Sissy predicament bondage

Mistress
Whatever she wants to wear

Sissy maid
Full sissy dress plus her required chastity cage

Furniture & Toys
Electric wand
Paddle
Anal hook
Suspension frame

Do
Have your sissy's wrists tied up as tied to the ceiling or a suspension frame.

This is a game. You give a reward for everything she does right. Every time she does something wrong you spank her really hat with your hand or you paddle her.

For extra delight have her wear ballet shoes (not boots so you see most of her legs in stockings) instead of heels. It'll be harder to move around in and when she moves it'll be funny.

As for rewards make them simple. A deep kiss, 10 seconds I vibrator on her clitty, one day less in chastity before orgasm, the honor of giving you a tongue bath, allow her to watch and play with her clitty out of chastity as you make love to someone.

Predicaments
Foot tickling
Armpit tickling
Nipple sucking
Ball slapping
Electrode stimulation
Face slapping
No erection while watching porn

When this is over put a thick anal hook in her and let her stay there for a couple of hours while you read, knit or watch tv. Keep and eye out and feel free to play with her a little every once in awhile.

Sissy sex slave

Mistress
Skirt
Corset
Stockings
Pin up makeup
Heels

Sissy maid
Skirt
Under bust corset
Chastity cage.
Heels and heel lock
Full makeup, wig, painted nails

Furniture & Toys
Electric wand
Rope
Buttplug
Face strapon

Predicaments & punishments:
Foot tickling
Armpit tickling
Nipple sucking
Ball slapping
Magic wand -> soles of feet & balls
Face slapping
In chastity while watching porn

Do
Have slave lay down on her back while in a straight jacket. Have the slaves ankles tied together with rope then the other end tied to a post so she can't move. She should be in heels at this point.  Perhaps ballet heels or boots because they are super sexy.

While she is wearing the face strap-on sit on slave's face and ride it until you cum or you are satisfied. Perhaps orgasm multiple times while using the hitachi.

At any time mistress may want to take slaves heels off and tickle your slave's feet or use the wand.  Or use the wand anywhere else for the scared eyes and severe squeaking that the slave will do.

Smother her with your genitals to keep her on edge. Yell at her for letting her lipstick smear because it makes slave look slutty when you don't want her to. Put the lipstick back on and make her do it again.

Make her suck the dildo clean before putting it back on. Make sure she does it like a slutty sissy otherwise she'll get it in her ass. It's at mistresses discretion whether it goes in or not regardless. Make sure to deep throat her until her eyes are wet. Anytime is a good time to train the gag reflex.

At mistresses discretion she may let the slave stay in this predicament for as long as she desires. Perhaps using the wand again or tickling again purely for comedic effect for the mistress.

Laying on her chastity device but facing her feet, and slave must not be gagged, you can tickle her while getting information out of her. Perhaps a fantasy or make her recite a poem of your choosing (she should know it ahead of time). Perhaps you tell her that you'll do it for x amount of time and if slave squirms you spank her ass with the paddle 3 times. Maybe you sit on the floor and make slave clean your feet. This is a fun idea to also do after a workout so they are nice and sweaty.

Once this part of the scene if over let her "free" and let her fix her makeup, hair and/or attire and have her serve you. Perhaps you can watch tv while she is on her hands and knees and you have a plate on her back.

Sissy slut object horsing around

Mistress
Whatever she wants to wear

Sissy maid
Leather under-bust corset
Black FF stockings
Ballet boots
Metal chastity cage
Posture collar
Wig and makeup
Dicklet ribbon
Black leather open faced hood
Red ball gag
Blindfold of sorts
Nipple clamps with weights
Leather arm binder
Hands taped up into balls
Leather mini skirt

Furniture & Toys
A Symbian with an anal inpatient that vibrates very intensely. Perhaps attached to a hitachi somehow.

Rope
Paddles
Floggers
Electric prods
Fucking machine
Camera

Do
Have your sissy put in her wig, do her nails and makeup and shave all over.

Let her put on her stockings and garter. Help her into her miniskirt and corset. Help her put on her ballet boots.

Put on her collar and hood. The hood should be nice and tight. Once you've taped up her hands well put her into her mono glove.

She's fully dressed at this point so feel free to use your sadistic side to pinch, prod, slap, and hit her baby. Maybe even slap her balls some or spit on her. Humiliation and corporal punishment is a huge turn on for a lot of people especially your slave.

