Chapter 3: A New World

At work, the first few weeks were the hardest. For a month, I was managing the office on my own, with difficulty. The sisters had been very productive, and I was caught off guard by how much of the workload they handled. Then, I hired two more employees, a man and a woman, both very capable. I invited Bailey to come meet them, just to reassure her.

Leila, a grandmother, had custody of her daughter’s ten-year-old boy, and Duncan, despite his youth, was a diligent worker. I was happy to give her an altered schedule so she could be home early after school to watch the youngster. In her 50s and flat-chested, Leila posed no concerns for my wife. And she powered through her tasks impressively.

I returned home in a positive mindset, ready to play with my son with a smile on my face. In our bedroom, it was a different story.

After our first confrontation, our relationship had been icy. She refused to be touched or kissed, and only allowed me to see her in a neck to floor thick flannel nightgown. It might as well been made of bricks. I began to wonder if all of her threats were made in the heat of the moment. But her coldness spoke of her resolute fury.

Then one night after Danny was in bed, the calm before the storm ended. Bailey stood in the center of our dimly lit bedroom, her arms folded across her chest. I knelt before her, my hands resting on my thighs, eyes lowered. The silence stretched between us, heavy with anticipation and something far more potent—my guilt.

“We’re going to go over everything one more time. Start at the top,” Bailey commanded, her voice smooth and her expression stern.

I swallowed. “I betrayed you, mistress.”

“And?”

I swallowed. “And I want to make it right, mistress.”

Bailey tilted her head, considering me. I had confessed everything days ago—my indiscretion, the way guilt had gnawed at me until I could barely sleep. She had been furious, devastated. But then, something had shifted in her. If I wanted to stay, if I wanted to prove myself, I would do it on her terms.

“Take off your clothes.”

I hesitated only for a breath before reaching for the buttons of my shirt. I stripped down methodically, piece by piece, until I knelt before her bare and vulnerable.

Bailey stepped closer, lifting my chin with two fingers, forcing me to meet her gaze. “You don’t get to take anymore, Roger. You will give. Do you understand?”

“Yes, mistress.”

She smiled, slow and knowing. “Good. Now get on the bed.”

I obeyed, my pulse pounding. I wasn’t sure if it was fear, arousal, or both, but as Bailey climbed over me, straddling my waist, I knew one thing—I belonged to her now.

And I would do anything to prove it.

Bailey traced a single finger down my chest, her nails scratching lightly against my skin, sending a shiver through me. She watched the reaction with satisfaction, leaning in until her lips were just a breath away from my ear.

“Are you afraid?” she whispered.

My breath hitched. “No, mistress.”

A sharp slap landed on my inner thigh, making me gasp. “Try again.”

I exhaled shakily. “Yes, mistress.”

Bailey smirked. “Good. Fear means you understand exactly what’s happening.” She sat back, taking her time to admire my restraint, the way I held myself still, waiting, yearning. “Tonight is not about you, Roger. It’s about me.”

I nodded. “Yes, mistress.”

“Not just tonight,” she corrected. “From now on.”

Her fingers trailed lower, teasing, testing my patience. She saw the way my hands gripped the sheets, how my body trembled beneath her. “Do you think you deserve this?” she asked, tilting her head.

“No,” I admitted. “I deserve more punishment, mistress.”

Bailey’s smile was wicked. “Then let’s begin. Get on your hands and knees.”

She produced a paddle and whomped away until my ass felt blistered. I gritted my teeth and endured it without complaint.

A few weeks passed. At her direction, I was making dinner wearing only the apron, with my ass exposed.

“You overcooked the vegetables, Monkey!”—her favorite name for me now. “Get on the bench!”

I was wearing only boxers, which I knew to take down. All my tighty-whities were long gone, trashed in favor of boxers. She’d gone through them and scissored out the snap fasteners, leaving the fly gaping and exposing my dangling dick.

In our bedroom, we had a padded bench at the foot of the bed. I would sit there to put on my socks and shoes. Now, it was moved out enough so I could straddle it with my legs apart. My chest rested against the fake-leather surface and my cock and balls hung out off the end.

For serious misdeeds, the first step was handcuffing my hands together under the bench, leaving me unable to escape. Then, along with whipping, she would punish my poor dick or squeeze my balls hard enough to cause terrible pain. She had a leather strap, a cane made of flexible wood, and another paddle with holes. (The holes let the air whistle through, making each strike easier.)

On the other hand, on a day that I pleased Bailey, I got light slaps with her bare hands and loving squeezes of my butt cheeks.

After the more severe punishments, Bailey would demand sex, always with her on top. If I ejaculated before her orgasm, I had to eat pussy until she was satisfied. I also earned a severe whipping the next night.

Where did all this come from? One night, a few weeks into the new regime, Bailey explained her “going to the dark side.” While I was neglecting her, she was looking around the internet for “inspiration” to aid with masturbation. Inevitably, she found all kinds of BDSM stories and videos. Her lusty reactions surprised her. But it seemed the internet offered a 9 to 1 ratio of men dominating women.

She became enthralled when she encountered captivating scenes and tales of women dominating submissive men and even households. She actually overdid jilling off to the point that her clit got sore, and she had to lay off for a while.