Slave SissySlaveJimmy

1 day ago

Free

Other, 54 yo

United States - Overland Park

Anal Play

Nipple Play

Sissy

Discipline

Pain & CBT

Toilet Play

Bondage

Pet Play

Humiliation

Foot Fetish

Orgasm Control

Maid

Masters/Mistresses Ratings 4 rating(s)

Thorough

Fast

Grateful

Respectful

Medias Quality

English

Submissive

Humorous

Versatile

Toys

High Limit

Faithful

Introduction
Kinks
Toys

I am looking for a mistress who truly enjoys humiliating and punishing an older submissive male. My primary attributes are high pain tolerance and a considerable amount of experience IRL for the last 30 years or so.

Only the skills of level 2 and below are displayed, you need to be a registered Master/Mistress to see all the skills.

Anal Play

I want you to wear your rosebud all day and send me 3 pictures of you wearing it in 3 different public locations.

You will insert a phallus shaped vegetable of my choice in your asshole

I will put a vibrating but plug in your ass with an ash tray attached to it and you will stay bent over beside me while I smoke and if you drop any ash I will put it out on your ass cheek

I want you to moan loudly while I fuck your ass.

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.

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 will make you cum on a buttplug and put it up your ass. You are only allowed to remove it after you've come a second time.

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.

Nipple Play

I'm going to tie your hands behind your back and suspend tea bags from your breasts. You will bend to infuse until I tell you to stop.

Sissy

You will be kneeling in the entry way of my home during a house party, wearing only panties and a bra - as each guest enters you will give their crouch a kiss

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.

You will wear a woman's wig, fake nails, makeup, heels and be treated like a whore.

Memorize and recite the lyrics to a Taylor Swift song while dressed in women's lingerie. You must perform it in front of Me as if you were Taylor Swift herself.

I want you to wear a lipstick under a Covid mask outside

From now on I want you to dress as a maid when we're at home

I want to test my new make-up on you first before I'll try it on myself.

Discipline

You are not allowed to talk to any women without My permission.

I want you to help me prepare dinner and then be my serving boy as I eat dinner, if you're hungry you can eat leftovers from a dog bowl after I'm done eating and you've washed the dishes

I won't let you use any technology because your only purpose is to serve me

Kneel down and hold the phone, so that I can watch a movie on it.

You will be gagged and blindfolded, kneeling with weights attached to your genitals. I will slowly add more weights, forcing you to endure the increasing pressure. You must remain perfectly still and whisper My name continuously.

I will play with your dick until you cum in your pants, you will not clean it up or change pants, but wear them for the rest of the day

I will gently run the tips of my fingers up and down the soles of your bare feet, watching with delight as you squirm and try to suppress your laughter. You must remain perfectly still, no matter how unbearable the sensations become.

If you cum without my permission I will make you swallow it.

I will tie small bells to your toes and challenge you to walk without making a sound. If you fail, you will be subjected to a severe punishment.

I want you to keep a daily log of punishment on which you will indicate your faults

While walking in public, you would always walk behind Me

Stand facing the wall, arms and legs outstretched and hold a coin with your nose to the wall for 15 minutes

You are not allowed to curse anymore. Every time I hear you curse, I will have you keep a soap in your mouth for 5 minutes to clean your mouth!

You will learn to respond to various whip lashes and other impacts with appropriate vocalizations and reactions.

You are not allowed to speak for 7 days

When guests arrive, you will crawl to greet them on hands and knees, head bowed in deference. You are to remain at their feet until dismissed.

Each evening, you will stand before me completely nude, head bowed. I will then slowly and methodically inspect every inch of your trembling form, taking note of your response to my touch.

I will be sitting on my computer chair that will be tied with a rope to your balls and you will be naked on all fours like a dog. You will take me wherever I ask you to and I will whip you if you are not fast enough.

When I say "present yourself" you will stop what you are doing, remove your underwear and kneel in front of me with your legs spread. Don't you dare close those legs until I'm finished with my inspection!

I want you to confess to Me every day

Put a collar on your neck, go out and kneel down while holding the leash with your mouth, wait in front of the door until i come back

You will take off your clothes and walk like dog in the garden in the middle of the night

While I’m on vacation you’ll stay at my home. You’ll stay in chastity and I want a clean house when I return. If I’m not pleased you’ll be punished.

