anal sex

So I've been dating this guy for a few months now and we are getting more serious and lately he's been talking about doing anal sex a lot. A couple of weeks ago when we were fooling around he used his thumb and kinda played with my butthole and it kinda felt weird cuz I never had someone play with my butthole before. I tried anal once with an ex but never let him put it all the way in because it hurt so bad. I told this guy that for me to even think about doing anal we have to be with eachother for at least a year. But for some reason with this guy being around him makes me want to try it with him and be freaky. Should I try it or should I just wait it out?