I indeed did when I lived in Wisconsin. The two clubs were located in a couple of small towns and were only about 20 miles apart, but still they each list a different city on their address, so IMO that does count as clubbing in two cities on the same night ;-)
I just pulled this off last month. Hammond, Indiana and Harvey, Illinois same day. Two clubs, two blow jobs. 10 miles apart, less than $200 spent total.
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