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Cruel Girlfriend Della - Bimbo Factory - Secretary to Maid
 

VIDEO: Bimbo Factory - Secretary to Maid (HD)

Office hottie Della has been getting busier and busier lately and has decided she needs to employ someone to take up some of the slack. She thinks you'd make the perfect little submissive bimbo secretary. She tells you how you'd be put into a tight blouse, tiny micro skirt and high heels and forced to work at the office for her. OMG the guys in the office are gonna love you! After you've completed all of your secretary duties you're gonna come home with Della to start your evening job... her live-in french maid. That's right sissy-boi, after a hard day wiggling around the office in your heels you're gonna be expected to come home and start your sissy maid duties like a good little foo-foo maid. (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Lolly Lopez - Castrated for Cash
 

VIDEO: Castrated for Cash (HD)

Evil cash princess Lolly has squeezed almost every last penny out of you. She's had you buying her all sorts of girlie gifts and expensive luxuries but now the cash is running dry. Fortunately, Lolly saw this coming and the last gift you bought her will ensure there's still some more money to be made from you. She forced you to buy her a castration device and guess what sissy - she plans on using it on your worthless cock and balls. Lolly thinks she can make up to $5,000 selling your pathetic loser-stick on the black market. Lolly laughs at you as the reality of losing your manhood to make her money sinks in. You're gonna be left with no cock or balls so that Lolly can keep spending! She tells you just how she plans on wasting the money she gets for your castrated flesh. You get to suffer for the rest of your life so that your snobby princess can buy a new collection of lingerie! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Tuezday - Chastity Cuck Milked & Forced to Sell His Kidneys
 

VIDEO: Chastity Cuck Milked & Forced to Sell His Kidneys (HD)

Hot model girlfriend Tuezday is unobtainably beautiful to a loser like you but she wants to make herself look even more stunning with some cosmetically enhanced boobs. She's decided to get an awesome set of big boobs that you'll never get to see - even though they're gonna be funded by you. Tuezday explains how you're going to have to pay for her new implants by giving up everything your body has to offer. First of all she removes the tight chastity device you've been caged up in for months and milks you into a shot glass. Tuezday is gonna donate your loser-goo to raise some cash but the real money is gonna come from selling your organs. To pay for the big boobs her real man lovers are gonna get to play with, you're gonna have to donate your kidneys... both of them! Your not gonna be around for long after they've ripped them out of your body but that doesn't matter to Tuezday one little bit so long as she gets her huge new boobs.. Don't forget to leave everything to her in your will too cucky! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Jen - Forced-Bi Porn Slut
 

VIDEO: Forced-Bi Porn Slut (HD)

Cruel and sadistic girlfriend Jen has sold you to a porn company for $1,000. You're going to be the star of their lastest gay gangbang video. It doesn't matter one little bit to Jen that you're not gay and that you only want to fuck hot young women like her - all she cares about is taking the money and going away on vacation with her real man. A vacation you're going to be funding by getting destroyed by cock after cock after cock. You're going to be shaved and put into girlie frillies before the gang of porn studs take you away and fuck you until you're screaming into your gag. Nobody's going to come to your rescue though fag-boi. You're just gonna have to take it as each of the horny fuck-studs plough into you like a fucking train. (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Della - Eat his Condoms Until You Die
 

VIDEO: Eat his Condoms Until You Die (HD)

Stunning, cheating girlfriend Della is going out on a date with a stud tonight. She loves to cuckold you and humiliate you with the painful details of her plans for the evening. She's going to be fucking her real man all night long and filling up condom after condom with his alpha stud sperm. Della shows you all the condom packets she's going to be opening for her lover tonight and laughs at you for never getting the opportunity to use them. Della loves humiliating you with all your inadaquacies but has much more than just verbal humiliation in store for you later. She tells you that after her man has filled all of the condoms with his real-man juice, she's gonna force your to eat every single last one of them. Della is gonna make you swallow all of them... ramming them down your throat until they kill you! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Lolly Lopez - Happy Bithday Sissy
 

