Slave Sissywannabe38
Anal Play
Anal Play
Nipple Play
Nipple Play
Sissy
Sissy
Discipline
Discipline
Pain & CBT
Pain & CBT
Toilet Play
Toilet Play
Bondage
Bondage
Pet Play
Pet Play
Humiliation
Humiliation
Foot Fetish
Foot Fetish
Orgasm Control
Orgasm Control
Maid
Maid
Little sissy in the making, I will get dressed up accordingly and will enjoy wearing make up, wigs and false lashes. I will clean my Goddess with my tongue, collect her spit and will also relieve her #1 emergency.
I will be my Goddess’s furniture, she can sit or stand on me. I will also take her critics and will serve her friends just the same if that is her wish. I will follow orders and serve.
I would love me a good pegging. I also love a good, hot and messy shower, +1 if it’s in a public restroom. I will stay under the table until a finger snap tells me to honor or relieve a guest. I will stay silent when someone sits in my face, I will clean feet with my tongue will remain silent even if being ignored.
I will be my Goddess’s furniture, she can sit or stand on me. I will also take her critics and will serve her friends just the same if that is her wish. I will follow orders and serve.
I would love me a good pegging. I also love a good, hot and messy shower, +1 if it’s in a public restroom. I will stay under the table until a finger snap tells me to honor or relieve a guest. I will stay silent when someone sits in my face, I will clean feet with my tongue will remain silent even if being ignored.
I’m feeling dreamy tonight… I’m dreaming of a real feminine and strong Goddess living close enough to me that I could go shopping with, go out in the street dressed and dolled up as my true self, having girls nights out where she and her friends can make fun of me for trying to be one of them.
Dreaming of a lady who’s afraid of nothing to humiliate my person, using me as her personal #1 toilet and sharing my mouth with her girlfriends, spitting at me and letting me clean her whenever and wherever she feels the need for me to help her get refreshed.
Dreaming of becoming the dirty little sissy cumslut I was always meant to be… taking strapon and cocks alike, all for the glory, fame and entertainment of my mistress and her guests.
I will be good. I will obey. Please put me to good use. Feel free to abuse me and humiliate me ❤️
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Today I went shopping, shopping as a regular man but buying feminine items like dresses, lingerie, makeup and sextoys definitely makes me feel like a little slut… I wanted to scream out loud, reveal my true nature to all those beautiful ladies ringing me up and helping me make my choices… I wanted them to know I was buying these for myself, because I’m a dirty little sissy that likes to be humiliated and the idea of them knowing made me feel some type of way, like they should know and I should accept my true nature… I need advice for my next shopping session… should be more honest about it or just leave those people alone?
3
| Date | Ownership change |
| 2025-10-20 18:07:47 | Ends its services to Mistress Anna99 |
| 2025-10-08 06:51:59 | Starts serving Mistress Anna99 |
The items shown below were agreed to by the slave when doing its Skills Assessment.
(Only the low level skills and below are displayed, you need to be a registered Dom to see all the skills.)
Anal Play
You will be blindfolded and bound while I tease you with my strap-on, making you beg for it
I want you to insert a butt plug, wear a short skirt, and then bend over in front of Me to reveal your sissy ass. You will remain in this position until I tell you to stand.
I want you to moan loudly while I fuck your ass.
As punishment you will bounce up and down on this dildo while singing Britney Spears, "Oops I did it again" at the top of your lungs until you are permitted to stop
I want you to edge yourself with a prostate massager while reading out loud humiliating affirmations I prepared for you.
I will but put a vibrating plug up your ass and tape your cheeks together. Now i will tie you up an leave you lying on the floor.
I will put a small remote-controlled anal vibrator in you and force you to complete chores with it randomly buzzing you. If you drop anything, you will be punished immediately.
Wear this butt plug under your pants, we are going out shopping.
You will get a replica of your pathetic cock made. I will fit it to my belt, then you can get ready for some pegging!
You will be tied with your legs spread and your ass exposed. I will take a cucumber and insert it into your asshole, making you hold it in place for several minutes.
Sissy
I want you to insert a butt plug, wear a short skirt, and then bend over in front of Me to reveal your sissy ass. You will remain in this position until I tell you to stand.
I want you to masturbate wearing panties. Cum into the panties and lick them clean
You will wear lace gloves and delicately serve Me, showing how refined a sissy you’ve become.
I will make you practice walking in heels for me and trip you with my cane every time you slightly wobble.
I want to test my new make-up on you first before I'll try it on myself.
I will have you order a pizza for delivery and accept the delivery in your cutest sissy outfit
I will make you wear girly perfume and practice feminine speech patterns.
I want you to go shopping with me and try on the clothes I pick out for you.
