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Tag Archives: Cruel Girlfriend

Cruel Girlfriend – Mia Middleton – Feminized and Strap-on Gangfucked – Humiliation

Cruel Girlfriend - Mia Middleton - Feminized and Strap-on Gangfucked

I’m going to dress you like a bitch and fuck you like a bitch and you’re going to moan like a fucking bitch for the camera – understand bitch? Haha! My girlfriends are coming over in a short while – we’ve got such cute outfits for you to wear – you’re going to dress up to please our big plastic cocks like the cock-teasing little slut you are. Put on a pretty sissy uniform so I can use you like a submissive fuck-doll and turn you into our obedient feminized whore. We’re going to make you beg us all to fuck you – humiliate yourself by kneeling in front of our big strap-on cocks and beg us to put you on all fours in that girlie outfit and fuck you. When we’re done laughing at you for being so fucking pathetic – we’ll push you down and force our cocks into you. We’re going to spit-roast you and treat you like a cheap whore at a bachelor party. I’m gonna fuck you from behind sissy while my best friend fucks your throat. You’re going to learn what it is to be a cheap sexual favour. We’re going to fuck you without mercy – ramming our cocks into each end of you while we laugh and high-five each other. You’re pretty, delicate panties are going to offer no protection from my huge, hard strap-on cock. I’m going to push your face onto my bestie’s cock and enjoy every second muffled moan of shameful pleasure you take from being force-fucked by 2 hot girls. Every minute of your emasculating gang-fucking from me and my bestie are going to be recorded and then shared with all of our girlfriends!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Mia Middleton, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Strapon, POV Strap-On, Strap-On, Strap On, Dildo, Pegging, Slave Training, Submissive Training, Sub Training, Slut Training, Humiliation, Degradation, Verbal Humiliation

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663 mb
12 min

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Cruel Girlfriend – Kiki Daniels – Call Her While I Peg You – Humiliation

Cruel Girlfriend - Kiki Daniels - Call Her While I Peg You

So my best friend is out of town for the night and she’s left you here all alone huh? Thought you’d play your sissy girl games while she was away did you faggot? Haha you like me calling you that, faggot? That’s what you are isn’t it? You’re a sissy FAGGOT. Dressing up in girls clothes every time your girlfriend goes away – I should probably tell her y’know – she is my best friend after all. Girls should stick together over this kinda stuff – outing faggots like you. But I guess I could have some fun with you instead. I could keep your secret all to myself and hold it over you to make you do things for me – humiliating things. Ever thought what it would be like to be blackmailed by your girlfriend’s hot best friend – blackmailed into doing humiliating things? That’s what I’m going to do to you sissy. I’m going to make you do the most humiliating things to keep me quiet about you being a sissy faggot. Y’know what you’re gonna do for me tonight? You’re going to call your girlfriend and ask her about her day and stuff – while I fuck your faggot ass with my strap-on. Don’t want to do it faggot? Well that’s too bad. You’re gonna be tied to the bed with my big cock pounding into your ass while I put my best friend on speakerphone for you. You’d better learn to take cock like a good faggot and take your ass fucking quietly or she’ll know what’s happening to you. Tell her how much you’re missing her while I give you the most emasculating pegging of your life. Tell her you can’t wait to see her again as I fill you full of my big plastic cock. Hold back your tears faggot – you don’t hang up until I’m done with you!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Kiki Daniels, POV, Forced Bi, Coerced Bi, Make Me Bi, Enforced Bi, Strapon, POV Strap-On, Strap-On, Strap On, Dildo, Humiliation, Degradation, Verbal Humiliation, Pegging

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645 mb
11 min

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Cruel Girlfriend – Katie Thornton – Cuckold Business Cards – Humiliation

