Keyholder Club
Copyright© 2026 by SindeeM
Chapter 2
BDSM Sex Story: Chapter 2 - Introduction Notes This is the first story in a collection about a group called the keyholder Club. It starts out primarily as mild Femdom BDSM them but could grow to include heavier BDSM CBT and other similar topics. It may include make DOM/slave topics as well. I would like feedback before continuing with the stories. Thank you for reading.
Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa Consensual Reluctant Heterosexual Fiction BDSM DomSub FemaleDom Humiliation Light Bond Rough Sadistic Spanking Analingus Oral Sex
The Keyholder club had a rotating team of people that reviewed applications from people that wanted to join as “Cages” or those that would be wearing chastity devices and then giving the key to one or Keyholders. They had strict rules for who they selected to interview. There were people that just did not provide enough information and were summarily rejected. They were generally looking for people that had a long term interest in Female Domination as submissives including chastity.
Martha Johnson was leader of the selection committee at this time. With her was her daughter Ashley Johnson Giordano and her sister Susan Murphy. Martha is a 60 year old white female that at first glance people would call a Bimbo. She has large, full lips, bleached blonde almost white hair. She has huge tits that strained against whatever fabric dared to contain them, an extra-large ass that commanded attention, wide hips, hourglass figure. She generally has darker makeup that accentuated her predatory gaze. As the saying goes it is not good to stereotype because Martha is exceptionally intelligent.
Her daughter Ashley is a 25 year old white female. She is tall, around 5 feet 10 inches tall. She has pale white skin that flushed pink when aroused, A cup breasts with small but perpetually perky nipples that hardened at the slightest thought of domination. She is skinny, with no hips, but a round ass that provided a perfect handhold for guiding her subs.
They were reviewing applications as Jade Wong walked in wearing an uncustomary conservative outfit of a white blouse and grey office slacks, and medium height black heels. Jade is Chinese, single, 21 year old female. She was born in China and immigrated to the U.S. at the age of 5 with her parents. She has long, straight black hair that fell like a silk curtain, skinny, she is flat chested with A cup breasts with brown areola and long nipples when aroused, she has a flat tight ass that was perfect for pressing against a bound sub’s face.
Martha looked up. Chuckling she said: “Oh my! Jade looks so innocent and conservative! Who would ever know you are such a hard core bitch Jade”
Jade grinned as she sat down, crossing her legs slowly to draw attention to her slender thighs. “One of my cages will be on domestic duty later. I have never let him see me naked even when licking my pussy. The fully clothed ‘normal’ girl look drives him insane. I love seeing the frustration on his face! You have to teach these betas that their only purpose is to serve us. Our needs and our pleasure are what gives them pleasure. You have to be strict and they will learn.”
Martha nodded, her fingers tapping deliberately against the tabletop. “I heard what you did to that poor Cage Tim. Giving him an extra week in chastity when it has already been 3 months before his first release.”
Jade shook her hair out of her eyes, her expression hardening with the memory. “He deserved it. He was not focused on his domestic chores. His dusting and vacuuming was terrible. He was too focused on how much he wanted a release and should have been concentrating on my needs which at that time was cleaning my house.”
Jennifer Wu then replied. Jennifer is 28 year old Chinese American. Born in the U.S. to Chinese parents. Jennifer is what many people would call a BBW. She has big tits that spilled generously from her bra, a large ass that jiggled deliciously when she walked, an hourglass figure that made subs weak with desire. She has a very mesmerizing voice that seemed to enchant some of her Cages.
“Well maybe he could not concentrate on his chores with you sitting half naked on the couch watching him.”
Jade thought for a moment, her lips curling into a predatory smile. “That is exactly my point about focusing on my needs rather than his own. My needs at that time was I wanted my house cleaned. Doing that well pleases me. His purpose is to please me.” She then smiled and laughed. “And of course he knows how much his suffering makes me so fucking wet! He knows that if I’m in the mood he gets some of my personal time for edging, punishment or whatever I deem fit.”
She continued: “Later I chained him to the bed in one my playrooms. I took his useless dicklet out of the chastity cage for some fun denial. I’ve taught him that he thanks me for everything I do. The little slut didn’t thank me for allowing him to have an erection. Although with that tiny useless dicklet I’m not sure that qualifies as an erection.”
