My 4 year old was our cervical cap baby. ;-)
I was in a different stage of life though. I has been a virgin up until using it, started using it on my honeymoon and went through three cycles before I got pregnant. I'm not sure why it took us so long... Lol. Our first time we used it, it ripped the condom off my DH and popped off sideways. It sat in there like that overnight until the next morning when it slid out with a VERY unsexy *plop* in the toilet. You should have seen us looking for that condom though. Bahahhaa. "what do you mean you can't find it, it was on your penis!?!?"
Yay for virgin weddings.
Seriously though, you could go get fitted for one and see how you like it. If you struggle with the fitting, then those first few uses will be awkward. But a combination of charting and the cap could help you get comfortable enough to use it during fertile windows? You can put it on earlier in the day and leave it in overnight.