Any tips for anal sex ?

My first attempt with anal sex was a fail. It was in a train & no lubricant.... I don't think I need to explain that any further... lol

My second time I was okay but then again I was kinda tipsy

My 3rd time I didn't like it felt weird or not really enjoyable

My 4th & last try it actually kinda hurt ... so from there I just gave up on it .

I want to be able to enjoy it & I am open to trying it again with my new partner. I did say I would be down but there has to be lubricant.

P.s i love buttplugs but don't own one because I'm honestly scared, a little embarrassed because the body does the most embarrassing things at the most not right moment 😂

Anyways tips suggestions questions comments ? Anything literally .