First time:
O_o awful experience. I found them extremely invasive and I could FEEL it inside me. It hurt like hell to get out. I plan to be a virgin until marriage so I felt awful about learning stuff about my body and putting things in "there". I swore never to try that again.
This time:
After a month a calmed down and I tried it again. This time I did some research and I became more comfortable with the idea after being reassured that using a cup doesn't make you any less of a virgin. I actually had no idea how the your period "worked" (I had previously tried to keep myself as ignorant as possible to this kind of stuff because I was convinced that not knowing somehow made you more innocent). I had only been using pads previously, I originally thought the the entire walls of your vagina bleed. I had no idea what or where the cervix was. After I figured that out, I found it and tried again. I actually got up the courage to learn more about my body through reading a lot on this site, I've been stalking this community quite a bit actually. Before I knew how to do it right (or what works for me) I was putting the cup in there and pushing it up as far as it could possibly go and I think the cup was running into and irritating my cervix. >_< (if that's possible, I don't know, I just know I needed to wear it lower for it to work)
This time, I tried and wore it how I think you're suppose to and I love it! I can NOT even feel it anymore. Before, I would always have to use the heavy duty night time pads just for going about my day and often wreck really cute clothes just because of my heavy flow. Sleeping and sleepovers were a nightmare, I'd hardly sleep because I was so worried about leakage. I really don't think I ever have to worry about that anymore. The cup works, it doesn't leak, heck, with pain pills it doesn't even really feel like I'm on my period. So far, I'm really happy I discovered it and gave it a second chance.
I just thought I'd drop by and share a success story and possibly help out anyone who may have had my problem. I think more than anything, I just needed to become comfortable with the idea of it and needed to realize that there's nothing obscene about wearing a cup just because it deals with that part of your body.
One more thing, I would definitely like to thank this community. It helped me out a lot. I'm extremely pleased with my cup. :)
Oh and for reference, I'm using the model one Diva cup! (with the stem trimmed off) ^_^