Sissy Training

Vanessa Cage’s House Boy



Studio: SubbyHubby
Cast: Vanessa Cage
Genres: Body Worship, Chastity, Crossdressing, Cuckolding, Cum Eating, Female Domination, Full Movies, Humiliation, Sissy Training, Strapon
Video language: English

Toby is desperate, about to lose his apartment his car is going to be repossessed he really needs a job and fast, he sees a strange ad that says houseboy needed must be willing to do everything I say, he figures what do I have to lose and goes on to the job interview, upon arriving he sees a beautiful hot blonde laying out by her pool topless on the phone he knocks on the screen she waves him in , he extends his hand and says I’m here for the job interview with an annoyed look on her face the goddess puts her hand up telling him to wait, then she stands up pushes him down to his knees and explains he must be willing to do everything she says, Toby agrees and she hands him a pink diamond studded collar and tells him put this on bitch and worship my feet, Toby looks confused, she smacks him and says do you want the job or not, he replies yes Goddess and starts to lick and suck her toes, Worships Goddess Vanessa’s feet like a good little slut puppy, after Vanessa is through she instructs the bitch to clean her pool and then meet her in the garage but to stop and put on the rest of his uniform, Goddess Vanessa walks into the garage and makes him spin to show off his new cucky boy outfit, She feels it needs one more thing, and puts lipstick on the bitch. Then instructs him to empty everything out of the garage and move it to the barn and after he is through to move everything back into the garage, Toby asks why? She says because I told you Too Bitch now get to worthwhile enjoying a masturbation session with her favorite vibrator, Goddess Vanessa Cage is interrupted by her new houseboy Toby, who informs Goddess that he has finished her chore of moving the contents of the garage to the barn. Unimpressed with Tobys work and annoyed at the interruption, Goddess Vanessa demands Toby move everything from the barn BACK to the garage! Frustrated and humiliated to be wearing a dress, lipstick, and heels, Toby trots off to lug all the equipment he had carried to the barn back to the garage. With this futile exercise complete, Goddess Vanessa notices the frustrated attitude of her houseboy and decides to see just how badly she can frustrate him. With her perfect pink pussy glistening under the pulsations of her vibrator, the divine Goddess rests her perfect ass on her bitchboys chest, his cries of frustration turning her on more and more. Amused by his longing, Goddess Vanessa toys with her pet, allowing him to get within inches, but not able to make contact with her womanhood. As tears of frustration stream down the useless cucky boys face, Goddess Vanessa is overcome with passion and convulses in orgasm on top of her helpless slave. Removing the vibrator from her tight pink pussy, Goddess Vanessa shoves her toy into Tobys slutty, lipsticked mouth and orders him to complete his chores WITHOUT dropping it. Bursting with frustration, Toby gets to work folding the laundry, obediently holding the Goddesses vibrator in his gullet as instructed.As Toby is dusting Goddess Vanessa Cages room trying to be the perfect houseboy still locked away in a chastity. She decides to have a little fun with him. Goddess Vanessa makes her new bitchboy stop dusting and asks him Do you want to fuck my tight pink pussy? Toby gets all excited and starts to get a big grin on his face till she pulls out a chindo and makes him strap it over his red lipsticked mouth and get on his knees. As this cucky boy gets to work pleasing his Goddess she moans in rapture. Goddess Vanessa makes Toby go faster and faster informing him this will be the closest he will ever get to my tight pussy. Once Goddess Vanessa has reached her climax she shoves Toby off and instructs him to get back to work cleaning her restroom. As her new houseboy is cleaning the toilet Goddess walks in and tells him he is doing it wrong. My houseboys dont clean like that, now open your fuck hole, as she puts in a toilet brush right in Tobys mouth. Now get back to work!!!Mistress Vanessa Cage has her new house boy sweeping the floors when she decides to give him a nice surprise or should we say a nice big surprise. Mistress Vanessa calls Toby and informs him that she is horny and wants to fuck, but wants him on his knees, eyes closed and waiting for her. Toby is so happy he doesn’t even hesitate. When Mistress Vanessa makes her bitch boy open his eyes he looks like a dear in headlights when Mistress shoves her 12 purple cock right in his pretty lipsticked fuckhole. After this cucky boy has lubed up Mistress Vanessa’s cock with his own saliva, she bends him over and begins to stretch his tight little man pussy. As Toby begins to cry and whimper like a little bitch, Mistress Vanessa reads out her list of chores that her new house boy still has to do as she fucks him with her 12 cock.Mistress Vanessa Cage has gotten her cucky boy a present, well its more like a present to help him do more chores. After giving toby his new ironing board and instructing him to clean all her clothes. Mistress Vanessa then wants him to cut the grass with a pair of scissors. As Toby is cleaning the living room again since last time he was interrupted by Mistresses 12 strap-on, Mistress Vanessa decides to reward her sissy house boy. First she teases him as he is locked away in a chastity device by dangling the key to his freedom and blowing on his locked up 2 dick. As his 2 dicklet starts to grow he is in pain from his chastity. Then Mistress Vanessa finally unlocks him and plays with his dicklet for her own amusement. Just before Toby is about to release his filth, Mistress stops and laughs and informs him that she is done playing with him and that he can jerk his own dick, but he better release his filth in his own hand and not a drop on her rug. After her cucky boy has done as told, Mistress Vanessa hands this sissy a blow-up duck to fuck and to use his own filth as lube and walks away. Oh no, it looks like this house boy forgot a chore. Mistress Vanessa returns with the trash Toby was supposed to dump and says since you didnt dump the trash, maybe I should and throws the trash all over the floor for this houseboy to clean up.

