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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.
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 both those items off her wedgie to-do list.
Featuring: Star Nine
Tags: Bullied OrgasmClassic BullyingCum in PantsPantsingPantyboySissificationSmall Penis HumiliationStoryline Wedgie BossWedgies
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