The CruelGirlfriend Sissy Prosti-whoreing Ring has been successfully whoring out submissives for years now. All over the world we have our sissies advertising their services on Craigslist, in public restrooms, and at adult bookstores. Most of our sissies whore themselves voluntarily simply because they understand their purpose in life, others are being out to prevent being exposed by us as victims of our zero-tolerance blackmail program. We evaluate each sissy and decide upon what services they will offer and what rates they will charge. We help with advertising and in some circumstances we even decide exactly where the sissy will whore herself. We've made a very successful business sissy wimps like you to suck cock, suffer extreme humiliation and abandon your sexuality. There is a great deal of profit to be made in every sissy! YOU are going to contribute to that profit sissy! You are going to be out for our financial gain. We're going to decide what services you'll sell to the horny perverts who get their kicks from fucking and humiliating sissy-dress-up sluts like you. We're going to decide what you charge, and we will set you a minimum amount of to earn for us every day. We'll direct an endless stream of guys to your sissy holes - all desperate to treat you like their very own fuck-doll. When you're on your knees with a stranger’s cock in your mouth think of how much fun I'm having spending the money you're earning. While he's slapping your face and calling you humiliating names - think of us sipping and laughing at the thought of you getting degraded for cash.

Also available to download in full 1920 x 1080 HD MP4 Format

The CruelGirlfriend Sissy Prosti-whoreing Ring has been successfully whoring out submissives for years now. All over the world we have our sissies advertising their services on Craigslist, in public restrooms, and at adult bookstores. Most of our sissies whore themselves voluntarily simply because they understand their purpose in life, others are being out to prevent being exposed by us as victims of our zero-tolerance blackmail program. We evaluate each sissy and decide upon what services they will offer and what rates they will charge. We help with advertising and in some circumstances we even decide exactly where the sissy will whore herself. We've made a very successful business sissy wimps like you to suck cock, suffer extreme humiliation and abandon your sexuality. There is a great deal of profit to be made in every sissy! YOU are going to contribute to that profit sissy! You are going to be out for our financial gain. We're going to decide what services you'll sell to the horny perverts who get their kicks from fucking and humiliating sissy-dress-up sluts like you. We're going to decide what you charge, and we will set you a minimum amount of to earn for us every day. We'll direct an endless stream of guys to your sissy holes - all desperate to treat you like their very own fuck-doll. When you're on your knees with a stranger’s cock in your mouth think of how much fun I'm having spending the money you're earning. While he's slapping your face and calling you humiliating names - think of us sipping and laughing at the thought of you getting degraded for cash.

Also available to download in full 1920 x 1080 HD WMV Format

THERE IS AN ALTERNATIVE ENDING FOR THIS CLIP - THIS CLIP HAS ENDING 2

You know the rules sissy, beta pussies like you don't get to jerk off like a normal guy - you're only allowed to cum from being penetrated in your boy-pussy. No touching for you sissy - no way! Not that you should even be able to touch your fairy-stick anyway - it should be safely caged away with the key dangling between my perfect cleavage. If you want to cum you're going to fuck your beta-load out by pounding your own ass with a HUGE dildo. You're going to ruin your girly little ass just like one of my Alpha studs would if I ever let one of them get their hands on you! Pick your biggest, thickest dildo - the one you just can't quite take. This is the cock we're going to use to stretch you out and ruin you with. Get yourself in the humiliating legs-over-your-head position so your cock is aiming right at your faggot face and then start pumping your ass full of monster-cock! Moan like a girl if you're struggling with the pain, whimper and bite your lip - whatever you need to do to get through your emasculating ass-fucking - just DO NOT stop! My real men wouldn't stop - in fact if they noticed how much it was hurting you and how ashamed of yourself you were - they'd fuck you even harder! Ruin your ass sissy - fuck yourself so hard and so deep your poor boy-pussy will never be the same. Keep going until you're ready to blow your load then BEG me to allow you a ruined orgasm. As you're pounding yourself full of cock say, in your girliest voice 'Please Miss Jyssica - may I have a ruined orgasm all over my sissy face?' and maybe I'll allow you to cum like a girl for me.

