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The Making of a Sissy Submissive

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Jim strikes it rich and retires, seeking to fulfill his submissive fantasies as a humiliated, chaste sissy. He enlists the help of a sleazy lawyer and his ex-gf, who broke up with him when she found out, calling him a faggot. The lawyer reaches out to a porn studio, asking to set up a blowbang for sissy Jim, but they make up a restrictive contract to humble Jim and ensure he has the appropriate experience sucking dick before letting him be in a blowbang. Jim is humiliated at every step of the way, being fully feminized and put in chastity, as he tries to meet his goal of sucking 100 cocks in a month. He is publicly exposed and humiliated, as he meets new men and some men from his past that used to bully him. Jim is in over his head but his submissive nature and sissy desires consume him as he goes along with it all in an attempt to fulfill his dream.

Chapter 2: Building Tension

In the dim light of his apartment, Jim sat on the edge of his bed, his eyes flicking nervously between the locked cage hanging from the ceiling and the clock on the wall. The hours seemed to stretch out before him, each tick of the clock echoing like a countdown to his inevitable fate. His stomach churned with a mix of anxiety and anticipation, the remnants of last night's dinner churning uneasily in his gut.

The lawyer, Mitch, had left after depositing a fresh set of lingerie and a pair of heels at Jim's feet, his lips twisted into a sneer.

"Make sure you're dressed appropriately for your performance tonight, sissy," he'd said, before slamming the door shut behind him.

Jim had watched the door close, his heart pounding in his chest. He knew what was coming, had been preparing for it in his own way, but the reality of it was still daunting. He was to be the center of attention, the star of a show he hadn't chosen but had paid dearly for.

He turned his attention to the lingerie Mitch had left behind.

It was a lacy, baby blue number, with a matching thong and garter belt. The bra was barely more than a scrap of fabric, designed to lift and enhance rather than provide any real support. Jim picked it up, running the delicate material through his fingers. It was soft, almost silky, and he could imagine how it would feel against his skin.

But he hesitated, looking down at his body. He was lean, almost scrawny, with a smattering of chest hair and a trail leading down to his navel.

His arms were toned from years of swimming, but his shoulders were narrow, lacking the broadness of a true athlete. He had always been self-conscious about his body, comparing it unfavorably to the muscular specimens he saw in magazines or on TV. But now, as he looked at his reflection, he saw something different. He saw a body that was not meant for strength or power, but for submission and pleasure.

He reached up, tracing the line of his collarbone, his fingers brushing against the thin gold chain that hung around his neck.

It was a simple piece of jewelry, a gift from his mother years ago, but now it was a symbol of his submission. A constant reminder of the path he had chosen.

He took a deep breath, steeling himself for what was to come. He stood up, dropping the lingerie onto the bed. He would wear it, he knew he had to, but not yet. Not until he was ready.

He turned his attention to the cage hanging from the ceiling. It was small, barely big enough for him to stand in, let alone move around. The door was locked, the key nowhere to be found.

He knew Mitch had taken it, another way to assert his control, to remind Jim of his place. But Jim wasn't going to let that stop him. He was determined to face whatever was coming next on his own terms.

He grabbed a dining chair, dragging it over to the cage. He stood on it, reaching up to grasp the bars. They were cold and unyielding, like the fate that awaited him. He hoisted himself up, his muscles straining, until he was able to swing one leg over the top of the cage. He paused, balancing precariously, before dropping down into the confined space.

The cage swayed slightly, the chains creaking as they held his weight. He landed on his knees, the hard metal floor biting into his skin. He ignored the discomfort, focusing instead on the task at hand.

The cage was just tall enough for him to sit upright, but not much more. He had to hunch his shoulders, his knees bent awkwardly to fit. It was claustrophobic, the bars pressing in on him from all sides, but he felt a strange sense of security in the confinement. It was a safe space, a place where he could prepare for what was to come.

He took a deep breath, the air filled with the scent of old metal and the faint hint of his own sweat. He closed his eyes, letting the darkness envelop him, and focused on his breathing.

In. Out. In. Out.

With each breath, he felt his anxiety begin to ebb, his body relaxing into the cage. He was safe here, for now. He could take his time, prepare himself mentally and physically for what was to come.

He reached up, his fingers tracing the cold metal bars, feeling the ridges and imperfections.

He focused on the sensation, grounding himself in the present, away from the swirling thoughts of fear and anticipation. He was here, now, in this cage, and that was all that mattered.

After what felt like hours, he heard the key turn in the lock. The door creaked open, and light flooded in, momentarily blinding him. He squinted, his eyes adjusting to the sudden brightness.

Mitch stood in the doorway, his silhouette framed by the harsh light behind him. "About time you woke up, sissy," he drawled, his voice dripping with disdain.