I want you to sit in this chair while I tie your arms and feet down, and I will give you a beautiful makeover. You will then put your cock in a chastity cage and we will dress you up in this finest lingerie.
I will make you get a manicure and pedicure, and keep your nails painted at all times.
I will watch you mow my lawn in a mini skirt and sports bra
Discipline
I will make you clean my dirty underwear by hand every night before you are allowed to go to sleep.
You will practice my hypnosis routine every day. Melt your mind, pour it in a bowl, and give it to Me. You will become a perfect toy for Me to destroy over and over again.
Shave off all your hair. You will be spanked for every follicle I find.
Whenever you give or offer Me something, you will always do it with both of your hands instead of just one
I am hosting a party tonight. You will kneel at the entry. Your hands will be bound behind you and you will be blindfolded. Each guest will introduce themselves to you when they arrive. You must memorize the sound of their voice. Through the evening they will come say hello to you. If you reply to them with the wrong name you must satisfy them orally.
If you cum without my permission I will make you swallow it.
You are not allowed to speak for 7 days
You will be tied up with a piece of candy forced into your mouth. You will hold it there until I decide you are worthy of consuming it. Once permitted, you will eat the candy slowly, savoring the taste and thanking Me.
I want you to take an online course on how to properly give Me a manicure
Every evening you will say good night to my feet by giving a kiss to each toe, the sole and the top of each of my feet
You are not allowed to talk to any women without My permission.
Stand facing the wall, arms and legs outstretched and hold a coin with your nose to the wall for 15 minutes
Pain & CBT
I will walk on your body with my high heels to punish you.
I will caress your entire body with nettles.
I want you to lie face down with your hands and feet bound. I will place a vibrating cock ring around your testicles, and you must endure the intense vibrations for a set amount of time without begging for relief.
You will stand perfectly still as I slowly drip hot wax from a candle all over your bare skin. You are not allowed to flinch or make a sound, no matter how much it burns.
I will make you wear a spiked cock ring and watch me undress in front of you.
I want you to lie down on the floor, I am going to trample you.
I will have you wear a maid’s uniform and clean the room meticulously. Any dust or dirt left behind will lead to you being paddled across your buttocks, ensuring you learn to be thorough.
I want you to wear a metal chastity cage and do 10 pushups. Every time you go down I wanna hear the sound of your chastity cage touching the floor.
Bondage
You will share your deepest fantasy involving Me. You will then be tied on a chair and blindfolded, as My partner and Me play this exact fantasy, except you don't get to partake in it.
After I workout I will tie you to a chair and shove my sweaty socks into your mouth and gag you, then put my sweaty panties over your face.
I will gag you with a bit gag and stick a tail plug in your ass and you must act like a human pony all day
I will blindfold you and use a vibrator on you until you plead for mercy.
I'm having visitors. I'll put you in a cage under the table and put a sheet over it. I don't want to hear you all evening, otherwise my visitors can have their way with you.
I will but put a vibrating plug up your ass and tape your cheeks together. Now i will tie you up an leave you lying on the floor.
You will remain chained to the wall, blindfolded, waiting in silence until I decide you’re worth my attention.
I want to cuff your hands behind your back and make you rub your pathetic cock against my boots. If you cum you need to clean it with your tongue and swallow.
Blindfolded and restrained, you will wait in anticipation as I drag a series of different objects - feathers, silk, ice - across the soles of your feet. You must correctly identify each one without being able to see.
My bull is coming over to fuck me. You'll be tied up and gagged under the bed, so you can hear me getting fucked. If you stay quiet I'll let you clean me after me and my bull came.
You will be tied up laying on your back, with your mouth forced open. A drop dispenser containing my urine will be hung above your mouth and you shall stay in this position until the dispenser is empty.
Tonight I have invited a few guests over, I want you to wear a leash and a blindfold and do whatever the person holding the leash tells you to.
I will bind you to a chair for a full day, blindfolded, naked, gagged, with a small cage on your cock and a vibrating plug in your ass. You will wear headphones that will be looping an audio file of my voice leading you deeper into submission.
You will be tied with your legs spread and your ass exposed. I will take a cucumber and insert it into your asshole, making you hold it in place for several minutes.
Pet Play
I'm having visitors. I'll put you in a cage under the table and put a sheet over it. I don't want to hear you all evening, otherwise my visitors can have their way with you.
You are a dog, you will only walk on all fours.
I want you to kneel in the corner of the room for 30 minutes, holding a sign that says "Mistress’s Worthless Pet" above your head, and whimper every time you hear a noise
Humiliation
I want you to change clothes with me in the restrooms of a restaurant
My friends and Me want to play a game with you. We will blindfold you and We will let you smell Our panties, you have to guess which one is Mine. If you guessed wrong there would be serious consequences!