VIDEO: Happy Birthday Sissy (HD)

Heartlessly Cruel Girlfriend Lolly has been planning a terrifying ordeal for your birthday sissy. She giggles as she tells you that she's invited an entire rugby team to your birthday party tonight and she's going to fuck each and every one of them. You're going to stand there and watch in your sissy pink party dress, as all 20 guys bend your pretty girlfriend over and give her the alpha- male fucking you could only dream of giving her. Lolly smiles sadistically as you realise just how humiliating this is going to be for you... but it's going to get a whole lot worse. Lolly explains that once the guys have had their fun with her, they're going to do exactly the same to you to. Lolly is going to watch and laugh as the whole team push you over the bed and fuck the daylights out of you. They're gonna totally destroy you as your girlfriend watches. Your pretty little party dress is gonna get drenched in real man cum tonight sissy - happy birthday! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Crystal - Ruined Life
 

VIDEO: Ruined Life (HD)

You've been having an office affair with your stunning secretary Crystal. She knows everything about your life. She knows all about your perfect little wife and kids and your nice little house in the country. She knows you crave the excitement of cheating on your family with a hot 20 year old girl. She knows how much you want to have her wild, tight young body wrapped around yours instead of your sensible middle aged wife's. Crystal tells you that if you want her you can have her... you've just got to ditch your wife. She even offers to do all the hard work for you and call her herself. She takes your phone and calmly calls your wife and without a shread of mercy, coldly explains how you've both been cheating on her. Crystal delights in the distress of your wife, mocking her for getting upset, enjoying every minute of destroying her family. She loves ruining your wife's dreams and breaking up her marriage - it's just a game to her. After she's finished stomping all over your perfect family life, she turns her attention to you... Now it's your turn to see how evil this manipulative bitch can be. She's going to finish you off and leave you jobless, homeless, and alone! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Jen - Ruined Date Night
 

VIDEO: Ruined Date Night (HD)

Jen is furious that you've managed to talk a girl into going out on a date with you. Jen thinks you're nothing more than a disgusting weakling of a man but even though she doesn't want you anywhere near her, she also doesn't want you enjoying yourself with any other girls. She forces you to hand over your phone and quickly finds the number for Ashleigh - your hot date for tonight. Jen is in a particularly malicious mood and delights in telling you how she's going to humiliate you and ruin your date. She calls Ashleigh and starts explaining to her just what kind of sissy loser you are. She tells her how you enjoy wearing girlie clothes and how you get cuckolded. Jen finds the whole thing hilarious while you have to just stand there and listen as your new relationship is destroyed. By the time Jen is done with you, the only date you'll be going on again will be with your fist, lotion and a box of pink tissues haha!! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Tuezday - Forced Cock Tester
 

VIDEO: Forced Cock Tester (HD)

Your sadistic girlfriend Tuezday loves to think up humiliating ordeals to put you through. She never gets bored of trying out new ways of emasculating and ridiculing you especially when she has an audience. Tonight, Tuezday has an extra special predicament lined up for you. She's invited her friends over to help her test out her collection of cocks on you. She torments you by showing you the different toys she's going to be ramming up your tight girlie ass and explains how all the girls are gonna be laughing and giggling at you as you struggle to take each and every cock they pick out for you. Tuezday knows you're going to be in a desperate state of humiliation but knows she can make it even worse for you. The girls are going to video your forced sissy cock testing and send it to all your friends. Tuezday is going to make sure that everybody knows what a cock-hungry little slut you are! (Available to download in HD as well as SD)

 

 

 
Cruel Girlfriend Jasmine Jones - Prepare for her sex party
 

VIDEO: Prepare for her sex party (HD)

