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Sissy Playhouse

I was three years out of school and working as a stringer for several local publications.

My degree in journalism hadn’t propelled me into the life of luxury I hoped, but after some struggle, I had lined up a regular series of papers and magazines that would print my work.

The pay was lousy, the hours sucked but I did have the freedom to pursue material that interested me.

As a closet fetishist, I had taken a recent liking to pen stories about local clubs that were off the beaten path.

Sure I pursued the soccer fans at the only Irish pub in town and looked into the red hat ladies who met twice a month to drink tea on the southeast end of town, but I was also looking into the secret fetish clubs.

Until now, they were all a bit too far out for mainstream papers (I was stunned by the number of people in my metropolitan area who were into swinging and pony play).

But I knew I hit pay dirt when I stumbled on Samanthas Sissy playhouse.

From the website, I gathered that her home which doubled as the clubhouse was actually a place for local crossdressers (ranging from sissy to TV to full transgender) to come and be themselves.

We e-mailed back and forth and she was thrilled at the idea of having her business profiled.

The address was a secret, only available to those who requested it from her website, but she happily emailed me the location on my promise of keeping the playhouses neighborhood and address a secret.

For as long as I could remember, I had sissy tendencies.

I started as a Diaper Lover and Teen baby, but by the time high school concluded, my attraction grew to include women’s clothing.

By the time I finished college, I had experimented with everything thanks to the internet, although my actual dressing and real-life experiments were quite minimal.

Part of me longed to join Samanthas club, but I knew my high-profile job made any public display of sissiness impossible.

Still, a girl can dream . . .

At the appointed date and time, I drove up the lengthy, private driveway to a stunningly large mansion in the hills outside town.

I parked in the driveway and walked the steps, positive I had the wrong place until I saw a pink sign on the porch that read Samantha’s playhouse.

I rang the doorbell and before long, a gorgeous young woman answered.

This stunningly beautiful brunette introduced herself as Samantha and ushered me excitedly into the home.

Dressed in a simple pink summer dress with her hair pulled back in a ponytail, her natural beauty radiated from her petite, 5-foot-two frame.

We exchanged pleasantries before she asked me to sit in one of the chairs in the sunroom, a porch-ish-like area in the back of the house.

She offered me a glass of water before sitting. I set out my tape recorder and we began to chat.

As our conversation ran on, Samantha told me that the playhouse came about as she was studying for a psychology degree.

During a class on human sexuality, she realized that crossdressing, in its simplest form, is not necessarily a sign of homosexuality or the desire to be completely a woman.

It is merely a stress relief for men.

Like any hobby, there were myriad variations including some men who truly wanted to be women,

some who wanted to be treated as women,

some who were aroused by the clothes, and on and on.

She also realized that most men who dressed, did so in secret because there was nowhere acceptable for them to express this desire.

To serve that need, she had created the Playhouse.

A safe, discreet, completely anonymous place where men could behave as they wished, take their dressing to whatever real they liked.

My throat was dry as I listened, dying to grab her hand and shout yes! you understand! but I did not.

After about a half hour, she asked if I would like to take a tour.

I eagerly agreed and thats when she asked if I would like to try on one of her outfits . . . in order to fully experience the club.

Joking that it was for journalistic purposes only, I heartily agreed.

With that, Samantha led me to a room off the main entryway, inside were three private dressing rooms and the largest closet you can imagine, full of all things girly.

Costumes, dresses, lingerie, you name it and she had it. In all different sizes as well.

Samantha rummaged in the racks for a minute before handing me a simple pink sweater and denim skirt, pointing me into one of the changing rooms.

We giggled back and forth together through the curtain as I changed.

The skirt sliding up my legs and the tight sweater hugging my chest felt like heaven.

When I exited, Samantha applauded, telling me how cute I looked.

She took me to the room next door which was a full makeup facility complete with dozens of wigs.

She quickly fastened a simple, bob-cut brunette wig to my head and applied a light touch of blush and lipstick.

The smells were heaven and I could barely keep up the friendly banter we were having.

Samantha then lead me upstairs.

She explained that the downstairs was kept as a normal home but the upstairs gave the girls who visited free rein.

Each room we walked into was pure heaven.

A full dance studio with ballet bars and pilates equipment.

Bedrooms made up for a baby, toddler, and adult woman.

She explained that the girls liked to explore different fantasies and each playroom was designed to fulfill as much as possible.

She had stay-at-home moms who lived nearby come over while their offspring were in school to play with the club members.

Thet offered everything from diaper changes for the Abs to girl talk partners for the full-grown gurls.

When we finally got back downstairs, my head was spinning and I could barely walk straight.

