MY IDEAL SISSY
from Rebecca

Dear Helga,

I'd like to follow up on your question of what my ideal sissy slave would be like, and what I would have them do when serving me. I tried to show some restraint with my answer, so you'll have to believe me when I say I think I succeeded.

While I know it would be much easier for me to get what I want by seeking out a male with sissy proclivities, I would actually prefer to take the harder road and sissify a male who doesn't actually secretly want to be a sissy. I guess there's just something sort of exciting about entirely transforming a "manly man" who assumes his life is going to go a specific way, and then basically rewriting his fate from the ground up into one that he won't enjoy, and certainly would never choose for himself. Gradually cancelling out all his other life prospects would be part of the fun, to be in control of that, trying my best to get him into a position where he will eventually realise that he has no other options anymore in life, his only option is to be a sissy. By cancelling out all his other options and freedoms, and having him do all the boring things that take so much time out of the day, he will will effectively be opening up my life options and freedoms. I enjoy thinking that he's out there right now, somewhere, happily going about his day, with no idea that some time down the line he will spend his days doing his level best to be a she.

While it's probably a lot to ask in reality, if we're talking fantasies, then I want to turn an arrogant, confident, selfish man into the exact opposite, and for him to become not just submissive to me, but entirely reliant on me. I want to lead him down a path he won't be able to find his way back from. I love the thought of keeping him immersed in a constant state of humiliation or apprehension. There's something very powerful about that.

Since I want to target an ordinary male, I know my transformation will certainly be more difficult or more gradual than some of the methods expressed by some mistresses in the letters on your site, some of who are fortunate enough to have a number of like-minded friends to outnumber the victim in question, or physically forcing him into dresses. Currently, I won't have any such help available, but that's okay. Strangely enough, I am actually looking forward to the struggle, to see if I can get by using guile and wits to lure him into his new lifestyle. There are a few obvious ways, like using sexuality to get what I want or making sexy bets where we each get to choose a forfeit (which could potentially be a good way of finding out what he finds sexy too, which could be used to my advantage at a later date) but even then, finding ways to escalate things from these initial gambits and pushing them forward into a more serious area will prove tricky without him realising what I'm doing, and may require resorting to more blunt tactics such as blackmail. But either way, it's a challenge I will enjoy. He will be my project, and it will be so much more rewarding seeing his gradual decline.

As for practicalities, I know that some women prefer their sissies to not wear a wig or maybe even encourage them to grow facial hair so that the sissy is always reminded that they are a man in a dress. But I prefer sissies to be hyper-feminine. They're unlikely to forget their embarrassing situation, and I don't want a man in a dress, I want a sissy. If they are to act the part, then they should look the part (plus they look so cute when they're properly done up). I want him to mince about in satin, lace and pink frills (I prefer the delicate, girly-girl look over the latex-style sissy clothes. I want a dress short enough that they can't hide their panties no matter how much they pull it down). While an abundance of frills and petticoats may be less practical for the role of a maid, practicality won't be my problem, it will be his.

I would love to train him into developing his own girly regime that he will follow to the letter and be properly inspected on. Make-up, nail polish/acrylics, outfit, shaving, perfume, moisturising after baths will all fall under my scrutiny. Failure to adhere to my standards will of course mean punishment. I will definitely have him wear a wig, but I do love the idea of a sissy in big hair rollers, too.

Speaking of punishments, since I have no experience with this sort of thing, I would obviously start out attempting what I have enjoyed reading. For painful punishments, I enjoy the idea of blindfolding and gagging a naked sissy whose hands are ideally tied from the ceiling, so I'd have access to their entire body. I would then spend a long time making them uncomfortable. Start out tickling then work up from there to keep anticipation going, putting clothes pegs on sensitive areas like nipples, the backs of upper arms etc. some sort of mild electric shock, building up to a proper caning. For more psychological punishments, I love written lines or secretarial typing challenges (i.e. how many times can they type a certain embarrassing phrase in a certain length of time) and I love teasing. I know it's simple, but I love the impact words can have on the human mind, so I enjoy the prospect of bringing a sissy to tears just through the power of words alone.

