscles to relax swiftly under pressure. I drive in and out, changing the timing at random, leaving Jimmy tensing, constantly wondering when my next assault will begin. Each penetration brings a little yelp from Jimmy, a flinch and the tinkle of his bell. He tries to force himself up the bed, away from my intrusion but his tight bonds leave little scope for that. On the last of a dozen thrusts I press forward hard, as deep as I can reach, grinding my knuckles against the well-worked tissues of his anus. The usual yelp ascends into a prolonged squeal and Jimmy manages to push his whole torso perhaps 6 inches off the bed before collapsing, panting, unable to expel the intruding digits. I ease back slightly, probing back and forth and pushing up behind his penis. My fingers brush against a little lump, no bigger than a date but a little firmer, and I know I’ve found my target when I hear the jingle of a bell coupled with a sharp intake of breath, then held, from Jimmy. No more than 3/4 of an inch past the sphincter, his bite-size prostate is there for the taking. I withdraw my ring finger, letting me get the pads of two fingers pressed hard against the wrinkled surface. I am rewarded with a grunt from Jimmy, his hips trying to buck as I work back and forth over the little cluster of nerve endings. My free hand reaches up to press down on his lower abdomen, giving me better control. I rub swiftly, then slowly; firmly, then gently; fingers together pressing up, then forked to rub against the sides. Jimmy’s whimpers have morphed into little gasps, his penis bobbing with every press and rub, the jingling now incessant. Sweat forms and pools, glistening at the base of his sternum, and his reddening face rises, craning to see what I am doing, discomfort and fear now fighting pleasure and lust in his eyes. His heart races - I can feel it pulsing through his body and see his glans throb as the pressure rises and falls. I add urgency to my stimulation, increasing tempo and pressure, building up and up until it seems that, rather than trying to buck away from me, half the time Jimmy is trying to grind his prostate down onto my fingers. I press on, or rather up, and am rewarded by seeing my little pet’s whole body try to contract, muscles all trying to pull at once as his penis erupts, pushing three large squirts out, the first catching his left shoulder, the second, stronger, splattering across his forehead and into his hair. The third is weaker and squirts up and almost straight down to pool in the blond bristles and over the cock ring at the base of his shaft.

With Jimmy relaxed and blissed out on endorphins I withdraw my fingers and reach for the oversized dildo, lubing the short end and sliding it home into my vagina, testing my grip, even managing to make it lift slightly. I coat the longer end in gel too, taking particular care over the bulbous head. I take a deep, quiet breath, lining the tip of this absurd toy up with Jimmy’s slightly gaping anus. It’s now or never.