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His Best Friend's Mom Becomes His Keyholder Part 1

"His Best Friend's Mom Catches Him Stealing Her Panties And Becomes His Keyholder"

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Author's Notes

"His Best Friend's Mom Catches Him Stealing Her Panties So She Becomes His Keyholder"

The summer sun cast a golden hue over the suburban neighbourhood, its neatly trimmed lawns and well-maintained houses basking in the light. The air was filled with the scent of freshly cut grass and blooming flowers, a perfect day for a visit to his best friend's house.

Nineteen-year-old Alex walked briskly towards Jake’s home, his thoughts preoccupied with their upcoming gaming session. Friends since childhood, Alex and Jake had a bond strengthened by countless shared adventures and secrets. Yet recently, Alex's thoughts drifted towards someone else entirely — Jake's mother, Lisa.

Lisa was a striking woman in her early forties, with long, flowing blonde hair, piercing blue eyes, and a figure that turned heads wherever she went. She was kind and caring, often treating Alex like one of her own. But Alex's admiration for her had grown into something more intense, something he struggled to control. He was captivated by her presence, his eyes lingering on her more than they should.

His infatuation with Lisa had nearly gotten him in trouble. Several times he house-sitted for their family while they were on vacation, he went through her underwear drawer and even stole several of her panties and lingerie from their bathroom linen baskets.

He spent countless nights masturbating to them, imagining her wearing them as her mature hands guided him with experienced, sensual movements. His mind was constantly consumed by the image of her, unable to escape the intoxicating allure of her beauty.

That day, as he walked up the driveway, Alex felt a familiar flutter in his chest. He knew Lisa would be home and the mere thought of seeing her made his heart race. He knocked on the door, and moments later, it swung open to reveal Lisa, dressed in a casual yet alluring outfit — a low-cut tank top and shorts that accentuated her curves.

"Hi Alex, come on in," Lisa greeted him warmly, her smile sending a shiver down his spine.

Lisa had noticed Alex's lingering gazes over the past few months. Her husband's frequent business trips left her with unmet needs, and Alex's youthful admiration and desire didn't go unnoticed. She found herself increasingly drawn to his attention, the way his eyes followed her movements, his nervousness around her palpable. She was about to put in place a plan she had been planning for months.

"Hey, Mrs. Johnson," Alex replied, stepping inside. He tried to keep his eyes from wandering, but it was futile. He couldn't help but steal glances at her cleavage, the soft swell of her breasts barely contained by the tank top.

“Jake is just picking up some snacks at the grocery store for your gaming session. He will be back shortly," she said, her eyes catching Alex's for a moment longer than usual.

“You look thirsty. Want something to drink?"

"Sure, that'd be great," Alex said, grateful for the distraction.

As Lisa walked to the kitchen, Alex followed, his eyes once again drawn to her shapely figure. She reached up to grab a glass from the cupboard, her top lifting slightly and revealing a hint of her toned stomach. Alex swallowed hard, his mouth dry, as he tried to avert his gaze.

"You seem a little off today, Alex," Lisa said, turning to him with a knowing smile. "Everything okay?"

"Yeah, just... thinking about stuff," Alex mumbled, feeling his cheeks burn with embarrassment as he just masturbated to Lisa’s lingerie in his room only thirty minutes ago.

Lisa handed him the glass of water, her fingers brushing against his. "You know you can talk to me about anything, right?"

Alex nodded, his heart pounding in his chest. "Thanks, Mrs. Johnson."

Alex managed a weak smile and took a sip of water, hoping to steady his nerves. He was about to excuse himself and head upstairs when Lisa's voice stopped him.

“I think it was time we talked about what you’ve been getting up to while house-sitting for my family, Alex..."

He froze, catching her gaze fixed on him with an intensity that sent a jolt of fear and excitement through him. “Eh, I am not sure what you mean?"

