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Tag: Cruel Girlfriend

Cruel Girlfriend – Mia – Blackmailed Until You’re Gay

Cruel Girlfriend - Mia - Blackmailed Until You're Gay

Are you terrified of the idea of sucking a real cock sissy? You play your little dress up games – wearing your foo-foo sissy uniforms and slutty lingerie – prancing around in your heels and wig pretending to be a girl but you know you’ll never be a 100 percent certified sissy until a real man has put his cock into your mouth and cum down your throat. You know you’re not complete but the fear of being made to take cock prevents you from doing your sissy duty and serving a real man. I am going to help you sissy. I am going to give you no choice but to suck cock. You’re going to send me a before and after picture of you dressing up in all your sissy disgrace. It’s going to be the perfect blackmail material to push you down a road you’d never have the courage to do on your own. I’ll use your humiliating pictures to blackmail you every step of the way. I’ll help you select the right man to take your virginity. I’ll help you arrange the first meeting in a cheap hotel room and I’ll help you pick what to wear for your first time. If you try to back out at any point – I’ll expose you for the sissy you are to everyone. You’ll follow my instructions or I will ruin you. You’ll wait for your first cock in your hotel room all dressed up in your sissy clothes and you’ll let him in and do EXACTLY what he tells you to do. And guess what sissy, the guy with his cock in your mouth is going to send me more photos – so I can blackmail you further and further. Before long you’re going to be sucking so much cock and getting fucked by so many men you’ll be turned gay forever.

Keywords: Female Domination, Free, Femdom POV, Forced Bi, Coerced Bi, Make Me Bi, Enforced Bi, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Humiliation, Degradation, Blackmail, Blackmail Fantasy, Blackmailed, Blackmailing

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8 min

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Cruel Girlfriend – Sissy Rental Maid Services

Cruel Girlfriend - Sissy Rental Maid Services

I don’t care that you don’t want anyone to see you dressed like that! I don’t care that you feel silly and humiliated all dressed up in a frilly maid’s uniform. I don’t care that you’re embarrassed when you’re made to curtsey or when they pinch or slap your bottom. I don’t care about how tiring the work is or that it hurts your poor feet spending all day in those impossibly high heels. I don’t care that your uniform is way too short or tight for you. I don’t care that people laugh at you as you walk to work in such an effeminate girlie outfit. All these little complaints are irrelevant to me – you’re going to continue to work as a maid at the CruelGirlfriend Sissy Maid Rental Services until the end of your contracted term and that’s an end to it! You’re in such high demand – my female clients love how well you scrub their apartments clean – they love how weak and unthreatening you are with your pathetic cock all locked away in chastity. They love how they can boss you around and make you do all the chores they hate, and they love humiliating you and laughing at you as you obediently clean their bathrooms, fold their laundry and neatly make their beds. My male clients love how perfectly feminine you are, how girlie you look as you bend over at the waist to dust their sports trophies. They love that you tremble when they slap your bottom and they love that they can order you to complete even more humiliating services for extra cash. You’re going to be working here for quite some time sissy, so I suggest you be a good little sissy servant and get used to all the little issues you have!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, POV, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Forced Crossdressing, Humiliation, Degradation, Maid Fetish

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673 mb
13 min

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Cruel Girlfriend – Daisy Dillon – Sissy Maid Spanking From Sir

Cruel Girlfriend - Daisy Dillon - Sissy Maid Spanking From Sir

I’ve told my new boyfriend that you, sissy, haven’t been working hard and getting your chores done quickly enough. I was very clear when I demoted you from boyfriend to sissy-maid that if you wanted to stay in my life and live here in your special pink bedroom that you’d need to serve as my 24/7 housemaid. You knew it was going to be humiliating, serving an alpha couple in the house you used to live as my boyfriend. You knew it was going to be hard work keeping the place clean and tidy, running errands for us, cooking and serving our meals and drinks. You also knew that if your performance as our maid fell short of our expectations you would be punished. Would you like to know how my new boyfriend intends on punishing you when he comes home? You’ll continue with your duties as normal. My man will come home and you’ll greet him by taking his coat and serving him a drink. You’ll finish preparing our evening meal and bring it to us like a good little waitress. After our meal you’ll tidy up, wash the dishes and then fetch your collar and leash to present to me in my thrown room. I’m going to fasten the collar and leash to your neck and lead you to where my new boyfriend is waiting where he will administer a thorough spanking. You’re going to bend over his lap while he spanks you long and hard for your lazy behaviour and you will thank him for each blow. I’m not even going to hide my giggles as you pathetically cry ‘Thank you Sir’ after every crack of his palm on your sissy maid ass. Maybe you’ll learn your new status in this household after he’s finished with you sissy!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Daisy Dillon, POV, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Gender Transformation, Humiliation, Degradation, Cuckolding, Cuckold, Cucky, Cuck

