As I mentioned before, if there is some green-ish personal hygiene habit to be experimented with, I'll try it. After reading Our Bodies, Our Selves in 1993, I pondered who might be doing menstrual extraction. (No one?)
Thankfully, before I ran into someone who was willing to do menstrual extraction, I ran into the Keeper menstrual cup written about in some riot grrrl zine. A cup that sits up there, no risk for TSS, creating a seal and it only needs tending to once a day? I was more than in. I had already tried out cloth pads (meh) and this was around the time Village Voice ran "Pulling the Plug on the Tampon Industry"in 1995 (via spotsite) so I was definitely ready to take the jump.
I was so excited to use it that I immediately tried it out without reading the instructions and when I managed to fold the pretty stiff gum-rubber cup in half twice to get it up there, I successfully created the vacuum seal. But then had no idea how to get it out. Let me repeat, in case you're not getting what a naive eager beaver I was: I stuck an object up my vaginal canal without reading all the instructions. I tugged a few times and to put it mildly, it was not a fun experience. I had visions of having to cut a hole in the bottom of the Keeper to release the seal before my roommate got home and wanted to know why the hell I was locked in the bathroom for so long. Finally I calmed down and read the instructions...to the end. Ah, all I needed was one solo finger to poke the side of the rim, breaking the seal and getting it back out. But that was a little painful too, dragging it back out only half-folded.
I found that I liked all the features of the Keeper. I liked all the things mentioned above - I put it in during the morning hours, took it out a night and it was no trouble. Nothing to change, forgot it was there (mostly). Wasn't wasting any cottony products. Could use it at any flow with no TSS risk. But the honeymoon was soon over. The gum-rubber was pretty stiff and it didn't mold to my body (and by body I mean vaginal canal). Instead it stayed pretty stiff and caused me more severe cramps if my cramps manifested as stomach-area issues (which they normally did). I never mastered keeping it folded into quarters on its way in (so sometimes it'd open before fully inserted, in a place it shouldn't have been full size and I've have to get it out while in pain). I finally decided I was done with it - more severe cramps and some painful entry and exit moments clinched that over the first 6 months of its use.
I'd pined for something that would work similarly but without the extra pains. I'd heard about the UK Mooncup but didn't know anyone who had one. I'd heard about the Diva and kept my eye out for it in stores (Bluestockings mostly, around the time it was still more of a feminist/lesbot bookstore vs a more-encompassing bookstore) or for people who mentioned using it online.
Finally, one day in the 4th Street Co-Op, I saw it mounted on a display. I went over and fiddled with it. I went and asked the guy at the register how I could get one out of stock. "Oh, the Divacups - getting one of those things is like Communist Russia. You have to put your name on a list for the next time they're ordered." "...I guess I'll order it online?" (After telling a 4th Street Co-Op member this story recently she surmised it was Jason Trachtenberg at the register - and in hindsight, I'm pretty sure she was right. Hello to Jason Trachtenberg, if you Google your own name.)
I like the Diva Cup experience better than my experiences with the Keeper. It's way more supple, it's easier to handle (both upon entry and exit), it's softer on your body (important for up there!). I'm 35 but use the smaller version of the Diva and it's fine. On the first two days of my period, I believe the shape of where the cup sits changes slightly so I have some minor leakage on the first two days, if any. After that it's a non-issue.
Also worth noting is that the Keeper.com website now also sells the Mooncup - which is the silicon version of the Keeper and I imagine it's just as good as the Diva Cup. I just happened to find the Diva Cup available first.
Some people say they have an incredibly heavy flow and have to empty the cups a few times a day but I've never found that to be the case. I usually put it in while I'm in the shower in the morning and empty it before I go to sleep at night. Sometimes I'll wear it at night, too, and sometimes I won't - depending on how I'm feeling. There's only a few times I had to deal with it while in a public restroom and even then, only a few times I've had to readjust it or take it out in a public restroom with a shared sink.
** There are some other experiences in the comments, too, so if you're considering getting a cup, please feel free to read those too! Thanks to those who commented with their experiences!