No, this was my girlfriend's first cup experience, which I was rather intimately involved in. I know this community tends to be pretty matter-of-fact about all things anatomical and menstrual, and this story was just too... strange? Interesting? Not to share.
So... new girlfriend. We had just spent most of a week together, and despite the fact that neither of us was due for our period (we were, in fact, both mid-cycle) we both showed signs. It was very strange; I've had my cycle triggered by a woman I was sleeping with before, but in this case neither of us should have been able to trigger the other really. Best guess is that she'd been celibate for quite a while and having sex again woke something up in there. :) By the second to last day, she had started, and of course had no supplies with her. I suggested that she try my (sterilized) cup.
This is the part you might want to skip if you're at all worried about TMI. :)
She's not someone who's ever been overly comfortable with anything inserted in her vagina, and has rarely even used tampons. I tried to explain how the cup worked, show her the punch-down fold, that sort of thing. She hesitated and I told her that since I happened to know quite a bit about the shape of her vagina and where her cervix was, I could insert it for her the first time and see what she thought. Using my own cup has made me far more comfortable with menstrual flow in general, and we had been taking advantage of my lack of squeamishness already. There was a bit of giggling, but eventually I managed to insert the cup and make sure it was open, and told her to kegel a few times. She has some awesomely strong pelvic floor muscles and could actually pull the cup in or push it out with them at will. Pretty cool really, cue more giggling. This is not an experience I ever expected to have, and if I'd thought about it much in advance I might have assumed it would be uncomfortable, but it was fine. Fun even.
Okay, TMI pretty much over.
She wore it all day, but said she could always feel it. It was too large for her - I wear a large Diva, and she's under 30, no kids, and a bit shorter than I am inside. She said it wasn't particularly uncomfortable, just there. The best part, though, was when she went to the bathroom and came out practically jumping for joy because it didn't leak. I told her that I sleep naked in mine and that it has never leaked and she was SO excited. I realize this isn't true for everyone, but for me it's one of the most amazing things. :)
She handled removal herself with all the usual first-time learning-curve stuff: too much suction, spillage, etc. No pain though, and I had warned her about possibly spilling so no mess. She had the usual reactions - wow, is that the color and consistency really? - but no particular trauma.
Next morning, our visit was over and she had to give me my cup back and make do with a scrounged tampon until she could get to a drugstore. She texted me about ten times on the way home complaining about the tampon... which really made me chuckle.
So now - I'm going to get her a cup as a gift. I really do love my Diva and it worked for her, so I'm considering just getting her the smaller Diva. Barring that, one of the other silicone ones, I think? We're fans of silicone in general anyway. She's smaller than I am but not that small - the Diva's length didn't seem to be a problem for her. Her cervix is just reachable normally and drops a bit during her period but not that far - it's still pretty deep. (Mine is way the hell back there, personally.) Girth is more of a problem for her, but a too-narrow cup is more likely to shift and leak. Likewise a softer cup, I think? I'm tempted to get her both a small Diva and another cup - any suggestions?
I'll also get her some cloth pads... I don't use them because I prefer my cup even on very light days and it's never leaked. I can't tell I'm wearing it at all, so wearing it a bit extra is no problem. But she might prefer to have them as backup or for light days.
I'm excited... and amused. I wonder if anyone else has had this experience? I realize you kind of have to be lesbians, which cuts down on the possibilities. But I think it was a good introduction. And we're still giggling about it.