There's no doubt that their shitty histories were a great part of what drew them together; so call that a silver lining, if you will. Maybe that's romantic or optimistic or something good; he thinks it doesn't matter. The only what ifs that matter are the ones ahead, cautious experiments rather than wistful fantasies. This moment, this whatever they are, it might not make up for all the dark times but maybe it makes it worth going on in spite of them. It makes him comfortable enough with her to let his guard down.

Once the boots are gone he spares a moment to glance up at her, wearing a trace of a smile, offering a chance to voice a protest if she wants, glad when she doesn't. One good turn deserves another and he's anything but shy, all willingness and wanting, eager to please. If she asked, he'd stop. It's about the only thing that would stop him, though.

The way she moves with him, shifting her hips so he can drag her clothes down over them, is patent encouragement; and he leans in to kiss her thighs as he bares them (though really, he's more blindly mouthing at her skin, too eager to be demure himself). It's a slow progression, not from hesitance but because it's the right pace for the moment, as he works his way down to the bend of her knee, leaving her pants in an unceremonious heap on the floor between them. There he pauses to meet her eyes again and wet his lips before he leans back in to meander his way back up her leg.