This my revised 2021 version of the definition of a sissy.
It is a practical way for self assessment and determining if you truly are a sissy and to evaluate engaging in training.
Sissies are autogynophillic males—males who derive sexual arousal and gratification by seeing themselves as female—who are essentially deeply attracted to the feminine so much so that they want to indulge as much as possible in the feminine, female experience. They long to become what they desire. This includes dressing in stereotypically feminine clothing which they fetishize, ranging from lingerie to full clothing, wearing of makeup, etc. This also often, extends to engaging in sex as a woman with male partners. This experience is driven by the desire to be a female, the idealized fantasy of a female they hold—sexual, submissive, slutty, etc.
Sissies are exclusively submissive, and this is entwined in the act of being feminine in two ways: first that they wish to become the submissive sexual ideal they have fantasized about through media, specifically pornography, and secondly that they enjoy a submissive sexual thrill from being feminized.
Sissies tend toward a younger persona, Some emphasize and fetishize very frilly clothing like crinolines, petticoats, satin, ruffle socks, etc. Some fetishize and embody the schoolgirl with plaid skirts and knee socks, though somewhat sexualized. The colors of pink and white are prominent to emphasize femininity and innocence, and to be anti-masculine. Some are into a sissy maid persona which combines the sexualized frilly trappings with subservience (often fantasized as serving a dominant male). And some take on the “slut” persona, dressing in an overtly sexual manner, generally in the manner of a young woman, 18-25.
The term “sissy” has a few components to it. First, it is a reclaiming of an epithet. But it is also embracing and confronting that epithet in some sense. Dan Savage once said, we often eroticize what we fear. A boy who is weak or who shows feminine behavior, may be called a “sissy” by his peers as a taunt to humiliate him. Adult male sissies may be eroticizing this fear or remembrance of that humiliation, and indulging in it.
Though the sissy is, at their core, a male engaging willingly in this activity and enjoying it, how much the participant acknowledges or denies their willingness varies quite a bit, as does the acknowledgement of their male gender. In many scenarios the person is forced to become a sissy, sometimes by a male for his sexual gratification. Other times the sissy is persuaded by hypnosis in service of becoming their true selves. In both of these scenarios, the sissy is submitting to the will of someone or something else, and surrendering their own agency. But in most cases, the sissy is an outright willing and enthusiastic participant. As for the acknowledgement of gender, they fantasize about becoming a woman, or being their true feminine self. They wish to be considered and referred to as completely female. It is quite common for a sissy to indulge in, and be turned on by, the humiliation of emasculation. Frequently this headspace is evident in the sissy being told by a dominant male that she is not a “real man” (alpha male), or is of little use as a male sexual partner, and that his fate, is to become a sissy. In this sense, the sissy’s manhood (or the diminution of it) is at the core of the psychology. With the emphasis on youth, a sissy is more often described as a girl, not a woman, and never as a man. Sissies usually adopt a personal first name which is distinctly feminine, sometimes deriving from their real male name (Chris becoming Christine, for example). Often in online situations the person refers to themselves as “Sissy [first name]” to denote their orientation and possibly as a subtle act of self humiliation.
As for relationships, the sissy persona desires to engage in sex with men. It isn’t accurate to describe this as homosexual, as the sissy is engaging in this from the persona of a female. This is to say that the panoply of sissy fantasy might include being a long term girlfriend or wife of a male (sissy bride fantasies abound).
The sexual activities, regarding sex, have the common theme is that the sissy is submissive.
Solo sexual practice is obviously most common and usually sissies dress in private It is very common to involve anal masturbation with a dildo, often preceded by the wearing of a butt plug. With the increase in chastity practice , sissies may engage exclusively in anal penetration, and have the goal of having a female orgasm this way. This is known as a “sissygasm” and has come to be a highly sought after, but difficult achievement. This comes with the psychology of training oneself to orgasm as a woman does, and rendering the penis useless.
In sex with men, the sissy is typically interested in servicing the man orally and being the recipient of anal sex. Receiving anal sex with a man is one of the most fantasized acts in sissy erotica. It is possibly the ultimate fantasy and demonstrates the sissy to be emasculated and submissive to the superior male. Although safe protected sex is practiced, much sissy erotica fetishizes semen, and the male ejaculating in the mouth or anus of the sissy. Even though the sissy cannot become pregnant, sissy erotica, particularly caption/meme imagery, makes frequent references to the top male “breeding” the sissy. Many images focus on the semen left behind after the act. Many sissy scenarios are based on the theme of the sissy being a sex object and placing the man’s pleasure above their own, even to the point of denying their own pleasure with a chastity device. Once more, the achievement of a “sissygasm” is fantasized about and sought after. Men prefer to not acknowledge the presence of the sissy’s penis. The sissy wish to not acknowledge their own male genitalia or feminize it by referring to it as a “clit” or “clitty,” and to their anus as a “pussy.”
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