Not very likely. Some people's asses just weren't built for recreational activities and mine is one of those. Between doing a sitdown job and passing eggplant-like turds, I need all the recovery time I can get.
A finger isn't smooth enough for me anyway. It might be OK for tickling and massaging the outside ring, but for penetration I could only tolerate slim and very smooth toys or objects (preferrably soaped up ). About 6 years ago I experimented with it, and even that way I endedup regretting it the next day half of the time.
Not a big loss anyway since I'd only be in the mood for it very ocassionally.
Besides, the idea of a woman getting that close to a man's ass turns me off. I simply can't get past my perception of most men's asscracks being much nastier than women's, so if a woman goes there (especially mine...) it would be really hard for me to feel attracted to her, having fouled herself that way.