Relax your sphincter like your pooping

lube helps, but the best trick is an enema. I won't go into details here why, but it makes more of a difference than anything else

Use lots of lube , make sure you are warmed up before starting anal

Try anal solo, that way you can get to know the feeling of being butt fucked...plus buy a butt plug x

Stop doing that do you want hemorrhoids? That's a good way to get them.

Make them take it slow also a dildo with alot of lube when i fuck my girls ass i let her on top and she does the work so not to get hurt by the time she starts cumming she is slamminf all the way

Try sticking your fingers up there , then when thats no pain , try a brush handle , make the object bigger and bigger and soon you'll be taking Dick like a pornstar