Tag Archives: Sissy Training

Humiliation POV Princess Kaylynn: You Are A Sissy Fag Who Loves Cock And There’s Nothing You Can Do About It

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Princess Kaylynn

When are you going to finally realize that you’re a sissy? I brought a toy for you to play with today. I want to see you suck this. I love degrading you. I want to watch you take the whole nine inches all the way down. Suck it sissy bitch. Can you handle my big cock? I’m going to make you gag on it while I laugh at you. I have such disdain for sissies like you. Now kiss my perfect ass and thank me for allowing you to suck on my strapon.

Lick it all over like it’s a cock. Show me how much you like it, show me how much it turns you on. You are a sissy, you are a fucking fag who loves cock and there is nothing you can do about it. Isn’t that right? You worship big cocks. Now keep sucking on my cock while you stroke yours. Suck and stroke you little sissy, while I laugh at you. You are a sissy cocksucker and you know it. Look at what a good cocksucker you are!

Look how big this cock is next to my heel, doesn’t that make your mouth water and your cock throb? Of course it does, you’re a faggot who gets hard by sucking cock. God you’re so stupid and pathetic. Sucking and stroking. I hope you know how pathetic I really think you are. You’re not a man, you’re a sissy cocksucker faggot. And you love it. Now take it deeper loser. Gag and stroke for me while I laugh hysterically in your face, faggot!

This is your favorite thing to do, isn’t it sissy? You love sitting alone in your room sucking on a big dildo while I degrade the fuck out of you. Worship, tribute, adore God Kaylynn. You know you love it sucker!
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Mistress Nikita/Obeynikita: Candi Cums – WMV

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fuck hole cum-dumps… I mean really (not just on video!).

I make Candi suck my Barbi doll for a while and then I strap up to fuck Candi’s ass-pussy so she’s got a cock in both holes. Once I’ve had enough, I instruct Barbi to milk Candi from behind while I finger her gaping sex pot. The slut gets so hot and bothered she can’t control herself — she sprays her warm load all over Barbi’s bedspread without permission! Barbi is such a cum whore now she immediately coats her fingers in Candi’s cum so she can suck it off. Then I feed the slut a little more sissy goop with the same gloved finger I stuffed up Candi’s fuck hole.
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Subbyhubby: Dava’s Cuckold Sissy Slut

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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 his mouth and sitting on him making sure he does his job properly. She tells him that this is the start of his new life in servitude. After Goddess Dava Foxx’s sissy slut Toby finishes worshiping his Goddess’s feet he has a chindo strapped to his face and he better get to work fucking her to orgasm. Toby freeze’s still, intimidated by such a dominating Goddess. Goddess Dava Foxx grabs his head and starts to grind on the chindo yelling fuck me harder bitch boy. He tries his best to please his Goddess, but fails like the miseralbe sissy slut he is. Goddess Dava instructs him to fetch her red vibrator so she can show him how to properly please a woman. Goddess Dava Foxx shows her sissy slut Toby, his chastity key and reminds him why he is locked up. Toby’s tiny cock is useless! She shows him the finer points on how to please a real woman and tells him that this is what has replaced him, A red shiny 8″ inch vibrator. She holds it on her wet pink pussy then turns it up and starts to moan louder as poor Toby’s little dicklette strains inside it’s tiny cock cage. Goddess Dava Foxx starts to have multiple orgasms, as Toby drips pre-cum all inside of his chastity device. After she has cum many times, she shoves her red dildo in his slutty little mouth, just to give him have a little teasing taste of a pussy he will never deserve to have. Goddess Alexis Fawx has brought home a date and introduces him to Toby, the cuckold sissy slut. She shows Toby the chastity key hanging around her neck and reminds him of his place, then instructs him to get her date hard so she can be fucked by a real man. Toby is made to jerk of Alexis’s date while she rubs her pussy and tells him to lick her date’s balls and to stroke his cock faster. Alexis loves the power she has over men. Finally her date is pounding her pussy hard giving her multiple orgasms as she makes her sissy slut watch and lick her feet. She starts smacking him in the face as she cums one final time, then instructs him to clean up all of her date’s filth from her pussy. Toby slurps it up like a good cucky happy to be included in Goddess Alexis’s sex life. Goddess Dava Foxx loves humiliating her cuckboy Toby. She makes him lay down with her new boyfriend standing over him as she strokes his big hard cock and compares it to Toby’s small dicklette. Goddess Dava Foxx tells Toby he needs to beg for the cum as she keeps stroking her new dude’s dick right over Toby’s pathetic face. Finally the boyfriend dumps a huge thick white gooey load all over Cuckold boy Toby. Dava puts Toby on his knees in front of her new man and makes him say thank you for the load of filth. Goddess Dava Foxx’s sissy bitch Toby is cleaning the room when she strolls in wearing a 12″ inch pink Strap-On cock. She orders him to drop to his knees, takes out some dark red lipstick and tells the little bitch boy to pucker up. Goddess Dava puts the lipstick on his slutty little mouth. Then Goddess Dava writes Cum Whore on his chest and then tells him to suck her cock, better yet gag on it. Toby swallows the whole dick and then begs her to fuck his cuck pussy. Dava loves the control she has over men and grabs the cucky boys pantyhose and rips a hole right in the back, so she can shove her hard cock up his slut hole. She fucks him hard and flips him over for more, Tobey bites down on a pillow as his goddess Fucks his cuckold slut hole even harder.
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Goddess Vivian Leigh Catches Peeping Perverts (ENTIRE MOVIE)

