Length: 36:51 Maid Turned Slut 14 Pics
 
 

Featuring Mistress Eloise

Mistress Eloise is taking her sissy maid in hand, during this weeks appraisal. She wants to improve and teach her to be a better special girl, so after checking her uniform and punishment book, she is put over her knee and given a long correctional spanking. Her oral and anal training is then advanced by Mistress, using her realistic strapon dick to fuck her mouth and then her tight, virgin ass, making the maid moan in pleasure at the delightful experience. Maid is then placed in the bondage chair and Mistress Eloise uses a vibrator on her chastity covered cock until it empties a months worth of cum, her last reward for a long time.

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Length: 19:33 Encased In Pink Nylon 4 Pics
 
 

Featuring Miss Eve Harper

Mistress Sidonia is playing with her cute doll Alexia, she puts her in tight nylon encasement. The transparent material shows off her boots, stockings and corset. Mistress then ropes over the top, making a beautiful creation. She is then laid down and her throbbing cock revealed and edged with a vibrator and then a nylon stocking until she can't hold on and cums a big sissy cream load.

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Length: 22:00 Xdressed For The Part 10 Pics
 
 

Featuring Mistress Eloise

Mistress Eloise, wearing her red latex dress, is training her rubber doll Betty. She is reprimanded for not carrying out all her assigned duties and then ordered to clean Mistress' shoes as penance. Eloise decides to train doll's hole with a big strapon, starting gently and then pounding her in different positions as she becomes a fuck doll. Betty is then put in a tight, latex hobble dress and put on the bondage post, her hard cock teased and vibrated before being left ruined and humiliated.

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Length: 22:02 A Strict Lady’s Maid 6 Pics
 
 

Featuring Miss Eve Harper

Eve Harper is interviewing a new, cute maid, she is nervous but very eager to please. The maid is dressed in classic uniform with black boots, Eve gives her a full inspection. She notices the maid has a cute erection already, so she locks it immediately in a steel chastity cage and special silk panties. Eve then takes her through basic slave positions, making sure to punish any transgressions before she decides whether to take her on full time.

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Length: 39:09 Scolded & Smothered 30 Pics
 
 

Featuring Miss Jessica

Miss Jessica sets her sissy maid the task of cleaning the dungeon and will inspect her work when finished. The maid is hampered by the bondage chains, but she tries hard to follow her orders, stumbling and manoeuvring around the furniture. On Miss Jessica's return, she checks and is not impressed by the areas she has missed and decides to punish her. First by depriving her of breath by smothering her sissy face and then by punishing her over the bench with a firm spanking and leather slipper.

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Length: 32:19 Sissy Skool 31 Pics
 
 

Featuring Maid Sharon & Miss Melissa Taylor & Miss Ruby Marks

Miss Ruby Marks is in charge of her special sissy skool. She has called three of the girls back for detention, as they have been disruptive trouble makers, when she enters the class she surveys there naughtiness. Miss gives them a spelling test, the girls cheat, copying the answers and throwing bits of paper, so she decides to give them a summary punishment. One is sent to the corner in a dunce hat the other two bent over the desk and given a long spanking and belting. They are then put in bondage and the final girl is given a hard caning, to reinforce the need for their behaviour to improve.

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Length: 32:34 Dirty Dungeon Dollies 11 Pics
 
 

Featuring Lady Bellatrix

Lady Bellatrix is wearing her sexy latex outfit and has dressed two of her rubber dolls in matching dresses. She is going to have some hot fun with them both, inspecting their outfits before suggesting they grope each other, unsurprised at how quickly their cocks get hard. Mistress has a competition to see who can suck her dildo the best, cajoling their deep throat skills, impressed by how hard they are trying. Bellatrix rewards their efforts, putting them in the scissor position, telling them to rub each others stiff cocks, making sure she gives them some sexy frottage, loving the dollies moaning in desire. Once their brains are totally in subspace, she orders them to give her a sexy suck show, as they take turns in orally pleasing each other, as Mistress monitors their skills.

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Length: 23:23 Big Trouble For A Little Sissy 36 Pics
 
 

Featuring Mistress Nikki Whiplash

The sissy maid shows just how useless she is when she serves her Mistress the wrong drink. Bent over the Mistresses knee for a good spanking, she is also punished for not wearing regulation panties. A firm hand spanking is quickly followed by the hairbrush, the slipper and finally the cane. Her bottom soon resembles the colour of her dress. The maid must also be trained in how to suck cock and with the size of the Mistress's strapon, it doesn't take long before she's gagging on it.

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Length: 25:20 Submission Surprise 10 Pics
 
 

Featuring Lady Valeska

Valeska phones her long time partner at work and demands he comes home, as she has something urgent she needs to discuss with him. His mind is awash at what it could be, he desperately hopes she hasn't found his crossdressing clothes and pornography that he loves so much, his stomach rolling with butterflies as he journeys back. When he comes into the lounge Valeska sits him down and seems in a good mood, as she tells him he shouldn't be shy about sharing his sexual fantasies, she has her own as well, raking off her robe and revealing her superhot Dominatrix outfit. Charlie is shocked, as she tells him to kiss her boots and explains that their relationship will never be the same again. He will be dressed up femme at all times, will learn to take big strapon cock and become a fluffer the future manly lovers that she has decided to take from now on. He nods, already feeling his cock stiffen in his panties, as his new life as a she begins.

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Length: 20:15 Sissy Lock vs Sissy Cock 4 Pics
 
 

Featuring Lady Sara Borgia & Tiffany Real Doll

The stunning Mistress Sara Borgia, is having some kinky daytime fun with two of her hot sissy girls, Michelle and Tiffany. One is locked in tight chastity, the other has their desperate stiff dick ready to be played and teased with. Sara loves edging and playing with the two cocks, one locked tightly, the other throbbing, telling them both to massage her legs. The cute sissies are then commanded to touch and pleasure each other, Michelle on her knees guided in the art of her first cock sucking by Mistress. Tiffany is then given an amazing, edging handjob until she cums hard, the mess fed to the other sissy by Sara, as she laughs and humiliates her.

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