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Category: 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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287 mb
8 min

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ClubStiletto – Mistress Damazonia Pee Tease

ClubStiletto – Mistress Damazonia Pee Tease

Amazon Goddess Mistress Damazonia has her slave kneeling beside her as she sits on her toilet table. “Slave, I will train you to be my full toilet” she tells him, “but you must suffer more first and that means for now you only get to watch me pee and then you will drink it off the floor.” She tells her slave to think about it, to long for anything that comes from her body.

She starts to pee and you can see the nectar run through her pantyhose and onto the ground. “It is nice and warm and will taste so good and I expect you to lick the floor clean.” A huge puddle of pee starts to spread on the floor as she sits, then she stands up and pees some more. “I can feel it running all the way down my pantyhose” she says and then orders the slave to crawl over and lick it all up. “Do you want to be my toilet?” she asks you.

Keywords: Female Domination, Free, Femdom POV, ClubStiletto, Club,Stiletto, POV, Teasing, Tease And Denial, Tease, Denial, Cocktease, Mistress, Mistress Damazonia, Pissing, Piss, Pee, Peeing, Human Toilet, Toilet, Toilet Fetish, Toilet Slavery, Toilet Sub, Toilet Slavery, Amazons, Panty Wetting, Pantyhose

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267 mb
3 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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640*360
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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Cruel Girlfriend – Becky Dee – Losers Eat Their Own Cum

Cruel Girlfriend - Becky Dee - Losers Eat Their Own Cum

The fact you’re reading this – the description of a clip called Losers Eat Their Own Cum kinda proves you are a loser. I know you are a loser and deep down you know you’re a loser too and one thing losers need in their life is RULES. Can you guess what rule number 1 is? Losers Eat Their Own Cum! Cumming is actually a huge reward for beta wimps like u – but even when you have earned a rare pity-gasm you don’t get to enjoy it like a real man. Read more

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Becky Dee, POV, Instructions, Masturbation Instruction, Jerk Off Instruction, JOI, Humiliation, Degradation, Latex, Rubber, CEI, Cum Eating Instruction, Cum Eating, Cum Swallowers, Male Cum Swallowing

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693 mb
13 min

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Cruel Girlfriend – Becky Dee – Pimping Out You & Your Girl

Cruel Girlfriend - Becky Dee - Pimping Out You & Your Girl

Total and utter sissy exposure is what you are going to get today! No short-sharp fix of humiliation to keep you submissive and horny but a prolonged humiliating ordeal with permanent exposure! You must be wondering what we’ve got planned for you sissy? Wondering how we could possibly be so cruel as to have your permanently exposed as a sissy. Well it is easy for girls like us – take a look at ou twitter profiles and see how many followers we have. THOUSANDS! And our girlfriends – THOUSANDS MORE! Between me and my bratty girlfriends we probably have close to a million followers who are reading everything we write, looking at every picture we post and watching every video clip we upload. Read more

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

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707 mb
13 min

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