Humiliating a Sissy

[RacyWilde]

*

I need to expand my repertoire in humiliating a sissy. I'm looking for creative and innovative ideas to use in my real life sessions.

I am aware that everyone is humiliated by different things - I'm just looking for examples to get ideas flowing :-

Physically - I know that having him on his back for different things such as pegging help take his masculinity. Are their any other physical positions, or bondage positions that compromise masculine confidence?

He loves wearing pretty girlie clothes such as school girl outfits - but that's the thing... he loves it. What are some outfits that humiliate? Or should I do stuff like smear his pretty make-up or draw a cock on his face and show him in the mirror?

Verbally - this is my weakness. I'm not a verbal person and I get lost for words. Do you have any harsh and unforgiving words or phrases (I'll try to memorise them for quick use)? But is it more about how you say the words than the actual words themselves? I know how to get heavily mean with my voice but I want to make sure that what I say will turn him on rather than destroy him.

Cuckold - are there any scenarios that strongly belittle or humiliate? I know that having sex over his face probably works, and getting the other guy to cum on him, but what other powerful images/positions can be effective?

Also, how do you humiliate him via his cock when his cock is actually pretty groovy?


Any advice is much appreciated.

 

[cripple92996]

['[p

One verbal idea is to speak in non full sentences, like she is too stupid to grasp what you mean!

 

[RacyWilde]

One verbal idea is to speak in non full sentences, like she is too stupid to grasp what you mean!

Actually, I'm really good at training dogs. And it would be kind of fun commanding him in Norwegian. I won't tell him what the words mean... he has to work it out by trial and error. And when he gets it wrong, I get to spank him!!!

Ned! Tigg! Rumpe! Stille! Hysj!

Hahaha!

 

[RacyWilde]

*

I have gotten some great advice via PM... Thank you (Though, I think it would be fun to have an open convo about stuff so others can join in too )

 

[DomPeter]

force him to wear very girly clothes/outfits- very short skirts with an anal plug and cock cage. Make him repeat over and over that he wants to please cock- maybe in Norwegian !

 

[default24]

Do something that forces him to be public about it. Have him take a pic of himself dressed up outside. If that's too far, have him randomly PM somebody to tell them that he likes being a sissy. Have him send screenshots of the results

 

[yukonnights]

*

I need to expand my repertoire in humiliating a sissy. I'm looking for creative and innovative ideas to use in my real life sessions.

I am aware that everyone is humiliated by different things - I'm just looking for examples to get ideas flowing :-

Physically - I know that having him on his back for different things such as pegging help take his masculinity. Are their any other physical positions, or bondage positions that compromise masculine confidence?

He loves wearing pretty girlie clothes such as school girl outfits - but that's the thing... he loves it. What are some outfits that humiliate? Or should I do stuff like smear his pretty make-up or draw a cock on his face and show him in the mirror?

Verbally - this is my weakness. I'm not a verbal person and I get lost for words. Do you have any harsh and unforgiving words or phrases (I'll try to memorise them for quick use)? But is it more about how you say the words than the actual words themselves? I know how to get heavily mean with my voice but I want to make sure that what I say will turn him on rather than destroy him.

Cuckhold - are there any scenarios that strongly belittle or humiliate? I know that having sex over his face probably works, and getting the other guy to cum on him, but what other powerful images/positions can be effective?

Also, how do you humiliate him via his cock when his cock is actually pretty groovy?


Any advice is much appreciated.

This probably isn't really BDSM per se, and might get better feedback on the Fetishes Forum...but since you asked, here's a couple of thoughts.

The goal is to humiliate, so I think it's good to remember that humiliation is part of his "reward"..if not the majority of it. For example, he probably wears the 'girlie clothes' because it humiliates him to do so. So to take them away would be more of a punishment than humiliation. Thus, you can increase that humiliation with derogatory comments...I never thought I'd end up with a panty wearing sissy...or, that dress makes you look so weak, I think I need a real man for a change...you might consider an anal plug with a furry tail...I don't know if smearing his make-up would be humiliating or more like rejection/punishment.

