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Cruel Girlfriend Nina Leigh - Cucky's Eyes Wide Shut Night

VIDEO: Cucky's Eyes Wide Shut Night

Your beautiful girlfriend Nina Leigh is dressed to kill in her cute little black dress and heels. She's a guest at a super-exclusive VIP adult party. She teases you with details of how she's going to fuck some of the hottest guys and girls on the scene while she leaves you locked in chastity at home, dreaming of what it would be like to have a tiny slither of pleasure with her. She takes such an evil delight in tormenting you but as she cruelly explains how your cucky life is destined to be, she thinks up a devilishly spiteful plan for you. She decides you're going to come to the party with her... Not as her escort though loser... No, Nina's going to turn you into the perfect FEMALE party guest. She picks out a sexyy little outfit to dress your girlie body up in, a cute little wig and even finishes you off with pretty makeup. She laughs as she tells you how you're gonna be passed from man to man tonight - forced to accept every depraved fantasy they want to inflict upon you. The new girl always gets the most action sissy!

 

Cruel Girlfriend Rachel - Humiliating Task Game

VIDEO: Humiliating Task Game

Rachel and Becky have created a humiliating spin-the-bottle game to play with you. They've made up some totally spiteful tasks for you to complete and take SO much pleasure in supervising each and every one of them. These girls absolutely love handing out each humiliation, hitting you with heartless verbal insults and laughing at you as they help each other think up new ways to be cruel to you. You have no choice but to take everthing these beautiful young girls hand out to you.

 

Cruel Girlfriend Lara - Girls Night Out

VIDEO: Girls Night Out

Party girl Lara is going clubbing tonight and she's decided to let you come too. It's not going to be the sort of date you're hoping for though sissy. Lara has no intention of spending any intimate time with you at all. She needs another girl to accompany her to the club and that girl is going to be YOU. She picks out some totally girlie clothes for you, a pink corset, a teeny tiny miniskirt and some very sissy accessories. You're going to stand out that's for sure! With your cheerleader pom poms and high heels you'll look like such a bimbo. Lara also has a plan to help you pay for the whole night too sissy - a VERY humiliating plan!

Cruel Girlfriend Louise Jordan-  Locked up and forced to watch

VIDEO: Locked up and forced to watch (HD)

Your hot girlfriend Louise is so mean to you! She talks to you with utter contempt and total disgust. She hates you and just loves to let you know it! She delights in humiliating you with her best girlfriend and tonight is going to be another chance for the heartless duo to give you a dose of humiliation. Louise shows you the cruel chastity device she's locking you inside while the girls go out partying. She shows you the slutty pink dress she's going to force you to wear while you wait for them to come home... and they're not coming home alone either cucky! Louise tells you all about the alpha male studs the girls are going to be bringing home with them tonight. She explains how you're going to be forced to sit there, crammed inside your chastity cage while the 2 hot beauties kiss each other and then fuck their real-man lovers right in front of your pathetic cuckold face. (Available to download in full HD as well as SD)

 

Cruel Girlfriend Sara - Bride of Cucky

VIDEO: Bride of Cucky

Getting married to a stunning girl like Sara would be every mans dream, but Sara has some extra plans for your wedding day that will turn your dream into a cucky nightmare. She's going to be inviting all the guests back to the honeymoon suite for a huge orgy. She thinks it would be a great idea to spend her first night as your new wife, fucking and sucking as many men as possible. You're not even going to get to see it either cucky. Sara is going to leave you outside the bedroom, dressed in your humiliating wedding day outfit as she has all the fun. You'll only get to peek throught the keyhole and listen as your hot new wife cheats on you all night long. The wedding isn't for a few days yet though cucky, so Sara is going to spend the time practicing for the orgy by inviting her new gym instructor back tonight. You're going to be able to practice being the perfect little cuckold husband too, by preparing the bedroom, and bringing them strawberries and champagne as your cheating fiance and her real man laugh at you.

