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Pooping in my work boots 

Someone is pooping in your work boots when he is impeding you from doing your job.

In other words, he's bothering you while you're working or preventing you from doing your job.
FBI Guy: Don't touch anything, no trespassing..until we say so..

Forensics Guy: Man, You're pooping in my work boots!!

asian work boots 

Take off your Asian work boots and put on some socks. Your feet stink.

Chicago Workboot

While she's asleep, shit in her shoes. Hide in the closet in the morning, and masturbate almost to the point of ejactulating. When she puts on her shoes, she'll slip and fall and when she is on the ground, spooge on her face.
I totally gave that skank a Chicago Workboot this morning