An Honest Man

"Hey, did you wanna grab a condom?" I asked a little hesitantly. I was already on the border of discomfort with this butt plug, but I wanted to reward him a little for his patience in stretching me out. I was also morbidly fascinated at the idea of getting fucked by this enormous dick. He scrambled to his bedside table and pulled out a packet of condoms, rolling one down his cock as I eased the butt plug out of my ass. I felt empty and strangely cold; I could feel my ass gaping unusually wide and I wondered idly how long it would take to go back to normal.

He positioned himself between my legs and I dropped my head to the mattress again, offering my asshole up to him. I was so nervous that I was starting to go soft, and I loosely stroked my cock as he drizzled a HUGE amount of lube over my ass. Taking me gently by the hips, he pressed the tip of his cock up against my already relaxed asshole.

The head of his cock was even wider than the butt plug and less tapered, and we hit resistance almost right away. He kept up a steady pressure, murmuring reassurance to me and stroking my thighs and back. I pushed back against him, trying to loosen up, and millimetre by millimetre his cock started to enter me. I could feel my asshole stretching and it felt like it was on the verge of tearing. I was breathing heavily like a woman in labour as Justin's huge cock opened my asshole wider than it had ever been stretched before. I could feel the rim of his head up against my ass and I knew the hard part was almost over and so taking a deep breath, I pushed quickly back against him. As with the butt plug, there was a sudden flash of pain and with a pop his cock was inside me. We paused for a second and I tried to gather myself. With the shaft of his cock inside me I was in bearable discomfort, but I quickly decided that if his cock came out we were done. There was no way the head of his dick was getting back inside me. After a few seconds he pushed a little further inside me, withdrew a little, then thrust again.

"Oooooh yeah...." He moaned as he slowly moved back and forth inside my ass "You're so tight". I suspected that anyone would have felt tight clamped around his enormous dick, I was certainly feeling the least tight that I ever had. He started a slow, firm rhythm, pushing his cock a little further inside me with each thrust. The sensation was extreme, on the very verge of being painful. It was like stretching a sore muscle after a workout, a little painful but overall satisfying.

He started to pick his pace up a little as his enormous cock slid back and forth inside me like a piston. I moved my hips in time with his to make sure his cock didn't slip out. Now that I was getting used to his girth, length was quickly becoming an issue. Each thrust brought him a little further inside me, and he was already pushing uncomfortably deep. He was moaning and grunting, pulling my hips back towards him with each thrust; I have no idea how much of his cock was inside me but there certainly wasn't space for all of it. I relaxed my arms and legs, laying face down on the bed.

That was better; he wasn't pushing quite as deep inside me now. My cock was trapped under me and inaccessible now, but it didn't matter, I knew I wouldn't cum from this. It was less like sex and more like extreme physical exercise. It was enjoyable and satisfying, but a physical challenge nevertheless. His moans got more urgent; my change of position meant that my asshole was gripping him tighter, and some of his length was now being gripped by my ass cheeks. He started to slow down, and I told him not to stop. I wanted him to cum for me.

He picked up the pace, driving his enormous cock into my trembling asshole, and I rose to meet his thrusts as best I could. His dick was deeper inside me than anything had ever been before; I felt like it was in danger of coming out the other side and pinning me to the bed, like a butterfly pinned to the page of a book.

With a final grunt and a deep thrust that felt like it touched my diaphragm, I felt his cock twitch as he came. He leaned forward, his cock still inside me, and whispered "Thank you" before pulling out of me. His cock came free with an audible slurp; my asshole was exhausted and in my mind's eye I imagined it gaping wide. I hoped it wasn't permanent.

I rolled over to see him removing the condom which contained a very normal amount of cum; childishly I had thought that his load would be correspondingly huge. I went to speak and he leaned forward and kissed me, before placing a hand on my chest and pushing me back down on the bed. Gently he inserted the medium-sized butt plug into my poor, tender asshole, rubbing it across my g-spot. His lips found my cock and slowly, tenderly, he sucked me to orgasm with the butt plug inside me. It took some time but eventually I came, filling his mouth with a hot soupy load of my own. He swallowed it and leaned down to kiss me again, and I could taste my cum on his lips.

I was still a little tipsy and when I went to stand up I felt weak-kneed and light-headed. Justin invited me to stay over, and drove me home the next morning.

We stayed in touch and caught up a few times, but we never had sex again. I told him that although it had been fun his cock was just too big for me, and he took it in good humour. We caught up a few times for dinner and over time we lost contact. I sometimes wonder if he's now married to a deeply-satisfied power bottom.

I did end up hearing from Liz again, which led to probably the most intense sexual experience of my life, but that will be a story for another time...