[Samantha Rogers]

Andrea, it just takes a little work and practice, sweetheart. Don't beat yourself up. Remember GGs start learning from their Mom when they are little and have lifetime to get good. And some GGs never really get good. Besides, they start with an advantage most of us do not have...a feminine face to start with. Plus they don't (usually) have to worry about beard cover...lol

So here is what you do...start by watching any of the many online makeup videos. There are many, including some on youtube in addition to the ones on manufacturer websites. In addition there are many on youtube specifically aimed at CD and TG.
Read (or look at the pictures) in women's magazines.
Study paintings of female faces and look to see how artists have applied light and dark colors to shape and accentuate features.
Pay attention to women and look to see what they have done. In short, begin to educate yourself.
Once you are ready, go to Target or Walmart and begin to purchase some inexpensive items to start with...some kind of foundation, translucent powder to set that, blush, an eyeliner of some kind, eyeshadow and highlight combos, an eyebrow pencil or shaper, lipstick and various brushes, sponges, cotton balls and some baby oil to remove it all when you are done.
(Target and some other stores sell a very inexpensive line called Elf, and much of it is very usable and decent...things don't need to be expensive to work, especially in the beginning)
And then start to practice.
Foundation
Powder
A bronzer to sculpt the face, if desired.
Blush
Eyebrows
Eyeliner
Eye shadow and highlight
False eyelashes and/or mascara
Lips (use a lip liner pencil first to outline the shape.
At least thats the order I use.
Karren is pretty much our makeup wizard and resident expert so maybe she will chime in with some tips. I am sure I could sit at her knee for hours learning, myself.
As you try things be prepared to make mistakes and have to take it all off and start again. Practice. Try different things. Go big, go small, see what works and what doesn't. Learn to blend and do things subtly.
And when you finally do get to where you are somewhat pleased, add the wig. It will change everything for the better, especially if your wig is good and suits the shape of your face.
And then expect to keep practicing. Presenting a feminine illusion or expression is an art. Learning how is a little like learning to play Bridge. I can teach you the simple mechanics in an afternoon...and then it takes a lifetime to get really good.
It isn't rocket science but it does take time and effort.
It is worth it! It really is!
Lol
Hugs
Sammie