Walk your slave object to where you've put the Symbian. It would be best put in a place with hookups for rope. Lube up the dildo on your saddle and have her sit on it. As her knees are bent tie her legs together (each leg in its own) so she can't really move. Tie the tip of the mono glove to the ceiling and her collar to the floor

She should be completely unable too move and just struggle. ask her to try to get out of her entrapment. The struggle should give you the giggles.

If you can add a bit of predicament bondage to the mix then let it be so.  For instance if you put an electrical pad under your slaves balls to shock her if she moves even the slightest but that would do wonders for your vindictive/sadistic side.

At this point you should put on her nipple weights and ball gag. Feel free to do what you want to her nipples. Suck on them or flick them or slap and bite them. It's completely up to you. You're making maiming furniture and you get to interact with your furniture in any way that you wish.

This would be a great moment to turn on the vibrator and watch what happens with glee. The deeper and wider the dildo is the more fun you will have. if it spins in any way then watch out. She will probably cum in seconds and after that it could just be a torture.

If the relationship is there then have your boyfriend over for a bout of sex. Have him touch and play with your sissy object. This would be a good time to take off the gag, tuen off the Symbian and have your sissy slut get your boyfriend excited, hard.

Do whatever you want with your boyfriend but make sure that the machine is off so that your slave can here what you are up too. Blind folded and gagged. Do it in the same room.

Once you're finished have your boyfriend blow his second load in your sissy's mouth. It's a present. Let her enjoy it.

Maybe after he leads or while he's still there remove the rope from the mini glove and remove her boots. She is most  likely very sweaty and let her cool off some.

Pull on the rope on the collar and tie it tighter so that she's completely bent over with her smooth big ass in the air. Feel free for both of you to laugh at her awkward position. She looks like a bitch in heat but with balls and emasculated.

Ow would be a great time to have your boyfriend spank her ass as hard as possible. Making them red. If you two want and he can fuck her ass. Either way this is just time to let the fucking machine do its work. Possibly put your genitals in her mouth as her mouth should be near the floor. If you and your boyfriend are good to go again then, then, fuck again.

When the night is over and you let your slave object out of her predicament she will be on a very big high and you will need to spent plenty of time with her cuddling and taking care of her as she comes out of from sub space.

Let her sleep in the puppy cage.

Sissy maid service

Mistress
Whatever she wants to wear

Sissy maid
Corset
Ff stockings
4.5" heels or higher
Heel locks
Chastity cage
Dress and corset
Wig and makeup
Dicklet ribbon
Inflatable anal plug (if desired)

Do
Have her wait on you hand as foot. Make sure that you make her suffer.

Any time you leave make sure to tie her to her "resting" place. Posture

Slave bitch object

Mistress
Jeans
Stockings
Corset
Heels
Sultry makeup (if any desired).

Slave Object
FF stockings (red)
Black leather under bust corset
Latex mitts
Latex full cat hood (red eyes and mouth)
Latex catsuit
Leather belt straps
Long black hair wig
Ballerina Heels (boots?)
Chastity cage
Leash
Toe nail and hand nail polish.
Various butt plugs (doggie tail)

Do this
Firstly use the belt straps to turn your slave object into a puppy. To do this mimic the bitch suit by belting each leg to itself and the arms as well. Left arm to left shoulder and left ankle to left thigh.

At this point why not use your plaything like the object she is. Have her walk up to he couch and lay things on her back and use her as a table.

The next parts are ideas and are in no particular order:

Or have her walk around the house as dog and bark at command. Make her whimper by plunging a large dildo in her ass repeatedly and or paddling her latex clad ass with a wooden spoon.

Force feed her a gallon of water and make her pee into a pail. Then have her grab the pail with her teeth and bring it to the bathroom.

Take off her Ballerina boots and tickle her feet until she whimpers. Make sure to put the gag in her mouth first.

Talk to her like a pet and punish her when she doesn't do something right or fast enough.

Humiliate your object by telling her that she can't fuck you. Or that her dick I'd useless so it's caged in plastic/metal.

Humiliate her by masturbating using the hitachi in front of her face. When done take off her gag or mouth covering and make her clean you off.

Use make her cum onto a plate by either using the hitachi or prostate massage. Then she must slowly lick it up while your laugh.

Use a small stick to flick the soles of her stockinged feet. Whenever she whimpers you add 3 more strikes. Start with 10 strikes.

Slap her balls. Possibly flick them with your finger or a rubber band. If her mascara runs down her face from tears the. You've done something right.

