Last night, since we couldn't have sex due to period (my diva was in), we went for anal. No discomfort with the cup at all, despite my first time use making my vag a little sore (I tend to take it out and clean it a lot more often than I need to... way too used to tampons.) I was freaked out about trying, and he told me to just relax, and it didn't bother him... but he said it in that sex voice they have. I've never really messed around on my period much at all (not much on me anyway) and to be able to have a kind of sex so intimate while on my period was liberating. This cup deal just keeps rackin' up the kudos. I feel amazing.