My boyfriend keeps asking me to have anal sex. If only one of you wants to try anal sex, this is not a behavior that you do as a favor for your. For the next five months, anal was the only kind of sex they had. . "You're thinking, 'I don't want to hurt her, and I don't want shit to squirt out at. Don't get me wrong — there is no issue when it comes to sex otherwise, but I still feel unsatisfied sometimes. I just want him to try it once for me.