Tag Archives: Sissy Training

Subbyhubby: Cuckolding The Perverted Stepfather MiniMovie

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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 slaps her new bitch in the face again and again, then puts him in a scissor just to hurt him. But what Cameron really wants to do is have fun with his perversions. Little does stepdad know that Cameron is actually a Dominatrix and that her “boyfriend” is actually a sissy bitch in training, and now stepdad will be too! Cameron puts her stepdad to work cleaning her ass with his tongue while the lowly sissy boyfriend has to worship her feet. Cameron then puts the bitches to work cleaning the house until she gets back from partying. Unable to find the stud cock she wanted, Cameron decides to fuck her stepdad instead – all while making her “boyfriend” watch and clean up after them. Cameron just laughs as her sissy bitch boyfriend has to clean up the huge cum load off her pussy and the stepdad’s cock. Since he seems so revolted by cleaning the stepdad’s cock, Cameron orders her sissy boyfriend to make love to it with his tongue, sucking the cock and licking the balls until stepdad blows another load of cum, this time all over the boyfriend’s face! Cameron realizes the boyfriend needs more sissy training, so it is back to walking in heels and learning to show off his body like a proper sissy slut. Cameron plans on whoring both of these bitches out and wants to make sure they can really take cock in their ass, so she orders both of them to fuck themselves in the ass with a dildo while she watches, masturbating to their humiliation. But these bitches can’t even fuck themselves right, so Cameron has to take over and fuck each of them herself. She truly enjoys turning the men in her life into pathetic little bitches. Now she won’t have to worry about her stepdad perving out on her anymore. Cameron has her stepfather and her boyfriend both kneel before her, naked and in chastity, so she can gloat about her power over them. Cameron orders her stepdad to lick her ass while her boyfriend worships her feet. As her slaves do her bidding, Cameron humiliates and degrades them both, laughing at how pathetic they are. She leaves them to do her housework while she goes off to find a real man to fuck. Cameron returns from partying and is upset to see that her stepfather has performed his housework duties poorly. She wonders why her mother even keeps him around; maybe he is a good fuck? Cameron decides to find out for herself, telling her stepdad to fuck her – and her boyfriend to lick his feet! The cuck boyfriend is disgusted, but obeys Cameron’s orders. Cameron really gets into fucking her stepdad, making him perform from several different positions, all while making her bitch of a boyfriend first clean their feet, then lick his cock and balls and her pussy while they fuck. After her stepdad blows a huge load all over her pussy, Cameron orders her cuck boyfriend to lick the cum off of the stepdad’s dick, then off of her pussy. Cameron asks her cuck bitch boyfriend if he would like to taste her pussy; of course he says yes. But Cameron has a surprise for him; he has to taste it off of her stepfather’s dick! She just loves humiliating the bitch, ramming his face down on the cock again and again. Cameron grabs her bitch of a stepfather and orders him to blow a big load all over her boyfriend’s face. Cameron laughs hysterically at all the cum on his face, then orders him to eat it just for her amusement. Cameron tells her boyfriend that, since she has trained him to suck cock, he is now nothing but a sissy bitch and needs to learn how to look and act like one. Cameron applies some makeup to her sissy, then orders him to show her how sexy he can walk. After a few tries, he does it to her satisfaction, then has to demonstrate his humping skills. Cameron just laughs at what a bitch she has turned her boyfriend into. Cameron plans to whore both of her bitches out and wants to make sure they can take cock properly so she orders them to fuck themselves in their own asses with a dildo while she supervises. As her bitches shove dildos in and out of their asses, Cameron masturbates her pussy, excited to see what levels of humiliation her men are willing to take for her. Cameron decides that the bitches are not fucking themselves well enough so she decides to take over, bending her bitches over and ramming the dildos up their asses. But their training is not over, as Cameron orders each of them to clean up their ass juices off their dildos – after all, a whore should never leave a customer’s cock dirty.
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Humiliation POV Princess Kendi Olsen:With Every Load You Swallow, My Bank Account Will Grow

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Princess Kendi Olsen

I’m tired of hearing that you can’t afford to serve me. THat’s fucking stupid. I know you work hard for me, you’ve cut back on spending for me, and you’ve even stopped dating. You’ve really worked hard to make more money but it’s still not enough to serve me. And I know that’s all you want. You need to serve me. So since what you’re making isn’t cutting it and it’s taking too much time and effort, I’ve come up with a solution, a way you can serve me without working as much yet still making more money.

