Anal sex need help

ok me and my jamie uh boyfriend, ex, whatever he is. well we have tryied anal before because he wanted to so I figured I would try it. that was maybe 3 months ago or so. it was painful as crap and he only went maybe 2 inches in and I had to call it quits. but now he keeps asking to do it again like every night and has been asking for like a month now, and im afriad to try it again due to the pain I experienced last time and he doesnt understand that. and I kinda want to do it because it will make him happy. everytime I think I can do it and im like ok I can try I always get a stomach ache or heartburn every time. and I think hes getting agervatted because im to scared to try it. I have done told him that im scared of the pain and if there wasnt any I would do. but im confused and need help on this. and I heard if its done the right way it wont hurt and stuff. so someone please help. what should I do.

well use a comdom and lots of lubericant then it should be a lot less painful

okay I had your same problem and the thing that helped me was he got me all hot and horny then he started fingering me to relax me then we used KY jelly to lube up and since I was being fingered at the same time I was relaxed and to was my ass so it went in smoother and it didnt hurt that bad try it this might help

Please be nice to your ass!!!! It hurts because you are neither relaxed nor well lubricated. It's normal to feel a bit of pain but if it's really painful then you're doing it wrong! First, if you're doing it just to please him then you aren't doing it for the right reasons. You have truly want to have anal sex in order to get through the multiple hurdles of not being used to having something go in there. Second, he is too much in a hurry to really care about you and your health. He has to learn to slow down. You can't just go and stick things in there without a little practice and patience. Not to mention he can seriously harm you if he isn't careful and loving! If you are both truly ready for anal sex then take the time that is needed to learn about it and get your body used to it. If he doesn't get it, then try sticking something up his ass and see how he feels! But seriously, the best way to practice anal sex is by slowly getting your rectum used to having stuff in there. Start small, use lubricant like K-Y jelly and buy some toys like butt plugs (or just plain fingers). Concentrate of being highly aroused and practice lots of foreplay and touching (tongues are always good!) And last but not least, keep your arousal up during penetration by playing with your clitorus. Make sure he understands that he has to listen to you and if you tell him to stop he has to stop. Insist on him going slowly and take your time. Oh! And need I mention to use protection because anal sex is the fastest and easiest way to get STDs and HIV~AIDS! Good luck!

thanks for the advice yall, and I have tried all that but I got tired and went to sleep so I think I lead him on. and I feel bad for it and he gets mad because of it and I dont know how to make him understand o wi feel because I have told him so many times but he doesnt get it.

and not to mention hes like 81/2 inces and maybe 2 inches think I think I dunno so it might hurt more right?