Tag: Sissy Training


Subbyhubby: Vanessa’s Sissy Part 1: Foot Worship




Vanessa is training her man to be a sissy for her. Later she plans on dressing him but for now she wants her feet worshipped while she mostly ignores him and is on the phone with her friends, discussing going out to the club to get laid by real men. He must listen to this while he worships her. He knows he is nothing more than a cuckold.
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Humiliation POV: Extreme Bratty Giggly Humiliating Sissification Of A Loser


A rare find from the vault. A new, exclusive, never seen before clip featuring your favorite Goddesses! This clip features Chloe, Jocelyn, Dylan, Miss Tiffany, and Vina! Watch them degrade, sissify, and laugh at this lucky member!

These gorgeous Brats are going to completely sissify this loser. Isn’t he lucky? First he gets a collar and then he stands up so they can laugh at his little penis. They make him tuck it in between his legs so he looks more girly, lol! Omg there is sooooo much laughter and giggling in this clip!

Next they put makeup on him. He’s going to get a complete make over. Then they put his hair in pigtails. LOL! He looks so stupid and girly. Next he gets a pink wig. You can see from the look in his eyes how humiliated he feels. But the humiliation is only beginning. They dress him up in a bra and panties and heels, laughing at how stupid and pathetic he looks.

Next they make him stroke his little clitty like a girl through his panties! The Brats laugh so fucking hard! Oh my god wait til you see all the humiliating things they do to him. Watch them teach him how to shake his ass! This clip is truly epic! But this is only the first part. Come back tomorrow for part 2 and just Wait until you see what they do to him!
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Clubdom: Beat the Sissy


Nadia White and Goddess Valora are going to teach their sissy how to be an obedient slut for them. They decide he must earn their cocks by taking a nice whipping and paddling. Nothing makes them smile more than seeing the red ass of a sissy slut parading around the house as the sissy cleans and does tasks. Valora whips Gapin Gabriella while Nadia watches on, grinning. Both the women switch off paddling that sissy’s pathetic ass.
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Humiliation POV: Cotton Candy Brain Sissy Bimbo Pleasure Puppet Brainwashing


Brainwashing is the concept that the human mind can be altered or controlled by certain psychological techniques. Brainwashing is said to reduce its subject’s ability to think critically or independently, to allow the introduction of new, unwanted thoughts and ideas into the subject’s mind, as well as to change his attitudes, values, and beliefs.
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Clubdom: Fucked Sissy Whore




Kendra James and Hadley Vascara know that their slut needs a good hard fucking. They stroke their cock and Kendra gets very close and tells the sissy that he must take their cocks GOOD for them. They have the bitch bent over before he knows it, taking cock in both holes, hard and deep. The women show him no mercy as they pound him good and hard. He must take it like the owned whore he is.
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Humiliation POV Bratty Ashley Sinclair: You Want To Be Girly And Suck BBC Just Like Me


Bratty Ashley Sinclair

I love big black cock and so do you. I think I’ll teach you how to suck one. You’d like that, wouldn’t you? Because you want to be really good at sucking bbc. I know you do. I’ll bet you wish this big black cock was in your mouth right now. I wonder what’s turning you on more, watching me suck it or picturing yourself sucking it? LOL!
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Clubdom: Jean’s Punished Sissy Part 5




Jean Bardot continues to slut-train her sissy and today she is wearing the biggest cock of all of them. The slut BETTER take her cock! Jean makes the slut suck her cock and lube it up good with her spit. Then Jean bends the slut over but decides the slut needs a good paddling first. She gets out the paddle and gets to work scolding her sissy and paddling her slutty ass! Jean then fucks the brains out of her sissy good and hard like the sissy slut deserves.
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Humiliation POV Goddess Dylan: If You Can’t Walk In Heels, You Can’t Call Yourself A Sissy


Goddess Dylan

Most of you are foreign to walking in heels like a girl because you’re a clunky guy. You don’t know how to be dainty like a girl and how to sway your hips and walk sexy in a pair of heels. But luckily for you, you have me, Goddess Dylan, the most feminine Goddess of all, to show you how to walk in heels, sissy. You don’t want to walk like a man but you also don’t want to walk like some wobbly bambi who doesn’t know how to walk in heels. You don’t want to break your ankles and look like a fool now do you?

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Clubdom: Jean Bardot’s Sissy Training Part 2: Take Cock!




