Quick links: Sissy Training, Explained | The Kink | How To Try | Aftercare | My Experience | FAQs | Next Steps
Key Takeaways
- Sissy training involves “forcing” a male submissive into donning the clothing, shoes, jewelry, and makeup of a woman or girl, and then making them act out scenes that are stereotypically feminine and often humiliating.
- This can mix in a variety of other practices such as verbal humiliation, being placed in humiliating situations, genital caging and confinement, slave play, and various forms of BDSM roleplay.
- In most sissy training scenarios, the dominant is a woman. The submissive is always male, usually a cisgender male.
- Sissy training is a BDSM scenario catering to a sexual kink and has nothing to do with drag performance or being transgender or genderqueer. Any crossover between the different groups is rare, and a matter of individual circumstances instead of a general trend.
“Girls who are boys who like boys to be girls
Girls and Boys, Blur
Who do boys like they’re girls, who do girls like they’re boys
Always should be someone you really love”
What is Sissy Training in BDSM?
Sissy training is a fantasy. It is a kinky game that adults play to explore or subvert gender and masculinity. It is an opportunity for men to explore and embrace their feminine side as well as their submissive side.
Sissy training often subverts masculinity through transvestism, also called cross-dressing, or by wearing colors that are associated with females, like pink. This is often mixed with other methods of feminizing his appearance.
“I dressed myself in women’s clothes, put on ornaments, and covered the upper part of my body with a scarf, just like a woman.”
by Georg Feuerstein, Ph.D.; Shambhala, 1998
from Tantra: Path of Ecstasy
Thus, sissy training can include learning to wear women’s makeup, wigs, perfume, jewelry, and skin cream, as well as shaving and removing body hair. It can involve things like corseting as well as learning to walk in high heels. Sissy training can end up being a total makeover, as a man learns to play an archetypally feminine role, and look the part.
Sissy training can include various forms of humiliation. In a way, it is a kind of humiliation, because it is embracing emasculation. Sometimes it involves less cross-dressing and more submission or equal helping of both.
Sissy training is also one way that a man can enjoy getting pegged by a woman. It can be a way for a man to enjoy cuckoldry.
Sissy training can include the sissy learning to submit in other forms of BDSM play. Sometimes it can be mixed with slave play: he cross-dresses in women’s clothing, maybe a maid’s outfit, and does chores and housework.
Sometimes it can include watching sissy Hypno porn, pretending that the brainwashing actually worked. Sometimes, the sub is a bratty girl and needs a spanking.
The Sissy Kink: What It Is, What It Isn’t
Being a sissy does not mean that the sub is insecure in his masculinity. It also doesn’t mean that the same man can’t be tough, athletic, or effective in combat. It is temporarily emasculating and can be humiliating. It does not have to be.
Sissification is also not some kind of “gay conversion therapy” that makes a man gay or effeminate. There is no real way to forcibly change someone’s sexual identity or sexuality. Even liking pegging doesn’t turn a man gay. A man can be very heterosexual and still enjoy sissy training.
The sissy kink takes some harmful and wrong ideas that people used to have about women, femininity, and masculinity, and turns them into a joke. Sissy training then goes along with the joke, in a sexy kinky way.
Or it can be a way of loving someone so much that, unlike the White Town song lyrics, a sissy really can be their dominant’s woman for a while, even though they usually identify as a man and have a man’s body.
How To Try The BDSM Sissy Kink?
To train your boy to be a girl, first, make sure that it is something he wants to try and discuss the specific ways he’d like to explore the kink.
Start with something simple, but fun, like painting or doing his nails. Try applying women’s makeup. If he enjoys that, try women’s clothing, maybe including stuffing a bra to make it look like they have breasts. You can also try women’s wigs and a complete makeover and “transformation” in women’s lingerie and clothing or costuming.
You could also keep it simple and put your sissy in something pink, like a cute collar and cuffs for bondage, and have your sissy submit in various scenarios.
You could also try stimulating his nipples. Not everyone likes that; usually, it is a thing done to women’s breasts, and many men may not know if they really like it or not. Some really do.