Cruel Girlfriend Jasmine is throwing a sex party tonight and expects the place to look immaculate before her hot guests arrive. The thought of all the beautiful girls coming tonight starts to excite you but Jasmine snaps you back to reality with a flick of her whip. She laughs at you and tells you that your chastity device will be staying on all night. You, weakling, are just the clean-up maid. Your only duties are to make sure the superior men and women have a nice clean space to fuck each other in. Jasmine decides you're going to clean the toilet with your tongue for a start. You're going to get down on your hands and knees an lick up the bathroom filth whist your cruel princess supervises your humiliating task. Jasmine has an extra incentive to make sure you do a good job too loser. She explains that if she thinks your clean-up performance is even slightly below her expectations, she's going to let your disgusting fag neighbour loose on your sissy ass. That's the deal sissy, clean up really good or you're gonna get fucked really good hahaha! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Crystal - Model Humiliation Lesson
 

VIDEO: Model Humiliation Lesson (HD)

Inviting a beautiful young model over to take pictures of her all afternoon should have been the perfect weekend treat for a loser like you. Unfortunately the model you chose was Crystal... a real life humiliatrix. As soon as she's finished posing for your sad little collection of jerk-off photos, she decides you need an introduction to the world of humiliation. She grabs a pair of her girlie super-high heels and orders you to lick them clean. She explains exactly how she wants you to lick the glittery heels to a perfect shine as you kneel submissively at her feet. After you've done a good job on her modelling shoes, Crystal decides to increase your humiliation by forcing you to clean her skater-girl housemate's skater shoes. She tells you how dirty and disgusting they are and that she wants you to slurp up all the filth right in front of her. Crystal is gonna take you into a world of slavery and humiliation whether you like it or not! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Chelsea - Peeping Pervert Gets Feminised
 

VIDEO: Peeping Pervert Gets Feminised (HD)

Creeping into your stunning girlfriend's bedroom and sneaking a look at her under the sheets while she sleeps was a big mistake loser. Chelsea is so angry with you and decides the most fitting punishment would be to feminise you and force you to work as a prostitute. You're gonna be turning tricks for her like a cock hungry little whore! Chelsea starts by picking out the sluttiest little whoring outfit she can find for you. A tiny micro skirt and a sexy little top. Then she decides you're way too hairy to be a convincing little street-girl so she gets to work shaving the hair from your body.You're gonna be the silkiest, smoothest little bitch on the scene by the time Chelsea is done with you. (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Crystal - Meet the Mechanic
 

VIDEO: Meet the Mechanic (HD)

Your hot cheating girlfriend Crystal has some bad news for you cucky. She's heading out on another date with the cocky, confident mechanic down the road. Your cruel girlfriend knows you don't like him which makes her want to cheat on you with him even more! She explains to you, as she sips her third glass of wine, how she's going to go out on another date with him and bring him back so that you can meet him. She tells you how the wine makes her turn nastier and nastier and that you're going to be in for some real torment tonight when she comes home with her real man. She tells you how you're gonna be made to serve them drinks and watch as her lover fucks her like a slut needs to be fucked - not like your weak pathetic bedroom mincing. She's going to get fucked properly tonight loser, and all you're getting is humiliation and frustration... all locked up in your brand new chastity device! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Paige Turnah - Chastity Sissy Milking
 

VIDEO: Chastity Sissy Milking (HD)

Paige Turnah and her cruel girlfriend Louise have come up with a money making scheme. After 6 long months you're finally going to get released from chastity and even allowed to cum. The girls have decided that even pathetic loser sperm like yours can be sold to research clinics and so they plan to extract your sissy-goo for their profit. Paige Turnah orders you to show them your weakling cock as Louise reveals her amazing new breasts. A joke of a man like you is lucky to ever get a chance to see such perfect tits let alone have 2 perfect princesses milk your loser-load over them. The girls insult and ridicule you as they carefully milk you - making the experience as humiliating for you as possible. All your filth is good for is earning these girls money and they're not going to make this a pleasurable experience for you. When you finally spurt out your inferior load, the girls scoop up every drop to send away - you're left with their spiteful words ringing in your ears before they lock you away for another six months. (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Tuezday - Sissy Cuck sent to Die in Thailand
 

