Stephee, I think I was about in your position. I assume you still have a beard? Do you think it shows in the pictures? I don't know if it is the lighting or five o'clock shadow. I think you'll have a very pretty face. How much do you currently weigh? The last shot is my favorite.
Here's my advice and it's free so it's worth every penney.
You have a nice smile. Use it.
Your eye makeup works but I'd go lighter on your cheeks. Perhaps it's because you are using a lot of foundation? It's hard for me to tell.
Here's a trick I used to use to make my face look more slender. Lightly apply a light color on your upper cheek, a darker color towards the center, the third and just a tad a bit to the rear and below the middle color. Then I'd find a brown powder and ever so lightly go from the bottom of my ear forward about an inch and a half. Experiment how far to go down. Brown will sort of provide a slimming effect so you can use it anywhere you want. But here's the thing. Use it sparingly!
Finally, when you do decide to go out, make sure to go to your favorite wig place and have them cut and style the wig for you. This took me two stupid years to figure out. I went through hell with the cheap wig look and people making fun of me. Make sure you ask them how to take care of it and keep it styled correctly. I bought a fairly expensive wig and got sort of a punk/Joan Jet cut that I really liked. It did NOT look punk on me. It looked great. Once I had that piece, I started passing easily in public. I had dark hair back then now it's blond. Go figure.
Another point about wigs. Try to get one to match your real hair color. Or dye your hair to match your wig. Brush some of your natural hair in front up into the front of the wig's hair. If you can do that right in front, no one will ever know you are wearing a piece.
Chin up.
Cindi