Cruel Girlfriend - Katie Thornton - Cuckold Business Cards

So, it looks like you’ve been a good cuckold and collected all the business cards from your guy friends, colleagues and every other guy you know. You really do know a lot of people which is going to be so good for me because every time i want to fuck – I’m going to pick a card and you’re going to call them for me. I’ll select a card at random any you’ll call whoever’s card it is and invite them over to fuck your girlfriend. All your friends want to fuck me anyway, so this game is going to make sure they all get their chance – eventually! Guys are going to be fighting to give you their business cards once they’ve heard about my business card lottery. It’s going to be great – I can’t wait to hear your trembling voice as you stutter down the phone about how much I want to fuck whoever it is. Oh, and I want you to tell them WHY I’m going to fuck them. You can tell them I cuckold you because you’re just not man enough to fuck me properly and that I need a real man to come over to show you how it’s done! That should be so fucking humiliating for you! They’re all jealous of your beautiful young wife but they’re all about to find out you don’t even get to fuck me. They’re all about to get the chance to fuck me like you aren’t allowed to and best of all – you have to swallow your pride and invite them over – one by one. From now on, every time you’re passed a business card – it’s going into the lottery so I’m never going to run out of new guys to fuck right under your cuckold nose.

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Katie Thornton, POV, Cuckolding, Cuckold, Cucky, Cuck, Humiliation, Degradation, Verbal Humiliation, Office Domination, Hot Wives, Cheating

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611 mb
11 min

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Cruel Girlfriend – Jessie Boulevard – Keeping You Locked to Keep You Shrinking – SPH

Cruel Girlfriend - Jessie Boulevard - Keeping You Locked to Keep You Shrinking

I know you trusted me with the keys to your chastity device and that I agreed to release you, but I don’t see the point of doing so. Your extended term in chastity has had a remarkable effect on the size of your cock- shrinking it down by an inch already. I guess I’m curious to see how much smaller I can make it by keeping you locked in chastity for another year.
Aw come on – a year isn’t that much and besides, you’re already at a size that makes your cock completely useless to any woman. I’m sure you wouldn’t ask a hot dominant girl like me to release you from chastity just so that you can jerk off right? So again, why should I unlock you? Now that your helpless cock is shrinking away through its inactivity and inability to get hard, I want to reduce it to a size that is worse than just useless. I want it humiliatingly small. I’m going to keep you locked in chastity for so long that once you’re finally released, you’ll wish it was hidden inside it’s pink cage.
The humiliation of your chastity device being exposed to hot, bratty mean girls will be nothing compared to the shame of having your tiny naked cock on display. I want every girl to see your shrunken micro-penis so that they can laugh in your stupid embarrassed face. I’m going to get all my girlfriends together to tell them about the little chastity experiment I’ve put you through. How I locked you up just to shrink your cock and ruin your sexlife forever. They are gonna cry with laughter when the see the results – and that’s exactly the reaction you’re going to get from every girl that sees it.

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Jessie Boulevard, POV, Chastity, Locked Dick, Cock Locked, Cock Cage, Keyholder, Humiliation, Degradation, Verbal Humiliation, SPH, Small Penis Humiliation, Small Cock Humiliation, Small Dick Humiliation

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708 mb
12 min

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Cruel Girlfriend – Mila Amora – The Cum Tax Calculator – Instructions

