The Art Of Sissification: Is ‘Sissy’ A New Sexual Orientation?

A generation or two ago when gender roles were more strictly defined, a “sissy” was the last thing a man wanted to be called. It implied that he was a pathetic weakling, a failure at being masculine during an era when masculinity was the ultimate goal for all males.

These days, in a climate where masculinity is seen as more toxic and dangerous than virtuous and heroic, some men are going out of their way trying to earn the privilege of being called a sissy. They willingly put themselves through a systematic process of physical and psychological self-emasculation known as “sissification.”

Also known as “forced feminization,” Wikipedia describes the sissification process thusly:

…the practice of dressing a submissive partner as a woman and/or encouraging or training a submissive partner to act in a feminine or exaggeratedly feminine (“hyperfeminine”) manner. If assigned male at birth, the submissive partner may be called a “sissy.” Feminization is usually achieved via cross-dressing, where the male is dressed in female attire, ranging from just wearing female undergarments to being fully dressed in very feminine attire, including make-up, hairdress and nail polish. Some males take on tasks, behaviours and roles that are overtly feminine, and adopt female mannerisms and postures in tasks such as sitting, walking, and acting in a feminine manner.

Sissification differs from being transgender in the sense that choice is thought to be involved, not only in “becoming” a woman, but in reversing the process. As opposed to popular notions about being transgender, a sissy isn’t “really” a woman—he’s a man who’s volunteering to have his masculinity destroyed, with the understanding that if he doesn’t go too far in physically altering himself, he can always reverse the process. He isn’t seeking his “true” gender identity; he’s undermining it because erotic humiliation gives him a sexual thrill.

At its root, sissification is also deeply misogynistic because it implies that there’s something weak, pathetic, and humiliating about acting like a woman.

Becoming a sissy requires making changes that are both physical and mental. The physical transformation involves things such as cross-dressing, leg-crossing, laser hair removal, wearing makeup, using female cosmetics, and sitting down to pee. It also involves adopting traditionally feminine mannerisms such as stepping daintily, arching your spine, and swishing your hips. If taken to an extreme, it can also involve female hormone injections and even sexual reassignment surgery.

The psychological transformation involves the utter destruction of one’s masculine identity. Often a man will be required to feminize his name—”Daniel” becomes “Danielle” and “Patrick” becomes “Patricia.”

Sissification also involves mind control through erotic hypnosis in which the sissy-in-training watches videos that glorify the process of worshiping giant cocks that put the would-be sissy’s pathetic little “clitty”—i.e., tiny penis—to shame. He is sternly instructed to gain sexual satisfaction from prostate stimulation rather than penile stimulation and is trained to achieve “sissygasms” by either sitting on dildos or being fucked in the ass.

The aspirant sissy is gradually brainwashed into eroticizing the act of being sexually humiliated and having his manhood mocked. As slogans such as YOU ARE BECOMING A GIRL are flashed across the screen, the would-be sissy learns to be repulsed by all that is submissive and feminine while growing more and more sexually attracted to alpha males and their monster cocks:

You love cum. You want to be a girl. Being girly is what you really want. Admit to yourself that you are a girl and go ahead and do something about it.…Forget about being a man. Embrace the real you. You are a sissy bimbocumslut….

A professional “sissy trainer” describes how she turns males into sissies by snuffing out their masculinity:

I get you there by a mixture of hypnosis, psychological trickery and by leveraging the subject’s own curiosity. The secret is to slowly and gradually help the subject see and accept all the amazing benefits of feminization. By using consistent conditioning and a calm reassuring logic the subject starts to embrace more of their feminine side, and inevitably this grows a desire for a feminine body to match the new improved emerging identity.

Here a former self-identified male describes how his girlfriend systematically sissified him and destroyed his initial resistance:

Soon she added a strap-on to her collection and one that squirted and she would pump lube in my rear end and tell me it was a special estrogen solution that would work its way into my system through my bowel. Then she would insert a butt plug to make the liquid stay in me till I absorbed it.

Honestly I was loving all the attention and the taboo role playing we were doing and I couldn’t have been happier. She switched out the straight porn for gay porn and every day she would only make love to me while I was watching the gay porn and telling her how much I wanted a cock in my mouth and ass and one in each hand….

Often such deliberate “mindfucking” and sexual self-humiliation backfires and leads to guilt, regret, and shame:

I became increasingly ashamed of myself, and after each time I did it, I knew that it was the last straw and that I could not continue doing this. It would literally ruin my whole day and make me want to stay isolated, in irrational fear that people would find out about it if I showed my face anywhere….It’s like I developed an alter ego of “being a sissy,” which all of these sissification hypnosis things encourage oh so much…. I got back home and decided to trash everything I had – the dildo, the plug, the clothes, the weed – everything that only perpetuated this habit and addiction. I woke up the next day, still in shock with what I had done. I couldn’t bring myself to leave my apartment and show my face, again due to that irrational fear of somebody knowing.

It shouldn’t be surprising that some men develop psychological problems as a result of chasing a sexual identity that is based on humiliation and self-hatred. Neither should it be surprising that in a climate which preaches masculinity is innately harmful, many men seek redemption and approval in the act of fleeing their masculinity.

The culture has shifted to the point where “sissy” is no longer the worst thing a man can be called. These days, the worst thing for a man to be called is “manly.”

In other words, we’ve evolved—or devolved, take your pick—to the point where there’s nothing wrong with being a sissy so long as you accept the premise that there’s plenty wrong with being a man. Thought Catalog Logo Mark

Quick Facts About Sissification


The fantasy depends on the idea that feminization is forced, although this is only a fantasy. The sissy makes a conscious choice to be feminized.


Begging to stop the process may be part of the fantasy and roleplaying.


Sissies often wear a chastity cage around their genitals to prevent masturbation.


Sissification differs from “fandom” fantasies in that the person degrading them is usually a male rather than a female.


Maid outfits—and maid activities such as dusting and serving beverages—often play a role in the fantasy.


Unless there have been permanent physical and hormonal changes made, sissification is reversible. Thought Catalog Logo Mark

About the author

Jerome London