Well if he is a good friend, then I wouldn't drill his girl (Unless she is just utterly fuckable).
Here is what I'd do. Tell her you are going to get another guy and a camera, and she has to screw the guy while you shoot pics and vids, every position, sign a model release, and the debt will be paid.
Then license the content to other webmasters
I'd never screw my friends girl, well, almost never.
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