Little Man

I crawled into bed and began adjusting the pillows, giving him a clear view of my ass as I did so. Once the pillows were set up, I plopped my back down, spreading my legs, presenting myself to him. He quickly took his place between my legs and started gently batting his penis against mine, sending small strings of precum flying. Seeing us compared directly really emphasized just how massive he was, and I was hit with a sudden realization. I reached over to my nightstand and opened the drawer, pulling out a bottle of lotion I kept in there. It might be quite the challenge to take him in me, especially since it's my first time.

He grabbed the bottle from my hand and squirted a little on his index finger before bringing his hand between my legs, rubbing it into my asshole. He gently pressed into me, his finger sliding in with little resistance. He quickly applied lotion to another finger slipped it in, again easily stretching my anus to accommodate. He tried for a third finger and met slightly more resistance, but was soon able to fit all three comfortably. After a few minutes with three fingers, he repositioned himself so his cock was just touching my ass and squirted some lotion into his hand, rubbing it along his entire length.

He began to lightly press the tip of his cock into my ass, providing me with an immediate sharp and searing pain. I quickly put my hands on his chest, stopping him from moving, which he did instantly. I breathed heavily, trying to get my body used to the feeling. After about a minute the pain died down and I slipped my hands down his chest until I was holding his sides. He took that as his cue to continue, and added ever so slightly more pressure into my ass. The pain was still there, but tolerable now. Eventually, I felt a pop as his head fully penetrated me, causing me to release an involuntary moan. He stopped when he heard me, but I looked at him and nodded, beckoning him to keep going.

Suddenly, he thrust the remainder of his cock deep inside of me, causing me to cum immediately. My entire body convulsed as my penis began to dribble cum out onto my stomach. This orgasm was unlike anything I had ever felt before, spreading through my entire body rather than focusing solely on my penis. Sam looked down at me, watching me cum like a girl because of his cock, and waited patiently for me to come down from the high. When my convulsions finally settled, he scooped up some of the cum that had puddled on my stomach with two fingers and brought them to my mouth. With his fingers in my mouth, the taste of my own cum which he had milked out circling around my taste buds, he began to thrust in and out of me.

His fingers were the only things stopping me from moaning each time his cock smashed past my prostate. With every thrust I felt my body seem to fill up and get empty again, aggressively flowing back and forth. I could tell Sam had now lost all self-restraint as he pounded into me again and again, and despite the force I felt only pleasure and no pain. Each thrust seemed to send another shockwave of my orgasm through my body, reliving that moment over and over. As he picked up speed, I could tell he was getting close to cumming deep inside me, barely a minute after entering me.

Suddenly, I felt my body lift off the bed as Sam effortlessly hoisted me into the air. It was as if he was now simply using me as a toy for his cock, and I had never felt such euphoric bliss. I wrapped my legs around his waist to gain stability and I pulled myself in to kiss him once again. As soon as our lips met, I felt an intense warmth begin to pulse into me as he started to cum. Feeling him shoot into me brought me to another orgasm, the first time I had ever experienced two so quickly, and my penis leaked whatever cum it had left onto his stomach. I moaned into his mouth as he continued to unload into me.

When he finally finished, he let me fall back to the bed before collapsing onto me, his cock still inside me. His weight laying on top of me felt stifling yet comforting, as if I had never been safer in my entire life. I stroked his hair gently as I felt his cock begin to go limp inside me. I closed my eyes, just living in the moment, feeling happier than I ever had before. With him on top of me, we drifted off to sleep.

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I woke up in the morning to find myself cradled under Sam's arm. I was fully nude and the cum had been wiped off of my stomach, so I guess he must have woken up at some point during the night and gotten us cleaned up. I gently draped one arm across his torso, trying hard not to wake him up, and I just looked at his sleeping face for a while. I thought about how badly I treated him, how I lashed out about my own inadequacies and he just happened to get caught up in it. How I pushed him away when he tried so hard to reach out. And despite it all, he still came back. Lying there, under his arm, I never felt as if I had loved somebody more. But maybe more importantly, I had never felt more loved. I felt as though I was about to start crying when I glanced down and saw his morning wood poking straight up into the air. What a great way to distract me from my sentimental side, I thought. As I sat up and crawled between his legs, I realized that maybe this year actually would be the new start I was looking for.