Yes, you should wear a non-Latex condom and *lots* of lubrication.
Male or female, unprotected anal sex increases the risk of exchange of fluids (semen and sometimes blood) transmitting blood-born diseases.
As for rimming, a dental dam can serve the same purpose as a condom for purposes oral sex. Have fun.
you cant get pregnany , your a boy.... yes if your going to have anal sex then use a latex condom and use lube..... be prepared for some pain
Well, anal sex in itself cannot get you pregnant, but the fluids dripping down produces a possibility. I'd have him wear the condom just in case, especially if STD tests have not been ran.
Rimming is safe as long as you wash your mouth and anus throughly.
Hope this helps!