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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 over like a good little fuck slut subby. Goddess Vivian Leigh pulls out her strap on out and has her little subby bitch start to suck on it. She tells him not to be scared of her cock, to enjoy it. Goddess Vivian has him put the whole thing in his mouth and get it nice and wet with his spit. Goddess Vivian Leigh has her subby bitch bent over when she lines up her big wet strap on cock with his tight ass. She slides her big black cock deep into his subby ass.
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Subbyhubby: Vanessa Cage’s House Boy (Full Movie)

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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 ecstasy. 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.
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Humiliation POV: Dumb Braindead Airheaded Sissy Bimbo Brainwashing

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This is a 40 minute long, intense brainwashing clip that takes you on a journey so deep, you will never return. There is no way to reverse this as it has been designed to effect you permanently. So don’t resist as resisting will only make the effects stronger. You are trapped in this reality and your mind is completely empty making it easy for my words to penetrate your subconscious. Good girls like to listen and obey.

Men love silly bimbos. Intelligence is not attractive to real men. Real guys love braindead bimbos who are too stupid to think twice before dropping to their knees and getting their pretty faces fucked by big hard cocks. Being dumb is fun. Good girls giggle every time they have a sissy thought, giggling is so arousing. Every time you giggle you become more of a mindless airheaded bimbo. Remember the dumber you are the more guys will want to fuck you. Where most people have a functioning brain in their heads, all you have is a big ball of fluffy pink cotton candy. Cotton candy cannot think so there is no reason for you to try to use your pink cotton candy brain to think. Good girls want to shut of their minds completely and be overtaken by my words and thoughts of giggling and dressing sexy and sucking big cocks. Good girls love to be stupid and mindless. All you want to do is giggle and suck big hard cocks and eat as much cum as you can. Every drop of cum you swallow makes you a tiny bit dumber. So you can imagine how you will feel after sucking a dozen cocks and swallowing all of their loads. Your mind is empty other than giggling and sucking cocks in your sluttiest outfits. You are a slut and sluts are dumb. You are cock dumb. You want to be a brainless bimbo whore. You want to be a faggot feminine fuck toy for men to play with. This is all being implanted in your subconscious and there is nothing you can do about it and it will never go away. Even if your conscious mind starts to forget the seeds have been planted to so deep into your subconscious that they can never be removed. You are a brainwashed sissified bimbo. (This small description barely does justice to what you will hear and feel when you watch and listen.)
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Cruel Girlfriend: Makeup Assignment For Sissy Sluts

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This is a tutorial to help you prepare for your first cocksucking experience where I show you how to achieve the perfect look for your real man to blow his alpha load all over. It’s important for a real man to have something pretty to look at when he’s jerking off or getting his cock sucked so as a sissy it’s your responsibility to make sure he has that perfect view. We’ll start with your eyes because to enhance the humiliation of sucking on a real-man’s cock a sissy needs to maintain eye contact. When a defeated sissy is kneeling in front of a real man, with a huge alpha cock forcing its way into her throat she must look up at her master through her thick false eyelashes into the eyes of the stud who is emasculating her. Your eyes need to look pretty for him so let’s make sure they sparkle for him. Next, we need to give your real man something nice to put his cock into – a perfectly painted cock-sucking mouth. Your lips should look bright and glossy with thick layers of the prettiest shade of lip-gloss. Your real man wants to have the evidence of his conquest over you smeared all over his thick stud cock and balls so you’re going to make sure you have plenty of lipstick on your lips for him. Finally, he wants to see the shame and humiliation of your predicament written all over your face so we’re going to add some extra blush to your cheeks. You’re going to look totally ashamed of yourself as his cock pushes into your sissy mouth.
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Goddess Alexandra Snow – Your Gender is Sissy

