How should I prepare for anal sex?
When foraying into the world of butt love, there are three important factors to consider: hygiene, safety, and comfort. Hygiene is often a major source of anxiety for those trying any kind of anal play for the first time. Rest assured, M4M: it's not going to be all honey and roses, but performed correctly, it will be fine.
Clear your bowels (the natural way, please—home enemas can be dangerous, especially for frequent use), take a shower, and if you're really nervous, wrap a bit of paper towel around your finger and gently insert it into your anus to clear any stubborn debris. If you and your honey are planning a dinner date, it might be prudent to bang first and eat later—you're less likely to have an anal sex oopsie on an empty stomach.
Many people choose to use condoms on their partner's penis or toys during anal sex for both hygiene and safety reasons. Just remember, if you also have a vagina, it is absolutely, 100% not safe to use the same condom in both the vagina and anus. Going from the vagina to the anus is certainly less dangerous, but to be safe, keep a small pile of condoms on hand if you're planning to switch things up.
Another note on safety for those with vaginas: If you're experimenting with anal sex as a "safe" alternative to vaginal sex, remember that anal sex is still definitely sex. It comes with all the physical and emotional risks and rewards associated with vaginal sex, including pregnancy and STIs. In fact, anal sex presents a higher risk for the transmission of STIs due to the delicate and easily-torn tissue of the anus and rectum, so it's especially important that you communicate with your partner about your health needs. (Don't be afraid to ask your partner to get tested, and remember to get tested regularly yourself!)
As far as comfort goes, y'all know the golden rule of sexy times: lube, lube, and more lube! It never makes sex worse, and it's an absolute necessity for anal sex. M4M, since you're a first timer, pick up a bottle of Astroglide (or any other water-based lubricant—the thicker and more gel-like, the better) and spend some time getting to know your butt, either alone or with your partner. Start with a finger or two and work your way up to mid-sized objects like butt plugs and other small toys.
Just like the vagina, the anus is an incredibly elastic orifice, so working your way up to bigger objects is a good way to ensure that you're as comfortable as possible. (And don't worry—it'll tighten back up! The vagina tends to snap back a little faster, but your anus won't octuple in size from a little anal play.)
Is better sex one of your New Year's Resolutions? Submit a question or topic suggestion to the Girl in 04C for a bangin' 2015.