Jean Bardot is here to plow her slut with her cock so the slut learns what it means to be a real whore. Jean is excited to stretch out both the sissy’s mouth and ass so the sissy can take any sized cock Mistress Jean desires her sissy to take! The sissy struggles but eagerly accepts Jean’s enormous femdom cock in her slut-holes, wanting so badly to please Mistress Jean.
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Clubdom: Jean Bardot’s Sissy Training Part 3: Stretching For Sluts




Jean Bardot is on a mission to turn her sissy into a total whore for her. She is continuing his training with even larger cocks for the bitch to take. Jean knows its just as important to work the mouth as it is for her to work the male pussy hole. She relentlessly fucks him, training him to take it, showing him that she means business when it comes to slut-training him.
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Mistress Kandy – Sweaty little slut flogged and ordered to eat ass


Mistress Kandy has her slave secured by the wrists to the ceiling. She tells you that her sissy has done a good job today, sucking cocks and making her a lot of money, she cleaned the house and licked her ass after a workout. “There is always room for improvement though” she adds as she slides the panties to the side to reveal the slaves already marked ass. She gives her slut some solid slaps with her hand across her ass and then explains that during this beating she wants the slave to focus on the need to show the most enthusiasm possible when sucking cock. The man should see that the slave is happy to be between his legs, sucking him deep and hungering for the taste of his hot cum.
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Humiliation POV Goddess Carissa Montgomery: Lose Your Former Self And Reawaken As A Reprogrammed Cock Brained Sissy Faggot (Effects)


This is a really powerful sissy fag hyp n0 s!s video. So if you don’t want to be a sissy faggot, I suggest turning this off right now, as I will completely reprogram your brain, turning you into a sissy fag. I’m going to reprogram your mind so that you think and act like a sissy faggot. So if you don’t want this, press stop right now because you’re so fucked if you don’t. And once you’re under, all the words that I utter, will begin reprogramming your vulnerable brain. From now on, everything you do will be that of a sissy fag. From the way you treat yourself to the way you treat others, even your thoughts will be that of a sissy faggot. You’re going to be a brainwashed sissy faggot with no thought other than dressing up girly and being a complete fucking slut for cock. Don’t say you weren’t warned. You’ll lose your former self and reawaken as a reprogrammed sissy faggot. You’ll find yourself doing things you’ve only ever fantasized about. Isn’t that what you want? To have your walls taken down, your barriers broken? Of course it is. Cock, cock, cock faggot. I’m going to turn you into a cock brained sissy faggot.
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Mistress Nikita/Obeynikita: Barbi, Fuck My Heels




Barbi is such a slut for shoes, especially my 6 inch stiletto heels. I like to have them licked before I go to bed each night. This time I decide to allow my bimbo sissy sex doll some release since she’s been such a good gurl. I unlock my cock and let the bitch fuck my nylons and heels until she cums all over them. As you might have already guessed, she has to lick up every last drop and suck her cum out of my sheer black stockings.
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Humiliation POV : Cock Sucking Cum Slut Sissy Faggot Airheaded Bimbo Brainwashing Program




Imagine you’re lead into a dark room, and in the center of the room is a chair. You’re strapped down to the chair except for one hand which is left for your cock, to keep you horny and stupid. The door closes and a screen appears before you. Your brainwashing program is about to begin. It is a sissy faggot cumslut cock dumb braindead airheaded bimbo brainwashing program. You have no idea how long you will be there, and when you’re done, you’ll have no idea how long you were there. You begin to see the images on the screen, and you hear the programming voices of two sexy fembot brainwashing voices, one in each ear. This is that video… So put yourself in a chair, set the video to run on loop, turn off the lights, put on headphones, and jerk. I wonder how long you’ll be there…. You Will be turned into an obedient sissy girly cumslut faggot with no memory of your previous life…
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Brat Princess 2: Chloe and Sasha – Slave Whipped while Frightened Sissy Dances to Entertain Princesses (1080 HD)


Chloe and Sasha survey the damage they have done to their slave with a previous beating. His back is already heavily marked by the girls. But it isn’t enough to satisfy the sadistic Princesses. They want the slave to suffer more for their amusement. The slave complains that he is too sore to take another beating, but the Princesses do not care. They string him up anyway. Sissy helga attends Chloe. Helga does not like to witness the cruel beatings of the slaves from the stables. It frightens her. Chloe likes to keep helga in fear, so she makes the sissy watch. Soon, just having helga in attendance is not enough to satisfy Chloe’s cruelty. Chloe makes the sissy humiliate itself by dancing for her amusement while she and Sasha continue to beat the tethered slave. Unsatisfied by helga’s pathetic attempt to entertain, Chloe and Sasha decide to string her up and whip her next. Perhaps the sissy’s screams will be more amusing than her ridiculous dancing.
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Goddess Harley – Sissigasm Seminar


