60 Ideas for humiliating your sissy on cam or phone
Something all sissies need to accept is that their Mistress will want to humiliate them as much as possible. This is just a fact of life. How severe she does will depend on how sadistic she is and what kind of mood she is in but ultimately, it’s going to happen.
There are many ways a sissy can be degraded and the only limit is a Mistress’s imagination, which can be incredibly cruel. There is no shortage of ways in which humiliation and degradation can occur.
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Here, we will give you some of the top 60 ways that a sissy can feel humiliated, both online and offline.
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1 – Make them curtsey
Have them curtsey to you every time they walk in a room or serve you. Make sure they do it correctly each and every time, disciplining them if not done correctly. Making sure they always curtsey is a highly humiliating thing to make a sissy do and even more so if you stipulate they must always hold the hem of their dress or skirt and lift it as they curtsey. Mock them as they struggle to do it in heels, laugh at them if they stumble and keep making them do it all the time.
For added humiliation purposes. have them do it in front of your friends or real man lover just to ensure they feel the degradation of an audience.
2 – Get a tattoo
Get them tattooed. Something humiliating like “Pretty Polly cock sucker” or “Cum dump Mandy”. Or just have them get your name tattooed on themselves so everyone knows they are owned forever. Making them get a tattoo is the ultimate symbol of ownership and isn’t something that can be taken lightly. It certainly is not for the faint-hearted but if you decide to go ahead with it, then you have genuinely found a sissy who is yours. They will not be able to go to another Mistress or even form a relationship with a woman other than you due to the tattoo.
You can let them get it in a nice discreet area where only you and they will ever know about it. Top of their thigh or on their ass cheeks, but if you are feeling cruel and want everyone to know they are owned, then get it done on their chest, arm, back or the ultimate areas, the face or neck.
3 – Fill their ass
Fill their ass with whatever you can find and see how much you can shove up there till they beg you to stop. Tampons, dildos, rolling pins, cues, bats, anything you can lay your hands on, Pegging phone sex
Having their ass filled should be the duty of every sissy under your control. It’s sissification 101 to always crave having your sissy pussy filled. Make them beg for it.
Have them get on their knees and beg and plead for you to make them take huge objects and sex toys up their slutty asshole. Mock their attempts as pathetic and make them beg harder. Laugh at them for being such a slut they desperately want to be fucked in the ass. As you make them push the toys in deep, have them thank you for the privilege.
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4 – Pimp them out as a cheap fuck
Set them up a profile on a gay hook-up site and make them suck cock or get fucked for money. Money that goes directly to you. Make them work hard to earn you money. I love to make sure my sissy sluts do this or they get exposed, see the sissy exposure page to find all the little sluts who needed to be exposed for failing their cock sucking tasks. They were all submitted to an exposure site and will remain on it until they complete their tasks.
Keep them working as much as possible for you. Sucking cock nonstop, receiving cock in the ass one after the other. Double your money by getting two guys simultaneously and spit-roasting sissy kins. Work them hard and keep them on their knees or bent over to keep the money rolling in for you.
5 – Anal training
Subject them to daily training to stretch their asshole and get them used to getting fucked in the ass and taking huge cocks in it. Progress steadily to bigger and thicker dildos and vibrators. I enjoy stretching asses and using prostate play and anal orgasms to get my sissies fully stretched and fully ready for the real deal. The alpha cocks that she will take for me. The bigger the toy, fist or cock the better for Mistress.
All sissy sluts need to be able to take huge dildos, vibrators or real cocks in their ass and it is essential to make sure they undergo training for this as much as possible. Most of them will be anal sluts who will be desperate for it but some may resist. Don’t let up, and keep going. If using anal training cams, make them keep to a schedule to keep coming to see you.
6 – Public humiliation
Have them go shopping at a busy store while dressed as a sissy maid or sissy whore. Or alternatively, have them buy just cucumber, lube, and condoms from a female assistant. I love outdoor public humiliation, speaking loudly so everyone can hear walking around with them all dressed up. Making them pull the panties up to over the top of the back of their trousers and then go into a shop, giving them outdoor risky tasks while on the phone, cam or real-time. I do love outdoor and risky public humiliation sessions,
A favourite of mine is to send them to a shop and buy ONLY a cucumber, condoms and lube and force them to pick a young female cashier. This is hilarious to me as I watch the cashier struggle not to look and the sissy struggle not to die of embarrassment!