As soon as I come home from work I will put your plug in with a bell on it and nipple clamps with bells too so I can always hear where you are
Every night before going to bed, you will quickly lick my pussy and my dirty hole to keep the taste in your mouth while you sleep
After I workout I will tie you to a chair and shove my sweaty socks into your mouth and gag you, then put my sweaty panties over your face.
You will pick out your favorite lingerie for Me to wear to my date with my bull while I keep you locked in chastity at home.
You will practice my hypnosis routine every day. Melt your mind, pour it in a bowl, and give it to Me. You will become a perfect toy for Me to destroy over and over again.
I want you to extract my milk, make an ice pop then suck it all
You will lie on your back with your legs spread wide. I will insert My strap-on into your mouth, and you will deep-throat it as far as you can, gagging if necessary, while looking up at Me.
I want you to let my female sub play with your cock, let her do whatever she wants
Masturbate in front of Me while I talk about my experiences with My lover. You are allowed to edge yourself, but you must not cum. Each time you get close, you must thank My lover for being better than you.
You will crawl to me, only to be ignored, left to stew in your insignificance.
I will gag you with a bit gag and stick a tail plug in your ass and you must act like a human pony all day
I want you to lick peanut butter from my ass.
You will buy a custom dildo that has been modeled after your own cock. When I am not satisfied with you, I will make you suck your own cock as a punishment.
I want you to write “Mistress’s Anal Slut” on your forehead before presenting yourself on all fours.
You will wear a pink ribbon around your penis whenever you are at home
As punishment you will bounce up and down on this dildo while singing Britney Spears, "Oops I did it again" at the top of your lungs until you are permitted to stop
You will cum in a glass and drink the contents.
I will cover your chest in cum and you can’t wash it for a day
Get down on your knees and beg Me not to punish you
You will wait for me naked in the car parked downtown while I buy something in a shop.
You will have to perform a striptease in front of a group of my friends.
I want you to masturbate wearing panties. Cum into the panties and lick them clean
I have to go to the office this morning. You will come with me and sit quietly underneath my desk, worshiping my feet and eating me out when I demand.
I want you to wear woman's parfume at your work today
I am hosting a party tonight. You will kneel at the entry. Your hands will be bound behind you and you will be blindfolded. Each guest will introduce themselves to you when they arrive. You must memorize the sound of their voice. Through the evening they will come say hello to you. If you reply to them with the wrong name you must satisfy them orally.
I want you to clean all my sextoys
You will wear my bra at the office today and I will video call you several times to check.
I want to install some software to spy on all of your devices so I can know everything you are doing online
I want you to stand naked in front of a mirror and make out with yourself, covering the mirror in spit and tongue marks from your make-out session.
I want you to come with me to the toilet, after I finish peeing you will clean me with your tongue.
You will measure your penis in front of me and announce the measurement with pride
I want you to swallow this Viagra pill and handcuff your hands in your back, then watch me getting fucked by my bull
I will give you a list of degrading names, and you must repeat each one 10 times while looking at yourself in the mirror, nodding in agreement.
I want you to watch as my bull cums on my body, then you will use that cum as lube to jerk yourself off
Me and My lesbian friend are going to spit on you while you edge your cock
I want you to write 'I have a small penis' on your chest and parade in front of me while reciting it loudly.
I want you to suck my toes.
You will be required to have sex with me in public, where there's a risk of being caught.
Lay down on that milking table, time to milk those balls
My bull is coming over to fuck me. You'll be tied up and gagged under the bed, so you can hear me getting fucked. If you stay quiet I'll let you clean me after me and my bull came.
I will smother you with my armpits for 2 minutes.
I will suffocate you with my big juicy ass
Tonight I have invited a few guests over, I want you to wear a leash and a blindfold and do whatever the person holding the leash tells you to.
You will be dressed in frilly sissy lingerie and bound with your hands behind your back. You must worship my ass with your tongue, licking and probing deeply while I mock your pathetic attempts.
I will smother you with pillow for 1 minute.
I will watch you mow my lawn in a mini skirt and sports bra
After a long sweaty workout you will bury your nose in each of my pits for several minutes then lick all the sweat off of my body
I want you to cum into a condom, then use the cum as a dipping sauce as you eat a lollipop
Foot Fetish
Your going to ruin your orgasm onto My bare feet then lick Them clean
I want you to adore my feet while I ignore you
I want you to lick each one of my toes with delight
I will wash my dirty feet in this basin filled with water and then force you to put your face in it!
I want you to look at my heels and edge.
You will sit caged in front of Me while I slowly remove My heels. You may watch, you may worship with your eyes, but if you dare touch, your chastity sentence will double.