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628 mb
12 min

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Cruel Girlfriend – Bella Mendez – CEI Harsh Humiliation

Cruel Girlfriend - Bella Mendez - CEI Harsh Humiliation

There seem to be so many clips featuring hot bratty girls convincing losers like you to eat their own cum. Gently encouraging you and coaxing you along until you blow your loser load into your own face. At Cruel Girlfriend we don’t believe a CEI clip should be a softly-softly affair. We believe losers like you deserve to be harshly humiliated every step of the way until you empty your cumload into your shame-red face with our crushing verbal humiliation still ringing in your ears. That’s exactly what’s going to happen now freak. You’re going to jerk off as I ridicule you and spit insults at you until you fill your own mouth with cum. Losers who watch cum eating instruction clips deserve to be humiliated. Listening to an out-of-your-league girl berate you while you jerk off is pathetic – and you need to feel ashamed of yourself. I’m going to totally make fun of you while you jerk off as you prepare to cover your own face in cum. I’m going to laugh at you as you get yourself into the humiliating loser position with your cock aiming straight into your mouth ready to accept my order to cum. I’ll count you down – making you admit what a retarded loser you are until it’s time to face your embarrassing end game. Open your mouth wide faggot – open wide and swallow your own cum you pathetic fucking cum-eating loser. Expect the most intense verbal beat-down fucktard!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Bella Mendez, POV, Instructions, Masturbation Instruction, Jerk Off Instruction, Jerkoff Commands, JOI, Humiliation, Degradation, CEI, Cum Eating Instruction, Cum Eating, Cum Swallowers, Male Cum Swallowing, Cum Countdown, Verbal Humiliation

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405 mb
7 min

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Cruel Girlfriend – Princess Aurora – Bullied and Humiliated

Cruel Girlfriend - Princess Aurora - Bullied and Humiliated

Bullying you losers into gulping down your own cumloads is only half the fun – Humiliating and mocking you while you jerk your cock into your own face and then laughing at you for actually swallowing it – now that’s fun! Let’s face it – losers like you don’t have many opportunities to make girls like me smile – but you can humiliate yourself for my entertainment. Allow yourself to be totally ridiculed just to amuse me – you’ll do that won’t you. So, when I tell you you’re going to eat your own cum for me – and I explain how I’m going to put you into the most embarrassing position and watch you jerk yourself off into your own face – you’ll do it. I’m MAKING you do it! I’ll bully you into doing it – your weak little mind won’t be able to put up any resistance – just put your legs over your head and point your cock into your face ready to give yourself an emasculating cum shower. But while you pump away at your loser-stick, let’s just spend a few moments contemplating the pathetic predicament you’re in. You are all contorted in front of a hot girl, desperately trying to cum into your own mouth just for my enjoyment. You are pathetic! You are a Loser. You are a humiliation addicted cum junkie! Oh, I’ve only just started on your verbal humiliation loser. By the time you’ve filled your mouth with your own cum and I’m done laughing at you for making you hold it in your mouth – I’m going to make you swallow it down while I tell you just what a weak, cum-slut faggot you really are. Swallow your load while I give you the worst verbal beat-down of your life!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Princess Aurora, POV, Humiliation, Degradation, Instructions, Masturbation Instruction, Jerk Off Instruction, Jerkoff Commands, JOI, CEI, Cum Eating Instruction, Cum Eating, Cum Swallowers, Male Cum Swallowing

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662 mb
12 min

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Cruel Girlfriend – Get Used to Pink Sissy