Ok listen up slave, I’m booking accommodations at the next porn convention and I need a couple slaves to go with me. Specifically, I need a loser that I can use at the 2 hour seminar I’m giving at the banquet room in the afternoon. If I choose you I’m gonna be passing you off as a sissy orgasm expert. I’m gonna dress you up like a ridiculous whore and shove you out on stage as the authority on sissy orgasms like a sissy faggot. Your gonna have to give them all the pointers on the two finger jerk off as well as all the super gay mannerisms. Ya know, like limp wristing in the throws of ecstasy… licking your lips like a hungry whore… batting your eyes while begging daddy for his alpha cock. All that stuff. Let’s practice!

Get your limp wrist goin on… or do you want me to put you in a metal brace and make your arms and wrists bent like a pansy for the next week. That’s what I thought now tousle your hair and show off that limp wrist as you tell the Audience what a pansy masturbater you are. Tell them how you masturbate like a sissy while staring at my pictures. Tell them… you say “I’m a sissy fag that likes to play with my sissy clit!” I love my pink panties.
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Humiliation POV Goddess Valora: Goddess Valora’s Degrading Sissy Test (October 22nd 2017)


So you think you have what it takes to be a sissy, do you even know what that entails? It’s a lot more than what you probably think. So I’m going to put you through a sissy test to see if you truly are a sissy. For this test you’re going to need a plate. I want you to pause the video and jerk off onto a plate. And then come back to see if you pass the test, lol.
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Subbyhubby: Paris Trains Her Husband Part 5: Fucked Cuck (October 20th 2017)




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 until she is satisfied. She doesn’t just fuck him for a short time, she really makes it go on and on and makes it count. Every minute that goes by, he feels more and more owned by her and like her little bitch.
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Brat Princess 2: Brianna – Mother Uses Sissy Sons Face to Get Off while Thinking About Lover (1080 HD)


1080 HD Brianna has been thinking about her lover all day. She is very turned on fantasizing about his chiseled Alpha male body. Unfortunately, her Alpha male isn’t available to come over and pleasure her like she needs. But her son, danni, is home. Danni is being trained by his mother to serve her every need as a sissy. Danni’s body looks nothing like his mother’s lover’s, but since he’s the only available option, his face will have to do. Brianna rides her son’s face while picturing her superior male lover. Danni wears a tight corset, garters and stockings as part of his training. He is locked tightly into chastity, so that the pleasure is all for his mother. Brianna uses a vibrator to ensure that she has a nice orgasm. Danni, acting like a disobedient girl, objects to helping his mother. Mother sets her sissy son straight and tells her to hum into her pussy so she can get off. If danni fails to make his Mother cum, he will be left in chastity indefinitely. Brianna rocks her hips until she climaxes. When she’s finished, Brianna puts her stockinged feet on danni’s face. Danni must kiss his mother’s feet and thank her for the opportunity to be useful. When Brianna’s Alpha comes over, danni must answer the door. As a good sissy, he must be submissive to both his mother and her Alpha. Danni worships his mother’s stockings until there is a knock at the door. Hearing the knock, he knows what he must do…
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Mistress Stella – Patreon Rip – Affirmations and Assignments [EMP EXCLUSIVE]


Mistress Stella is a pretty famous mistress that focus mainly in feminization/sissyfication. Their files are probably the best regarding audio production quality.
In mid 2016 she started a patreon campaign. For the 5$ tier, she does 2 categories of files, Afirmations and Assignments.
Clips range from 3 to 10 minutes and do what the name says. Every 2 weeks she puts up something new for the patreons.

This is a $5 Tier rip of Mistress Stella Short files til date.
The list follows as such:
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Humiliation POV Princess Kaelin:Confused, Broken Little Clitty Sissies Have To Finger Their Man Pussies


Princess Kaelin

Hello my little sissy bitch, I know how much you long to please me. I know that deep down in that little sissy heart of yours you desperately want to make me happy. And all you have to do to make me happy is to be the sluttiest little sissy you can be. LOL! Do you think you can do that for me?

I know that you rub that sissy clitty all the time. You’ve accepted that little thing will never be a cock. You were just born with a little clitty. There may have been a time when you were disillusioned and thought you were a man, but now you’re completely broken for me. You’ve accepted your life of being humiliated by me, because you know a little sissy bitch like you would never have a chance with someone like me. And therefore you may as well not be a man at all.

