Jim is acting under the direction of an online Dom and becomes subservient to his ex-girl friend. Things ended when she cheated on him and belittle him for having a small penis. They still live together and now Jim is directed to wait on her hand and foot, cleaning the apartment, making dinner, doing the laundry, etc. He was challenged by his Dom to convince her that being his keyholder would be a good idea and she surprisingly agrees, telling Jim she will not be nice. She feminizes him, having him shave his legs and cut up all his male underwear to be replaced with feminine panties and stockings. She sets goals for release on a weekly basis, including humiliating tasks and giving blowjobs to her gay male friends. Jim quickly slips into becoming a full sissy which delights his online master and his ex girl friend. He is submissive and aroused by shame and humiliation and offers little resistance as he becomes more and more of a sissy.

Chapter 1: Introduction

"Alright, Jimbo, here's what you need to do." The online Dom's deep, resonant voice soothed me through my earphones. "You'll find Emily's requests will vary. It's all about pushing your boundaries and fulfilling her more dominant desires." I took a deep breath to steady myself, staring down at Emily's ridiculously high stilettos carelessly flung in a corner. I'd be dusting and polishing those tonight.

The thought elicited a sigh as I glanced around the living room, littered with wine glasses and boxes of unsorted mail. I had to admit, Emily did have excellent taste in footwear. A brief fantasy of massaging her perfect, pedicured feet flitted through my mind. I shook it off, returning to my mental checklist: cooking, cleaning, laundry, with an emphasis on impeccable service in my newfound role as Emily's live-in submissive.

The apartment had become my entire world.

Once a sanctuary for our love, it was now a battlefield where I was the sole soldier, fighting to keep up with Emily's demands. The scent of vanilla permeated every corner, a constant reminder of her presence, her power. I'd started wearing it too, a subtle cologne that made me feel closer to her, even when she was out, leaving me alone with my thoughts and the endless chores.

I'd just finished scrubbing the kitchen floor, my knees aching from the hardwood, when Emily swept in. Her heels clicked against the tiles, echoing like gunshots in the silent room.

I looked up, my heart pounding in my chest. Emily stood in the doorway, her eyes scanning the spotless kitchen with a critical gaze. She was dressed in a tailored suit, her hair pulled back into a severe bun, accentuating her sharp features. She looked every inch the powerful woman she was, and I felt a familiar flutter of desire mixed with fear.

"Jim," she acknowledged me with a slight nod, her voice cool and detached. "It seems you've finally learned how to clean properly."

I pushed myself up from the floor, wiping my hands on my apron.

"Thank you, Emily," I said, trying to keep my voice steady. "Is there anything else you need?"

Emily walked over to the counter, picking up the apple I'd left there earlier. She took a bite, her eyes never leaving mine. "Yes, actually," she said, chewing slowly. "I want you to make dinner. Something... special."

I swallowed hard, my mind racing. Special? What did that mean? Before I could ask, Emily continued, "And Jim, don't forget to wear the outfit I left on the bed."

My stomach dropped. The outfit.

Of course, she'd left something for me to wear. I tried to keep my expression neutral, but I knew my cheeks were flushing pink. I couldn't help but picture the lacy lingerie set she'd laid out - a bra that would barely contain my chest, panties that would leave little to the imagination, and stockings that would make my legs look miles long.

Emily watched me, a small smile playing on her lips. She enjoyed seeing me squirm, I knew. It was part of her game, her power play. And I was learning to play along, despite the butterflies in my stomach.

I nodded, "Of course, Emily. Anything you wish."

She finished her apple, tossing the core into the trash can with practiced ease. "Good boy," she murmured, her voice softening slightly. Then, she turned on her heel and left the kitchen, leaving me alone with my thoughts and the task at hand.

I let out a shaky breath, leaning against the counter for support. Good boy. The words sent a thrill through me, a mix of pride and humiliation that I was starting to crave. I pushed off from the counter, steeling myself for the evening ahead.

I stripped off my apron, letting it fall to the floor. I'd pick it up later, along with any other stray items Emily might deem deserving of my attention. For now, I had a mission.

I made my way to the bedroom, my footsteps echoing in the quiet apartment. The door creaked open, revealing the room bathed in the soft glow of the setting sun. The bed was made, the sheets smooth and taut, a stark contrast to the chaos of the rest of the house. On top of the comforter lay the outfit Emily had chosen for me.

I picked up the bra, running my fingers over the delicate lace. It was a deep shade of red, almost the color of blood, and it seemed impossibly small. I held it up, comparing it to my chest, and felt a wave of doubt wash over me. Could I really fit into this?

I took a deep breath, reminding myself of the online Dom's words. *This is about pushing your boundaries, Jim. Embrace the challenge.*

With trembling hands, I unbuttoned my shirt, letting it fall to the floor. I stepped out of my jeans, standing naked in the middle of the room.