Training of a Sissy, Part One

Many years ago, you found yourself at the door to your dreams.  A mistress’ door, to be exact. You had been researching online for years and finally decided to embark on training. Training to be a sissy.  This was a dream you held quite close to your heart and never shared with anyone, until now.

You took a deep breath, your hand trembling as it hovered over the doorknob, glossy from years of use. It was an old Victorian house tucked away on a quiet street, the kind of place that seemed to whisper secrets through its ivy-clad walls. You had spoken to Mistress Tia only through messages and emails, and her words were always stern yet strangely comforting.  She had outlined what this training would entail with meticulous care: submission, transformation, obedience.  All the things you dreamt of and desired.  Mistress Tia was going to make your sissy feminization fantasy dreams come true, you just knew it.

As you pushed the door open, a wave of floral-scented air greeted you, mingling with a faint trace of incense. The entrance hall was dimly lit, adorned with rich tapestries and antique furnishings that spoke of a refined taste and a certain decadence. You heard the soft clicking of heels approaching and then she was before you—Mistress Tia.  Her presence was commanding; she was taller than you had imagined, her eyes sharp and discerning.

“So, you finally arrived,” she remarked, her voice smooth and measured, hinting at both curiosity and an underlying authority that immediately made you feel both anxious and yet inexplicably at ease. “I trust your journey was not too trying?”  You nodded, unable to find your voice, the reality of the situation setting in more profoundly with each passing second.  You instantly felt small and vulnerable standing in front of her.  You were completely awestruck by her beauty.

Mistress Tia smiled faintly as if she could read every thought racing through your mind. “Come,” she said, turning on her heel and leading you deeper into the house. Her movements were graceful, almost cat-like, making her black silk dress ripple like a shadow following her.  As you walked behind her, you passed several closed doors, each one fueling your imagination about the secrets they might hold. Finally, she stopped before a heavy oak door, pushing it open to reveal a room that was surprisingly bright and airy compared to the dim ambiance of the hallway.

Get ready for training, sissy

“This will be where your feminization training begins,” she announced as you stepped inside. The room was set up like a luxurious boudoir, complete with a large, ornate mirror, plush velvet seating, and an array of sissy attire meticulously arranged on elegant hangers and in polished drawers. The walls were a soft pastel pink, decorated with framed portraits of beautiful, poised sissies in various states of dress and undress—each one an exemplar of the art of feminization.  You paused to wonder where each of these beautiful specimens was now and were they all trained by Mistress Tia?  How and what did you have to do to become a portrait on her wall?

Mistress Tia gestured towards a satin-covered chaise. “Please, make yourself comfortable,” she instructed as she perused a small clipboard that seemed to contain notes about your upcoming training sessions. As you sat, the fabric caressed your skin, reminding you of the new sensations you would soon learn to appreciate even more deeply.

She set the clipboard down on a mahogany desk and turned back to you, her gaze penetrating. “We shall begin by discussing your goals and limitations. We must build this experience on trust and clear communication.”  “The forms you filled out online were merely psychological evaluations so that I could be sure you were mentally stable to begin such a journey.”  “Do you understand me, Samantha?”

You swallowed hard and blushed as she used your agreed-upon sissy name for the first time.  You nodded as she continued “Your dedication to embracing your desires brought you here, and it’s important that you fully engage with the process. Every step, every lesson, is designed to help you explore and affirm your identity as a sissy.” Mistress Tia paced slowly back towards the desk, “For our initial session, we’ll start with something simple—dress and demeanor. You will learn how to carry yourself, how to curate your movement to reflect grace and submission.”

She opened one of the polished drawers and drew out a delicate, lace-trimmed maid’s outfit. “This will be your uniform for today,” she said, laying it out on the velvet chair next to her. She also produced a pair of glossy, patent heels that matched perfectly with the outfit. “Putting on your attire will be the first step in understanding your role.”

As you stood and approached the outfit, Mistress Tia watched you intently. “Every piece of clothing, every accessory you wear, will teach you something about yourself,” she explained. “The way the fabric feels against your skin, the balance required to walk in these heels, and the posture you must maintain all contribute to your learning.”

You moved to touch the fabric of the maid’s outfit, feeling the intricate lace under your fingers. It was more than just clothing; it was a symbol, a tool for transformation and a perfect example of submission.

Mistress Tia continued, “Dressing is not merely about appearance; it’s an act of commitment to your role. You will dress meticulously, with purpose and care. Each time you put on an outfit, you reaffirm your dedication to this journey.”  “Let’s begin.”

Notes:  I’ve spent a long time working on this sissy story (it’s quite long) but I wanted to be able to include ideas and feminization fantasies from all of my sissies out there.  So, please feel free to write in and add anything you would like included in this ongoing saga.  I intend to make this a very lengthy project and all of your collaboration will help immensely.  What would you like to see/hear about happening to Samantha next?  What sort of sissy training would you be most interested in reading about?