This Sort of Thing

"You're sure you've done this sort of thing before?" he asked me. I was naked on his bed; he was shirtless and sweating from working outside. "I don't want to hurt you."

"Yes, a million times." An exaggeration. Not a million. Probably not even a hundred. And never like this.

"Little lady, I don't think it's a million. I haven't done it a million times, and I've got a good few years on you." Still, he wasn't kicking me out. "You know I'm only interested in one thing," he said after a moment sizing me up, as if he were trying to convince me that it was a bad idea.

"Yes. I'm only interested in that too." I waggled my ass invitingly. "Come on, you know you want to."

He took a bit of further convincing which I'll gloss over, and then he took a few more minutes to get ready, but after what seemed like an eternity, during which I stroked my wet slit hungrily, he was naked in the bed with me. We didn't kiss, and he rebuffed my attempts to touch him. "Only one thing, little lady," he said again, like a warning, although it wasn't stern. Just a reminder.

His cock was as huge as always, and I suffered a moment of self-doubt; was this really a good idea? Sure, I had done this before, but that was all kids stuff compared to this. Would it work? Would he try and I'd just be too tight? I couldn't bear the thought of failure. "Do you think... you could maybe loosen me up a little... before..." I said hesitantly, dreading his response.

He laughed, not a cruel laugh but a kind one. "Little lady, if I don't loosen you up a bit, this ain't gonna happen," he said, still smiling. And he gave me a kiss on the cheek, not sexual, just reassuring. "You think you're the first tight thing I've fucked? Give me some credit. I know I'm ancient now, but back in the day I was very attractive."

He was kidding me now, and I laughed too, a little nervously but mostly relieved. "You're very attractive now," I said, and as I said the last word, I felt his thumb press against my asshole, running around the outside and then popping in. I grunted in spite of myself.

"Now you're just humoring me," he said, patting my butt with his other hand as his thumb probed deeper, his fingers resting on my pubis, not stroking, just sitting there. "I remember my first time like it was yesterday though. Not as pretty as you. I wasn't terribly discriminating when I was young. But tight like you wouldn't believe. I didn't prepare, and it wasn't pleasant, but we got through it." His thumb was completely inside my ass now, the palm of his hand resting on the space between asshole and pussy, fingers tapping lightly just above my clit.

"If it wasn't pleasant, why did you do it?" I was a bit breathless.

His thumb withdrew, and with it the feeling of depth, and I almost sighed with the loss until I felt two fingers probing my butt now; no, it was two thumbs, both left and right, his other hand resting above my ass now. "I wanted to prove something," he said as he widened my anus with his thumbs. It was different than being fingered, like I was being spread in a dimension I hadn't known existed before. There were twinges of pain, but if I flinched he relaxed the pressure for a moment. "Not a good reason. Much better to do it for love, or even pleasure. But I was looking to prove something, to myself, to the world, I don't know." He sighed, and the pressure of his thumbs relaxed slightly. "Hell, I should have never brought it up. We ain't here to psychoanalyze. Let's just say that I've learned from experience that you can't just go fucking away at a tight hole with no howdyedo." And then he spun his hands so they were resting on each cheek, the pressure suddenly coming from a completely different angle now. I gasped. "Like that? You've done this before, but I'm pretty good at it." He laughed again.

I could feel the muscles accommodating the pressure, and once I felt comfortable enough, I said, "I think I'm ready. Do I feel ready to you?"

"Just hungry to get to the good part," he said with a smile. Then he spit, the glob of saliva landing on my tailbone and drooling down into my ass. "Sorry, old habits," he said, withdrawing his thumbs. "We're plenty lubed up already. Don't worry about that, it's just my way." I liked knowing that I was getting the full treatment, liked knowing it was just his way, and I was still thinking about that when I felt the head of his cock press into my ass. It was large, larger than I expected, and I must have shuddered or clenched, because his hand was on my back, holding me in position, and he said, "Relax. Just relax." Maybe that was his way too.

A big cock won't save a bad lover, but there is something about a big cock, particularly being pressed up your butt, that can't be duplicated by a small one. In the hands of experience, the hands of skill, it's like it's inescapable. You know it's coming, you feel the strain as it slowly spreads you apart, but you don't want it to stop, even if it gets uncomfortable. As the shaft grows inside you, slowly but surely, you can't think, you just react. Your body is against you, and you have to strain to relax, which seems like an oxymoron; a tense relaxation. Some people don't like it, and that's fine, but some people do, and I'm one of them. It's perhaps an acquired taste, which is why I wouldn't recommend going with a monster your first time, but eventually, it just feels right as it feels wrong.

He stopped talking once he penetrated me, retreating back into the taciturn nature to which I was accustomed. The first thrust, in slow motion, he didn't try to bottom out; he got as far as seemed wise and held there, feeling my ass spasm on him. And he hadn't lied; he was only interested in one thing. His hands held me in place, but did nothing more, so after a while I reached back and began to stroke my dripping pussy, pace in the bed, panting as he pulled slowly out again, all the way out, then spit directly into my ass this time and pressed back in, a bit harder and a bit farther. He was never in a rush, he was never rough, but he didn't hesitate, even at the moments when it seemed like I was going to split in two.

He didn't seem to notice when I came the first time; it was a weak orgasm because my muscles were straining to contain him. Once I came, though, the pressure released and he was able to work up to the hilt, his balls bobbing against my fingers as they worked on my cunt almost as if on autopilot. He was no longer pulling all the way out, and he was moving more quickly now, small thrusts, withdrawing slightly and then burying himself again in my ass. And I was feeling better about him now, no longer straining, just the slight sensation from taut muscles that perhaps they'd prefer if I weren't taking a giant cock up my ass. I wondered for a moment if he'd switch over to my cunt, where the feelings would be more intense, more pronounced, more enjoyable. But I didn't say anything other than gasps and moans, my face in the blankets.

In the end, I came again, and he noticed this time and seemed to pick up steam. Perhaps that was also his way. It hadn't been long, comparatively speaking; I know he can go for much longer if he wants. But he picked up the tempo as he felt my spasms, and soon he was running almost the full length of his shaft in and out, just the head remaining inside. He popped out once and just pressed back in, an accident but a pleasant one. And then he grunted, "I'm going to fill that ass up," and pressed in, and I could feel the tension in the way he gripped my hips and the hardness of his cock in me, and then he groaned, a loud animal noise, and I knew he was doing as he'd promised. I didn't feel it; I was too overstimulated to feel it as he came into me. But I knew he was.

His cock softened as soon as he'd shot the force of his orgasm, and slipped out of me, and I felt the jizz run down my leg, watery and insubstantial. He'd tried for me. He'd had to work at it. I felt ashamed, in that moment, that I'd asked him, almost forced him, when clearly he would rather not have. I rolled over to look at him. He was smiling. "Little lady, I haven't had an ass that tight in a long while," he said. "Thanks. I might just get my strength back and do it again. There's something to be said for variety." Then he saw my face and frowned. "Did I hurt you? You want to..."

"No, I just thought you didn't like it, that you were forcing yourself."

"Not at all, little lady, not at all," he said, patting my thigh with his big hand. "I said I only wanted one thing, and I got that in spades. You just lie back and feel good. That ass of yours is a treasure."