advice in anal

KH
Hey guys, so - I've been with my boyfriend for over a year and a half. I always joke with him that I'm a little interested in trying anal, in which he just laughs it off with me. A lot more recently, while having sex, he will touch my butthole, or stick a finger in it, or will brush his dick on it. It tickles a lot, and I'd love to try it for the first time.
He always says how gross it is, coming from the butt, but since he does those things to me without my asking, it seems he's a little interested too!
I'd like to know what works for you guys, when you did it for the first time, and how it felt, and that next time we have sex, I should have a ton of lube on hand? 😬 we are 21 and 24. Xoxo