Crossdressing Stories - Feminised by Mom’s Friend

Published on Dec 30, 2023 by Tohka Crow

Amid the storm, Noah's thoughts raced as quickly as the windshield wipers swishing across the glass, barely keeping up with the downpour. "Is this such a good idea?" he wondered aloud, the wipers responding in their rhythm as the only sound in the car's interior. His hands clenched around the steering wheel, feeling the cold dampness seeping through his jacket from the rain-soaked collar.

His mother's voice crackled from the phone speaker. "Noah, go to Layla's, she owes me one." He knew nothing of Layla except the bare details his mother often related. He'd never met her, but the strength of his mother's insistence left little room for argument. A part of him was intrigued, a flicker of curiosity sparked amidst the storm. "Alright, mom," he murmured, the unease in his gut echoed by the harsh scream of the wind outside.

The drive to Layla's seemed to stretch on, the oppressive dark turning familiar roads into unfamiliar territories. The rain pelted down, casting everything in a shroud of uncertainty. "Just one night," he reassured himself, the windshield reflecting his tense expression amidst the constant flicker of the wipers.

Layla's house rose from the storm, an island of warm light amidst the tempest. It was a sight for sore eyes, the lit windows beckoning him in. The rain was merciless, soaking him through as he sprinted up to the front porch, and into the relative shelter it provided. "Almost there," he muttered, watching the water pooling around his shoes, his heart pounding in time with the raindrops falling.

His wet hand thumped against the door, the sound swallowed by the thunder echoing across the sky. Inside, a shadow moved, an anticipation built in him, a sudden awareness of his situation. "This is it," he thought, his nerves tangled up with a twinge of excitement. The unknown was a step away, hiding behind the creaking door.

The door creaked open, and there she was. Tall and imposing, her silhouette framed by the warm light behind her. Long, dark hair cascaded over her shoulders, a sharp contrast against her creamy skin. Her curvy figure was outlined by a fitted dress that accentuated her generous assets. His eyes involuntarily swept over her, landing on the ample swell of her breasts. A hot wave of intimidation washed over him, but it was quelled, momentarily at least, by the welcoming smile that softened her strong features.

"Come in, Noah," she beckoned, her voice a smooth melody that rolled over his name. Noah found himself stepping inside without hesitation, the warmth of the house instantly seeping into his rain-chilled bones. He took off his drenched coat, feeling acutely aware of her gaze upon him.

In the living room, the crackling fire played with shadows on her face, deepening the intrigue she held. "Your mom mentioned you'd be dropping by. I can't say no to an old friend," she said, her eyes glinting with a playful glint. "Make yourself comfortable, Noah," she offered, gesturing to the plush couch.

"I'm not sure what my mother told you..." Noah began, his words trailing off. His gaze wandered to the pictures on the mantelpiece, one of them a younger Layla with his mom. The realization of the bond between them, the shared past, it made him feel even more out of place.

Layla's voice broke into his thoughts, a soothing balm to his unease. "Your mom and I go way back, Noah. Tonight, you're not just her son. You're my guest, and I intend to make you feel at home." The assertiveness in her tone was wrapped in warmth, and Noah found himself silently hoping that he would manage to feel at ease in this unfamiliar setting.

After shedding his soaked garments, Noah wrapped himself in the plush robe that Layla had handed him, its fabric soft against his skin. She directed him towards the bathroom, where he found a hot bath waiting for him, the water scented with something sweet. The luxury of the bath, the steam curling up in the room, the soothing scent, it was all so overwhelming, so far from his modest student accommodations.

Immersing himself into the warm water, he sighed in contentment, but after a few moments, he felt an odd sensation. Looking down, he saw his body hair loosening and drifting off. Shocked, he exited the bath, the lotion-infused water clinging to him causing more hair to fall out.

"Layla," he called out in alarm, his voice laced with humiliation. There was a moment of silence before Layla appeared, a look of surprise on her face that soon turned into apologetic realization. "Oh dear, I used the wrong bottle. That's a hair-removal lotion. I am so sorry, Noah."

His embarrassment only grew when she presented him with the only clothing she had that might fit him – a silky pair of pajamas, clearly feminine in design. There was no other choice, so he slipped into them, feeling his cheeks heat up. The mirror reflected back a smooth, feminine version of himself, a sight so alien that it was almost laughable.

When he emerged, Layla's eyes scanned him, her gaze making his skin tingle. She broke out into a grin, "Well, aren't you the prettiest girl?" Her teasing words, intended to embarrass, strangely spurred something inside him, a fluttering sensation in his belly. He found himself nervously fiddling with the hem of the nightgown, unsure of what was to come next.

They enjoyed a simple dinner, the chatter light and superficial. Afterward, they settled on the plush living room sofa, a classic movie playing on the large flat-screen TV. Layla excused herself to the kitchen, leaving Noah alone.

His eyes fell on a shiny object on the coffee table - a lipstick tube. The curiosity was too much, he reached for it, uncapping the tube to reveal a rich, ruby-red lipstick. It was such a contrast to the virile persona he had always upheld, and yet the color seemed so vibrant, so full of life. His heart pounded in his chest as he held it, tempted by the unknown.