Format: mp4
Duration: 30:14
Video: 1280×720, AVC (H.264), 6356kbps
Audio: 126kbps



File size: 1.4 GB

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Amadahy, Cali Carter & Kenzie Taylor



Studio: BratPrincess
Cast: Amadahy, Cali Carter, Kenzie Taylor
Genres: Chastity, Masturbation, Humiliation, Cum Swallowers, Sissy Slut, Sissy Training, Spitting, High Heels
Video language: English

Princess Cali has had her pathetic slave in chastity for two months. Strict orgasm denial for sixty days has made the slave very desperate. Cali unlocks the chastity in front of her girlfriends, Amadahy and Kenzie. If Cali’s slave wants to cum in front of three gorgeous bikini Princesses, he’s going to need to grovel. He’s a loser and deserves to be treated like dirt. The girls stuff a pair of smelly socks in his mouth and spit in his face. Cali makes her slave look at his little penis. He is reminded of how worthless it is while the girls shove fingers deep into his ass. The slave has to humiliate itself masturbating in front of the hot girls. The girls surround him and say very mean things about all his inadequacies. He’s allowed to have an orgasm on the dirty floor, but he has to lick up his own cum. The girls spit on the floor and spit on the slave. The slave cleans all the cum and spit up from the filthy floor with its mouth.

Format: mp4
Duration: 8:01
Video: 1920×1080, AVC (H.264), 10235kbps
Audio: 124kbps



File size: 608.7 MB

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Thin guy disguised as a woman



Release Year: 2018
Cast: Brianna, Natalya, Chloe
Genres: Femdom, Pegging, Ass Fucking, Dildo Fucking, Humiliation, High Heels, Taboo, Sissy Training, Chastity, Brat Girls, Sissy Sluts, Strap-On
Video language: English

t Girl in School Watches Danni’s, Brianna, has been training him to become a sissy. Danni’s younger , Natalya, is helping with the training. Danni has been fully transformed into a sissy, complete with corset, makeup, high heels and pretty hair. Natalya has invited her friend, Chloe, over to watch. Danni thinks that Chloe is the prettiest girl in school. It is especially embarrassing for danni to be fucked like a girl by his in front of the prettiest girl in school. Chloe takes video of danni while he gets fucked by and is to suck his ’s dildo. She is going to show everyone at school what his and have made him do. When is done fucking danni from behind, it’s turn. Danni does not want to be fucked.

