We ask the question - what is Sissy? and are you a Sissy Boy? well according to Wiki a Sissy is derived from the word 'sister'. it's a term given to boys or men who don't gender conform. A boy or man displaying effeminate traits. A 'Sissy' is the male converse of a 'Tomboy' but usually carried more negativity, unless of course in the BDSM community.
The BDSM meaning of Sissy -
Sissification (or Feminization} is the practice, of switching the gender role of a male submissive to female.
It is usually achieved through cross dressing, where the male submissive is dressed in female clothing and lingerie. There are many degrees of feminization; some include wearing female underwear to being fully dressed in effeminate attire and make-up, intentionally playing to many classic female stereotypes.
Some submissive males often take on tasks, overtly feminine behaviors and roles (such as being a sissy maid), and adopt female mannerisms and postures in such activities as sitting, walking and acting in a feminine manner.
The costume is sometimes very domestic, suggestive of servitude and often out-dated, distancing the submissive male from acceptable feminine clothing and even farther from contemporary conventional male attire. This may also be an opportunity for ageplay, further diminishing the submissive male's status.
Alternatively, the costume may sometimes be very suggestive (e.g. mini-skirts), linked to other male fetishes regarding female clothing (e.g. PVC or latex attire), and exaggerating female characteristics (e.g. high heels and corsets).
Naming may also be employed. A submissive male may be given a female name, designated as "a good girl", or given a name which is an explicit insult applicable to females, such as "whore" or "bitch' or even "slut" which while it may not be an insult in all cases, implies out-of-control female lust, a reinforcement of the feminization.
We have the perfect collars for any 'Sissy Boy' with our 'Slut' and 'Bad Girl' Collar and coming soon is our 'Sissy' Collar.
Greater levels of feminization may also mean the male being the recipient of anal sex using a strap-on dildo or a male accomplice. Even caging your Sissy boys manhood.
While many may find sissification to be a form of humiliation, many participants view the activity as a positive reinforcement of role an find it a release from real life.