Page 4

The afternoon sun cast a warm glow across the campus as Olivia made her way to Jessica's apartment. She'd donated every single article of clothing she'd owned, sending pictures to Jessica to prove it. The thrift store had been glad to accept them, asking if everything was okay.

"Lifestyle change," is all Olivia had offered by way of explanation.

Her heart pounded in her chest, a mix of anticipation and anxiety swirling within her.

The weight of the breast forms and the tightness of the feminine underwear were constant reminders of just the first morning.

Every step she took in the sensible dress Jessica had insisted she keep on felt like another step away from her old life and deeper into this new one.

Into submission. And this was just the first day. How long could she handle it?

Jessica greeted her at the door, her expression unreadable but her eyes gleaming with a hint of mischief.

"Come in, Olivia," she said, stepping aside to let her in.

The apartment was immaculate, a stark contrast to the chaos of Olivia's dorm room. Jessica led her through the living room and into the bathroom, where a vanity mirror was already set up with an array of makeup products neatly arranged on the counter.

"Sit down," Jessica instructed, pointing to the stool in front of the mirror.

Olivia obeyed, her eyes widening at the sight of the various powders, brushes, and tubes.

Jessica stood behind her, their reflections framed in the mirror.

"Today, I'm going to teach you how to do your makeup. I expect my pet to look perfect, every day."

Olivia nodded, her hands trembling slightly as she picked up a foundation brush.

Jessica guided her through each step, demonstrating the proper techniques for applying foundation, blending eyeshadow, and lining her lips.

Olivia's concentration was intense, but her inexperience showed. She fumbled with the eyeliner, the line coming out uneven and smudged.

Jessica's eyes narrowed, and she let out a frustrated sigh. "Poorly done," she said, her voice cold. "Precision is the only thing that separates an artist from a preschooler." She grabbed Olivia's wrist, her grip firm but not painful.

"For every mistake, there will be a punishment. Am I understood?"

Olivia swallowed hard and nodded. "Yes, Jessica," she replied, her voice barely above a whisper.

Jessica's expression softened slightly, but her eyes remained stern. "Good. Now, fix it."

Olivia tried again, her hands shaking as she attempted to correct the mistake. But the pressure was too much, and the line came out even worse. Jessica clicked her tongue, a sound that sent a chill down Olivia's spine.

"That's two mistakes, Olivia," she said, her voice laced with disappointment. "Stand up."

Olivia obeyed, her legs trembling as she rose to her feet. Jessica reached into a drawer and pulled out a small paddle. "Hold out your hands," she ordered.

Olivia hesitated, but the stern look in Jessica's eyes left no room for argument. She held out her hands, palms up, and Jessica brought the paddle down with a sharp smack. The sting was immediate and intense, tears springing to Olivia's eyes.

Jessica repeated the action, the second strike just as painful as the first.

"Try again," Jessica commanded, her voice so terrifyingly calm.

Olivia's hands trembled slightly as she picked up the eyeliner once more, the sting from the paddle still fresh on her palms. Jessica's presence loomed behind her, a constant reminder of the expectations she had to meet.

She took a deep breath, steadying herself, and carefully drew the line along her eyelid.

This time, it was better—still not perfect, but an improvement.

Jessica nodded approvingly. "Good. You're getting there. Now, try the other eye."

Olivia's confidence grew as she managed to replicate the line on her other eyelid with fewer mistakes. But as she moved on to the next step—blending eyeshadow—her nerves returned. Her inexperience showed as she struggled, smudging it in uneven clumps. Jessica's eyes narrowed, and Olivia knew what was coming before the words left her lips.

"Stand up."

Jessica reached for a thin, flexible cane this time, a tool that looked far more menacing than the paddle.

Olivia's heart raced as she stood, her body tensing in anticipation. Jessica motioned for her to turn around and lean over the vanity. With a swift, practiced motion, Jessica brought the cane down on Olivia's backside, the sharp sting eliciting a gasp.

It landed with a sharp crack, the sting spreading across Olivia's bare bottom in a wave of pain and pleasure. She bit her lip, a moan escaping despite her best efforts to stay silent. Each strike was precise, Jessica's control absolute as she administered the punishment.

Olivia's skin burned, but with each stroke, the heat turned to a throbbing ache that only heightened the sensation. She delivered three more strikes, each one more precise and painful than the last.

"Back to work," Jessica ordered, her voice cold. Olivia returned to her seat, her cheeks flushed and eyes glistening with unshed tears. The pain was intense, but it only fueled her determination to get it right.