Susan Murphy is Martha’s sister. At outward appearances she is the quintessential housewife. She is 50 years old, large tits with a natural sag, normal hips and slight hourglass waist, no thunder thighs, or saddle bags, a medium size ass. She has short, messy bobcut hairstyle similar to Helen Parr from the animated movies.
Susan joined in “He is still very young, and you know what they say, young dumb and full of cum. Maybe you should give him one of your specials. Those oh so unfulfilling prostate milkings to help relieve the pressure.”
Jade responded “What and reward him for being selfish with no self-control? Well after some encouragement he understood his mistake and thanked me for only giving him an extra week in chastity.”
Ashley laughed “Yeah right, your encouragement was probably some Cock and Ball Torture or ass caning, right Jade?”
Jade got an evil grin on her face “Well that type of encouragement is very effective. Yes it was CBT. At the end he was crying from the pain in his balls and from the realization that he disappointed me. He learned a valuable lesson.”
Ashley had an affinity for CBT. “Well tell us Jade about your CBT encouragement, I always like to learn.”
Jade smiled “Of course Ashley I would be happy to tell you all about it. “The true beauty of CBT lies in the paradox which is that the intense pain becomes indistinguishable from pleasure, the line between punishment and reward blurs until complete surrender is inevitable. By the time I finished with the ice and heat play, alternating between sensations, Tim had reached that sublime state of acceptance where his suffering became my pleasure, and through that transfer, his own.”
CBT For Timothy
Jade’s voice cut through the sterile quiet of her playroom. “On the bed, Tim. Now. Face up.”
Tim scrambled to obey, his movements clumsy with a mixture of fear and desperate anticipation. The polished metal of the bed frame was cold against his back as he settled into the center. He watched, his breath held tight in his chest, as Jade retrieved the heavy leather cuffs from the mahogany cabinet. Her movements were economical, precise. She wasn’t rushing; this was a ritual she knew by heart.
First, his wrists. She buckled the thick leather around them, the straps snug but not cutting off circulation. A heavy click echoed in the room as she attached the D-rings to the posts at the head of the bed, pulling his arms taut above his head. His biceps strained slightly. Next came the ankle cuffs, spreading his legs wide and securing them to the footboard posts. He was completely exposed, his body forming a tight X on the black satin sheets. His chastity cage, a small, clear plastic device, seemed to mock him, a constant reminder of his failure and his confinement.
Jade stepped back, her hands on her hips, a silent appraisal that made Tim’s skin prickle. She was still fully dressed in her conservative office attire, the white blouse and grey slacks a stark contrast to his naked vulnerability. It was a deliberate choice, and it worked perfectly. He felt like an object, a specimen being examined.
“Three months,” she said, her voice low and even. “Three months since that pathetic dicklet of yours has been allowed to get hard. And what do you do with that time? You waste it. My house was a disgrace. Dust on the shelves. Crumbs on the floor. You were too busy thinking about your own selfish little dicklet to focus on your one purpose: pleasing me.”
She moved to the side of the bed, her gaze fixed on his caged genitals. “So now, we begin your re-education. A lesson in focus.”
She knelt, producing a small, ornate key. The sound of the tiny lock clicking open was deafening in the quiet room. Jade carefully removed the plastic cage, freeing his balls and his flaccid penis for the first time in months. The air felt strange on his bare skin. His dicklet twitched, a traitorous response to the sudden freedom.
“Oh, it wants to play now, does it?” Jade mused, a cruel smile touching her lips. She picked up a small bowl of ice from the nightstand. “Not yet.”
Without warning, she pressed the ice directly against his scrotum. Tim gasped, his back arching off the bed as the intense cold shot through him. His burgeoning erection died instantly, shrinking into a small, shrunken nub. Jade held the ice there until his balls were tight, drawn-up little knots of flesh against his body. She discarded the ice with a clatter into the bowl.
“Much better,” she said, satisfied. “Now we can begin.”
From a drawer, she produced a line of black wooden clothespins, their springs strong and unforgiving. She took the first one, her fingers testing its sharp grip. “This is for the dust on the bookshelf.” Click. She snapped it onto the loose skin of his scrotum. Tim hissed through his teeth, a sharp, biting pain that radiated up into his groin.
