Chapter 15

I edge forward, resting the sparkly purple head against Jimmy’s reddened pucker, slick with gel and gaping spasmodically in the aftermath of his orgasm. I hold the shaft with one hand and pull aside each ass cheek in turn with the other, trying to stretch him that little bit further and ease my entry. The angle makes it a little tricky, as I have to push up slightly and can’t just add weight to force my way in. I hook my hands over the top of his thighs, keeping him down on the bed and giving me leverage to push into him. I thrust, slowly but insistently, hoping to drive the 2 inch head past his sphincter. Jimmy whines like an injured dog, screwing his eyes shut and shaking his head, but I cannot seem to make progress. I take the gel bottle again, drizzling gel all around the interface of silicone with young, tender flesh and working it in with my thumb. I notice the muscle gives a little more under the kneading of my thumb, and when I’m satisfied that I’ve got all the lube in that I’m gonna I pull back no more than a quarter inch, before pushing forward perhaps only a half, but with all the strength I can muster. Jimmy’s strangled squeal is more cat than dog this time, and goes for staccato repeats as I move my hips in and out with short, sharp thrusts, joined in our rhythm by the jingling of the bell. The movements are small but energetic, my pounding on his sphincter leaving us both drenched in sweat, me from exertion; him from pain and fear. After a minute I look and see that my efforts are succeeding in tenderizing this tight young muscle; the first inch of the oversized glittery toy now firmly ensconced and gripped by the tight ring. I apply more lube, and resume my thrusts, harder and longer now as he is stretched wide enough and I just need to force in 2 more inches before I let his anus tighten on the narrower shaft of the dildo. Another minute of pounding, Jimmy’s screeching having descended into exhausted grunts, and I have gained no more than a half inch more. I adjust my grip on his thighs, and brace my legs beneath me to power my thrust, ready to stop the moment I’m in. I take a breath and hold it before pushing forward inexorably. Jimmy tries to lift away from me, his toned muscle defying my hands, but his restraints only allow him so much before he cannot go further and must surrender his ass to me. He los like a cow in calf, loud, and long, and deep as the inch and a half enters him, leaving 3 inches of length and 2 of girth lodged firmly in his young rectum, which until this afternoon hadn’t seen anything larger than an enema nozzle. I let go the short end of my sparkly purple assistant, and crouch down to inspect my point of entry. There is a fair amount of reddening, and Jimmy is going to be getting reminders every time he sits down for a week or so, but there is no blood to be seen, and no sign of tearing. Good. I give both butt cheeks a firm slap before standing, and get no reaction from Jimmy. Interesting.