VIDEO: Sissy Cuck Sent to Die in Thailand (HD)

Heartlessly cruel girlfriend Tuezday has nothing but absolute contempt for you. She hands you a sex toy and orders you to make her cum. She thinks you're just a disgusting, pathetic loser and you should think yourself lucky that she even allows you the honour of giving her some pleasure with her toy. It's the closest you're ever going to get to having sex with a beautiful woman so you might as well make the most of it! Tuezday totally ignores you as she enjoys her orgasm - you're nothing to her and you never will be. She couldn't care less if you lived or died... Which is exactly what's going to happen to you very very soon. Tuezday has been planning a terrifying ordeal for you that's going to earn her a lot of money. She's having you sent out to Thailand to get totally feminised just like the pretty ladyboys. You're going to be given big fake tits and special makeup to make you look as girlie as can be so that you can work the streets as a sissy hooker. You're going to be selling yourself on the Thai streets and earning somebody a LOT of money. Of course the girls don't last very long out there and you'll probably end up dead pretty soon. But Tuezday's not going to care one little bit - she's just sold you for $5k... What nasty little end awaits you is of no concern to her whatsoever!! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Gemma - Blackmailed Bank Manager
 

VIDEO: Blackmailed Bank Manager (HD)

Hot humiliation princess Gemma has you just where she wants you. She's been dressing you up in sissy girlie clothing for months and has built up a whole portfolio of evidence on you. She sneers at you and asks what would happen if the girls at the bank found out about how you love to put on pretty pink panties. Gemma thinks you're pathetic and disgusting and knows that the office girls would think even worse of you. She asks how your precious family would react if they knew you were dressing up like a sissy girl. She knows your wife would throw your pantied ass onto the street and divorce you. You have no choice but to continue to suffer Gemmas humiliations and mind games - she has you just where she wants you. She can ruin your entire life at a whim. So go get your frilly pink dress sissy... (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Tuezday - Watch me shave cucky
 

VIDEO: Watch me shave cucky (HD)

Cuckolding trophy girlfriend Tuezday is getting herself looking perfect for her hot date tonight. She forces you to kneel in front of her as she opens her long golden tanned legs and starts to shave her cute little pussy. This is an honour for a pathetic cuck weakling like you and the closest you're ever going to get to fucking her. Tuezday almost completely ignores you as she makes herself silky smooth for the real men she's going to be bringing back tonight. The only acknowlegement you get is her instructions for the evening. While she's out partying with the studs who'll get to fill your girfriend full of cum tonight, you're going to be cleaning the house and preparing the bedroom for them. Tuezday tells you that when she gets home later, you're going to sit in the spare room and listen as her studs fuck her nice smooth pussy and treat her like the cheating little cock-slut she is. Try not to cry tonight cucky! (Available to download in HD as well as SD)

 

 
Cruel Girlfriend Chelsea - Cheaters get locked up!
 

VIDEO: Cheaters get locked up! (HD)

Cheating on a cruel girlfriend like Chelsea is gonna get you severely punished. Cheating on her with her own sister is going to ruin your life! You may well have been drunk and didn't know what you were doing but this little mistake is going to cost you your sex life. Chelsea is locking up your cock in an emasculating chastity device where it's gonna stay for a VERY long time! No more cheating, no more cumming, not even a hardon until Chelsea decides to set you free. You're going to suffer in frustration and denial for as long as it takes for Chelsea to forgive you... and don't expect that to happen any time soon loser. Oh and Chelsea isn't gonna leave your punishment at a humbling cock-lock. Chelsea also has a used condom full of punishment for you to slurp up! (Available to download in HD as well as SD)

