I've heard it can be a little easier if you have a bowel movement earlier in the day that you're going to try anal. Practice makes perfect!

Lube - lots of lube. Tell him you respect the fact that he wants to have anal, but he needs to respect that without lots of lube he will not be having any anal. Also, tell him he needs to work it in there slowly, he can't just shove it in.

Amen sister imw yes lots of lube. It helps to push out while hes entering clenching causes unneccessary discomfort (not from experience) a high level of arousal enlivens the posterior cave, making it much more receptive to touch. Keep up the genital caresses during anal it comforts and distracts . . . . . It may take hours weeks or months for the shy & tender rear to relax and blossom fully just tell him to be patient

The biggest key to anal sex is to relax. Try not to think about it and tense up. Thats when it hurts. Remember to use lots and lot and lots of lube. U can't use to much. At first it will be extremely uncomforatable and feel like u need to have a bowel movement but the more times u do it the better it will feel. Depending on which angle he is in u matters to, so try it in differnt positions and try fingering urself during it and u'll forget he's even in there :wink: . Good luck on ur new discovery.