“This,” she said, picking up another, “is for the streaks on the kitchen window.” Click. She placed it next to the first one. Tim’s breath hitched, the twin points of pain beginning to merge into a throbbing ache.
She continued, methodically, her voice a cold monotone as she listed his failures. “The crumbs under the sofa cushion.” Click. “The hair in the shower drain.” Click. “The toilet bowl you didn’t scrub properly.” Click.
One by one, she adorned his sac with the pins until a dozen of them formed a painful, black bouquet. Tim was panting now, sweat beading on his forehead. His fingers clenched into fists above his head, his knuckles white. The pain was constant, a deep, throbbing fire that was stealing his breath.
But Jade wasn’t finished. She stood up and retrieved a small, weighted ball with a metal hook. “And this,” she said, her voice dropping to a whisper, “is for having the audacity to think your own pleasure matters.”
She carefully attached the hook to the clothespin cluster. The weight pulled down instantly, and Tim cried out, a raw, strangled sound. The sharp bite of the pins intensified tenfold, a dragging, tearing agony that made his vision swim. His legs pulled uselessly against their restraints.
“Look at me,” Jade commanded.
He forced his eyes open, blinking back tears of pain. She was standing over him, her expression one of intense concentration, her dark eyes fixed on his face. She was watching him, absorbing his suffering, and he could see the faint flush on her cheeks, the subtle parting of her lips.
A faint flush spread across Ashley’s cheeks as she watched Tim’s reactions. Her lips parted slightly, and she leaned forward, her dark eyes glinting as she absorbed every whimper and tremor. One hand rested on her hip, fingers tapping an impatient rhythm against her slacks. His pain was her pleasure.
“Please,” he whimpered, the word torn from his throat. “Miss Jade, please ... I’m sorry.”
She ignored his plea. Instead, she raised her hand and brought it down in a sharp, stinging slap directly on the weighted clothespins. The impact sent a shockwave of agony through him. Tim screamed, a high-pitched sound of pure anguish, his body convulsing against the bonds. The weight swung, sending fresh waves of torment through his abused balls.
“Sorry doesn’t clean my house, Tim,” she said, her voice hard as stone. She slapped him again, and then a third time, each impact punctuated by his desperate cries. “This is what happens when you forget your place. This is what happens when you’re a selfish little bitch.”
Tears were now streaming freely down his temples, mingling with his sweat. He was sobbing openly, the sounds broken and pathetic. The pain was overwhelming, a white-hot fire that consumed everything else. But through the haze of agony, something was shifting. The selfish thoughts, the frustration of his chastity, the resentment of his chores, it was all being burned away, seared out of him by the relentless pain. All that was left was the raw, elemental truth of his position. He had failed. He had disappointed her. This was his consequence.
Jade finally stopped, her chest rising and falling slightly. She looked down at his wrecked, tear-streaked face. “Do you understand your mistake now, Tim?”
He could only nod, his body trembling uncontrollably.
“Good.” She began to carefully, almost gently, remove the clothespins. The rush of blood back into the pinched skin was a new, exquisite agony, far worse than the initial pinch. He sobbed with each one she removed, his body writhing. When the last one was gone, his scrotum was a mottled, angry red, dotted with deep purple marks where the pins had been.
She unhooked the weight and set it aside. Tim lay limp, panting, his body slick with sweat and tears. He felt hollowed out, broken.
As Jade wiped the tears from his face with surprising gentleness, Tim’s body relaxed slightly. The sharp pain in his balls throbbed, but a strange warmth spread through his chest. He found himself leaning into her touch, his breath steadying as he met her eyes. This made him realize how lucky he was to have such a strict but caring Keyholder.
Jade finished describing how she’d made Tim cry and thank her for the extra week in chastity, a satisfied smirk playing on her lips as she remembered his pathetic whimpers.
“The little bitch boy was sobbing like a baby by the time I was done with his balls,” Jade said, taking a sip of her coffee. “But he learned his lesson. I guarantee his dusting will be fucking impeccable next time.”