"I couldn't help but notice… several of my panties and lingerie go missing every time you house-sit for my family. I installed cameras, and well…look at this..." Her voice was casual, but her eyes gleamed with a provocative challenge as she used a remote to turn on the television in the kitchen.

Alex watched in horror as he saw a video of himself going through Lisa's panty drawer in her bedroom, carefully placing her used panties and lingerie into his backpack.

His heart skipped a beat. "I-I wasn't... I mean, I didn't mean to..."

Lisa stepped closer, her voice dropping to a sensual whisper. "It's okay, Alex. But if you don't want Jake and everyone else to find out about your little... interest, you'll have to do a few things for me as payback..."

Alex's mind raced, panic mingling with a strange thrill. “Yes, Mrs. Johnson. What do you want me to do?"

A playful smile tugged at Lisa's lips. “I think it’s time we took care of your nasty little habit, and you took on a few more... personal duties."

Alex felt a surge of both fear and arousal. The idea of exposure was terrifying, yet the way Lisa looked at him stirred something forbidden within him. He searched her eyes for mercy but found only determination.

"Do we have a deal?" Lisa asked, her voice steady and commanding.

Alex swallowed hard, his shoulders slumping in reluctant agreement. “Yes, Mrs. Johnson."

Lisa stepped even closer, her body almost brushing against his. The proximity sent a shiver of anticipation down Alex's spine as he felt the heat radiating from her. She reached up, brushing a lock of hair from his forehead with delicate fingers, her touch electric against his skin.

"I think you need to be properly disciplined," Lisa murmured, her voice low and husky. She leaned in, her lips grazing his earlobe. "And I think I know just how to do it."

Alex's breath hitched as her words sent a surge of desire straight to his groin. He could feel her arousal, a heady mix of power and pleasure that fueled his own growing need. Without another word, she took his hand and led him out of the kitchen, towards her bedroom.

"Good boy," she purred, her smile widening seductively. "Follow me."

She led him silently to her bedroom, the air thick with unspoken tension. Locking the door behind them, she turned to face him.

"Now," she said softly, her voice a sensual command. "Strip for me."

Alex blinked in surprise, his pulse racing. "Sorry, what?"

"You heard me," Lisa replied, her tone firm yet inviting. "Take off your clothes, Alex. Show me what you're willing to do to keep our little secret safe."

Alex hesitated, torn between shame and a growing desire to obey her. Slowly, he began to undress under her watchful gaze, his body betraying his nervous excitement.

Lisa chuckled softly, her eyes lingering on his every move. "My, my... flattered, aren't we?"

Alex blushed deeply, his nakedness feeling both vulnerable and thrilling in front of her as his member stood to full attention.

"Now kneel, Alex," she commanded.

Without hesitation, Alex obeyed, sinking to his knees before her.

Lisa grabbed a pair of black fluffy handcuffs from her bedside and swiftly cuffed Alex's hands behind his back. His heart raced as she opened a drawer and withdrew a sleek, metal device — a steel male chastity cage. She explained its mechanics in a clinical, almost detached manner. Alex could hardly believe this was happening.

Speechless and naked in Lisa's bedroom, Alex's arousal was palpable.

She seized his balls firmly, her nails digging into his sensitive flesh.

Alex gasped, on the verge of crying out, but before he could make a sound, Lisa silenced him by gently putting a pair of her panties in his mouth.

Shock and pain flooded through Alex, causing his erection to wane as Lisa deftly secured the metal device around his penis and balls, ensuring a snug fit that left no room for escape.

With a decisive click that resonated in the silent room, Lisa locked the chastity device in place. Holding the key up, she dangled it teasingly in front of him. "Remember, this stays with me. Behave, and maybe I'll grant you release from time to time."

She hung the key on a necklace around her neck and then took out her phone, capturing several provocative images of Alex kneeling in her bedroom, clad only in the steel chastity belt, with his hands restrained behind his back.