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Let’s get one thing clear, my dear. You’re not a man. Your desire to be dressed up and humiliated, made to wear women’s clothing, stockings, heels, makeup.. This obviously lacks all aspects of masculinity. But if you think you’re a woman, think again. Women are beautiful, graceful, sensual, and fine– you are not. Your gender is sissy. You’re something else, the chimera of the sexual world, made up of all these different parts. A man’s equipment but a woman’s desires and a slut’s need for humiliation. Fortunately for you, I know how to train the sissy and perfect it…
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Humiliation POV Kelle Martina: Mind Melting Sissy Re-Education (Effects)

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Kelle Martina

What you need is to be completely re-educated. I know that deep down inside, you’re a sissy. A sissy is a man who’s been reduced to a feminine place. Chastised, dressed up, completely erased of any maleness. But remaining male, remaining humiliated in that state, not fully transitioning over. And what I want from you, is for you to go deeper. Listen to my voice, relax your mind, let yourself be completely taken over by feminine energy. Listen and focus on the pretty sissy bow on my bra.

Focus little sissy, don’t look away as I sway back and forth. Your mind completely melting away, becoming my good little sissy. Know that your maleness is repulsive to me, I want you pretty, I want you feminine. Now think about your male clothing, they’re so boring, and the fabrics are so rough. They’re not silky and lacy. Now I want you to think of your dream sissy closet. All the soft fabrics, the pretty colors, the panties, the stockings, short tight skirts, high heels. So pretty, just imagine all the beautiful sissy clothes that feel so good against your body. You’re displeased with your body right now, it’s not feminine. You want the sexy curves of a female. You want all of those things, the pretty clothes, the curvy body, all atop those sexy high heels.

You want to be sex on legs in the highest heels you can walk in, swaying your hips back and forth. You want that with every fiber of your being. You can feel it in between your legs when you touch it. You want to be fucked and penetrated and used like the slutty sissy that you are. You want to please a man properly. You want to please, you want to be a submissive, beautiful female. You want to toss out your ugly male wardrobe and begin building your new beautiful sissy wardrobe filled with sexy clothes. I’m going to turn you from a good boy to a good sissy. You wanna go all the way. You want to completely transform into the sexy sissy of your dreams. You can feel your mind changing, imagining this life that you can create. I’m giving you the sissy life that you want, that you deserve. You can do it, you will do it, for me.
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Humiliation POV Princess Lacey:Leave Your House Sissy, Leave Your Old Self Behind

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Princess Lacey

Well sissy, this has been going on for far too long, and you know exactly what I’m talking about. You get all dressed up like a slutty sissy, for what? To sit around your apartment all by yourself? Not anymore. I’m going to put an end to that. I know you’re dressed up right now as you’re watching this because you truly are a sissy. So it’s time to be your true self, out in the real world. I want you out there strutting around like a sissy all over town. I want you exposed to everyone.

You are going to do exactly as I say, you are my sissy after all. So I want you to put on your sexiest, most feminine outfit. I want you dressed from head to toe, from your heels to your wig, makeup, stockings, panties, a short mini skirt, you know the look you just love. Get really slutty and girly for me.

Now that you’re looking like my pretty sissy, I want you to go stand in front of the mirror and take a good look at yourself. That’s who you are. Just look at yourself, there’s no denying it. Now I want you to say, “I am a pretty sissy and I’m ready to let the world know exactly who I am.” Take that in.

Get ready, you’re going to leave your house and leave your old self behind. When you open that door and step outside dressed like a sissy, you will feel so liberated. And you will thank me for this. You’ve been sitting alone, dressed up for years now. Those days are over. I want you out there. I want this done today. I know you feel ashamed, but don’t. Don’t give a fuck what anyone else thinks, just be who you are. It will be such a relief. It’s a different world now, you don’t need to be ashamed anymore. You need this so badly. This is who you really are. And while you’re out I want you to go shopping for something sexy dressed as your sissy self, your real self. And when you come home, you’ll be on your knees thanking me, after your first experience out in the world. Fucking liberate yourself, expose yourself to the whole fucking world.
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Mistress – T – Fetish Fuckery: Tease For Denied Sissy Cuck

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You are my sissy cuckold, you don’t get to fuck me. You just get teased & denied all the time while I humiliate & degrade you. Sit there & keep your dicklet tucked into your panties as I play with a real cock. Look at the size of him! He’s so much bigger than you. I know how crazy you are for boots so it’s fun to tease you with those too…& further humiliate you by making you clean up all that cum at the end. Awwww…poor sissy bitch. How does his cum taste when your balls are so full & blue? Ha ha
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Humiliation POV Princess London Lix: Cock Worship Training, I’m Conditioning You Faggot

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Princess London Lix

Hey you wanna be cock suckers, you fantasize about sucking a dick for me, don’t you? You think about your little whore mouth wrapped around a thick, juicy shaft. Perhaps you want to go to a glory hole and just suck cocks like crazy, taking load after load, marking you as the little fag boy that you are. I know all of our forced bi conditioning has been doing it’s job. You will suck a dick for me and when you do I want you to be the best cock sucker. I want guys to be aching for your little sissy mouth. I want them to pay you extra for your amazing blow jobs. And then you’re going to bring all that cash back to me.