Physical positions that should be humiliating might include; any manner in which his cock/balls are vulnerable to either physical or derogatory attention...on his knees, especially before another man (since you mentioned the cuckold play I'm assuming there is another man)...pose him in a way where he can see himself in a mirror, then ask him if this looks like a man, (you mentioned pegging him, so make him witness it so he can see he is no longer a man, etc)...put a rope leash around his exposed cock/balls and lead him where you will...he must always sit to pee and anyone is free to watch....(and speaking of pee, you could consider taking control of when he gets to sit a 'tinkle' and just hope you don't get so busy he wets his panties.)

Cuckold stuff; What you said is good. Things that may or may not be on the table might include him servicing the other man sexually. This gets touchy, but it's an option if everyone is open to bisexuality. Another thought is to deny him any participation at all 'since your "man" doesn't want the pathetic cuck around him'. If your "man" is open to the cuck being involved, then being required to serve the other man is a way to strip some male pride from the cuck...e.g. drinks, snacks, take his shoes/socks off and wash his feet, etc.

As to the "groovy" cock; perhaps just some comments like; what a waste of a perfectly good cock...who would have thought someone with a normal dick would turn out to be such a sissy wimp...you should donate that thing to someone who could use it...etc.

In regard to using your "mean voice"; Just try to always remember that it is the gift of humiliation that you are trying to give him. If a "mean command" shames him, then it is useful to the game...if it breaks the erotic tension, then it probably isn't useful. And like all BDSM/humiliation games, I think it is important to remember to provide loving after care to the sub who has been drained and taken to the limits of his emotions...it's all for fun and love shared.

Have Fun

 

[RacyWilde]

This probably isn't really BDSM per se, and might get better feedback on the Fetishes Forum...but since you asked, here's a couple of thoughts.

The goal is to humiliate, so I think it's good to remember that humiliation is part of his "reward"..if not the majority of it. For example, he probably wears the 'girlie clothes' because it humiliates him to do so. So to take them away would be more of a punishment than humiliation. Thus, you can increase that humiliation with derogatory comments...I never thought I'd end up with a panty wearing sissy...or, that dress makes you look so weak, I think I need a real man for a change...you might consider an anal plug with a furry tail...I don't know if smearing his make-up would be humiliating or more like rejection/punishment.

Physical positions that should be humiliating might include; any manner in which his cock/balls are vulnerable to either physical or derogatory attention...on his knees, especially before another man (since you mentioned the cuckold play I'm assuming there is another man)...pose him in a way where he can see himself in a mirror, then ask him if this looks like a man, (you mentioned pegging him, so make him witness it so he can see he is no longer a man, etc)...put a rope leash around his exposed cock/balls and lead him where you will...he must always sit to pee and anyone is free to watch....(and speaking of pee, you could consider taking control of when he gets to sit a 'tinkle' and just hope you don't get so busy he wets his panties.)

Cuckold stuff; What you said is good. Things that may or may not be on the table might include him servicing the other man sexually. This gets touchy, but it's an option if everyone is open to bisexuality. Another thought is to deny him any participation at all 'since your "man" doesn't want the pathetic cuck around him'. If your "man" is open to the cuck being involved, then being required to serve the other man is a way to strip some male pride from the cuck...e.g. drinks, snacks, take his shoes/socks off and wash his feet, etc.

As to the "groovy" cock; perhaps just some comments like; what a waste of a perfectly good cock...who would have thought someone with a normal dick would turn out to be such a sissy wimp...you should donate that thing to someone who could use it...etc.

In regard to using your "mean voice"; Just try to always remember that it is the gift of humiliation that you are trying to give him. If a "mean command" shames him, then it is useful to the game...if it breaks the erotic tension, then it probably isn't useful. And like all BDSM/humiliation games, I think it is important to remember to provide loving after care to the sub who has been drained and taken to the limits of his emotions...it's all for fun and love shared.

Have Fun

Thank you so much!

For at least one play session, I do plan to take him to a dungeon or play space. I'm in contact with a rigger (as I don't have the skills as yet to suspend him) and I plan for this male rigger to tie him up facing down spread eagle. I'll wrap him leaving his balls and cock to hang and to have easy access between his legs. I was also thinking of making him deep throat my strap-on and then forced ejaculation to collect for a fake cock. Then I'd peg his ass ejaculating his own cum into it.

 

[RacyWilde]

force him to wear very girly clothes/outfits- very short skirts with an anal plug and cock cage. Make him repeat over and over that he wants to please cock- maybe in Norwegian !

