The Headmistress’s Obsession

Madeline stood tall and proud, her commanding presence filling the small office as she prepared for the day’s auditions. At fifty three years old, she was still an imposing figure, her hair neatly styled, and her sharp eyes missing nothing. As the headmistress of the prestigious all-boys school, she took great pride in her work, especially when it involved the young men under her care. She had a particular interest in their development, specifically in the area of their manhood.

The school was renowned for its unique approach to education, focusing on nurturing and guiding boys towards a strong and healthy manhood. And one of the ways Madeline believed they achieved this was by celebrating the very essence of masculinity—the penis. The campus was adorned with numerous statues of nude young men, their sculpted bodies a testament to the school’s ideals. However, for this new statue, Madeline had a specific vision in mind, one that would truly showcase the school’s most prized asset.

“I want this statue to be a symbol of our school’s prowess,” she had announced to her staff. “We will honor the boys’ journey to manhood by showcasing the very tool that defines their virility.” The staff, well accustomed to Madeline’s unconventional methods, nodded in agreement, knowing that this would be yet another intriguing project.

Madeline had a keen eye for detail, and she was determined to find the perfect model for the statue. She wanted a boy with a penis that would make jaws drop, a true embodiment of male power. And so, she sent out a notice for auditions, inviting the senior students to participate in what would be a unique and intimate
experience.

On the day of the auditions, a line of nervous yet eager eighteen-year-old boys formed outside her office. Each one had heard whispers about the nature of the tryouts, and their curiosity, mixed with a healthy dose of bravado, had brought them here. They knew of Madeline’s reputation, and the thought of standing before her, exposing their most private parts, was both thrilling and terrifying.

Madeline sat behind her large desk, a measuring tape and a small bowl within easy reach. She wore a dark blue dress that accentuated her ample bosom, a subtle reminder of her femininity in this male-dominated environment. As the first boy entered, he couldn’t help but notice her intense gaze, and he felt his nerves
tighten.

“Relax, dear,” Madeline said, her voice like silk. “This is a safe space. I want you to be comfortable, to embrace your masculinity and show me what you’ve got.” The boy, tall and lanky, with a shy smile, nodded, his eyes fixed on the floor.
“What’s your name, dear?” she asked gently.

“Ethan, ma’am,” he mumbled.

“Well, Ethan, let’s begin, shall we? Undress for me, and let’s see if you have what it takes.” Ethan’s heart raced as he slowly started to remove his clothes. His hands trembled as he unbuttoned his shirt, revealing a lean, muscular torso. He was in good shape, a result of the school’s emphasis on physical education.
As he pushed his pants down, Madeline’s eyes widened slightly. Ethan’s penis, already semi-erect, was impressive. It hung thick and heavy, the head peeking out from beneath his foreskin. Madeline licked her lips, a subtle sign of her growing excitement.

“Oh, Ethan, that’s a fine start,” she purred. “Now, let’s see how well you respond to a little stimulation.” She picked up a small, sleek vibrator from her desk, causing Ethan’s eyes to widen in surprise. “Don’t worry, dear, this will help us get an accurate measurement.”

With a flick of a switch, the vibrator buzzed to life, emitting a soft, tantalizing hum. Madeline ran the tip along Ethan’s inner thigh, making him shiver. She then gently grazed his balls with the vibrating toy, causing his breath to catch. As she slowly moved the vibrator up and down his shaft, Ethan’s penis responded, growing harder and longer with each pass.

Madeline watched with satisfaction as Ethan’s cock thickened and lengthened, reaching an impressive eight inches. She wrapped the measuring tape around the base, noting the girth, before moving it to the tip, measuring the length.

“Excellent, Ethan. You have a beautiful penis, and I can see it responds well to
stimulation.”

Ethan, now fully erect, felt a mix of pride and embarrassment as Madeline admired his manhood. She instructed him to stroke himself, and as he did, she observed the way his hand moved, the rhythm he naturally fell into.

“Good, good,” she encouraged. “Now, I want you to edge. Bring yourself to the brink of orgasm, but don’t let go just yet.”

Ethan’s eyes rolled back slightly as he complied, his hand moving faster, his breath coming in short gasps.

Madeline watched with keen interest, her own excitement building as she witnessed his struggle to control his release. After a few minutes, she stopped him.

“Very good, Ethan. Now, I want you to ejaculate into this bowl.” She held up the small container, and Ethan, his cock throbbing, aimed his pulsating head at the target. With a few more strokes, he exploded, his cum shooting out in thick, white ropes, filling the bowl with his seed.

