Bullied Into Crossdressing

Joe’s heart pounded in his chest as he stood in the dimly lit room, the cold fear gripping him like a vice. The air was thick with tension, and the sound of his own breathing echoed in his ears. He glanced around the circle of grinning faces, each one leering at him with a mix of amusement and malice. Shaun, the ringleader, held up a bundle of fabric in one hand, a sly grin spreading across his face.

“Alright, Joe,” Shaun said, his voice dripping with anticipation. “Time to get you all dolled up.”

Joe’s stomach churned as he recognized the outfit: a skimpy schoolgirl uniform, complete with a short plaid skirt, white blouse, and knee-high socks. His mind flashed back to the last time they had pulled this stunt on a road trip, the humiliation and discomfort still fresh in his memory. But this time, it was different. This time, they were taking it to a whole new level.

“No,” Joe muttered, shaking his head. “I’m not doing this again.”

Shaun’s grin widened, and he stepped closer, his eyes gleaming with excitement. “Oh, but you are, Joe. You don’t have a choice.”

Before Joe could protest further, two of Shaun’s coworkers grabbed him by the arms, pinning him in place. He struggled against their grip, but it was no use. They were too strong, and he was too weak. Shaun moved in front of him, holding the uniform up for inspection.

“Let’s see,” Shaun mused, his eyes scanning the outfit. “First, the skirt.”

One of the men released Joe’s arm long enough to yank down his pants, leaving him standing in nothing but his boxers. Joe’s cheeks flushed with embarrassment as the cool air hit his skin, but there was nothing he could do to stop them. Shaun wasted no time in sliding the short plaid skirt over Joe’s hips, the material barely covering his ass.

“Perfect,” Shaun said, stepping back to admire his handiwork. “Now, the blouse.”

The second man reached for Joe’s shirt, unbuttoning it quickly and pulling it off his shoulders. Joe shivered as the fabric was stripped away, leaving him exposed. Shaun held the white blouse up to Joe’s chest, slipping it over his head and buttoning it up. The sleeves were too short, exposing his wrists, and the collar gaped open, revealing the hollow of his throat.

“Almost done,” Shaun said, his voice filled with satisfaction. “Just need the socks.”

One of the men knelt in front of Joe, pulling off his shoes and socks. Joe winced as the rough fabric of the knee-high socks rubbed against his skin, but there was no escape from the humiliation. Once the socks were in place, Shaun stepped back, clapping his hands together.

“There we go,” Shaun said, his grin never faltering. “All set.”

Joe looked down at himself, feeling a wave of disgust wash over him. The skirt was so short that it barely covered anything, and the blouse clung to his body in a way that made him feel even more vulnerable. The knee-high socks only added to the absurdity of the outfit, making him look like a parody of a schoolgirl.

“Now,” Shaun said, his voice dropping to a low, menacing tone. “It’s time for the final touch.”

He reached into his pocket and pulled out a pair of black pigtails, attaching them to Joe’s hair with quick, practiced movements. Joe felt a surge of anger as the fake hair bounced against his scalp, but he knew better than to resist. These men had gone too far, and there was no turning back now.

“Look at you,” Shaun said, circling Joe like a predator. “Such a pretty little schoolgirl.”

Joe clenched his fists, his body trembling with a mixture of rage and fear. He wanted to lash out, to fight back, but he knew it would only make things worse. Instead, he forced himself to stay still, to endure the humiliation.

“Alright, boys,” Shaun said, turning to his coworkers. “Let’s get this party started.”

The men chuckled darkly, their eyes gleaming with anticipation. Joe’s heart raced as he realized what was coming next. They had dressed him up like this for a reason, and he knew exactly what that reason was.

“Please,” Joe whispered, his voice barely audible. “Don’t do this.”

But Shaun was already moving, his hands reaching for Joe’s waist. Joe tried to pull away, but the other men held him in place, their grips unyielding. Shaun’s fingers found the hem of the skirt, lifting it slowly, exposing Joe’s bare ass to the cool air.

“Ready for your lesson, little girl?” Shaun asked, his voice dripping with mock concern.