"Let's hope these photos never need to reach your parents," she teased with a knowing smile.

Alex nodded, a cocktail of shame and thrilling exhilaration swirling within him. Despite his embarrassment, he couldn't deny the rush of submission and arousal that Lisa's dominance ignited in him.

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Just then, they heard a car pull into the driveway — Jake was home.

Lisa motioned for Alex to be quiet and removed the panties from his mouth. She then removed the handcuffs and quietly instructed him to put his clothes back on and play with Jake.

Alex did as commanded, his mind racing with the intensity of what had just transpired. As he left her room, he bumped into Jake on the stairs, who raised an eyebrow at him.

"Everything okay?" Jake asked, a hint of suspicion in his voice.

"Yeah, all good," Alex replied quickly, trying to hide his inner turmoil.

“Hey, Dude! I got us some snacks!” Jake said excitedly for their gaming session.

“Huh, oh yeah. That sounds awesome," Alex tried to respond.

Alex and Jake sat down in the living room and began gaming. Alex lost every game poorly, which Jake noticed.

“Either I've gotten better, or you’re distracted today,” Jake said, casting a suspicious glance at his friend.

Alex was still in shock and trying to process what had just happened. Fifteen minutes ago, he had been naked in Jake’s mom’s bedroom, where she cuffed him and locked him in a chastity belt.

After another hour of Jake winning games, Lisa came into the room carrying some drinks for the boys. Her breasts were on full display in her tank top, and the key to the chastity belt was nestled snugly within her cleavage, teasing Alex with every movement.

Alex immediately began to grow hard but felt the sharp pain of the device holding his throbbing member in check.

“Thanks!” Jake replied eagerly, reaching for his drink.

“Wow, thanks, Mrs. Johnson,” Alex replied, his voice a mix of gratitude and suppressed desire.

She just winked at Alex and said, “Thanks again for agreeing to mow our lawn today, Alex. You’re a lifesaver!” Her tone was bright and cheerful, but the glint in her eyes hinted at the underlying tension between them.

Alex made his way outside, the weight of the chastity device serving as a constant reminder of his new reality. He couldn't help but wonder how his life had taken such a turn. Glancing back at the house, he caught sight of Lisa watching him from the window, a satisfied smile playing on her lips. Her gaze held a promise of more to come, and the sight of her sent a fresh wave of arousal and frustration through him.

As he mowed the lawn, the vibrations from the machine only heightened his sensitivity, each jolt a cruel reminder of his predicament. The warm sun did nothing to alleviate the heat pooling in his groin, the chastity belt a constant, maddening presence.

"Dude, why are you doing chores around my house?" Jake asked, raising an eyebrow as he watched Alex mowing the lawn.

Alex shrugged casually, his heart racing with the fear of exposure. “If I don’t get into college, I might look to do home improvements. I was telling your mom, and she said she would help me get work experience around your property," he replied, hoping his voice sounded convincing.

Jake gave him a sceptical look but didn't press further. However, Alex knew he needed to be more careful. He couldn't risk Jake suspecting anything unusual between him and Lisa.

When he finished the grass, Lisa came out to inspect his work. She immediately began pointing out tiny blades of grass missed here and there, her eyes twinkling with amusement.

“I guess you need more motivation to do a better job on our lawn. I’m sure another week or two in chastity will have you doing a much better job,” Lisa teased, her voice dripping with playful menace.

Alex blushed a deep red, unable to muster any response. The combination of embarrassment and arousal left him speechless.

“Thanks again, Alex. I will see you later,” she said, her eyes lingering on him.

Just before he left, Lisa surprised him with a big hug, pressing her body against his. The sensation of her breasts against his chest sent a wave of arousal through him. He felt the key to his penis’ prison dangling against him, a tantalizing reminder of his predicament.

"Thanks for all the help today, Alex. You should think about what you’re going to wear to the Halloween party at the end of the month," she said with a mischievous wink and a smile that ignited a fire within him.

