Tried anal once in the past and it was a nightmare. Any advice on how to do it right so it doesn't feel like a freight train in my ass?

I tried anal once a long time ago, and he just managed to push it all the way in one time, and I think I cried for about 5 minutes afterward, and it ruined the experience. Since then, I have not fully tried it because I'm so terrified of tearing my ass in half. But I am certainly Interested, and my SO is as well... and i do enjoy finger play... Any advice?


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