Cruel Girlfriend - Mila Amora - The Cum Tax Calculator

You’re a loser but even losers need to cum sometimes, I guess. When you’re desperate and horny from all the real-life sneers and rejections from pretty girls – you log in to CruelGirlfriend for your fix of humili-porn to get you off right? But you know the rules don’t you loser – you understand that cummies don’t come for free. You know that your status means that you need to beg us to let you cum and then you have to pay for it. Uh-huh loser, you have to open your wallet and pay us for your permission to splat your loser-goo into your tissue. Hot girls like me know that betas like you will pay pretty much anything for that permission to cum but we think there should be a system that decides just how much your cum tax should be – which is why we invented the Cum Tax Calculator. Check it out at the bottom of the screen – the more fun you have – the more it’s gonna cost you loser. So the longer you’re jerking your cock the higher that cum tax is gonna be. The meaner the humiliation you get from me – the higher that cum tax climbs. The sexier I am as I ridicule the fuck out of you – the bigger that tax gets. When you cum you can see what your cum tax is and send it to me – you don’t get to cum again until that cum-tax is settled. So start jerking your cock as I stamp all over your masculinity and tell you just what a loser you are. Watch that tax calculation increase with every second you’re being laughed at and humiliated – you’d better cum quick faggot or you’re gonna end up in serious debt!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Mila Amora, POV, Findom, Financial Domination, Humiliation, Degradation, Verbal Humiliation, Instructions, Masturbation Instruction, Jerk Off Instruction, Jerkoff Commands, JOI, Jerk Off Encouragement, Masturbation Encouragement, Edging Games, JOI Games, Masturbation Games

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760 mb
12 min

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Cruel Girlfriend – Lucie Jones – I Want to Get Caught – Teasing

Cruel Girlfriend - Lucie Jones - I Want to Get Caught

Of course I’m cheating on you – I’m hotter than you deserve, younger than you deserve and fitter than you deserve. Of course I’m fucking other men – I don’t even try to hide it. In fact, I want to get caught. I want you to feel the stomach-turning jealousy when you catch sight of HIM with his hand on my ass. This is the relationship I want with you – you’re going to be my submissive cuckold boyfriend – we’ll live, pretty much, just like a regular couple. You’ll work hard and bring your paychecks home to me. You’ll worship and serve me and treat me like the princess I am. In exchange – I will be a complete bitch to you.

You will watch me take great delight in cheating on you with so many men. I’ll even ask them to pick me up from home, so you have to witness me greeting them with a passionate kiss, their hands all over your girlfriend. I’ll humiliate you right in front of my date – telling you not to wait up for me and that if you’re lucky I’ll bring home his used condoms to play with. I’m going to love rubbing my infidelity in your face allowing my lovers to mock you for taking your girlfriend away from you. I want you to watch me leave in my shortest micro-dress and fuck-me heels with another man’s hand on my ass. Listen to me flirting and giggling with him about you – telling him you’re just my subby cuckold boyfriend.

I know it totally breaks your heart seeing me having so much fun with other men but you’re gonna have to get used to it – I enjoy cheating on you. I enjoy making you jealous and I love humiliating you for having to assume a pathetic cuckold status in our relationship. Boo-hoo cucky!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Lucie Jones, POV, Teasing, Tease And Denial, Tease, Denial, Cocktease, Cuckolding, Cuckold, Cucky, Cuck, Cheating, Hot Wives

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706 mb
13 min

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Cruel Girlfriend – Daisy Dillon – You’ll Never Forget – Orgasm Control

Cruel Girlfriend - Daisy Dillon - You'll Never Forget

You’re going to be locked in chastity for so long you’re going to forget how good it felt to cum. I don’t want you to have any sexual pleasure ever again – losers like you don’t deserve ANY! I don’t want you getting hard over hot girls like me, I don’t want you jerking off to the thought of us or to pictures of us and I certainly don’t want you saving up all your cash and paying some girl to give you some cheap thrill. You’re staying locked in this for so long you just won’t even be able to remember how satisfying it is to empty your load. Well the good news is that I’m going to help you remember just how amazing it was to cum before I locked your cock away in chastity. You get to watch other guys cumming. You can watch porn and see cock after cock blowing their loads over all the hot fantasy girls you could only dream of. Real men don’t have to dream – they get to fuck girls like me and they get to cum. You don’t. You can watch them have all the fun, you can watch them enjoy the awesome cumshots girls like me have rewarded them with for giving us great sex. You can suffer in frustration in that device knowing you’ll NEVER get what they do. No hot girls for you – no cumming for you – just denial and blueballs in that tiny little chastity device. Maybe I’ll make you watch the real thing instead of porn. Maybe I’ll fuck a guy right in front of you to remind you how good it used to feel to cum. It’s going to be so hard for you to hear him crying out with pleasure just how good it feels knowing you’ll never get to experience that ever again. Too bad for you loser.

