Showing 1–24 of 35 results


Destroy your Life!


Alright bitch face. It’s time for you to get your fucking life destroyed by a young, hot and ruthless Princess! You are going to follow the series of cruel and humiliating instructions I have laid out for you in this assignment and once you are done, I guarantee you will lose your friends, family, job and maybe even your entire family!

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Homewrecking Fetish

Relationship Ruin


Princess Shimmy is going to ruin the relationship you have with your wife or girlfriend… that’s right bitch! Not only am I going to take your money I’m going to make your partner fucking leave you too!! You will love the diabolical plan I have to leave you broke & broken up with your spouse! LOL.


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Gay Porn Drinking Game


Let’s have some fun tonight by getting you super fucked up while watching gay porn. You’re going to need lots of beer, hard liquor and the stomach to take the alcoholic punishment I’m about to inflict on you! Come get intoxicated, the evil Princess Shimmy way! Are you up for the challenge?

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NiteFlirt Findom

Truth or Dare Game


Let’s play a risky humiliation game that you’ll never forget. Inside this PTV are 10 Truth or Dare tasks that will leave you shocked, hard and questioning your own dignity! If you’re not into extreme humiliation and/or possibly answering super personal questions, run the other way! Come play My super degrading and potentially exposing truth or dare game!

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Small Penis Protection Program


Your secret is out and everyone knows that you have a small penis. Your fail cock is so embarrassing that it should be put into the witness protection program to never be seen again! Lucky for you, being the genius that I am I have My very own version called the small penis protection program. You will disguise your cock and go deep undercover so your cock won’t even be recognized anymore.

We both know that thing between your legs isn’t a dick. It’s a focal point of mockery and laughter so you might as well have some fun by joining Princess Shimmy’s Small Penis Protection Program!

*Includes two example pics of other slaves who have completed this assignment*

Stealthy Public Jack Off Missions


I list 5 public places where you must jack off AND bust your load within a week. You’ll be like the Jason Borne or James Bond of jacking off! You must stealthily complete all 5 jack off missions within 7 days or you will FAIL and be punished!

WARNING: Not only is this slave assignment incredibly humiliating, it’s also very risky and dangerous. Play at your own risk!

Small Penis Confessions


It’s time for you little dick losers make some confessions! Confess your shame. Confess your most humiliating moments so I can have a laugh at your expense. In this slave writing task I have 5 small penis humiliation questions that will delve into mind and uncover your insecurities and inadequacies.

I allow you to send the answers back to Me so I can read it and LOL right in your face. Just a warning though, if I find your confessions humiliating enough, I *might* just post it publicly! Come answer these small penis slave questions and reveal the truth to Princess about that abomination between your legs!

Fuck your Wife Fee


As a strict Femdom authoritarian, I rule My slaves with an iron fist and am very strict about sexual relations and behaviours *especially* if you’re locked in chastity. Slaves of Princess Shimmy must not only ask permission to have sex with their wives but must pay for it too!
*Comes with one worship pic to help you get hard enough to do it. I know some of you might need it! LOL*

10 Odd Insertions Challenge


Here’s 10 odd objects that I instruct you to stick where the sun doesn’t shine. Get ready for some seriously degrading ass fuck instructions with various objects that can be found around the house or the grocery store. You’ll be so humiliated you won’t even be able to look at some of these every day objects the same again! Are you ready to defile yourself and give that butthole a humiliating workout for Princess? Can you handle all 10 objects? Come complete My odd insertions challenge and find out now!

7 Deadly Sins: 1 Week of SIN


7 Deadly sins… one week of sin. One week of pure Femdom debauchery where you will commit every sin imaginable in the name of freedom and liberation! Lust, gluttony, greed, sloth, wrath and more.
You will throw your human decency out the door and succumb to life’s forbidden pleasures. Can you handle it? Your life will never be the same again once you complete Princess Shimmy’s 1 week of sin assignment.

Plugged and Locked


Get locked and plugged for Princess! In this humiliating assignment you will be made to wear a buttplug and chastity device for the next 5 days while you go about your business in public. You will be so humiliated and embarrassed waddling around town thinking everyone knows you have something shoved up your fuck donut! You’ll be in full on bitch mode as you are given 5 different humiliation destinations you will take a trip to while locked and plugged for Princess!

Truth or Dare Game


Let’s play a risky humiliation game that you’ll never forget.  Inside this are 10 Truth or Dare tasks that will leave you shocked, hard and questioning your own dignity!

If you’re not into extreme humiliation and/or possibly answering super personal questions, run the other way!  Come play My super degrading and potentially exposing truth or dare game!

Privacy Invasion Questions


Are you ready to have your privacy and personal life completely invaded? In this I’ve included 35 embarrassing, humiliating and personal questions to make you squirm in your seat as you answer them!

