Make sure to wrap it up before putting it in the hole. With so many different sexually transmitted diseases out there today it does not make sense to have sex with someone unless one of you are wearing protection and more than likely that is going to be the guy wearing it. If i can offer you one bit of advice it is this make sure to wear a condom while having sex.
Otherwise you could end up like the millions of people that every year contract a STD. And the last thing in this world you want messed up is your private parts, trust me!