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Daisy Dillon, POV, Humiliation, Degradation, Verbal Humiliation, Chastity, Locked Dick, Cock Locked, Cock Cage, Keyholder, Cuckolding, Cuckold, Cucky, Cuck, Orgasm Control, Orgasm Denial

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603 mb
11 min

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Cruel Girlfriend – Becky Dee – Cuckold Wedding Night

Cruel Girlfriend - Becky Dee - Cuckold Wedding Night

Humiliating wasn’t it cucky? You followed me into the honeymoon suite after our amazing day. You looked at me in my pretty wedding dress and told me how beautiful I looked. You couldn’t wait to fuck your new bride and your poor cock was straining to get out of your chastity device. I teased you with the key and told you to beg me to let you out to consummate our marriage. It was so hot! And then you heard their laughter from the corner of the room. The 2 waiters and the barman I was flirting with all night while you were busy shaking hands were more than happy to help me totally humiliate my new cuckold husband tonight. I told them the last person I’d allow to fuck me tonight would be you cucky – that’s why they’re here – and that’s why you’re going to be staying locked up in that cock cage tonight. There’s going to be no wedding night sex for you – just for these 3 strangers who get to fuck your new hotwife in her pretty wedding dress. They get to run their hands up my stockinged legs and slip their fingers into my bridal panties. They get to bend me over and lift up my white satin dress before taking in turns to fuck me. You get to watch your perfect bride suck their cocks like a total slut knowing you’re losing your one opportunity of wedding day sex. Three strangers are taking your place on the most important night of your life. Your shiny new wife is getting used by other guys right in front of your eyes and there’s nothing you can do about it. Why don’t you just take a photo for our wedding album cucky!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Becky Dee, POV, Cuckolding, Cuckold, Cucky, Cuck, Humiliation, Degradation, Verbal Humiliation, Chastity, Locked Dick, Cock Locked, Cock Cage, Wedding Fetish, Cheating, Hot Wives

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666 mb
12 min

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Cruel Girlfriend – Mila Amora – Choose Your Life Partner – Instructions

Cruel Girlfriend - Mila Amora - Choose Your Life Partner

There comes a time when every guy, even losers like you, needs to settle down with the girl they intend on spending the rest of their lives with. It’s a big decision, right? Committing to having sex exclusively with the same girl for the rest of your life. Real men date a string of girls, fuck dozens of beautiful women until they find the one they know will give them a lifetime of pleasure. Loser beta-wimps like you don’t have that privilege. You spend years watching better men getting all the girls you drool over. You remain inadequate virgins, intimidated by hot dominant girls like me and forced to be submissive to us. You don’t get to choose a girl to be with for the rest of your life, but I am going to allow you to choose the partner you’re gonna fuck for the rest of your life. Here are your choices virgin boy. 1 – The Fleshlight 2 – The Humpy Pillow 3 – The Blow-Up Doll. Choose wisely loser because once you’ve decided upon your life partner – that’s all you’ll get to fuck FOREVER! You could spend your life filling your fleshlight with lube and jerking yourself off into your plastic pussy in front of your humili-porn. Drain your virgin cummies into the silicone tube as you accept this is the closest you’ll ever get to fucking a real girl. Or would you prefer to hump your pillow like a total loser? Take your pillow girlfriend to bed every night and rub your icky loser-stick into her until you leak your filth all over her. Imagine just how fucking gross your humpy pillow will be after just a few weeks – Eugh! Or will you fuck your pretty blow-up girlfriend? You only get one doll loser so make sure you’re super gentle with her – you won’t be replacing her if she bursts!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Mila Amora, POV, Instructions, Masturbation Instruction, Jerk Off Instruction, Jerkoff Commands, JOI, Jerk Off Encouragement, Masturbation Encouragement, Humiliation, Degradation, Verbal Humiliation, Sexual Rejection, Fleshlight, Pillow Humping