I’m going to turn you into my hooker cum dumpster slut. Now you can actually have a sex life instead of jerking all day like a loser. Not only are you going to have a sex life, but you’re going to have a high paying sex life. You can put ads up on craigslist as my loser cum dumpster and you can give blow jobs for twenty dollars. And since it’s so cheap you’ll have so many guys. Then you can come to me on your hands and knees like the sissy bitch that you are and offer me all the money. I will make you tell me about all the cocks you sucked to get it, LOL!

And it doesn’t have to stop there. You can be an anal whore for me and make even more money. You can even make videos of you humiliating yourself or fucking and sucking other guys as a sissy cum whore and sell them online. Tons of faggots will eat them up and the proceeds can go to me. You’ll be a real life And an internet whore. You just wanna make more money for me. You’re going to be slurping down so much cum for me. I know you want to be a faggot just for me. You want to make me happy.

Being a sissy faggot and making money for me will make you so fucking horny. And since this will take up less of your time than working all the time, you’ll have more time for me. So you can be a little cock slut for me, can’t you? You want to be my cum guzzling whore. You want to make me so very happy. This will be so exciting. I’m going to get rich off of you as you choke on cock, as you get gang banged like the sissy whore that you are. You’re my gay for pay faggot. You can drink cum to make me richer. With every load you swallow my bank account will grow.
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Cruelgf: Apply To Be Our Dreamhouse Sissy Maid

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We’re recruiting sissy maids to keep the CruelGirlfriend Dreamhouse clean and tidy at all times. I’m gonna take you on a tour of the whole dreamhouse – where the girls live and hang out with their real men and what we expect from our feminized missy-maids. We’ll start in the hall where we leave our dirty heels and sweaty sneakers for cleaning. Sissy maids will be expected to keep our shoes totally IMMACULATE! I’ll show you the little sissy-prison you’ll be allowed to sleep and prepare yourself in and the rooms the girls bedrooms that you’ll be expected to keep tidy. We’re all pretty lazy when it comes to cleaning up after ourselves which is why pansy sissies like you have an actual purpose in life. You’ll pick our panties and clothes off the floor for washing, and go around clearing up used condoms and sex-toys after we’ve had our boyfriends over. I’ll show you the kitchen where you’ll spend much of your day washing up, preparing our meals, fetching drinks for us and doing the laundry and chores and then I’ll take you out into the Dreamhouse gardens. This is where all your sissy-maid training will be put to the test when we have our famous CruelGirlfriend garden parties. You’ll be made to wait on all of our guests and provide a whole lot of entertainment for everyone! Finally, I’ll take you down to where you’ll end up if you fail to complete your duties to our satisfaction – the stables. This is where sissies are punished for their laziness. All applicants for the position of Dreamhouse sissy-maid will need to reply to the email address at the end of the video.
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Goddess Alexandra Snow – Feminine Fancy Trance

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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 it to yourself to delve deep within..
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Sissy Smoking Conversion 4 (Hypnosis Mindfuck)

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My fourth installment in seizure-inducing smoking sissy mind-fuckery. Hope you enjoy!
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Humiliation POV Goddess Sahrye: Sissy Damsel In Distress Self Bondage

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Goddess Sahrye

So I hear that I’m the bondage queen of your dreams. That’s right, in case you didn’t know, I’ve done many bondage scenes. With real men of course. But you don’t want to see me in bondage, you want to be just like me, don’t you? You want to be a bondage princess. So I’m going to teach you all of the self bondage techniques that I know. Do you have all of the items you need to be a damsel in distress? LOL! Do you have your high heels and your pantyhose? Do you have your gags? All the fundamentals of a bondage girl. Because you know boys don’t get tied up in bondage, only girls. And that’s what you are, isn’t that right?

