In this category of reviews we have included reviewed erotic aids and products that are suitable for feminizing your slave, for turning him into a maid, sissy, sissy maid, femboy or other similar intentions. It also serves mostly for transsexual individuals who are dealing with a MtF change, so from male to female. These pieces can also be used to do just that alternatively – typically chastity belts, fake breasts, …

SissyBoy is a label for boys who differ in behaviour and characteristics from the classic male model and tend to have more girlish characteristics. In English, such a designation is mocking.

The best way to translate it into English is the term “little girl”. The term sissy and sissyboys (or femboy/femboi) is often used in violent feminisation (one of the practices falling under psychological play from BDSM).

Such an individual displays sensitivity, does not speak harshly enough in relation to the home community, and appears vulnerable to the point of fragility. Appearance, such as a slim build or more delicate facial features, may also be a cause.

In English, the term “effeminate” or “weakling” is probably closest to the meaning.

Erotic meaning

In the erotic realm, sissyboy is a term for male individuals who have undergone violent feminization. This practice is popularly used in the BDSM community. In it, a male individual is forced to become a woman for the pleasure of his master or mistress.

This process is very humiliating for the man because he is not transvestite or transsexual. The important moment is the feminization of the man, who is aligned with his male role and is humiliated by the transformation into a woman. That humiliation is the exciting element that connects sissyboy and his trigger.

TALKING WITH SISSYBOY

We have one tester (or is it tester?) within the editorial staff who is just a feminized man – testing for us the tools that are just right for his transformation into a woman. So chastity belt, dildos, pins, nipple pumps, …

We interviewed him here:

“It’s better for me if my counterpart forces me to be a woman all the time.” – INTERVIEW with editorial sissy/trans tester

and also here: IN INTERVIEW with a Czech sissy/trans girl about sexuality and self-perception

1) The Feminization of Appearance

The feminization of appearance involves the classic dressing up in women’s clothing. The man dresses in women’s underwear, bras, and is forced to use breast pads. The usually more angular and differently shaped male body looks very comical in women’s underwear, and the man is humiliated by this funny appearance.

Other ways are wigging, wearing makeup, walking in heels, which she usually doesn’t control anymore and therefore looks very ridiculous. The outfit can be enhanced with a miniskirt, T-shirt or blouse with a low neckline, mesh tights and coloured nail polish are also popular.

The man involuntarily becomes a sort of caricature of a woman, for which he receives plenty of ridicule.

2) Personal humiliation

At this stage, the man is pushed into roles and activities traditionally associated with women (although this may no longer be true in the modern world, but this order is often deeply ingrained in people’s heads). A man in disguise is forced into housework, cleaning, serving his mistress/master He is constantly subjected to ridicule and humiliation.

3) Sexual humiliation

The culminating stage of humiliation is the degradation of the man into the role of a female sex object. A very humiliating practice is the insertion of artificial penises into the anal orifice of men, or involuntary sex with another man with the assistance of his mistress.

For many heterosexually oriented men, the idea of sexual contact with another man is very disgusting and humiliating; the completed sexual intercourse into the anal opening is an outright unbearable indignity for them. Their ultimate humiliation, however, leads to the goal of experiencing climax with the object of their interest.

Sissygasm – what is it?

There’s also a password associated with this topic sissy-gasm– or sissy orgasm. Typically, such a climax is uncomfortable for the person, so for example when teased through the asshole (ala pussy) thanks to a penis or larger dildo / vibrator (ideally with balls and suction cup), or through a clit, or otherwise uncomfortable.

After all, this position is not about comfort and pleasure, but serving someone else, so it’s more like a sort of occasional necessity or even punishment in the form of a ruined orgasm. Also, the orgasm thus forced may be captured on photo or video. And perhaps funnily shared with fans on Twitter or another platform – such as OnlyFans and Patreon.

Alternatively, a sissy may be allowed her orgasm, but it’s typically more challenging to achieve than traditional masturbation.

Comment from Sissyna’s editor:

I disagree that it’s uncomfortable. Because sissygasm is a lot like normal climax, only more intense and harder to achieve for some of us. It’s like you’re in imperfect pleasure and you don’t want anything else at that moment. Your lust is just to have your pussy filled and to finally cum because it is a very, very intense feeling.

lowering your counterpart to the level of an uncontrollable and consistently horny creature – or submissive little girl, or student if you will. Sometimes the arousal can be so intense and the result so far gone that it wets the pleasure. And yet she is then filled with the feeling that she hasn’t reached climax and is all the more desperate and horny for it.

18+ photos from the editorial Sissy testing

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What can raising a sissy look like

We tried it out for you and for you. This step-by-step, evolving scenario can be an inspiration or guide for you to raise your own SissyBoy.

When communicating, keep in mind that the sissy is supposed to view her penis as a clitoris (obviously worthless, since she won’t be using it) and anus as a pussy. They are supposed to perceive themselves as women, so label them that way too, so she’s on board with that.

1) Entrance test

You first need to know what you can count on, or what the starting position in training is. So what the sissyna can’t/can’t do (and what you’ll be able to improve on).

For example, you can evaluate and write down on a particular day:

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  • what diameter can the sissy handle,
  • what length can pussy handle,
  • what diameter can the pussy handle,
  • what depth can the pussy handle,
  • diameter of clitoris during erection,
  • length of clitoris at erection,
  • longest wearing of the clitoris,
  • longest dildo insertion,
  • longest make-up as a woman,
  • how many days a month you’ve been out the most as a woman,
  • longest wearing female clothes,
  • number of fingers in your pussy.