"We've got a busy night ahead of us."

Jim blinked, his eyes finally adjusting to the light. He could see Mitch clearly now, his greasy hair slicked back, his eyes cold and calculating. He was holding a set of keys, jingling them tauntingly in his hand.

Mitch reached into the cage, grabbing Jim roughly by the arm and hauling him out. Jim stumbled, his legs wobbly from hours of confinement, but Mitch didn't give him a chance to regain his balance. He shoved him towards the bed, where the lingerie Jim had been admiring earlier lay waiting.

"Get dressed, sissy," Mitch barked, his voice harsh. "We don't have all day."

Jim hesitated, looking down at the delicate garments. He had been so sure earlier, so determined to face this on his own terms. But now, with Mitch looming over him, his eyes cold and unyielding, Jim felt a flicker of doubt.

Mitch noticed his hesitation and sneered. "What's the matter, sissy? Not up for your big debut?"

Jim gritted his teeth, pushing down the doubt. He wouldn't give Mitch the satisfaction of seeing him falter.

He picked up the bra, his fingers trembling slightly as he reached behind his back to fasten it. The material was soft, but the underwire was firm, pushing his breasts up and together. He felt a rush of self-consciousness, looking down at his chest. Without the padding of a real bra, his nipples were clearly visible, pressing against the thin lace.

Next, he slipped on the thong, the fabric barely covering his ass. He could feel the cool air against his skin, making him acutely aware of his nakedness.

He reached for the garter belt, his fingers fumbling slightly as he tried to clip it onto the stockings. Mitch watched him, his arms crossed over his chest, a smirk playing on his lips.

"Need some help, sissy?" he taunted, his voice laced with mock concern.

Jim ignored him, finally managing to clip the garter belt into place. He stood up, his legs wobbling slightly in the heels. He had never been particularly good at walking in them, but he was determined to do this right.

Mitch whistled, his eyes roving over Jim's body.

"Well, don't you clean up nice," he sneered. "Too bad you're just a sissy, and not a real woman."

Jim felt a flush of embarrassment, but he refused to let Mitch see him falter. He stood tall, his chin held high, despite the ache in his back from the uncomfortable position he was in.

Mitch grabbed a nearby makeup case, flipping it open to reveal an array of colorful powders and creams. "Alright, sissy," he said, his voice dripping with disdain.

"Let's make you look the part."

Mitch grabbed a foundation brush, dipping it into a pot of creamy beige makeup. He leaned in close, his breath hot on Jim's face as he began to apply the makeup. Jim tried to keep still, but he couldn't help but flinch at the rough texture of the brush against his skin.

"Hold still, you little worm," Mitch said, his voice harsh. "I'm not here to make you pretty, just presentable."

Jim bit back a retort, focusing instead on the sensation of the makeup being applied to his face.

The foundation was thick and heavy, clinging to his skin like a mask. Mitch worked quickly, his movements rough and efficient, as if he had done this a thousand times before. Which, Jim guessed, he probably had.

Next came the concealer, a peachy cream that Mitch dabbed under Jim's eyes and on the bridge of his nose. The powder followed, a fine mist that Mitch dusted over Jim's face with a large, fluffy brush. Jim couldn't help but think of his sister, back home, applying her makeup with careful precision. This was nothing like that.

Mitch was not gentle, not caring. He was rough, bordering on cruel, his movements jerky and impatient. Jim could feel the tension in the lawyer's hands, the way they trembled slightly as they worked. It was as if Mitch was angry, resentful even, at having to do this. As if Jim's very existence was an offense to him.

The blush came next, a bright pink that Mitch swept across Jim's cheeks with a wide, stiff brush. It felt harsh, too harsh, like sandpaper against his skin. Jim winced, but Mitch just sneered.

"Don't be such a baby, sissy. This is just the beginning."

The eyeshadow was next, a shimmering gold that Mitch swept across Jim's lids with a heavy hand. It felt strange, alien, to have makeup on his face. He had never worn it before, not even as a teenager experimenting with his identity. This was new, and it felt...wrong. But he pushed down the discomfort, focusing instead on the coolness of the metal bar pressed against his back, grounding him in the present.

The mascara was the worst.

Mitch grabbed Jim's chin roughly, tilting his head back, and began to smear the black ink onto his lashes. Jim felt a surge of panic, his eyes watering instinctively at the sudden contact. He tried to blink, to look away, but Mitch's grip was too tight.

"Hold still, damn it," Mitch growled, his breath hot and sour in Jim's face. "I don't want to poke your eye out."

Jim forced himself to relax, to trust in Mitch's steady hand. It was difficult, with the lawyer's eyes burning into him, filled with a mix of resentment and triumph.

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