I will make you freeze your pee into ice cubes and force you to suck one every time you disappoint me

I want you to stop immediately what you are doing and shut up when I snap my fingers, and you will kiss my hand to show Me your gratitude and respect

Pain & CBT

You will hold a grape between your teeth and bend over with your hands flat on a table. I will count down from one hundred as I cane you. If your teeth cut the skin of the grape or if you drop it I will stop. You will owe me the remaining number of days in chastity.

You will be tightly bound to a chair with your chest exposed. I will drip hot wax from a candle onto your nipples and chest. You must thank me for each drop and apologize for your weakness.

I will make you tie your balls separately with shoelaces and you will come jogging with Me

I will put a shock collar around your neck and we will play blackjack. When you lose you will get a shock and when you win you can kiss my heels.

Stand naked in front of Me and spread your legs wide. I will use a small whip or flogger to lightly lash your testicles 50 times, varying the angle and intensity to keep you on edge.

I want you to stand on your tiptoes with your arms tied above your head. I will attach clothespins to your nipples and testicles, increasing the number of clothespins with each passing minute to test your endurance and pain tolerance.

I will put a vibrating but plug in your ass with an ash tray attached to it and you will stay bent over beside me while I smoke and if you drop any ash I will put it out on your ass cheek

Lie on your back with your legs elevated and secured. I will use a feather to tickle your testicles, followed by sharp, sudden pinches, alternating between pleasure and pain to keep you guessing and on edge.

You will learn to respond to various whip lashes and other impacts with appropriate vocalizations and reactions.

I want your body pressed against the window while I peg you

I will tie you down and blindfold you. My bull and I will take turns thrusting deep inside of you. You will get one guess if it is Me or my bull. If you are wrong, you will receive 10 lashes from my cane.

I want you to call in a delivery order for my dinner. But you must wear a ring gag. You will receive 10 lashes of my cane for every mistake that is made of my order.

I’ll tie your hands behind back and put 8 ice cubes in your pants. You have to suck my pussy till the ice cubes melts.

I had a bad day, and I am so angry I feeling like insulting and humiliating you so I want you to get down on your knees and bow in front of me while I whip you and degrade you.

You will be standing up naked, your hands tied up to the ceiling as I will whip you with nettles.

I will make you wear a spiked cock ring and watch me undress in front of you.

I will insert a sound into your peehole

I will make you carry weight from your testicles to make sure you will be slow and careful in your moves.

Toilet Play

I want you to lick the toilet bowl as a punishment.

Remove your clothes and lay in the bathtub, I will do an anal enema and release the water all over your body.

Bondage

You will be tightly bound to a chair with your chest exposed. I will drip hot wax from a candle onto your nipples and chest. You must thank me for each drop and apologize for your weakness.

I will make you tie your balls separately with shoelaces and you will come jogging with Me

Get inside the bathtub, I will tie your hands and legs and urinate all over your body.

I will tie your wrists and ankles to a chair, then edge you repeatedly with a vibrator. You must hold back your orgasm until I give you explicit permission to release.

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.

I want you on all fours next to my bathtub. I will put candles and my glass of wine on your back while I am taking a long relaxing bath.

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'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 will be tied up and I will make you take a cold water shower.

I want to leash you by the cock and take you around

I want you to take your coat and put your hands in the pockets. I will handcuff you underneath and we will go for a walk.

You will be standing up naked, your hands tied up to the ceiling as I will whip you with nettles.

You will kneel in front of the toilet tied up, after I've urinated in it, for an hour.

You will drink a full liter of water now and I will punish you by tying you to the bed and tickling you with a feather until you pee on yourself.

I will lock you up in the closet on your knees and leave you there for as long as it pleases me.

You will go to somewhere I decided with a pair of socks in your mouth

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.

Pet Play

You will present yourself naked and on all fours. I will place a leash on your collar, and you will crawl around the room following My commands, barking like a dog.

Put a collar on your neck, go out and kneel down while holding the leash with your mouth, wait in front of the door until i come back

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 will take off your clothes and walk like dog in the garden in the middle of the night

I will put a short leash on you and tie the leash to my ankle so you will have to follow me on all fours everywhere I go

You are a dog, you are only allowed to eat and drink from the pet's bowls.

