My girlfriend has asked me to have anal with her which I don't mind doing if that's what she wants. It would be my first time so I'm a little bit worried. Is it easy to. My one girlfriend let me do it once and never again. Other one not at all. Current one saids she likes it and lets me do it like once a month but I. In my case, we'd been half-joking about anal for about a month. One night, we were having sex (doggystyle) and she reached back, grabbed my arm to get me to.