 

Cruel Girlfriend Amy - VIDEO: Picnic Cuckold

VIDEO: Picnic Cuckold

Cheating girlfriend Amy is meeting her girlfriend and boyfriend in the park for some outdoor action. You've been invited along for their entertainment. Amy verbally abuses you for being so pathetic, explaining how you can't satisfy her like her lovers can and why she has kept you in long-term chastity. You are reminded of your position in her life as her humble cuckold, expected to serve her and her lovers, bring them food and drink and make sure their every whim is catered for. In exchange you get nothing but her contempt and ridicule.

 

Cruel Girlfriend Jen - Sissy Cuckold Workout

VIDEO: Sissy Cuckold Workout

Your cruel cheating girlfriend Jen is in a particularly malicious mood today cucky. She's dragged you down to the local gym to show you exactly where her hot gym instructor has been giving her the sort of workout you could only dream of giving her. She delights in rubbing your nose in all the tiny details about their affair. She loves to see the heartbreak in your pathetic cuckold eyes as she tells you how she plans to meet him later by the fire escape so they can both show you how to treat a hot girl like Jen. You're going to have to stand there and watch as the strong, muscular gym instructor fucks your girlfriend right in front of you. Your humiliation has only just begun though loser, Jen wants to throw much more shame at you than simply cuckolding you - she's going to force you into her cute pink gym kit and make you watch the whole thing dressed up in the humiliating kit. Then when he's done fucking your girlfriend - it's your turn gym girl. The heartless couple are going to force you to bend over and take his real-man cock like the weak little cucky bitch you are as your girlfriend watches and laughs at you. To top the whole ordeal off, Jen has one final public humiliation assignment for you to endure... A sissy workout at the gym.

 

Cruel Girlfriend Becky - Forced-Fag Double Date

VIDEO: Forced-Fag Double Date

Becky and her real man are going out on another hot date tonight and thought it would be a good idea if you came along to keep his best friend company. His best GAY friend that is! Becky's picked out the perfect sissy bimbo outfit for you to wear for him, and she carefully applies your pretty makeup to make you look like such a cute little bitch. She wants you to make the right impression, and doesn't want you to embarrass her in any way. She tells you that your new boyfriend for the evening LOVES to have his huge cock sucked and she expects you to give him the very best VIP sissy blowjob he's ever had. You're going to be forced-fed fag cum tonight sissy!

 

Cruel Girlfriend Emma - Cucky's New Job

VIDEO: Cucky's New Job

Cuckolding girlfriend Emma is getting ready for another hot date with her real man. You can only watch as she prepares for her evening of pleasure with your rival. You can dream and try to imagine what it would be like to enjoy some quality time with a girl like Emma, but you're only ever going to be the pathetic little cuckold in her life, working hard and bringing home the cash so that she can go out and have fun at your expense. Fortunately, Emma has arranged for you to start another job, to earn even more money for her and her lovers. You're going to be working as a serving maid - complete with sissy french maids uniform and impossible heels. Emma relishes your humiliation as you realise just how embarrasing you new position is going to be for you but you have no choice - your the cuckold and she's the goddess.

Cruel Girlfriend Ashleigh - Fucked in Agony

VIDEO: Fucked in Agony

Don't let Ashliegh's soft spoken manner fool you loser! Ashliegh cooly and calmly explains what's in store for you tomorrow evening. She smiles as she tells you how you're going to be taken to a remote wooded area, tied to a tree, and then severely beaten by her and her violent, sadistic friends. Ashliegh leaves you in no doubt what to expect, explaining how her cruel girlfriends are going to literally leave you with broken bones, crying in agony as they enjoy every second of your suffering. After you've been beaten to within an inch of your life, Ashliegh tells you how she's going to hand you over to her 2 gay friends. She's going to watch and laugh as they fuck your defenseless body - nobody is going to hear you scream, nobody is going to come to your rescue!

