Crossdressing Stories - Forced Feminisation on a LiveStream

Published on Jan 7, 2024 by Tohka Crow

Henry stood frozen outside Melanie's room, his phone clutched in his trembling hands. The gentle glow from the hallway light cast a stark contrast to the storm of emotions churning within him. A university student by day, today he found himself in a dilemma that threatened to overturn the calm demeanor he was known for.

The events of the previous night played over in his mind. The underground club, led by the charismatic Josh, had always seemed like an unreachable bastion of the university's elite. When Josh had casually extended an invitation to Henry, it felt like a dream. But the dream had quickly soured when Josh revealed the initiation task.

"You want to be one of us, right?" Josh's voice echoed in Henry's head, a blend of taunt and temptation. "Bring me something personal, something thrilling. How about your sister's panties?"

Henry had recoiled at the suggestion, planning to outsmart them with a store-bought pair. But Josh was one step ahead. "No cheating, Henry. We want a livestream. It's all about the adrenaline, the risk. That's what we live for."

Now, standing outside his sister's room, Henry's heart pounded furiously. Melanie, his sister, was out, blissfully unaware of the betrayal looming just beyond her bedroom door.

His phone, now a gateway to a potentially irreversible decision, felt heavy in his hand. He unlocked it, the screen lighting up with a notification from the club's chat group.

"Are you in or out, Henry?" the latest message from Josh read, its casual tone belying the weight of its implication.

Henry's finger hovered over the 'Live' button, the reality of his situation setting in. This wasn't just about gaining acceptance; it was about who he was and what he stood for. With a deep, shaky breath, he felt the gravity of the choice he was about to make, a choice that would define his character and the future of his relationship with his sister.

As Henry hesitated outside Melanie's room, the silence of the empty house echoed around him. He knew it was a rare opportunity; Melanie was out with her friends, a fact that made his task seem deceptively simple. Steeling his resolve, he pushed the door open and stepped inside.

Melanie's room was a cozy contrast to the tension gripping Henry. Soft, diffused light filtered through the curtains, illuminating the well-kept space. He approached her dresser, his movements robotic, as he activated the livestream on his phone. The chat from the club members began to populate the screen, each message spurring him further into an act he knew was wrong.

"Which one, guys?" Henry whispered into the phone, his voice barely concealing his anxiety. He opened a drawer, revealing an assortment of neatly folded garments. The livestream chat buzzed with suggestions, each one pushing him further into the abyss of betrayal.

Suddenly, the sound of the front door opening jolted him back to reality. Footsteps approached, and before he could react, Melanie burst into the room, her two friends in tow. "Henry, what the hell are you doing in my room?!" she yelled, her voice a mixture of shock and anger.

Henry, startled and mortified, dropped his phone in panic. It landed with a thud at Melanie's feet, the livestream still running. She picked it up, her eyes widening as she realized what was happening. "I was out with the girls," she said, her voice trembling with fury and disbelief, "but then I got this message from someone named Josh. He said if I came home now, I'd catch a thief red-handed."

The room was thick with tension, the gravity of Henry's betrayal hanging heavily in the air. His plan, his desire for acceptance, had not just failed spectacularly but had also exposed a side of him he wished never to confront. The realization of what he had almost done, and the consequences it now bore, began to sink in.

Melanie's anger was palpable, her face a mask of disbelief and fury. "What kind of person livestreams their sister's private clothing?" she demanded, her voice laced with indignation. She turned to her friends, seeking affirmation. "This needs some kind of punishment, don't you think?"

Henry stood rooted to the spot, his face flushed with shame. He stammered, trying to explain the twisted logic behind his actions. "It was a test, Melanie. To join a club. I didn't mean..."

His words were cut short by Melanie's harsh laugh. "A test? Oh, that's rich. Well, guess what, Henry? My friends and I have a test for you too. Welcome to the girls' club." Her tone was mocking, her gaze sharp as she picked up his phone and addressed the livestream. "What do you think, everyone? Should we give Henry a test of our own?"

The chat erupted with laughter and encouragement, the viewers clearly entertained by the sudden turn of events. Melanie's friends, previously shocked, now wore smirks of amusement, their earlier sympathy for Henry vanishing in the face of this unexpected drama.

Henry, felt a sinking feeling in his stomach. The tables had turned dramatically, and now he was at the mercy of his sister and her friends, with an audience of peers watching eagerly. The shame of his actions weighed heavily on him, a stark reminder of the consequences of seeking approval in the wrong places.

Henry stood, his face burning with humiliation, in the center of Melanie's bedroom. The situation had spiraled beyond his worst nightmares. Melanie, her anger morphing into a mischievous form of retribution, issued her command with a stern tone. "If you like women's panties so much, Henry, why don't you try wearing one? Pick a pair, or you're really going to be in trouble."

The viewers on the livestream, eagerly watching the drama unfold, egged on the unfolding scene. Henry, his mind a whirlwind of embarrassment and regret, reluctantly reached for a pair of pink panties. His movements were mechanical, driven by a desire to just get it over with. He quickly stripped off his clothes and slipped into the panties, his face a deep shade of red.

Melanie, seizing the moment, placed the phone on a chest of drawers, ensuring the livestream captured every moment. The room erupted in laughter as Henry stood there, clad only in the pink underwear, the absurdity of the situation not lost on anyone. Melanie's friends, initially shocked, now reveled in the bizarre turn of events, their laughter echoing off the walls.

