Ok this might be weird advice with a better way.

So I was with an ex one time that was absolutely obsessed with the idea of anal. I straight up told him “If you can take my dildo all the way, I’ll try,” and he did. I was already kind of not into him anymore before that happened, but pushing a dildo into his ass fucking ruuuiiiined it. So it never happened. I ended up bitching out, and couldn’t come back from that. Broke up.

Next guy had a way smaller dick (prime for this). We bought one of those smaller to gradually bigger ball portion plugs. On a night I felt ok, didn’t have stomach issues etc... I got high asf. Went into the shower with that plug thing. Soaped it up and slowly went at stretching myself out. Once I finally dealt with all that... I went back out into the room all cute in lingerie, smoked a fuck ton more weed and went at it. Keep in mind, small dick... Worked wonders. Over time I ended up enjoying it, and didn’t have to do more than “deeply” shower.

For my now relationship. OH GIRL! I need to be drunk asf (large dick) and I want to be destroyed. The pain becomes pleasure and anal is my love language, saved for only my LTR.