Sunday, April 21, 2013

Ask Boot: How to handle a pouty sissy

Dear Boot: I am having trouble with my sissy maid Emily. She likes to dress as a woman, attend events, and unlike most sissy maids, she does not like being called a boy (even when in boy's dress for work). She is poor to useless at her maid duties, but she pouts and sulks a lot when told off. I've kept her boy-clit in a cage for 7 months, but nothing seems to be working. How do I humiliate her?

Well, there's a lot of question there. And, I think, there's a problem with how you refer to her. I'm not entirely sure that Emily is a sissy.

What do you mean?


Well, a sissy tends to be someone genetically male who is dressed as and treated as an extremely (even ridiculously) feminine less-than-person. It's about degradation, humiliation, and taking someone who might once have seen themselves as masculine and breaking them down into complete slavery, often by using that feeling of masculinity against them.

It's like small penis humiliation. Some men do have a small penis. And some men have a large penis. Some have an average sized one. And the truth of the matter is that it's all luck of the draw. But the size of the penis doesn't actually have anything to do with small penis humiliation.

It doesn't? That seems wrong. I mean, it's called small penis humiliation. Doesn't that kind of require a small penis?

No. You see, the important part there is the humiliation. It doesn't matter if the person has a small penis or a large one. What matters is that he is proud of, or at least acutely conscious about, the actual size of his penis. If calling it small is just stating a fact, and one that he has accepted, then it's no more humiliating than it would be to tell me that my name rhymes with 'boobs.' It's just how it is. In order for the size of his penis to have any impact on humiliation, he has to be uncertain. He has to either have no idea if it is big or not, or he has to worry that it's too small and think that people will make fun of him for that small size. The humiliation comes from fulfilling that fear and fantasy, or from taking something he's proud of and telling him that he not only shouldn't be proud of it, but rather that he should be ashamed of it.

What does this have to do with Emily?

Well, if Emily is accepting of herself as a woman, if she thinks of herself as Emily rather than, say, Steve (or whatever the name on her birth certificate may be), then it isn't humiliating to call her feminine. It's not humiliating to say she's effeminate, and it's not humiliating to call her girly. These are things that she sees as facts. Or even as preferences. She might even be proud of being girly. You can't make fun of someone for something they are proud of, something they take as a compliment. No bully ever successfully made someone cry through compliments. Emily, it seems, likes being a sissy.

But she's a bad maid.

Yes she is. And from the sound of it, that doesn't bother her. She isn't interested in being a maid. That's why she's no good at it. And why she pouts when you yell at her for being bad at it.

So what do I do?

It's a tough question. The trick to it, the trick to any humiliation, is to go after the things they are proud of. To tell someone that what they enjoy is wrong, that it's something they should be ashamed of. Basically, you're trying to build a humiliation loop. Make her feel bad about something she likes, then make her feel bad that she enjoys feeling bad about it.

That's all well and good, but you're not really answering my questions. Don't make me hurt you.

Okay, okay. Just put the whip down... for now. Let me see if I can get at what you need. Does Emily think she passes as a woman? She likes being called Emily when in her boy clothes. Does she like being called Emily publicly? Maybe she should have a name tag at her job that says Emily. Or something on her desk. Of course, that involves the public without consent... so maybe not.

Seriously, Boot. I'm going to hurt you.

I'm thinking, I'm thinking. Maybe the problem is that Emily doesn't actually like humiliation; maybe she just doesn't respond to it all that well. You said she pouts when she is scolded. So scolding isn't an effective punishment. You need one that will work better. And I have an idea. I recommend an invisible fence.

What, like for dogs?

Exactly. You put the invisible fence in the room or rooms that Emily is allowed to be in, the ones she is supposed to clean. But you leave one corner of one of the rooms outside the fence. And so if she goes into that corner, her collar will shock her. You show her this, then tell her to clean up. And tell her that if she doesn't do a good job, not only will you yell at her, but you will also make her sit in the corner. Maybe the pain will convince her.

Or maybe the way to get at her is to go backwards. If she's proud of being feminine, tell her that she makes an ugly woman. Tell her that it's obvious that she's a man. Call her by her male name if she doesn't do as she's told. Don't let her shave. Remind her that she'll be the bearded lady. Tell her that you'll still make her serve, make her dress up, but you won't let her shave unless she does a good job and proves that she's a good sissy.

Basically, if she likes being a sissy, you take that away from her until she does what you want. Until she admits either that she likes being a sissy, or (if she already admits that), you make her admit that no one is fooled and that she will never pass as a woman. Everyone knows that she's a man, and no amount of makeup, girly clothing, or practice will ever change that. Then remind her that since she isn't doing what she's supposed to, since she's growing out facial hair, it's her choice that makes sure she won't pass as a woman. That she is making it happen. And then point out that she likes that, she likes that no one will ever think she passes. And then you have your humiliation loop.

Okay, not bad.

So you're not going to whip me?

Is that disappointment I hear? Did you want me to whip you?

Hey, Emily's not the only submissive out there, you know.

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