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1.
When a man inserts the end of his penis into his own asshole.
That dude is so gay that he gave himself a Key West Boomerang just to get a piece of ass.
by Mr. Clit June 05, 2006
 
2.
When a man inserts his own penis into his own asshole.
Dave was amazed Troy's cock was long enough to give himself the Key West boomerang.
by JulioSilverwolf October 15, 2010