He'd been ready for her to stop him, or to at least resign herself to the thing, frozen and not participating. Sweeney certainly hadn't prepared for her eagerness. Her kisses are welcome and answered in kind, though he has to be mindful to not twist too far over her, so he doesn't lose his balance. He has every intention to keep his hand where it is for a while longer.

Long strokes continue, reined tightly in control, lest he run off too roughly. That said, eventually, he parts from her just enough to get her in focus. His hand stills long enough for him to dip the tip of his finger into her. Not much, just so he can trace the ring of flesh while he studies her face for signs of discomfort. Or pleasure. Sweeney's guessing the former is more likely.

"Hurt? Still?"

Sweeney would like to fuck her, but if his finger is unpleasant, there's no way he's fitting his cock in without more tears.