Sissy's New Life

Chapter Eighteen: Night of Torment

Mitch's days had descended into an unending nightmare. Each morning began with grueling tasks designed to break his spirit. Today, he was made to wake up at dawn, his wrists and ankles still sore from the chains that bound him overnight. His mistresses were relentless, ensuring he started his day with a cold shower, the icy water shocking his system and leaving him shivering.

After his shower, Mitch was led to the kitchen, where a humiliating breakfast awaited—eating from a dog bowl on the floor while the mistresses laughed and mocked him. His attire for the day was even more degrading: a ridiculous French maid outfit with frills and lace that left little to the imagination. The dress was so short it barely covered his backside, and the matching apron emphasized his subservient role.

His face was painted with garish makeup—thick eyeliner that made his eyes look exaggerated, bright red lipstick smeared across his lips, and rouge that gave his cheeks a clownish appearance. They added a large pink ribbon to his hair, making him look like a twisted version of a child's doll.

On campus, Mitch was the target of relentless bullying. Videos of his humiliations spread across the university like wildfire, making him a laughingstock. His phone buzzed constantly with notifications—cruel messages from classmates and strangers alike.

"Hey Sissy, loved the new video. You're such a whore!"

"Do you enjoy being everyone's plaything, slut?"

"You deserve everything that's happening to you, freak."

The barrage of abuse was overwhelming. Mitch tried to keep his head down, but the whispers and laughter followed him everywhere. He could feel eyes on him constantly, judging, mocking. Every glance, every snicker was a dagger to his already shattered self-esteem.

One particularly gruelling day, after being forced to endure another humiliating cheerleading practice, Mitch returned home to find his mistresses waiting. Lanya, Alexandra, Abbie, and Lauren stood with knowing smirks, their eyes gleaming with sadistic pleasure.

"We saw the video from today," Lanya said, her voice dripping with mock sympathy. "You cried on camera again."

Mitch's heart sank. He knew what was coming—punishment for showing weakness. He opened his mouth to protest, but Alexandra cut him off.

"Don't bother arguing, Sissy. Tonight, you'll learn your place."

They dragged Mitch to his room and forced him into a new outfit: a short skirt, sheer white tights, and a padded bra. His makeup was touched up, making his face even more garish and exaggerated. They locked him in stilettos and added a pink collar around his neck.

With a cruel grin, Abbie held up a set of chains. "Time for your punishment."

Mitch was led out of the house and down the street, the night air cold against his exposed skin. They reached the park, which was eerily quiet at this hour. The mistresses found a bench and began securing Mitch to it. Chains wrapped around his wrists and ankles, binding him to the cold metal. They ensured he was immobile, his arms stretched out and his legs spread.

"You'll spend the night here," Lauren said, tightening the final chain. "Let's see if a night of public exposure helps you learn not to cry."

Tears welled up in Mitch's eyes, but he fought them back, knowing that showing weakness would only make things worse. The mistresses stepped back to admire their work, their laughter echoing in the empty park.

"Goodnight, Sissy," Lanya said, patting his cheek mockingly. "Enjoy your stay."

They left him there, alone and chained to the bench. The cold seeped through his thin clothing, and he shivered uncontrollably. He could hear distant sounds of laughter and cars passing by, but he was utterly alone in his torment.

As the hours passed, Mitch's discomfort grew. The chains chafed against his skin, and the cold made his muscles ache. He tried to shift position, but the bindings were too tight. All he could do was sit there, exposed and vulnerable, his humiliation complete.

Throughout the night, a few passers-by noticed him. Some laughed, others took photos or videos, further adding to his humiliation. A couple of them even approached to taunt him, their words cutting deep.

"Look at the little sissy, all tied up and pretty."

"Did your mistresses do this to you? You must love it."

By the time morning arrived, Mitch was exhausted, cold, and utterly broken. His mistresses returned, unchaining him with satisfied smiles.

"Learned your lesson?" Alexandra asked, her eyes gleaming with sadistic pleasure.

Mitch nodded weakly, too defeated to respond. They led him back home, where he was forced into his cage for a few hours of restless sleep.

The cycle of torment and humiliation would continue, but Mitch knew there was no escape. His life had become a never-ending nightmare, and he was powerless to change it.