Joe’s breath caught in his throat as Shaun’s hand came down hard on his ass, the sting of the slap sending a jolt of pain through his body. He bit back a cry, his eyes watering with the effort. But Shaun wasn’t done. He brought his hand down again, and again, each slap landing with brutal precision.

“That’s right,” Shaun said, his voice a low growl. “Take it like a good girl.”

Joe’s legs trembled beneath him, but he couldn’t move. The men had him trapped, their hands holding him in place as Shaun continued his assault. Each slap sent waves of pain radiating through his body, but it was the humiliation that hurt the most. He was being treated like a child, like a toy, and there was nothing he could do to stop it.

Finally, Shaun stopped, his hand resting on Joe’s burning ass. He leaned in close, his breath hot against Joe’s ear.

“Good girl,” Shaun whispered, his voice filled with satisfaction. “Now, let’s see how well you can take it.”

Joe’s heart skipped a beat as he realized what was coming next. Shaun’s hand moved lower, his fingers brushing against the waistband of Joe’s boxers. Joe tensed, his body trembling with anticipation. But there was no escape. Shaun’s fingers hooked into the fabric, pulling the boxers down with a single, swift motion.

Joe’s cock sprang free, hard and throbbing in the cool air. He closed his eyes, trying to block out the sight of his own arousal, but it was impossible. The humiliation was too intense, too overwhelming. He was completely exposed, completely at their mercy.

“Look at that,” Shaun said, his voice filled with amusement. “Our little schoolgirl is getting excited.”

Joe’s cheeks burned with shame, but he couldn’t deny the truth. His body was betraying him, responding to the abuse in ways he couldn’t control.

Shaun’s fingers deftly tied a black silk blindfold around Joe’s eyes, the fabric soft against his skin but the effect chilling. The world went dark, and with it, any semblance of control Joe thought he might have had vanished. He stood there, trembling, the cold fear gripping him tighter than ever before. The room was silent for a moment, the only sound the rapid beating of his heart.

“Hands on the table,” Shaun commanded, his voice low and authoritative. Joe hesitated for a fraction of a second, but the pressure of his coworkers’ hands on his shoulders forced him to comply. He placed his palms flat on the rough surface of the wooden table, feeling the grain dig into his skin. The position left him vulnerable, his ass sticking out provocatively beneath the short skirt.

“Good boy,” Shaun murmured, his tone dripping with satisfaction. “Now, let’s see how well you can serve.”

Joe felt a hand on his lower back, guiding him forward slightly. The touch was firm, unyielding, and he knew what was coming next. His breath hitched as he felt a warm, wet tongue lick along the crack of his ass, teasing the sensitive skin. The sensation was both humiliating and arousing, his body betraying him once again.

“Spread your legs,” Shaun ordered, his voice closer now, almost in Joe’s ear. Joe complied, his legs trembling as they parted. The cool air brushed against his exposed flesh, making him shiver. The tongue returned, this time delving deeper, exploring every inch of his asshole with deliberate slowness. Joe bit his lip to stifle a moan, the humiliation of the situation overwhelming him.

The tongue withdrew, and Joe felt a slick finger replace it, pressing against his tight hole. He tensed, but the finger was relentless, pushing past his resistance and entering him slowly. The sensation was intense, a mix of pain and pleasure that made his cock twitch. The finger moved inside him, probing, stretching, preparing him for what was to come.

“Such a good little schoolgirl,” Shaun whispered, his voice filled with dark amusement. “So eager to please.”

Joe’s cheeks burned with shame, but he couldn’t deny the truth. His body was responding to the abuse, his cock hard and throbbing in spite of himself. The finger withdrew, and Joe felt a momentary relief, but it was short-lived. Another finger joined the first, pushing deeper, stretching him further. He clenched his fists, trying to hold onto some semblance of control, but it was slipping away from him.

The fingers moved faster, working him open with increasing urgency. Joe’s breath came in ragged gasps, his body trembling with each thrust. The sensation was overwhelming, his mind reeling from the mix of pain and pleasure. He could feel his asshole loosening, becoming more pliant, ready for what was to come.

Finally, the fingers withdrew, and Joe felt a brief moment of panic. But it was quickly replaced by a new sensation, something hard and hot pressing against his entrance. He knew what it was without needing to see it, and his heart raced with a mix of fear and anticipation.

