Who says Kelly wasn't a hooker? And why wouldn't Skeeter date a hooker? He married Bridgette after all.

And why would Skeeter be mad at Belladonna? Maybe he just looks at that incident as "training".

Finally, consider that maybe it wasn't so much that Skeeter found the ultimate girl for him, but perhaps that Kelly found the ultimate pimp for her...
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"If they can't picture me with a knife, forcing them to strip in an alley, I don't want any part of it. It's humiliating." - windsock