 

 
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Cruel Girlfriend Ivy - Sex Party Serving-Sissy

VIDEO: Sex Party Serving-Sissy (HD)

Beautiful, blonde, trophy girlfriend, Ivy, has invited all her hot young friends to her VIP sex party - everyone she knows is coming... except you loser. Why would she want a pathetic weakling excuse of a man like you there? No, losers like you don't get invited to sex parties with stunning women... unless of course it's to serve drinks or to keep the dirty used condoms cleaned away so that the beautiful people can enjoy themselves. Ivy thinks it would be a good idea if you helped keep the place clean and the guests served while they have all the fun you could only ever wish to have. Ivy, explains that she expects you to do an excellent job too otherwise there will be serious repercussions... like the last time when she punished you by letting you get fucked by the local gay tramp. (Available to download in HD as well as SD)

 

Cruel Girlfriend Jasmine - Chastity Loser Wears a Strap-on

VIDEO: Chastity Loser Wears a Strap-on (HD)

Having a girlfriend as perfectly gorgeous as Jasmine should be the most a guy could ever wish for. Unfortunately for you cucky, Jasmine loves nothing more than treating you like the pathetic beta male weakling you know you are and takes every opportunity to totally humiliatie you. Before she leaves you for another night while she goes out on a date with a real man, she shows you the emasculating chastity device you're going to be locked into tonight. It's a heartbreaking twist in your relationship. She explains that from now on the only sex you're going to get is by wearing a strap-on over your cock-lock. The good news is that you're going to get to fuck your beautiful girlfriend just like all her alpha male boyfriends. The bad news is that you're not gonna feel a thing. Your useless little cock is going to stay all squeezed inside it's little prison, unable to get hard, unable to cum, unable to feel any pleasure for eternity! (Available to download in HD as well as SD)

 

Cruel Girlfriend Chelsea - Sissy Outfit Tester

VIDEO: Sissy Outfit Tester (HD)

Your Stunning cheating girlfriend Chelsea is getting ready for a night of fucking with her real man. She looks unobtainably gorgeous in her cute little dance outfit but because there's no mirrors in the apartment she has no idea just how hot she looks. Chelsea has a plan, she's going to force you into her girlie clothes so she can see exactly how it looks. You're going to have to model the clothes your girlfriend will be wearing while her real man is pounding her full of cock. Chelsea giggles as she makes you step into her little ballet tutu. How humiliating is it to be wearing a little lacy tutu in front of your hot young girlfriend? She pulls up your girlie thigh-high socks and laughs at you as you try to stand in the oh-so high heels she's picked out for you. Not only are you her cuckold - you're her pathetic girliefied sissy cuckold hahaha! (Available to download in HD as well as SD)

 

Cruel Girlfriend Ivy - Pillow Fucker!

VIDEO: Pillow Fucker! (HD)

losers like you can only dream of fucking a girl as hot as Ivy Summers. She has a pretty face, big tits, a perfect tight little ass and the cutest come-fuck-me voice. Losers like you will only ever get humiliated, laughed at, ridiculed and abused by girls like Ivy. Which is exactly what she has planned for you today. She thinks it's hilarious that you're still a virgin, and wants to totally shame you for it. She throws you a pillow and demands you to start fucking it. She's going to totally humiliate you while you lose your virginity to a girlie pillow. She spits insults at you as you squirm into your loser fuck-toy. Then she tells you that while you're fucking your pillow like a pathetic freak, she's going to go into the next room and fuck her real man. You're gonna have to pump your load into your soft fabric fuck-friend while your stunning princess moans and screams in pleasure in the next room. You're such a freako loser! (Available to download in HD as well as SD)

 

Cruel Girlfriend Della - Pay For Your $i$$y A$$fucking

VIDEO: Pay For Your $i$$y A$$fucking (HD)

