Sissy
An example of the distintive looks of a sissy (sexy dressing & lingerie, usually wear of wigs & possible use of a chastity cage)

NOTICE: In the following article this encyclopedia will use pronoun She when it refer to sissies. Notice that this encyclopedia respects people that use the pronouns them or they and it’s not our intention to offend anybody.

A sissy is a non-conformant biological masculine who adopts hyper-feminine behaviors and practices (e.g., crossdressing, putting on make-up), typically assuming the submissive role to a dominant female and/or male partner(s). This can be interpreted as a previous state to a transgender or transsexual stadium.

In the past a sissy was considered only a person that had effeminate manners or was weak compared to real men. Nowadays this term is in constant evolution and change since there was new generations that now use this gender as a validation for themselves to become femme.

It can also be considered that a Sissy is an intermediate kind of gender that is not classified in the Cisgender or the Transgender categories. This term can be reclaimed by Transgender people as this intermediate stage is considered a previous phase for the male to female gender reassignment.

Differences between Sissies and fetishists

Sissies are not plain crossdressers since the later only like to wear female attire so they can feel comfortable with themselves. On the other side sissies go a step further to have a more feminine image of themselves, they can achieve that by waxing or shaving their body, wearing chastity tubes to stop masculine masturbation habits, becoming sexual bottoms, accept an Owner that will control and guide their feminization process, undergo small cosmetic procedures and taking birth control pills or other supplements to start a semi transition period.

Also it must be noticed and not to confuse sissies with transvestite fetishists, since the later only wear female undergarments and attire without improving their femininity in the process and sissies do whatever they can to pass as females and to exaggerate girly attitudes.

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Anatomy of a Sissy

Infography of sissies’ genital organs (Pretraining stage)
 

As an intermediate between biological males and females, sissies’ sexual and reproductive functions are different from those original biological types. That’s why for example the structure commonly known as penis in males is significantly smaller in sissies, this feature makes this organ being called a sissy clitoris or clitty in modern English slang.

Other areas of the sissy sexual system can be:

  • The testies (counterparts of male testicles): Significantly bigger than the clitoris, they are covered by a structure that was called in the past scrotal sac but nowadays is being called the scrotal lips due to its similarity to female vagina’s labia. Testies principal feature is the production of sissy cream, this white colored slime is similar to male semen but it has the only function of pointing out the state of excitement of a sissy since that gender is forbidden or very limited from sexual intercourse that led to breeding children.  The sissy cream is more liquid in its pre-squirt period and more salty and creamy at the sissy orgasm stage.
  • G-Spot Gland: This organ, located between 3 to 5 inches inside the sissies’ assvaginal conduct is the main spot for sexual pleasure and orgasms since its stimulation makes them produce more sissy cream that led to squirting and pulsating stage. The G-Spot Gland, formally known as Prostate can be reached by sexual intercourse with real Men or by the use of Strap-On and other sexual toys by Women or by themselves via masturbation.
  • Anal Vagina/Asspussy: the center of sissies’ sexuality, this cavity is located between the butt cheeks and can be used for receptive intercourse with Men, Women and Trans people. This cavity helps sissies to reach their G-Spot and due to the size of normal penises, intercourse can lead to stimulation of the Rectal Cervix, located a few inches inside the asspussy area.
Infography of sissies’ genital organs
(During chastity and assvaginal training)

A person usually understands her sissy gender by a couple of stages, starting from the pre-adolescence and ending at the mid-20s to early 30s. They usually start their lifestyle as crossdressers, commonly wearing their mothers and sisters clothing while masturbating, this latent sissy period can carry on until the age of 18 when they start buying their own effeminate clothing and make up.

On the latent stage and the beginning of the exploration stage sissies do purge because of their contradictory feelings about letting go their masculinity ego embracing effeminate submission. At this stage of exploration sissies usually engage in anal stimulation, starting to plant the seed of the real anatomical size that makes humans have sexual pleasure. The undersized clitorises of the sissies stop growing at their mid-teens, and that kind of contrast between the exposition to porn and the reflex at the mirror of the clitoris of them makes them understand their sissy stadium and paving the way to finally accepting their real gender.

During the sissy training and adult stages the sissies usually enclose their clitorises with a plastic or metal device commonly known as a “Chastity Cage”. These kind of devices are used to shrink the size of the former penis transforming the already small frontal tissue of the girls into a small sized clitoris. Another tools in the training process are butt plugs (that are worn as tampons during the day) and anal training with real Men sized penises (starting from a minimum of 7 inches to very extreme measurements like the dong dildoes).

