Gentle Sissy Playtime: Getting You Prepared – Part 1

Everywhere my slutty eyes look, people are catering to hardcore sissy training. It’s wonderful! The way Mistresses mold you into the perfect little fuckholes for lecherous men of all body types is just dazzling to me. 

But being a sissy is about more than transforming into a ravenous harlot, or rather, it is to some.

I’m not the best at defining what I mean without a little help from examples. So, relax with me as I share my fantasy about giving you some gentle sissy playtime that you’ll never forget. 

Preparing Your Body For Full Sissy Immersion

Most sissies have been neglected in this area without even knowing it! Of course, you’ve been dressed in all types of lingerie, perhaps even while receiving your daily dose of humiliation. Still, the act of dressing you, in itself, deserves to be almost ritualistic sometimes.

 Scrubbing you down in a lavender bubble bath to wash away society’s masculine expectations and coat you in a base layer of soft feminine essence just makes sense. 

I want you in the right mindset to experience the wide range of feminine pleasure that can be found through gentle sissy playtime. So, as I carefully towel you off and prepare your body to be clothed, I slowly stroke your clitty. I don’t squeeze or palm it like a straight woman would, but rather, I treat it delicately like a lesbian exploring a new lover. 

Giving it an intimate kiss before I rise, I look up at you and wink. You’re in for a treat! My hand reaches for you, drawing you into my wardrobe. You giggle as I pull you through rows and rows of soft pastels; pink, purple, red, and white brush against your smooth, nude skin as I guide you to my 


Your eyes widen as you look at my precious sissy garments. But I’m not ready for you to be overwhelmed quite yet, so I help you pick out your dress, stockings, shoes, barrettes, and jewelry. 

Dressing You For Fun!

I choose a pastel purple and white plaid dress that looks straight from Dorothy’s closet. It seems fitting as we were about to be leaving Kansas behind for a more colorful world. I drape the dress over your arms, and as it settles there, you notice the white tulle peeking from below the hem. I giggle at your reaction as you run the netted fabric between your hands. 

However, my mind focuses on selecting a pair of brand new over-the-knee stockings with frilly white cuffs at their tops that are just darling, and perfect for gentle sissy playtime. I add them to your arms and grab a pair of purple Jimmy Choo’s and a butterfly hairclip to finish the outfit. 

I can already see it on you, and though it’s lovely, there’s a slight problem. The dress flares at the waist so you’ve clearly been neglecting your corset training! Knowing that we’d need to find you the perfect panties anyway, I pull you into my bedroom and make you take a seat on my bed. The pink canopy above draws your eye as you wait for me to put you together for our gentle sissy playtime. 

It doesn’t take long. I return to you with a simple underdress corset and a pair of lacy white panties in hand. 


I hope you enjoyed part one of my gentle sissy playtime story. If you can’t wait until Thursday for the juicy conclusion you can purchase my audio blog on my store. And if this story is hitting all the right notes for you? Be sure to check out “Crossdressing Sissy – Sophie’s Playmate Part One” by my friend Sophie!

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