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Was it the effect of wearing the butt plug? His finger seemed to gain access easily as an inch or two slid around and around, coating the walls of my anus.
His finger left me, then I felt his hands on my hips, lifting my body up until I was on my hands and knees, my arse pointed back at him. I felt his slippery cock-head brush against my smooth cheeks and I knew the moment had arrived. He had led me to this fearfully anticipated moment with such expert coaxing and pleasurable encouragement that I now had little fear. I knew I could do this. 'Why not?' I thought, 'so many others do it, and they live through it.'
I braced my body when I felt him centre his smooth cock-head against my anal ring. "No, don't tense!" he commanded, "relax your whole body, it will go in better that way."
I tried, I really did. I let my body go limp and I felt his smooth hard cock-head again at my anal ring. It seemed to circle the rim. His erection and my target were so lathered up that his hard-on slipped and slid around before suddenly seeming to hook itself into my opening.
He pushed it forward but my tight sphincter temporarily stymied it. I tensed my body and gasped aloud, "Ooh!"
"Relax Jill," he ordered.
Not only was he talking today, but he had called me by my name. The surprise of that seemed to take my mind off what he was doing back there and I relaxed my whole body while I mentally rejoiced that this man knew who his sexual partner of this month really was. The whole head of his cock, back to the ridge behind, pressed through my sphincter and lodged itself firmly in my anus.
"Oh God, that's great!" he exclaimed rapturously. I imagined that, for him, the feeling from his cock was like it was caught in a slippery liquid vice.
But while he was deliriously proclaiming his pleasure, I was grunting loudly from the different sensation of having my arse plugged and stretched beyond belief. It made me think quickly about the size of the instrument that Alan had just forced inside me.
He recovered from his exaltation to advise me, "You should only feel that incredible fullness for a couple of minutes. That will ease, I can assure you. Then, it will be much better."
At least he sounded like he knew what he was doing. As my mind wandered over what was happening to me, I even wondered how different this would have been if I had not been stretched by the butt plug for 24 hours. Could this overfilled feeling have been much worse?
I felt his cock-head twitching inside my anus, and his hands caressing the smooth skin of my cheeks. I figured he was keen to move on. Even in my own naivety of this situation, I at least knew that he still had much more progress to make.
"I can take it," I bravely suggested, and without hesitation, I felt him push in deeper. I had no idea how much more had gone in. It felt like a lot, but I was prepared to accept that it might only be another inch. How much fuller could it feel in there? Was it pain? I wanted to think so, but in reality, it was probably more just extreme discomfort.
I didn't have to tell him this time. He pushed in again. My sphincter having conceded defeat and with no bit of his shaft thicker than the rest, unlike the butt plug had been, his progress seemed to be easier now. No less uncomfortable for me, but obviously easier for him. He knelt behind my bent over body, with goodness knows how many inches of his thick cock buried in my arse. From where he watched above my back, he would be able to see everything, the stretched rim of my anal ring tightly gripping his solid shaft as it lay buried inside my body.
'How much more?' I pondered. And then I found out when his hands gripped my hips tightly and he shoved forward one more time, his balls bouncing against the area between my arse and my vagina. He was in, there was no more of him to come. Alan had successfully buried his complete cock shaft up inside all of my anus and some of my rectum.
As we both knelt there, fully locked together, I could feel his fingers