Every other time we've done this, it's not been with any sort of goal in mind. At least not beyond what we were already doing at the time. Jack would just sneak his hand under my shorts and nudge at my hole, then ask if it was okay. Every time. Even after he'd added some lube, our positions were always different from this one, usually with me straddling Jack's lap or lying on top of him.

Never like this. And never in preparation for something more.

And it's not like I don't know anything about anal sex. I'm a gay man with an internet connection; I knew all sorts of things long before I probably should have. So I know just exactly what he's hit when his finger crooks inside me and a white-hot shot of pleasure rockets up my spine.

That doesn't means I'm not surprised.

"Oh--! Jack." It leaves me shaking for a moment, unable to do anything at all and then I roll my hips back, stupidly eager for more as I grip the sheets. "Please-- God, please. Please do that again."