You will feel so mentally violated as you are made to confess things you wouldn’t want anyone in the world to know! Come spill the beans and subject yourself to My style of interrogation.


Do You Have an Ugly Cock Quiz

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So bitch, I bet you’ve always wondered what a hot girl such as Myself would think about your cock.  Perhaps you’re worried you have an ugly penis and want someone like Me to verify that suspicion for you. You’re obviously too shy to ask a girl in real life and probably even more afraid to show it to one! Luckily for you I have this handy quiz that will let you know precisely where you stand in terms of dick… to ick!! Just answer the series of questions in this quiz to find out if you have an ugly cock!

Broken Memories Homewrecking


It’s time for you to face the facts and realize that your relationship situation is interfering with you serving Me.  This, My dear little bitch, is totally unacceptable!  Princess needs to come first before everything so we’re going to make sure we put the nail in the coffin with your relationship. Together we are going to take your life and quite literally RIP IT TO SHREDS so that all you’re left with is broken memories and a broken home.

Small Penis Humiliation Quiz


Are you feeling insecure about your “junk?” Ever wonder how you measure up against other males? We all know you can measure your dick to find out if it is big or small, but what you may not know is that there are other determining factors that can dictate whether you are packing or lacking!  Let’s go beyond actual penis size and I’ll tell you exactly how you measure up!

Just know that when you find out the truth, there will be a punishment suited for your situation, tailored just for you and your dick!

Sissy Exposure Dice Game


You fantasize about dressing up in your girlie outfit, sucking dick and taking it up your slutty ass! Awww, come on. Don’t be shy bitch boy, your secrets are safe with me… for now!
Well, guess what? I’m going to help you act out on those fantasies with this dice game. What embarrassing poses and actions will Princess have you photograph yourself doing? Will your pictures impress Me enough for Me to post online, possibly exposing you for the world to see?
Come find out now, slave. Your fate will be sealed with the roll of the dice!

P.S. Don’t worry if you don’t have any dice on hand. I link you to a website when you can roll one online!

Cum Recycling Program


Since being “green” and environmentally friendly is all the rage I have come up with a way for slaves to impress Me with their Eco-consciousness! Sing hoorah for Me now losers and partake in My recycling program! Will it be humiliating? Yes.  Will it be beneficial to the world? Perhaps!  We won’t know until you try! Become a part of Princess Shimmy’s Cum Recycling Program… for environmentally conscious slaves today!

Self Hating Cock


I command you to look in the mirror as I humiliate you about your disgusting “cock.”  You are given jerk off instructions while being reminded about what an inferior, sub human, piece of trash you are! But oh no… it doesn’t end there! You are made to show your hatred towards your cock and prove to Me that you hate it even more than I do!

Chastity Hell Week Part 3


This is the final installment of your week in chastity hell!  You already got this far… so you might as well go completely over the edge!  You will be taking part in “Fellatio Friday,” “Sadist Saturday” and “Sacrifice Sunday.”  Don’t even think for a second that this will be easy, because it won’t! You will be made to brush up on your BJ skills, go through torturous CBT and completely edge your cock in the very end. Will you be allowed release?  Will you ever be allowed to cum again?  Let’s find out now!

Homemade Pocket Pussy


Hey loser! It’s time to face the facts. Your loser dick is never going to please a real woman, so why would you ever need to see or feel a real pussy ever again?
You shouldn’t be wasting MY money on expensive sex toys, so I’m going to give you step by step instructions on how to make two different types of your very own pocket pussy!
OMG! You are soo lucky for this! Be prepared to meet your new “girlfriend!”

Pillow Humper


Haha LOSER! You and I both know you couldn’t get laid even if you tried. But don’t worry, I have a solution for this little problem of yours.  Today we are going to turn that pillow of yours into your new girlfriend!
You’re going to follow My humiliating pillow humping instructions while staring at 3 of the worship pics I have included in this.
Ready… Set… Hump your pillow!

5 Steps to Splitsville


You and I both know that your wife or girlfriend is getting in between your obligations towards serving Me! So I have concocted 5 diabolical steps that you are going to follow to the letter to get rid of the extra baggage! Before you know it, there will be no wife/gf to take up your time so you can begin in your never ending servitude to Me!
Are you ready to ruin your relationship, destroy your sex life and lose everything so you can start your new life as My new bitch?

I Double Dare You Roulette


Let’s play a game My little puppets… a very dangerous one. Let’s do a little humiliation and mix it up with some exposure roulette, shall we? This contains a series of dares that if you perform can leave your reputation totally annihilated or maybe you will be lucky and get away with it! So let’s play bitch, I double dare you!