Hot cuckolding princess Della is heading out to the club tonight. She's making a real mess in the bathroom with all her make-up and decides the best way to clean it up is to force you to slurp up the filthy muck accumulating in the basin. After she's made you lick up her makeup scum, she explains to you what's gonna happen tonight. You're going to accompany your hot young girlfriend to the club, where she has arranged for you to meet 2 very horny gay guys. She's handing you over to them to get your sissy holes ruined and to top it all off - you're gonna have to pay for the priviledge too. You're going to give them your money and they're going to fuck the daylights out of you while your pretty girlfriend has her own fun with a real man of her own. (Available to download in HD as well as SD)

 

Cruel Girlfriend Paige Turnah - Sold into Sissy Slavery

VIDEO: Sold into Sissy Slavery (HD)

Cruel Gangster Girlfriend Paige Turnah has called you over to discuss her latest shady business venture. Paige is part of one of the biggest gangster families in the country and she's totally ruthless when it comes to exploiting sissy losers like you. She explains that she's going to have you completely feminised - given huge breast implants and then sent out to the Middle East where you'll be sold to a rich Arab. She's going to sell you to a wealthy business man who wants a permanent sissy fuck doll. Paige shows no mercy at all as she spells out your life of sexual servitude. She knows you'll do exactly as you're told to do otherwise you'll have her sadistic gangster family to deal with. She smiles as she sees the desperation on your face slowly turn to acceptance of your pathetic new life as a sissy slave girl. (Available to download in HD as well as SD)

 

Cruel Girlfriend Chelsea - Fat Fairy

VIDEO: Fat Fairy (HD)

Cheating girlfriend Chelsea has some humiliating abuse for you. She stands there in front of her hot girlfriend insulting you and letting you know exactly what she thinks of you. You have nowhere to hide as the 2 beauties stare at you while Chelsea mocks you and spells out all the reasons you're just a pathetic sissy cuckold. She tells you that while she's getting the fucking of her life tonight with her real man, you're going to be parading around in a sissy tutu, playing the part of a fat fairy. How humiliating... not only will you be laughed at by your stunning cruel girlfriend but you're gonna get humiliated in front of the man who's taking your place in her bedroom! (Available to download in HD as well as SD)

Cruel Girlfriend Louise Jordan-  Condom Slurping Chastity Cuck

VIDEO: Condom Slurping Chastity Cuck (HD)

Stunning Girlfriend Louise Jordan has a nasty surprise for you today cucky! She's just fucked a complete stranger in public. The whole neighbourhood just watched your hot girlfriend cheating on you with a real man in the middle of the street. She knows you're going to be the laughing stock of the area and loves the fact that she's publicly humiliated you. Public humiliation is only half of todays shame for you though cucky because Louise wants to humiliate you further now that she's home. She reaches inside the expensive purse you bought her, and pulls out a disgusting, slimey condom full of the lucky stranger's cum. She teases you with it, making you watch as she empties the gross cumload onto the floor. She's going to make you get down on your knees and slurp up all of his sperm as she stands over you, mocking you for being a pathetic weakling cuckold. As humiliated as you may feel, this is only the beginning for you cucky! Louise has more cum eating shame planned for you today. She unlocks your useless cucky-cock from it's chastity cage to milk some loser-goo from your sissy balls... she's going to use your own filth to totally degrade you with... (Available to download in HD as well as SD)

 

Cruel Girlfriend Nina Leigh - Help the Homeless

VIDEO: Help the Homeless

Your hot girlfriend Nina Leigh has taken charity to a whole new level. She has invited 2 homeless men back to your apartment for a party this evening and a place to stay. Not only that, but she's throwing your sissy services in to the deal too. Nina is going to humiliate you in front of your 2 new homeless friends before letting them both fill your sissy holes with their hobo sperm. She treats you with total contempt as she tells you how they will all laugh at you while they humiliate you and then fuck you like the little charity whore you are.

