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Miss Lola’s Sissy Dress-up Boutique

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!

11 comments to Miss Lola’s Sissy Dress-up Boutique

  • Petey cream puff

    With telling you about my fantasies in how much I like women’s clothes/dresses/boots/lingerie I I I didn’t realize there was this place. Just seeing all the purses/scarves/dresses along with the lingerie and women’s clothes. With scents of lavender along with feminine scents I’m really nervous that these items are for me as we are in dressing room and you are coming closer to me saying this is what I always wanted and needed. to relax as you sit on my lap and put your finger on my lips. Seeing matching maroon bra/panty set with pink slip and size 6 body con sheath dress on hanger I have feeling you had this all planned out for me along with makeup sitting on vanity.

    This will be happening to me in 2 weeks as my massuse & I will be going out of town for shopping trip. She said she wants me dressed in leggings/knee high boots/women’s turtle neck sweater/women’s wraparound scarve with pink purse I bough from her along with bra/panty. She to said to relax and not worry about being dressed as I’m with her. She said we need to buy burgundy lipstick along with Ralph Lauren midnight passion/passion perfumes/lotions along with me getting makeover done at Macy’s. I’m nervous but excited at same time. I know I’ll need to bring extra panties/panty liners as I know I’ll be hard and hope she doesn’t notice. Especially if I cum. Ms Olivia said I need to tuck. With this trip happening I’m defently her sissy boy as I can’t go back since I came out to her. This is what I needed and wanted and it’s finally going to happen. I’m really her cream puff sissy boy.

  • Erika

    Oh, Petey what a superb comment. You are such fun and I am sure you won’t hesitate to fill us in on your sexy shopping trip in two weeks. 🙂

  • Ohhh that’s a sexy story! Love the descriptive writing. There should be such a fancy boutique in every town for the local sissies. I love the fancy boutiques, being quite a collector of expensive panties. Only the best for the sissies! Great job with this!

  • Petey cream puff

    It’s amazing how much power bras/panties/slips/lipsticks/perfumes/lotions/makeup along with leggings/boots/heels/dresses have over me alon with women that are into it. Once I put in bra/panty/slip with heels/lipsticks/layering it with lotions/perfumes I was hooked and never wanted to take this off.😢😳😧. With shopping trip upcoming in 2 weeks I’m this really will happen. My massuse has me using same skin care lotion to keep my face so girlish soft. She has me thinking/talking and acting girlish. She said she only wants to see me happy and this shopping trip with her will do that. She has total power and control over me. With her telling me to come dressed in women’s clothes I belong to her and am her cream puff sissy forever.

  • faggotbritney

    MS ERIKA, as U know, my style of dress-up is more for exposing me as an obvious,perverted,weak sissyfaggot. i dream about this a LOT. Everyone will know soon how much U OWN & CONTROL me, wont they? Multiple dreams/fantasies cumming true for real for me……MS ERIKA is the reason why.

  • faggotbritney

    i know i wont sleep much tonight….too excited about being outed & exposed as YOUR BBC FA&%$$! i have had sooo many wet dreams in my life about being OWNED, CONTROLLED, EXPOSED, but not too the entire internet world!. i have been too much of wimp/pussy most of my life to go thru with it for real, but know, at 56 yrs old, i have accepted that i failed as a REAL MAN(miserably,obviously) & i want/need to be exposed for what i have ALWAYS meant to be. Tomorrow cant get here soon enough!!

  • Gem Sissy

    What a beautiful blog post! Once upon a time in my city there was an independently owned lingerie store called Heartline Lingerie. An older couple owned it and it was housed in an old two story house. I remember the rooms (living, dining) had racks after racks of lingerie and sexy dresses. I hadn’t shopped much by that point so I was crazy nervous. The ‘dressing room’ was a bedroom upstairs with a lot of room, mirrors for dressing and still had a bed. The whole store felt so warm and intimate. They didn’t protest to let a guy like me try on lingerie.

    I wish I’d had more money at the time to reward them. They eventually moved to a small commercial space on a second floor and eventually went out of business. I really wish I still had the sexy things I bought from them, but the purge-monster must be fed. Sigh.

    • Erika

      Thank you for the compliment. The store you describe is similar to what my ideal is. Something cozy, welcoming and personal. Where all are free to be who they are.
      Purging isn’t uncommon as you know. However seeing your post over at I’m hopeful purging is a thing of the past for you, right?

  • Gem Sissy

    Purging seems to be a thing of the past. I’m really trying to accept this part of me, have tolerable accommodation from my wife, and get to enjoy these sissy games. Of course, I’ve said that before and oh the $ wasted and very special lingerie lost. Hoping that is the past.

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