no such thing as too much lube. seriously. just fucking lather it on
you have to be super relaxed, and that means relaxing your ass muscles. if you're not into it and you're tense, it will hurt like hell. if you're into it and you can relax, it will be fine
your first time will probably be kinda crappy regardless just because you have no idea what you're doing and you're tense because of first-time nerves - it will probably hurt when it goes in, but this will stop after a couple seconds if you can relax
for me it was only the third or fourth time bottoming that i really got the hang of it and started enjoying it, and that's pretty common, so don't worry if it's not so great
I don't find douching to be THAT necessary. Just don't bang after taco tuesday, stick some fingers up there beforehand, make sure you're clean and such. Poop isn't stored in the rectum, and cmon you're having buttsex, sometimes things are going to get dirty and there's no avoiding it. Get over it. Use a condom if you're not virgins and stuff.
Also like the other dude said, stretch a bit first, let him slide in, don't move too much for a few moments, let yourself get accustomed to it and go at your own pace. My first time wasn't that enjoyable, but since then it's been nothing but amazinggg
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