Also, be prepared for her to possibly feel uncomfortable and to feel like she has to go to the bathroom. My experience has been that way, even with a finger, that I feel like I need to have a bowel movement.

Hi UHCougar:

I think you'll find that one of our GREAT moderators will post a link here and point u to a complete overview of how to prepare for and have anal sex!

In direct answer to your questions:
Condom: YES YES YES! Anal sex is still sex, so yes, wear a condom.
Lubrication: YES YES YES YES! There is no natural lubrication where u 2 are going, so you need to get some lube. You can buy KY, and many other forms of lube where u buy your condoms (most drugstore family planning sections have a good selection of lube)

Other things to keep in mind:
1) GO SLOW! You'll need to use your finger or a dildo on her ass before you try to put yoru cock in her ass! Remember, the sphinter is a muscle, so you have to relax it. Plus, it's good foreplay.
2) Let her play with your ass too! When you feel what it's like to have something in your ass, you'll have an appreciation for what you're asking her to do! Plus, it feels great.
3) If you can get her comfortable and relaxed, use A liberal amount of lube on your cock and her sphinter.....and go slow..let her ass adjust to your cock.
4) Let her set the pace: I've found that 1st time anal sex is best done with the guy on his back and let HER lower herself on your cock. That way she can set the pace and get comfortable.
5) Touch her all over and reassure her: Dn't make this all about you f***ing her ass! Kiss her, stroke her, play with her clitoris and breasts - this will make the whole experiment much more pleasureable!

Remember, MEN have a prostate and thats what makes anal sex so hot for men when they get fucked in the ass. Women do not have a prostate, and there are almost NO nerve endings (pleasure nerve endings) in the rectum.

Hope this helps!

ps: there's always a chance that if you do enter her ass, you may find yourself with "shit" on your condom. Thats not uncommon.....and if so, y ou're better off stopping then going on....from a pain and cleanliness perspective, you don't want any of that to get into her vagina.

Well I would advise a condom. Keeps the bacteria out.
Lube, very very very very important. Get something like anal ease or Astroglide. I know you can get Astroglide at your local walmart or drug store.

Start with a finger, work that around, then work up to two or three and stretch her out.

I just advise you to go slow and listen to her if she's having problems with it.
I was eager myself to try it for the first time and the first time, we didn't really have any problems. There was some pain but not a lot and it felt somewhat good.
However, this past time, it hurt like hell and I know that it's not something I want to try again, not anytime soon at least.
So, case in point, just cause it may work one time, doesn't mean it will work the next.