So in order to play the role, you have to look the part. Rule number one of a bondage queen is that her heels never ever come off. So I’m going to teach you how to lock your heels on. Good girl. Next I’m going to teach you how to tie up your legs, we have to make sure you can’t run away. Doesn’t that feel good? You love the sensation of being bound. You’re a pretty girl with your legs all taped up. But you’re not a real damsel if your hands are free. So I’m going to show you how to put your handcuffs on and make sure your arms are secured tightly behind your back.

Doesn’t it feel good to be my little bondage princess. Now that your hands are behind your back and your legs are nice and secure and your heels aren’t going anywhere in your tight little mini skirt with those pink panties peeking through, I want to see you struggle.

You know what comes next don’t you? Take those cuffed hands behind your back (I’ll show you how), grab a pair of panties and shove them in your mouth. Gag yourself sissy. Good girl. Now I don’t want you to spit that out so we’re going to make sure it’s nice and secure with a ball gag. How do those panties taste? Well aren’t you the perfect damsel princess? Look at you, you’re a faggot little sissy loser who’s trying to impress me by being in bondage for me, the internet’s most popular bondage queen. You must feel so pathetic. You’re my bitch. I’m going to leave you here just like this, gagged and bound. Struggling and drooling in your high heels and your pantyhose and your sissy girl clothes. I’ll bet you’d love it if I took pictures and posted it all over my social media accounts.
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Humiliation POV Queen Sahara: Every Man You Suck And Fuck Will Know That You’re My Sissy Bitch

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Queen Sahara

You love being my little sissy bitch, you love wearing panties for me, makeup, bras, and wigs for me. You would do anything I say. When it comes to your sexuality, I control your clit, I own it. And if I want you to be my prissy sissy, then that’s how things are going to be. And you love it so much because it turns you on so much. It makes you so hard to feel like a woman. You get so turned on just from putting on a pair of panties.

I know you already have a large collection of lingerie and it continues to grow. Soon you’ll have more sissy clothes than man clothes as you become more and more girly. You get so hard when you act like a sissy girl for me. And I want to take things to the extreme, I want to put an ad up on craigslist and have you get gangbanged like the slut that you are. I want your mouth and ass constantly filled with cocks until you’re a brainless fuck toy. And that’s what you want to, I know it is.

I want you to be another man’s bitch. And I want you to do it for me. You’re going to be such a good cocksucker, just for me. Every man you suck and fuck will know that you’re my sissy bitch. You’ll know that you’re my sissy bitch. I’m going to help you dress up so that you’re the sluttiest sissy that there is. And you’re going to love it. You’re so hard right now thinking about being my little bitch and that gives me so much control over you. You wanna be my bitch.

Are you ready for the sissy lifestyle? Are you truly ready to embrace it? Once you do there’s no turning back. There’s nothing you can do. Even if you could stop it you wouldn’t want to. This is your life. You’re my little girl and you love that so fucking much. I’m going to keep that little clit dick locked up in your panties because that’s where it belongs.

