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I'm a super realistic painter, so our styles may differ, but I usually paint with tiny dots/dabs to achieve this sort of effect. I would paint the skin tone down, and then take the black overtop of it. At the top, the dabs are going to be heavy and closer together, then working your way down, they get lighter and smaller and further apart, to the point where they're pretty much dots.
To clarify (since I tend to make words up sometimes), by dabbing I mean taking the brush and pretty much stabbing the canvas with it. You don't want a lot of paint on it for this.

Another technique I could recommend is a lot less detailed, but depending on your style, may work better... Painting side-to-side (kind of doing like a watercolor wash, or if you've ever had to paint a sunset) you blend the (wet) paint on the picture. I could go into more detail if you wish but I don't want to seem like I'm rambling. :)
 
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