Cali And Kenzie – Sissy Trained To Take Cock With Machine Fucking

Kenzie flips through a publication while her sissy is fucked by machine. The sissy has been strapped into a stockade and is completely helpless as its ass is pounded by the motorized dildo. Kenzie ignores the sissys whimpers as she reclines on a pink chaise. Cali drops by to visit. Shes equally interested in the magazine Kenzies been leafing through and joins her friend on the chaise for a cuddle. The friends chat about the publication and talk about nail salons, completely ignoring the sissy in training. Kenzie shows Cali how shes been wearing the sissys chastity key for two months as part of its training as well.

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Goddess Alexandra Snow – Ride My Dick, Sissy

First time seeing a dominatrix? I thought so. You’ve got “nervous sissy bitch” written all over your face. You even came wearing women’s lingerie under your street clothes. Isn’t that just precious? Well if you want to be a real sissy, you’re going to have to learn to take my cock in your sissy hole. But I’m not going to bend you over and fuck you from behind. No, that sounds like too much work on my part. Instead, you’re going to sit on my cock like a good little sissy and look right into my eyes as I’m fucking you. I hope you’re lubed up, sissy. You’re going to be riding this cock until your legs give out.

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Mistress Lola Ruin – Sissy Suck And Fuck

So sissy bitch, you’re back for a little more training, and I think it’s time you graduate to the next level. You have already perfected the art of a sloppy blowjob, so let’s start with that. I want you to make sure you get My cock good and wet, ready to slide into your tight little virgin pussy for the first time! Don’t you love the thought of Mistress taking your anal virginity? I can see you getting wetter and wetter whilst you wrap your lips around My beautiful cock. Now, turn around, bend over and spread those cheeks.

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Sissy Whores Temptation Pt 2

Asia Monroe puts on her harness; she’s about to ride this Sissy and make him take girl-cock. He holds his cheeks open to receive her fingers then she mounts him, making the nervous sissy slut moan like the girl he is. Asia turns the slut over onto his back to pummel in deeper, making him moan even louder until he is raw from the fucking. And just as they’re bout to finish, they are caught in the act by his Pimpstress Sonya.

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Sissy Whores Temptation Pt 1

Sissy Whore Gabriella is in trouble. Mistress Asia Monroe approaches him while he’s out hustling for his Mistress. She tempts Gabriella with money so she can have time together alone. Asia makes Gabriella suck a dildo and uses the opportunity to convince him to be her bitch instead of Sonya’s. He gets lost in the throes of passion even though he knows better. Will Asia Monroe succeed in her plot? Let’s find out what happens.

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Jasmine Mendez – 2 Cocks 1 Slut – Sissy Slut Training

Today Mistress Tangent & I came together to train Sissy Rebeca which we both co-own and my Assistant recorded. You lucky bitches get to watch it all here, You’re so welcome. I love to watch newbie sluts choke up on my cock with lots of throat cum. We always have so much fun together.

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Jasmine Mendez, Mistress Tangent – Sissy Sticks

Jasmine Mendez, Mistress Tangent – Sissy Sticks. Keywords: Female Domination, Free, Femdom, Dildo Sucking, Strapon, Strap-On, Strap on, Dual Domination, Double Domination, Latina, Mistress Tangent, Tangent, Mistress, Jasmine Mendez, Sissy Slut, Sissy, Sissy Training.

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Lola Fae – Last Fuck Before You’re Sissy Eunuch

Lola Fae is at home smothering her slave’s face with her crotch when she gets a call from her favorite stud. She was supposed to have some big dick come over and fuck her right, but he canceled. Lola decides to make do with her slave. Lola gets so worked up she cums on his cock, then climbs off of him. She sits on him, grips his aching blue balls hard and talks about possibly popping them in a vice. His balls ache and are so sensitive she gets him to beg her to take them from him with just a little squeezing.

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Latex Sissy In Extreme Rubber Bondage

Don’t think mistress Kim is soft for a lovely latex Sissy. After makeng them beatyfull she packs them inheavy rubber nd makes them suffer in strict bondage. An other HD Top video. Mrs Kim is not an actor, shep lays only for real! She is a real fetishist and loves to play with her willing objects. She milks them using the serious kit.

