Go-To Girl assumes that when normal people have dinner parties they don't sit around the table with their closest friends explaining how to successfully have anal sex. But, hey, anything for you guys!
Ethically speaking I have to say that I learned (almost) everything I know from Tristan Taormino, author of The Ultimate Guide to Anal Sex for Women.
While I have written several times about anal sex in this column, my readers (read: dinner party guests) are begging for an explicit and authoritative account of the 10 Steps. So, here goes.
1. Buy a bottle of lube.
2. Put it under your pillow.
3. When going down on your partner covertly lube up a finger. (9 times out of 10 the friend-cum-reader who's asking is male with a female partner, but the same applies if it's some other combination of partners or a female partner who wants to peg her man)
4. Touch the rosebud lightly; eventually you should be able to feel it relax and it will open up slightly.
5. Put your fingertip in. Delicately!
6. Assuming your partner doesn't say, "What the fuck are you doing?"* bring them to orgasm with your finger in their ass.
7. Snuggle and whatever and say something like, "That was so hot." Hopefully they'll agree and say something like, "I don't know if this sounds weird, but that felt soooo good!"
8. Repeat steps 3-7 until you can comfortably get 3 fingers in. This will probably take a few days.
9. When you and your partner have decided that you're ready to go forward with a cock-in-ass situation, warm up first with some fingerplay. Add more lube!
10. Covering your cock (flesh or silicone) with a ridiculous amount of lube (you should put on so much lube that you think, "Surely no one could ever need this much lube." And then add more.) go forth and fuck appropriately.
While not mandatory if you and your partner are STI-free, condoms are a good idea for health reasons and because...well...what goes up must go down. Keep that in mind.
Do NOT use baby oil or any other oil-based lube. Or flavored lube. I like Maximus.
My dinner party guests were not in agreement about whether or not one should mention anal curiosity beforehand; I think, honestly, that once you get to be a certain age it's okay to try certain things without asking. Obviously "No" means "No," but your chances of success are better if you finger first and get told "No" (or, hopefully, "Yes!Yes!YES!!!") later.
*If this happens, you might be shit out of luck.