The history of sissy femdom can be traced back to the early days of the internet. Among the very first recorded circumstances of sissy femdom can be found in a Usenet newsgroup called alt.sex.femdom, which was created in 1996. In this newsgroup, users would share stories and dreams about dominant women who would require submissive males to dress up in womanly clothing and carry out various tasks for their amusement.

The origins of sissy femdom can be traced back to the early days of the web. In the early days of online chatroom and forums, there was an active however little community of people who had an interest in exploring and sharing their fantasies of being submissive to dominant ladies.

The most popular sissy femdom fantasy is most likely the one where the sissy is required to wear feminine clothes and made to do womanly jobs and tasks. The sissy is generally humiliated and degraded in front of others, and may even be made to carry out sexual acts.