Now I want you to start fingering that man pussy for me. Little sissies have to finger their man pussies. You need anal stimulation along with rubbing your clitty in order to get off. Because that is the only way a little sissy slut like you should ever get off. So rub your little clitty like a good girl, I know what a horny little slut you are. Show me how desperate you are to cum. I want to hear you moaning like the bitch that you are as you are, all dressed up like a slut getting off to femdom internet porn! LOL! How pathetic are you?

Now bend over and spread your man pussy and put a finger inside. Fuck that man pussy, show me what a good little whore you are. The thing that sucks about being a sissy is that you’re not good enough to be a man or a woman. You’re just a pathetic confused fuck. All you have is me, humiliating you. You know that me making you fuck your little man pussy is the best you’re going to get. So you should fucking thank me.

Start fucking that man pussy deeper and harder slut. Show me what a good girl you are for me. Now rub that clitty while you fuck that man pussy. Put another finger in, really stretch yourself out. You like that don’t you? Of course you do because deep down you truly are a little sissy bitch. You Need it in the ass. You need me to help you fulfill your sick, perverted desires. Fuck it harder, hit your prostate. Your little clitty is so hard because you love it in the ass. You love fucking your man pussy you little slut. Now add a third finger. You’re a pathetic little sissy bitch, fucking your ass, rubbing your clitty, it’s so humiliating but you love it. And it’s what you deserve. I’m going to help that little clitty squirt. Get right to the edge, whore, as I bring you to an explosive orgasm.
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Subbyhubby: Paris Trains Her Husband Part 5: Fucked Cuck (September 20th 2017)




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 until she is satisfied. She doesn’t just fuck him for a short time, she really makes it go on and on and makes it count. Every minute that goes by, he feels more and more owned by her and like her little bitch.
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Humiliation POV Mandy Flores: My Denied Tiny Dick Crossdressing Sissy Faggot Cuckold (September 13th 2017)


Mandy Flores

I have all sorts of plans for you in your new life as my sissy bitch! You will serve me, my girlfriends, and my lover. Just get used to being my teased and denied bitch. I’m going to give you nothing in return for all the services that you do for me. Are you peeking up my skirt at my pussy? Get a good look because you’ll never be good enough to touch it or taste it, much less fuck it. Not a chance in the world! Because your dick is so fucking tiny! I’d never let it near my perfect pussy.

You are so pathetic. You don’t need pussy because you are one. And what do pussies need? Cock! Pussies want cock! Just look at my pussy. Isn’t it beautiful? I can get you to do almost anything with it. But you will never get near it. But you like being denied by my pussy. I know you’re jerking your little dick to it. What a fucking waste you are! You need to be locked up in chastity. That’s where sissies belong. You know it’s true loser. If you want to be my sissy and serve me then your cock will be locked and I will decide if and when you cum. You will suffer for me.

So do you want me to lock up your tiny, useless dick? Say it! Good bitch. Now wait here as I go change into another one of the outfits that you bought me. I look so fucking sexy and all you’ll ever get to do is stare and drool with your little dick all locked up. It’s so funny that you want to be my denied sissy. So I bought you a new wig and maid outfit so you can properly serve me. You need to feel completely degraded and humiliated.

And look what else I’ve got, a Huge fucking strapon! You’re going to be sucking it, LOL! And you’re going to flip up your dress to get rammed in the ass with it. I know you want that because you are my bitch, LOL! Just look at my cock. It’s so big and meaty. This is what a real cock looks like. Compare it your little thing. This is the size of my lover’s cock. I crave his dick an so will you. Soon you’re going to need a cock in your ass and your mouth! You’re a fucking whore.

I love that you keep my closet stocked with new sexy outfits. I’m going to put another one on for my lover. I love that you buy me the outfits that I fuck other men in. And in return, I’ll buy you some slutty outfits for you to get fucked in the ass in. This is your new life. I will be in total control of you. Tell me how much you want to be my live in cuckold sissy. With that tiny dick it’s the only sex life you could hope for. It’s a privilege you have to earn, watching my man fuck me. We’re both going to laugh at you and your tiny locked up dick as you’re dressed like a girl. And if you’re a good bitch, after I get fucked, I’ll squat over your face and squeeze my lover’s cum in your mouth. Or you can clean his cock after he’s fucked me. That’s the only way you’ll ever taste my pussy. You’re my bitch now. You’re completely worthless. Soon I’m going to have you sucking cock for me to earn money. And you will suck and fuck and give me all the money. So you better learn to love cum. This is the only life for you.
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Brat Princess 2: BP – Dannis Little Sister Given Authority Over Him Part 2 (1080 HD)