The sound of Layla's footsteps snapped him back to reality, and he hastily tried to cap the lipstick tube, but it was too late. Layla, walking back into the room, a warm smile on her face, caught him in the act. She chuckled, "Oh, Noah, couldn't resist the allure of being a girl for a night, could you?"

A flush of embarrassment heated his cheeks, but he couldn't find words to reply. She had a glint of mischief in her eyes, using feminine names and teasing him. The humiliation was there, yes, but beneath it was a sense of anticipation. This evening was turning out to be something Noah had never expected.

"Well, since you seem so interested, why don't we make a night of it?" Layla suggested, her tone playful yet assertive. Noah felt a pang of apprehension but kept quiet as she fetched a nail polish bottle from a drawer. He obediently held out his hands, watching as she meticulously painted each nail with a glossy, candy pink. The scent of the polish filled the air, and the cold, tingly sensation on his nails made him squirm.

"Now, isn't this fun?" Layla asked, her voice dripping with sarcasm. Noah kept silent, his embarrassment morphing into a sort of resigned acceptance. There was an odd thrill to this submission, something he'd never felt before.

Next came the makeup. Layla expertly applied a light foundation, dusted his cheeks with blush, and then touched up his eyelashes with mascara. Noah could feel the brush's soft bristles against his skin, making him hyper-aware of every detail.

"Lay back, dear," Layla instructed, taking an eyebrow plucker from a makeup bag. "This might sting a little." Noah obeyed, shutting his eyes tightly as she plucked stray hairs, shaping his eyebrows to a more delicate arch.

When she was done, Layla held up a mirror, allowing him to see the transformation. Despite the humiliation, he couldn't help but marvel at how different he looked. "You're such a good girl, Noah," she said, her voice gentle yet mocking. "I think it's time you embraced the girly sleepover spirit. You never know, you might enjoy it." The comment filled him with a strange mix of dread and curiosity. What would come next?

"And now, the finishing touch." Layla disappeared for a moment and came back with a wig of long, straight brown hair. It was strikingly similar to Noah's own hair color. She gently placed it on Noah's head, arranging it until it fell perfectly around his shoulders. Noah sat in silence, the weight of the wig on his head foreign yet oddly comforting.

With a satisfied smile, Layla sat back and surveyed her handiwork. "I can't deny it. You truly are your mother's son," she mused, her eyes twinkling with amusement. "You look just like her when we first met. We were about your age, working our first job together."

Noah looked at himself in the mirror again, the woman staring back at him almost unrecognizable. He was a surreal reflection of his mother from a time before he existed, a memory of her youth replicated through him. Layla's incessant teasing, referring to him as a girl, only furthered his bewilderment.

He felt a strange mix of emotions. There was the clear humiliation of being made to look like a woman. But there was also a hint of intrigue, a curiosity about this feminine image he saw in the mirror. Would he have been different if he had been born a girl? The thought was unusual, and he wasn't sure what to do with it, but it certainly had him questioning himself. He was in uncharted territory, unsure of his next move.

Noah glanced at his reflection, his own feminized face looking back at him. He was encased in soft femininity, an alternate universe version of himself. The long brown wig cascaded around his shoulders, framing his face. His usually stark features were softened by the makeup and the change was jarring, yet strangely alluring.

What did this mean about him? Noah wondered. He was caught in a whirlwind of emotions, but most surprising of all, there was an undertone of... excitement? His heart throbbed with an odd fascination.

The notion of his appearance embodying femininity, the softness of the clothes against his skin, even the pretty polish on his nails – they stirred within him an unfamiliar, complex sentiment.

His mind whirled back to the evening's events with Layla. Her confident demeanor, the teasing way she'd turned him into her personal doll for the evening, it was all so new to him. It was intimidating yet strangely thrilling. His cheeks warmed up remembering Layla’s laughter, the gleam in her eyes as she admired her handiwork.

As he lost himself in the mirror, he couldn't help but ponder. He felt vulnerable, yet empowered. Confused, yet intrigued. The line of his own masculinity felt blurred, and he found himself questioning his own identity. Was he comfortable in this unfamiliar skin? He wasn't sure yet. But he couldn't deny the strange, titillating thrill it brought him. He sat there, staring at the woman in the mirror, lost in his swirling thoughts.

As the movie ended and the credits rolled, Noah was consumed by an odd mix of feelings. His mind was a carousel of thoughts, spinning between the reality of the moment and the absurdity of the experience. They said their goodnights, the silence of the house echoing the hushed wonder of the night.

In the morning, Layla fluttered around the kitchen, her movements as fluid and graceful as the day before. Noah's clothes, now dry, hung neatly by the door. But it was the dainty, lacy garment on top that caught his attention - a souvenir, Layla playfully called it.

"Don't worry, you can decide what you want to do with them," she said, her words echoing in his mind. The panties were a soft pink, delicate to touch, as if it was a testament to the previous night.

He found himself deciding to wear them underneath his regular male clothes, an inexplicable urge guiding him. A quiet thrill coursed through him as he did so. It felt like a secret, a hidden part of him concealed from the world.

As he bid goodbye to Layla, the clear blue sky greeted him, a stark contrast to the previous day's storm. It felt symbolic in a way, a calm after a storm. The sun was bright, bathing everything in a warm glow as he got into his car and began his journey back home. His mind wandered back to the previous night, lost in thoughts about his unusual experience. As the miles rolled by, he could only wonder what this new experience meant for him.