"I'm sure...it's going to hurt a little, just like your first time did, but I'm okay with some pain." Now, Tony was just intentionally rubbing his ass against Steve hard, almost like they'd have been fucking were it not for clothing. "Unless you're just too unsure, because I'm more than happy to bend you over." He didn't want to make Steve uncomfortable with this, and if he just wasn't feeling it, Tony would be okay with it.