7 – Change their name
Something female like Kandi or Melina. Or a whore name like Kandi cock sucker or Cum slut Camilla. Anything humiliating that makes them know they are no longer male.
Whatever it is, it won’t be very comfortable for them. They’ve had their name since birth and now you’ve just decided to change it and make it something embarrassing. Have them tell you over and over what their new name is. Use it yourself often, even when you would not normally use a name. Keep using it as much as possible to remind them of their place and what they are now
8 – Make them go on cam with you
If you are an online Mistress who does femdom webcam, have them go on cam with you to be used and let your other slaves decide what to do with them.
This will feel almost like exposure to them and they will be mortified at being forced to perform degrading acts on the whim of other men, especially if they themselves are submissive and sissies. That is good for you though as the more degraded your sissy feels, the more fun you can have!
Be sure to tell your cam users that there are no limits on how far they can push your sissy on the webcam. In fact, be sure to let them know that the more humiliating and degrading the better!
9 – Lock them in chastity
Take that tiny clit of theirs and lock it in a chastity cage to leave them desperate and denied. Don’t let them touch it or gain relief and make them earn their orgasms. You could have so much with this one. Unlock them then take them out and edge them, deny them, ruin the orgasm, milk them and post-orgasm torture. Rub the chastity, finger it, play with it, tease it, torment it and frustrate the hell of the little bimbo sissy princess – If you are ready for domination phone sex with me then be sure to click and call me now
Put their little clitty in a cage, and don’t let it out. Make them earn a release. Make them beg for it. Have them get on their knees and grovel to be released. You can make them do anything you want when their clit is under your control.
10- Burn all their male clothing
They are not a man anymore; they are your sissy so ceremoniously burn their male attire, so they know they will always be a sissy 24/7 for you now. Take his boxers, his trousers, jeans, shirts, everything he has that makes him look male and set it on fire. Make the humiliating act worse and have HIM do it instead.
Make a ceremony of it and make sure he realises his male life is over or do it even more callously and just take them out, set them on fire then walk away without a second thought.
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11- Cuff their ankles together with a short chain
Lock ankle cuffs on them that are bound together with a short (6 or 7 inches or so) chain. This forces them to take lots of short mincing steps when walking. Laugh at them as they keep stumbling when the chain pulls tight and mock them for not being able to walk correctly. Also, keep making them do pointless trips back and forth to fetch things for you. Keep them walking as much as possible!
If you feel particularly cruel, make them walk up and down a flight of stairs!
12- Pour full condoms over their head
Have them sit there as you empty an entire condom filled with spunk over their head. Let it drip down their forehead and into their eyes and mouth. For added humiliation, make them leave it there indefinitely. Sissy sluts should always wear cum on their face and clothing when shopping or visiting friends.
There isn’t much that is more humiliating than having a condom filled with another man’s cum emptied over your head and into your hair
13- Pour full condoms onto their face
Have them lie on their back and pour a full condom onto their face so they get a facial. Have them open their mouth as well so they get the taste of it. Make sure if any spillage that, they get down and lick every single drop of it from the floor. If they miss a drop, then be sure to punish them properly. All sissies should get facials and become cum dumps or cum sluts; they should all wear cum on their faces at all times
Let all that spunk dribble down their face. Over their eyes, into their mouth and down their chin. Laugh at them as they gag when it runs into their mouth, and they taste it on their lips!
To add to the ordeal, make them rub it like moisturiser all over their face. Into their cheeks, their forehead and on their neck.
14- Blackmail them
Take photographs or demand they hand over personal information you can hold over them and threaten to expose them to the whole world unless they do exactly as they are told. I have so much fun with this one. The things these slutty whores and faggots will do just to keep you quiet. Get their pictures and videos, make them hold signs with their real name on them, you gave this then you can make them do almost anything for your silence
15- Financial domination
Take all their money. They don’t need it. Their only focus is on serving you, so just keep demanding more and more from them. Findom and sissy humiliation work well together, as making them hand over money while dressed is extremely degrading.
16- Post pictures of them online
If you have a website or blog, take their pictures, and post them for the whole world to see. Even more, fun when they start begging to have them taken down! Sissy exposure is another on the top of the list for me. To take pictures in degrading positions, dressed as slutty as possible holding a sissy exposure sign and having them watch you as you click to post it on all the top big sites with traffic.
