I have never had anal, except if you count fleshlight experiences. When we were younger (and very inexperienced), my wife and I gave it a try. But I wasn't successful at getting my dick in. (I am not sure even if we used lube.) It hurt too much for her. So we never tried again, although one day she indicated that she was open to it. I said no because I didn't have a condom on me. Later on, I wondered if a condom would be necessary. We have never had sex with anyone else. Do you guys who do anal with your wives or girlfriends, who are you only partners, always use condoms?