Madeline smiled, satisfied with Ethan’s performance. “Well done, dear. You may dress now and return to your dorm. I will be reviewing all the auditions and will announce the winner soon.”

Ethan, his heart still pounding, quickly dressed and left the office, his mind reeling from the experience. Boy after boy entered Madeline’s office, each one putting on a unique display of their manhood. Some were already well-endowed, their penises standing proudly at attention, while others needed a little encouragement from Madeline’s skilled hands and toys. She measured each one, noting their length and girth, and had them ejaculate, observing the volume and consistency of their cum.

There was Sebastian, a quiet boy with a shy smile, who revealed a thick, uncut cock that grew to an impressive nine inches when stimulated. He blushed deeply as he stroked himself for Madeline, his cum spurting out in powerful bursts, coating the bowl with his essence.

Another boy, Oliver, had a lean, athletic build and a cock that was already semi-erect when he entered. With Madeline’s expert touch, it grew to a solid eight inches, and he came with a passionate groan, his body trembling as he filled the bowl with his warm, creamy load.

As the auditions continued, Madeline’s excitement grew. She had seen some truly remarkable penises, each one a work of art in its own right. But she was waiting for that one boy who would embody the essence of the statue she envisioned—the ultimate symbol of male virility.

Then, as the day was drawing to a close, the final boy entered. His name was Lucas, and he had a confident stride and a mischievous grin that hinted at a playful nature. His eyes sparkled with a hint of challenge as he took in the scene, the measuring tape and bowl on the desk giving away the nature of the auditions.
“Well, well, Lucas,” Madeline said, her voice filled with anticipation. “I’ve been waiting for you. Let’s see if you can impress me.”

Lucas smirked, his confidence growing as he began to undress. His body was lean and toned, with a light dusting of hair leading down from his navel to his groin. As he pushed his boxers down, Madeline’s breath caught. Lucas’s penis was a work of art. It was long and thick, the head a deep purple, already glistening with pre-cum. It stood proudly, reaching just below his navel when fully erect, a true testament to his virility.

Madeline’s eyes widened as she measured his length, the tape extending to a remarkable ten inches. His girth was equally impressive, making her wonder how she would capture such a magnificent specimen in a statue.

“Oh, Lucas, you have a truly remarkable penis,” she said, her voice thick with desire. “Now, let’s see your control.”

Lucas, his cock throbbing with anticipation, began to stroke himself. His hand moved with a slow, deliberate rhythm, his eyes locked with Madeline’s. She watched, mesmerized, as he brought himself closer and closer to

the edge. His breathing quickened, and his hand moved faster, but he maintained control, his body trembling with the effort.

“That’s it, Lucas,” Madeline encouraged, her voice hoarse with arousal. “Show me your power, your control.

Make yourself wait, and then release with all the passion you can muster.”

Lucas’s eyes rolled back, and with a final, powerful stroke, he let go. His orgasm ripped through him, and he cried out, his body shaking as he filled the bowl with his cum. Rope after rope of thick, white liquid spurted from his cock, a testament to his virility and endurance.

Madeline was breathless, her body tingling with desire. She had found her winner. Lucas’s penis, with its impressive size and his ability to control and unleash his orgasm, was the perfect embodiment of what she sought for the statue.

“Congratulations, Lucas,” she said, her voice steady despite her racing heart. “You will be the model for our new statue. The sculptor will be here in a week, and I want you to be ready to pose for him.”

Lucas grinned, his chest swelling with pride. “I’ll be ready, ma’am. I promise to give it my all.”

As Lucas left the office, Madeline couldn’t help but feel a sense of satisfaction. She had found the perfect boy, and now the school would have a statue that would truly showcase its most well-endowed student. The thought of seeing Lucas’s magnificent penis immortalized in stone excited her, and she couldn’t wait for the sculptor to arrive, knowing that this would be a project unlike any other.

Little did the boys know, as they returned to their dorms, that their headmistress had a deep-seated passion for their manhood, and that this statue would be a lasting tribute to the school’s unique approach to education and the celebration of male virility.

The first chapter ends here, with the selection of Lucas as the model for the statue, but the story of Madeline’s obsession with the boys’ penises and her unique approach to education is far from over. The sculptor’s arrival and the creation of the statue will bring new twists and turns, and the boys will soon discover that their headmistress’s interest in their manhood goes far beyond mere academic curiosity.

