First time. Anal sex

K_17

Been with my bf over 2yrs. Before he thought it was kinda gross but now he wants to try it. I get really nervous very easily especially when trying new things. We don't have sex often and when we do it's really painful even with lost of foreplay and a shit ton of lube and him going super slow and I tend to tense up. I'm scared doing anal is gonna hurt a lot worse then regular sex. I'm down to try it but I need advice. What do you do to ease into it? What helps u not be in so much pain? Best positions for first time? Recommend butt plugs to start out? ANY advice is appreciated