Humiliation

You will sit on this chair naked and play guitar to entertain our guests.

I want you to help me prepare dinner and then be my serving boy as I eat dinner, if you're hungry you can eat leftovers from a dog bowl after I'm done eating and you've washed the dishes

I want you to cum on your hand and slap your face with that hand

I want you to lick the toilet bowl as a punishment.

Get down on your knees and beg Me not to punish you

Naked, you will introduce yourself and talk about your submission to your mistress, to express your greatest fantasy and answer questions, in front of an assembly of at least seven people

You will accompany me shopping today, you will carry my handbag for me, always walk 2 steps behind me and produce your credit card from my purse whenever I click my fingers.

I want you to wear your rosebud all day and send me 3 pictures of you wearing it in 3 different public locations.

I want you to kneel next to me with ashtray gag and wait for me to finish my cigaret

I will make you look directly into my eyes while my bull fucks me from behind making me cum.

You will be kneeling in the entry way of my home during a house party, wearing only panties and a bra - as each guest enters you will give their crouch a kiss

Your job this week will be to clean my whole dungeon and equipments everyday.

I will play with your dick until you cum in your pants, you will not clean it up or change pants, but wear them for the rest of the day

There is mud on the path you will lay down in it for Me to walk on you past it

My trash can is full, I want you to sort the waste into paper, organic, and tins, and take them to the relevant containers outside.

I want you to remove the dead skin from my feet.

I will have you kneel before Me and lubricate the strapon. You will then take the strapon into your mouth and deepthroat it until I am satisfied with your performance.

There is a puddle of water. Take off your jacket and put it on the water so i can walk over it without getting my shoes wet.

Here are two very nice pastries for us. While I will be eating mine, you will be dropping yours into your underwear and give yourself a good massage down there and watch me eating.

I need to pee. Get on your knees, look up and open your mouth. I want you to swallow every drop of it.

I will put a shock collar around your neck and we will play blackjack. When you lose you will get a shock and when you win you can kiss my heels.

I want you to masturbate me and swallow my cum.

My garbage bag is full, move all the trash into a new one and put your head inside the old one. I will tie a knot around your neck and make small holes for you to breathe.

Get inside the bathtub, I will tie your hands and legs and urinate all over your body.

I will put a vibrating but plug in your ass with an ash tray attached to it and you will stay bent over beside me while I smoke and if you drop any ash I will put it out on your ass cheek

You will create an outfit using garbage bags and wear it until the end of the day

Look how much I have squirt on the floor, be a good boy and lick it clean

I want you to learn how to sew, so you can sew your new mask using my old panties when I replace them with new ones.

You will go out for a walk with a pair of cotton socks but no shoes, when you come back you will put the socks in your mouth as a punishment

We're going to measure your dick. You'll wear a collar displaying how many inches it is.

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.

Wear a chastity device while I describe in detail a sexual encounter with My lover. You must thank Me for sharing and beg to be released, knowing that only he can fulfill My needs.

I want your body pressed against the window while I peg you

I want you to act like a piece of furniture (clothed) for the afternoon, in front of everyone.

I want you to sunbathe in the garden today but you are going to be wear my bikini

I will cum on your food and make you eat it.

You will follow me closely in a busy area, and each time I stop, you will discreetly kiss my ass through my clothes.

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.

Whenever I order you will take a remote-controlled toy and wear it around all day. I don't care what you're doing right now, whether you're shopping, you have a meeting or you're just free. If I want to, I'll play with you. If it doesn't really suit you at that moment, you can try to beg me to stop and hope I take pity on you.

I want you on all fours next to my bathtub. I will put candles and my glass of wine on your back while I am taking a long relaxing bath.

You will go live on webcam with a vibrator strapped to your cock. I will command you to edge and deny yourself repeatedly, thanking me for each denial and describing how desperate you are to cum, begging for more control.

I want you to clean my toes with your toothbrush.

I want you to lick peanut butter from my ass.

I want you to call in a delivery order for my dinner. But you must wear a ring gag. You will receive 10 lashes of my cane for every mistake that is made of my order.

You will wear a woman's wig, fake nails, makeup, heels and be treated like a whore.

I want you to cum inside me, then I will sit on your face and you will have to lick it out of me.

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.

