Depends what you've got to lose
[QUOTE=PaiMei;4970500]I've found myself in a quandary. Maybe someone can offer advise / a Hail Mary but really I'm just stuck I think. I've never had time for the sugarbaby game but recently was enticed to do so on Tinder. Absolutely gorgeous girl who flat out and unexpectedly asked me to make an offer. I said $$ and to my surprise she agreed. As we continued to chat I started noticing many similarities in our lifestyle / social scene. I dug around on FB and boom there she is and we have a million friends in common and she hangs out in similar circles -but like a decade younger than me. And that's it really. She's bangin hot, digs me, is ready to meet face to face tomorrow (no fee to meet), and $$ is a great price for a girl of this caliber (based on what I've seen on the sugarbaby thread). But I can't risk it. If she shows 1 pic of me (she still hasnt seen a clear pic of my face) or describes 1 of my distinguishing features to a friend or something that could be the end of it all. How would she get a face pic you might ask. Well who knows but if she does and shares it there's a good chance I'm outed. Woe is me. The temptation is unbearable. Just needed to get that off my chest.[/QUOTE]Like others have said, it depends what you have to lose.
I had a UTR a few years ago that I took on a few dates initially, and then the relationship morphed to where I would just go straight to her place for some action and leave. On our first date we went back to her apartment and got to talking over another drink and some music. Came to find out that she occasionally frequented a bar that I was a regular customer. I had never seen her in there before, but she knew one or two of the bartenders in there and even dropped the names of some other regulars. This made me a little nervous, but I was already there and about to seal the deal, so I went through with it. For about a week I worried about seeing her in public or her telling someone at the bar she went out with me. This was before I was using a burner phone or a fake name in the hobby. After a week or two I realized I was probably safe. I hadn't seen her at the bar, the mutual aquaintences who we both knew didn't say anything to me or act differently, and most importantly. My SO almost never went to the bar and didn't know anyone there.
So, I called her again and set up another date. I'm glad I did because it turned into like 10 months of the best sex I've ever had in my life. She probably isn't as hot as the one you are debating but man, the sex was crazy and she would do anything for $ per hour.
So, don't be afraid to take a shot if the risk / reward checks out for you. If you have an SO, I say don't do it. If there's no SO in your life, fire away.
Like another monger said, if she's respected by all of these mutual friends I can't imagine she's going to tell any of them that she's climbing on your rod for cash. You may be worried to have friends know you are in the hobby, but I would imagine she is too. This could blossom into a wonderful partnership between you two.