I'm gay here, but same principles apply -

1) A good idea. I always keep moistened and dry washcloths (come in handy no matter what kind of sex you're having).

2) Depends entirely on her system. If she bathes beforehand and cleaned back there it shouldn't be a big deal. As a receiver I get a bit fastidious about it and do an anal wash out before engaging, but it's not usually required.

3) If you mean by "round 2" any sort of genital/oral or vaginal contact, YES to soap and water BIGTIME!! If you're just taking a few minute break and then going back for more of the same, not so much. But it's always better to error on the side of cleanliness.

4) If you've read all the other threads on anal here I can't imagine there's much to add. Since she's already done it and likes it she'll no doubt be able to guide you a bit on how quickly to enter, best position for her, blah blah blah . . .

Have fun! :)

Additionally,
1- You need to protect yourself from a potential infection through the use of condoms; always wash or shower after with soap & water, as well as viod to clear out the urethra.
2-Never engage in anal then go to vaginal, cross contamination will cause her a nasty infection.
3-Remember any semen which leaks from the condom or anal area can come in contact with vaginal fluids resulting in a pregnancy, she still needs to use birth control.

> 1) Is there anything special I need in the bed...like should I keep a towel or wet wipes on hand to clean off my fingers?

First things, first. The person on the receiving end should have gone to the bathroom sometime beforehand in order to empty the rectum.

Second thing: bathing beforehand is a good thing.

Sanitary wipes are a good idea, as is a wet washcloth as an alternative.

> 2) How raunchy of a smell should I be prepared for?

That depends upon whether the person passes gas as a result, or, you just pick up matter on your finger as a result of being in there. Certainly by now you should be able to answer the second from personal experience.

> 3) Is wiping off my penis after it good enough before round 2, or should I go wash with soap and water?

What does "round 2" include?
NEVER EVER insert a finger or other object into the vagina that has just come from the anus.

The answer is to end a session with anal stimulation or use a different and clean finger to then go into the vagina. Do not ever cross contaminate.

Wash with soap and water, is a good thing to do.

4) Any other "surprises" or concerns I should be aware of, given that this will be my first time? Just stuff like "oh yeah, you gotta watch out for..." or "hehe, he's never gonna be prepared for..."

Please read the information in this Sticky:
"Playing Ball" and How To Tips for Prostate Massage

Pay particular attention to the Going Inside section.

One last thing: Keep anal stimulation to just a finger or a dildo for the time being. A lot of intense stimulation can result from a well placed finger with dexterity. Many people draw the line with having a penis go inside. I suggest waiting on this for the time being and get used to fingering first. Having a penis go inside is more a guy thing that many gals and guys do not want to have happen.

Like Sera said...almost all the semen leaks back out. The first time my b/f and I did it.. he was shocked at what spurted out when he pulled out lol.

Also, Brandye always suggests that if you are going to do anal.. to wear a condom b/c there is a high risk of the male getting bacteria and such.