His Manhood Got Evicted

Jack had been out of work for months, always insisting he’d find something soon—after one more game, one more weekend, one more excuse. Caroline had grown used to coming home to the same scene: him on the couch, controller in hand, eyes glued to whatever mindless shooter he was wasting his day on. Eventually, she’d had enough.

She told him it was over. He begged—pathetically—claiming he had nowhere else to go, no job, no money. He even dropped to his knees, clinging to her like some helpless little puppy.

With an exhausted sigh, she relented. He could stay… but not for free. If he wasn’t going to get a job, he was going to work.

Jack figured he’d bought himself a few more weeks—maybe do some dishes, take out the trash, keep the peace. What he didn’t realize was that Caroline already had something very different in mind.

The next day, Caroline came home without a word, setting her bag down and walking straight over to where Jack sat nervously on the couch.

“Take your shorts off,” she said flatly.

Jack practically leapt to obey, his hands fumbling at his waistband. “Heh, I knew you’d change your mind, babe,” he said, grinning like an idiot as he pushed them down and closed his eyes, his soft, unimpressive penis twitching hopefully in the air.

Caroline rolled her eyes, stepped forward—and before Jack could react—click.

She stood back and admired her work: a delicate, pastel pink chastity cage now locked snugly in place. “Can’t have my new sissy maid getting any ideas. Until you find a job, Bella... you belong to me.”

“Bella? What the hell—”

“You don’t like it?” She gestured toward the door. “You’re free to leave. I’m sure the streets are very accommodating for jobless little boys with no backbone.”

Jack stared at her, jaw clenched. He wanted to yell, to run, to protest—but his options were gone. So he stayed… but only for now. He told himself he’d find a job immediately, anything to get out of this mess.

One week in though, and he was no closer to finding a job. The hair on his legs, arms, and chest was gone—shaved away under Caroline’s orders. By the second week, she had him wearing a corset—black with pink trim—and made him lace it up himself in front of the mirror each morning.

The eyebrows were shaped. The nails, manicured in a soft blush pink, then acrylic’d into long, feminine claws. His ears pierced. Lips glossed. Foundation and contour soon became daily routines under her strict supervision. He fumbled at first—but now, a month later, he could do a passable smoky eye in fifteen minutes flat.

Caroline also insisted on voice lessons. Every evening, she would sit him down and make him repeat carefully chosen phrases, over and over, until his pitch was soft, breathy, and obedient. “Yes, Mistress,” “I’m sorry, Mistress,” “Thank you, Mistress”—each one delivered in a tone that made his skin crawl.

Months later, Bella stood in the kitchen, perched precariously in six-inch stiletto platforms, fishnet thigh-highs biting into her freshly shaved thighs, a flouncy black and white French maid dress just barely covering her cage. The frilly apron was spotless, tight satin fabric hugging every feminized curve Caroline had teased out of her little sissy. Her hair was curled, held back with a lacy headband, and her lips were a perfect pouty rose pink.

She dusted the counter, her fishnet-covered ass swaying in hypnotic rhythm. She didn’t dare stop. Not after last week—when Caroline had caught her slacking and “corrected” her. Bella’s cheeks flushed as she moved, the pressure of the butt plug inside her a constant, humiliating reminder with every subtle shift of her hips.

Caroline strolled in, heels clicking on the tile, and gave Bella’s smooth ass a sharp smack, smirking as she purred, “Still unemployed, huh?”

Bella let out a soft, involuntary moan as the butt plug shifted from the sharp smack, brushing a sensitive spot deep inside her. Her cheeks flushed bright red, her body frozen as the humiliation pulsed through her. She couldn’t even think about applying for a job anymore—not when all her boy clothes were gone, replaced with corsets, skirts, panties, and heels. Her voice cracked in shame whenever she tried to speak with authority, always too soft, too breathy, too trained.

“N-no, Mistress… not yet…” she whimpered.

Caroline stepped behind her, letting her hands glide slowly down the curve of Bella’s corseted waist, her nails lightly grazing the satin as she leaned in.

“Who would’ve thought my ex would make such a cute, obedient little thing,” she purred, voice thick with amusement. “Don’t worry, sissy. You can stay with me as long as you need”