 

 

Cruel Girlfriend Lolly Lopez - Sell the Ring and Ruined

VIDEO: Sell the Ring and Ruined (HD)

Your stunning girlfriend Lolly has found the engagement ring you were planning to give to her. She finds it hilarious that a pathetic married loser like you could think for one second that she'd agree to getting engaged to you. Lolly has been seducing you for months, draining the cash slowly from your wallet as she gets her claws deeper and deeper into you. Now that she's got you exactly where she wants you, she's going to take such delight in totally ruining you. She tells you she wants you to take the expensive ring back to the shop and bring her the cash instead. You're never going to get a hot young girl like Lolly to marry you - all she's interested in is your money and the amusement it gives her to watch your life crumble. She explains to you that she's going to tell your wife everything. How you spend all your money on Lolly's expensive lingerie, how you do everything she says and that you've blown a fortune on an engagement ring for her. She tells you it's not blackmail - she's going to ruin you whatever you do. It's just a cruel game to Lolly - she wants to see you lose everything and end up homeless. (Available to download in HD as well as SD)

 

Cruel Girlfriend Paige Turnah - Sissy Cuck Forced to Steal

VIDEO: Sissy Cuck Forced to Steal (HD)

Your stunning cheating girlfriend Paige Turnah has had a wickedly humiliating idea. She's decided she's going to force you into girlie clothes. She picks out a cute dress for you to wear and a pair of high heels for you to wobble around on. She finds it so funny that when she sends you out into public in all this girlie clothing everybody is going to see you're a man dressed as a girl. Everyone is going to laugh and point at you. Paige isn't just sending you out on a humiliating walk around the mall though sissy. No, your hot cruel girlfriend has an assignment for you to complete while you're wiggling around in public. She wants you to visit her favourite lingerie store and STEAL a pretty little panty and bra set for her. Not only will everyone be pointing, giggling and laughing at you, in your dress and heels, but you're gonna have to steal lingerie at the same time... Good luck sissy! haha! Oh and while you're out stealing panties for Paige, she's going to be treating a real man to all the bedroom fun he can handle. Real-man sex for him - sissy humiliation for you! (Available to download in HD as well as SD)

 

Cruel Girlfriend Jen - Jen's Cleaning Servant

VIDEO: Jen's Cleaning Servant (HD)

Being the obedient little cleaning servant of a young, hot, cruel girlfriend like Jen is a thankless existance. No matter how hard you try to please her, she's never happy with you. You spend your whole life taking care of her every need, keeping her apartment clean and tidy and all you get in return is her mean insults and humiliation. She's inspected your hard work and has nothing good to say about it. You're going to have to re-do the whole lot and next time you're going to be using your tongue to clean her bathroom! You're gonna learn one way or another so while she's out having fun this weekend, you're gonna be on your hands and knees scrubbing her floors and washing up like a good little housemaid. (Available to download in HD as well as SD)

 

Cruel Girlfriend Vicky - Sissy Sold into Porn

VIDEO: Sissy Sold into Porn (HD)

Your hot bitchy girlfriend Vicky wants to take a vacation with the girls. She plans on spending some time in the sun partying with some real men. She tells you that she wants to take a lot of money with her. To spend on cute little bikini sets to please the boys and lots of drinks to get her and the girls in the mood for partying. Vicky has come up with a humiliating plan to exploit you for cash. She's going to get you all dressed up like a cute little girl and force you to work in the porn industry. Don't expect a nice girlie lesbian shoot either sissy. Na-ha! Vicky is going to have you sucking on big black cock in emasculating gay porn movies. Vicky has picked out a cute little outfit to put you into and teases you with the details of the predicament you're going to find yourself in - bent over with your pretty skirt up over your ass as a big black porn stud fucks you like a slut. You're gonna have to shoot a lot of movies to pay for Vicky's luxury vacation sissy so you'd better get used to taking cock! (Available to download in HD as well as SD)

