Okay...I've about fucking had it with these people on the internet who, when talking about anal sex for the first time (for either gender) say something like this:
It'll hurt the first time no matter what because that is virgin territory. Don't let that turn you off because the second or third time will be fucking amazing.
Well...props for realizing that anal sex can be amazing. But from there this statement is complete and utter bullshit.
If anal sex hurts you are doing it wrong.
Either you are going too fast, using something too large, not using enough lube or a combination of these factors. On rare occasions there may be hemorrhoids which will make anal penetration painful. But barring that issue, anal sex should not hurt.
Here's what I think. The people that say this are too fucking lazy to take the sometimes considerable time required to ease into pain-free anal sex. Again this matches up with my theory of why so many women don't like anal - because they have been on the receiving end of bad anal sex. Because some guy didn't take the time to do it right. Sometimes through ignorance. Sometimes through laziness. Or both.
So when women strap on a dildo, their example of bad receiving perpetuates itself and then we have a shitload of people who think that anal sex has to hurt the first time! Not. True.
Warm-up for an ass isn't 2 minutes of fingers, people!!!! Warm-up for an ass can be 1/2 hour or even repeated sessions over a few days using consecutively larger toys.
You cannot treat the ass like a vagina!
Anal sex requires patience.
Anal sex done correctly is indeed pain-free.