It took me a LONG time to get comfortable with barebacking. The first time I tried it, the top had to pretty much beg me (still remember what he said: "I want to help you experience something new," as if he cared, ha!). Eventually I let him go in bare, and it felt AWESOME, but he had agreed to pull out to cum (and he did, although he was obviously hoping I would change my mind, and I almost did). Pretty much from that point I bb'd regularly, although I would freak out most of the time afterwards and then not fuck for a couple of months. And I almost always asked the top to pull out and nutt in my mouth (big-time ATM fetish here, so that wasn't all bad). Every once in a while a top would refuse, or I wouldn't say anything, hoping but not hoping that he wouldn't pull out. But from the first time I tried it I pretty much stopped fucking safe. I'd either fuck raw, or not at all. It took me until my next boyfriend to start taking loads regularly. He and I split up, but by that point I was addicted to taking loads. So for me, it's less about wishing I had started barebacking earlier, and more about wishing I had started taking loads earlier. Much earlier. Now I understand that my place is to serve the top, which includes providing a warm place for him to unload.