Quoting Kotie Anglemyer:" Ok so i know this may be a weird question but my SO is really into wanting to try anal sex... i am terrified ... [snip!] ... question is how do you get to become comfortable with it or even getting the courage to attempt it What makes it not hurt?"
lots of lube.. and try it with him being on top... basically like missionary just the other hole.. it hurts less like that.. and honestly the more aroused you are the less its guna hurt.. But when it first goes it it hurts really bad for about 30 seconds.. then it goes away.. So if anything make him go in really slow... and when that terrible pain comes make him get out and wait till it stops hurting.. after that he should be fine to get back in.. Lmao. Dont mean to sound like an expert or anything but Ive done it a few times hahaha