Wearing two or more sissifying clothing is the main way of qualifying as a Sissy (the other way being the Pink Bow). Even if the player wears the sissy bow or collects lots of sissifying items, the player only counts as a "sissy" if they currently identify as male.

There are a few ways to encounter sissifying items, but

• When the player finds the item in a container.
• If the player loses their anal virginity before their penis virginity, they will become "cursed" and will periodically have sissifying items summoned onto their body.
• When the player unsuccessfully convinces any of the following monsters to have Dominant Sex, sometimes a sissifying item will be summoned onto the player:
  • Aeromancer
  • Gladiator
  • Mechanic (This doesn't actually happen when dominating him unsuccessfully, but if the player dominates him successfully, rides him, and then fails a secondary dominance check.)
  • Vampiress

Being a sissy is generally something to be avoided, as most of the effects are negative.

• Allows the player to Beg skill even without learning the related skill.
• Picking up the Demon Broadsword will cause it to transform immediately.
• Causes the Sissy Slut's Longsword to be prioritized when the Sword in the Stone is generated.
• Causes the Sissy Slut's Longsword to do extra damage.
• Causes the Gladiator to have the player eat her out rather than fuck her.
• Allows the RoboBellboy to force chastity cages onto the player.
• Causes the Wrestler to become aggressive immediately upon noticing the player.
• If Watersports Fetish is enabled, allows the wrestler to lock the player in between urinals.
• Sissies orgasm more easily from anal stimulation.
• If the player has had more than 6 anal orgasms, adds a chance for the Broken Clitty Tattoo to be summoned whenever the player has an orgasm.

The sissy class was the first multiclass.