Talk to your partner about the prospect. Also, the "accidentally-slipping-it-in" move is an asshole thing to do. You can cause serious damage by pulling a stunt like that. Considering the nightmare that can come out of there after a night at a Mexican buffet, I can see how people would think that. It makes clean-up that much easier. Oh, and stay the away from KY Jelly — that stuff is about a 4 where the average rectal PH is about a 6.
A little preparation will help a lot. One of the common misconceptions is that anal sex will hurt, weaken or damage the anal muscles. People have enjoyed anal sex for many years without ever causing damage. The way they do that is by never going further than what feels good. You can do something else on those occasions and have anal sex another time. There are a few different reasons why anal sex might not feel good.
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Of all the sex acts out there you can try, anal sex comes with some of the most vicious rumors. I don't just mean the rumor that everyone said Stephanie from high school was doing it, or the weird, creeping thought that all your friends are secretly doing it behind your back pun intended. I mean the rumor that it's always painful, but if you want to try it, you just sort of have to put up with it and dive into butt stuff, head- or I guess ass- first. And then you just deal with all the insane injuries that happen later. Some good news though.