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1.
When a male masturbates (see jack off) while wearing only a tuxedo top and, optionally, other dinner party accessories (options include: handkerchief, top hat, cigar, etc.).

A play on words on the whiskey brand of the same name.
Roger felt fancy on Friday night, so he decided to give himself a Gentleman Jack.
by Andy Heen-Aerms January 16, 2011
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