how have you warmed up your sig other to anal (both ways)

by both ways, i mean him fucking me in the ass and him allowing me to play with his ass (finger, small dildo, maybe eventually being allowed to peg him). a few years ago, a bf let me peg him and it was amazing and i want to do it again.

we've already talked about him in my ass, he says he's done anal a couple of times, and he'd be up for it, although i did feel his tone of voice was very slightly apprehensive at the time. lube and a condom are the rules for both of us. i absolutely love it, and the day he's in my ass for the first time he'll be peeling me off the ceiling after, lol. we haven't talked yet about me playing with his ass, but we are pretty open about talking about sex and what turns us on, and i am not ashamed or feel anything we've done or talked about is 'dirty', so i wouldn't have any issue asking him if he'd enjoy it.

so guys, how do you go about initiating usually?

and girls, how do you initiate playing with your man's ass?

i already have some ideas on how to get things started, but would love to hear others opinions!

 

I like to lube it up and fist it first, lol!