As a male, I've sometimes done a shortish set of songs from a woman's perspective. Rosemary's Sister or He Fades Away, as examples (they were both written by men, I should note). I think it's harder for me to put those across (for example, I did not introduce He Fades Away properly in one setting and got a lot of women laughing in all the wrong places). But also check out good songs written by woman writers like the above mentioned Judy Small (Mothers, Daughters, Wives and many others) could be sung by anyone.