Cruel Girlfriend Lolly Lopez - Spoilt Princess's Forced-Fag

VIDEO: Spoilt Princess's Forced-Fag

Your spoilt young girlfriend Lolly has taken you to a beauty spot to talk to you about her plans for you tonight. As a favour to one of her gay friends she's going to let him fuck you. She points out the secluded, wooded area you're going to be taken to for your humiliating ordeal. Lolly giggles as she explains how her gay friend will dry-fuck your sissy hole as you scream like a girl. Lolly teases you by telling how she'll be just a few steps away, getting some real-man action of her own. While you're getting filled by your new boyfriend's thick cock, your hot young girlfriend is going to be getting fucked by a stud. You're going to be totally humiliated tonight fag-boi.

Cruel Girlfriend Kimmy - Sissy Cuck Competition

VIDEO: Sissy Cuck Competition

Hot cheating girlfriend, Kimmy, is in need of a real man tonight. She's planning on finding a stud with a huge cock to cuckold you with at the fetish club. Usually Kimmy would leave you at home to prepare for your girlfriend and her man, ensuring the bed is made, there's plenty of condoms and lube etc, but tonight she's briniging you along to the club with her. The club has a competition for the best sissy cuck and Kimmy intends to win the cash prize so you're going to be dressed up in your pretty lingerie, cute pink socks and heels as she drags you around the club looking for her real man. You're going to be thoroughly humiliated as she makes you wiggle around in your heels, but you'll do exactly what you're told to. If you fail to win the prize, Kimmy is going to send the key to your chastity device to her girlfriend in Australia... where it'll stay for a VERY long time!

 

Cruel Girlfriend Elle - Garbaged and Locked

VIDEO: Garbaged and Locked

Drinking Princess Elle's drink was a stupid idea - you've really pissed her off now chastity boi! Elle always finds a cruel and humiliating punishment for your misbehaving and today is no exception. She makes up a stomach-churning cocktail and forces you to gulp it down in front of her. She laughs sadisticly as you gag on the disgusting drink but she has more to come for you yet. She empties her ashtray all over the floor, grinding the filthy butts into the ground with her leather boots. She commands you to clean the mess up with your mouth, to slurp up her discarded cigarette ends and ash as she stands over you. Then, for annoying her so much, she sentances you to an extended term in chastity, leaving you locked up for a VERY long time!

 

Cruel Girlfriend Nina Leigh - Pimp Princess Needs A Manicure

VIDEO: Pimp Princess Needs A Manicure

Stunning Pimp Princess Nina Leigh wants to raise some cash to keep her beautiful nails perfect. She wants to look her very best for her real man lovers and expects you to fund her luxury beauty treatments and her exotic holidays in the sun. She's hatched a plan to extort maximum cash from you whilst totally humiliating you at the same time. As much as Nina loves taking your cash, humiliating you gets her excited more than anything. She's whoring you out on the streets of your own neighbourhood. You're going to be dressed up like a total slut and forced to sell your sissy mouth and ass to complete strangers. Nina tells you that she doesn't want you coming home until you've been completely ruined by cock after cock. You're going to be coming home, night after night, with a stomach full of cum and handing all your cash to Nina so she can enjoy her luxury lifestyle with her real-man boyfriend!

 

Cruel Girlfriend Lolly Lopez - Party Girl's Puppy

VIDEO: Party Girl's Puppy

Every princess party girl needs her cute little accessory pet puppy and Lolly plans on turning you into just that. She's got a cute little collar for you, and some sissy clothing to add that extra little touch of humiliation. She's taking you to a party tonight and you're going to be paraded around as her obedient little puppy dog - how humiliating! Before you're allowed to go out Lolly wants to give you a taste of what happens to disobedient puppies. Lolly shows you why she's the bratty little mistress in your relationship and why you're the submissive little puppy boi.

Cruel Girlfriend Amber - Spit Breakfast for Cucky Bitch

VIDEO: Spit Breakfast for Cucky Bitch

Amber is such a spoilt little brat. She is so demanding in the morning and she accepts absolutely no excuses if you fail to please her. She's angry that her tea is too cold and you're going to pay the consequences! She takes you into the bathroom and begins brushing her teeth. You watch like a humble weakling as she spits her gross frothy toothpaste out and orders you to eat it up. She cruelly tells you this is all you're getting to eat today as she spits another mouthfull of waste paste out and you have no choice but to lick it all up. After your delicious meal for the day, Amber decides everybody should know what a pathetic cuckold you are, so she marks your body with your humiliating label. You're going to pay a humiliating price for Amber getting out of the wrong side of the bed this morning cucky!

