Dean did tend to let his hands wander, and Hanna had seemed to enjoy it, so that was easy to replicate. They were thinking along the same lines, which was good. He still didn't quite know what to really expect out of this, but he would teach her what she wanted to know, there wasn't much to it, as he had very few reservations about where hands ended up.

Draining the last measure of his whiskey, Dean reached for her wine glass and leaned to set it aside on the table. He turned himself to face her more fully and scooched closer, reaching out to take her hands and settle them on his shoulders, "Safe bet, fine in the beginning." He chuckled, guiding them under the open collar of his shirt. "Much better, always find a little skin." He had always had little patience for the barrier of clothes once things got moving, but since they weren't going anywhere tonight, this was a good start.

Letting his own hand fall to her leg again, Dean didn't move any skirts out of the way like he normally would, but he did travel up her thigh to her waist. "Don't be afraid to lean into it." He mumbled as he closed the gap between them.