Gentle Sissy Playtime: Getting You Prepared Part 2

The questioning look in your eyes makes me want to reassure you, sweet sissy, so I carefully rest the contents of my hands on the bed beside you. I need them free, so I can frame your vulnerable face as I meet your gaze. My thumb grazes your lip, and you shudder, goosebumps rising on your arms. 

If I don’t look away, we’ll never get you dressed! So I take my hands back and pick up the corset. 

You stand, knowing what comes next. Already loosened, I raise the corset over your outstretched arms and shimmy it down over your waist. With a few adjustments, it sits in place, looking a bit boxy. Not quite the look we’re going for during our gentle sissy playtime…

Spinning you around by your shoulders, I turn you until your back is to me. As I gather the strings to tighten you into shape, I lean forward, kissing each shoulder in turn, before slowly tugging your strings. 

Not wanting you to be uncomfortable for our playdate, I take my time lacing you in. My light kisses pepper your shoulders and neck each step of the way. By the time I finish, your clitty is dripping, and a mewling pant is escaping from between your lips every now and then. 

Finishing Touches Of Phase One

Instead of spinning you back around once your laces are tied, I walk around you, taking in your improved curves. They look perfect for gentle sissy playtime! I present your panties to you, an eyebrow raised in question, wondering if they’ll even fit now that you’re aroused. I love seeing the sass as you roll your eyes and grab the panties out of my hands. 

With a huff, you step into them and adjust your clitty until it fits, and then look at me triumphantly. I clap excitedly at your success and then grab the dress off of the bed. 

“Arms up!” I command before lifting the dress over your head. Expecting me to pull it all the way down, you gasp when my hands abandon the dress and instead seek out the top of your panties. My nails lightly rake across it before dipping down to flick the tip of your clit. Arms and head trapped in your dress, there’s nothing to be done but enjoy the sensations as I press our bodies together.

Teasing The Sissy

I tease you a little more, letting my other hand trace a line up and down your ass. I can feel the tight ring of pussy-muscle pulsing beneath your cotton panties and have to indulge in a few light probes, sissy. Your desire overwhelms me, though, and I have to step back. It’s not the time for that yet!

I take a deep breath and finish lowering your dress. With only a few final touches left before we move on to hair and makeup, I draw out the act of helping you into your stockings. With a hand, I guide you back to my bed, and you sit on the edge. I lower myself to my knees in front of you and pick up one of the stockings. 

I open it for you and slip it over your toes. Straightening your leg, I let my hands slide over the material as it makes its way to the middle of your thigh. Once it’s entirely in place, I run my hands back down your legs and add the purple high heel. You’re a naughty little sissy, aren’t you? I can tell it feels good as I repeat the process on your other leg and stand. Looking down at you in your perfect sissy outfit, my heart fills with excitement. There’s so much to look forward to still, now that we’re ready to move onto phase two of preparing you for gentle sissy playtime.


I hope you enjoyed part two of my gentle sissy playtime story. If you would like to hear my sexy story narrated for your enjoyment, 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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