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Originally Posted by
eversonpoe
are you warming up with small toys/fingers beforehand? are you using an appropriate amount of lube? (don't use ANAL LUBE of any kind, because it has numbing agents in it, which are a really bad idea...if it hurts, you're supposed to stop)
basically, you need to warm up/stretch yourself out a little bit so that you're ready to take him. i recommend a tapered buttplug of a decent size, because it will allow you to slowly push it in a little bit at a time, stretching yourself out while you're doing it. maybe start by getting that in you and keeping it there while you have vaginal sex, and then keep trying until you can do proper anal.
good luck and don't hurt yourself!