The utter humiliation of having their pictures posted online will make your sissy’s heartbeat so fast it’ll feel like it’s going to burst. They will be willing to do almost anything to get you to take them down! Make sure to add humiliating captions, especially about them getting ready to suck a cock!
17- Make them wear a butt plug
They need to get used to having their ass filled, so shove a butt plug up their as and make them keep it there. To add to their humiliation, make them sit down and laugh as they do it gingerly.
Be sure to have them keep that plugin on their ass for a long time. Have them cum in a glass and pour it into their ass before plugging themselves for the ultimate act of degradation.
If you want to make it as humiliating as possible, get a butt plug that has a pink tail on the end and shove that in their arse and have them walk around with the tail wagging and shaking.
18- Shave off all their body hair
Make sure they are completely bald from the eyebrows down. Every single strand of body hair should be shaved off to be completely smooth.
Real men are covered in body hair, but sissies must be smooth and feminine at all times. They will be utterly humiliated as all their body hair is shaved off. Be sure to comment on how feminine they now look and laugh as they become smoother and smoother. For added humiliation, use wax on their thickest body hair parts.
You can also have them get a Brazilian on their pubic hair for that extra bit of degradation.
19- Make them keep a blog/Journal
Have them keep an online journal of their journey into sissification. It should include detailed accounts of their training and how they feel.
As humiliating as their journey into sissy hood and cock sucking may be, being forced to write it all down and relive it daily will be even worse. Be sure to insist they make a note of their feelings and how it makes them feel when they are dressed and looking like a slut
20- Cuckold them
Make them watch as you are with a real man. There is nothing more humiliating for a sissy than being dressed and having to watch their Mistress have sex.
This sissy wants you. Desires you. I would give anything to be in the real man’s position. so make sure you humiliate them as much as possible by forcing them to watch another man get their ultimate fantasy. You can keep their little sissy clitty locked in chastity so they can’t even enjoy an erection as they watch you in despair
21- Pimp them out
Make them go and suck or wank cocks for you. Make them earn for you by pimping them out to horny guys who just want an ass or mouth.
Make sure they are treated as nothing but a piece of fuck meat by guys who just want to use and abuse them. Make them feel like a commodity that you just use to fatten your bank balance and that you don’t care about how much they suffer.
22- Wear lockable high heels
Put high heel shoes on them and lock them on, so they have to wear them 24/7. Any woman will tell you how uncomfortable high heels are, so make your sissy wear them at all times.
Lock their feet into impossibly high stilettos or boots and then laugh at them as they struggle to walk and not fall over. Have them sleep in the locked-on boots so it’s very uncomfortable, and soon they’ll be begging you to take them off
23- Wear lockable clothes
Wearing sissy clothes is one thing, but to have them locked on and be unable to remove them without your permission will be extremely degrading. Snap that padlock shut and show them the key getting put in a safe place they can’t access so they know they are now completely owned and at your mercy, wearing locked-on sissy dresses and outfits
24- Administer a spanking
They will mess up at some point, so put them across your knee for a sound spanking. Giving a sissy spanking will remind them to do better in future.
25- Make them stand in the corner
If they anger or displease you, make them stand facing the corner for extended periods and ignore them. Even more humiliating if you give them corner time after a spanking. Corner time or naughty step time. Make them touch the wall with their nose and bottom pouted out, especially if it’s a freshly spanked bottom. They never get to know how long they will stand in this position.
Make them stand in the corner for hours while you walk around ignoring them and not caring how long they’ve been left there. Occasionally stop behind them, then giggle and walk away without saying a word!
26- Have them wear earmuffs in cold weather
A subtle yet highly humiliating act. Making them wear earmuffs in public will make them extremely self-conscious and feel humiliated and degraded as males don’t wear earmuffs. You can double up and make them go out sucking a dummy or wearing a nappy. The list is endless.
Earmuffs are an incredibly feminine thing. Men just don’t wear them, so get a big fluffy pink pair and make your sissy wear them outside at all times. When speaking with people within earshot, ask her loudly if she is glad to be wearing her friendly, warm earmuffs!
27- Make them serve all your friends
Have all your friends round for drinks and fun, and have your sissy serve them all night wearing their cute French maid’s outfit or shortest skirts and highest heels.
