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In the same vein as a handjob, bringing a man to orgasm by masturbating his penis with a pair of boots. Typically, these boots are being worn on the feet/legs of whoever is giving the bootjob and invovles rubbing the cock with the soles, feet, or shafts of the boots.

A quick look on Google for the term will turn up a few videos for reference, but these often seem to involve fat, ugly birds, presumably because they're fat & ugly, so frankly will do anything sexual for free/cheap as they can't afford to be too picky.
She put my cock between the shafts of her thigh high boots and gave me a bootjob by grinding her booted legs back and forth against my tool until I blew my load all over them.
by Just Another February 21, 2009
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The act in which a man is havng a foursome in which one women is giving head while the other two are simotaneously taking off his ski boots. The ecstasy is said to be too much for one man to handle...
Hey bra, after getting first tracks on the mountain i met three girls and got a bomb ass Boot Job.
by umichmatt January 07, 2010
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