Mrs. Mendelson’s Boarding House and some its the residents were introduced in “Anna’s Story.” This story was written first and it seemed like a lovely setting for that story. Oddly, I realized that I had used the name, Anna, for a minor character in this story before I selected the boarding house for the final act of the more serious “Anna’s Story.” The setting and a few characters are really the only connection. This story is more whimsical and I hope you enjoy it!

* * *

Todd Allen arrived in town, his heart heavy with desperation. He was in need of a place to stay for a month-long training course, but fate seemed determined to thwart his plans. Apartments demanded leases, and hotels insisted on nightly rates that far exceeded his modest budget.

He was directed to a quaint boarding house named Mrs. Mendelson’s Boarding House. It was owned by a captivating woman named Mrs. Mendelson, a widow of elegant beauty and a reputation for strict rules. Mrs. Mendelson’s Boarding House was a place where young women sought refuge, each with their own secrets and dreams.

With limited options, Todd was driven to seek accommodation at the boarding house. Determined to persuade Mrs. Mendelson that he posed no threat, he arrived at the boarding house, his earnest eyes meeting her piercing gaze.

“Mornin’, ma’am,” Todd greeted, his voice tinged with charm. “I have a predicament. I’m in dire need of a room, and I assure you, I’m as safe as a newborn lamb.”

Mrs. Mendelson scrutinized Todd, her emerald eyes assessing him from head to toe. She noticed his broad shoulders, the strength in his arms, and the untamed energy that radiated from him.

“Safe, you say?” she replied, her voice dripping with skepticism. “My girls here are fragile blossoms, and I’ll be damned if I let a boy like you disturb their peace. How do I know you won’t succumb to your primal urges?”

Todd’s eyes locked with Mrs. Mendelson’s, a flicker of determination gleaming within them. “Ma’am, I give you my word. I’ll do whatever it takes to prove my worthiness. I’ll swear an oath on my honor.”

Mrs. Mendelson said, “If you were a girl, I could lock you in a chastity belt, but I don’t think they make them for little boys.” Her voice carried a hint of amusement, a subtle challenge to Todd’s determination.

Todd, undeterred, leaned closer, his voice laced with a smoldering confidence. “Mrs. Mendelson, I assure you they do and if you believe that a piece of metal is necessary to contain the depths of my longing, then I shall be happy to accept any condition.”

A mischievous glimmer danced in Mrs. Mendelson’s eyes as she considered Todd’s audacity. “Very well, Mr. Allen,” she purred, her voice dripping with anticipation. “If you are willing to subject yourself to such a restriction, then I shall procure a boy’s chastity belt, and you shall wear it under my watchful eye.”

Mrs. Mendelson went on Amazon and was amazed variety of chastity devices available. She turned to Todd and asked “What size are you?”

Todd answered, “Uh… medium?”

Mrs. Mendelson tsked and said “That won’t do. We need length and girth, both flaccid and erect, and ball ring size. Let me get my tape measure.”

As Mrs. Mendelson retrieved her tape measure with a glint of determination in her eyes, Todd’s heart raced with a mix of anticipation and nervousness. He watched as she approached him, unceremoniously unfastening and dropping his pants and pulling down his underwear, her fingers delicately holding his cock.

“Stand straight and still, young man,” Mrs. Mendelson commanded, her voice carrying a hint of authority mingled with an undercurrent of excitement. “We shall leave no room for uncertainty in our quest for the perfect fit.”

With measured precision, Mrs. Mendelson began her examination, the tape measure gently encircling Todd’s manhood. Her touch was both clinical and arousing, her eyes focused on the task at hand as she recorded the vital statistics that would guide their journey.

Todd stopped breathing as he felt the pressure of the tape against his flesh, the sensation igniting a fire within him. He shifted, struggling to maintain his composure as Mrs. Mendelson recorded the measurements with meticulous detail.

“Six inches in circumference,” Mrs. Mendelson murmured, her voice betraying a mixture of awe and satisfaction. “A respectable length of five and a half inches at rest. And when aroused…” she stroked him until he was erect, “a glorious transformation to seven and a half inches long and six and a half in circumference.” She raised an eyebrow, a glimmer of satisfaction dancing in her eyes. “Quite impressive, Todd.”

But Mrs. Mendelson’s examination was not yet complete. With a steady hand, she moved to measure the circumference around Todd’s cock and balls, her touch gentle yet purposeful as she pulled the tape tight beneath his testicles. Her fingers lingered for a moment, eliciting a gasp from Todd, before she noted the size of the ball ring required to hold the cage in place.

