Miss Eva Ray has dressed her ex boyfriend as a sissy in a silky frilly dress, and is now going to punish it for being a pathetic excuse for a man, and a completely worthless boyfriend! Miss makes the sissy do twirls, and prance around like a princess, while she ridicules and belittles it. Miss lifts it’s dress up to show off the stockings and frilly knickers the sissy is wearing! Miss tells the sissy that it’s new clothes suit it far better than male clothes he used to wear! Then never looked right on it! Miss lifts the sissy’s dress, and taps her cane over the sissys satin knickers, with i...

Miss Eva Ray has dressed her ex boyfriend as a sissy in a silky frilly dress, and is now going to punish it for being a pathetic excuse for a man, and a completely worthless boyfriend! Miss makes the sissy do twirls, and prance around like a princess, while she ridicules and belittles it. Miss lifts it’s dress up to show off the stockings and frilly knickers the sissy is wearing! Miss tells the sissy that it’s new clothes suit it far better than male clothes he used to wear! Then never looked right on it! Miss lifts the sissy’s dress, and taps her cane over the sissys satin knickers, with it’s chastity belt underneath. Miss instructs sissy to hold his hands out, and she begins caning sissy’s palms, laughing at its discomfort! Over and over again, harder and harder Miss thrashes the palms of the frilly sissy, 50 times! Miss then leads her sissy ex to a rusty old boiler, and strips the sissy down to expose his back. She begins thrashing the sissy’s back harshly with a leather flogger, telling it how pretty it looks in a shiny, satin dress. Miss really tears into the sissy’s back, lashing away harder and harder, making its back bright red! She uses all of her might, to beat the pathetic sissy ex boyfriend as hard as she could, getting revenge for all the time she wasted with it! When Miss was finished, she pushed the whip handle into the sissy’s mouth and made it lick it like a cock whore!

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Keywords for this clip include:

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