Help! I can't make a move, I'm a teenager again!

Alright, I'm a 32yo 6'4" attractive funny male, well hung, no big deal. Had a bad 4 year relationship end 6 years ago. Since then I've stayed purposely single. I date, flirt, I don't play around but I get laid enough to keep me satisfied but not enough to hurt anyone.

I met a slightly older woman who seemed out of reach, became friends for months. Well look at this, feelings started to percolate. This whole time I havent kissed her, and the last 2 times (the only 2 times) I got her back to my place I failed to make a move. Its not a physical problem, and I'm not scared of rejection (she's made it obvious I missed both opportunities), so set aside the normal teenage insecurities. So why do i feel like a teenager again? Why am I scared? I'm not afraid of commitment either, having her mine would be great! Its the initial physical contact. I can't make a move on this girl! Its baffling and very embarrassing. I'm at a loss. It'll happen eventually, but I'm afraid this is tainting my image. Girls want men, and I'm sure as hell not acting like one. My fear now is another guy will swoop her up. I don't make a lot of money and she has 3 kids. I'm one successful joe away from the boot now that this fear has got me stuck. Who knows, this might end well anyway, but i gotta know, has anyone had this same problem that normally isnt a problem?