It is entirely possible to make up a darker skinned person to appear lighter, but not with 'street' make-up. This task requires theatrical make up and a good deal of practice. Frequently make up students are tasked with exactly this proposal (either light to dark or vice versa) with natural looking finish. Actually, one contestant on Face Off
last season opted to do this with her model for a specific challenge, even though it had nothing to do with the challenge itself (she did it because she'd used the same model a couple times in a row- wanted to show her own diversity).
So, my advice is:
- take a theatrical make up class
- find a theater/ make up student and let them practice on you
Here is a fun quiz, two of these awesome make up jobs are race switches