Have them totter about and your friends can either ignore them completely or laugh at them and make sarcastic comments at their expense. To make it worse for your sissy, give them impossibly high heels and a skirt so short it doesn’t cover their ass and exposes their clitty for all to see.
28-Make them serve all your real men lovers
Whenever you have a real man over and are relaxing before you go up to have sex, have sissy serve your lover his drinks and snacks. Have him curtsey and say thank you.
Having to serve a female is degrading enough, but being forced to serve another man is the ultimate humiliation for a sissy. Make it worse by insisting they call him “Sir” and thank him for satisfying you
29- Have them admire big cocks
Make them sit with a porno magazine or a porn site on a computer and make them admire all the big dicks. Have them comment on them and what makes them so attractive. Get sissy to rate them.
All sissies are incredibly jealous of real men with oversized cocks and wish with all their hearts they had a bigger one themselves, so it stands to reason you should make them admire these vast cocks and be made fully aware of their own “shortcomings”. Have them comment on how thick they are, how delicious they look and how amazing it must be to have a cock that size and girth.
Have them take notes and give a score out of 10 for each one
30- Make them get a Brazilian
Real men keep their pubic areas wild and grown while females keep theirs shaved or shaped, so why not embarrass sissy kins by having them get a Brazilian for their privates?
Real men just let their privates grow wild and don’t bother with grooming but make sure your sissy is always neatly groomed by forcing them to get a Brazilian. Even men who do groom down there wouldn’t get that design, so it’s perfect for humiliating a prissy sissy
31- Tuck their skirt into their knickers
Every woman’s worst nightmare and the most humiliating thing that can happen to them so why not make your sissy do it on purpose and then walk around like that? It’s bad enough to realise afterwards that it’s happened but imagine KNOWING that people can see!
They will be desperate to untuck and cover their embarrassment but make them walk around for ages like that. Even when their face burns crimson red with shame. To add to their embarrassment, give them a sound spanking just before you go out so their ass cheeks are still bright red when exposed, and everyone knows they’ve been spanked recently.
32- Feed them cum with every meal
Every time they eat, they take a full condom and empty the contents of their food. Ensure you do it with every meal, so they learn to appreciate the taste.
You can sit with a nice salad and put lovely salad dressing on it, so it’s nice and tasty but make them take that stale cum and pour it over their meal. Mix it in and watch as they gag and struggle. Mock the miserable look on their face as they long for something tasty but can only taste spunk
33- Make them beg to have their ass filled
Having a butt plug, dildo, or even a real cock up their ass is humiliating enough but add to it by making them beg to receive it. Even more, fun if they don’t want it!
Have them on their knees and make them beg and plead. Have them almost cry as they beg you to fill their ass and stretch their hole. Laugh at how pathetic they look as they beg for an ass fucking and how desperately they seem to want it!
34- Make them service real men
Have them on their knees and get them to give men blowjobs or hand jobs. Especially good at parties for entertainment or to keep male guests amused.
Nothing humiliates a sissy more than having to be near real men and their huge big cocks except making them service those big dicks! Have them give unlimited pleasure to real men and their thick dicks, and if you want to humiliate them further, have them comment about how glorious and beautiful each one is
35- Milk them
They don’t deserve orgasms like real men, so milk them by massaging their prostate to empty their balls. Especially effective for a sissy in chastity as they don’t even get unlocked for an orgasm.
Have them bend over and make THEM pull their cheeks apart so they can be milked to empty their balls. If you feel like making it more degrading for them, give them the prostate massager or dildo and make them do it themselves while you sit and flick through a magazine, not even acknowledging them
36- Make them do domestic chores
Have them do all the cooking, cleaning, ironing and tidying. Have a list of mundane chores and keep adding to them daily with punishment for not getting them all done.
Make sure it is the most basic and derogatory chore available. Hand wash your underwear, scrub the toilet (with a toothbrush if you feel like it!), and do all the cooking and cleaning. Hover over them, inspecting each task as they do it and reprimanding them if not done correctly.
37- Make them parade up and down
Have them walk up and down the room in front of you. Make their heels click on the floor and have them wiggle their ass.
Have them really mince up and down, thrusting their ass out and acting like a total hussy. Keep this up for ages
38- Make them pee sitting down
Extremely degrading for anyone with a penis but make them sit to pee every time. Having to sit down as a female will utterly humiliate them.
