"Newly discovered persona,” she said.

Jess’s choice of words was never accidental. This previously concealed aspect of my character was now on full display. I was not playing a role, this was not contrived, this was me, an emerging new identity.

So there I stood, her words still melting into my ears, her breath lingering on my skin. Challenging me to declare aloud the reality she already knew.

Looking in our full-length cheval mirror, I once again admired my pretty pink underthings. Quickly I attempted to reflect on what had led me to this moment, in hopes it may provide thoughts on a path forward.

For most of my life, I had considered myself straight. I would watch porn and assumed most men did. I was of course in a way always impressed, even fascinated by the significant size of the men’s cocks, but of course, I was straight.

One day while browsing for something to watch, seeking something with “two guys and a gal”, I stumbled across some scenes involving shemales. Over several weeks I watched and masturbated admiring the sexy femineity. Over a brief time, this led to further searches and I soon found myself increasingly viewing videos with feminized males. “Sissy”, they were called. Men, dressed as women, being used and treated like women! I could never be a transgender female or “shemale”, I thought, but it was not a stretch to think I dress feminine and pretend.

One afternoon while alone in the house, I went to Jess’s closet and stripped naked. Unsure what to try but craving the need to feel feminine. My eyes found her red silk kimono. Slipping my arms into the smooth soft fabric, feeling the silk cascade on my shoulders, and back, sent shivers through my body. My immediate reaction was a swelling between my thighs. I found a pair of lace red panties she had worn the day before, discarded in her hamper. Picking them up I noticed a slight stain on the gusset, held them to my nose, and inhaled. Her scent was present and was a perfect addition. Sliding her panties over my thighs my cock began to ooze precum.

I looked into the full-length mirror. The visual of red silk to my mid-thigh, red lace caressing my crotch, combined with the scent of pussy in my nostrils was incredibly sexy. My throbbing man parts continued to grow and leak, testing the limits of the panties for any weakness.

“This looks good,” I said out loud, though no one was there to hear it.

The protrusion in her, or rather my panties needed some attention. There was a dark wet spot growing as the bulbous head strained to escape its lace confinement.

Our office was just across the hall from the bedroom. My body felt like it was floating as I made the short journey to the hardwood desk.

In no time, the screen was filled with the image of a sissy in thigh thigh-high boots, and a crotchless lace body stocking. She had a modest-sized cock, but it was hard and ready. Her voice was soft and feminine, she moaned as her hands massaged her shaft, pumping the full length slowly and deliberately, a finger sliding into her sissy hole.

My body reacted. I found my hands sliding along my skin, touching my chest, nipples, abdomen, and thighs like a female lover would touch her partner. Carefully only grazing my throbbing member, knowing it would not take much to make me explode.

The star of my screen, this beautifully sexy feminized male was inspiring. I watched, sensing the imminent finale, as she slid a finger deep inside herself while more vigorously stroking her cock. Her orgasmic moans filled the room as she erupted. My hand instinctively reached for my throbbing shaft. Initially, my thought was to delay my release, but it was too late. Twitching and moaning I burst with a flood of cum, filling and overflowing the lace of my panties.

That is how it began, and of course, evolved. Jess’s wardrobe didn’t quite fit so stealthily, I had made a few panty and bra purchases of my own. Increasingly frequently wearing feminine underwear. Taking greater risks to feel the lace on my skin. Wearing these at work and around the house, thinking no one was the wiser. Stealing moments to slip into a sexy pair of panties, was no longer enough. It soon became panties, a sundress, lipstick, and a wig when I was alone at home. Always hard as a rock from the moment I slid the lace over my thighs until I inevitably came in my panties and reluctantly removed them.

My porn viewing selections were now exclusively cross-dressing, sissy, and feminization themed. My fantasy life became centered around these themes. I could no longer masturbate without at least panties on. These drove cravings. Cravings I had not yet fully explored in my mind, much less expressed, but a constant craving to dress and be used as a female was undeniable.

In my need to feel feminine, I likely wasn’t as sly as I had thought. Jess had discovered I was dressing in her things and found my secret stash and my viewing history. Did I leave a trail of breadcrumbs? Perhaps I had wanted to be found out.

I had to admit strong feelings were stirring inside me. Here I was standing before her, being charged to wear lacy things of her choosing. She had projected no anger but rather a firm necessity for being open. It was clear she felt the need to chastise me, even humiliate me, but that seemed playful in its style. A sensation of both excitement and relief washed over me. I knew what I was, and what I needed, and I smiled.

“I’m a sissy,” I said without shouting. Loud enough for her to hear, yet I was not surprised at her reply.

“I’m sorry, I didn’t hear you,” she said, relishing her newly found dominance over me. “You will need to speak louder if you wish to please me!”

“I am a sissy. I am a sissy that loves sexy lacy things,” I continued with more conviction, seeking her approval. “I crave feeling feminine. I want to be fully trained as a pretty little sissy!”

Jess leaned forward, her lips curled and a devious smile and a cunning glint in her eyes. She slid a hand inside my panties, teasing me with her fingertips. I was quivering with delight and moaned at her touch.

“That’s a good gurl,” she whispered into my ear. “Do you think you have been good enough? Should I let my little sissy cum in her panties?”