Forbidden Temptation

The air was thick with anticipation as Roy found himself alone in the house with his stepmother, Kate. It was a rare opportunity, one he had been eagerly awaiting. With his father away on a business trip, Roy’s desires for Kate had intensified, and he was determined to make his move.

Roy, an eighteen-year-old with a charming, fresh-faced schoolboy look, had always been captivated by Kate’s beauty. She was a stunning woman, shorter than him with a petite frame, her blonde hair falling just above her shoulders, and her green eyes sparkling with a playful glint. At forty-eight, she had an ageless allure, her lean body exuding a youthful energy that belied her years.

Kate had been a part of Roy’s life for as long as he could remember. She was always there, a constant presence, but as he grew older, his feelings towards her evolved from innocent admiration to something far more lustful. The sexual tension between them was palpable, a silent understanding that something forbidden was brewing.

On this particular day, Roy’s father had kissed Kate goodbye at the front door, his briefcase in hand, and a promise to return in a week. As soon as the door closed, Roy felt a surge of adrenaline. He knew this was his chance.

He made his way upstairs, his heart pounding in his chest. The house was eerily quiet, and he could hear the ticking of the grandfather clock in the living room, marking each passing second. Roy paused outside Kate’s bedroom, his hand resting on the doorknob, hesitating for a moment before turning it slowly.

The room was dimly lit, the curtains drawn, creating an intimate atmosphere. Kate’s bed was neatly made, the covers smooth and inviting. Roy’s eyes scanned the room, taking in the familiar surroundings, and his gaze fell upon Kate’s dressing table. It was a sight he had imagined countless times, her personal sanctuary.

On the table, a collection of perfumes and cosmetics were neatly arranged, but what caught Roy’s attention was a lacy black bra, hanging seductively on the edge of the mirror. It was a bra he had seen Kate wear on several occasions, and the sight of it sent a jolt of desire through his body.

Without thinking twice, Roy stepped into the room, closing the door behind him. He approached the dressing table, his fingers tracing the delicate lace of the bra, imagining how it would feel against Kate’s soft skin. He picked it up, holding it to his face, inhaling her subtle scent, a mixture of lavender and vanilla.

“What are you doing, Roy?”

The sudden sound of Kate’s voice startled him, and he spun around, his heart racing. There she stood, at the doorway, her eyes wide with surprise. Roy’s face flushed with embarrassment as he realized he had been caught red-handed, holding her lingerie.

“I… I was just…” Roy stuttered, his voice cracking.

Kate’s eyes narrowed, and a slow smile spread across her lips. “You were curious, weren’t you?” she said, her voice low and husky. “I’ve seen the way you look at me, Roy. I know you’ve been fantasizing about me.”

Roy’s mouth went dry. He couldn’t deny it, not after being caught in such an intimate act. “I… I have, Kate,” he admitted, his voice barely above a whisper.

Kate took a step towards him, her eyes never leaving his. “And what do you fantasize about, Roy? Tell me.”

Roy’s mind raced, his body trembling with a mixture of excitement and nervousness. He had never been so bold, but something about Kate’s presence emboldened him. “I… I imagine touching you, feeling your soft skin,” he said, his voice gaining confidence. “I think about how you’d feel wrapped around me, how you’d moan my name.”

A low, throaty laugh escaped Kate’s lips. “Oh, Roy, you have no idea how long I’ve been waiting to hear you say that.” She took another step forward, closing the distance between them. “I’ve been thinking about you too, you know. Ever since I caught you staring at me during dinner, I’ve been wondering what it would be like to have you.”

Roy’s breath quickened as Kate’s words sunk in. He had always hoped she felt the same way, but hearing it from her lips was electrifying. “You want me too?” he asked, his voice laced with disbelief.

“More than you know,” Kate replied, her hand reaching up to caress his cheek. “I’ve been a good stepmother, but I’m a woman with desires too. And you, my dear stepson, are the object of my fantasies.”

Roy’s body responded to her touch, his cock hardening at her words. He leaned into her hand, savoring the sensation of her soft skin against his. “I want to make those fantasies come true, Kate,” he said, his voice hoarse with desire.

Kate’s eyes darkened with lust as she took in the bulge in his pants. “Oh, I think we can make that happen,” she purred. “But first, let’s take care of this.” She reached for the zipper of his jeans, slowly pulling it down, her fingers brushing against his hardening length.

Roy’s breath caught in his throat as Kate’s hand wrapped around his throbbing cock, still encased in his boxer briefs. She gave it a gentle squeeze, making him gasp. “You’re so hard for me, Roy. I love it.”