Remove your clothes and lay in the bathtub, I will do an anal enema and release the water all over your body.

I will trample banana with my heels and you are gonna lick it off my heels.

I want you to tell how much a pathetic loser you are to Me

I will take care of you like a mommy.

I want you to get down on your knees and beg me for forgiveness while I spit on your face.

You will not marry anyone because your purpose is to serve me for the rest of your life

I will spit on the ground and you will lick it.

I want you to kneel down and keep barking until i tell you to stop

You will take off your clothes and walk like dog in the garden in the middle of the night

You are a dog, you are only allowed to eat and drink from the pet's bowls.

I'm going to brand you with my initials just above your sex so everyone who sees knows you're mine

You will wear my bra at the office today and I will video call you several times to check.

I want you to install cameras in your home and give me the control over them. So you'll never know if I am watching you or not.

I'm going to grab you by the hair and spit on your face until your face is completely covered with my spit.

I want to leash you by the cock and take you around

You will hang a cat bell to your sex so that your Master/Mistress always hears you moving.

Here is a glass of wine for you but before you drink it I will add a few drops of my pee inside because real wine is too good for a slave.

This is an ice cube made with pee, I will rub it gently on your lips for you to taste it.

I will make you freeze your pee into ice cubes and force you to suck one every time you disappoint me

I had a bad day, and I am so angry I feeling like insulting and humiliating you so I want you to get down on your knees and bow in front of me while I whip you and degrade you.

I'm going to tie your hands behind your back and suspend tea bags from your breasts. You will bend to infuse until I tell you to stop.

I will only allow you to drink out of a baby bottle.

I want you to masturbate and edge 3 times before I will make you ruin your orgasm on my feet.

You will kneel in front of the toilet tied up, after I've urinated in it, for an hour.

You will make an omelette with your cum as an ingredient and then eat it

I will wrap your hands with double side tape and watch you masturbate

It's time for you to be marked as my property we are going to the tattoo parlour today to get your slave name tattooed.

I want you to clean my pussy with your tongue after coming back from a date

I have put cherries in my ass, I will be walking naked and I want you to follow me on all fours. If a cherry pops out of my ass I expect you to eat it.

I will put a clip into your nose and tie a rope to it. Then we will go on a walk my little doggy.

You will wait for me naked in the car parked downtown while I buy something in a shop.

I want you to clean my sneakers with your toothbrush

I want you to open your mouth so that I can put whatever pleases me inside.

I want you to fuck Me, too bad you are wearing your chastity cage... Get my strapping you can use that, it is much better than your pathetic cock

I will make you carry weight from your testicles to make sure you will be slow and careful in your moves.

Foot Fetish

Go on your knees in front of me and kiss each of my toe one by one

You will carry a small footstool and place it for me to rest my feet while we wait at the bus stop. Use the time to massage my feet.

I want you to remove the dead skin from my feet.

I want you to wear a blindfold and kneel in front of Me. You will then kiss and worship My feet, using only your lips and tongue, until I tell you to stop.

I want you to clean my toes with your toothbrush.

I will trample banana with my heels and you are gonna lick it off my heels.

I will lock you in chastity. The only way for you to get out is to find the right key inside of one of my dirty socks from my laundry basket. You will be blindfolded and your hands will be tied behind your back so you will have to use your mouth to find it.

I want you to do Me a pedicure under my desk while I work in my office

I want you to clean my sneakers with your toothbrush

I will put the socks of different women into your mouth. You will guess which socks are mine or be punished!

All my shoes need cleaning, you will clean and polish every pair I have in the house and line them neatly for my inspection, of course you will be punished if any pair fails to meet my expectations.

Orgasm Control

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 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 to see clothespins on both of your nipples while you edge yourself

I will tease your cock for hours and not let you cum to finally lock you in a chastity cage for another day.

Ruin your own orgasm in front of me and eat up your mess

If you cum without my permission I will make you swallow it.

I will tie your wrists and ankles to a chair, then edge you repeatedly with a vibrator. You must hold back your orgasm until I give you explicit permission to release.

Wear a chastity device while I describe in detail a sexual encounter with My lover. You must thank Me for sharing and beg to be released, knowing that only he can fulfill My needs.

I want you to masturbate yourself only with a corner of a table.