I would enforce chastity (making him wear smaller ones for punishments, and then purposely excite him) and try my best to avoid allowing him to have a proper orgasm by milking his prostate regularly. I understand from reading PDQ letters that this is the best way to keep sissies healthy downstairs without giving them any pleasure, so I'd have to learn how to do it. I'd pretend that if he did as he was told then he would be allowed to have a proper orgasm, but if he is being properly milked then there's no need, so why would I allow it? I also wrote down an idea for when the sissy has spoken out of turn-I would strip them to their high heels, gag them and then tie little sleigh bells to the sissy's chastity, so that the only way they could communicate would be one shake for "yes" and two for "no". I thought a sissy would be unlikely to answer back in future if they knew they could communicate with me after that would be shaking their little dolly for me.

I would teach her to do the cooking and cleaning, to bathe, dress me and do my hair, and would have her learn new things, so her brain wouldn't have time to think of anything other than her duties (learning things like massage, aromatherapy, perhaps have her learn how to cook a new dish a week, maybe even learn an instrument or how to striptease for me) and I would remove all forms of stimulus, like TV, radio, internet and I would choose which books she could read, but even then they will just be reference books that can help her in her training, no reading for entertainment. She would have no time or need for that sort of thing.

I thought I could go round after she has cleaned, wearing white latex gloves and drag my fingers over the work surfaces, skirting boards, toilet, behind furniture etc. to see if she's done her job well. I will then tell the sissy that if she sucks the latex fingers clean, it will put an end to her cleaning duties, but if she chooses not to suck them, then she must go back to work. If she has done her job properly then she won't have anything to worry about. I originally wrote down in my book that I could do this with a dildo instead of a latex glove, because I liked the idea of him sucking a dildo to signal the end of his cleaning duties, and have the sissy actually looking forward to sucking it clean because it meant their work was over, but a latex glove is probably more practical for this particular indignity.

I would take her clothes shopping with me (she would have the correct underwear on under her male clothes. I'm not a fan of public exposure, but he doesn't have to know that) and maybe have her pay at the checkout for certain items, or put certain clothes up against her in the store to make her feel uncomfortable. Since I currently have no like-minded friends (to my knowledge anyway) then I'd have her wait for me while I had my hair cut in the salon. I thought an all-female environment would be a great substitute while he sits uncomfortably, knowing he is wearing panties underneath his clothes, and will no doubt be asked by the hairdresser to appraise my final look. There will definitely be opportunities to demonstrate to the other ladies how well-trained he is, and add another element to his humiliation.

He will be taught to mince, curtsey and speak in a softer, perhaps higher register. I want to wait as long as possible before bestowing him with a new female name. I have a page in my notebook devoted to names that I like for a sissy (including some silly surnames, like "Pinkbottom" or "Pinny-Tailor". I'm not sure if I'll go as far as to give my sissy a unique surname as well, but it's still fun to come up with this stuff) and I feel that a new name after such a length of time would solidify a new identity in his mind, so I can turn it into a bit of a special and embarrassing occasion for the male. Up until this point, I will refer to him only as sissy or bitch or the like, but I will make sure that her new name will represent a humiliating turning point in her training, to remind her that she has reached a certain level of success in her femininity and servitude that she has earned her new name. I will make sure it is something she has worked hard towards, and I will remind her that she should respond to it with pride. I will have her invent and practice her new signature, too. Get her used to writing out her new name.

In short, you can probably tell, I love a man in a predicament. I had a lot of fun writing this, it was quite cathartic, so thank you for giving me the opportunity.

Once I've buckled down, got the grades I want and have found employment somewhere, then I'll be free to begin my search.

Kind regards,
Rebecca


Thank you for your letter Rebecca. What a great plan and so well thought out, I have no doubt you will succeed. I certainly appreciate the concept of training an otherwise normal male, the journey is part of the pleasure, not only that, but since there would be no preconceived fantasies on his part your training could be to your ideal then of course there will be great satisfaction when she is serving you perfectly.

I must say that I love the idea of keeping a book in which to formulate your desires and plans, a large to do list of sorts, really cool.

Helga

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