My female friend and I once took a trip down to Jamaica to hang out and see the sights. We’d get really drunk each night and we’d fool around but she’d black out and never remember a thing in the morning. One night while I was going down on her, I stuck my pinkey finger in her ass. She clearly didn’t like that very much as she winced when I stick it in.
The next day we were talking about sex and I asked if she had ever had anything in her ass. She told me “no” and I just sat back and smirked.