Go. Slowly.

Agreed, go slowly, breathe and relax. And if you drink, try wine. Wine helped me relax just enough that it felt so good.

SLOWLYYYYYYY! also they make a lube with benzocaine in it (marketed under Anal-eze, and another one called "tush push") that worked for me. about fifteen minutes BEFORE trying, use a lot of the benzocaine lube...... on yourself..... then continue with foreplay, fingers, toys, whatever...... then add astroglide mixed with KY to HIM, and more on you........ and proceed with caution. If you think you have enough lube, you probably dont. if you think "oh crap this is going to make a mess" you have enough.

Slow is the key. I read somewhere online (before we tried it) that this helps. And it really did for me. Try putting a bit in like just the head then pull it out a little but not all, then go in a little farther (very slowly), then out a bit again and keep doing this till you can comfortably put it all in. I second the wine suggestion, or anything with alcohol.

I love anal. We never use anything and it feels amazing. Like everyone said, take it slow. Once he's all the way in, it is the best feeling in the world.

Eat light all day. Empty your bowels beforehand. And all the other suggestions above.

I've read using numbing lube is bad because you can't feel if you're being torn, or hurt. I wouldn't recommend. Just go really slow and give YOURSELF all the power, if you're not comfortable, just try again later.

I always find that my wetness makes the best lube. Try cumming first, so you're relaxed and lubricated before you try anal.

Follow the indications above, the wine really helps. One thing I can suggest that works for us, we use lamb skin condoms. It feels good for him & for me, plus you don't have to worry about getting messy. It also helps if you find a position that you are comfortable with. I prefer spooning. It's much easier on you and you control the movement, not him. Plus he gets to see your face! Try it, hope this helps!! Have fun!!!

I agree with the other posts: empty your bowels, use some lubercation, and starting on your side slowly. As he goes in slowly, tell him if it hurts just stay still but dont get out. It seems to hurt more when he does that. Alcohol does seem to ease your tension but dont use to much so that you can stay in control. Just have fun with it - it can be amazing.

RELAX! The lube we use is Gun Oil...it's really slippery, & feels great. I like LOTS of lube, and he lets me run the show. Once it's in, it feels fantastic!!!