 

Cruel Girlfriend Lolly Lopez - Pay Princess Abuses You

VIDEO: Pay Princess Abuses You (HD)

Arriving at your hot young pay-princess's apartment with some beautiful flowers should have been a good idea. But Lolly is already in such a bad mood with you so flowers just isn't gonna cut it! She snatches the gift out of your hand and instantly abuses you for buying her a sub-standard bunch of flowers. She hates the colors, she hates the type of flower and most importantly, she hates the value of them. She's furious you've been spending money on yourself without her permission. She knows you've bought a pair of expensive trainers for yourself and she's not gonna let you get away with it. She's your financial dominatrix and you're nothing more than her pathetic loser pay-pig and your cash is her cash! She takes your new trainers from your feet and spitefully throws them away. She gets so much pleasure telling you to go to the ATM for cash without anything on your feet. She doesn't care about you at all loser - all she cares about is your cash - so hobble off and get her some money weakling. (Available to download in HD as well as SD)

 

Cruel Girlfriend Jasmine Jones - Mean Meal

VIDEO: Mean Meal (HD)

Your stunningly beautiful trophy girlfriend, Jasmine, is taking you out for a nice anniversary meal at a very expensive restaurant. She's endured 4 years being with you, her hoplessly pathetic cucky weakling of a boyfriend and plans to make it a humiliating date night for you tonight. She knows all the waiters that work at the restaurant. They're all hot young guys that she's been secretly fucking behind your back and they're all very happy to help her humiliate her cucky boyfriend! She's going to ask the waiters to squirt their extra special cummy sauce all over your salad. Keira tells you that all the waiters will take turns jerking off into your food and you're going to eat it all up while they all stand there laughing as you eat the gross mess. When you've finished, Keira is going to go out the back with all of them for some fun while you savour the disgusting taste left in your mouth. (Available to download in HD as well as SD)

Cruel Girlfriend Jen - Chastity Cuck's Sex Lesson

VIDEO: Chastity Cuck's Sex Lesson (HD)

Your hot cheating girlfriend, Jen, is on the phone with her stud - finalising their plans for your humiliating cuckolding lesson. Jen wants you to understand why you're the cuckold who never gets to fuck her, and why he's the stud who gets to do whatever he wants to with her. Jen is going to lock you up inside a tight plastic chastity cage and make you watch your rival fuck the daylights out of her. You're going to have to suffer in your device and watch as a real man gives your girlfriend the sort of pleasure a cuckold loser like you could only dream of giving her. Then, just so you know where your inadaquacies are, Jen is going to let her stud fuck you like a bitch. Only then will you understand the difference between a cucky little weakling like yourself and a fuck-monster like him. (Available to download in HD as well as SD)

 

Cruel Girlfriend Amy - VIDEO: Housemaid Humiliation

VIDEO: Housemaid Humiliation

Cheating girlfriend Amy is going out to meet her real man. She's leaving you behind to cook a delicious dinner for them when they come back. She explains how she's planning a night of fucking her stud while you look after them, serving them their meal. Amy shows you the humiliating little uniform she wants you to wear while you play the obedient housemaid. You're going to look so pathetic in your little skirt and Amy takes great delight in telling you how much her man is going to laugh at you when he sees you wiggling around the kitchen as you carefully prepare their dinner.

Cruel Girlfriend Emma - 2 Girls Fuck On You

VIDEO: 2 Girls Fuck On You

Emma has invited her girlfriend, Amy, over to help humiliate you. The two girls want to show you exactly what you're missing by turning you into their mattress as they fuck each other on top of you. Amy has a big fat strap-on cock to fill your pretty girlfriend's pussy and all you'll get is to watch from below. Humiliated by the two girls, you'll just lay beneath them and listen to them moan as Amy pumps your girlfriend over and over. Then, after the girls have had their fun, it's your turn...

 

 

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