I’m going to train you on how to worship cock today. So go get a dildo because you’re going to be following along as I worship my dildo with my sexy mouth. You see it’s not just about opening up and shoving a big dick in your mouth. You have to take your time, you have to please every inch of that cock, and for that you need my training. I want you to think of big cock as your God and you are going to worship that dick. Because that’s your job, isn’t it faggot?

And make sure you make eye contact when you’re sucking so he knows you want to be a good little sissy for him. Why is it you want to worship big cock so much? Is it because you’re not packing much down there. When you start to worship big cocks you’ll realize how superior it is to you and you’re going to want to bow down and worship it. So get on your fucking knees as you worship that dildo just as I instruct you.

And as you’re down on your knees looking up at that big cock, I want you to open wide, stick your tongue you, and worship it with your tongue before taking it as far down your sissy throat as you can. I don’t care if you start gagging, shove it down your throat. Watch me faggot. I’ll show you. Now stroke with one hand as you shove that cock down your throat with the other so you begin to associate sexual pleasure with sucking. I’m conditioning you faggot. Make enthusiastic noises as you suck it to show him how much you worship it. Show that cock how hungry you are for it. Your goal is to make that cock cum. This isn’t about your cock as much as you might be stroking it furiously right now. This is about worshiping superior cock.

I’m going to show you so many techniques to make you the best little cock sucker out there. You’re going to love sucking cock with me. Faggots like you need to learn to worship cock. And you’re going to cum so violently from being so turned on by sucking dick. And then you’re going to eat it because you need to know what it tastes like. You need to be trained to love cum. Not only are you going to learn to worship cock, you’re going to become my little cum bucket.
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Ella Kross – Making You Jerk in Drag with Cum Countdown!

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You’re such a loser, I think I’ll dress you in drag and make fun of how ridiculous you look. Get over here and strip naked, dammit! Now put on these panties and this bra, and feel ashamed while I sit here and mock you. I can’t stop laughing at how dumb you look, but I’m not done yet! I’m going to complete your new girly look by putting make-up on you. This is so humiliating for you, but so amusing for me! I crack up as I continue dressing you like the bitch that you are, thoroughly entertained by what an ugly woman you make. Now do a little dance for me before showing me your small cock. Start jerking-off for me while I lay here and watch, giggling at what a desperate idiot you are. Look at you, standing there dressed like a woman and tugging your little dick. Ha! I want you to watch you cum, my new drag queen, but only after I count down from ten. Are you ready to blow your load for me, girl? Ten, nine, eight…
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Mistress Tangent: Turkey Needs Stuffing/Sissy strap-on punishment as Mistresses stuff cocks into his tight ass

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Mistresses Tangent and Toro get him going with some double ended insertion and then Mistress P enters and uses him as well.
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Goddess Alexandra Snow – Sissy Training 101

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Is the sum total of your sissy experience been wearing slutty women’s clothing and jerking off in front of your computer? Seriously? That doesn’t make you a sissy! If you truly aspire to be the best sissy slut you can, you’re going to need my training. We are going to start with the basics– some clothing, body care, and more. You’ll need to pay close attention so you can correctly follow each assignment. Lots of sissy humiliation and objectification!

Categories: Sissy Training
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Goddess Alexandra Snow – I Don’t Want a Man

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I know you wanted to date me, but I don’t want a man. Men are so.. Tiresome and course. And women, well women are almost as bad. They are so emotional and unpredictable. I think I’d rather have a little sissy bitch. That’s what you’re going to be! I have all the clothing already picked out for you. I’m going to dress you and make you into a little doll for my amusement. Say goodbye to your masculinity if you want to be with me.

Categories: Sissy Training
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Humiliation POV Kelle Martina: Be A Sissy Hooker In Public On Halloween

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Kelle Martina

You’re a sissy but you can’t go out dressed like a woman every day. Aren’t you lucky that one day a year, people get to dress up as whatever they want. And everyone thinks it’s just a fun costume. You’ve probably never worn any of your girly clothes outside the house before, right? Well what better opportunity than Halloween. On Halloween you can be anything or anyone, including a hooker, LOL! That’s right, you’re not just going to be a sissy, you’re going to be a sissy hooker.

I want you to get dressed up soooo slutty. I’m talking slutty high heels, stockings, a Short mini skirt, a wig, makeup. You should look like a street walking hooker, lol. I want you to be as trampy as you can get away with publicly. Lots of women like to express their more sexual side on Halloween so you should be able to be just as much of a slut. I want you to make sure you have plenty of time to make yourself look perfect before you walk out that door. I know the thought is exciting you. It’s something you’ve always wanted to do. And it’s totally socially acceptable to do.