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Mistress Ariel Caning The Sissy Slave

Mistress Ariel’s slave is a nasty boy, wearing a corset, sexy stocking and high heels, while Mistress Ariel canes his ass brutally. She wants to teach him a lesson while he is wearing these women’s clothes, working her cane on his ass.

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Oubliette Films – Sissy Spitroast part 1

This touchy feely little slut better be ready as Mistress Serena and Bonnie Brown set to giving her a lesson in manners! Bonnie gagging the slut on her strap-on as Serena sets to ripping apart sluts ass with a good hard fucking! The dirty little whore is kept busy, all holes filled as she is brought to the brink of tears! Mistress Serena/Goddess Gynarchy has her sissy slave on all four on a fuck bench, she fingers his ass and fucks him from behind with a strapon while the slave blows Bonnie Brownn’s strapon.

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Sissy Fuck Toy Surprise

Vanessa Vixon kicks her sissy with her high heel shoe a little, then squeezes and slaps her sissy in the balls hard. Really hard. The sissy’s cock is rock hard from Vanessa’s sexy teasing, which makes Vanessa want to crush her sissy balls into nothing.

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English Mansion – Spurting Sissy Sucker

Tiffany Doll in her pretty pink sissy clothes, is waiting for Savannah Sly and Miss Vivienne, who arrive wearing beautiful stockings and suspenders and two massive strapon cocks. She is told to worship the long, luscious legs, the feel of the nylons on her hands and lips making the chastity clad cock strain. The ladies then get her to suck the big strapons, taking turns to ram it into her mouth and throat, the pink lips stretched wide as they use the sissy. Tiffany has done such a good job, they release her from the chastity device, spreading her legs on the couch and deciding to milk the big dick that is suddenly protruding, spoiling the line of her outfit.

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English Mansion – Tranny Sissy Baby

Three gorgeous Dommes of the English Mansion make new sissy slut baby training – Mistresses Sidonia, Lady Nina Birch and Mistress Nikki Whiplash are enjoying a pre-dinner drink in the dining room of the English Mansion. They have one tranny slut under the glass table to rest their feet on and humiliate plus their newest maid trainee for trial. The maid soon shows her inexperience with bad manners and slovenly behaviour, much to the disgust of the mistresses. They decide to retrain her, first as a humiliating sissy parading around for their amusement, then she is taken all the way back to the beginning of her training and dressed as an adult baby, all ready to start her lessons again.

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Mistress Suki – Good Sissy Milking

It makes a pleasant change when Mistress Suki’s sissy slave has been good, so Mistress shows her generous nature in releasing her sissy slut from chastity and allowed her to orgasm; however, sissy is told in no uncertain terms that from now on, the only time she will be allowed to cum is when her Mistress is sitting firmly over her face.

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Mistress Nikki Whiplash – Sissy Slutbag

Miss Vivienne L’Amour’s sissy slutbag is strapped down to the fucking bench, ready to have her sluthole with all our toys and, Fetish Liza and I waste no time in plugging up the slut’s ass as Mistress Vivienne fills her mouth with cock, then we work through bigger and wider toys to get that hole stretched really wide, ready for a good hand milking. I really loved shooting this video, these ladies are such fun to play with and we didn’t stop smiling as we ruined our victim’s sluthole.

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Mistress Nikki Whiplash – Epic Sissy Spanking Part V

Finally, Chloe and I reach the end of our epic sissy punishment session! With a bit of face slapping and humiliation thrown in for good measure, there are only the really big, thick canes to go before we are finished punishing our sissy’s bottom – which looks like it is very tender by the time we’re done!

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Sissy Maid Cleans Up Our Boyfriends Mess

Princess Carmela and Princess Lilly command the sissy maid to clean up the mess that their boyfriends made at the party that it was not even invited to. LOL! To make it even more entertaining they dress the sissy maid up in slutty red high heels, lacey panties, and matching bra.