Format: mp4
Duration: 13:06
Video: 1920×1080, AVC (H.264), 9722kbps
Audio: 258kbps



File size: 957.6 MB

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Miss Elektra – Sissy Training



Release Year: 2018
Genres: Femdom, Feminization, Maid Training, Sissy Training
Video language: English

After the transformation from a slave into a cheap whore, the slave positions obviously need to be refreshed urgently. Is it because of the clothing that the slave confuses even the simplest basic positions?? Ok, he’s obviously just a little worked up and can’t think straight at the sight of the mistress. Miss Elektra has mercy on him and so the walking training can begin. After all, a prostitute should be able to present herself correctly at the curbside!

Format: mp4
Duration: 1:05:43
Video: 1280×720, AVC (H.264), 3873kbps
Audio: 184kbps



File size: 1.9 GB

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Tuesday, October 9th, 2018 Femdom, Feminization, Sissy Training No Comments

Train Sissy Slut With Huge Strap On Cocks



Cast: Kimber Woods, Raven Hart
Genres: Femdom, Humiliation, Sissy Training, Strap-On, Pegging, Gender Transformation, Chastity, Crossdressing, Dildo Fucking, Anal
Video language: English

Raven never wanted Marcello. She always wanted to have two . Instead of a second girl, Marcello came into her life. That’s ok. Raven will turn Marcello into the girl she’s always wanted. Thankfully, Raven has the help of her girl, Kimber. Kimber has always wanted a friend. She’s happy to help her mom make Marcello into the friend she never had. Marcello’s gender re-training will start now. Kimber and Raven have already locked Marcello into a pink chastity.

Format: Windows Media
Duration: 17:35
Video: 1920×1080, Windows Media Video 9, 9765kbps
Audio: 312kbps



File size: 1.3 GB

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Mom And girl Train Sissy Slut With Huge Strap On Cocks



Release Year: 2018
Cast: Kimber Woods, Raven Hart
Genres: Femdom, Humiliation, Sissy Training, Strap-On, Pegging, Gender Transformation, Chastity, Crossdressing, Dildo Fucking, Anal
Video language: English

Raven never wanted Marcello. She always wanted to have two . Instead of a second girl, Marcello came into her life. That’s ok. Raven will turn Marcello into the girl she’s always wanted. Thankfully, Raven has the help of her girl, Kimber. Kimber has always wanted a friend. She’s happy to help her mom make Marcello into the friend she never had. Marcello’s gender re-training will start now. Kimber and Raven have already locked Marcello into a pink chastity.

The woman and girl 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 friend’s house. Raven’s friend 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. Because Marcello does not have the proper number of fuck holes for a girl, they will have to train her ass to function for men like a cunt.

First, the woman and girl play dress up with Marcello, who will now be referred to as “Marcy.” Kimber is very excited to share her clothes with her new friend, Marcy. Kimber’s clothes are very provocative, but Kimber tells Marcy that men like provocative clothing on girls. In his new role as a sissy slut, his function will be to please men and do things that they like. Learning to wear revealing clothing for men is just a start.

Kimber and Raven are really pleased with Marcy’s transformation. They’ve spent enough time on Marcy’s new look, now, it’s time to train her to get fucked like a girl. Kimber and Raven spit-roast Marcy. She must learn how to suck cock while getting fucked from behind. This kind of sexual multitasking is foundational for a slut’s training. Raven begins the ass fucking with a large dildo.

Marcy’s new friend has an extra-large sized dildo, even bigger than her mom’s! Kimber thrusts the enormous dildo deep into her friend’s “pussy.” Marcy cries out. It’s too big! But Kimber and Raven insist that Marcy must learn to take it. She will thank them for the good solid training once she is earning her keep as a whore. Good whores do as they’re told. Marcy must learn to be a good whore. With Marcy flat on her back, Kimber fucks her ass while Raven fucks her throat. Her pink chastity is in full view. Marcy is well on her way to becoming an excellent sissy slut.

