I'm a M21 and have always had a terrible experience with bottoming. Insertion is always incredibly painful and I so desperately want to enjoy anal sex. I've tried training my anus with just my fingers, but it's still impossible to get anything in there – even with lube. I've had anal sex at least ten times and 95% of those instances have been uncomfortable and/or painful. I'd greatly appreciate any advice, thanks
EDIT: thank you everyone for the insight and sharing your experiences ❤️