Free Sissy Training porn videos

Subby Hubby – Paris Trains Her Husband Part 5: Fucked Cuck

Paris Knight isn’t done training her husband to be the little submissive cuckold bitch she wants him to be. She knows the way to really get him to feel completely submissive to her, is to fuck him with a strap-on. At least, that is what some of the women at the gym told her, so she is going to be putting it to the test. Paris makes her submissive husband suck her big cock and get fucked by her…

Subby Hubby – Rikki Rumor’s Cuckold 4: Blowing The BBC | Release Date: Sep 7, 2017

Rikki Rumor wants that big black cock, and she is going to show her husband just how much she wants it by sucking it right in front of him. He has to watch even though he doesn’t want to, and feels such emotional anguish as she has someone else’s cock in her mouth that she enjoys more than his. She makes him get up very close to watch. Just when he thinks it might be over, she makes him…

Subby Hubby – Rikki Rumor’s Cuckold: Cuck’s New Life | Release Date: Sep 4, 2017

Rikki Rumor is masturbating in her room while her boyfriend is in the shower. He catches her and he gets upset that she is masturbating with her vibrator and she isn’t having sex with him. She tells him it’s because he lasts 20 seconds. They attempt sex anyway and he can’t get his tiny pecker hard for her. She sarcastically tells him how satisfied she was. Before he leaves for work, he tells her that a man named Jack…

Foot Worship, Male Insertions, Oral & Asslicking

Subby Hubby – Cuckolding The Perverted Stepfather MiniMovie | Release Date: Aug 7, 2017

Cameron is a super hot woman with a problem – her stepfather is totally perving out on her, watching her all the time, especially when she is with her boyfriend. When she actually catches him jacking off to her, Cameron confronts him and tells him that if he doesn’t do exactly what she wants, she is going to tell her mother, who will kick the perverted stepdad to the curb. Cameron knows she has the upper hand, so she…

Dirty Talk and Masturbation Instructions

Goddess Alexandra Snow – Feminine Fancy Trance | Release Date: Jul 29, 2017

This is a very special trance journey for the sissy, cross-dresser, or tranny in you– a slow progressive descent into the mind to find the feminine presence deep within. I will let you shed the layers of your masculinity and touch the sweet, sensual female that you know is lurking behind the scenes. I will assist you in transforming into her, experincing pleasure like a woman, dressing and preparing yourself, and finally culinating in an explosive climax. You owe…

Cuckolding, Oral & Asslicking

Subby Hubby – Vanessa Sixxx – My Stepbrother is a Sissy Bitch | Release Date: Jul 11, 2017

Vanessa is tired of her stepbrother Cody being such a jerk to her. Even when her step-dad orders his son to let her watch TV, he hogs the remote to watch a ball-game. Vanessa knows that for all his macho exterior, he is secretly a panty bitch who wants to smell and wear her panties. Vanessa comes up with a plan. She sets the webcam on her computer to record, then catches her stepbrother sniffing her panties and cross-dressing…

Mistress T – Big Kinky Ass Fuck

Watch this bound sissy slut take my big black cock.

Foot Worship, Oral & Asslicking, Strap-on

Nadia White – Step-Brother Becomes A Sissy Slut – Subby Hubby | Release Date: May 19, 2017

Goddess Nadia White comes home boasting about winning a recent cheerleading trophy, as her step brother Cameron has never won anything. Nadia goes inside to get ready to go to her friend’s house, when Cameron comes inside and finds her cheerleading outfit. Cameron starts putting on lipstick and a blonde wig and cheering. Nadia sneaks up on him and records him acting like a perverted version of Nadia on her phone. Cameron begs to do anything so that Goddess…

Subby Hubby – Poker Face – 3 Chicks 1 Cuck – Mini Movie

Esmi, Tristen, and Melanie are having fun partying, but with parents coming home soon, they need somewhere else to go. They remember that the local nerd boy, Eugene, is home alone for the weekend. The cruel girls decide to have some fun at his expense; they are going to make him into a chastised sissy bitch for their amusement while they use his house as a place to party! Eugene is so happy that hot girls are actually coming…

Dirty Talk and Masturbation Instructions

Humiliatrix – Mistress Kendra Convinces Your Woman to Cuckold Humiliate You

“It was me who encouraged your woman to start having sex with other men. I got her her to admit your many failings as a man, and I have convinced her to begin sexually dominating you, with my help. While she’s out cuckolding you tonight, I’m going to train you to serve her in your new role: as her submissive sissy maid…”

Subby Hubby – Jade Jantzen, Rikki Rumor – Rikki’s Revenge

Rikki Rumor is on the phone with her best friend Jade Jantzen. She is telling Jade that her husband cannot sexually please her and has failed again. Rikki tells Jade that she should come over and spend some time with her. Rikki’s husband comes home from work and is surprised when Jade comes to the house. He hasn’t met Jade yet but Rikki plans on the two of them getting to know each other really well. Rikki takes Jade…

Mistress T – Sissy Slut Cums While Sucking Cock

My sissy slut is being trained to LOVE sucking cock. Part of the brain washing is making her have an orgasm with a cock in her mouth. This is her FIRST TIME cumming while sucking dick! She’s not a pro yet as she’ll need to learn to suck cock proficiently even when sexually excited. Practice, practice!

Oral & Asslicking, Strap-on

Subby Hubby – Dava’s Cuckold Sissy Slut

Goddess Dava Foxx has a new sissy slut who serves her. Today, slut boy Toby is cleaning the bedroom while cross-dressing and wearing high heel shoes. Goddess Dava comes in and sees he has forgotten one thing. She applies bright pink lipstick to his mouth and then instructs him to get down on his knees and worship her perfectly manicured feet. He licks and sucks on Goddess’s toes. Goddess Dava gets rough with him by shoving her foot in…

Subby Hubby – Goddess Vivian Leigh Catches Peeping Perverts

Goddess Vivian Leigh is chilling at home when she hears a couple of burglars trying to steal her underwear. She catches them and threatens to call the police unless they do as she says. Goddess Vivian has them dance in front of her to prove who is the bigger fuck slut. Goddess Vivian Leigh has the winner of the dance off worship her feet. She forces him to lick the bottom of her goddess feet and lick them all…

Previous
1
…
4
5
6
7
8
Next