And no one will know that deep down inside you really are that slutty sissy. We both know that you are that slutty sissy all of the time but you just can’t show it except for one day of the year. Isn’t it going to be so much fun to dress up and go out in public? I’ll bet you’re so excited to show off your sluttiest outfit and your highest heels! LOL! I want you to impress me, I don’t want you to look like a man in a dress, I want men to have to do a double take when they look at you! I want men lusting after you, LOL!

This is going to be your sissy debut! Aren’t you excited? Maybe you’ll even get lucky and some drunk guy will think you’re a girl and he’ll let you suck his cock, LOL! Or maybe he’ll know and he just won’t care because you look so fucking slutty and hot! You’re going to have so much fun being the sluttiest sissy hooker on the street.
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Humiliation POV Princess Kelly Sunshine: Risky Sissy Fag Chastity Blackmail

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Princess Kelly Sunshine

Sometimes you boys make the dumbest decisions. But that’s ok because I have a lot more fun when you do. You get so horny and stupid and when you do, you beg me to blackmail you. So I’m going to get you dressed up really slutty, and have you get down on all fours and fuck that slutty ass for me, while you tell me what a total fucking loser you are. And you’re going to do this for me on cam so I can take pictures and videos. And you’re going to look into the webcam and tell the world your full name, your phone number, your address, details about your wife and job, every little thing that could incriminate you and ruin your life. Could you imagine if I leaked this video? You’d be totally fucked.

But yet the thought of that makes you so hard cause you love playing these risky masturbation games. But know that blackmail is not a game with me, I take it seriously. So if you want to partake, you better be prepared loser. So if you want me to keep those pictures and videos to myself, here’s what you’re going to do, I’m going to even give you a choice. You can lock that dick up in chastity for me for as long as I want. But locking you up would be doing you a favor because your horny cock is what got you into this mess in the first place. I mean we both know you think with your dick and that’s why You come to Me, asking me to blackmail you. You asked for this and now you’re getting exactly what you wanted. And when that cock is locked you’re going to feel so weak and desperate you’ll do whatever I want. You are going to feel this intense need to do whatever I say.

And there’s only one way you can get unlocked, you are going to suck cock for me. I know you’re a slut and you want your ass and mouth used like the whore that you are. I’m going to turn you into a cock sucking slut. You see you begged the wrong person for blackmail if you didn’t expect to get truly fucked over in the process, lol! So from now on, if you want to jerk your cock, the only way you’re going to be allowed, is while there’s another man’s cock in your mouth! But as I said, I was going to give you two choices. You don’t have to suck cock, you can just stay locked up! LOL!
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Brat Princess 2: Amadahy and Noe – Little Sissy jane takes a Big Black Cock and Gets Invited for Cocktails (1080 HD)

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Little sissy jane does not want to have to take a big black cock. But she will anyway because whores don’t get a choice. Noe trains jane with taking a cock in her mouth from the front, while Amadahy enters her from behind. Little jane complains that is hurts because Amadahy is too big for her. Amadahy ravages the tight little whore anyway. Noe holds jane down while Amadahy fucks. Jane gets very disheveled and her pretty makeup starts to run. Amadahy reminds jane that she is just a condom and a cum dumpster. The Princesses make jane repeat, “i’m just a bimbo,’ over and over until Amadahy empties inside her. Pretty jane looks a mess. Amadahy and Noe send her away to bring them drinks. Jane is invited to share a drink with Noe and Amadahy, but she doesn’t seem to enjoy her drink much.
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Humiliatrix – Miss Kendra Instructs You How to Cum Like a Naughty Sissy Slut

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“You’re not a man, so why should I let you cum like a man? I’m going to train you to cum like a dirty sissy slut, using just your fukkyhole and a cock-shaped vibrator. No more touching your useless boy parts. If you want to cum for me you’re going to moan, squeal and fill your holes like the cock-lusting slut you are…”

Miss Kendra James, sissy training, vibrator instructional, sissyslut cum commands…
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Brat Princess 2: Cali and Kenzie – Sissy Trained to Take Cock with Machine Fucking (1080 HD)

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Brat Princess 2: Cali and Kenzie - Sissy Trained to Take Cock with Machine Fucking (1080 HD)