With Jessica's stern guidance, Olivia's technique slowly improved.

The eyeshadow blended more smoothly, the mascara didn't so obviously clump, and the eyeliner was more precise, more even every attempt. Each small victory was met with a nod of approval from Jessica, but the mistakes—though fewer—continued to be met with punishment. As Olivia moved on to applying lipstick, her hand slipped, smudging the color outside her lip line.

Jessica sighed, shaking her head. "Stand up."

This time, Jessica produced a thin leather strap.

Olivia's eyes widened in fear as she braced herself. Jessica delivered a series of sharp, stinging blows to the backs of her thighs, the pain searing through her. She gasped at each one, body shaking in the waves of pain. Olivia's resolve was being tested to its limits, but she knew she had no choice but to endure.

"Sit back down and fix it," Jessica commanded, her voice devoid of sympathy. Olivia obeyed, her body aching from the cumulative punishments. She carefully reapplied the lipstick, trying desperately to keep her hands steady despite the lingering pain.

Under Jessica's relentless tutelage, Olivia's skills gradually honed. The harsh punishments served as a brutal motivator, driving her to focus and improve each technique. By the end of the session, Olivia's makeup looked okay, but not perfect by any standards.

Jessica stood back, finally satisfied. "You're learning, pet. But just decent isn't good enough. You will be better tomorrow, or you will be punished. You will be perfect, soon, or you will be punished. Am I understood?"

Olivia nodded, her voice trembling as she replied, "Yes, Jessica."

Jessica's eyes narrowed as she picked up on the subtle mistake Olivia made. "What did you just call me?" she asked, her tone icy.

Olivia's heart sank, realizing her slip-up. "I... I'm sorry, Mistress," she stammered, her voice barely a whisper.

Jessica shook her head, her expression one of stern disapproval. "Clearly, this isn't working, sissy." She practically spat the last word.

She grabbed Olivia by the wrist and led her out of the bathroom, down the hallway, and into her bedroom.

The room was immaculate, with a large bed in the center and a neatly organized desk against one wall.

Jessica reached into a drawer and pulled out a leather-bound journal and a pen, placing them on the desk.

"Sit down," she ordered, pointing to the chair. Olivia obeyed, her heart racing as she sat at the desk. Jessica opened the journal to a blank page and handed her the pen. "You will write the following sentence: 'I am hers, I am a sissy, and I will not disappoint my Mistress.'"

Olivia's eyes widened at the task, but she nodded, picking up the pen with trembling hands. She began to write, the sentence flowing from her pen in neat, precise letters. Jessica watched her for a moment, then turned to leave the room.

"I'll be back to check on you later. You know what happens if you stop."

As the door closed behind her, Olivia's heart pounded in her chest. She focused on the task, the repetitive motion of writing the sentence over and over becoming a mantra. "I am hers, I am a sissy, and I will not disappoint my Mistress." Each line etched deeper and deeper into her mind.

Minutes turned into an hour, and still, Olivia wrote. Her hand began to cramp, the muscles burning from the constant motion. She wanted to glance at the clock, but the threat of Jessica returning the moment she looked up weighed on her. Better to not risk it, to keep writing, to keep going.

Sweat beaded on her forehead as she continued, the sentence becoming innate as her hand moved automatically.

Hers. Sissy. Mistress.

Olivia's hand felt like it was on fire. Her writing grew sloppier, the letters smudged and uneven. She fought through the pain, her mind focused on pleasing Jessica, on proving her obedience. The words on the page became a lifeline, a way to cling to something amidst the pain and exhaustion.

Finally, the door creaked open, and Jessica stepped back into the room. She glanced at the journal, her eyes scanning the pages filled with Olivia's handwriting. A satisfied smile tugged at the corners of her lips as she took in the sheer volume of sentences.

"Good girl," she said, her voice softening just a touch. Emotions rushed through her. pleasure. Joy. Peace. Acceptance.

"You've done well, Olivia."

Olivia looked up, her eyes filled with a mixture of relief and exhaustion. "Thank you, Mistress," she whispered, her voice trembling with a mix of pain and determination.

Jessica nodded, closing the journal and placing it back in the drawer. "You may rest now, but remember that this is what happens when you disobey. Not terrible for your first day, pet."

Olivia nodded, her body aching but her resolve stronger. She understood the stakes, the consequences of her actions. And she was determined to prove herself worthy of Jessica's control, no matter the cost. There was no other option.