Also available to download in full 1920 x 1080 HD MP4 Format

THERE IS AN ALTERNATIVE ENDING FOR THIS CLIP - THIS CLIP HAS ENDING 2

You know the rules sissy, beta pussies like you don't get to jerk off like a normal guy - you're only allowed to cum from being penetrated in your boy-pussy. No touching for you sissy - no way! Not that you should even be able to touch your fairy-stick anyway - it should be safely caged away with the key dangling between my perfect cleavage. If you want to cum you're going to fuck your beta-load out by pounding your own ass with a HUGE dildo. You're going to ruin your girly little ass just like one of my Alpha studs would if I ever let one of them get their hands on you! Pick your biggest, thickest dildo - the one you just can't quite take. This is the cock we're going to use to stretch you out and ruin you with. Get yourself in the humiliating legs-over-your-head position so your cock is aiming right at your faggot face and then start pumping your ass full of monster-cock! Moan like a girl if you're struggling with the pain, whimper and bite your lip - whatever you need to do to get through your emasculating ass-fucking - just DO NOT stop! My real men wouldn't stop - in fact if they noticed how much it was hurting you and how ashamed of yourself you were - they'd fuck you even harder! Ruin your ass sissy - fuck yourself so hard and so deep your poor boy-pussy will never be the same. Keep going until you're ready to blow your load then BEG me to allow you a ruined orgasm. As you're pounding yourself full of cock say, in your girliest voice 'Please Miss Jyssica - may I have a ruined orgasm all over my sissy face?' and maybe I'll allow you to cum like a girl for me.

Also available to download in full 1920 x 1080 HD WMV Format

THERE IS AN ALTERNATIVE ENDING FOR THIS CLIP - THIS CLIP HAS ENDING 1

You know the rules sissy, beta pussies like you don't get to jerk off like a normal guy - you're only allowed to cum from being penetrated in your boy-pussy. No touching for you sissy - no way! Not that you should even be able to touch your fairy-stick anyway - it should be safely caged away with the key dangling between my perfect cleavage. If you want to cum you're going to fuck your beta-load out by pounding your own ass with a HUGE dildo. You're going to ruin your girly little ass just like one of my Alpha studs would if I ever let one of them get their hands on you! Pick your biggest, thickest dildo - the one you just can't quite take. This is the cock we're going to use to stretch you out and ruin you with. Get yourself in the humiliating legs-over-your-head position so your cock is aiming right at your faggot face and then start pumping your ass full of monster-cock! Moan like a girl if you're struggling with the pain, whimper and bite your lip - whatever you need to do to get through your emasculating ass-fucking - just DO NOT stop! My real men wouldn't stop - in fact if they noticed how much it was hurting you and how ashamed of yourself you were - they'd fuck you even harder! Ruin your ass sissy - fuck yourself so hard and so deep your poor boy-pussy will never be the same. Keep going until you're ready to blow your load then BEG me to allow you a ruined orgasm. As you're pounding yourself full of cock say, in your girliest voice 'Please Miss Jyssica - may I have a ruined orgasm all over my sissy face?' and maybe I'll allow you to cum like a girl for me.

Also available to download in full 1920 x 1080 HD MP4 Format

THERE IS AN ALTERNATIVE ENDING FOR THIS CLIP - THIS CLIP HAS ENDING 1

You know the rules sissy, beta pussies like you don't get to jerk off like a normal guy - you're only allowed to cum from being penetrated in your boy-pussy. No touching for you sissy - no way! Not that you should even be able to touch your fairy-stick anyway - it should be safely caged away with the key dangling between my perfect cleavage. If you want to cum you're going to fuck your beta-load out by pounding your own ass with a HUGE dildo. You're going to ruin your girly little ass just like one of my Alpha studs would if I ever let one of them get their hands on you! Pick your biggest, thickest dildo - the one you just can't quite take. This is the cock we're going to use to stretch you out and ruin you with. Get yourself in the humiliating legs-over-your-head position so your cock is aiming right at your faggot face and then start pumping your ass full of monster-cock! Moan like a girl if you're struggling with the pain, whimper and bite your lip - whatever you need to do to get through your emasculating ass-fucking - just DO NOT stop! My real men wouldn't stop - in fact if they noticed how much it was hurting you and how ashamed of yourself you were - they'd fuck you even harder! Ruin your ass sissy - fuck yourself so hard and so deep your poor boy-pussy will never be the same. Keep going until you're ready to blow your load then BEG me to allow you a ruined orgasm. As you're pounding yourself full of cock say, in your girliest voice 'Please Miss Jyssica - may I have a ruined orgasm all over my sissy face?' and maybe I'll allow you to cum like a girl for me.

Also available to download in full 1920 x 1080 HD WMV Format

Aw poor sissy doesn't want to be a girl haha! Well that's too fucking bad sissy. You're going to be my pretty feminized doll and that's the end of it. I've got rid of all of your boy clothes and have bought you a whole wardrobe full of frilly girlie things for you to wear from now on. All of your shoes have been replaced with high heel pumps and I've filled your drawers with all the makeup a girl could ever want. It doesn't actually matter to me that you don't WANT to be a girl - in fact I prefer to weaklings like you anyway. It's much more fun to strip a wimp of his masculinity while he begs me not to turn him into a girl. The thing is, it's not just cute new clothes, sexy shoes and pretty makeup you'll be getting sissy. At the end of the week you have an appointment at the feminization theatre who will be performing some extreme surgeries on you to make sure you're a girl FOREVER. You'll get big plastic tits and lips, a tiny waist and a more girlish profile to your face. You're going to be turned into a girl - I guess if that's going to be against your will then that's just the way it's got to be. No amount of struggling, begging or crying your sissy heart out is going to get you out of this - you're worth much more to us as a girl than you are as a boy. As soon as your surgery has healed you'll be put through intense feminization training and then put to work as the newest fuckdoll on the streets. You're going to be involuntarily feminized and then involuntarily whored out to men for my financial gain bitch.