Cruel Girlfriend - Get Used to Pink Sissy

I’m going to turn your whole fucking life pink sissy! By the time I’m done with you you’ll be so blinded by pink you’ll even be thinking and dreaming in pink! I’ll start with you clothes – all sissies need to wear pink it’s a kinda rule that if you’re gonna dress like a girl you’re going to wear the most feminine colour – pink! So that means pink frilly panties and a matching pink bra. You’ll wear stockings with pretty pink bows and we’ll find you a cute pink skirt and top combo or a short pink dress. I’ll force your pink painted toes into a pair of sky-high pink stripper-heels and make you walk to the bathroom to give you a total PINK makeover! A silky pink wig on your head is gonna look so girly and I’ll give you bubblegum-bimbo pink makeup – glittery eyes and glossy pink lips. You’re going to look adorable! All that pink is going to turn you into such a bimbo-princess! So, what else does every pink sissy need? A cute pink plastic chastity device so secure she’ll never be able to get her sissy-clit free! Sissies stay locked in chastity and I’ve got the perfect little device for you – the anti-pullout VICE cock-cage! Your poor little cock is going inside, and it won’t be coming out ever again. If you ever want to cum – you’ll be doing it the girlie way – with a big PINK dildo in your sissy-hole! Your locked-up cock can leak out a pathetic sissy-gasm as you fill your ass full of big pink cock and fuck yourself like a girl to a humiliating orgasm. Enjoy your new pink life sissy!

Keywords: Female Domination, Free, Femdom POV, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Cruel Girlfriend, Humiliation, Degradation

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240 mb
10 min

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Seduced And Sextorted

Seduced And Sextorted

So, did you get the panties I wanted you to buy for me baby? Can you show me? Hold them up to the webcam so I can see them. Aw yeah they’re so pretty – I love them so much. Y’know what I’d find so hot? It would be so naughty if you put them on for me baby. Would you do that for me – wear the panties you bought me? You make me so happy – the way you’re willing to do all these things to turn me on. Twirl for me my little panty wearer haha! So hot. Tell me you’d suck a cock for me in those panties baby. It would turn me on so much to hear you say you’d do that for me. Say it for me… You actually said it! You stood in front of your webcam wearing those girlie panties and admitted you’d suck a cock to a girl who is clearly way too hot to be interested in a fucking loser like you. You’re such a fucktard – more to the point you’re my latest Sextorted fucktard. Now that we’re friends on Facebook I’m gonna send this cute video of you admitting to wanting to suck cock in your pretty panties… unless you pay me $500 right now – you have 1 minute loser hit send and pay me my money! Good boy – you made the right decision – I really was going to send all your friends that video… but you’re not getting out of this that easily loser. I’m about to publish your video on YouTube – unless of course you convince me not to… with another $500. Pay it now panty-cocksucker haha! hit Send again right now. You can see how this is gonna work right loser… I’m going to keep demanding money until I’ve totally rinsed you!..

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, POV, Findom, Financial Domination, Humiliation, Degradation, Blackmail, Blackmail Fantasy, Blackmailed, Blackmailing, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Public Humiliation

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776 mb
13 min

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Mia Middleton – I’ll Unlock You When Youre Gay

Mia Middleton - I'll Unlock You When Youre Gay

Your predicament is simple loser. I’m locking you into this chastity device and I’m not going to let you out until you’re gay. It’s going to be such a fun experiment. I’ll snap the lock shut and give the key to one of the gay guys at the gym and you’ll stay all caged in that cruel little device until you submit to him for the faggot ass fucking of your life. Of course, I don’t expect your voluntary abandonment of your sexuality to be immediate. Read more

Keywords: Female Domination, Free, Femdom POV, Mia Middleton, POV, Cruel Girlfriend, Humiliation, Degradation, Chastity, Locked Dick, Cock Locked, Cock Cage, Keyholder, Forced Bi, Coerced Bi, Make Me Bi, Enforced Bi, Bi-Sexual, Orgasm Control, Orgasm Denial

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617 mb
11 min

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Princess Aurora – Reprogrammed At The Gloryhole

Princess Aurora - Reprogrammed At The Gloryhole

Whether a sissy like you can learn 2 enjoy being made to suck cock or getting fucked like a real girl isn’t actually important. What is important is that u accept that these are the services sissies are expected 2 perform. Whether you enjoy it or not is of no concern 2 me or the men who will use u & eventually it’ll be of no concern to you too. The sooner you learn to accept how you’re to be used the easier it will be 4 u. We all have our ways of getting our sissies to their lowest point of emasculation but my preferred way of breaking a sissy down is by taking her to a glory hole, 4 an extreme reprogramming course. You’ll be taken completely feminized in the most degrading whorish outfit and you’ll be forced down onto your stockinged knees, with your hands cuffed behind your back & your steel sissy collar shackled 2 an anchor point just below the hole in the wall. Your helpless, painted mouth will be held in place less than an inch away from the hole that men will push their anonymous cocks through. You’ll have literally no hope of escape from the endless stream of cocks that push through the glory-hole and into your poor untrained sissy mouth. This is how u learn to accept your sissy-status. This is the lesson a sissy needs to understand you are nothing more than an object for other men’s sexual pleasure. You’ll gag and fight it at first – but eventually you’ll submit 2 the forced-fag shame you’re being subjected to. You’ll be left like this hour hours – maybe days but eventually you’ll be freed – with cum filling your belly and splashed all over your face.