Samantha asked if I wanted to share another drink with her or if I had to run right away.

Not wanting to leave I agreed and sat as she poured us each a diet soda.

So, Samantha suddenly asked will you be signing up for a membership?

I nearly choked on my drink and tried to play it off as if she were kidding.

She was not.

Sweetie, I can see it all over your face.

You may be a reporter, but I can tell you’re a sissy too.

From the way you’ve let your hands dangle femininely against your skirt to the way you just smoothed your skirt when you sat down.

I blushed uncontrollably realizing I had been having so much fun I had given myself away.

After a moment of prodding, she took my hand and gently told me it was ok . . . that this was a safe place.

I broke down, crying a bit, and confessed that she was right.

I told her everything, that I was one of those straight men who loved to occasionally be a sissy.

While I thanked her for the kind offer, there was no way I could afford the very steep membership rates (Samantha kept the rates high to make sure only serious members joined).

At that point, Samantha hugged me, took my hand, and lead me back to the front entryway.

She pointed to a small desk outside her office.

She told me that her dream was to make that desk a display case.

A place where a sissy she created could work as her assistant, greeting guests and serving as a testimonial to the wonderful impact of her club.

She would love to let me fill that seat . . . that is, if I wanted to.

The arrangement would be simple, I would take a one-week vacation from writing and come work for her.

She would give me lessons on how to be a proper lady and train me on the job as her assistant.

If at the end of one week we were both enjoying the arrangement, she would make me a job offer.

It took less than a second for me to agree and I was told to report first thing the next morning.

The following seven days were pure heaven.

Each morning I would arrive at seven and be welcomed with a hug from Samantha.

I would then enter one of the dressing rooms and put on the outfit she selected.

Tan tights every day to begin to disguise my leg hair.

Then panties and a simple outfit, typically a knee-length skirt and a longsleeved top.

She would then apply a different wig each day, letting me try looks from a tight bun to pigtails to a layered, Jennifer Aniston look.

Finally, my makeup.

Foundation, blush, and eye shadow. Macassar and lipgloss to complete the look.

From there we would go about our day.

Each guest had to give at least a half-hour warning which provided us time to lay out their outfit in the dressing room and prepare any activities she wished to participate in.

This week, each girl had the option of including me in her visit to which every sissy happily agreed, thrilled to have a playmate.

Some days, we would simply sit and talk in the living room.

Other days were a bit more adventurous.

Stacey asked me to join her dance class, taught by a friend of Samantha’s in the dance studio.

We both dressed in traditional ballerina outfits and worked through graceful, elegant princess-ish moves together.

Kathy enjoyed being a little girl and loved the idea of having a playdate.

Samantha dressed us both in diapers and short babydoll dresses, feeding us from bottles and changing us when we wet.

The week flew by and before I knew it, it was the last day of our experiment.

I hoped against hope that this would work out but silently fretted that the salary wouldn’t be enough to cover my rent or that perhaps Samantha was displeased.

We had booked that last Sunday afternoon out to be together, so we could enjoy some time alone and discuss the future.

As a special treat, Samantha offered to let me pick my outfit for the day.

When I emerged from the dressing room in that short pink babydoll she dressed me in to play with Kathy she giggled.

She said that outfit wasn’t complete without a proper diaper.

She lead me by the hand up to the nursery room where she laid me down, eased my dress up, and began applying powder.

She asked if I had fun this week and I nodded.

She slid the diaper under my bottom and taped it tightly before saying that she too had quite a fun time and would love to continue having me as her assistant.

But she stopped I don’t want you to be my employee.

My heart sank as I realized she would likely ask me to work part-time, for free as she couldn’t afford to pay me full time.

Quite the contrary.

She explained that her parents were quite wealthy and had given her a large sum of money to pursue her research.

Her father was actually a sissy as well and they felt her efforts were a great cause.

She then explained that she had grown to love me over the past week and hoped I would move in and be her sissy forever.

My jaw dropped and all I could do was cry from happiness.

Samantha hugged me tightly as I said I love you too over and over into her shoulder.


Six months later

Samantha and I didn’t waste time.

I gave notice to my publications, ended my lease, and moved my stuff in almost immediately.

My family was thrilled that I had found someone so well off so I could focus on writing my novel and her family loved having another sissy around.

I accumulated my own private collection of clothes.

But I also kept my boy clothes.

At my choosing, I could go out in public as a guy, meet my friends, even have them over (provided they stayed downstairs of course).

But when it was just Samantha and me, my male name Alex, turned into Ashleigh and I would run around the house.

We got married four months after our first meeting but held a second ceremony for the club members with two brides and no groom.

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