Later that night, alone in his room, Alex replayed their interactions in his mind. His hand slipped beneath the fabric of his pants, caressing the steel chastity device that held his arousal captive. He couldn't masturbate or find release, the frustration heightening his need.

Alex spent the next few days in absolute torment. His every thought was fixated on the steel chastity belt locked around his penis. The relentless arousal was maddening. He couldn’t stop thinking about Mrs. Johnson, his mind racing with fantasies that left him more frustrated than ever. He had never been so horny in his life, and the inability to do anything about it only heightened his desperation.

Finally, Alex thought he had an opening to see Mrs. Johnson again. He and Jake planned to see a new movie about two lovers who were secret agents, and Mrs. Johnson had agreed to drive them home afterwards.

"If I can just get a few minutes alone with her, I might be able to get this thing off!” Alex thought, hope mingling with his desire.

It was just Alex’s luck that the movie included a scene where the female agent was dressed as a dominatrix in black latex, engaging in a kinky scene with a bad guy. The erotic display was too much for him.

“Wow, I wouldn’t mind dating someone like that,” Jake whispered to Alex as the scene played out.

"Tell me about it…” Alex replied, his dick getting crushed by the steel chastity belt as he got turned on, the pressure almost unbearable.

After the movie, they stepped outside. Once their eyes adjusted to the sun, Alex's breath caught in his throat. Mrs. Johnson stood there, looking incredible in a low-cut black top with a white garment that accentuated her sleeves. Nestled between her perky, firm breasts was the necklace with the key to Alex’s prison, swaying slightly as she moved.

His heart pounded in his chest, a mix of arousal and desperation flooding his senses. He knew he had to find a way to be alone with her, to plead for release. The sight of her, the key dangling provocatively, was almost too much to bear.

"Let’s grab a coffee before we head home!" Lisa said energetically, her voice carrying a hint of playful anticipation as she led the way to a nearby coffee shop.

Alex’s eyes were glued to her swaying thick ass the whole walk there, a magnetic allure he couldn’t resist.

Inside the café, Lisa nestled herself comfortably between Alex and Jake at a corner table. The afternoon sun cast a warm glow around them, adding a sultry ambience to the scene. Alex's gaze kept returning to the small, tantalizing chastity key nestled between her breasts, a reminder of their private game.

“So tell me about the movie,” Mrs. Johnson chuckled, taking a sip of her iced tea, clearly aware of Alex’s predicament and enjoying his discomfort.

Lisa couldn’t resist a mischievous grin, her eyes sparkling with playful mischief as she glanced at the key pendant. She shifted subtly in her seat, her leg brushing against Alex's under the table. The touch was electric, and she felt the slight bulge of the chastity belt he was wearing—a punishment for stealing her panties.

"So, Alex," Lisa interjected, her voice a teasing purr, “What was your favourite part of the movie?"

Alex blushed, feeling her foot against his chastity belt as she spoke. "Oh, you know, just the action and that...."

“Ha, yeah right!” Jake sniggered. “There was a scene where the female agent was dressed as a dominatrix, and Alex could barely take his eyes off her!” he laughed.

“Oh? I might have to give it a watch,” Lisa replied, suppressing a laugh with a mischievous grin. Her arched eyebrows raised in feigned innocence, her eyes alight with interest.

The drive home was torturous for Alex. Lisa, now in the driver’s seat, positioned the middle mirror so he had a perfect view of the key nestled provocatively between her breasts. His arousal grew with every glance, the chastity belt a constant, frustrating reminder of his desire.

Lisa dropped Alex off outside his home, their interaction still laden with unspoken tension. He hadn’t had a chance to speak to her in private, his need for release growing by the minute.

“It was great seeing you, Alex. We’ll see you at the Halloween party next weekend!” Lisa said, her excitement palpable, her eyes promising more teasing delights to come.

Published 
Written by FemaleLedRelationships
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