Also available to download in full 1920 x 1080 HD MP4 Format

OTHER CLIPS FROM CRUEL GIRLFRIEND:

Cock Teased

Ass-Fucked Until You Cum

Chained In The Mens Room

Oops I Guess You're A Faggot Now

Would You Suck Cock For Me

Aw poor sissy doesn't want to be a girl haha! Well that's too fucking bad sissy. You're going to be my pretty feminized doll and that's the end of it. I've got rid of all of your boy clothes and have bought you a whole wardrobe full of frilly girlie things for you to wear from now on. All of your shoes have been replaced with high heel pumps and I've filled your drawers with all the makeup a girl could ever want. It doesn't actually matter to me that you don't WANT to be a girl - in fact I prefer to weaklings like you anyway. It's much more fun to strip a wimp of his masculinity while he begs me not to turn him into a girl. The thing is, it's not just cute new clothes, sexy shoes and pretty makeup you'll be getting sissy. At the end of the week you have an appointment at the feminization theatre who will be performing some extreme surgeries on you to make sure you're a girl FOREVER. You'll get big plastic tits and lips, a tiny waist and a more girlish profile to your face. You're going to be turned into a girl - I guess if that's going to be against your will then that's just the way it's got to be. No amount of struggling, begging or crying your sissy heart out is going to get you out of this - you're worth much more to us as a girl than you are as a boy. As soon as your surgery has healed you'll be put through intense feminization training and then put to work as the newest fuckdoll on the streets. You're going to be involuntarily feminized and then involuntarily whored out to men for my financial gain bitch.

Also available to download in full 1920 x 1080 HD WMV Format

OTHER CLIPS FROM CRUEL GIRLFRIEND:

Cock Teased

Ass-Fucked Until You Cum

Chained In The Mens Room

Oops I Guess You're A Faggot Now

Would You Suck Cock For Me

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!

Also available to download in full 1920 x 1080 HD MP4 Format

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!

Also available to download in full 1920 x 1080 HD WMV Format

Guess what cuckold - another real man is taking your girlfriend out on a date tonight! You get the humiliation of watching me spend hours making myself looking perfect for him, helping me choose a slutty dress to wear for him, help me slip into my favourite lingerie set and then driving me to whatever classy restaurant or bar he gets to take me to tonight. The usual cuckold experience you've had to get used to right cucky? Tonight is gonna be a little different though because the guy I'm dating tonight knows I have a beta wimp boyfriend and he's totally up for helping me humiliate the fuck out of you. So while we're out on our date tonight you should expect to receive taunting video messages from BOTH of us! Selfies of him with his hands all over your girlfriend, videos of me putting my hand down his pants to sample his huge alpha cock. Voice messages from HIM telling you exactly what he plans to do to your girl when he gets her back to your bedroom. It's so much fun teasing you with all the details of my cheating nights out with other men, but it's gonna be so much better when your rival is actually putting you in your place right with me! And it's gonna be even better when we get back home and humiliate you for real! He wants you licking his boots while he's fucking me and I love the idea! My weakling boyfriend kneeling at the foot of the bed with his tongue licking the dirt from the boots of the guy who's fucking your little princess. How fucking pathetic! I'm gonna love watching him totally fucking humiliate you!

Also available to download in full 1920 x 1080 HD MP4 Format

Guess what cuckold - another real man is taking your girlfriend out on a date tonight! You get the humiliation of watching me spend hours making myself looking perfect for him, helping me choose a slutty dress to wear for him, help me slip into my favourite lingerie set and then driving me to whatever classy restaurant or bar he gets to take me to tonight. The usual cuckold experience you've had to get used to right cucky? Tonight is gonna be a little different though because the guy I'm dating tonight knows I have a beta wimp boyfriend and he's totally up for helping me humiliate the fuck out of you. So while we're out on our date tonight you should expect to receive taunting video messages from BOTH of us! Selfies of him with his hands all over your girlfriend, videos of me putting my hand down his pants to sample his huge alpha cock. Voice messages from HIM telling you exactly what he plans to do to your girl when he gets her back to your bedroom. It's so much fun teasing you with all the details of my cheating nights out with other men, but it's gonna be so much better when your rival is actually putting you in your place right with me! And it's gonna be even better when we get back home and humiliate you for real! He wants you licking his boots while he's fucking me and I love the idea! My weakling boyfriend kneeling at the foot of the bed with his tongue licking the dirt from the boots of the guy who's fucking your little princess. How fucking pathetic! I'm gonna love watching him totally fucking humiliate you!

Also available to download in full 1920 x 1080 HD WMV Format