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A couple's night takes an unexpected turn when a game of spin the bottle is suggested. It's Jim's turn to spin, and the bottle stops with its point to Adam. They kiss, much to the excitement of their girlfriends. Each step further brings them a little further down a path of humiliation and pleasure, and that night is only the beginning.
Did the women plan the whole thing? Angelica, Jim's girlfriend, takes him through a whirlwind of shopping, shaving, and embarrassing acts, even going as far as putting his manhood in a cage, for a full week. That next weekend is the climax. The night when Jim is to become Jenna and please his girlfriend by showing his female side. They arrive at an upscale hotel, and Jenna can feel everyone staring, but can they tell she's a man under the wig and all that make-up? Even with the heels? At that point the line is blurry, even to herself.
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