Once the measurements were complete, Mrs. Mendelson locked eyes with Todd, a devilish smile curving her lips. “Now we have the information we need, Todd,” she purred. “With this knowledge, we shall lock you away.”

And so, armed with the precise measurements of Todd’s manhood, Mrs. Mendelson embarked on a journey of exploration and discovery. She scoured Amazon’s vast collection of devices, carefully selecting the ones that would perfectly accommodate Todd’s size and her wishes.

Finally, Mrs. Mendelson said, “There are too many choices. I’ll have to order several and we can try them one at a time until we find the right one. They offer two-day delivery. Until then, you will stay in my room where I can keep you under my watchful eye.”

She looked at him in businesslike fashion and said, “You shall do as I say, young man and we’ll get along fine. Disobey and there will be consequences. Follow me.”

As Mrs. Mendelson’s voice took on a firm tone, Todd’s heart quickened with a mixture of anticipation and apprehension. Silently, Todd nodded, acknowledging Mrs. Mendelson’s authority. He followed her, his steps measured and deliberate, as she led him through the hallways of the boarding house.

Upon entering Mrs. Mendelson’s room, Todd took in the opulent surroundings, a reflection of her refined taste and desire for control. The air was heavy with the scent of candles, their flickering flames casting seductive shadows upon the walls. It was a sanctuary of dominance and surrender.

“Give me your clothes, Todd,” Mrs. Mendelson commanded, her voice laced with authority. “From this moment forward, you shall be under my watchful eye. Every move, every thought, shall be subject to my scrutiny. “

Without hesitation, Todd obeyed, slowly shedding his garments until he stood in his boxers before Mrs. Mendelson, his vulnerability on display.

“Those too,” she motioned at his underpants. With a blush he lowered his drawers, stepping out with a clumsy hop, and, without making eye contact, self-consciously handed them to Mrs. Mendelson. He felt the weight of her gaze upon him, her eyes dissecting his every inch with a calculated precision.

Mrs. Mendelson unconsciously licked her lips as she admired his thick cock once again, took his clothes and spoke, “Your clothes will be returned to you tomorrow morning. Get ready for bed.”

* * *

Todd returned from his day of training, the weight of knowledge and experience settling upon him. As he entered the dining room of Mrs. Mendelson’s Boarding House, the aroma of delicious food filled the air, mingling with the laughter and chatter of the other residents.

The room was adorned with a warm ambiance, the walls adorned with intricate tapestries that told stories of passion and liberation. The girls of the boarding house sat at the table, their eyes lighting up as Todd entered the room.

Their gazes, a mixture of curiosity and intrigue, followed Todd as he made his way to an empty seat. The residents welcomed him with smiles and friendly nods, their conversations momentarily pausing to acknowledge his presence.

Seated beside Todd was Anna, a vibrant and vivacious young woman with light brown locks that highlighted her fair skin and captivating features. She leaned toward him, a mischievous twinkle in her eyes.

“Welcome back, Todd,” she whispered, her voice a soft caress. “We’ve been eagerly awaiting the opportunity to meet you.”

Todd couldn’t help but feel a surge of warmth at Anna’s words, her playful demeanor inviting him into their tight-knit community. He returned her smile, his eyes sparkling with a mix of gratitude and curiosity.

As the meal commenced, the residents engaged in lively conversation, sharing stories and laughter that filled the room. Todd found himself enveloped in the vibrant atmosphere, gradually becoming acquainted with the unique personalities and desires of each resident.

Sarah, a tall, enigmatic and confident woman with an air of mystery, sat across from Todd. Her piercing gaze held a hint of intrigue, as if she held secrets waiting to be unveiled. She leaned forward, her voice a velvet whisper.

“You’ve certainly caught Mrs. Mendelson’s attention, Todd,” Sarah said, a knowing smile curling her lips. “She doesn’t bestow her trust easily, but there’s something about you that has piqued her interest.”

Todd’s brow furrowed slightly, curiosity mingling with a sense of pride. He had embarked on this journey to prove himself, to earn Mrs. Mendelson’s trust, and to become part of the tight-knit family of Mrs. Mendelson’s Boarding House.

“I’m grateful for her trust,” Todd replied, his voice carrying a mix of humility and determination. “I’m eager to get to know everyone.”

The conversation flowed, weaving a tapestry of shared experiences, desires, and dreams. Todd listened attentively, his genuine interest shining through as he connected with the unique stories and passions of each resident.

