I fingered KY into him, widened his hole with my searching fingers, and lathered up my sheathed tool.

I turned him on his belly and spread his legs. My sheathed cock went to his asshole, and I held his hips firmly in place with my hands while I slowly worked my way into his tight hole.

"Ahhhhh! Oh, God, oh God. It hurts so bad!" he was screaming. He was fighting my grip in his hips, arching his back up and trying to writhe his ass away from my assault.

"Do you want me to stop?" I asked. "You know Ted is longer and thicker than I am. If you wait for him, it's going to hurt more. If you manage the initial pain with me, you'll be ready for Ted when he's ready. So, do you want me to stop?"

Silence for a few seconds, as I held myself there, my cock just an inch inside him, waiting for him to make up his mind, willing him to let me continue.

"Oh shit," he whimpered. "No, don't stop. But go slow. P-l-e-a-s-e! You promise it will stop hurting?"

"Yes, just moments from now you'll be in heaven. And then when Ted's well, you'll be able to take him with only pleasure."

Daren whimpered and sobbed then while I slowly plowed to the hilt and held there, waiting for him to accommodate me. He had grabbed at the legs of a nearby wrought-iron table and was hanging on for dear life with white-knuckled fists. He also was all tensed up and hadn't taken a breath for I don't know how long.

"Relax, Daren," I said in my soothing voice. “I'm all in now, it's all pleasure from now—but only if you relax and let the tension out. And breath. Breath normally.” I let loose of his hips and started rubbing his back, helping him to relax, which, at length, he did. Then I started to slowly pump him, and he did, indeed, start moaning and sighing like I was taking him to heaven. And shortly before I came deep inside him, he was meeting my thrusts with thrusts of his own.

When I had shot off, I collapsed onto his back and gathered body to me in a close embrace.

"So, how was that for your first time?" I whispered in his ear.

"Oh, God, oh God," he was whimpering again, but this time his voice had an entirely different, satisfied and lust-laced tone to it.

When we had rested, I changed to a fresh condom and we sank back into the hot tub, he again in my lap, but facing me this time, and we kissed deeply as he slowly pumped his ass up and down on my cock.

All during this second fuck I was trying to hold my triumphant thoughts in check. The first thing tomorrow I'd be at the hospital, with flowers and candy for Ted—and with a gloating description of how I had seized the opportunity to take advantage of his months of cultivation of Daren to sweep in and usurp his deflowering campaign.