Im fairly new to this, and recently I came across a situation that left me baffled and confused and I wanted some expert opinions on this.
My first time (non-escort) was 8 years ago with a classmate when I was in school. After I graduated, I kept moving for a few years because of different jobs. About 3 years ago, I got a stable job in Vegas and been here since then.  
So the story goes like this. A very old friend was visiting Vegas and decided to stay with me for a week and introduced me to the whole escort scene. Since it was my first time after almost 5 years of no action, I was curious, nervous and scared. We went over some of my friend's recommended profiles and I picked one. Just for reference, she was $600/h.  
I read a little about etiquette regarding meeting an escort and bought some chocolates for her and put the donations in a envelope. Met her and had a very good time. I tried being a total gentleman and she even mentioned it when I left.
I saw her again two weeks later. Took more chocolates and champagne this time. Had much better experience this time, with something extra. We were making out in the Rocking Horse position but I wasnt in her. We got so heated that she climbed closer and took just the head in, without rubber. She whispered that she wants it fully inside, and I was worried a bit but I was so turned on that I let it slip in. I reasoned that since she's charging $600/h, she must be safe (not sure how accurate that logic is). Had an amazing time and came outside.  
Fast forward one month. Saw her again. Did the same chocolates and champagne routine. Same thing happened. She whispers that she wants me inside her, and I did bareback in missionary. I was having a  awesome time and after few minutes she whispered again that she wants me to come inside her. That was so surprising to me that I stopped suddenly and went soft. She mustve seen the look on my face and told me that if Im uncomfortable with it, I dont have to do it, so I finished outside. As I was leaving, she told me that coming inside offer is still on the table, when I see her again.  
A month later, she left for Europe (I think). That was almost 2 years ago. About 2 weeks back, I saw that she's back in Vegas. I called her and we had a good talk and I asked her discreetly that if I can have the same offers I had last time, and she laughed and said yes, she would prefer it. I setup an appointment for this Saturday.  
So my question, after such a long story, is that is she asks me to come inside her bareback, should I? I know about the drawbacks of doing this, but I read some stories where people did that, and I was wondering if someone here has experienced similar situation in the past. What would you do in such a situation?
Thanks for all the help!
So my questio