Format: Windows Media
Duration: 17:35
Video: 1920×1080, Windows Media Video 9, 9765kbps
Audio: 312kbps



File size: 1.3 GB

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Chloe Peruses The Stables



Release Year: 2018
Genres: Femdom, Humiliation, Sissy Training, Taboo, Chastity, Crossdressing, Behavioral Modification
Video language: English

The Brat Princess household has a good selection of slaves in the stables. Chloe wants to pick a good one to ballbust and use as a human toilet. Four slaves have been hooded and lined up for Chloe to select from. Brianna and Natalya help Chloe choose. Each slave has its own strengths and weaknesses, but which one does Chloe want? Chloe settles on a nice fat one. The girls unlock the fat one from chastity. Its body is so big but its penis is so small. Chloe kicks the fat one in the balls several times. Then, Natalya and Brianna get a turn at kicking it. After each girl gets a go, they lock the slave back in chastity and return it to the stables. Chloe congratulates herself for making an excellent choice in her selection.

Format: mp4
Duration: 9:12
Video: 1920×1080, AVC (H.264), 10180kbps
Audio: 248kbps



File size: 703.3 MB

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He wore a woman for him to face



Release Year: 2018
Cast: girl
Genres: Femdom, Pegging, Ass Fucking, Dildo Fucking, Humiliation, High Heels, Taboo, Sissy Training, Chastity, Brat Girls, Sissy Sluts, Strap-On
Video language: English

About Love Brianna thought about her lover all day. She is very appealing to fantasies about his machined alpha male body. Unfortunately, her alpha male can not come and enjoy her as she needs. But her boyfriend, danny, is at home. Danny is trained by his elderly friend to serve her as a bitch. Danny’s body does not look like his old woman’s lover, but since he’s the only available option, his face will have to do. Brianna goes to face the guy, portraying her best man-lover. Danny wears a tight corset, garters and stockings as part of his training. He is locked up in chastity, so it’s a treat for his old woman. Brianna uses a vibrator to make sure she has a good orgasm. Danny, acting like a naughty girl, tries to help her old woman. The maid hides her well-fed boy and tells her to go boom into her pussy so she can get out. If Danny can not return his woman, he will remain in chastity endlessly. Brianna pumps her hips until she reaches the climax. When she finished, Brianna puts his feet on Danny’s legs. Danny should kiss his old woman’s legs and thank her for being able to be useful. When Alfa Brianna appears, the tribute must answer the door.

Format: mp4
Duration: 8:04
Video: 1920×1080, AVC (H.264), 10204kbps
Audio: 237kbps



File size: 617.0 MB

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My desire to dominate you



Release Year: 2018
Cast: girl
Genres: Femdom, Pegging, Ass Fucking, Dildo Fucking, Humiliation, High Heels, Taboo, Sissy Training, Chastity, Brat Girls, Sissy Sluts, Strap-On
Video language: English

Brianna trained her young boy, Daniel, to become lifeless. She chose romantic fantasy to read Danielle’s material. Relevant literature is part of Daniella’s intellectual development, as he turns into the perfect crazy for his elderly fairy. Brianna calls Daniel into the room. Daniel was dressed, head to nose in complete dark clothes. She wears a pink satin corset and pink garters to hold her stockings. And, of course, the guy Brianna has a chaste chaste mood. When she approaches the lad, the Fairy corrects Daniel and reminds her that lipstick is very important for a good girl.

Format: mp4
Duration: 8:08
Video: 1920×1080, AVC (H.264), 9715kbps
Audio: 236kbps



File size: 592.8 MB

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Mercy of Her Hand



Release Year: 2018
Genres: Femdom, Humiliation, Sissy Training, Taboo, Chastity, Crossdressing, Behavioral Modification
Video language: English

Mistress Adria has complete control of her slave’s cock allowing him only one orgasm per month. Slave’s are meant to be kept in cages and on their knees and she makes sure to reinforce this by never letting him free. With his balls trapped to the cage in a humbler Mistress Adria slowly edges his cock to a long-awaited & mind blowing orgasm.

Format: mp4
Duration: 13:52
Video: 1920×1080, AVC (H.264), 11309kbps
Audio: 304kbps



File size: 1.2 GB

Tags: ,

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