Real men pee standing up so making them sit down to do it will be incredibly degrading. Even having to put the seat down will be humiliating
39- Have them make a short video of themselves
This can be anything you want. A hookup site intro fully dressed and confessing to being a cum slut or just admitting what they do behind closed doors. Having to recite it will be embarrassing.
Make sure they are fully viewable and everyone can see them. Make them look like a total whore and have them state how much they want and need to be a total sissy bitch
40- Put a pink bow in their hair
Put a pretty pink bow in their hair that will make them self-conscious about how prominent it is for all to see.
41- Be your boyfriend’s fluffer
You like a hard dick but getting it there is a chore. Don’t worry, you have your very own sissy fluffer on hand to get them hard for you. Put sissy bitch to work getting the cocks hard for you
42- Make them swallow the contents of your lovers’ condoms
Either they do it themselves or you tip and squeeze the load out yourself but whichever way you choose to do it, having them swallow a load from a condom is pretty degrading
43- Sunbathe with a bra on
A degradation that will last for a long time afterwards! Make them sunbathe with a bra on then when they take it off they will have some lovely white bits to explain away!
44- Go out in public with subtle lipstick or makeup on
So subtle that it’s barely noticeable but to them, they will be extremely paranoid that everyone will know they are wearing lipstick
45- Make them wear lots of cheap, heavy make-up
Alternatively, plaster them in cheap makeup so they look ridiculous. Lots of lipstick, thick blusher, heavy eyeliner, the works
46- Make them wear lots of perfume
Spray lots of perfume on them so they smell girly and fresh. Something that will linger for a long time afterwards and have people asking questions!
47- Have them help get you dressed for dates
They are there to serve you so have them help you get dressed to go and meet real men. This is a job that all sissies should want to do
48- Hold your lover’s condom in their mouth
Take your lover’s used condom and make the sissy open their mouth. Put the condom in there and make them hold it while you both lie in bed relaxing
49- Wear women’s clothes under male clothing
While they will be completely hidden, your sissy bitch will be deeply humiliated at having to walk around wearing suspenders, pantyhose, a bra or whatever else you choose.
50- Make them swallow a real man’s load
As they get used to sucking on other men’s cocks, take things a stage further and have them swallow the man’s load of spunk when he cums. Right down their slutty throat
51- Wear a bright bra under a white shirt
One of the most humiliating things you can do. Put a bright red bra on them and then a white shirt and have them go to work and walk around in public with it clearly visible
52- Watch porn and have them act out all the female parts
Make them act out all the female parts of a porno clip. All the movements she makes, the voices, facial expressions, everything
53- Refer to them as female
Always refer to them as female. She, her etc. For any male sissy, this will be degrading as you refer to them as feminine
54- Answer the door fully dressed
When they are fully dressed in their sluttiest attire, make them answer the door. Either to your lover, a takeaway pizza, an Amazon delivery, or anything at all really s long as they get humiliated.
55- Have them dance to music
Put music on and have them dance for you. Whether it’s twerking, the macarena, the time warp or a nursery rhyme like I’m a little teapot. Laugh at them as they do it
56- Make them beg to suck cock
Make them get on their knees and beg you to suck cocks and make sure they REALLY beg for it. Begging, pleading and desperation in their voice to take a cock in their mouth
57- Make them wear a vibrating butt plug you control
There are lots of app-controlled butt plugs out there. Have them purchase one and give you control over it so you can send random vibrations to their ass whenever you feel the mood
58- Wear massive high heel shoes
Like REALLY massive heels. Huge 7-inch stilettos that they struggle to walk in. Giggle and make fun of them as they totter around, struggling to stay upright and not fall over
59- Have them wear a pink collar
Being collared is humiliating enough but a bright pink one? Emblazoned with the words “Sissy Bitch” on it? For added effect, lock it on so they can’t take it off, ever
60- Subject them to ass inspections
Regularly have them bend over for an inspection to make sure their ass is filled, and clean for the next cock or to see how the stretching exercises are coming along.
There you go. 60 ways to humiliate a sissy. Obviously, some will be too far while others may seem tame. It depends on where your experience level is with regard to how far you wish to go.
Of course, you may not have a choice. If you are a submissive sissy who has a Mistress trying to find the most humiliating tasks possible for you then you may be in for a rough ride!
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