The Difference Between a Sissy vs Crossdresser

“Sissy” is usually an adult kink label some people choose for erotic role-play with consent. “Cross-dresser” describes people who wear clothing associated with another gender for comfort, fashion, or expression and often non-sexual. The terms can overlap for some individuals, but they’re not the same.

Have you found yourself wondering what the difference between a sissy vs crossdresser is?

Are they the same thing?

Are these offensive terms?

“Adults-only terminology discussed; consent and respectful language emphasised.”

Table of Contents

What does “sissy” mean?

Sissy and cross-dresser (often referred to historically as: transvestite which is now outdated) are often thought of as interchangeable terms, but this is not true and may offend people on both sides. Whether you consider yourself a cross-dresser, a sissy, or just curious this article will help those who are confused to tell the difference between the two.

So what is a sissy?

A sissy is a man who dresses more feminine and acts more feminine. They tend to have more submissive personalities. People who use the word sissy for themselves may be of any orientation; usage varies by person and community. They may like to be passive and obedient to their partner. They may even want to live their lives as women, indulging in all hyper feminine and glamourous things.

What does cross-dresser mean?

A cross-dresser is someone who enjoys dressing in clothing that is typically for the opposite gender. It can be women dressing as men, but generally, when people are talking about cross-dressing, they are referring to men who indulge in wearing dresses and women’s lingerie. There are various reasons a person might cross-dress from a love of fashion, sexual arousal, self-expression, or they are just finding it fun and relaxing. A man who cross-dresses doesn’t always identify as a woman but enjoys wearing feminine clothing. A crossdresser may be more fashion focused and keen to attempt to ‘pass‘ by creating a more feminine figure.

Sissy vs crossdresser key differences at a glance

“Summary: ‘sissy’ is a consensual kink label; cross-dresser is an identity/presentation label.”

Common myths and the reality

• Myth: “All sissies/cross-dressers are gay.”
  Reality: People who use these labels can be straight, bi, gay, or any orientation.
• Myth: “Cross-dressing is a psychological problem.”
  Reality: Dressing is a form of expression; it isn’t inherently a disorder.
• Myth: “Sissy means weak.”
  Reality: It’s a consensual kink label for some adults; it says nothing about strength or character.
• Myth: “Cross-dressers identify as the ‘opposite’ gender.”
  Reality: Some do; many don’t. Identity and clothing aren’t the same thing.
• Myth: “Cross-dressers / sissies can’t be good partners or parents.”
  Reality: Relationship and family roles are independent of clothing or consensual kink.

Everyone who cross-dresses isn’t a sissy

Many cross-dressers are offended by being referred to as a sissy. They may have a negative attachment to that term. They may think that it is a put down; perhaps they are a bit on the feminine side and were tormented as a child about it. Being called a sissy may not be something they appreciate as an adult.

There are also men who cross-dress that are not necessarily more feminine, and they just merely enjoy dressing in either full women’s clothing. (see our Guide to Crossdresser lingerie.) Maybe they cross-dress to get in touch with their feminine side, but outside of cross-dressing don’t consider themselves feminine at all.

Unless you are told directly that someone is a cross-dresser or a sissy, it be best not to make any assumptions.

Cross-dressers, sissies and trying to define them

People who practice femdom are more than happy to be called a sissy, and they are men that are obedient and submissive to a mistress or a dominant mistress hence the name femdom. The mistress may even be a wife or girlfriend.

When someone identifies themselves as a sissy, they go from someone who likes to wear women’s clothing to someone who feels their most self in women’s clothing and acting more feminine, as well as being submissive and dominated.

Some cross-dressers may consider themselves sissies while dressing in women’s clothing, but once the lingerie comes off, the fantasy ends. It may just be a fantasy for them to be dominated by a woman while wearing female clothing.

There are so many varied reasons that contribute to men liking being called a sissy or being offended by the term.

Conclusion

When it comes to sissy vs crossdresser, it is an individual choice, and it is never cut and dry. It’s an evolving process, and some men may know right away, from childhood even that they are a sissy, whereas other men know they are not, but they do enjoy cross-dressing. Some men may even be offended by the term due to childhood trauma or a misconception that it makes them weak.

Whatever the case, they are definitely different and should not be used as an interchangeable term.

About the Author

I’m Tiffany Hart a young, vibrant entrepreneur with a soft spot for all things retro/vintage. On most days you’ll find me in a polka-dot dress, heels, stockings, and a trusty corselette, hunting down beautiful pieces and turning them into outfits that feel like you.

You can read more about me here.