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The Sissy Ownership Guide

While this guide will hopefully be useful to anyone interested in the idea of owning a sissy, a primary goal in writing this is to introduce the idea of sissy ownership to people who are relatively unfamiliar with the concept. Chances are, almost regardless of where you are, there is a potential slave near you who would love nothing more than to be allowed to serve you. And while the seemingly crazy psychology of these extremely submissive (fe)males might feel complex initially, there really are some basic guidelines that will make bringing one (or three) into your life very enjoyable.

If you’re sitting at your computer right now, a bit bored, a little horny, but not feeling like going out...a sissy could be perfect for you. In most situations a sissy won’t replace your primary companion, but they can be a great addition. If you’re a guy, chances are you’re considering whether or not to get a quick fap in tonight before bed. Instead, have a sissy on call. She could be under your desk softly sucking your cock right now as you read.

Ladies, you might love the same kind of attention, or opt instead for a long massage.

No one is more obedient and eager to serve than a sissy, and there are generally no strings attached whatsoever. Have her rub your feet and make you dinner, then tell her to do your dishes and clean up the kitchen before sending her home.

Sound perfect? It’s pretty close.

Sissies are everywhere!! If they weren’t such pansies they would have taken over the world by now. If you already have one in your life you can skip this section, or maybe you want to add a few more to your stable…

While there are a handful of personals sites geared towards this scene, chances are you will have even better luck putting a post on Craigslist or Fetlife. Generally sissies aren’t the most bold bunch, so post your own ad instead of waiting for one of them to create a listing.

Be detailed about what you’re looking for. How often do you want them to be at your house? What services are required? What kind of appearance would you like?

From the very first communication, be direct and confident. You’re in charge. If that bothers them they can get lost. You’re looking for a gurl who will be obedient and responds well to your authority.

Appearance is of course important, but focus initially on attitude. An obedient gurl with a strong desire to please will work hard to look how you want her to if you give her a little time and practice. A lazy sissy who is just looking for a quick thrill will only waste your time.

Your first meeting can be in public if she’s uncomfortable coming directly to your house, but regardless, you should be confident and in charge from the moment you meet. At no point are you equals. How you want her to greet you is up to you, but something along the lines of a polite bow and curtsey (or kneeling if in the privacy of your home) are a good idea to set the correct tone immediately.

If you establish from the very beginning that you are in charge, you will also avoid the awkwardness that often occurs when someone makes the mistake of initially greeting someone as an equal and then having to make the transition into dominant/submissive mode with them.

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.

It’s a counterintuitive paradox that can be a bit challenging to get your head around at first, so I’ll give a few examples.

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.

Another example is physical discipline. The sting of a paddle itself is in reality unpleasant, and it’s only because of it’s unpleasantness and humiliating nature that so many sissies are drawn to it.

Confusing, right?

Don’t worry, you don’t need to fully understand or try to relate in order to have a great time with your sissy and give her exactly the treatment she craves.

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.

If they have a blog or other journal, this can be a backdoor way to see the kind of relationship that most appeals to them. Or have them write out what their ideal situation would look like.

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.

Owning a sissy doesn’t need be complicated or require a huge amount of preparation, but having a few basic principles in place will set a great foundation for a rewarding experience for both of you.

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. She will no longer be genuinely interested in serving you, and will obey only out of a sense of duty.

You need to control her orgasms. This may not sound especially exciting, depending on your personality, but this small bit of effort on your part is absolutely critical to a having a useful sissy.

At first she may be obedient and abstain from touching herself, but in the long run the only real solution is a chastity device. These can be a bit of a hassle, but make that her problem. Have her research and buy her own device. There’s a fairly good chance she’s already interested in the concept, and she may already have a few devices available.

The security of these devices vary. The more casual ones are sufficient at first, but if your relationship with her shows signs of lasting, you may eventually want to have her graduate to a device that utilizes a piercing or urethral rod. With these she will be completely at your command and unable to escape.

Again, don’t let a sense of guilt alter your behaviour towards her. She will be desperate to cum much of the time, but will gradually adjust to living in a constant state of sexual frustration; excited to be your sissy and eager to please. Orgasms should be very special treats - only permitted in special circumstances, and only when you know you will not be requiring her services for a day or two as her submissiveness returns.

Be clear about your desires in regard to appearance, and don’t be afraid to discipline if she fails to comply. Most owners prefer a sissy shaved smooth from her neck down. Many also want their gurl slender, so weight goals and consequences for failure to meet them can be effective. We’ll cover some of the easiest ways to discipline your sissy later.

If you want her as feminine as possible, make that clear from the beginning and don’t be afraid to punish if you deem her efforts insufficient. Keep in mind that there are limits, and sissies are rarely exceptionally attractive as either males or females. Just make sure she knows what you like and dislike, and that she’s making every effort to meet your tastes.

Sissies will often have a particular attire they are attached to. It’s a good idea to be somewhat accommodating to their fantasies in this regard, but be sure it’s something you also find at least somewhat appealing. Clothing tends to reflect extreme femininity because of it’s emasculating nature, increasing the humiliation of their situation. Have her try french maid costumes, lingerie, pleated skirts and stockings...anything overtly feminine that you would enjoy seeing her in.

Modern society has evolved to stigmatize creating overt luxury for one person at the expense of another, but sissies are one of the few groups of people who seek to live outside that norm. As their owner, you are merely granting their wish to be taken advantage of.


First off...sex!

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. Sex should never be work for you.

And even though this has already been covered, I’ll say it again: don’t let her cum. 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. More on that later.

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.

Modern society has evolved to stigmatize creating overt luxury for one person at the expense of another, but sissies are one of the few groups of people who seek to live outside that norm. As their owner, you are merely granting their wish to be taken advantage of.

There are two kinds of discipline when punishing your sissy, with a bit of grey area in between.

The first is largely symbolic; meant primarily as a means of reminding her of her place. The second is meant to be more purely unpleasant, and is used to alter her behaviour directly.


Let’s start with the first kind.

The symbolism of obediently lowering her panties and bending over is psychologically powerful. It’s a physical sign of deference, and as she looks at the floor with her bare ass in the air, her submissive sissy psyche is fully engaged.

For this reason, it can be a good idea to perform “maintenance” discipline very regularly - even if not merited by any specific behaviour. There are few more effective ways to click her into a submissive mental state.

Implements to be used in this case should be only moderately painful: hairbrush, light crops, belts. The pain level should be adequate to make her squeal a little, but stop short of bringing tears.

Allow some space for creativity. Anything you can think of that sounds humiliating will be perfect for this type of discipline. Make her stand in the corner with her nose to the wall for twenty minutes. (This feels like forever, trust me.) Have her kneel and give one of your doorknobs a richly-deserved blowjob. Gag her and lock her in a dog kennel. Have fun, and be sure to document with photos so she can relive her humiliation later.

The second kind of discipline is meant for genuine behaviour modification, and if done correctly shouldn’t need to be carried out very often. The threat of this kind of punishment if she fails to be on her best behaviour should be looming in the back of her mind at all times. With the correct incentives in place, a sissy will be remarkably perfect in her obedience.

More severe spankings can work for these kinds of discipline, depending on their pain tolerance. Opt for more painful implements, such as a cane or paddle with holes. She should have tears running down her cheeks by the time you’re through with her. If you have nearby neighbors, a gag is probably a good idea.

A method requiring less effort is to have her tuck her little testicles back between her legs as she bends over, and then swatting them with a ruler. You will be impressed by how little it takes to get a sissy squealing and promising to change her ways with this method.

But the easiest punishment by far is simply adding time until her next release from her chastity device. Tell her you’re about to add a week to her time in chastity and her attitude will immediately adjust dramatically. Remember, she’s desperate to cum, and will do almost anything to avoid lengthening the time until her next release.

If the idea of having to discipline someone sounds tiring to you, stick to using just this method. It’s extremely effective, and requires minimal effort on your part.

There are a myriad of other potential means of punishment to keep your sissy on her best behaviour, and her personality and tastes will largely dictate what will be most effective. Experiment, watch how she responds, and enjoy making her squirm and whimper.

You’re the boss!

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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Comments (3)
  • So helpful and educational for all the young girls out there! Love it! ???

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    • This is a great article and I copied it to my blog.

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      • As a sissy slut slave, I am more attracted to men than females. As a sissy, I consider myself a girl, and sex with men is heterosexual, sex with women or other sissies is lesbianism.


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