There’s a little place just on the outskirts of town, where  one can have a proper sissy dress-up date. You don’t know that. But I do.  You think it’s just another frilly ladies boutique. A quaint Victorian home, which sits back off the road on a large corner lot. You know the kind, with the inviting wrap around porch, the octagonal tower, never seen in home building these days. Dove grey with white trim, far from the home’s hey-day when vibrant colors were all the rage.  You probably never noticed the small nondescript iron sign post by the entrance of the driveway “Lola’s Dress Up Boutique”. I have, and I have been inside.


As we enter there is a long hallway. To the left a large airy room filled with racks of classic satin gowns, another section showed a more modern female look. They seem to have every genre of fashion! Hooks lining the walls supporting various accouterments. Purses, scarves, hats. To the right of that hall, a  remodeled drawing room, with the a large opened wall,  ornate arches honoring the homes heritage. The room is warm and  inviting . The air is fresh with a hint of lavender, and soft music is being played somewhere. The soft, far off notes, filling up the otherwise silence of the home. The drawing room is decorated Shabby Chic, I think they call it. Delicate details like doilies on the table, and exotic Persian rug decorating the hardwood floor, floral settee and chairs face the fireplace. Card table with other chairs in front of the window in the large front room.Sissy Dress-Up


Down the hall you are led. Doors dot the hall and have frilly fabric signs hanging off of pink ribbons, displaying the name of the room. You pass by the Princess room, Pretty In Pink, Classic, Sun~n~Fun,  Sassy and the last room, our room is named Debutante.

Sissy Dress-up

Your heart beating faster, palms are sweaty you feel a twitch in your trousers. Damn that cock, you scold yourself, you are only here to Help Ms. Erika pick out a gown for an event not to indulge your fantasy life.  You take a deep cleansing breath trying to force the thoughts from your mind.  As you enter the room, an assistant appears , seemingly from nowhere and greets us.  I confirm with her, yes we will have the tea tray, and I ask her if the room has been prepared per my request? She acknowledges that everything is as it should. We enter, and I close the door behind us.

Have a seat and I gesture to a seating arrangement in the corner of the large room. This room is also decorated ultra-feminine.  The one corner is draped off with velvet, floor to ceiling drapes, the dressing area you assume. Just to the right  a group of mirrors, all facing each other. When you step in front of them, you can see yourself from every angle.

Is This Really Happening

You sit on the bench, and I sit across from you. Putting down my purse, unbuttoning my blouse to further my ruse, then  taking off one of my shoes I stop halfway. I allow the shoe to dangle off of the end of my pretty stocking covered foot. Looking up at you, you are gazing at my shoe.  I ask you: Do you think we are really here to find me a gown? Instantly, your mind realizes what your cock has been trying to tell you since you walked in.Your head starts to spin, Mistress Erika is the only one you have ever told your secrets to, you’ve talked about doing exactly this time and time again. But you always felt you were not ready, are you ready now? You feel faint and want to protest, you have only played in fantasy like this. Never for real!  You fear what you might feel, do or want after being coerced and  totally transformed into a woman, you stutter out a few… bu.. but….ah…..Sissy Dress-Up

Putting my shoe back on I walk over to you, standing too close and I one finger, place it under your chin, lifting your head up to meet my gaze.  Shhhhh I whisper…… shhhhhhhh. This is what you want, what you need, just relax and let me guide you, let’s explore and discover what kind of a woman you want to be.  I’m thinking for your sissy dress-up style we should go more classic and elegant for you, humm?

What is your Sissy dress-up style, let’s go shopping!