From now on you will be my little bitch. This is the lifestyle that you want. And this is going to make us so close, and you want that so badly. I’m going to teach you so much sissy and you’re going to thank me! Deep down inside you feel feminine and I’m going to make sure you feel so girly because you’re not a man.
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Divine Goddess Jessica: Faggy’s First Fuck

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I finally talked my little slut, faggy, into taking on a real live cock! She found some old horny dude on craigslist, dressed up in some skanky outfit and sucked him off in a motel room. Watch my reaction video and see what it’s like to be critiqued on your dick sucking skills. Watch me laugh at her when she squirms away and wimps out of taking a cock in the ass.
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Subbyhubby: My Stepbrother is a Sissy Bitch (FULL MOVIE) (July 11th 2017)

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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 in her clothes. Vanessa catches him in the act and tells him she has him recorded in her clothes. Unless he wants his father to find out about his panty fetish, he had better start doing everything she says. Shamed by the prospect of his dad finding out his secret, he quickly agrees. After busting her step-brother Cody wearing her clothes, Vanessa teases him by showing off her beautiful pussy. She laughs as she tells him that she knows how much he wishes he had a vagina rather than his small useless penis, but that is why his place is worshiping a real woman. Vanessa sits back and enjoys an orgasm as her stepbrother humbly worships her pussy, terrified that Vanessa will tell his father his shameful secret. Having already introduced her step-brother Cody to the taste of her vagina, Vanessa now orders him to taste her ass. Vanessa enjoys herself as Cody’s tongue licks and cleans her asshole all under the threat that she will tell her stepfather what a pervert Cody is. Cody’s punishment has just started, Vanessa has invited his best friend, James over to see his humiliation. She tells James that Cody wants to be a girl so she is going to show him how to be one, starting with sucking James’s dick! Of course Cody does not do it correctly so Vanessa shows him how to properly suck a cock and make it cum. When James shoots his load in her mouth, Vanessa spits it into Cody’s mouth, then makes him gargle his best friend’s cum – how humiliating! Vanessa decides to show Cody how a real woman fucks a man. While she is fucking James, she while orders Cody to lick James’s dick and balls like a woman would. Vanessa then has Cody worship her feet while the fucking continues. When James is ready to cum, he pulls out and shoots his load all over Vanessa’s belly. Cody has to lick up James’s cum yet again while Vanessa laughs at what a bitch her “macho” stepbrother really is. While Vanessa and James cuddle after intercourse, then Cody worships their feet as an obedient cuckold as they make fun of him. Then Vanessa decides to give Cody a “reward” for being such a good stepbrother, letting him jerk off on the panties he was wearing. Once Cody shoots his load on the panties, Vanessa orders him to put the cum soaked panties on while she and James laugh at what a pathetic bitch he has become. Cody may have ignored his dad and mistreated Vanessa, but she has more than paid him back for acting like such a jerk
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Divine Goddess Jessica: Faggy’s First Fuck

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I finally talked my little slut, faggy, into taking on a real live cock! She found some old horny dude on craigslist, dressed up in some skanky outfit and sucked him off in a motel room. Watch my reaction video and see what it’s like to be critiqued on your dick sucking skills. Watch me laugh at her when she squirms away and wimps out of taking a cock in the ass.
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Humiliation POV Princess Lacey:Your Boyfriend Is A Sissy Faggot, Lock Him Up And Cuckold Him

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Princess Lacey

This clip is meant to be viewed by you and your girlfriend, buy it for her!

I know your kind, you’re a sick, perverted, faggot sissy bitch, just dying to be locked up in chastity and fucked in the ass. But you’ve somehow managed to convince some poor girl to be your girlfriend. And that’s exciting for me because I’m about to have a lot of fun with that. And the whole dynamic of your relationship is about to change forever. I want you to press pause right now and go and get your girlfriend, she’s going to watch the rest of this clip with you. I’m going to mainly be talking to her, with you on your knees by her side, as she watches this. I’m going to tell her exactly what kind of freak you really are, and exactly what she can do with it. She might take my advice and have a lot of fun with you, or she might just leave your pathetic ass and you’ll be alone with your perversions.

Press play for her now.

