Wedgie Boss Trilogy SD
Star is having the best week at the office now that her old wedgie victim is her new temp worker. She makes him wear tighty-whities to work and start off each day by begging for a wedgie. Star is a very experienced bully so she knows to keep pushing the limits to make sure her office boy stays squirming with humiliation.
Star decides to add some embarrassing labels to his undies since he already has his name written on the waistband. Once she is done marking him with a sharpie then Star yanks his undies up nice and high so his undies, and the embarrassing words written on them, are clearly visible all day long. Even after all that, Star still does not let her humiliated wedgie worker off the clock until he completes a little light ass worship.
It is Sam's last day as her wedgie worker and she plans to send him off with a bang... right into his wedgied panties. In her old bullying days she got to see him dressed up as a girl but never got a chance to wedgie him in panties. Star also made him wet himself once but never made him cum with undies up his ass. Today Sammy is going to play the dutiful sissy secretary and help the boss cross two items off her wedgie to-do list.
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