Vintage Cross Dressing Videos

Roleplay is often the beginning of entering the world of BDSM and Fetish.
Although most do not come to realise it until later on, your Fetish desires could quite simply stem from infancy. As a small boy, you remember seeing a beautiful young sophisticated woman, dressed in a tailored suit, cream satin blouse, quality leather gloves, and the most stunningly slender toned legs, laced with sheer nylon seamed stockings.

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Mistress Amanda Wildefire – No Escape

This vintage video is great for those who are into serious inescapable bondage. Shot years ago in Maxcita’s playroom, Mistress Amanda Wildefire secures her subject Hudson in a small padded cell complete with E-stim attached to his cock. Hudson is laced into Maxcita’s canvas ‘Exosuit’ which includes a pair of unique lockable helpless mitts and bizarre-looking zipper mouth hood. Hudson is secured in a standing position in the center of the cell, attached overhead and to all four walls (including the door) with chains and carabiners.

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Mistress Misty – Upside Down Under

Mistress Misty enjoys her subjects strictly restrained so we hung her subject upside down using some vintage inversion boots. This piece was homemade decades ago. The design and quality gave me peace of mind as the rigger but I did like tweaking him a bit. Mistress Misty is a ball slapper but her subject didn’t seem to complain.

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Bondage Liberation – Public Bondage Shopping

All the dominant women and submissive men are going to like this video. Our friend Elise Graves takes her submissive friend out on the town in handcuffs attached to a waist belt and hidden inside the pockets of a hoodie. Their first stop was a vintage clothing store where Elise try’s on a leather skirt, and then forces her handcuffed friend to buy it for her. The next stop was a local cafe where she locks his handcuffs under the table and then proceeds to spoon-feed him oatmeal. Poor guy!

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Troy Orleans – Inflatable Leather

This is a cool video featuring NYC’s popular mistress Troy Orleans. Troy specializes in bondage and always surprises us with unique equipment. In this video she pulls out her vintage Fetters leather sleepsack. This is not a standard sleepsack, but a unique inflatable leather sleepsack.

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Madame Catarina – Safari Caning Scene 1

Madame Catarina looking stunning in vintage jodhpurs, pith helmet and riding boots returns to her Italian villa after a riding expedition with her stable boy. The Berlin Mistress has a slave prepared for a heavy caning session but decides she will amuse herself first with her stable boy slave.

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Dominatrix Annabelle – Pony Play

Dressed to kill in My superbly figure hugging jodphurs, 6 inch leather stiletto boots with Vintage Spurs, and a cream leather jacket! It was time for My two ponies to get some fresh air into their lungs, and enjoy a fun day out overlooking the valley in one of My paddocks.

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