“For people who are interested in or enjoy anal: ‘It’s going to hurt regardless, that’s part of the fun.’ Yeah, that’s bullshit. First, you need to be using the thickest lube you can find, ideally water-based. Vaseline, soap, spit, etc, is not going to cut it, no matter what porn/idiots say. Second, make sure that you are applying a generous amount to whatever is going up there. Third, if it hurts, STOP immediately as this can lead to tearing or other issues that could require medical attention.”
“In short, it shouldn’t hurt. Ever. I should have clarified: silicone-based lube is perfectly fine, it’s just very messy and difficult to clean up. At the end of the day, however, it’s up to you and your partner(s) to determine what’s best!
Also, I’ve included a link explaining why anal sex should never be painful.”