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History

An example of Victorian era petticoating & pinafore discipline.

From the beginning of times there were sporadic and limited examples of what a sissy really was. Most notable examples were in classic historic episodes such as the English Renaissance Theatre, more precisely in the live performance of plays by writes like William Shakespeare  in which male young men had to cross-dress and adopt effeminate manners in order to achieve female roles;  in the Victorian Era and in European countries young boys were forced to wear female underwear and undergarments as punishment or to pose in family pictures, this was eventually called Petticoating and Breeching by historians and experts; and of course one of the most famous example of a young expression of feminization can be the Rebecca Riots of Wales in the mid-1850s. In the Twentieth Century, crossdressing related to sissification first appears in the writings of the first decade of that century with works like the notable “Éducation Anglaise” of 1908 by Lord Kidrodstock, a story involving English discipline and forced feminization. The gender bending activities are considered to have its peak in the 1950s when the first expressions of alternate sexuality were shown to mainstream audiences thanks to filmmakers like Ed Wood and its biggest movie Glen or Glenda.

Between the 1960s and 1990s, the sissy subculture started declining due to more radicalized expressions by the mainstream Female and Male genders (Radical Feminism and Male Homosexual Leather subcultures respectively). People that were in the umbrae of transsexuality or transgenderism had to hid in the shadows of small cocktail clubs at the gay communities and the generation of those years is mostly known as a very closeted one, expressing their sissiness until a lot of years later. A common milestone for the crossdressing sissy lifestyle being repressed by mainstream communities is the infamous Queen video “I want to Break Free” of 1984. Singer Freddie Mercury repeated that drag performance, inspired on the British comedy Coronation Street, but received backlash in countries like Brazil or the United States.

Barbi Satin, one of the pioneers of modern sissy movement. Her fetishistic writings on Crystal Story Site are still considered very transgressive.

Sadly because of the AIDS epidemic of the 1980s and the ending of the chants of radicalism, people started finding a niche in the dawn of the Internet era and the Alt bulletin boards. These kinds of places were the cornerstone for the first effeminate communities that gave birth to the Sissy era. Sites like Nifty (founded in 1993) and Literotica (established in 1998) were the first places in which stories about feminized biological males can be found; of course we must not forget the impact of the Crystal Story Site, that was the first ever place in which strictly sissy stories were archived and stored. This kind of place was, to be honest, the place in which great pens of our Sissy Founder Figures like Barbi Satin started writing contemporary sissy history.  

The Sissy community couldn’t have a more stable scene due to limitations of early social networking, but sporadic attempts were made to unify the thinking of the young girls that went to start this journey. Most famous social media sites of the ending of the century and first half of 2000s are The School of Sissify and Club Sissy; virtual places in which girls received training in the traditional effeminate role and had chat rooms where they could meet other people and arrange for encounters. After the consolidation of the Twitter and Facebook social networking those two sites presented a decline in the quantity of new members, same happens to MSN and ICQ around the period between 2006 and 2008.

Around the same period of time the first sissy groups appeared on Facebook network, and with that the appearance of the first SM Masters and Blackmailers can be documented. Those kind of people usually tried and eventually controlled the lives of the sissies that were into those social groups. Of course the demands of those Superiors were far more what those girls could bear and that led to the first cases of exposing on media.

Name, Age, ID numbers, Addresses; that kind of personal information were exposed on big colored charts with a collage of pictures and posted on Yahoo Groups and pornographic sites as ImageFap or XTube.  This kind of activity improved on the second decade of the 21th Century with the presence of Sissy IDs (parodies of Social Security cards fashioned with the sissy name, a “never” expire date and a “sissy since” tag with the captions “Expose, Spread & Repost” all over them).

An example of sissy exposing editing. Characteristic IDs and collage can be seen on the picture.

Thanks to the progressive policies of the 2010s decade being a sissy is no longer something derogatory on the internet networks, sissiness can be only considered nothing else than another gender expression based on acute femeneity and submission; this added to the great affluence of men in their early 20s that accepted their destiny as sissies created a new community based in submission and constant feminization of the body, mind and soul. Of course practices like Blackmail or Exposure are still embodied into the sissy self, the girls of the community had reached new goals for it, using the threats as an opportunity to have a more efficient feminization process, and the exposure is commonly used as a way for shy sissies to express themselves in a usually repressive living context.

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  1. Avatar
    Vivian

    Great write up!!!!!!

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