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Goddess Alexandra Snow – My Sissy Step Son – Strap-On Fun

My sissy step-son is home from college for spring break. My wife and I have missed him so dearly while he’s been gone. We haven’t had any opportunity at all to fuck my little sissy step-son. But now we have a whole week with his precious little hole. My step-son knows how to take care of his step-mommies.

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Goddess Alexandra Snow – My Sissy Step Son – Caning Punishment

My wonderful sissy step-son is home from college and has taken to doing all of the house chores. Unfortunately for him, his work has been sub par. His beautiful new Step-mother Talia Tate has found some dust where it should be clean. Now no step-son of mine is going to be a lazy maid. So it’s time to teach him a lesson. A few strokes with the cane should clean up his act.

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Naomi Swann – Punished Sissy Ass

Mistress Naomi’s vacation rental has come with its very own sissy maid for her personal use. Within the first day of her vacation the sissy has already failed at bringing lunch at the proper time. He needs to be taught a severe lesson that will leave his ass a beautiful shade of purple as Miss Naomi Swann breaks out her implements. He will be crying for a 2nd chance to prove his worth by the time she is done marking up his sissy ass.

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Jewelz Blu – Sissy Stretcher

Mistress Jewelz Blu bends her bitch over to finish breaking in his greedy sissy ass. His only purpose will be pleasing cock of all shapes and sizes by the use of his hungry holes. No hole is left un-fucked as Mistress Jewelz Blu mercilessly destroys him a new one with her thick, strap-on cock. She wants him to continue sizing up his fuck-hole and will stop at nothing until her fist slides in with ease.

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Amadahy And Jade Indica – Sissy Whore Gets Out Of Chastity

Its time for Jades sissy to be milked. Amadahy is invited to share the sissy-girl. The sissy follows the Princesses into the living room from where she is kept. Her frills are lifted to expose her chastity. Her clit is swollen and her balls are full. Both Princesses tease the sissys chastity.

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Amadahy And Mia – Turn Danni Into A Sissy

Amadahy and Mia want to start sending danni on dates. In order to do that, he needs to be able to pass as female. First, the girls tape danni’s cock and balls back between his legs. After danni has been taped and dressed in his bra and panties, the girls apply his makeup. The girls make him practice speaking in a high and soft voice. The girls spray danni with perfume and then dress him in a sexy dress. They add a beautiful, soft, blonde wig to complete the look. Danni makes a very pretty girl because he is already very small and slender.

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Mackenzie Moss – Enslaved Sissy Doormat

Men just don’t understand what it means to be a woman wearing heels all day and wanting nothing more than to have their feet pampered upon arriving home. Mistress Mackenzie shows her sissy exactly how it feels to be a woman as she makes the bitch put on a pair and prance around like the slut he is. All sissies need to have their mouth filled as Mistress Mackenzie Moss makes her bitch open wide for her sore feet to be shoved inside. She needs them fully pampered after a long day and no better way than a sissy’s tongue to get the job done!

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Mackenzie Moss – Sissy’s Last Orgasm

Mistress Mackenzie Moss is giving her sissy slut one final orgasm before a life of permanent chastity begins. She isn’t always a cruel Mistress as she wants her sissy to have completely empty balls before the slut is denied forever. She makes her sissy show her his moves as he humps and fucks her hand one final time.

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Mistress Susi – The Sissy Fucked From Behind While Sucking Cock

Dressed in her skintight latex leggins with a black strapon, the german fetish dominatrix Sissy is ready to take her sissy from behind, while the sissy is allowed to suck the shy rubberslaves cock. This took the Rubberlady all of her convincing power, to have the new slave encased in full latex, give his cock to the feminized sissy slut. Nevertheless, the Sissy is doing so well that the shy slave cums.

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Kimber And Raven – Mom And Daughter Train Sissy Slut With Huge Strap On Cocks

Kimber And Raven are ready to help prepare Marcello for his new life as a girl. To continue his training, he will be shipped away to Raven’s ’s house. Raven’s runs a home for sissies, where to earn their keep they are whored out on dates. In preparation, generously, Kimber and Raven are going to help Marcello learn how to take very big cocks.

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