Throughout the dinner, Todd found himself drawn to the complex dynamics of the women, their distinct personalities complementing and challenging one another. From the spirited energy of Emma to the poised grace of Isabella, to the smoldering good looks of quirky Lydia, each resident brought a unique flavor to the boarding house.

And as the night settled over Mrs. Mendelson’s Boarding House, Todd couldn’t help but feel a sense of anticipation, knowing that within the walls of this extraordinary boarding house, his path of exploration and connection would continue to unfold, interconnecting with the stories and desires of the captivating women who called it home.

Mrs. Mendelson said, “I have errands to run. For safety’s sake, you will need to let me tie you to the bed while I’m gone. You understand.” Her last sentence was a statement, not a question, and left no room for argument.

Mrs. Mendelson’s words hung in the air, their weight sinking into Todd’s consciousness. He felt a mix of surprise and intrigue at her request, a reminder of the unique dynamics that existed within the walls of the boarding house. Todd gazed into Mrs. Mendelson’s eyes, a flicker of understanding passing between them.

“Yes, Mrs. Mendelson,” he replied, his voice tinged with a blend of anticipation and trust. “I understand the importance of the girls’ safety.”

With a firm yet gentle touch, Mrs. Mendelson led Todd to her private chamber. The room exuded an air of dominance and submission, its atmosphere heavy with the scent of desire and anticipation. Todd felt a surge of excitement mingled with a trace of vulnerability as he stood before the bed, awaiting Mrs. Mendelson’s instructions.

“Undress, Todd,” Mrs. Mendelson commanded, her voice resonating with authority. “We shall ensure that you are restrained in a manner that keeps you secure and under my watchful eye.”

Todd obeyed, slowly shedding his clothes until he stood naked before Mrs. Mendelson. He could feel her gaze upon him, her eyes exploring every inch of his exposed flesh. The vulnerability he displayed only heightened his awareness of the power dynamic that bound them together.

Mrs. Mendelson approached him, a glimmer of dominance in her eyes. She possessed a delicate balance of control and sensuality, a mix that ignited a fire within Todd’s being. With precise yet deliberate movements, she skillfully secured his wrists and ankles to the sturdy posts of the bed.

As the final knot was tightened, Todd found himself both physically and metaphorically bound to Mrs. Mendelson’s desires. The restraints held him captive, arms immobilized and legs spread wide, his vulnerability on display, a symbol of trust and surrender that left him breathless with anticipation.

Mrs. Mendelson pressed a tender kiss against Todd’s forehead, her touch a soothing balm against the vulnerability that coursed through him. “Rest assured, my dear boy,” she murmured, her voice a caress against his skin. “I shan’t be gone long.”

With those words lingering in the air, Mrs. Mendelson departed with his clothes, leaving Todd naked, tied spread-eagle to the bed, his mind awash with a whirlwind of emotions and possibilities. He surrendered himself to the moment, his senses heightened, as he awaited Mrs. Mendelson’s return.

And as the door to Mrs. Mendelson’s suite swung open, signaling her return, Todd’s heart quickened, aching for the touch of her hand, releasing him from his bonds.

As the lights flickered and plunged the room into darkness, Todd’s heart skipped a beat. The anticipation that had filled the air moments ago was replaced with a sense of unease, a realization that something unexpected was unfolding.

In the enveloping darkness, Todd strained his senses, trying to discern the presence that had entered Mrs. Mendelson’s chamber. He listened intently, the silence broken only by the sound of his own racing heartbeat.

A soft voice cut through the darkness, a voice that sent shivers down Todd’s spine. “Well, well, what do we have here? Tied up and waiting for your Mistress, are you?”

Fear mingled with a spark of intrigue as footsteps approached the bed. He could feel her presence, her energy radiating through the room, as she ran her fingers along the restraints that held him captive.

“You see, Todd,” she purred, her voice a seductive whisper, “Mrs. Mendelson may have entrusted you to her care, but I have other plans for you tonight.”

Todd’s mind raced, his senses heightened by the uncertainty of the situation. He was bound, vulnerable, and under the control of someone whose desires were unknown to him. It was a dangerous game, one that blurred the lines of trust and consent.

Todd’s breath caught in his throat as recognition flooded his mind. It was Lydia, one of the residents of the boarding house, known for her mischievous and unpredictable nature. What had started as a gesture of trust had taken an unexpected turn, and Todd found himself at the mercy of Lydia’s whims.