Ashley shivered with delight, her nipples visibly hardening through her thin tank top. “God, I love that. The way they break so completely when you really torture their useless balls. There’s nothing hotter than watching a grown man cry because you’ve put a dozen clothespins on his sac.”
Susan nodded sagely, adjusting her sensible housewife dress. “Pain is the most effective teacher. That boy won’t forget his place again anytime soon.”
Martha’s massive tits jiggled as she laughed heartily. “Well done, Jade! Now, let’s get back to these applications. We need to find some fresh meat for the club.”
Ashley swiped through her tablet, her eyes glinting with mischief as she found Michael’s profile. “Speaking of fresh meat, I’ve got a perfect candidate here. Fifty-year, looks like he’s well off financially and according to this, his dicklet is practically microscopic.”
Jade leaned in, her dark eyes scanning the screen. “Hmm, not bad, except for that tiny dicklet that is some nice eye candy. And you say he’s never done any kinks before?”
“Virgin territory,” Ashley confirmed, tapping a perfectly manicured nail against the screen. “Completely inexperienced but desperate to serve. The best kind. I’m thinking of interviewing him myself this weekend.”
Martha perked up at this, her massive tits jiggling as she leaned forward. “Ooh, a fresh one! Those are always so much fun to train. Make sure you test his pain threshold properly, dear. And don’t forget to check how tight his little asshole is.”
Ashley’s grin widened. “Oh, I have every intention of giving him the full inspection. Hairless from neck down, internal examination, the works. I want to see how he reacts when I’m squeezing his pathetic little balls and calling him a bitch boy.”
“I want details,” Jade said, already imagining the possibilities. “There’s nothing quite like breaking in a new submissive, especially when they realize they’re nothing but a set of holes for our pleasure...”
Interview With Michael
The email arrived with a soft chime, a stark contrast to the seismic shift it caused in Michael’s world. The subject line was simply: “Keyholder Club - Interview Request.” His heart hammered against his ribs, a frantic drumbeat of anticipation and fear. He had half-expected a polite rejection, a form letter thanking him for his interest. Instead, this.
The email was from Ashley Johnson. It was concise, direct, and utterly professional, which somehow made it even more thrilling. It stated he was being considered for the position of “Cage” and that she would be conducting his personal interview. He was given a choice: their sterile, intimidating facility, or his own home. She recommended his home, explaining that a familiar environment often led to a more honest and revealing conversation. The thought of this woman invading his personal space, sitting on his couch, judging him in his own surroundings, sent a jolt of pure adrenaline through him.
The email laid out the prerequisites with chilling clarity. He was to be completely hairless from the neck down. The instructions were specific: “Pay particular attention to your asshole and balls. These areas must be perfectly smooth.” He would be naked for the majority of the interview. Physical measurements would be taken—not just height and weight, but the precise dimensions of his waist, hips, and, most intimately, the length and girth of his dicklet, both soft and erect, to ensure a custom-fitted chastity device.
They would dissect his sexual history, his preferences, his off-limits activities, his deepest kinks, and his most hidden desires. This was the time, the email stressed, to voice any questions, concerns, or hard limits. It also contained a stark warning: once actively involved as a Cage, Keyholders found it very fulfilling to push a Cage’s limits. The process was designed to test and expand boundaries.
A “Safeword” policy was explained in detail. There were two levels. The first was an immediate stop for a specific activity due to medical issues, breaking hard limits, or legal concerns. The second was more absolute: an immediate halt to all activities, leading to the Cage’s release from the Club. This could be initiated by the Cage if he felt he couldn’t continue, or by the Keyholder if she detected he was unwilling or unable to meet the demands of his new life.
The email then delved into body modifications: tattoos, piercings, branding. He was to consider if he would accept these, and if so, whether they would be on body parts visible in his daily life.
Attached were legal documents: liability releases, confidentiality agreements, and a detailed manifesto of the Club’s philosophy. Michael’s hands trembled as he downloaded them. This was no longer a fantasy. This was a contract.
He read the email again, his pulse racing. The impersonal exchange of photos and data was over. This was real. A face-to-face meeting. He knew, with a certainty that both terrified and exhilarated him, that he would go through with it. Heat bloomed in his chest and spread through his body, a tingling current of pure excitement. Meeting at his house was perfect. He typed a reply, his fingers clumsy on the keyboard, agreeing to the interview for the coming Saturday, five days away.
