Are You a Sissy?

What Is a Sissy?

“Sissy” is one of those words whose meaning depends a great deal on who is saying it—and how.

Spoken by a playground bully, it is an insult. Adopted by an adult describing himself, it can be an expression of identity. Used between consenting adults in a private relationship, it can have an erotic meaning.

Same word. Very different intentions.

For many of us growing up, “sissy” was a warning about the boundaries of boyhood. Cry too easily, dislike sports, enjoy pretty things, or hold your hands the “wrong” way, and someone might apply the label. The message was simple: boys were supposed to avoid anything associated with girls.

And being compared to a girl was supposed to be embarrassing.

That raises a question: what, exactly, was so terrible about being feminine?

From an Insult to a Chosen Label

Some adults have reclaimed “sissy,” using it affectionately or proudly to describe their femininity. They may enjoy dresses, lace, makeup, elaborate hairstyles, or an especially frilly presentation. The word can give them a way to embrace qualities they were once told to hide.

Others want nothing to do with it. They remember the humiliation attached to the word and have no interest in welcoming it back into their lives.

Both reactions deserve respect. Reclaiming a label for yourself does not give you permission to apply it to someone else.

Is a Sissy a Crossdresser?

A person might identify as both, but the words are not interchangeable.

Crossdressing describes wearing clothing associated with another gender. It does not automatically tell us anything about someone’s personality, sexual orientation, gender identity, or preferred role in a relationship.

Likewise, a man can be feminine without wearing a dress. And a man wearing a dress may be assertive, practical, outspoken, and entirely uninterested in being called a sissy.

A pencil skirt does not come with a compulsory personality.

The Adult Meaning

In some adult communities, “sissy” has a sexual meaning associated with feminization, submission, or consensual role-playing. That is one use of the word, but it should not be projected onto everyone who enjoys feminine clothing.

For many crossdressers, dressing is about comfort, self-expression, beauty, or the pleasure of going about ordinary life en femme. Buying lipstick is not an invitation for strangers to make assumptions about what happens in the bedroom.

Nor does femininity itself imply submission. Anyone who has known a determined woman should already understand that.

Who Gets to Decide?

Ultimately, the most useful question is not, “Does that person qualify as a sissy?”

It is, “How does that person wish to be described?”

If someone embraces the word, respect that choice. If someone dislikes it, respect that, too. When you do not know, a person’s name usually works beautifully.

We spend enough time having other people tell us what our clothes supposedly mean. We deserve room to explain ourselves.

And if enjoying a pretty dress once made a boy a “sissy,” perhaps the problem was never the boy—or the dress.

Wearing Boston Proper

Rich Little (right) femulating on television's The ABC Comedy Hour in 1972.