I thought so. I don't know, either. He seems to be the most relaxed person here. I might have sounded a little condescending - "I would have thought you would have realised this. Given you have been here for so long." : / Sorry, Glen
Your first mistake is that you tried to put your dick in there first, that's why it hurts. The first thing you need to stick in there needs to be soft, I recommend your tongue. The key to the backdoor is your tongue, if you get her ass nice and relaxed with some analingus then you can move to fingers or a small butt plug if you have one. If you're too squeamish to lick her ass then don't fuck it. U gotta lick it before you stick it, that's my rule. Once her ass is nice and relaxed from analingus and fingering then you can attempt to use your dick, but go SLOWLY. I recommend her on top in reverse cowgirl so she can control the speed and depth of penetration, plus it just looks awesome to watch your dick split her ass open in that position. Remember to use lots and lots of lube. Have fun tearing that ass up, Ace