My God, he thought, a wave of dizziness washing over him. In five days, my life could be irrevocably changed.
He hit send, then immediately began the arduous task of reading and signing the legal documents. Just like with his initial application, he sat before his computer, the cursor blinking over the “Confirm” button. He closed his eyes, took a deep breath, and clicked. CLICK. It was done. His journey had truly begun.
The next few days were a blur of research and preparation. He scoured forums on female domination and chastity, absorbing every detail, every anecdote. The advice on hair removal was a common topic. For his asshole and balls, the consensus was clear: depilatory creams. Razors were too risky on such sensitive, wrinkled skin. For his pubic area, razors were efficient, but creams provided a smoother finish.
Two days before the interview, he made his purchases. New, sharp razors and potent-smelling tubes of depilatory cream. He was fortunate; he had little body hair to begin with, a fine, almost invisible dusting on his chest and none on his back or legs. Still, the instructions were “hairless from the neck down.” He shaved his underarms, then methodically shaved his legs, even though it was unnecessary. The ritual itself was part of the preparation.
Finally, he stood in his bathroom, ready for the main event. He applied the cream to his balls, the chemical smell filling the air. He waited the prescribed time, his heart thudding, then wiped it away with a wet cloth. The skin was left smooth, pink, and utterly bare. He repeated the process with his asshole, bending over in front of the mirror to ensure he got every last hair. The sensation was bizarre, the cool air on his newly exposed, puckered skin feeling alien and intensely vulnerable.
When he was done, he looked at himself in the full-length mirror. He was a different person. Smooth, hairless, almost prepubescent. He ran a hand over his bare balls, then around his tight, hairless asshole. The feeling was odd, a constant, tactile reminder of his submission and the impending interview. He was ready.
Saturday arrived. Ashley had said he would be naked for most of the interview, so the question of what to wear felt absurd. He settled on a pair of loose-fitting shorts and a plain t-shirt, the uniform of a man trying not to try too hard. That morning, he performed another inspection, running his hands over his body, confirming that he was still perfectly, unnaturally smooth. The waiting was over. The doorbell was about to ring.
Ashley Arrives
The doorbell chimed, a sharp, electronic sound that sliced through the silence of Michael’s house. This is it, he thought, his heart suddenly hammering against his ribs like a trapped bird. He took a deep, steadying breath, smoothed down his shirt, and walked to the door. His hand trembled slightly as he grasped the cool metal knob.
He opened the door and his breath caught in his throat. Standing on his porch was a young woman who seemed to have been plucked from his deepest fantasies and his most intimidating nightmares. She was tall and slim, with a cascade of platinum blonde hair cut in a sharp, deliberate bob that framed a face of striking, almost severe beauty. She wore no makeup or lipstick, yet her features were captivating—high cheekbones, full lips, and piercing blue eyes that seemed to see directly through him.
His gaze traveled down. She wore a thin, white tank top that clung to her torso, revealing the unmistakable shape of small, perfect breasts. It was obvious, painfully obvious, that she wasn’t wearing a bra. Her nipples were hard, two distinct points pressing against the fabric, a silent, aggressive statement of confidence and control. Her lower half was encased in tight, worn-looking jeans that hugged her narrow hips and long legs, ending in a pair of simple white sneakers. She looked to be in her mid-twenties, but she carried herself with an authority that belied her age.
He realized he was staring, his mouth slightly agape. He gathered himself, his voice coming out as a croak. “Hello?”
“Michael?” she asked, her voice clear and direct. She didn’t wait for an answer, stepping past him into the foyer as if she already owned the place. “I’m Ashley.”
He closed the door, the click of the latch sounding unnaturally loud in the sudden quiet. “Thank you for coming, um ... well, um ... is it proper to call you Ashley?” he stammered, feeling like a schoolboy in her presence.
A slow smile spread across her lips, but it didn’t quite reach her eyes. “Of course, for now. If that puts you at ease. However, I prefer that you address me as Miss Ashley, since we will be getting into the details of our club and your place there.” The emphasis on “your place” was subtle but unmistakable.