 
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Cruel Girlfriends Emma & Amy - Dressed for Cucky Humiliation

VIDEO: Dressed for Cucky Humiliation

Cruel cheating girlfriend Emma has a date tonight - not with one guy but a whole group of hot, muscular, rugby guys. She's planning on cuckolding you with every single one of them and there's nothing you can do about it. Emma loves to rub your nose in her affairs with other men and delights in telling you exactly how she plans on treating each of the guys. But Emma doesn't leave your humiliation there, she has plans for you tonight too cucky. She's picked out a short little dress for you to wear tonight, as well as some sissy panties and a pair of heels. She wants you waiting at home for Emma to bring back the boys for an evening of shame for you. Emma is going to make you the rugby team's little fuck-doll for the night!

 

Cruel Girlfriend Becky - Chastity for Cheating

VIDEO: Chastity for Cheating

Just because your Cruel Girlfriend Becky cheats on you all the time doesn't mean you can do the same cucky! You've been out of your chastity device for one day and Becky walks in to the bedroom to find you've been partying with another woman. She is furious and decides you're never going to be allowed out of your chastity device ever again. She grabs your plastic cock tube and shows you where the key is going to be for the rest of your life. Your five minutes of drunken fun is going to cost you dearly cucky - no more sex EVER again!.. At least no more sex with women that is... Becky has one final humiliating revenge in store for you loser.

Cruel Girlfriend Natalia - Taunted Cuckold

VIDEO: Taunted Cuckold

Natalia takes so much delight in teasing you about her date with another man tonight. She looks absolutely stunning in her cut-off top and tight jeans, showing off her perfect figure - too bad it's not you who's going to get to enjoy it tonight. Because you forgot to pick her up, she caught a lift with a real man who's taking your place later. She's punishing you for being a forgetful loser by cheating on you with another man. There's nothing you can do as she mocks you for being the cuckolded wimp that you are. Say goodbye to your girlfriend cucky...

Cruel Girlfriend Rachel - Sissy's Double Date

VIDEO: Sissy's Double Date

Rachel and her stud are going out on another hot date tonight and she thought it would be a good idea if you came along to keep his best friend company. His best GAY friend that is! Rachel's picked out the perfect sissy bimbo outfit for you to wear for him... She wants you to make the right impression! Rachel has told your gay date all about you and has said you like to be treated like a cock-hungry little porn star. He's going to be pumping your mouth full of cock and blowing his sperm all over your sissy face. Rachel has even insisted that your gay date fills up a cup full of his creamy cum so you have a little souvenir to slurp up for after he's gone.

 

Cruel Girlfriend Chelsea - From Chastity to Castration

VIDEO: From Chastity to Castration

It's been a horrifying 4 years locked in chastity by your beautiful but cruel girlfriend Chelsea. She has starved you of any sexual release for year after year, feeding you nothing but frustration as she teased and denied you over and over again. You've hoped with all your heart that someday she'll let you out of your little cage - and that day has just arrived. She's going to put that long lost key into the lock and set you free... But Chelsea is going to take her evil plan to keep you a sexless little loser to a whole new level. She's arranged for her friends to give you a back-street castration to rob you of any chance of ever enjoying a night of pleasure with a woman ever again. They're taking your cock and balls and turning you into a pathetic sissy girl for the rest of your life. Chelsea's heartless desire to destroy your manhood doesn't end at having your worthless cock removed though sissy. Tonight you're also going to feel what it's like to be used like a real girl.

Cruel Girlfriend Jen - Tied & Abandoned

VIDEO: Tied & Abandoned

Cruel girlfriend Jen has brought you to the graveyard to explain how she plans on taking your humiliation to a whole new level tonight. Your heartless girlfriend knows that this quiet location is frequented by gays looking for anonymous sex with strangers. She thinks it would be amusing to leave you tied up, naked and helpless, for all the local fags to abuse. She gets an evil kick out of your fear and desperation. She shows no mercy as she forces you to strip and prepare to be strapped to a cross ready for your evening of forced-fag action.

