Bree my heart goes out to you, I remember feeling exactly that way.

RD's comments were spot on. If you really want to blend, then you have a lot of work to do. I like what you're going for with light and natural looking makeup, but you don't have the face for it. You are very good looking, no doubt, but your face is way too handsome to be feminine enough to try and be too discreet with the makeup. The best thing I ever did was seek out advice from pros, and not just one, but several. I eventually met Avital who has her own little makeup salon and she and I quickly became great friends. she taught me so much about makeup last year that my head is still spinning. Before my FFS, I had some of the same issues as you and there's two things you need to learn; color and contour. If you're serious then I would recommend hair removal as well. Talk to some laser places and get some ideas. Laser is much faster and you will be surprised at how much losing the beard shadow will feminize your face. In the meantime, don't pack on the foundation for beard cover. I used to have a two step process with a yellow stick and a reddish orange cream that I would put on before the concealer and then foundation that worked pretty well. The key with makeup is color. You must get the colors right for your skin tone. Your makeup looks good, technique wise, but you need more of it in the right places. Minimize your jaw, nose, and forehead to soften your face and good Lord do something with those brows. ;-)

You should meet somebody like MelissaRose, because she's a part timer who does a fantastic job with her makeup.