Yeah, Cas is kind of in the middle ground when it comes to a sexual history xD He's not completely inept because he's had short-term girlfriends before, but he's never gotten further than making out with them, so he always short circuits a little when he thinks about doing more than that.
Yay xD I enjoy writing out his awkward slip ups haha. He's decent at being smooth, but he still messes up when he gets impulsive