 

 

Cruel Girlfriends Emma & Amy - Sissy Panties JOI

VIDEO: Sissy Panties JOI

Hot cheating girlfriend Emma has some good news and some bad news for you today cucky. The good news is your heartless princess has decided to let you out of the tight plastic chastity device she's had you locked up in for so long. The bad news is she's invited her cute girlfriend Amy over to help administer a humili-gasm. The 2 cruel girls laugh and giggle at you as they force you to jerk your pathetic loser-stick into a pair of their girlie lace panties. There's nowhere to hide as they totally humiliate you for having to squirt your sissy-goo in front of 2 mean girls. Then when you've been allowed to spit out your little emasculation puddle deep into the soft panties, the 2 girls have one final humiliation for you to swallow!

 

Cruel Girlfriend Lolly Lopez - Locked For Lapdance

VIDEO: Locked For Lapdance

Your hot young girlfriend Lolly has found out about your little encounter at the lapdancing club. She can't believe you'd sneak off to get a sexy dance from another girl when you've got such a stunning girl at home. Your total disrespect is going to be severely punished. Lolly decides that since you cannot be trusted, she's going to lock your cock away in a chastity device. She cruelly explains how you're never going to cum again, never going to be able to touch yourself without begging her for permission. Lolly intends to lock you away for a VERY long time loser so you'd better get used to having to beg a pretty girl to cum. Lolly has a humiliating plan for your first night in the device too. She's taking you back to the lapdancing club so she can show all the hot dancers what you're being forced to wear for the rest of your life. They're all going to find it hilarious loser boi - all the girls in the club are going to be laughing at you in your chastity device.

 

 

Cruel Girlfriend Catherine - I'm telling everyone...

VIDEO: I'm telling everyone...

She's dumping you loser! Your hot young girlfriend Catherine has seen you for the pathetic little weakling you really are and has decided to find herself a real man. Before she throws you out, she's going to play one final cruel game. She snatches your phone from you as you're cuffed to a chair and starts calling all the female names she can find in your contacts. She starts will Ania, the cute girl from the office. She tells Ania all about how she dresses you up in girlie lingerie and sends you in to work. You sit there helpless as she laughs and jokes about the style and color lingerie she makes you wear. You're totally mortified as she humiliates you with the office hottie but it's going to be nothing compared to when you have to face her and the other office girls... Next she calls Becky, the hot model you drool over at the gym. She tells her all about how she watched you suck cock and get fucked by gay men, and how you're face is sprayed with their thick cum. OMG sissy, you're going to be the laughing stock at the gym from now on... Who's next to call?..

 

Cruel Girlfriend Jamie - Cucky's Cut-Price Castration

VIDEO: Cucky's Cut-Price Castration

Cheating girlfriend Jamie sees no reason for you to keep your cock and balls any longer. You NEVER get to have sex with her anymore and no other girls are ever going to look at you so what's the point in having them any more? Jamie has arranged for the local vet to give you a cut-price castration - removing your last slither of masculinity forever. You're going to be taken into the kitchen and given an agonising gelding while Jamie and her girlfriends party in the next room. Once you're pathetic sissy-stick and tiny blue balls have been ripped from your body, you'll be a permanent little sissy girl for the rest of your life!

 

Cruel Girlfriend Lolly Lopez - Girlfriends Girlify You

VIDEO: Girlfriends Girlify You

Lolly and her girlfriend are getting ready for a night out with some real men but take a break to abuse and humiliate you. Lolly decides that you can spend the night dressed like a sissy girlie to remind you why you're not man enough to take these hot young party girls to the clubs. She picks out pretty pink lingerie to force you into and makes you pout as she applies a nice thick layer of pink lipstick to your girlie lips. The girls both find your humiliation hilarious and mock you for being such a pathetic little sissy. Next the girls force you onto your back and reveal their next terrifying torture - a waxing kit to give you girlie- soft skin. They help each other tear the hair from your body - enjoying every second of the agony they're inflicting on you. Lolly forces the disgusting hairy wax strips into your mouth before your next humiliating ordeal begins. The girls decide to play a humiliating game with you before they head off for their night of fun.

