OK, sorry I didn't see your pictures last night, but I saw them just now, so my advise to you is, and please dont take it the wrong way, but only as advise to achieve what your asking for..
1st, you need to drop your wieght down, I see a beer belly, & looks like your retaining lots of fluid, like in the neck, so stop the Salt & Sugar intake, fast food & fries, eat more Green veggies, & a well balanced meal with reduced portions, dont eat at night, limit your drinking except for water..
I say this only because I see the huge potential you do have, so as your dropping the pounds, it will give you time to learn how to apply makeup better in the mean time, but it does take lots & lots of experimenting & practice, & more practice till you find the right products to use & get the look you want..
Personally, I wouldn't bother with cosmetics from Suddenly Fem, it cost more & not as good as you can get from any Wal-Mart or a drug store, but even better, I would suggest on going to Macy's or a Mac store..
So you do that, & you'll be be amazed in what you will achieve in looking more fem..& feel better too..!!
Just so you know,
I started out as obese, & said enough is enough, and decided to start to eating better since Feb 09, and because of it, have lost over 9 inches, closer to 10" on my waistline & still losing more..
You can do it too, so Good Luck!!!