A Summer with Ali Pt. 02

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"Roll on to your side," he said. "And hitch your knees up a little."

I did as I was told. I rolled away from him and towards the door. I was facing Ali's bedroom mirror. My own face stared back at me. I was covered in a thin sheen of sweat and my hair was all over the place. Reflected in the mirror, I saw Ali lay behind me. He scooted into position and I felt his smattering of chest hair pressed up against the skin of my back. Despite the warmth of his flesh on mine, a shiver passed through me.

"Just relax," he whispered into my ear, before gently biting the lobe.

I felt something cold and wet pressing up against my already-sodden back passage. His fingers once again entered me, this time with comparative ease. I felt the coldness inside the deepest core of me. Quickly the fingers were withdrawn, and I braced myself for what came next.

"Remember to breathe and tell me if you want to stop."

My reflection in the mirror nodded at this instruction. And then I felt it. Ali's dick started to push against my back door. Immediately, it was unlike his fingers; it was warm, soft, and yet hard as iron and large. It felt enormous pushing into me. I breathed deeply lest my eyes pop out of my head.

Ali was gentle with me. He adopted an in and out motion -- pushing in a little then relaxing, before pushing a little bit further. Before I knew it, the head of his dick was contained within me. Despite feeling foreign, it felt right that it was there. With the head of his cock inside me, Ali paused for a moment to let me adjust.

"Are you okay?" he asked.

"Yes," I answered. "It feels... good."

Ali did not respond, but I saw him smile in the mirror facing us. He started to push into me once more. It wasn't painful, per se, but it was uncomfortable. I felt a huge pressure on my arsehole, almost a kind of burning sensation. At one point I almost told Ali to stop as I felt like I was about to be split in half, but I managed to grit my teeth and just focus on my breathing. Suddenly, I felt something inside me loosen up once more, and Ali seemed to be pulled inside of me. I felt his balls rub up against my own, and Ali moaned with pleasure.

He was in me. Ali was in me. Another man had his cock in my arsehole, from root to tip. And it felt amazing. I felt full of him, and I could feel the flesh of his dick pushing against me from the inside. Ali adjusted his position a little and that slight movement caused me to feel a pleasure I had never known -- something electric that sprung from somewhere inside of me.

"Fuck me, your arse feels amazing," said Ali. I felt a tiny burst of pride that he was enjoying my body.

He started to fuck me. Long, slow strokes to start with. He would ease almost all the way out of me before smoothly pushing in once more. With every stroke, that same feeling and pleasure, all new and wonderful, would shoot through me. It was odd. It was so unlike the many wonderful sensations I would feel when my cock was being fucked. I didn't feel like I was going to cum or that I was building up to a release. In fact, at that point, I wasn't even hard any-more. It was deeper than that. Like an itch that had been driving you mad being finally scratched. An itch you had had for thirty years...

As the pace of Ali's dick picked up, I heard his breathing quicken and his hand, which up to that point had been gently placed on my hip, began to grasp at my flesh. He was getting rougher as he used me. At that point I felt desired for the first time. Properly desired and wanted as a sexual creature. Ali wanted me, had seduced me and now he was fucking me. I wanted him to want me again, and to fuck me again. Over and over.

Ali's hand released its grip on my hip, leaving a faint scarlet handprint, and it latched onto my cock, causing me to almost yelp. His hand was still drenched in the lube he had used on my arsehole, and the slickness caused my cock to wake up and harden.

The sensation of Ali wanking me off while simultaneously burying his cock in me was overwhelming. Whatever critical faculties I had at that time disappeared. I was an animal of instinct, living in the moment. As Ali's cock pushed into my ring, his hand ran down the sensitive skin of my penis. My pelvis and spine felt like it had been connected to an electrical main. I threw my free hand back behind me, grabbing a fat handful of the skin on Ali's arse. I wanted more of him inside me -- as much as I could. I started pushing back onto his cock as well.

The feeling of me actively fucking him back must have sent Ali over the edge. With a cry, he came in me. I felt the muscles in his shaft spasm and throb, followed by a sudden warmth inside me. The sensation, along with Ali's hand forcefully hand-fucking me, tipped me over the edge. Like Ali's, my cock gave that familiar pulse and I shot my cum across his bedsheets. The sensation of cumming with something buried in my arse was amazing. It made the release more intense, almost verging on the side of pain. I came a lot. More than I think I ever had before.

We lay panting on the bed for a while. Both sweaty and both exhausted. After a few minutes, Ali's dick softened and withdrew from me. I felt strangely empty.

"Are you hungry?" Ali eventually asked.

"I'm famished. Let's order some food."

"Okay. And then I think we need to have that talk," he said.

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Shaglus_ZieglerShaglus_Ziegler10 months ago

Sexy and real. I have been penetrated before by a man, and my wife fucks me occasionally with a strap on, a rather large one, which I love, but I’ve never had a man cum inside of me. I really want to experience that. I do love cumming with my wife buried inside of me. Cheers 🥂

AnonymousAnonymousabout 2 years ago

OH, MY FUCKING GOD, that was intense! You've managed to capture every feeling and emotion of first time anal with your words. I don't remember pain or discomfort during my first time. I do remember however, a feeling of floating out of my body and looking down at myself getting fucked. I only wish my first time could have been with someone more like Ali. You've written a beautiful coming out story worth a lot more than five stars. Can't wait for part 3 and the after-dinner talk. Thanks, MLF

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