“Of course, Miss Ashley,” he said quickly. “I will do as you prefer.”
She immediately took charge, her eyes scanning his living room with a critical, assessing gaze. This was his house, his space, but he suddenly felt like an intruder. She didn’t wait to be shown where to sit, choosing the single armchair that positioned her slightly above him as he nervously sat on the edge of the couch. She crossed her legs, the movement fluid and deliberate, drawing his eyes to the curve of her thigh.
“First, I and the ladies of the Keyholder Club thank you for your interest in joining,” she began, her tone all business. “I am here to help determine the boundaries and limits that we both will need to put in place to make this an enjoyable experience.” She let out a short, sharp snicker. “Well, perhaps not so enjoyable for you at times!”
She leaned forward slightly, the tank top pulling tighter across her chest. His eyes were drawn to her erect nipples again, a magnetic pull he couldn’t resist. She wore these clothes for exactly that reason, he realized. To distract him, to test him, to remind him that she was in control of his desires before they had even begun.
“So, let’s start with you telling me what interests you in this subject matter and why you want to join.”
Michael cleared his throat, the sound loud and awkward in the quiet room. It was profoundly disconcerting to be baring his most intimate secrets to this young, intimidatingly beautiful woman. He described how he always had a secret, a “dark desire” for non-vanilla sexual experiences. He spoke of his conservative upbringing, his family’s prominent position in the community, the weight of expectation to be a strong, conservative leader. He carefully avoided details about his late wife, mentioning only that their sex life had been passionate but “normal.”
As he spoke, Ashley’s expression remained unreadable. She watched him, her blue eyes unblinking, absorbing his every word, his every nervous gesture. He found himself confessing things he’d never told anyone: his powerful leadership role at his financial firm, the stark contrast with the submissive side that excited him, the way he’d explored various submissive roles until he found the one that resonated most deeply: orgasm denial and chastity.
“It’s the lack of control,” he admitted, his voice dropping. “Or, more precisely, the giving up of control. Watching videos, reading stories of men locked up ... the idea that someone else would own that part of me, dictate when I can feel pleasure ... it resonates with a part of me I didn’t know existed.” He explained his reluctance to pay for a professional Domme, his disinterest in self-bondage. “Then I found the Keyholder Club. It seemed ... real. A community. A way to truly explore this, not just as a fantasy.”
He was honest, telling her he had no real-world experience. “So really,” he finished, “it’s my desire to explore chastity, to give up control, along with some other ... darker interests that I assume would be included.”
Ashley nodded slowly as he finished speaking. “Very good, Michael. I understand what you said, and I am pretty sure we can find an arrangement that will work out well for you. You have the right perspective on what you want and why.” She paused, letting her words sink in. “But an important point is that this is not just jerk-off material for you. This is not a game. There is a commitment from a time perspective, as well as physical and emotional commitments. You will understand that as you actively get involved.”
Michael felt a wave of relief wash over him.
“First,” she continued, her tone becoming more formal, “I will very likely not be your primary Keyholder. You do not get to pick your Keyholder; she will pick you. That is why it is important to make sure we align on your expectations and ours.”
She leaned forward, her gaze intensifying. “You are now giving up control of your sexual experiences to your Keyholder. She owns your dicklet and your balls. She controls when you are allowed an erection and if you are allowed a release. What we call a ‘release’ is when you ejaculate, are given a ruined orgasm, or are given something like a prostate milking. You are a beta male. An Alpha male would never let someone lock up his cock in a chastity cage. Terms are important. An Alpha Male has a cock. You, as a beta male, have a dick or dicklet.”
She looked directly at him, her eyes pinning him in place. “Do you understand that part?”
“Yes, Miss Ashley,” he said, his voice firm. “I understand that I am a beta male and that I would not own my own dicklet and balls. My keyholder owns those.”
Ashley smiled, a thin, predatory curve of her lips. “And...?”
Michael looked perplexed for a moment. “Well, um ... that my Keyholder determines if I can get an erection and if I am allowed to ejaculate.”
He wondered how the act of cumming, something so primal and personal, could be turned into something so clinical as “ejaculate.” The word itself felt sterile, devoid of passion, a simple bodily function to be permitted or denied at another’s whim.