Then, adding to Henry's mortification, Melanie brought a chair and placed it in front of her full-length mirror. "It's makeover time," she declared, a playful yet devilish glint in her eye. The implication was clear: the humiliation was far from over. Henry, standing in the middle of the room, could only wonder how far his sister would go in her quest for retribution, the viewers on the livestream eagerly awaiting the next act of this unexpected drama.

Henry sat on the chair, a deep sense of humiliation washing over him as Melanie and her friends transformed him. The playful atmosphere in the room was thick with mockery and laughter, each action by the girls amplifying his embarrassment.

One of Melanie's friends produced a matching bra for the pink panties he was wearing. With exaggerated care, she helped him put it on, their laughter echoing in his ears. Henry could feel his cheeks burning, the reality of his situation sinking in with every passing second.

Melanie, taking charge of the makeover, began applying makeup with an artist's precision. She started with foundation, smoothing it over his face, followed by concealer and contouring to accentuate his features. Eyeshadow came next, with Melanie choosing bold colors that stood out starkly against his skin. The foxy eyeliner was applied with a flourish, followed by false eyelashes that fluttered dramatically every time he blinked. His lips were next; Melanie overdrew them before applying a bright red lipstick and a layer of glossy lip gloss.

Throughout the process, the girls' laughter and teasing were unrelenting. They reveled in the absurdity of the situation, their actions fueled by the encouragement and amusement of the livestream audience.

Then came the final touch of their game. Melanie turned to the livestream chat. "What should we call our new sister?" she asked, her voice dripping with mock sincerity. The chat responded with enthusiasm, throwing out suggestions until a poll was held. The result? Henry's new name was now Helena.

The room erupted in laughter as they began referring to him by his new name. "Helena, you look fabulous," Melanie teased, her words sharp with mockery. Henry, now Helena, sat there, a living embodiment of his own misguided actions, the laughter and humiliation a stark reminder of the consequences of seeking acceptance without considering the cost.

As the transformation of Henry into 'Helena' continued, the laughter and chatter in Melanie's room only grew louder. The girls, fueled by the encouragement of the livestream audience, brought out the final pieces to complete the look. Each item seemed to add another layer to Henry's growing sense of humiliation, yet there was an inexplicable feeling stirring within him, a perplexing mix of emotions he couldn't quite identify.

"Here, Helena, let's get these on you," one of Melanie's friends said as she handed him a pair of black pantyhose. Henry, or Helena as he was now being called, could feel his face flush even deeper as he slipped into them.

Next came the jeans miniskirt, followed by a pink crop top t-shirt that matched the panties and bra. The outfit was a far cry from anything Henry had ever worn, each piece accentuating the absurdity of his situation. When one of the girls brought out pink high platform shoes and a blonde wig, the transformation seemed complete. He hesitated for a moment, the reality of his situation hitting him hard.

"You're doing great, Helena," Melanie said, her voice dripping with sarcasm. "Who knew you had it in you to be such a cute girl?"

The girls helped him into the shoes, steadying him as he struggled to balance. The wig was placed on his head, the blonde locks cascading down around his shoulders. As they finished, the girls guided Henry, now fully Helena, to the mirror.

Standing before his own reflection, Henry was taken aback. The person staring back at him was unrecognizable - a cute girl with perfect makeup, stylish clothes, and an air of femininity. It was a stark contrast to his usual self, a transformation so complete that for a moment, he felt disoriented.

Melanie and her friends leaned in, whispering more humiliating comments. "Look at you, Helena, aren't you just adorable?" one said. "Bet you never knew how good you'd look in a skirt," another added.

The livestream chat continued to buzz with laughter and teasing remarks. But amidst the humiliation and the sting of his sister's mockery, Henry felt something unexpected stirring within him. Part of him was mortified, wanting nothing more than to escape this situation, yet another part was strangely intrigued by his reflection, by the feeling of the clothes, the weight of the wig. It was a confusing mix of emotions, one that left him feeling vulnerable yet curiously liberated.

As he stood there, surrounded by laughter and the persistent chatter of the livestream, Henry couldn't help but wonder about the complexity of his own identity, about the hidden facets of himself that this bizarre ordeal had unwittingly revealed.

Melanie's friend leaned closer to 'Helena', her voice laced with teasing malice. "Who would have thought, Henry, that you'd make such a pretty girl? Maybe you've missed your calling," she said, her words sharp with mockery. The other girls giggled, their eyes shining with a mix of amusement and disbelief at the transformation before them.

Helena, stood awkwardly in front of the mirror, her reflection a constant reminder of the surreal turn her life had taken in just a few hours. The mix of feelings inside her was overwhelming – humiliation, confusion, and a curious sense of intrigue.

Melanie, the ringleader of this unexpected event, turned back to the chat, her eyes gleaming with excitement. "Alright, everyone, it's still early," she said, addressing the livestream with a conspiratorial smile. "Any ideas on what we should do with Helena now? Let's hear your suggestions!"

The chat erupted with ideas, each more outlandish than the last. The viewers, fully invested in the spectacle, offered a myriad of suggestions, eager to see how far Melanie and her friends would take this game. As the ideas flowed in, Helena could feel a knot of apprehension forming in her stomach, wondering what her sister would choose next. The night had taken a turn she never could have imagined, and now, dressed as Helena, she was at the mercy of Melanie, her friends, and an unseen audience that was all too eager to see what would happen next.