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I was a bit sceptical. But when he saw that I was doubtful, he pulled my hand onto his crotch. I noticed two things - the heat coming from his shorts, and a fucking huge weapon, twitching and growing. I didn't have to think twice. I slipped off my shorts and exposed my ass to allow him to lube me up. He didn't need a second invitation. He lubed me with the same softness as before, working his way gently into my ass. I went hard immediately. He lubed up the butt plug with his other hand, and worked the very tip into my ass, as he withdrew his finger. He worked the plug in as far as he could without applying any sort of real pressure. It felt absolutely lovely, a nice snug fit!

I was delighted with myself, and told him: see, you can fuck me. Again, I couldn't believe what I was saying. He laughed, he told me that I had about 2 inches of the thinnest section in me. I'd need to get the whole thing into me if I was to be in a position to fuck him. I told him I love a challenge, but secretly I was concerned. I never imagined when I saw the butt plug that I'd have to get much of it inside, let alone the whole thing. There was about another 6 inches to go, and at the widest part it was about 3.5 inches wide, maybe more.

So I sat down gently on the plug, holding most of my weight off the plug & the seat. As Leroy drove, maybe to give me encouragement, he worked his cock out of his shorts, and played with it. He put my own hand on it and guided it up and down the length of it. It felt amazing. I could just about get my hand around it. And I noticed that as I was doing this, I was leaning a little forward, and pressing the plug deeper and deeper into my ass. It felt great. Each time I worked it in a little deeper, it stretched me wider. Initially it was painful, and the pain replaced the pleasure I had been feeling. But after a while in the same position the pleasure would overtake the pain. When it was all pleasure I would work it in a little more. And so on.

I was a man on a mission, on a mission to get fucked by the biggest cock I had ever seen! Soon enough I was grinding my ass onto the plug, letting it fuck me, and each time I was pushing it in further. Leroy was amazed at the progress I was making, but I still had the widest part to go, and progress had slowed almost to a stand still. It was about 50/50 pleasure/pain at this stage. I felt really stretched, but really turned on by the whole situation, which encouraged me to keep going.

Leroy took an unmarked exit off the main road, onto some sort of dirt track, explaining that this took us up to his cabin. As we went on, the road got darker and narrower. And bumpier. Pretty soon the bumps were getting quite big. By now I had pretty much all my weight on the plug. It felt great, but it wasn't going in any more. I was enjoying it too much to worry about what that would mean later on.

I soon realised there might not be a problem. With every big bump I would be thrown into the air a little, and come down hard on the plug with a big grunt and moan. It was amazing, with the help of the car, the plug was fucking itself into me. There was no more pain, it was all pleasure. With one final massive pot hole, the plug literally nearly split me in two. It was fully in, all my weight was equally on my ass cheeks & the plug was stretching wider than I would have thought possible. Leroy looked over and realised I had got it all in, I was sitting there writhing on the plug, grinding it into me, moving gently forward and backward, with the road helping it to fuck me. I had a triumphant face on myself. Leroy's face had changed too. He looked like the horniest man alive, he was dripping precum by the cap full, and looked like he was in a trance.

He pulled into his drive.