So you must be the girlfriend. Is your pathetic boyfriend on his knees next to you? This may come as quite a shock to you, but your boyfriend is a sick, perverted freak. He’s been stealing your panties and wearing them while he jerks off to videos where sexy girls tell little freaks like him exactly what to do, and he obediently listens because he’s just a pathetic loser. And I have some valuable advice for you. You might first be shocked and turned off by this information, and you may want to leave him right now, and I wouldn’t blame you. Look at him right now, and you loser, look at your girlfriend and tell her you’re a fucking freak. I’ll bet he listened, didn’t he?

I think you should turn him into the little faggot sissy that he is. Get yourself a chastity device and lock his pathetic cock up. You won’t be needing it any more and I don’t think you want it any more. From now on you can fuck whoever you want because not only will you be turning him into a sissy, but you’ll be cuckolding him. And he’s going to fucking love it! Aren’t you bitch?

You should start humiliating this loser you call a boyfriend. You can make him wear panties and shove a big dildo up his ass. He’ll like that. And while he’s busy with himself you can go to a bar and pick a real man and bring him home and fuck his brains out while your little loser bitch is locked up in chastity, watching from a closet. Take full advantage of the situation. Don’t be so quick to up and leave him, you could get a lot out of this. You can make him buy you clothes for your dates, he’ll even pay for your dates. He’s nothing but a little sissy faggot.

Oh and another thing, he doesn’t want sex any more, he’s not turned on by you. He likes cock, lol! I’m sure you’re not even that turned on by him, I mean look at him. So what you should do is get a strap on and fuck that little faggot’s ass. I have so many things I’m going to explain to you in this clip. You’re really going to thank me. He’s not your boyfriend anymore, he’s your cuckold sissy faggot bitch to do whatever you want with. So have fun with him or leave him, either way, now you know the truth.
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Mistress – T – Fetish Fuckery: Big Kinky Ass Fuck

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Watch this bound sissy slut take my big black cock.
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Humiliation POV Kelle Martina: Sissy Jerkbot Brainwashing

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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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Humiliation POV Princess Lacey:You Can Only Listen To Sissy Cocksucker Music From Now On

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Princess Lacey

The following is a member submitted clip idea. We make your ideas for free on HumiliationPOV. Princess Lacey has done this one to perfection! She will make you feel like such a cock sucking sissy! You’ll be bobbing your head to the beat like the cocksucking sissy that you are! The description is the member’s clip submission in his own words.

I once heard a girl say that Christina Aguilera makes the best cocksucker music. So I asked her what cocksucker music was? She explained that it’s what she calls any music that appeals predominantly to women and gay men, i.e. people who are likely to suck cock. I realized that this applies to pretty much all the music I listen to as a sissy.

So it occurred to me that this might make a good idea for a video, where the Brat in the video tells the viewer that they are only allowed to listen to cocksucker music from now on. She tells them that they must go through all of their music and ask themselves if someone who heard them listening to this would assume that they sucked cock. If the answer is yes, they can keep that song/album, but if the answer is no, they must get rid of it, throw out the CD if physical or delete if digital. They must also apply this same litmus test before buying or streaming any new music from now on. If it would make people think they’re a cocksucker, they can buy it. Otherwise they can’t.

The Brat in the video could give examples of songs or artists that would qualify as ‘cocksucker music’, such as female pop singers, boy bands, etc.

Get ready to enjoy your new music library, the only music will ever listen to from now on.
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Subbyhubby: Poker Face – 3 Chicks 1 Cuck – Mini Movie

