It is key to understand the mind of a Sissy Boy to make this experience satisfying for the both of you. Im going to just write down what I learned so far so you can use it to your own advantage. At the heart of every sissy’s psyche is a need for sexual humiliation. They are most aroused by acts, words, and situations that are unpleasant and degrading. One part of them is irresistibly drawn to things that another part of them finds very distasteful.
For most people, the biggest initial hurdle to overcome is a sense of guilt as you learn to interact with her. It’s hard not to feel a little bad as you relax on the couch while she works diligently at scrubbing your bathroom; especially since she gets no tangible reward whatsoever for her efforts. But the key here to remember is that while she is not receiving any payment or physical reward, you are giving her something infinitely greater; something that she could never obtain on her own.
This leads into a key question…what exactly does she want?
And here lies a problem. For most sissies, explicitly telling you exactly how they would like to be treated will make the relationship feel as if they are in control; that they are calling the shots. They need you to be in control at all times. But in all this, don’t bend too far to try and appease their fantasies. Fundamentally, this is about you and what you enjoy. Their entire role is to be relegated to being a servant whose sole function is to attend to you and make your life pleasant.
1. Sissies are not men
At least not real men. They failed as men and thats why they are our sissy boys. Never forget to mention this at least once a day ('you're such a pathetic excuse for a man', 'you make a better girl then a man by a mile', 'you're such a sissy!'). It's important for his state of mind that you keep this up; don't try to make her be something she just isn't meant to be. Because they are not men, they do not have cocks, they have a clit and a sissy pussy.
2. Sissies need to train to satisfy men
Most sissies would consider themselves at least mostly heterosexual, and in general are less attracted to men than to women. However, the very fact that they find sexual acts with men undesirable or possibly degrading also makes those acts very arousing because of the humiliation they entail. Even though he may never really do it, you need to keep reminding him when he sucks your strapon or practices his blow job techniques on a dildo that he is preparing to suck real cock.
When you fuck him, you tell him how pathetic he is and that he needs to try harder to satisfy real men. When he walks, tell him to sway his hips because men like it. This is all strongly related to the 1.): as he is no real men and cant pleasure you (a real woman) he should just practice to please men because ultimately thats all he's good for.
3. Make him ever more feminine
This is important but it also takes time. He will need a proper wardrobe and will need to maintain his body. Your goal is to strife for perfection which is usually a goal you will never reach. have attention to details: remove stray hairs and shape his eyebrows (don't over do it but removing stray hairs and giving some shape to his eyebrows will actually make her look better both as a man and as a sissy), make him do a manicure and pedicure regularly and enforce a strict diet to get his body in sissy shape. Slowly start behavior modifications ('thats no way for a girl to act') with emphasis on the fact she is a slut, Theres probably a lot of work to do but it will be so much fun!
4. Making Her Useful
You don’t ever need to have any feeling of self-consciousness or fear of rejection. With a sissy you are free to be fully yourself, telling her exactly how you want to be treated. Be selfish. Be lavishly, unimaginably selfish. Ever wondered what it would feel like to have your asshole softly licked? Ever had the desire to fuck someone’s throat and watch the mascara run down their cheeks as they gag?How about having your pussy worshipped while you watch tv? Be honest with yourself as you experiment. Your sissy will thrive on your genuine enjoyment and satisfaction.
Don’t ever feel a sense of pressure though. If all you want is a foot rub, all she gets to do is give you a foot rub. Most importantly: don’t let her cum. If you only remember one thing in this chapter, make it this one: as soon as a sissy cums, she instantly becomes almost entirely useless. As bizarre as it seems, your sissy is a completely different person ten seconds after an orgasm then she was ten seconds before it. Her satisfaction comes from being allowed to pleasure you. We’ll cover a little later some ways that you can occasionally allow her a sexual reward, but for the most part you are the only one who gets to have orgasms. Lots and lots of orgasms.
The other most common use for sissies is domestic chores. Never politely ask a sissy if she would like to complete a task for you. This makes her feel as if she is your equal and is doing your housework of her own volition, making it drudgery. But if you firmly command her to do something, she will tingle with submissive excitement as she works - especially if she knows there will be consequences if she fails to do the task correctly.
The more humiliating the tasks the better, and whenever possible point out to her that a real man would never obediently do these demeaning tasks. Depending on your situation, a sissy may eventually be able to handle the majority of your domestic tasks…laundry, cooking, dishes, cleaning.
If you have her perform a task that has a “masculine” perception, such as mowing the yard, be sure she does it in very feminine attire. Of course, whether or not you want the neighbors seeing a ballerina mowing your grass is up to you.
5. Rewards
A sissy’s life shouldn’t be entirely without little selfish pleasures, although they should be very rare compared to yours. Although they do require a small amount of effort on your part, properly spaced rewards will keep your sissy incentivized and even more eager to please.
Her single biggest treat will more than likely be the occasions she is allowed out of chastity. Make sure her next release date is on the calendar, and keep up with moving it later or earlier based on her behaviour. This date will be etched in her mind at all times, as her frustrated little penis squirms inside it’s prison.
The last thing you want to do though is just allow her to run off and privately masturbate as soon as she is free. While some sissies can handle this, many will have waves of guilt and echoes of masculinity surge immediately after masturbating. For their own good, you must ignore their pleas to be allowed to touch themselves freely.
Her only orgasms should be “ruined”. A ruined orgasm is essentially one in which pleasant stroking contact is not present, allowing the cum to ooze out without the intense sensations and emotions of an orgasm with full stimulation. This will leave her feeling somewhat relieved, but if done correctly she will still be slightly horny and unsatisfied. Her sissy psychology will hopefully remain at least partially intact.
Give her the key to her chastity device and allow her to unlock herself. Make sure she knows the consequences will be extreme if she is in the least bit disobedient during this process.
Once unlocked, restrict her hands with cuffs or cable tie behind her back.
From here there are a few different options.
The easiest is to use a vibrator and hold it against the underside of her penis, right where the head meets the shaft. Verbally humiliate her while you hold it there. Tell her this is the only kind of orgasm a sissy like her gets to have, and tell her to hurry up and shoot her little load. The more you can get inside her head with your insults, the quicker this will go. Of course, if you’re enjoying yourself, take your time and even pull the vibrator off when you think she’s getting close to cumming. If you’re feeling especially cruel you can put a time limit on the “treat”, and she goes back in chastity once times expires regardless of whether she has been able to cum.
If she cums from this method, simply pull the vibrator away as soon as her orgasm begins. The cum will still ooze out, but you will have successfully ruined it.
The more “hands on” approach is to give her a traditional handjob and pull away as soon as she starts to cum. This technique isn’t nearly as foolproof though. It’s very easy to stroke just a little too long, giving her a few seconds of “thrusting” orgasm. Even if you let go halfway through this kind of orgasm, she will still have felt the hormone surge and will likely not remain in her sissy mental state.
Whether or not a sissy should ever be allowed a satisfying orgasm is a matter of debate. I personally like the idea of sissies being allowed one full orgasm annually on their birthday, or allowing them one un-ruined orgasm for every one hundred orgasms they give you. This has the added bonus of keeping her extremely excited for opportunities to pleasure you.
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