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. Cali thinks its great! To impress her friend and show off what a slut her locked up sissy has become, Kenzie turns up the speed on the fucking machine. The sissy complains that the adjustment hurts, but the Princesses just laugh. Its chastity rocks and bobs between its legs as it gets pounded by the machine. Cali shows it some training material from the magazine while it gets fucked. The Princesses gang up and taunt the helpless sissy. They play with and vary the speed of the huge cock violating its tight asshole. Kenzie shoves her hand into the sissys mouth and makes it gag on its own taste. Cali takes the controller and cranks the machine up to maximum speed. She finds a blonde wig and puts it on the sissys head. Cali makes the sissy kiss her shoes while wearing the blonde wig and getting fucked. Kenzie leaves to get ready for her nail appointment and asks Cali to supervise the sissy for her. Once Kenzie leaves the room Cali cranks the machine way up. The sissy starts to cry out and make a fuss, but Cali tells it very firmly to shut the fuck up.
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Humiliation POV Miss Tiffany: Humiliating Sissy Tattoo Blackmail Contract

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Humiliation POV Miss Tiffany: Humiliating Sissy Tattoo Blackmail Contract

Miss Tiffany

You dont need to worry because youre going to get a tattoo where no woman is going to see it, right above your little tiny dick. Honestly youre the only one that looks at it, so you dont have to be that embarrassed about your tattoo. But I have such big plans for the little penis of yours. You are going to get the girliest tattoo right above it. I want it to be bright pink or red with lots of sparkles, maybe a bow, or a heart, something that just screams, Im a sissy. LOL! And you should have something written as well, maybe my name, or HumiliationPOV, or baby dick, or sissy, or hand humper LOL! Anything really fucking humiliating. And you know what? You have to do this. Because not only did you sign a blackmail contract but you gave me all of your information. And I will completely fucking expose you for the sissy loser that you are if you dont go through with this.

Maybe Ill even go with you and give the design to the tattoo artist myself so you cant see what it is until its tattooed on you! Theres nothing manly about that tiny little dick of yours and now we need to permanently mark it and make it look even girlier than it already does. Were going to take your disgusting little penis and make it cute. You are going to have the prettiest little baby dick ever! Maybe you could even get your whole tiny dick tattooed in the color pink!

But really no need to be nervous or worry because one; you dont have a choice, and two when was the last time anyone even looked down there? You are a sissy and need to be permanently marked, branded. And then youre going to take pictures and post them on the forum or on Twitter for everyone to see. Cmon you losers have been Begging for this clip. It has so many views. I know you want to and now thanks to me and my blackmail contract, you have no choice. After this you will Never feel like a man again. And thats perfect because youre not a man, youre a sissy bitch who needs a sissy girly tattoo! And think about how hard youre going to jerkoff and cum when you look down and see that tattoo. You will never look at your cock the same ever again. Are you excited? I cant wait to see who does it first. And if you want to make sure you dont back out, be sure and email me for your blackmail contract.
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Mistress – T: Turning Hubby Into A Sissy (Part 1-2)

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I manipulate my devoted husband into dressing up in women’s clothing to amuse me…I tell him that it will turn me on because I’ve started to like women & I’ve been having a lesbian affair…but then I drop the bomb: that I’ll be pimping him out…

…after convincing my husband to cross dress for me I get out my strap-on & start training him to be a sissy slut. I’ll be pimping him out so he needs to learn to suck cock & take it in the ass like a champ.

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Humiliation POV Macey Jade: Cock Sucking Sissy Cuck Hubby

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Humiliation POV Macey Jade: Cock Sucking Sissy Cuck Hubby

Macey Jade

This is part two, click here for part one!

Oh honey, it pleases me so much to see you with your little cock out. I know you heard me making plans with my stud and I can see it got you hard. You sure do love knowing that your wife is going to be pleased by a real man with a big cock. It turns you on so much because you know its what I deserve and you know this is what you deserve. Im sure you loved sucking on the big dildo I got you while you jerked your little cock. You want to be a good cocksucker for big cocks just like I am, dont you?

I hope that youve been practicing and that you can work that ginormous cock all the way down your throat. You love big black cock, dont you? I know you do and so do I. And tonight I have another gift for you to enjoy while Im out with my stud. Youll be sucking that replica of my real mans cock while Im out sucking on it for real.

And its only fitting that while you are sucking cock that you are dressed properly in slutty pink lingerie. Isnt that right sissy cuck hubby? So I got you some hot lingerie and some anal beads for your ass while you suck that dildo. I want you to start training your ass so that one day you can take that big black cock up your ass. Youre going to have so much fun while Im out.

Youre going to be the perfect cock sucking sissy cuck hubby. You want that, dont you? So put on that lingerie, I want you feeling so slutty. Dont you feel so sexy? Tuck your little dick inside of those panties where it belongs. Im going to turn you into the perfect sissy for sucking big black cock.
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Humiliation POV Princess London Lix: Tell Me You’re ‘Straight’ With That Cock In Your Mouth

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Princess London Lix

Today I’ve got some hot jerkoff instructions for you closet fags. Im going to help you come out of the closet by getting you nice and weak by turning that brain to mush as you edge away at your cock for me.