 

Cruel Girlfriend Amy - VIDEO: Cum Sandwich

VIDEO: Cum Sandwich

Your hot Latino girlfriend has had you locked in chastity for a VERY long time and you've had no choice but to be the perfect little cuckold boyfriend for her. You've bought her presents, paid for her hot dates, and financed her luxury lifestyle just like a good little loser. Amy thinks it's time you deserve a special treat for being so well behaved so she's letting you out of your cock-cage for a few precious minutes before she heads out to meet her real-man. Of course Amy has no intention of letting you enjoy your first orgasm in months without having to suffer a humiliating experience at the same time. If you want to cum, just like a real man can, you're going to do it into your food! Amy is going to help you jerk your sissy loser-goo into your lunch, and watch as you eat it all up. You can get dressed in your little sissy outfit with the taste of your own cum in your throat as Amy leaves you and goes to meet her real man.

 

Cruel Girlfriend Lara - Sissy Strap-on Tester

VIDEO: Sissy Strap-on Tester

Sat in your stunning girlfriends dirty bath water, helping her get ready for the sex-toy party she's throwing tonight is as good as it gets for a pathetic weakling like you. Lara tells you about the party she's having later, how all her cute girlfriends are going to be there, and how they're going to need a model to demonstrate the various toys. She watches you squirm as she explains how it's going to be you the girls will be experimenting on this evening. It's going to be you at the business end of the strap-ons and anal abusing implements and it's going to be you that everyone will be laughing at as you struggle to accept each and every one of these toys in your little sissy toy-box.

 

Cruel Girlfriend Nina Leigh - Princess Nina's Sunbathing Servant

VIDEO: Princess Nina's Sunbathing Servant

Nina Leigh has a hot date with the one of the local guys that works at the stables tonight. She wants to look her best for her man tonight so she's relaxing in the sun building on her all-over tan. Being the unthreatening beta male that you are, Nina has no problem forcing you to help her with her lotion as she tells you about her date tonight. You gently massage the cream into her beautiful soft skin as she gives you a list of chores to complete while she spends all your hard earned cash on her date with a real man. No doubt they'll both be laughing at you as they head off for their night of luxury as you scrub the floors on your hands an knees for them.

Cruel Girlfriend Jamie - Forced-Fag Nightmare

VIDEO: Forced-Fag Nightmare

Jamie has taken you to a secluded spot in the park and cuffed you to a tree. You realise very quickly that you're in an frightening amount of trouble. Jamie delights in your fear as she explains the terrifying nightmare you're to expect tonight.You've been taken to a local gay sex den and you're going to be left helplessly shackled to the tree for an endless queue of fags to abuse you for hour after agonising hour. Jamie tells you that while you're being passed from gay to gay, sucking on their balls and getting ruined by their fat cocks, she's going to be spending your cash with her real man lover. You get to spend a humiliating night in the gay sex den getting filled with fag cum, while your heartless girlfriend parties the night away, having fun at your expense. Have a nice night cucky!

 

Cruel Girlfriend Ashleigh - Cuckold Cash Quest

VIDEO: Cuckold Cash Quest

Your cheating girlfriend Ashleigh is getting ready to meet her real-man. Dressing herself in her tiny miniskirt, and a slutty top. As she rolls up her black fishnet stockings she tells you that you're going to spend the night under the bed, locked in chastity, as she fucks her real man inches above you. You're going to learn exactly how a girl like Ashleigh should be treated in the bedroom. But before she brings her stud back, she's going to take him to an expensive restaurant and guess who's paying cucky? Ashleigh wants you to go and get some cash to fund her hot date, so she's sending you out to the ATM... And she has the perfect little sissy outfit set aside to make you walk to the shops in. Not only are you going to be humiliated in the bedroom tonight cucky, but you're going to be humiliated in public too!

 

 

 

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