Cock cage... I never knew the term for them. They are sooo pretty! It would be so cool if I cold find one with diamontes so he sparkles!

Do something that forces him to be public about it. Have him take a pic of himself dressed up outside. If that's too far, have him randomly PM somebody to tell them that he likes being a sissy. Have him send screenshots of the results

Yeah, I was actually thinking of starting a blog just for our adventures. But, it might turn out to be a reward... He'll probably enjoy my attention taking his picture and then displaying him.

He does like pretty things though - I've got tutus and feather boas and pom poms for him... (me being a dancer, he'd love to wear all my costumes...lol) but I also have a spider monkey costume. I could make him wear it (it's lovely and furry) and then tan his ass as red as a baboon's. I've also got a real WWII german gas mask. I could make him squat naked in the corner with the mask on when he is naughty. Now that would be a gorgeous photo op!!!

 

[Blue]

I've also got a real WWII german gas mask. I could make him squat naked in the corner with the mask on when he is naughty. Now that would be a gorgeous photo op!!!

Better not, those things use asbestos as a filter. Shouldn't really be worn at all, certainly not for long durations.

 

[default24]

Yeah, I was actually thinking of starting a blog just for our adventures. But, it might turn out to be a reward... He'll probably enjoy my attention taking his picture and then displaying him.

Maybe you should do it anyway? Just don't tell him...

 

[RacyWilde]

Better not, those things use asbestos as a filter. Shouldn't really be worn at all, certainly not for long durations.

It doesn't have the filter

 

[RacyWilde]

Maybe you should do it anyway? Just don't tell him...

- You're so naughty encouraging me!!! Actually, a handful of people have asked me to do it...lol.

 

[default24]

So, how do you feel about giving in to peer pressure then?

 

[Nezhul]

Are their any other physical positions, or bondage positions that compromise masculine confidence?

Kneeling, bending over something.
Simple stuff like holding hands behind his back or on top of his head.

As for bondage - I would imagine that any bondage is degrading and humiliating a bit, and it takes away control and power, so it takes away one of the bases of masculinity. Any position that leaves him looking stupid or vulnerable will do. Standing on his toes, ass hooks, etc.

One simple bondage idea for men (not only sissies) that I've seen is having a rope tied to the genitalia (google how to fix it securely but safely), and then either tied to a heavy object or looped through some kind of fixing point on the wall and back to your hands. The idea is you sitting in front of him, just out of his reach, and taunting him with how he should eat your pussy, but he can't reach it because the rope pulls on his balls.

Chastity can also be considered bondage.

He loves wearing pretty girlie clothes such as school girl outfits - but that's the thing... he loves it. What are some outfits that humiliate? Or should I do stuff like smear his pretty make-up or draw a cock on his face and show him in the mirror?

Well if he likes it - then perhaps you can't really do something sissy-oriented with outfits.
What you can do is verbally humiliate him for that, ridicule him for what he's wearing, if he has an erection while wearing panties - that it looks stupid.
But verbal is a different point.

What you could also do is apply makeup to him yourself, making him too painted-up and looking like a cheap whore or something.

Verbally - this is my weakness. I'm not a verbal person and I get lost for words. Do you have any harsh and unforgiving words or phrases (I'll try to memorise them for quick use)? But is it more about how you say the words than the actual words themselves? I know how to get heavily mean with my voice but I want to make sure that what I say will turn him on rather than destroy him.

Well, first as I said if you want humiliation - then the best way to do is ridicule him for what he's wearing, for how this makes him less than a man.
Contrast him with yourself, how similar clothes look gorgeous on you, and how stupid he looks in comparison. That's the route I'd go, but you need to actually gauge his reactions to see what works.

I will say outright that I don't like "bratty" or "mean bitch" impersonations, especially when they are made-up and forced.
I much prefer gentle femdom, when a girl is talking in a soft voice, smiling, cooing lovingly in my ear. But she does say things that are mean or humiliating. The dissonance between voice and content is what gets me going.
"I'm going to hurt you" - has so much more impact when it is said lovingly, with audible care in the voice.

I also dislike swearing. It's an instant turn-off for me.

I would concentrate on pointing out how silly he looks than on calling him names.

