Mary Ann forces Gilligan to be the new sissy maid in this caption. All she has to do is keep the giant amused by continually humiliating and degrading Gilligan in front of everyone so the all keep laughing at him prancing around in the sissy maid dress and high heels.
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Sissy maid in chastity. She always get her boyfriend to invite one total loser to poker night. This way the ladies have some extra entertainment in the other room and she doesn't have to clean up the house. The maids outfit comes complete with a locking metal chastity device. Guess who has the only key!
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Any submissive girl or sissy will gladly serve as entertainment for the guests.
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A good sissy maid takes the time to clean all the shoes.