Sissy Training

Lift Up My Skirt



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

Raven Hart has just started recently dating Marcello. Raven asks her date to strip out of his clothes so that she can see what he can offer her. Marcello thinks it is odd and embarrassing, but he complies with the beautiful Raven’s request. Once Raven has stripped her date naked, she examines his body, to see if he is up to par. Marcello isn’t. In fact, he’s a bit of a disaster. His body is flabby, and his penis is too small.

Format: mp4
Duration: 10:12
Video: 1920×1080, AVC (H.264), 9816kbps
Audio: 148kbps



File size: 744.3 MB

Tags: ,

Chloe & Natalya



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

Danni is chilling on the couch at home, in his underwear, playing video games. Natalya, and her friend, Chloe, walk into the living room and find him on the couch being lazy and gross.

Format: mp4
Duration: 9:36
Video: 1920×1080, AVC (H.264), 10042kbps
Audio: 148kbps



File size: 716.4 MB

Tags: ,

Wrestle And Scissor



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

Danni is very wimpy and scrawny. The girls don’t understand how it can be that they are much bigger and stronger than him. The girls call danni into the bedroom, where they have been talking about him.

Format: mp4
Duration: 11:21
Video: 1920×1080, AVC (H.264), 9676kbps
Audio: 247kbps



File size: 824.6 MB

Tags: ,

Lizzy Spanked



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

Lizzy made a huge mistake. She asked Chloe is she could go to a party with her. Gross. Chloe would never be seen in public with Lizzy. It’s extremely insulting she would even ask. Chloe drags Lizzy into the living room by the ear, so she can voice her grievance to their housemate, Natalya. Natalya has a beef with Lizzy, too. Lizzy is supposed to organize all her lip glosses in a very particular way, but Lizzy left one of Natalya’s lip gloss slightly open. It could have dried out! Lizzy needs to be taught a lesson. Natalya takes Lizzy over her knee. She and Chloe spank Lizzy. Lizzy squeals in pain. It’s very humiliating to be spanked by her housemates. Lizzy’s pale little booty gets red. Chloe threatens the belt next time, and reminds Lizzy that she’s lucky to be spared that for now.

Format: mp4
Duration: 7:54
Video: 1920×1080, AVC (H.264), 10188kbps
Audio: 286kbps



File size: 606.2 MB

Tags: ,

Dont Make That Stupid Face



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

Chloe is mad because she told danni to lick her shoes clean before she put them on, and danni didn’t do it. Now he’s in trouble. Chloe makes danni lay on the floor and lick her shoes. Danni is humiliated. He rather lick her shoes in private, without Chloe watching and judging. But danni doesn’t get a choice. He has to do what Chloe says or she will get madder at him. Chloe makes danni crawl back and forth across the room after her shoes. That’ll teach him a lesson. From now on, he better always do what she says. Danni is in love with Chloe, and tries to do everything to keep her happy. But loving a beautiful girl like Chloe can be expensive. The deeper he falls in love with her, the more costly his feelings become.

Format: mp4
Duration: 11:19
Video: 1920×1080, AVC (H.264), 7998kbps
Audio: 269kbps



File size: 685.7 MB

Tags: ,

Isabella Nice



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

Princess Isabella wants to have an orgasm. She calls, fluffy, in from cleaning her room. Isabella tells fluffy to go down on her. Fluffy isn’t sure that it’s ok to lick.

Format: mp4
Duration: 9:21
Video: 1920×1080, AVC (H.264), 10063kbps
Audio: 148kbps



File size: 699.3 MB

Tags: ,

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

Tags: , ,

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

Tags: , , , ,

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

Tags: , , , ,

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

Tags: ,

Tuesday, October 9th, 2018 Femdom, Feminization, Sissy Training No Comments
July 2019
M T W T F S S
« Jun    
1234567
891011121314
15161718192021
22232425262728
293031