But this all - is my preference. Again, you will need to gauge his reactions and see what's working for you.

Cuckhold - are there any scenarios that strongly belittle or humiliate? I know that having sex over his face probably works, and getting the other guy to cum on him, but what other powerful images/positions can be effective?

I'm not really into that thing, but as far as I understand - cuckolding is basically withholding sex from him, downplaying his ability to please you as a man, demonstrating how other "real" men are superior to him, and reducing his role in the sexual act to that of the observer or support agent (cleaning your pussy after you are fucked, sucking your tits but not having any chance at your pussy, etc).

I may be wrong here, again it's not my fetish, but you can cuckold with vibrators and dildoes. Taunting him that toys will satisfy you better than him. It doesn't mean you don't have sex in the end - you may let him fuck you eventually, but the idea is to downplay his performance or brushing it off to chance.
"I'm surprised you even can do that well" - this sort of attitude.
"Do you think you can please me? A pathetic sissy like you?"

Also, how do you humiliate him via his cock when his cock is actually pretty groovy?

Play on the dissonance with him having a cock in the first place and dressing up as a girly-girl. That he only gets hard if he is humiliated. Something like that.

I will also add one more paragraph to your points. Mental.
Reinforce the image that he is. He's a wannabe-girl, a sissy. That means that he's not your boyfriend, not a man, not a stud. He's your girlfriend in bed at most. Try to treat him as such, and ridicule him for wanting to fuck you. That it wouldn't be proper to fuck another girl, that you are interested in men with big hard cocks, not sissy sluts.
Point out that he's inferior to you because he doesn't have boobs, or that his waistline is wrong, or whatever works for you. Compare yourself to him, how you are better in every respect.

 

[Nezhul]

Better not, those things use asbestos as a filter. Shouldn't really be worn at all, certainly not for long durations.

As far as I know, you can take the filter off. That way it turns into a rubber hood with a hole for air - no asbestos.

They are a bitch to put on and take off though - I know because I have hands-on experience with russian WWII gas masks.


Also I see things like blogs and going public discussed here.
Be very careful with those. In our society exposure of such fetishes can ruin careers and lives, sadly.
If you do the blog, take care to hide his face and personality, so that nothing can be linked to him.
If you go public, make sure that only the two of you know what's going on. Like for example him secretly wearing panties, or something. First, involving bystanders is rude to them and can get you into trouble with law. Second, again, keeping the persona behind the panties hidden is essential. Privacy is a treasure.

 

[mickyp123]

..........

 

[Nezhul]

weirding out the poor shop assistant is not a good thing. So I wouldn't involve her in decision-making.

He could ask her other questions though, like which one she thinks is more girly. Not telling her it's for him. Answering that - is her direct job. But I don't like the idea of actually making her uncomfortable by asking what would suit HIM. How can she know? Chances are she's not into such fetish and will be creeped out immensely.

 

[RacyWilde]

So, how do you feel about giving in to peer pressure then?

lol - Yes, I think it would be interesting for people to see how a switch operates. Sometimes being a switch seems taboo (I get the feeling that some people think the true switch is a myth...lol). But during a two week period I'll have both dominant and submissive men to play with... I'll be switching from Dungeon Domme to sub to Mistress to pet to Femdom to slut... I'm certainly going to be extending myself!

 

[RacyWilde]

One simple bondage idea for men (not only sissies) that I've seen is having a rope tied to the genitalia (google how to fix it securely but safely), and then either tied to a heavy object or looped through some kind of fixing point on the wall and back to your hands. The idea is you sitting in front of him, just out of his reach, and taunting him with how he should eat your pussy, but he can't reach it because the rope pulls on his balls.

I really love this idea!!!

What you could also do is apply makeup to him yourself, making him too painted-up and looking like a cheap whore or something.

Yeah, I'm too good at make up...lol. I was going to turn him into The Black Swan - he would probably love the costume... but I'd humiliate him by making him stand in ballet poses... make him sauté (jump) without any without any panties on. (He's a very fit guy - plays football - so... lol)

I will say outright that I don't like "bratty" or "mean bitch" impersonations, especially when they are made-up and forced.
I much prefer gentle femdom, when a girl is talking in a soft voice, smiling, cooing lovingly in my ear. But she does say things that are mean or humiliating. The dissonance between voice and content is what gets me going.

