Thank you all sooo very much for your replies, it's helped me feel better about all of this. I just have to relax and have fun! And I'm going to try to cut back on the flogging, and maybe try to find some lube...
I guess I didn't want to use the condom because I couldn't feel anything as it was, so it made it feel a tiny bit better. But I guess the risks of her getting pregnant aren't worth it. And she's not on BC, we were talking about that a loooong time ago, and I can't remember exactly why she said she never wanted to be on it, but that's her stance...
And about the STD stuff... I'm pretty worried about that. There was a time where she her gyno thought she had herpes, and she told me about it the very same day she found out, so I know she's very honest and open about telling me that kind of stuff. Turned out it was just like, bumps from shaving, so she doesn't have it, but she has also let me know that although she has a lot of experience, she is clean. I don't want to say I don't believe her, because I do trust her, but I'm not sure if she says she's clean based on her using mostly condoms with the other guys, or if she's been checked out. And if I ask her if she's been checked out, she'd probably go nuts on me... Anytime I bring up her sexual past, she cries because she regrets having had sex with 10 guys... And I know her crying is legit, I can feel it and hear it in her voice that it hurts her. So, I guess I just gotta not ask, use a condom, and take the chance... But does that mean I can't go down on her anymore and stuff? Ugh...