You will massage my friend's feet, paying extra attention to her arches and toes, ensuring she feels utterly pampered and adored.
I want you to tell me how lucky you are to serve me while kissing my black boots.
I will attach a bell to your collar, and every time it rings, you must come kiss my feet without hesitation, no matter what you are doing.
I want you to pay 10 dollars to My house maid and beg Her to kiss Her feet.
I want you to pain my toenails wearing nothing but a ball gag and chastity cage
I want you to suck my toes.
I want to cuff your hands behind your back and make you rub your pathetic cock against my boots. If you cum you need to clean it with your tongue and swallow.
I want you to lick my feet.
Every evening you will say good night to my feet by giving a kiss to each toe, the sole and the top of each of my feet
When I come home from work you must come to kiss my shoes without me saying a word.
You will strip naked and crawl to me on all fours. When you reach my feet, you will kiss them reverently before receiving your next order.
Orgasm Control
Your going to ruin your orgasm onto My bare feet then lick Them clean
I’ll order you to use a vibrator on yourself but never let yourself get close to release, repeating this until I tire of watching.
I want you to smell my dirty panties while edging yourself
Masturbate in front of Me while I talk about my experiences with My lover. You are allowed to edge yourself, but you must not cum. Each time you get close, you must thank My lover for being better than you.
You will sit caged in front of Me while I slowly remove My heels. You may watch, you may worship with your eyes, but if you dare touch, your chastity sentence will double.
You will cum in a glass and drink the contents.
I will tease your cock for hours and not let you cum to finally lock you in a chastity cage for another day.
I will jerk you off for five minutes. If you cum during that time, I will put you chastity cage for 30 days.
I want you to masturbate wearing panties. Cum into the panties and lick them clean
I will make you wear a spiked cock ring and watch me undress in front of you.
If you cum without my permission I will make you swallow it.
I want you to watch a porn of my choosing, you will edge yourself to it until it has ended, then you will ruin your orgasm in front of Me
I want you to swallow this Viagra pill and handcuff your hands in your back, then watch me getting fucked by my bull
As a slave, you will never again use your cock to fuck women. You will only pleasure women with your mouth from now on.
My bull is coming over to fuck me. You'll be tied up and gagged under the bed, so you can hear me getting fucked. If you stay quiet I'll let you clean me after me and my bull came.
I want you to wear a metal chastity cage and do 10 pushups. Every time you go down I wanna hear the sound of your chastity cage touching the floor.
I will bind you to a chair for a full day, blindfolded, naked, gagged, with a small cage on your cock and a vibrating plug in your ass. You will wear headphones that will be looping an audio file of my voice leading you deeper into submission.
Maid
Every morning when I wake up I want to find you dressed up like a sissy maid with a cup of coffee ready for Me to enjoy
You will serve drinks from a tray balanced on your back, crawling on all fours. If a drink falls, you will be punished in front of all My guests.
I want you to clean all my sextoys
You will wear lace gloves and delicately serve Me, showing how refined a sissy you’ve become.
I want you to prepare a romantic dinner for me and my lover. You will cook a three-course meal, serve it with elegance, and ensure every detail is perfect. During the meal, you will remain silent and attentive, ready to fulfill any request we may have.
I want you to arrange a surprise date for me and my lover. You will plan every detail, from the location to the activities, ensuring it is an unforgettable experience for us.
I want you to arrange my wardrobe according to my preferences. You will categorize my clothes by type, color, and occasion, ensuring everything is easily accessible and impeccably organized.
You will apply a rich, luxurious lotion to my feet, massaging it in with tender care until my skin feels silky smooth.
I will put a small remote-controlled anal vibrator in you and force you to complete chores with it randomly buzzing you. If you drop anything, you will be punished immediately.
Anyone coming to My home, I want you to serve them the same way you serve Me
I want you to organize my make-up table
You will be responsible for planning and executing a full day of pampering for Me. This will include preparing My meals, giving Me a massage, drawing My bath, and attending to any of My whims and desires throughout the day.
I will have you wear a maid’s uniform and clean the room meticulously. Any dust or dirt left behind will lead to you being paddled across your buttocks, ensuring you learn to be thorough.
I want you to take an online course on how to properly give Me a manicure
A second recording device
Anal plug
Bathtub
Belt
Bucket
Cellophane paper
Chair
Cheese
Chocolate
Condoms
Dress or Skirt
Flour
Forest nearby
Fridge
Headphone
Honey
Ice cubes
Lip gloss
Lubricant
Makeup
Mirror
Scale
Scissors
Stockings
Suction cup dildo
Toilet brush
Toilet paper roll
Toothbrush
Toothpaste
Trash bags
Vibrator
Woman's wig
Women's clothes
Wooden spoon