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.