Try orajel, you know for your teeth. It is the same ingredient as anal lube only a little stronger. It has no side effects. Just make sure to wipe off the excess or he will go numb.

i belive it does, but not because your butt gets used to it but the experience of how to make it more enjoyable. heres a few tips i've picked up: 1. to much lube is not enough 2. she has to be extremely turned on just begging for you(lots and lots of foreplay) 3. take it very very slow when initialy inserting, just basically hold pressure against it and it should slowly begin to take it in eventualy 4. try the missionary position so the muscles are relaxed doggy style tightens the anus muscles making hard and painful to insert

The first few times it is going to hurt but it will hurt less and less each time you do it and then begin to feel good I know several girls that prefer sex that way

First of all: GFE! Second: Your anus is not a naturally lubricated orifice like your vagina. You absolutely NEED lube. If your boyfriend is worried that he'll get funny looks if he buys it, then you'll need to do it. (Get payback by making him buy you tampons sometime if you feel the need.) Get something water-based - Astroglide and KY come recommended. Third: It may still be sort of uncomfortable. The muscles down there are used to things going out, not things going in, which means relaxation and foreplay are going to be important. Usually, a well-lubricated finger or toy should be the first thing that goes in, not his penis, to help the muscles relax and adjust. If, for some reason, you choose to bypass that step, you'll need to go slowly. The first time, it may take 20-30 minutes for him to get his penis all the way inside you. Last: Do some research. The interwebs know all, but here are a few good how-tos to get you started (also, they discuss the nastier details that I have not): - http://www.associatedcontent.com/article/31814/a_beginners_guide_to_anal_sex.html?cat=7 (If you don't read any other link, READ THIS. Both of you.) - http://www.analsexyes.com/prepared.shtml - http://www.babeland.com/sexinfo/howto/bend_over_boyfriend (More oriented towards pegging, but still has a lot of good advice.) - http://www.analsexyes.com/reader_women.shtml (Advice from women) - http://www.askmen.com/dating/vanessa/28_love_secrets.html (Even more advice about women, aimed at men. Perhaps your boyfriend should read this.) TL;DR: You need two things for anal sex to work - PATIENCE and LUBRICATION.

i agree with all others on the lubrication. lots and lots of it. and forplay as well. but something that helps me get into it is a little help with a small vibrator. that can get you going real fast and even make you WANT to take him anally if hes fingering you there. trust me it works and relax.