“I’ve been hard ever since I saw you this morning,” he confessed, his voice strained. “I can’t control it when you’re around.”

Kate smiled, her fingers stroking him through the fabric. “I want to see it, Roy. I want to see what you’ve been hiding.”

With trembling hands, Roy pushed his jeans down, revealing his erect shaft, straining against the thin fabric of his underwear. Kate’s eyes widened at the sight, her breath quickening. “Oh, my,” she whispered, her hand reaching out to stroke him through the briefs.

“I want to feel you, Kate,” Roy pleaded, his voice thick with need. “Please, let me show you how much I want you.”

Kate’s fingers hooked into the waistband of his underwear, slowly pulling them down, revealing his thick, pulsating cock. She let out a soft moan as she took in the sight, her eyes fixated on the glistening head. “You’re beautiful, Roy,” she said, her voice filled with admiration.

Roy stepped out of his clothes, standing before her completely naked, his cock standing proudly, begging for her touch. Kate’s eyes traveled up and down his body, taking in his youthful, toned physique. “You’re a gorgeous young man,” she whispered, her hand reaching out to stroke his chest.

Roy’s breath hitched as Kate’s fingers trailed down his abdomen, closer to his aching cock. “I want to taste you, Kate,” he said, his voice hoarse. “I want to feel your mouth on me.”

Kate’s eyes flickered up to meet his, a mischievous smile playing on her lips. “Oh, I plan to taste every inch of you, Roy. But first, I want to watch you touch yourself. I want to see how you like to be touched.”

Roy’s heart raced as he realized what she was asking. He had never masturbated in front of anyone, but the thought of Kate watching him was incredibly arousing. He nodded, his hand reaching down to wrap around his shaft, slowly stroking himself.

“That’s it, Roy,” Kate encouraged, her eyes fixed on his hand moving up and down his length. “Show me how you like it. Do you like it slow and gentle, or do you prefer it rough?”

Roy’s hand tightened around his cock, his strokes becoming more urgent. “I like it when it’s hard and fast, Kate,” he grunted, his eyes never leaving hers. “But I want to feel your touch, more than anything.”

Kate’s breath quickened as she watched him. “I can see how much you want me, Roy. Your cock is so hard, so ready for me.” She took a step closer, her hand reaching out to guide his strokes. “Let me help you, baby. Let me make you feel good.”

Roy’s eyes rolled back as Kate’s hand joined his, their fingers entwined as they stroked his length together. Her touch was electric, sending waves of pleasure through his body. “Oh, Kate, yes,” he groaned, his hips thrusting into their hands.

“That’s it, Roy,” she whispered, her breath hot on his ear. “Let go, let me feel you cum for me.”

Roy’s body tensed as the pleasure built, his orgasm approaching with relentless force. “I’m close, Kate,” he panted. “So close.”

Kate’s hand moved faster, her thumb rubbing the sensitive tip of his cock, driving him wild. “Cum for me, baby,” she urged, her voice a husky command. “Let me see it, let me feel your hot cum on my hand.”

With a guttural cry, Roy’s body convulsed, his cock throbbing as he shot his load, his warm cum coating their entwined hands. Kate’s fingers continued to stroke him through his release, milking every last drop from his spent shaft.

As Roy’s breathing slowed, Kate brought their cum-covered hands to her mouth, her eyes never leaving his. “Mmm, you taste delicious, Roy,” she purred, licking their combined essence from her fingers. “I can’t wait to taste you properly.”

Roy’s cock twitched at her words, already showing signs of recovery. He reached for her, pulling her close, his hands exploring her curves. “I want to taste you too, Kate,” he whispered, his lips brushing against her ear. “I want to make you feel as good as you just made me feel.”

Kate’s body trembled at his touch, her nipples hardening against the fabric of her dress. “Oh, Roy, you’re going to drive me wild,” she breathed, her hands sliding down to cup his firm ass. “But first, we should probably take this to the bedroom, don’t you think?”

Roy’s lips curved into a mischievous smile as he took her hand, leading her towards the bed. “Oh, I have a feeling this is just the beginning, Kate,” he said, his voice filled with anticipation. “And I plan to make every one of your fantasies come true.”

As they lay down on the bed, their bodies entwined, Roy’s hand sliding beneath her dress, Kate’s breath quickened, her eyes sparkling with desire. “I can’t wait, Roy,” she whispered, her lips finding his in a passionate kiss. “I’ve been waiting for this moment for far too long.”

The story continues, as Roy and Kate’s forbidden desires ignite, leading them down a path of sensual exploration and unbridled passion…