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You are always asking the woman in your life for little favors, whether it is your ex-girlfriend, step-sis, or old college roommate. Lily Lane is on that list of people but this time when you show up asking her to co-sign a lease, Lily decides to make you beg in the most humiliating ways she can imagine.
You might have been shielded from the sting of your failures before but if you want Lily's signature today then you can ask nicely. While wearing nothing but her panties. And giving yourself a wedgie. Also sucking your thumb. She makes a little game out of coming up with fun ways to make you degrade yourself while she reads over the boring lease documents. Lily is pretty creative and pretty mean so jerking off while she makes jokes about your dick size ends up being the least embarrassing part of playing Lily Says.
Featuring: Lily Lane
Tags: AssBig TitsExtreme HumiliationJerk Off InstructionPantyboyPOVRegression HumiliationSmall Penis Humiliation
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