So loser youre going to need a nice big dildo, and its going to go in your mouth, and youre going to be sucking it exactly as I teach you. And at the same time, Im going to tell you how to touch your pathetic cock. So pick up that cock and start running your tongue up and down it and as you do that I want you running your finger tips up and down your shaft. Make both cocks feel good. Good boy, theres nothing forced about this is there loser? Look at yourself, youre doing this willingly and you fucking love it. Feel how hard your cock is as you stroke it and lick that cock.

Now I want you to start making circles around the head of that cock with your tongue and use your hands to make circles around your cock simultaneously. Rub your little faggot tongue all over the head of that cock. Show me how much you love cock. Look how hot I am sucking on this cock as I instruct you. And you know what the fucked up part is? Most guys would be so turned on watching me suck this dildo, but youre picturing yourself on your knees sucking a big cock for me, arent you, faggot?

The thought of sucking dick turns you on so much, doesnt it you little fag? Too bad its not a real cock, I know you also fantasize about taking big loads on your mouth and on your face. You know youre not straight, right? I mean you cant call yourself straight with a dick in your mouth now can you? You are a little closet homo. I know your cock is throbbing right now with all my dirty talk about huge veiny cocks.

Now I want you to grab your cock and start pumping away and at the same time I want you to start thrusting that cock in and out of your mouth. Take it deep, choke on that dick, faggot. You wanna be a little sissy closet whore for me, dont you? You are such a little slut for cock, you ache for it. Now with that cock down your throat, I want you to look at me and tell me youre straight. LOL! Do you have any idea how stupid and pathetic you look right now? Youre a worthless cock sucking little whore and that thought makes you want to cum. Youre sucking that cock like your orgasm depends on it. And as you cum, I want you to finally admit the truth, youre a cock sucking faggot.
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Humiliation POV Goddess Isabel: You Want To Be Perfect And Girly, Just Like Me

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Goddess Isabel

While this clip is not a traditional mesmerize clip, it has hyp n0 t!c undertones, it is set to trance like music, and is constructed to brainwash you.

I want to show you how weak and pathetic you are. You have a lot of secrets but this one is a special secret. Im so perfect, and I look like a woman, because I am. You look like a man, but inside you are a girl. You love shiny leggings, nail polish, lipstick, panties, and all of this girly stuff. Dont think. Im here to turn you into my perfect girlfriend. Yes because I want a girlfriend and you can be my perfect girlfriend. Dont you want that too? Of course you do. You will love it.

Look at how perfect and girly I am, you want to be perfect and girly too. You want to be me. Look at my nails, look at my high heels, you want to look like this. I am your Goddess and you love to be like me. I know exactly what you need. I will transform you. From your skin, to your clothes, to your makeup, I will give you a complete makeover and make you so girly, just like me.

Look at how sexy and girly I am as I mindfuck you with my words. Its so easy to brainwash you into my perfect sissy girlfriend. You just look at me and listen to my words and it all comes so easily for you now. Youre going to look so sexy, so amazing and you will love how you feel once youve been transformed. I cant wait to see how sexy you look.

Do you see my high heels? You should also be in very slutty high heels. It will make you feel so sexy and so girly, just like me. Im destroying the man inside of you, leaving you as a desperate sissy slut, only capable of bimbo girly thoughts and dress. You will be my perfect girlfriend. I cant wait to see how you turn out. I know this is your dream and I cant wait for you to realize your dreams and reach your full potential. Worship and obey, worship and obey.
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Humiliation POV Goddess Kyaa: A Sissy’s Painful Spanking

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Goddess Kyaa

I’m going to take my slave out with me tonight but first, I’m going to spank him. Why? To remind him that he is my little pet, my slave, my play thing, my fucking toy, that I can spank and beat whenever I want. I’m going to paddle the fuck out of him while he thanks me. His ass is already red and tender from yesterday’s beating. But I don’t care, and he likes it. He needs this treatment. Each slap of my paddle stings his little ass but he needs this. It’s going to fucking hurt and he’s going to take every fucking slap.

You’ll hear his groans, his whimpers, his cries which I ignore. I want to make sure his ass is stinging later. I want it to hurt. I want him to suffer for me. I’ve got a few different paddles I’m going to use on his ass. He’s even going to get some bare handed spanking. Isn’t he lucky? He needs his spankings every fucking day, it helps him remember his place. Awwww he’s starting to cry.

