Sissy's New Life

Chapter Twenty: Holiday of Humiliation

The end of the university year brought a brief respite for most students, but for Mitch, it meant another round of relentless torment. Lanya decided they should take a cheap holiday, renting a caravan in a secluded spot in the woods. Mitch initially felt a glimmer of hope, imagining some peace and quiet away from the daily humiliations. Little did he know, Lanya and Abbie had a sinister plan in mind.

On the day of departure, Lanya and Abbie dressed Mitch meticulously. He was put in a beautiful, flowing summer dress that clung to his figure, accentuating every curve. Locked heels ensured he could barely walk without teetering, adding to his discomfort. His false nails were super glued on, long and painted a bright red. His makeup was done to perfection for once—tidy and elegant, highlighting his feminine features.

When they arrived at the campsite, Mitch noticed the peaceful surroundings and felt a brief sense of relief. However, this tranquility was short-lived. Unbeknownst to Mitch, Lanya had placed an ad on a fetish website, inviting local mistresses to join their escapade. One response stood out—from a woman named Dolly, whose kinks were extreme and varied.

Dolly arrived that evening, a tall, imposing figure with a confident stride. She wore a tight black leather outfit that left little to the imagination, her eyes glinting with anticipation. Lanya and Abbie welcomed her warmly, exchanging knowing glances as they introduced her to Mitch.

"Hello, sissy," Dolly said, her voice dripping with condescension. "I've heard so much about you."

Mitch's heart sank as he realized what was coming. Dolly wasted no time, taking control immediately. She led Mitch into the caravan, where various implements of torment awaited. She started by binding his wrists and ankles with thick leather straps, ensuring he couldn't move. Then she applied clamps to his nipples, the sharp pain making him gasp.

"Let's see how much you can take," Dolly whispered, her breath hot against his ear.

She produced a large dildo, strapping it on before approaching Mitch menacingly. The next few hours were a blur of intense, degrading acts. Dolly used him mercilessly, each thrust sending waves of pain and humiliation through his body. She alternated between spanking him with a paddle and forcing him to gag on the dildo, her laughter echoing in the confined space.

As Dolly continued her torment, Abbie was secretly broadcasting everything live on Mitch's personal Facebook account. His friends, family, and university acquaintances watched in shock and disbelief as Mitch was subjected to unspeakable acts. Comments poured in, each one a stab to his already broken spirit.

"Oh my God, is that really Mitch?"

"What a freak! How can anyone do this?"

"This is disgusting. Someone needs to stop this!"

The video gained traction quickly, spreading like wildfire across social media. Mitch's phone buzzed incessantly with notifications, each one a reminder of his exposed degradation.

Meanwhile, back in the caravan, Dolly decided to up the ante. She produced a set of butt plugs, each one larger than the last. Mitch whimpered as she inserted them one by one, the increasing size stretching him painfully. She then attached a leash to his collar, pulling him to his knees.

"Now, crawl for me," Dolly commanded, dragging him outside into the dirt.

Mitch complied, his knees scraping against the rough ground as Dolly paraded him around the campsite. Lanya and Abbie watched with glee, capturing every humiliating moment on camera.

As night fell, Dolly's cruelty showed no signs of waning. She tied Mitch to a tree, his arms and legs spread wide. She then brought out a riding crop, striking him repeatedly across his thighs and buttocks. The stinging pain made Mitch cry out, but his pleas for mercy were ignored.