Putting a boy into chastity for the first time is a very exciting time in a young woman’s life. Brianna and family counselor, Lola, have gathered Brianna’s daughter, Natalya, and her friend, Chloe, for the girls’ first talk about chastity devices. Brianna and Lola are excited to introduce the girls to the world of Keyholding. Natalya has had some experience seeing her father in chastity, but is just now ready to start holding keys of her own. It will be great to start her off with her disobedient brother, danni, as the first boy she locks into chastity. Both Chloe and Natalya are very excited to start Keyholding. Both young ladies are so lovely, they will soon have many, many boys in chastity. Lola introduces the girls to a state of the art chastity called The Vice. It’s a product she highly recommends to the families who come in for counseling. Lola explains some special design features that make The Vice a good choice. After hearing about the unique anti-erection, anti-pull out mechanism, Brianna is enthusiastic to get her husband into a The Vice as well! Danni is then called into the room. Natalya reveals to her brother that she is ready to start Keyholding, and he is going to be her first boy in chastity. Danni does not want to go into chastity, and he does not want his little sister to hold his key. He’s rushed off into the bathroom anyway, and told to get into The Vice. When Danni re-emerges from the bathroom, wearing his new chastity in the color his sister has chosen, the women all gather round and gush. Everyone is very excited to see Natalya close her first lock and collect her first key! As Natalya collects her brother’s key, the women applaud. Danni looks hopeless. Danni is once again sent out to bring the car around. Once danni is out of the room, Lola recommends that danni be castrated. Chastity is a good start, but it’s just a start. Step one is getting danni into chastity. Step two is adding the locking mechanism of The Vice to punish unwanted erections with physical discomfort. Step three is removing the testicles altogether. Danni’s mother and sister start to plan his castration. Chloe can’t wait to attend, and Natalya wants to cut the cord herself. Brianna and Lola are all smiles at the girls’ enthusiasm. The clinic is booked up far in advance for castrations, but in the meantime, the women can start doing some family pegging training at home with danni. It will help get him used to his new life as a gelding and a sissy. Brianna plans a weekly schedule for her son’s peggings. Natalya is excited to help her mom train her brother, and Chloe can’t wait to humiliate him by coming over to watch.
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Brat Princess 2: BP – Dannis Little Sister Given Authority Over Him Part 1 (1080 HD)




1080 HD Danni’s mother, Brianna, and sister, Natalya, have been having problems with his behavior at home. They take danni to a behavioral counselor. Natalya’s friend, Chloe, comes along. Danni is made to stand in the corner while the women discuss what to do about him. Natalya explains to the counselor that danni has been very disrespectful to the women in the household, he even called her a “bitch.” The counselor observes that danni is having a hard time coming to terms with the fact that he is a beta male, and therefore inferior to the beautiful women in his family. He has been acting out. The counselor recommends that Natalya be given greater authority over her brother, so that he understands that throughout life he will always be subservient to beautiful young women. She recommends that Natalya begin to discipline her brother for the disrespect he has shown. Natalya immediately grounds her brother. The counselor thinks that grounding is a good start, but she encourages Natalya to punish him further. Natalya makes her brother get on his knees and kiss her shoes. Danni resists, but all the women insist that danni respect the authority given to his younger sister. The four women overpower danni. They make him go around the room and kiss all their shoes. Danni is embarrassed to lick the counselor’s shoes in front of Chloe. Danni has a crush on Chloe and does not like to appear submissive in front of her. The women make danni do it anyway. While danni is licking shoes, the women decide to sell danni’s beloved comic book collection to teach him to be more selfless. The money can go towards new items for his sister’s wardrobe. Danni objects. The frequent objections on danni’s part cause the counselor to recommend that danni begin to see her for hypnotherapy. The hypnotherapy will help danni let go of his own feelings, and make danni more compliant. The counselor also recommends that Natalya formally collar her brother. The collar is a symbol that he is in submission to his younger sister. Natalya eagerly puts the collar on danni. Then, danni is sent out to bring the car around. After danni has left, the counselor recommends a total gender transformation for danni. The gender transformation will be a multi-step process. First, they will put danni into a new, state of the art chastity device called The Vice. Then, they will begin cross-dressing and gender re-training him. Danni will never be a real man, anyway. He will make a much better sissy.
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