“Ready for your lesson?” Shaun asked, his voice a low growl. Joe didn’t respond, couldn’t respond, his throat too tight with anxiety. But his silence was all the answer Shaun needed.

With one swift motion, Shaun pushed inside him, filling him completely. Joe cried out, the pain sharp and intense, but there was no escape. Shaun held him in place, his hands gripping Joe’s hips tightly as he began to move, slow and deliberate. Each thrust sent waves of pain and pleasure through Joe’s body, his cock twitching with each movement.

“That’s it,” Shaun murmured, his voice soothing. “Take it like a good girl.”

Joe’s mind was a whirlwind of emotions, the humiliation and pain blending together until he could barely think straight. All he could focus on was the sensation of Shaun’s cock inside him, the way it stretched him, filled him, made him feel so utterly helpless. He could feel his own arousal building, his cock leaking pre-cum onto the table.

Shaun’s thrusts grew harder, faster, each one driving deeper into Joe’s ass. The pain was still there, but it was overshadowed by the growing pleasure, the way his body was responding to the abuse. Joe’s breath came in short, desperate gasps, his body trembling with each thrust.

“Look at you,” Shaun said, his voice filled with dark satisfaction. “Getting so excited, just like a good little schoolgirl.”

Joe’s cheeks burned with shame, but he couldn’t deny the truth. His body was betraying him, responding to the abuse in ways he couldn’t control. He could feel his orgasm building, the tension coiling tighter and tighter inside him.

“Please,” Joe whispered, his voice barely audible. “Please…”

But Shaun wasn’t done. He reached around, his hand closing around Joe’s throbbing cock, stroking it in time with his thrusts. The sensation was overwhelming, the pleasure too intense to resist. Joe’s body tensed, his breath catching in his throat as he felt the orgasm building, threatening to overwhelm him.

“Come for me,” Shaun commanded, his voice a low growl. “Show me how much you love being my little schoolgirl.”

Joe’s body trembled, his mind a haze of pleasure and pain. He could feel the orgasm building, the tension coiling tighter and tighter inside him. With a cry of mingled pleasure and humiliation, he came, his cock pulsing in Shaun’s hand as he spilled his seed onto the table.

Shaun continued to thrust, his movements relentless, driving Joe to the brink again and again. Each thrust sent waves of pleasure through his body, his cock twitching with each movement. The sensation was overwhelming, his mind reeling from the intensity of it all.

Finally, Shaun came, his thrusts growing erratic as he emptied himself inside Joe. Joe cried out, his body trembling with the force of it, the sensation of Shaun’s cum filling him almost too much to bear.

Shaun withdrew, leaving Joe standing there, trembling and spent. The room was silent for a moment, the only sound the rapid beating of Joe’s heart. He could feel the cum dripping down his legs, the humiliation complete.

“Good girl,” Shaun murmured, his voice filled with satisfaction. “Now, let’s see how well you can take the rest.”

Joe’s heart skipped a beat as he realized what was coming next. He could hear the other men moving, their footsteps approaching. The realization of what was about to happen hit him like a punch to the gut, and he felt a surge of panic.

“No,” Joe whispered, his voice trembling. “Please, no…”

But it was too late. The first man stepped forward, his hand closing around Joe’s throbbing cock. Joe gasped, the sensation of another hand on his body sending shivers down his spine. The man began to stroke him, his movements slow and deliberate, teasing the sensitive flesh.

“Such a pretty little schoolgirl,” the man murmured, his voice filled with dark amusement. “So eager to please.”

Joe’s cheeks burned with shame, but he couldn’t deny the truth. His body was responding to the abuse, his cock hard and throbbing in spite of himself. The man’s hand moved faster, the sensation overwhelming, his mind reeling from the intensity of it all.

“Please,” Joe whispered, his voice barely audible. “Please…”

But the man wasn’t done. He leaned in close, his breath hot against Joe’s ear.

“Beg for it,” the man commanded, his voice low and menacing. “Beg for me to make you come.”

Joe’s mind was a haze of pleasure and pain, the humiliation too much to bear. But he knew he had no choice. With a sob, he opened his mouth, his voice trembling as he spoke.

“Please,” Joe whispered, his voice breaking. “Please, make me come…”