Keywords: Female Domination, Free, Femdom POV, Gloryhole, Make Me Bi, CruelGirlfriend, Cruel Girlfriend, POV, Forced Bi, Coerced Bi, Feminization, Forced Fem, Feminisation, Sissy Slut, Sissy Training, Sissies, Sissy

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592 mb
11 min

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Jessie Jensen – Beaten With My Man’s Cock

Jessie Jensen - Beaten With My Man's Cock

My boyfriend is SO much bigger an stronger than you in EVERY way! He is very much an Alpha male while you, let is face it, are nothing more than a weak beta wimp. You literally have no muscles – your whole body is puny and feeble – u should really be ashamed of yourself. I actually think my man has more strength in his cock than you have in your entire body. Haha! I told him how much u annoy me – that you send me messages telling me how beautiful I’m, that you’d do anything for me blah blah blah. I told him you fantasize about fucking me and he was furious about it. He actually wants 2 beat you the fuck up just 2 teach u a lesson. Watching my stud beat you up would be so hot – listening to u beg him 2 stop, listening you begging me 2 make him stop – while I laugh and tell him to hit you even harder. I’d love to watch him really hurt u! What would be even funnier would be to watch him slap you around with his big alpha cock. I’m going to make you kneel in front of him with your hands cuffed behind your back while he beats you with his cock. You’d better not move a muscle while he smashes his fat cock into your face or I’ll let him use his on you too. Just look up at him with your pathetic stupid face as he totally dominates u with his cock. He’ll never see you as any kind of threat once he’s rested his big heavy balls on your chin and pummelled his cock all over your face. How emasculating – on your knees as another man beats u up with his cock Haha!

Keywords: Female Domination, Free, Femdom POV, Cock Worship, Cuckolding, Cuckold, Cucky, Cuck, POV, Jessie Jensen, Humiliation, SPH, Small Dick Humiliation, Small Cock Humiliation, Dick Slapping, Small Penis Humiliation, Cruel Girlfriend, CruelGirlfriend

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574 mb
11 min

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Cruel Girlfriend – Mop Up Their Cum Puddle Cucky

Cruel Girlfriend - Mop Up Their Cum Puddle Cucky

Look at the mess my real men have made cucky – all for u! My studs have left a huge puddle of their alpha-cumloads all over the floor to give you something to clean up and I am going to video you mopping up their spunk with your tongue so they can see just what a pathetic beta-cuckold you really are. Kneel down next 2 their filthy cum-puddle and look into my camera so they can see you begging me to let you slurp up their cum from the floor. I want the guys who are fucking your girlfriend to see how much of a loser boyfriend you are. They are going to watch as I push your stupid face into their slimy cummy mess and make you lick it up. This is just the first of the humiliating tasks me and my alpha-bulls have decided to set you to keep you in your place and to enforce your cuckold status. Itis not enough for them to come over here and take your girlfriend 2 your bed and fuck her. That’s not humiliating enough – they want to totally emasculate you so that I’ll never ever see you as a real man. They fucked your girlfriend, emptied their used condoms all over the floor so u have to mop it all up and then I am going to push their discarded condoms inside your cuckold ass. You can wear their filthy, wet condoms in your ass for the rest of the day. I am going to fuck them deep into your ass with a dildo an then plug u so they stay right inside all day.

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, CruelGirlfriend, Maddie, POV, Cum Eating Instruction, CEI, Masturbation Instruction, JOI, Jerk OFf Instruction, Instructions, British Femdom, British Domme, British, UK, United Kingdom, English, Cheating, Cuckold, Cuckolding, Cucky, Cuck, Cuckold Humiliation, Degradation, Humiliation, Cuckoldrix, Cum Swallowers, Cum Eating, Cum Eating Humiliation, Hot Wives, Mean Girls

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455 mb
8 min

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