What is Sissy Play?

by Jess

on 15 Jun 2018

First Thing's First, What's a Sissy?

Let's start with the Oxford dictionary definition...

Sissy Definition (noun): Derrived from the word "sister", a "sissy" is a person regarded as effeminate or cowardly.

Synonyms: weakling, coward, wimp, wuss, pushover, effeminate, unmanly, womanish

Now, without getting hung up on the social political correctness (or lack there of) of it all, and why "wimp" and "woman" are synonymous...


...let's break down what this means for sex play.

Keep reading to find out more...

What is Sissy Play?

Sissy play is a form of power play used to enhance BDSM scenes.

It's a way of creating a strong power dynamic between two or more people and relies on gender stereotypes to work.

Generally speaking, sissification or sissy training is the process whereby a submissive man emasculates himself, and takes on personality traits or roles usually associated with women.

He effectively becomes a caricature of what a woman is, based on societal stereotypes.

This can include anything from wearing a dress and tights, to softened body language, wearing lots of pink, or only responding to a feminine name. It generally delves further than simply crossdressing.

What takes place during sissy play depends entirely on the submissive partner's chosen sissy role.

For example, a 'Maid Sissy' cooks, cleans and wants to take on domestic chores.

Some sissy play is a form of humiliation, while other sissys concentrate more on the role reversal, age play and gender bending aspects of this roleplay.

Why Do People Do it?

Power exchange is HOT.

Not only does does power play require complete and utter trust from both/all parties, but the act of stepping outside of your usual role/headspace offers healthy escapism and an opportunity to learn something about yourself, as well as your partner(s).

The long term benefits of power play within a relationship (when explored safely) include improved intimacy, greater trust, more open communication and, of course, a banging sex life!


Aftercare is always important after any serious sex play, such as BDSM.

All power play can lead to heightened emotions, and it's quite normal for a sub to feel overwhelmed with feelings after an intense play session, especially if humiliation or sadomasochism is involved.

If your Sissy Play session involves someone who identifies as a woman in everyday life, it can be especially important for them to have a good aftercare chat, no matter which role they played in the scene.

As mentioned earlier, Sissy Play relies on societal stereotypes in order to work. Unfortunately, some sections of society still paint women as 'weak', 'emotional' and 'less able' than men, which most women aren't exactly cool with.

Bringing real life societal inequalities into play can leave some players feeling inadequate, downtrodden or sad, as it can bring real life difficulties to the surface.

It's for this reason that it's really important for couples (particularly straight couples) who use Sissy Play in their sex life to talk afterwards, and reiterate that defining gender is clearly far more complex than these outdated ideas.

Try it for Yourself - Sissy Play Must-Haves:

  1. Classified Miss Alice Costume

    Classified Miss Alice Dress

    Perfect for Prissy Sissy Play. Combine with stockings, a big petticoat and lacy gloves for first-class fussy girl play.

  2. Lovehoney Fantasy French Maid Costume

    Lovehoney Fantasy French Maid Costume

    The ultimate outfit for Sissy Maid Roleplay. Pick up a feather tickler duster and stockings to finish the look.

  3. Desire Long Wavy Brunette Wig

    Desire Long Wavy Wig

    Girls have long hair: Fact*. These wavy locks'll transform any bloke into a hair flipping sissy in a snap.
    *According to society.

  4. Lovehoney Opaque Red Bow Stockings

    Lovehoney Opaque Bow Stockings

    Great for guys who don't want to shave, slip these ultra-feminine, red-bowed stockings on to feel leggy and ladylike in an instant.

  5. Sex & Mischief Pink Lips Mouth Gag

    Sex & Mischief Pink Silicone Lip Gag

    For those who take sissy play further than dress up, this open mouth pink lip gag is great for submission, humiliation and coerced sissy play.
    Also available in red and black.

  6. CB-6000S Short Pink Male Chastity Cage

    CB-6000S Short Pink Male Chastity Cage

    The bondage version of 'tucking', take your penis out of the picture with this pink cock cage. It prevents erections and growth for ultimate feminization, whilst allowing ejaculation and urination.

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Written by Jess.

Originally published on 15 Jun 2018. Updated on 5 Aug 2020