I know... the thing is... I consider myself a Gentle Femdom. I almost wince every time I have to insult or use swear words on people. It feels like an act of anger and I don't want to bring that into my sessions. Really, I would much rather be a strong female and treat him like a baby girl... but he needs the insults, so I'm trying to extend myself for him. But yeah, I think I'll try 'lovingly threats' cooed into his ear.

I'm not really into that thing, but as far as I understand - cuckolding is basically withholding sex from him, downplaying his ability to please you as a man, demonstrating how other "real" men are superior to him, and reducing his role in the sexual act to that of the observer or support agent (cleaning your pussy after you are fucked, sucking your tits but not having any chance at your pussy, etc).

I thought about it - I think I'll be bringing in other guys as it will be for intense my sissy. He's not bi but I'm sure him having to service the other men, he'll feel the humiliation.

I will also add one more paragraph to your points. Mental.
Reinforce the image that he is. He's a wannabe-girl, a sissy. That means that he's not your boyfriend, not a man, not a stud. He's your girlfriend in bed at most. Try to treat him as such, and ridicule him for wanting to fuck you. That it wouldn't be proper to fuck another girl, that you are interested in men with big hard cocks, not sissy sluts.

I was actually thinking of not allowing him to have sex with me at all... getting him to the point of primal but denying him, and I'd let another man take instead right in front of him. I'll touch my sissy and pleasure him... but he won't be allowed to touch and pleasure me at all. Sissies want to please, and if he can't please... if I don't allow him to... perhaps that can be a stronger way of insulting him. Though, it is much crueler as it will effect his self esteem. I'll have to be careful that I don't reject him too much - just enough to initiate the primal.

Also I see things like blogs and going public discussed here.
If you do the blog, take care to hide his face and personality, so that nothing can be linked to him.

Oh, most definitely!! I'm very careful to keep my sex life and daily life separate. I don't do faces at all.

Thank you so much for your input, I really appreciate it.

 

[SissySalina]

May a sissy ask a question.
Is this person a sissy or just someone imitating a sissy?

 

[RacyWilde]

May a sissy ask a question.
Is this person a sissy or just someone imitating a sissy?

He's discovering himself as a sissy. He is fairly young too. So we are trying to work out our groove.

 

[SissySalina]

He's discovering himself as a sissy. He is fairly young too. So we are trying to work out our groove.

Thank you for answering, Sissy Salina is a sissy and proud of it, it is almost impossible to humiliate Sissy Salina.
If he is just discovering sissydom then the best thing would be to take the sissy out in public. Find a nice day and go to a park or some other place in public with sissy all dressed up. You may think this will not be humiliating but if sissy is just starting it should. He may experiment in private or around you but not in public. The first few times a sissy is in public all kinds of things go through their mind and being around people that they do not know should provide with some humiliation.

 

[Maidboy]

How about having a dominatrix be his "babysitter" while you go out on a date? Give him strict orders to obey her as he would you while you're away, and have her make a list of his transgressions (real or imagined) for him to be punished for upon your return. "Mistress Babysitter" could supervise his dressing up and make him prance around to show her what a good little girl you've made him.

Upon your return, you could tell him about your date and punish him after Mistress Babysitter checks off the list of his transgressions. You could also apply a tassled butt-plug to his sissy ass and have him prance around for your Ladyships' amusement. His reward for being a good girl would be a good pegging from both of you. Just a thought for your consideration...

 

[RacyWilde]

Thank you for answering, Sissy Salina is a sissy and proud of it, it is almost impossible to humiliate Sissy Salina.
If he is just discovering sissydom then the best thing would be to take the sissy out in public. Find a nice day and go to a park or some other place in public with sissy all dressed up. You may think this will not be humiliating but if sissy is just starting it should. He may experiment in private or around you but not in public. The first few times a sissy is in public all kinds of things go through their mind and being around people that they do not know should provide with some humiliation.

Yes, I think going out in public is a very good idea. I will be taking him to a dungeon - though, he wants to be discreet there. Maybe I can demand he dresses up for the occasion for me. I do have a nice little black tutu I want him to wear for a Black Swan look. (I work in the theatre so I like my girls to have a vaux de ville style).

Thanks