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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 to his house that he quickly agrees to everything they ask – especially when they start flashing their tits, asses, and pussies at him! He agrees to get naked for them, causing them to burst out in laughter at how small his dick is, especially when compared to a real cock! Because his cock is so small, they let Eugene know that the only way he can be around them is to have his sissy dick locked in a cage – while he is dressed like a sissy as well. Of course, the pathetic geek is all too eager to agree to anything for these hot girls. So happy to be around hot girls, Eugene quickly agrees to be dressed in a sissy maid’s outfit and locked in chastity, cleaning house as the girls play poker and drink. The girls have an interesting twist on playing poker; as Eugene soon finds out. After getting the strapon locked on his head, Eugene is told to face fuck the pussy of the winner of the hand. If that girl actually show in any way that she enjoys it, she has to drink! How pathetic it makes Eugene feel, that the girls don’t even want to admit accepting pleasure from a dildo he is wearing on his face! The girls decide to play another game with Eugene: having him smell and lick their dirty asses clean, then guess which girl’s ass he was licking! The girls laugh as they order Eugene to breath in their ass odor, then rub their asses all over his face. Of course, the nerd guesses wrong several times before finally identifying the correct girl. Eugene is all excited, wondering what his prize is for finally winning the game. Knowing what they have planned next for him, the girls just burst out in laughter. The girls decide to order some pizza, ordering Eugene to answer the door in his sissy maids outfit. The girls tell the pizza man they have no money for a tip, but would he like a blowjob instead? He quickly agrees, but then gets told it will be Eugene giving it! Eugene does not want to do it, but the girls tell him it is the only way they will let him out of chastity, so he reluctantly agrees. The girls just laugh as Eugene sucks the pizza man’s cock, giving him directions and even forcing his mouth wider to get more of the cock in. When the pizza man blows a huge load all over Eugene’s face, they laugh at his humiliation, then order him to clean up so that they can use him some more. They leave him alone and sobbing, cum dripping down his face.
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Humiliatrix – Mistress Kendra Convinces Your Woman to Cuckold Humiliate You

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“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…”
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Humiliatrix – Bimbo Busting: Princess Luna Makes You Jizz Your Own Face

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“You better strip before I smack you, because your fukky holes belongs to me tonite, bimbo boy. I’m gonna peg you with a plug, pinch your tits and fuck you up with my strap-on until you are nothing but a cum-lusting jizz-slut, ready to open those bimbo lips and swallow your own spunk at my command…”
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Brat Princess 2: Amadahy and Jade – Sissy Whore Gets Out of Chastity (720 HD)

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720 HD: Its time for Jades sissy to be milked. Amadahy is invited to share the sissy-girl. The sissy follows the Princesses into the living room from where she is kept. Her frills are lifted to expose her chastity. Her clit is swollen and her balls are full. Both Princesses tease the sissys chastity. She moans as her Princesses tickle between her legs. Jade rubs her clit against her sissys. Jade and Amadahy decide that the sissy will be milked into her own mouth. They remove her chastity. She grew so big in there! Jade feeds the sissy its pre-cum. It licks the pre-cum off Jades fingers. The sissy-girl is so excited, it almost cums right away. Jade gets upset with her sissy. The easer slut has nearly embarrassed her in front of her friend with a premature orgasm. She is not allowed to cum yet. Jade eventually gives the slut permission to cum, but only under the condition that she be flipped over and jerked into her own mouth. The Princesses position the sissy with her lady stick over her mouth. The sissy cums on her pretty face and in her mouth. Jade instructs the sissy to say, I love being a cum-whore. Jade pushes all the cum into the whores mouth and down her throat. Now get the fuck outta my face and clean the kitchen, Jade says. She specifies that she wants the sissy to put her chastity back on, first. Then, clean the kitchen with the cum still on her face.
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Meggerz – Pay To Obey Humiliation: Sissy vs. Me

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We’re going to compare you, the the fat, hairy sissy “Gwen” with a real curvy woman, me. You will be wearing a lacy black bra and a pair of panties like mine for the judging. And then from the very tips of my toes all the way up my body we will compare. How does it make you feel when I grab my real luscious breasts knowing all that fills your bra cups is fat? How does it make you feel knowing you’ll always have an ugly bulge between your legs and not a pretty little pussy? You’re a zero, bitch and I am an 11. You will never wake up to be the girly girl you feel on the inside. You will always be a fat, hairy, old man.
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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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