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662 mb
13 min

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Cruel Girlfriend – Miss Maisie – Your Cuckold Calendar

Cruel Girlfriend - Miss Maisie - Your Cuckold Calendar

Every cuckold should have a calendar just like this. Hung up somewhere obvious so you can’t forget all the humiliating things I have planned for you. I love the idea of you having to see all the days marked with the emasculating tasks you dread and all the dates I’m looking forward to. Oh, look on Wednesday I’m fucking your boss – that’s going to be so much fun for me and so embarrassing for you right cucky? You’ll see him on Monday and Tuesday knowing he’s scheduled to fuck your hot girlfriend after work on Wednesday. Then look who’s fucking e on Thursday – one of your best friends – can you guess who it is? Aww on Friday your new sissy maid uniform arrives – just in time for you to serve at the party on Saturday. I’ve been looking forward to having everyone see you mincing around in a sissy uniform. Serving real men drinks while I flirt with them right in front of you. Every single day there’s a humiliating situation for you cucky! A cuckold chore to keep you in your place, a new predicament to make sure you never forget your beta status. Let me see what we have planned for you today… Oh look cucky it’s your 3 months in chastity anniversary! That’s 3 long months you’ve spent with aching blue balls as I’ve tormented you with all the hot outfits I’m wearing for other guys. 3 months of no-cumming while so many Alpha guys have cum inside your little princess! You’ve earned yourself a pathetic anal-induced leak of cum from your device – why don’t you fetch you favourite dildo and we’ll get to work on your celebratory 3 month milking!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Miss Maisie, POV, Cuckolding, Cuckold, Cucky, Cuck, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Humiliation, Degradation, Verbal Humiliation, Hot Wives, Cheating

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709 mb
13 min

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Cruel Girlfriend – Mia Middleton – Sissy Exposed in the Office – Humiliation

Cruel Girlfriend - Mia Middleton - Sissy Exposed in the Office

Please take a seat. There’s been a complaint from one of our interns about you. She said that she noticed you were wearing what she believes to be bright pink girl’s panties under your work clothes. She alleged that you bent down to pick something up and she saw your obviously ultra-feminine lingerie riding up above your bottom. I have looked into her complaint and whilst no actual rule has been broken, I feel the gossip amongst the girls in the office is going to lead to a breakdown in respect for you within the office. Take down your trousers right now so I can see if the allegation is true. Don’t look so dumb – you heard me – remove your pants and let me see if you are wearing panties… OMG you actually are! You’re wearing the girliest, frilliest pink panties I’ve ever seen – you’re SO pathetic! You’re such a secret panty wearing sissy! *giggle* I suspect it’s not just panties a sissy like you enjoys wearing either – I’m sure if I stripped you down, I’d find you’re wearing a matching bra and stocking too am I right sissy? Take all your clothes off – I want to see! OMG! I told you! Sissy is dressed from head to toe in girlie pink lingerie haha! Oh seriously?.. is that a chastity device I can see through those lacy panties? Does sissy have a little locked up cock? Hahaha! Turn around – let me see your cute girlie bottom. Turn around and bend over. As I thought – sissy has a butt plug in her bottom!! This is a serious breach of office conduct missy and you’ll need to be punished! You can report to me tomorrow in FULL girly office clothes to find out what I have planned for you!

Keywords: Female Domination, Free, Femdom POV, Cruel Girlfriend, Mia Middleton, POV, Sissy Training, Sissy Slut, Sissy, Feminization, Forced Fem, Feminisation, Sissification, Humiliation, Degradation, Verbal Humiliation, Chastity, Locked Dick, Cock Locked, Cock Cage, Office Domination

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708 mb
13 min

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