Kai/Kylee : Sorority Sissy

Chapter 9: Makeover

The following day, a lively anticipation buzzed through the Alpha Phi house as preparations for the evening's party got underway. The sorority sisters bustled about, setting up decorations and arranging refreshments, the grand living room transforming into a chic, glamorous venue for the night's festivities. Amid the flurry of activity, Madison had something specific in mind for Kylee—a test designed to challenge her under the guise of preparation.

Madison found Kylee in one of the quieter rooms, her predatory smile reflecting her intentions. "Kylee, we're hosting a party tonight, and I want you to do your own makeup for it," she announced, her tone deceptively casual. "Let's see if you can manage to make yourself presentable without anyone's help. I'm sure you'll do your best," she added, her eyes glinting with a hint of mischief.

Kylee's heart skipped a beat at the challenge. She knew Madison was looking to expose any shortcomings, expecting Kylee to falter and embarrass herself. However, what Madison didn't know was that Kylee had been diligently practicing her makeup skills in secret. Countless hours spent watching tutorials online and experimenting with different techniques had honed her abilities. The thought of being able to please Madison filled Kylee with a mixture of excitement and determination.

With a steadying breath, Kylee sat at the vanity in Madison's room, her fingers brushing over the array of cosmetics laid out before her. The familiar tools of transformation—the foundation, brushes, eyeshadow palettes, and lipsticks—felt reassuring in her hands.

Madison watched Kylee take off her makeup, exposing her natural features.

Madison's eyes roved critically over Kylee's bare face, noting every contour and feature that betrayed her male origins. The morning light streaming through the window cast a stark clarity on Kylee's unadorned skin, making her feel exposed under Madison's scrutinizing gaze. "Interesting," Madison murmured, stepping closer and tilting Kylee's chin up slightly with her finger. "Without makeup, you're not fooling anyone. You look so much more like a guy, it's almost disappointing."

Kylee felt a flush of embarrassment and vulnerability, her cheeks warming under Madison's touch. She tried to maintain eye contact, despite the sinking feeling in her stomach. Madison's gaze was unyielding, a mix of curiosity and challenge as she continued to inspect Kylee's face. "You see, this is why the transformation is so important," Madison continued, her voice a mix of criticism and cool analysis. "You look better as a girl, Kylee. The makeup, the clothes—they bring out a beauty you just don't have naturally. You should be thanking me for helping you discover this."

Kylee swallowed hard, her pulse quickening with a mix of shame and reluctant agreement. She felt the weight of Madison's words settle over her, a strange, unsettling truth that she couldn't deny. "Thank you, Miss," she replied quietly, her voice trembling slightly with the intensity of the moment. The formal address felt natural in the charged atmosphere, a recognition of Madison's authority and her own submissive acceptance of the truth being laid bare.

Madison's lips curled into a satisfied smirk, her eyes glinting with a mix of triumph and challenge. "Good girl," she purred, her voice a soft, almost caressing whisper. "Remember that.

Madison's eyes narrowed slightly as she observed Kylee's precise and deliberate application. She began by applying a smooth, even layer of foundation, her movements confident and practiced. The soothing routine of blending the foundation calmed her nerves, grounding her as she focused on the task at hand.

The foundation was followed by a subtle blush that highlighted Kylee's cheekbones with a warm, natural glow. Each stroke of the brush was measured and intentional, reflecting the countless hours of practice Kylee had dedicated to mastering her look. She moved on to her eyes, selecting a palette of soft, neutral tones that complemented her features beautifully.

The eyeshadow blended seamlessly, creating a gentle gradient that enhanced Kylee's eyes without overpowering them. She applied eyeliner with a steady hand, a sleek line that framed her eyes perfectly, followed by a few coats of mascara that made her lashes long and fluttery. Madison's expression shifted as she watched, a flicker of surprise crossing her face as she realized Kylee's skill and confidence were far beyond what she had anticipated.

Finally, Kylee chose a delicate, rosy pink for her lips, adding a hint of gloss for a luscious finish. As she completed the look, she glanced up at Madison, her eyes reflecting a mix of nervous anticipation and quiet pride. "I'm finished," she said, her voice steady despite the tension in the room. "What do you think?"

Madison stepped closer, her gaze scrutinizing Kylee's reflection with an intensity that was both unsettling and thrilling. The makeup was flawless, enhancing Kylee's natural beauty with a grace and sophistication that spoke volumes about her dedication and practice. Madison's initial skepticism gave way to a grudging admiration, a hint of approval mingling with her ever-present air of challenge. "Not bad," she admitted, her voice tinged with reluctant respect. "You've clearly been practicing. I didn't expect you to look this good."

Kylee's heart swelled with pride at the compliment, her cheeks flushing with a mix of relief and satisfaction. "Thank you, Miss," she replied, her voice filled with genuine gratitude and a touch of strength.

Madison's predatory smile widened as she stepped back, her eyes gleaming with satisfaction after inspecting Kylee's bare face and seeing her transformed state. "Now that you've proven you can handle your makeup, there's something more challenging for you tonight," Madison said, her tone both authoritative and laced with anticipation. "You will need to seduce a man of my choosing at tonight's party. You'll do exactly what I tell you to do. No hesitation, no questions."

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i wish i was this good at makeup,,,don't forget to leave a vote <3

-lily