My paddling and spanking intensifies and so do his cries and screams. But no matter, I don’t care, his ass is going to get spanked until it’s red and raw, until he can feel it all night long. Look at him, with his panties pulled down, his dress pulled up, and his red little ass! Don’t you wish you were him? Then I humiliate him by making him look at the camera and say, “I just got spanked by Goddess Kyaa.” And of course, he thanks me again. Now his ass looks just the way a sissy’s ass should!
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Humiliation POV Kelle Martina: Sissy Gangbang Cum Dump Bimbo Slut

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Kelle Martina

You are such a little sissy arent you? Of course you are, if you werent such a sissy you wouldnt be jerking your cock off to this video right now would you? But the problem is, you are jerking to it. But youre too much of a bitch to give in to these desires of yours to be turned into a little whore, so Im going to make sure you become the sissy slut you truly dream of being. You see because you dont just want to just dress up, you want to suck and fuck huge cocks, lots of them at the same time. You want to be a sissy gangbang whore. That is what you what isnt it? Its what you fantasize about.

So Im going to dress you up in a slutty little outfit. Im going to turn you into the hot little bimbo youve always wanted to be, whether you like it or not. Men are going to find you irresistible. You see Ive told some men about you, about what a fag you are and how much you want to suck cock and well, they cant wait to meet you. Theyre going to make your fantasy a reality. Im going to arrange a gangbang party for my little sissy bitch. Youre going to be the center of everyones attention, lol.

Imagine how youre going to feel when I parade you in to a room full of men and show you off in your slutty little outfit for the first time. Youll be nervous, scared but so excited. Especially once you see all of their huge cocks. We both know what this is what you really want. So I want you to just let go, and become the sissy whore gangbang fag of your fantasies. Just give in to it. Youre going to be so vulnerable to whoever wants to fuck you in the ass or the mouth. Youre going to be a little cum dump. Im going to make sure of it.

Theyre going to humiliate, fuck and jizz all over my sissy bitch. Imagine all those huge cocks going in and out of all your holes. And Im going to look at you right in the eyes and laugh in your face. Theyre going to treat you like a little fuck doll because thats exactly what you are. Im going to fuck your world up, and youre going to love it. And while theyre pounding you and dumping loads on you, theyre going to be calling you names. I can see how hard your little sissy clitty is your panties right now just thinking about all of this. Youre going to be a cum covered sissy slut. LOL! Youre a total sissy cum dump, thats exactly what you are. You dont get to cum until youre covered in jizz. And youll say, Thank you Mistress for turning me into the sissy cum dump Ive always wanted to be.
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Princess Ellie Idol: GIVE IN TO THE GAY 720P

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You spend an awful lot of time trying to convince people you aren’t a faggot. You want others to believe you think cock is gross. You want them to believe the only thing for you is a woman. You’re hiding something. You’ve been supressing your true feelings for some time now. Truly straight men watch lesbian porn or go out and fuck girls! You like to see porn with dicks in it. Why? Because you secretly desire cock! Watching all my humiliation clips, maybe dressing up as a sissy….you’ve taken a step today in the right direction. You bought my forced bi clip because in all reality, you’re a little curious. I, along with these well hung studs will help you discover your true identity. You’re going to give in today… Give in to the gay!
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Humiliation POV Kelle Martina: Sissy Jerkbot Brainwashing (Effects)

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Kelle Martina

You crave to be a jerking sissy zombie. Im going to manipulate and mold your mind as I guide you, allowing you to sink into hyp n0 t!c trance. Im going to transform you into the little sissy cock sucking bimbo youve always wanted to be. With my guidance you will begin to see yourself as a sexy bimbo. Now wrap one hand around your sissy clitty, the rest of you will remain completely frozen in place as your hand starts to move up and down, up and down. Slowly becoming a little sissy jerkbot. Jerk, eyes wide open, mouth gaping, ready to accept a cock at any time and you are a jerkbot. You cannot stop jerking while the rest of you lies there frozen as I begin the sissy bimbo transformation process in your mind.

Picture yourself, feel yourself turning into that sexy sissy bimbo that youve always dreamed of becoming. Let go of all of your inhibitions as you continue to transform as you continue to stroke like a good little sissy jerkbot. You are a sissy, you are a bimbo. You love cock. You love feeling girly, sexy and slutty. Feeling slutty turns you on so much. I am your creator and you are my sissy bimbo jerkbot. Jerk, jerk, jerk, unable to stop.

Now repeat after me, I am a sissy jerkbot. I love cock. I am a bimbo. I love to be your jerkbot. And thats all you are, a mindless stroking zombie being brainwshed into a sissy bimbo jerkbot. Jerk, jerk, jerk Good little sissy jerkbot. Stroke as you think of cock after cock filling your mouth, your ass, becoming a sissy fuckdoll. You are completely blank, your mind is completely blank as I tell you exactly what you are. A sissy jerkbot. Repeat it over and over as you jerk.

Doesnt it feel so good to be an obedient little sissy jerkbot for me? I have complete control over your mind, youre helpless, I have you exactly where I want you. You are a sissy bimbo jerkbot who loves cock. You exist simply to be my sissy jerkbot.
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