So you might be a sissy!

Have you ever been calles a sissy before?

As you probably know, “sissy” is a derogatory term that’s used to describe men or boys as weak, effeminate, cowardly, and/or gay. It’s also sometimes used as a slur against trans women and transfeminine people. As a term, it has its roots in that perfectly horrible trifecta that seems to dictate toxic masculinity: misogyny, homophobia, and transphobia.

But for some people being a “sissy” isn’t an accusation to defend oneself against. Instead, “sissy” can be a kinky headspace, a sexual role to take on, or even an important part of one’s identity.

So, let’s talk about sissification kinks and what it means to be a sissy. We’ll explore the eroticism in sissification fantasies, the ways sissification can look in real life, and how you can start exploring being a sissy if it appeals to you.

Along the way, we’ll dispel common myths and address some of the harmful ideas that circulate in sissification spheres.

This is Dr Abigail Dotson. I am a psychotherapist, psychologist and consultant. I have worked with more than 100 people to help them understand who they are and what personal questions they need to answer. Please comment on the blog with your feedback and questions.

Question #1 - Is this person a sissy? Why or why not?

Crossdressed as Brolitas

Crossdressed as Brolitas: Once a month, three longtime friends – Chris, Kenji, and Vincent –transformed an ordinary afternoon into something magical. They proudly called themselves Brolitas, a playful tribute to their love as men for the elegance and charm of classic feminine Lolita fashion.

On this sunny day, they gathered in their local garden park, dressed in their finest: soft florals, cascading lace, and lacy skirts that fluttered with every step. Kenji adjusted his multiple petticoats, Chris smoothed the pink bows on his pastel dress, and Vincent – ever the quiet one – poured the first cups of tea.

Their tea parties were about friendship, expression, and the joy of stepping into beauty together. They savored pastries, shared Lolita styling tips, and laughed over who spent the longest perfecting their outfits – especially teasing Kenji about how many petticoats he usually wore.

As the afternoon light softened, the three Brolitas clinked their teacups – grateful for a tradition that had begun drawing other like-minded Brolitas into their growing circle of tea gatherings. Which style of Lolita dress would you wear to a tea party?

Sissy Annie wearing the frills and having an elegant afternoon tea with Mistress Aimee!