Lydia, the dark haired beauty, possessed a body that exuded an intoxicating allure. Her lips, soft and inviting, held the promise of passionate encounters. Her smallish breasts matched her slender frame, a tantalizing sight, perfectly shaped, complemented by a natural fullness that accentuated her femininity. Lydia’s ample ass had a beguiling sway and an enticing roundness that hinted at both comfort and temptation. Her legs, long and shapely, seemed to go on for miles, captivating with each step she took.

Lydia’s touch trailed along Todd’s exposed skin, her fingers leaving a trail of goosebumps in their wake. “You thought you were submitting to Mrs. Mendelson, but you’ve fallen into my web instead. Don’t worry, Todd, I promise you an experience you won’t soon forget.”

Lydia’s hands roamed between his spread legs, clutching his exposed balls, her touch both gentle and electrifying. Todd’s senses heightened as he surrendered himself to her desires, the anticipation of the unexpected driving his pulse to a rapid rhythm.

In the shroud of darkness, Lydia’s voice took on a commanding tone, her words resonating with authority. “You are mine now, Todd,” she declared, her breath hot against his ear. “Every touch, every sensation, shall be orchestrated by my will. Trust in me, and I shall lead you through a world of pleasure.”

Todd sharply inhaled as Lydia’s hands continued their exploration, tracing the contours of his painfully erect member with a practiced precision. A soft gasp escaped Todd’s lips, mingling with the charged atmosphere of the room.

“Does it feel good, Todd?” Lydia’s voice, laced with a hint of seduction, drifted through the darkness.

“Yes,” Todd replied, his voice a breathless whisper. “Your touch… it’s exquisite.”

Lydia’s fingers danced along Todd’s cock, teasing and testing his reactions. She leaned in closer, her lips brushing against his ear as she spoke, her voice sending shivers down his spine.

“Remember, Todd,” Lydia murmured, her voice a velvet caress, “pleasure can be found in unexpected places. Let go of control and surrender to the sensations.”

A wicked grin tugged at Lydia’s lips as she intensified her grip on his cock, her touch becoming more deliberate and fervent. Todd’s breath quickened, his body rising instinctively into her fist’s electric embrace.

“You’re mine to command, Todd,” Lydia whispered, her words stirring a primal hunger within him. “Let the sensations consume you, and I promise you an experience beyond your wildest dreams.”

Todd surrendered himself completely, his mind and body enveloped in the whirlwind of sensations that Lydia orchestrated. With each touch, each stroke, he found himself spiraling deeper into a realm of pleasure he had never before experienced.

As Lydia continued to guide him through a journey of erotic exploration, Todd’s inhibitions melted away. In the depths of the darkness, he discovered new facets of his desires, unearthing hidden passions and cravings that lay dormant within him.

The room echoed with their mingled moans and sighs, the symphony of pleasure reaching its crescendo. Todd felt himself teetering on the edge, his body on the precipice of release.

Lydia, sensing his impending orgasm, eased her touch, drawing out the exquisite torture. “Not yet, Todd,” she teased, her voice dripping with sultry delight. “I want to savor every moment, to prolong your pleasure.”

Todd breathed hard, his need bordering on desperation. “Please,” he begged, his voice thick with desire. “I need to come. I surrender completely.”

Lydia laughed, her strokes becoming more urgent, pushing Todd right to the edge and then backing off, “Not tonight, my love.”

Todd’s chest rose and fell with each ragged breath, his senses still humming. In the darkness, Lydia leaned in, pressing her lips against Todd’s, a gentle kiss that held a promise of more to come. “This is just the beginning, Todd,” she whispered against his mouth. “There’s so much more to explore, to embrace within the realm of our desires.”

Lydia, true to her unpredictable nature, slipped away into the darkness before Mrs. Mendelson’s return. Todd lay there, his cock still hard from their encounter, a mixture of frustration and lust filling his thoughts.

Minutes turned into an hour, and still, Mrs. Mendelson had not returned. Todd’s mind wandered, contemplating the possibilities that awaited him once she arrived. The room remained shrouded in silence, broken only by the soft sounds of Todd’s breathing.

Finally, the door to Mrs. Mendelson’s chamber creaked open, and she stepped inside turning on the light. Her eyes, filled with concern and curiosity, fell upon Todd, still bound to the bed.

“Mrs. Mendelson,” Todd said, his voice a mix of relief and anticipation as he squinted into the suddenly bright room, “you’ve returned.”

Mrs. Mendelson’s gaze lingered on him, taking in the sight of his restrained form. Her expression softened, a mixture of understanding and concern flickering across her face.