I Feel Pretty: A Guide to Sissy Play

The highly broad term of "Sissy/Sissification Play" refers to a variety of interests within the fetish-world that focus on consensual emasculation and feminization, most commonly at the hands of a Dominant female partner.

(Note: Although we use male and female as an example in this article, sissy play can be done by partners of all genders and sexes.)

Sissy Play holds ample appeal amongst the straight male submissives in my community, but there is also, unfortunately, a great deal of hidden shame and judgment in the hearts and minds of these men when considering how to broach such an interest with their current (or hopeful) FemDom (female-dominant) partner.

I know this because, in my time as a professional Dominatrix (a female Dominant for hire), these are often the very insecurities I soothed for my clients.

As most every activity or fetish in the BDSM Lifestyle, the unique desires, and the personal, sexual, and relational expression of those unique desires, vary greatly from person to person. However, there are a few main categories from which to choose when considering any type of sissy or feminization play in your dynamic...

Crossdressing

Crossdressing refers to adjusting the submissive's style or their physical body, through waist-training, feminine clothes, wigs, shaving legs, having nails done/painted, etc. Those interested in the cross-dressing element of sissy play are also commonly aroused by the prospect of behavioral training to accentuate the crossdressing, such as using a softer voice, walking, sitting, and moving in more feminine ways, and even carrying typically female-gendered items such as a purse, scarf, etc.

This manner of behavior and dress can also carry over into a desire for tasks that have historically fallen to female-gender roles, such as cooking, cleaning, and domestic chores, and are often incorporated in a "maid training" capacity with humiliation and punishments.

Read: The Top 10 Fetishes You Didn't Know You Had

Sexual Denial

Sexual denial in the form of chastity and orgasm control is often quite arousing to hopeful sissies as well, as the feeling of sexual powerlessness further concretes their mind into a female experience.

And it is this desire that can lead to a highly requested activity in the FemDom world, pegging, where the female partner wears a strap-on dildo and penetrates her male partner anally, or requires "forced" oral service on said dildo, etc.

Read: Orgasm Denial?!! It's More Fun Than You Might Think

Why Are People Interested in Sissy Play?

These interests are often the result of a deep desire to "step into her shoes" both figuratively and literally and glean an intense sense of empathy to the female experience. Yet, this sweet desire to empathize and explore with their trusted female partner frequently goes unexpressed, and these desires never realized.

The good news is, I have helped over 230K people and their partners navigate this complex world in my YouTube video, "Sissy Play with a FemDom Partner," and it is that set of secrets that I'm going to share with you today!

How to Build Successful Sissy Play With Your Partner

As a former Dominatrix, I was approached by men on a regular basis who had this fetish, or a variation thereof. And that is my first point, men (and partners)… ditch the shame!

It is often this shame that binds people (and not in a fun way!) to what we in the BDSM Lifestyle call, "vanilla conditioning," or a set of limiting sexual beliefs developed by upbringing, culture, trauma, etc.

You're allowed to desire this type of play or expression in your trusted relationship, regardless of anyone else's opinions. Own that truth.

Some of the most beautiful moments in my professional practice occurred when my submissive males received permission to "go there" mentally and emotionally, often for the first time in their life.

Read: Practical Ways to Reduce Your Sexual Shame

These are the softer, more endearing men among us who have felt pigeon-holed into an overtly masculine way of operating that feels foreign, but the alternative thought also feels shameful. So, they feel trapped.

That is why you as the partner interested in this type of play, must own that truth, and trust that your female partner will receive your perspective with love, understanding, and compassion.

However, your partner may need to have a conversation with you about these desires, especially if this is totally new information, or if they have had no previous Dominant experience in your relationship or otherwise. At this point, they may need to ask a few questions simply so she may understand and empathize with you. In this case, I would encourage you not to receive such feedback as judgment, but as an opportunity for intimacy, or "into me you see," as I often phrase it.

Read: BDSM 101 Tutorial - The Importance of Communication

Part of truly stepping into the feminine experience through Sissification Play, allows the male partner to relate to their female partner's experience; her feelings, her perspectives, insights, etc. Therefore, gather your thoughts in a way that works for you, and share with your female partner not only (1) your specific interests, but (2) the way such activities make you feel, or at least how you hope they will make you feel.

Typically, kinksters are quite specific about their fetishes, so be clear on what it is that has caught your interest:

• Do you just have a desire for crossdressing?
• Or do you find full-time maid training arousing?
• Or is it just the thought of wearing pink lace panties over a chastity belt that excites you?

Essentially, use this as an exercise in communication and emotional intelligence, and share with your partner the "why" behind your "what."

Finally, I would encourage you to allow your partner to find the fun.

Just as your fetishes are specific so will your partner's feelings or interests as well. And you will truly feel the freest and be able to fully enjoy your sissy play when your partner is enjoying herself as well. She could really enjoy the prospect of going shopping together and sneakily helping you choose pretty undergarments to wear at work. Or, her hidden Degrader could come out and she could savor the humiliation aspect of sissy training. Even still, she could relish the element of sexual domination through pegging, or simply be pleased to witness emotional empathy in watching you sexually receive.

Read: 3 Scenes for a Beginner Femdom to Try

Regardless of the unique way you and your partner choose to engage in sissy play together, it absolutely has the potential to infuse empathy and intimacy into your relationship in a powerful way.

And to further help you and your FemDom partner do so, I have put together a blog post with a practical guide to helping your suppressed alpha female or shy switch step into her FemDom power!

Much Love and Happy Playing,
Ms. Elle X