Ok - if you're married, trust your partner to not have an STD, etc - then consider using butter as a lubricant. Just get quite a bit, rub it on that little hole slowly, then get in a little bit more and rub around the ENTIRE inner part to help loosen it up. Then, just keep that up - applying more and more butter as needed. Pretty soon - they'll be all buttered up and ready to POP. Anal sex feels great . . . some of you guys should try fingering your own asses too while jacking off. As mentioned, use butter. Good god - you will fucking love it! It will probably feel somewhat "weird", especially at first, but just keep jacking off, rubbing that hole and fingering it, and you'll feel an experience like never before - especially when you're ready to cum.