Leave items around the room. Have her pick them up with her mouth. Give her a time limit to bring them all to you. If not accomplished you punish her in your choosing. If accomplished give her some love (hugs, petting, kissed, gentle caressing, on her back and back rubs) and then lower the time limit and have her do
It again until she fails. Repeat for your own amusement.

Slap her face whenever she does something wrong.

Make her eat from a bowl.

Put a suction cup dildo at anus level on a wall. Then put on your strap-on. Lead your slave object to the wall until she is penetrated by the wall dildo. Now fuck her mouth with your dildo. Don't stop I'd she gags. Don't stop if her eyes tear.

Finish:
When done your scene(s) would have been a few hours if not more. Your slave object would have been drenched in sweat. Undress her and bring her to the shower.

She may be in sub-space and coming down. Make sure that you carefully being her into the tub or shower. Gently and lovingly clean your slave.

When dried off put her in bondage for storage while you go to watch a couple hours of tv or movies. She's in a cage so she can't get off. Plug her up and or put on her favorite item of clothing. Wigs and stockings.

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Slave object penetration

Mistress
Jeans
Stockings
Corset
Heels
Strap on
Sultry makeup (if any desired).
Leather (fucking) strap for the waist

Slave Object
FF stockings (black)
Black leather under bust corset
Leather full hood
Long black hair wig
Heels
Heel locks
Chastity cage
Black straight jacket
Dildo harness, chastity compatible
Black/Red dildo
Posture Collar (may be too much)
Leash
Toe nail and hand nail polish.
Ankle spreader
Slutty make up

Do this
Firstly to warm her up have the slave object stand in her getup while you watch tv. If training start at 10 min and work your way up to an hour. For extra pain put hard rice in her heels. For even greater discomfort put in inflatable anal plug. There will be no way to not eroticize the situation.

Finally, when ready of course, using the leash clipped to the collar lead the slave object to the bedroom or an elevated stable platform. Be careful but get her on the platform knees down. Since she'll be in a straight jacket slowly put her down. Put on the ankle restraints.

If any anal device is in your slave object please remove then now.

Put the leather strap around the slave object's waist and pull her closer to the dong on your strapon. Fuck the shit out of her while using the waist strap for leverage to get maximum penetration.

At any time during or after feel free to paddle your slaves ass, balls or feet. Slap her face or dig your nails deep into her skin. Hot wax is also a hilarious option. Let her squeal.

Don't let her cum. If she does even by accident the punishment is an extra 2 weeks added onto her sentence.

Slave object dildoing.

Mistress
Stockings
Corset
Heels

Slave Object
FF stockings (black)
Black leather under bust corset
Leather full hood
Long black hair wig
Heels
Heel locks
Chastity
Butt plug (maybe? Tail?)
Monoglove (hand cuffed too?)
Dildo harness, chastity compatible
Black/Red dildo
Collar
Leash

Do this
Mistress is on the bed on her back and slowly and carefully walks slave object to the bed. Mistress lays on her back in the edge and with a leash tugs on the slave objects collar to instruct for each penetration.

If slave object doesn't penetrate on a tug mistress will paddle her ass. When mistress finally cums she will let slave object stand until she deems fit.

If slave object does well and mistress is satisfied then mistress will put a condom on cage and use vibrator to get slave object to cum into it. She will collect the cum and make the slave object eat it. For extra humiliation mistress will pour the remains on her stockinged feet and have maid eat it off there.

A simple cuckold fantasy.

I'll make this one quick as I need to get to bed.

I am, of course, in chastity. Perhaps by this point I've been in my cage for a couple months now with only prostate milkings and teasings to keep my erotic energy to their maximums.

My wife, my Mistress, has her boyfriend over. I, in full sissy garb and makeup, serve them and make them comfortable and help them get into the mood.

Mistress demands that I fluff her new boyfriend as she's taught me. She'll demand that I do this while she gets ready so I need to keep him hard w/o making him cum. He's to be aroused but not finished off. Soon after, a couple minutes at the most, she walks over and brings him to her bed.

I follow just to pick up any clothes that they drop to the floor as they undress each other or to carry drinks. I may be demanded to watch or the door is shut  and I have to hear the sounds of ecstasy emit from the other room.

After he finishes inside of her I'm obliged to suck out all his semen from her vagina and clean her off. Perhaps him as well.

They may happen more than one time over the course of their late night.