HI PART TIME HOMOSEXUAL FULL TIME BI GUY HERE FOR UNSOLICITED ADVICE: Anal douching and stretching is a fucking must. I have only done anal spur of the moment once and never again. Your first experience is pretty much most peoples dude. It is super embarrassing but we all get over it eventually.

If you wanna do it again i would buy a douche and learn how to use it, plan ahead cause its not quick prep like putting on a condom. You wanna prepare like a good hour and a half before going down the dirt road and have a towel to hand just in case.

Also warming up is super important. I know its not what were talking about but in terms of comfort its a game changer. Your sphincter is a one way system so isnt expecting traffic going the other way. Easing everyone into their new role is guaranteed to make sure everyone has a good time. Good luck compadre.