“That nipple stimulation enhances sexual arousal in the great majority of women, and it activates the same brain areas as Yoni and clitoral stimulation.”
by Sivkishen; Diamond Pocket Books Pvt Ltd, 2015
from Kingdom of Shiva
Use sissy training to explore other kinks at the same time, like putting him in a submissive BDSM role, introducing a strap-on, or including another male playmate.
If your sissy is bisexual, starting with a dildo or strap-on can be a way to prepare them for receiving anal sex from a man.
Sissification Finishing and Aftercare
There will come a time when the sissy play ends, and the sissy will again want to reassert their masculinity. That means removing any makeup, showering, and changing back into their normal masculine clothes.
It means doing whatever they do that is associated with their masculinity, in addition to any other needed aftercare like first aid and discussions.
It can include going back to sexual activities in which they are again in a masculine role, like a blowjob or more vanilla sex. It all depends on the partner.
Personal Experience With Sissification
I have not been sissified myself, but I have participated in a sissification scenario with a play partner and her submissive husband. He was a gigantic, very manly ex-soldier, bigger than me, who worked as a construction foreman.
In his day-to-day life, regardless of being bisexual, he had to deal with being very stereotypically masculine all the time.
Seeing him done up in lace and lipstick, and setting aside all his masculine trappings and behaviors, was surprisingly hot. His tiny-but-tough dominant wife was normally a very cushy, loving top to her man, but this started out as a cuckolding scenario, so the humiliation was built in for him. However, things took an unexpected turn, and I ended up sleeping with both of them.
Hot tubbing afterward, he admitted to me that one of the things that made sissification hot for him was that he could lay aside everything he was “supposed” to do as a masculine man. He didn’t have to be tough. He didn’t have to take charge.
He didn’t have to “win” every situation he was in. Giving up his masculinity for a while also meant giving up its burdens–almost like a short, kinky vacation from a sometimes stifling gender role.
Sissification Kink FAQs
How does a sissy kink relate to the transgender experience?
In short form, one is fantasy and the other is reality. Sissification as a kink works because the submissive identifies as a man and is having that identity temporarily subverted. Trans women and femmes aren’t subverting their gender but asserting it.
Some people do use gender play to explore their gender reality or may discover something about themselves during gender play. But ultimately, sissification and being transgender have little to do with each other.
Does sissy training always involve humiliation?
Some would argue that it automatically does, as subverting your true gender is humiliating in itself. Others, somewhat problematically, take this a step further and point out that thanks to sexism, a man accepting a feminine role is automatically being “demoted”.
Ultimately, whether sissification in itself is humiliating really depends on the mindset of the sissy and the tone of the scene. Sissification can as easily turn the submissive into a princess or a bride as it can turn him into a servant or a slut.
Humiliation is often added to the mix, with the sissy placed in humiliating situations, fitted with a penis cage or other chastity device, cuckolded, etc. But that is all a matter of preference.
Is sissification misogynistic?
Some people argue that sissification throws women under the bus by creating a humiliation scenario based on sexist perceptions of them. Making a man into a maid, helpless loli-figure, or brainless, oversexed “bimbo” for his own gratification, they claim, ignores that women can’t escape these stereotypes by ending a scene.
The counterargument is that sissies are generally submitting to a strong woman figure and that most sissies identify as feminists and definitely do not ascribe these stereotypes to real women. However, this kink does ride a line that is uncomfortable for some people.
What’s Next?
Teach your man how to be a good girl and satisfy his secret submissive desires in a way he’ll never forget. Or give up your masculine trappings and serve your Mistress as a happy little maid.
Explore the sexy side of feminization, whether you’re being a praised, pretty princess or disciplining and degrading your bratty, disobedient slut.
Learn and talk with your play partner about sissy training before you start to experiment. And, as always, with all BDSM activities, make sure you trust your partner and use a safeword.
Notes
This post was initially written and published in March 2022 by Sexologist Robert Thomas. In October 2022, Oliver K rewrote the article to improve its depth, truthfulness, and accuracy.
