Sissy Cuck Humiliation
Hey sissy, Just came by for the first time in a while. I'm glad to see you're still active. I'm also really excited and looking forward to reading your Sissy Ownership Guide when I get time this weekend. Take care, and have fun, and lots of blushing!

Hope you enjoy the guide :)

While I think it might be fun for sissies to read, my hope is that it will help at least a few non-sissies get a little glimpse into our psychology.


Testicle tenderizing…

Sissy testicle punishment really is the worst…makes me wince just watching…


Testicle tenderizing…

Sissy testicle punishment really is the worst…makes me wince just watching…


Should cucks be allowed to watch and masturbate on their wedding night? Or should they stay locked in chastity, having to earn the right to wank later?

One of my first caps :)


Should cucks be allowed to watch and masturbate on their wedding night? Or should they stay locked in chastity, having to earn the right to wank later?

One of my first caps :)

Second Life!!

If you’re on Second Life and looking for a sissy to abuse, search for Crissy E. or crissy839 :)

Just promise you’ll give me a good spanking and lock me in a cage.

1. Send this guide to someone you think would enjoy owning a sissy.

2. Post it to your blog so potential owners will be encouraged to contact you.

3. Be a good little slut.

Sissy Ownership Guide Part 7 - 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.

hi. can we talk?

sure - emailing chas19839 at gmail is easiest :)

Sissy Ownership Guide Part 6 - Discipline

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!

Sissy Ownership Guide Part 5 - Making Her Useful

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.