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Sissy - Free Videos & Galleries
Be My Sissy SlaveFeaturing Mistress Georgia. Mistress Georgia has decided she wants to transform her slave into an obedient sissy slut, but teaching 'him' to be a 'her' proves anything but straightforward! His clumsy ways lead to sharp punishment, over his Mistress's knee. He will become a sissy slut for her and he will behave like good slut should!Bobby Turned BobetteFeaturing Miss Severity Myers. Bobby has simply gone too far this time. After being allowed a boozy night in with his work colleagues, he left the remnants of his party strewn all over the living room. Miss Myers is not impressed and decides to make a few changes to their relationship. He most definitely will not be wearing the trousers from now on.Mouth And Ass DestroyedThe masked slave got a nice red lace bodysuit, what leaves his ass exposed for Mistress Tatjana and Mistress Nomi. The girls want to destroy both his ass and mouth with the help of their brutal strapons. They move the slave into different positions, so they can fuck his ass and deepthroat his mouth too.Victoria's New TV SlaveFeaturing Lady Victoria Valente. Lady Victoria Valente has her new sissy slave dressed for the first time. Her first training lesson is how to pleasure the Mistress's strap-on cock.Panty SnifferFeaturing Miss Zoe. When the man servant is caught sniffing Miss Zoe's worn panties she takes decisive action. With genuinely worn panties for this scene, she covers his head in worn and fragrant pantyhose, making sure the sweaty gusset is firmly over his nose and stuffs the worn panties in his mouth. She then decides to put him in one of her dresses and gives him a good hard over the knee spanking. She wants him to remember the humiliation of this day and it's unlikely he'll ever forget!The Loose HemZoe's favorite skirt needs some attention - the hem needs shortening. She asks her husband Vincent to drop it off at her sister Molly's. Vincent has always had a thing about her; Molly is such a flirt and a tease. On arrival Vincent is invited in. 'Oh Vincent, could you remove your shoes - the carpets have just been cleaned you see.' After a hug and a peck on the cheek they both go in to the living room. 'Let me look at Zoe's skirt. The hem needs shortening you say?' Molly gives Vincent a saucy grin and a wink, holding the skirt up to the light. 'This is far too short already! That sister of mine needs a damn good spanking. If mum saw her out wearing this...' Molly giggles and remembers the time that she was spanked side by side with her sister many moons ago. Playfully she holds the skirt up. 'Here. Hold this a moment. Let me see the length?' Vincent starts to take the skirt from Molly but she says 'No no no, silly. Let me!' With firm fingers she holds the skirt and pins it up against Vincent's hips. 'There, see.. You'd look good in a skirt.' Vincent blushes. As Vincent gets redder in the face Molly leans forward and says, 'Don't be shy. I've known for years you like cross-dressing, and always wanted to be put in a skirt.' God, what a tease Molly is, he thinks - but how the hell did she know Looking down at his feet Molly says 'Those socks seem a bit thin for wool...' she leans forward and speaks quietly in Vincent's ear, 'Now tell me. Are those stocking or tights you're wearing under your trousers?' Vincent holds the hem of the skirt against him as Molly undoes his belted waist band and his trousers drop to his ankles. Molly gasps with delight as she sees that his legs are indeed clad in sheer black stockings... and his boyish buttocks are decorated with vivid red cane stripes.Belittled, Bullied & BustedFeaturing Divine Mistress Heather, Lady Mia Harrington. When Mistress Heather and Lady Mia Harrington get a worthless gimp to humiliate, they don't hold back. This slave got more than he bargained for when he turned up in a cheap dress and little pink panties. After a good hard over the knee spanking, whilst being instructed to worship their boots, he is then kicked, slapped, ball busted and spat on. Two stunningly beautiful Mistresses, head to toe in tight leather in a feast of a humiliation movie!