Sissy Beginnings - Questions, Desires, and Willingness to Work

Broaching the topic of sissy play can be daunting, especially for first timers, both male and Female.

The best attitude to take when a significant other, pet, or partner talks about sissy desires is one of openness.

Ask questions.

Be attentive to detail.

Be sure to exude and cultivate safety and security during all conversations.

I emphasize this because there is no way to understand or enjoy a fetish without first understanding where the enjoyment of that fetish comes from, both for You and your partner.

He will be nervous - and You may be slightly confused or thrown off balance - but the only way to move forward is without ambiguity.

Questions are the foundation of understanding where to start and how to move forward in exploring this new-found interest.

The more You learn about his own fantasies the more You’ll become aware that there is room for an immense amount of imagination, pleasure, and enjoyment for BOTH of you within a sissy play context.

Certain questions to ask that will bolster your understanding of his sissy desires, fantasies, and needs are as follows:

“What was it about Sissy Play that first appealed to you?”

“What types of memes, stories, and scenarios have you come across that you find to be most exciting?”

“What type of clothes are you attracted to when you think of dressing up as a gurl?”

“What are some of your own specific fantasies involving sissy play?”

“Are there particular fabrics, sensations, or items that excite you, when dressing up?”

“Have you ever thought of shaving, tweezing, and other modification type activities? If so, have you enacted any, or would you like to?”

“Do your fantasies involve women, men, or both?” (This question can be broached either at the outset or farther into the time during which you are both exploring his sissy desires. Often, the desire for one gender or the other’s involvement outside Your immediate control can fluctuate.)

The above questions are a jumping off point, and yes, they sound a bit academic. I trust that anyone reading will be able to tweak these questions to fit their own style of sissy-sleuthing. They are, by no means, a comprehensive list of points to discuss, nor are they all going to apply to every sissy. However, never be afraid of trial and error, especially when it comes to examining and discussing fantasies. More questions are ALWAYS better than too few.

Questions let him feel safe and to show him that you are interested in understanding his desires.

The greatest asset to a Dominant Female is a thorough understanding of her submissive. With a man who craves sissification, this is overwhelmingly true. He will, most likely, not fully understand his desires, himself.

This is not a bad thing.

If your partner is coming to you and discussing sissy curiosity, it is highly likely that you are the first person to whom he has expressed these desires.

Consider Yourself honored - it takes a very special Woman for a man to feel safe enough to disclose fantasies such as those involved with Sissy Play.

Along with that honor, don’t feel pressured to indulge every fantasy. Keep control and feel free to ask many, many questions and help him get to a point of knowing exactly what it is he wants. Then, sift through his desires and examine which appeal to You, his Mistress.

Next, You can refine a list of potential activities that satisfy both of Your needs. It’s not a one way process of him asking and you giving. On the contrary, you, as the Woman, have every right to mold him into your ideal Sissy.

Not only is it Your right to mold, guide, and lead, but it is essential to the process of him giving up control of his dress, affect, and sexuality as a Sissy. With You in control, he attains the freedom to feel safe when enacting his desires to feel, look, and BE feminine.

The process can’t happen all at once, and often it behooves the Domme to give Her sissy goals to attain each subsequent level of play. 

This can be a gradual escalation of physical modification followed by piece-by-piece building of lingerie wardrobes, or be as simple as allowing him to pick out one item of makeup at a time and having to earn the privilege of learning how to use each item over the span of a few weeks.

Every sissy needs to work. The effort reinforces the value of his transformation and the value of the time and attention being paid to that transformation by the Domme.

Remember: ask questions, listen, and insist on his personal examination of his desires.  Sissy play must be based in honesty and the ability to work hard in attaining transformation from masculine to Feminine.

Your job, as Mistress, is to cultivate Your sissy’s desire to become ever more dedicated to that transformation.

To be continued…