While I’m on vacation you’ll stay at my home. You’ll stay in chastity and I want a clean house when I return. If I’m not pleased you’ll be punished.

I will make you cum on a buttplug and put it up your ass. You are only allowed to remove it after you've come a second time.

I want you to masturbate and edge 3 times before I will make you ruin your orgasm on my feet.

I want you to wear chastity anytime when you are not with me

Mistress will lock your chastity cage to the kitchen table with a leash until you make her a meal, let her eat it without looking at her, and clean up the entire kitchen afterwards.

I will make you wear a spiked cock ring and watch me undress in front of you.

I want you to masturbate without touching your genitals with your hands

I want you to fuck Me, too bad you are wearing your chastity cage... Get my strapping you can use that, it is much better than your pathetic cock

Maid

I want you to help me prepare dinner and then be my serving boy as I eat dinner, if you're hungry you can eat leftovers from a dog bowl after I'm done eating and you've washed the dishes

Your job this week will be to clean my whole dungeon and equipments everyday.

My trash can is full, I want you to sort the waste into paper, organic, and tins, and take them to the relevant containers outside.

I want you to thoroughly clean my room. Fold my clothes by category & put them away. When you’re finished, text me that you’re done then wait facing the corner for me to come inspect the task.

I expect you to clean and prepare the bedroom for me and my lover. The bed should be made with fresh sheets, and the room should be filled with a pleasant scent.

You will wash and shave your Mistress legs and then apply moisturizer

You will be dressed in frilly panties and a maid’s apron. You will wash, dry, fold, and put away all of our laundry, making sure everything is perfectly neat and tidy.

I will host a party. I will pick a uniform for you to be the butler/maid for the duration of the party and use a remote vibrating plug to summon you for any services I desire.

You will practice the delicate skill of applying my makeup, ensuring every stroke is perfect. One smudge means starting over from the beginning.

You will be dressed in a degrading maid outfit and bound with cuffs and a collar. You will prepare and serve a meal for My lover and Me, standing by to refill drinks and attend to Our needs while We eat.

From now on I want you to dress as a maid when we're at home

I'm going to tie your hands behind your back and suspend tea bags from your breasts. You will bend to infuse until I tell you to stop.

I want you to wake Me up every morning by serving me some coffee and the newspaper

Mistress will lock your chastity cage to the kitchen table with a leash until you make her a meal, let her eat it without looking at her, and clean up the entire kitchen afterwards.

Anyone coming to My home, I want you to serve them the same way you serve Me

All my shoes need cleaning, you will clean and polish every pair I have in the house and line them neatly for my inspection, of course you will be punished if any pair fails to meet my expectations.

A second recording device

Anal beads

Anal plug

Ball gag

Bathtub

Belt

Books

Bucket

Burning sensation (Tabasco, chillies, Tiger balm...)

Cane

Car

Chair

Clothespins

Cock lock

Cock ring

Cock shaped item

Collar

Computer chair

Corset

Cotton swab

Deck of cards

Dice

Dildo

Dildo gag

Dress or Skirt

Duct/Packing tape

E-stim

Electric toothbrush

Enema pear

Flat thumb tacks

Flogger

Flour

Forest nearby

Freezer

Fridge

Funnel

Garter belt

High heels

Humbler

Ice cubes

Lip gloss

Lipstick

Lubricant

Maid uniform

Makeup

Mask

Mirror

Mouth gag

Nail Polish

Nipple clamps

Panties

Prostate massager

Rice

Ring gag

Rope

Rubber bands

Ruler

Salt

Sand paper

Scale

Scissors

Shaver

Shoelace

Stockings

Strap on

Straw

String

Suction cup dildo

Swimming suit

Tabasco

Team Viewer

Tennis ball

Thumbtacks

Tiger balm

Time lock

Toilet brush

Toilet paper roll

Toothbrush

Toothpaste

Trash bags

Tray

Tweezers

Ty-Rap ties

Vibrator

Weighted nipple clamps

Woman's wig

Women's clothes

Women's shoes

Women's socks

Wooden spoon

Slave SissySlaveJimmy

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

Masters/Mistresses Ratings 4 rating(s)

Anal Play

Nipple Play

Sissy

Discipline

Pain & CBT

Toilet Play

Bondage

Pet Play

Humiliation

Foot Fetish

Orgasm Control

Maid

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