Why a particular day? Because you will also set review intervals where you will revisit all the points to see if there has been improvement in them according to the training/education plan. Perhaps monthly, quarterly, or at longer intervals.

2) Next, you will set the rules:

  • no spraying/orgasms without permission from the Lord/Mistress,
  • strict wearing of women’s underwear,
  • locking yourself in a chastity belt,
  • peeing in the toilet while seated,
  • no posting on social profiles without consent (typically applies to purely erotic profiles – Twitter, OnlyFans, …),
  • accurate entry of the date of the last orgasm/shot.

These points are just inspiration, we definitely recommend to engage your imagination and find other obligations/rules that must be met and followed by the sissy for you. And of course, when there are rules on one side, I’m sure you suspect that you’ll be preparing/inventing punishments against them in a while. There will always be violations, insubordination that deserves punishment and straightening out.&nbsp

3) Preferences about sexual practices and education

Find out the boundaries of your new toy – we recommend having them fill out your BDSM questionnaire.

This will give you a basic frame of her boundaries and options or preferences – these are more for interest or as a starting point. Because she’s there for you, for your pleasure, for your shaping, so if she doesn’t prefer something, that’s purely her problem.

You can just tinker primarily change those boundaries to your liking and liking. 

4) Nurture Mode

Next, determine the individual tasks and how often they will be repeated. This will be the basis of your reeducation plan, as you must remake your sissy in your own image and intent.

Typically, this may include:

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  • dressing in feminine clothing (stockings, tanga, garter, top, dress, shoes, wig, …),
  • women’s makeup,
  • nail painting (and overall manicure and pedicure),
  • locking an unneeded penis in a chastity belt (aka a cage),
  • taking regular body shots (perhaps always while locked in a cage),
  • going out in full costume as a woman,
  • needing to go to the ladies’ room,
  • regular blow job training or mounting dildos or other realistic toys,
  • regular shedding of pubic hair (legs, genitals, …) (or specifics of shaving – pussy line, …).

5) Penalties for violations

How to punish sissyboy for breaking the rules? It will differ at the beginning if the education is done in person or remotely. In person, everything will obviously have more emphasis on execution and also more variety. At a distance, the fact that the sissy is being controlled and punished by someone she hasn’t even seen can again play a role, which can also add to the (psychological) intensity of the punishment itself.

At a distance, the amount of objects, toys, or tools you have acquired for the sissyboy specifically for punishment purposes will also affect you more significantly.

5a) Pro

It’s a good idea to send him pins, inflatable oubliette, larger pin, nipple clamps, weights calamity stick, or any of the harder punishment aids… just in case (which, of course, will always happen) so he can punish himself.

Typically, these are aids that have some sort of after-effect on the body (so they are unpleasant as punishments and therefore have an educational after-effect for training) and can therefore be really checked – both by a photo after the whip strikes, for example, or calmly live on livestream (for others too?) as he punishes himself for example by impaling himself on a larger penis than he is used to, …

5b) Homemade

Alternatively, for self-spanking, a good old-fashioned boiling pot can be used, for nipple-spanking, a pair of skewers joined at both ends with a kitchen rubber band (inspired by Japanese bondage-style shibari), etc. 

5c) Tasking

Typical punishment is enhancing his/her submission and other variations from BDSM practices – so for example:

Of course, the individual punishments must be based on your normal functioning – if a sissy is by default obliged to clean up after herself after a cumshot – licking her own semen – then she won’t be in his punishments again, etc.

6) Slave contract

Insure your bitch by signing a detailed slave contract where she agrees to the educational regime/discipline given – the basis of this can be our Slave Contract template download. This is purely your psychological game, because of course this type of contract is not downright valid.

But the act of drafting the contract, signing it,confirming it with some concrete act/practice, is very intense for both of us.

7) What next?

You already know what she can do, what her limits are, what the dog doesn’t like = so you can take that into account and set specific tasks, regimen, and of course punishments for breaking each point accordingly. You can get inspired below, because everything we write here (both in this post and in our magazine) we test on ourselves and on our partners or toys.

8) Re-education plan – inspiration

Another inspiration may be this educational plan for our editorial sissy, which is the inspiration for this very article as well as the list of tasks and BDSM punishments (mentioned above).

We are training her remotely (and with the advances of the modern world, so with evidence via photo/video and control via smart teledildonics erotic toys like Lovense, or resisting unlocking the key – via wifi lock box and more) to prepare her for the possibility that she may someday live to see an in-person encounter and final test.

There she will have to prove if she is an obedient and clever bitch and deserves further our care and attention.

This final meeting may even involve surrendering all the keys to her chastity belt, so she will no longer be making decisions about her lap at all. Or he’ll get a new keychain, but this time stainless and an even smaller one (as an alternative to the current lightweight plastic one).

8a) Starting reeducation with:
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  • Wearing the chastity belt 2 times a week from wake to bedtime,
  • 3 times a week of body strengthening/slimming exercises (at least 30 intense minutes),
  • Wearing an inserted anal jewelry in the pussy 2 times a week,
  • 1x per week obligation to go out dressed as a girl (makeup, clothes, shoes, wig).

Missing here (and will be required in the future) is blowjob training, binding on dildos with increasing diameter (perhaps in the future and XXL ones), … to be ready for whatever we personally imagine for her, if necessary (in the future).

No squirting and orgasm tolerance, wearing panties as basic underwear, and being available for long distance assignments through our communication channels at agreed upon times are all important.

We work together: