Bonus points for shemale
he's having the right attitude. For that orgasm he would pay money to that grill, but hey. He has been a smart ass - no money loss, the cum have been shot, time for some progressive job for a difference..!
She is a prostitue. The exact same guy has another video where he does the same thing. The woman comes up and says she'll help him with that for money. He cums and hands her $10 for watching and tells her to be safe out there.
Protip: Most prostitutes don't dress like fucking strippers on the street.