When I get back to school, me and my GF are gonna get into anal. I'm fairly large, and haven't fucked a girl in the ass in years, so I don't want to just dive right in. My current lady is pretty nervous about it. Also, she's super-excited to fuck me in the ass with something. I've gotten a finger in there, but have never ventured further. Any suggestions on how to make this the most pleasurable, and non anal-leakage-y experience possible?