In this article, we are going to answer questions such as Definition – What’s Sissy? What does Sissy Cuckold mean?
What does Sissy mean?
According to the Cambridge dictionary, Sissy is a boy who other boys dislike and laugh at because they think he is weak or interested in activities girls usually like. Also, a person who is weak and cowardly. 
In Wikipedia, it is also defined as a pejorative term, especially in the U.S., for an effeminate boy or man, with connotations of being homosexual or cowardly. 
However, in this text, we want to define sissy broadly in our cuckolding world concept. A sissy is a biological male; who acts really feminine, slutty, horny, also really bimbo-like, etc.
They tend to be really submissive but not all of the time. Most sissies are into men, but some are into women, some are Bisexual or Pansexual as well.
Check What Type of Sissy Are You: 12 Types Of Sissies – What Type Of Sissy Are You?
Most of them like to play with other sissies as well. Often they are into a form of hypnosis that comes from the hypnofetish community called Sissy Hypno. 
What does Sissy Cuckold mean?
‘Sissy cuckold’ can have a wide range of meanings. It usually implies that the male half of the cuckold couple is subservient and is open to being humiliated in some way.
The subservience may not necessarily be to the wife, it may just be to the wife’s partner(s)/Bull(s). Indeed, it is quite common to meet couples where both parties are ‘sub’.
The concept of being ‘sissified’ might include sucking the bull’s cock, ‘cleaning up’ duties, or even being anally fucked by the bull.
As with many aspects of cuckoldry, the limits of the cuckold sissy fantasy are limited only by those who are involved.
Cuckolds VS. Sissy Cuckolds
Within the category of “cuckolds,” there are subsets and nuances. This article aims to examine the differences between standard “Cuckolds” and sissy cuckolds.
The primary element differentiating “sissy cuckolds” from the cuckold pack is the inclusion of feminization. Beyond emasculation or the removal of typical masculine characteristics resulting in merely a eunich state, sissy cuckolds proceed into the realm of true feminization. This process can be willingly by “coersion” or by seduction from their partners.
Furthermore, all cuckolds can be said to gain pleasure (even the pleasure of Humiliation) from their cuckold activities. All cuckolds have this in common: their wife or partner is seeking or receiving pleasure from sexual activities with another man.
Sissy cuckolds are the same, except most often, they are feminized.
In conclusion, there are thousands of resources for those who wish to explore their sissy cuckold side. The first step in exploring this lifestyle, of course, is to learn as much about it as possible.
Then, if you have not yet done so, explain your fantasies and desires to your partner, and, with her consent, begin a mutual exploration into the life of sissy cuckolding.
For more information check: 13 Types of Cuckolds – What type of Cuckold are you?