Master Jonathan

A story of meeting Master Jonathan for the first time. A story of bondage, leather, submission, master.

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  • 21 Min Read

As I closed the door behind me, the sound of the latch echoed in the quiet room. My hands trembled slightly as I locked it. The letter lay on the table in front of me, its words neatly handwritten and precise. The instructions were clear, almost ritualistic, and I knew there was no turning back now. This was what I had agreed to.

The first task was simple enough: I stripped down, neatly folding my clothes and placing them to one side. I felt the air brush against my skin, the vulnerability of standing there alone intensifying with each passing moment. On the table lay the items he had prepared: a leather hood, a collar, a gag, a blindfold, handcuffs, and two small but solid padlocks.

I reached for the hood first. Pulling it over my head, I adjusted it until it sat snugly in place. The fabric was thick, muting the sound of my breathing and my own thoughts. Next, I picked up the collar. My fingers fumbled with the padlock, but eventually, I snapped it shut, the collar pulling on my neck.

The gag came next. It was smooth, rubbery, and unmistakable in its purpose. I placed it in my mouth and secured it tightly. A small thrill of apprehension coursed through me as I felt its unyielding presence. My breathing became more controlled, slower, as I adjusted to its constriction.

I paused before the blindfold, re-reading the warning in the letter. Though I couldn't see anyone else in the room, the words felt like they were spoken directly to me. Finally, I fastened the blindfold around my eyes, plunging myself into darkness. Every other sense became sharper—the faint creak of the floorboards under my weight, the coolness of the room, the faint metal tang from the collar.

The last instruction was the most daunting. With my sight and speech taken from me, I reached behind my back, fumbling until I locked my wrists together with the handcuffs. My knees hit the floor harder than I anticipated, and I knelt there, still and exposed, waiting.

The letter had been clear: "I will come for you when I am ready." Those words repeated in my mind like a mantra. Time began to stretch and blur. Was it minutes? Hours? Each second felt endless, my body tingling with anticipation and vulnerability.

It was at Pride, in the chaos of celebration, that I first saw him. The sun was setting, the air buzzing with music, laughter, and the distant hum of conversations, but everything around me seemed to fade the moment he came into view. He was tall, commanding, and impossibly self-assured, dressed head-to-toe in leather that clung to him like a second skin. His outfit stood out even in the colorful sea of expression around us—black leather trousers, gloves, a cap, and a vest that barely covered his chest. It was bold, unapologetic, and completely magnetic.

I was a couple of beers in, the edges of my nerves softened by the alcohol, and I couldn’t take my eyes off him. He carried himself with a confidence that was almost unnerving. Most people at Pride were there to celebrate, to party, to express themselves freely, but he wasn’t just expressing himself. He owned the space around him, and everyone else seemed to instinctively sense it, giving him a wide berth even as their eyes lingered. Mine lingered too.

I tried to be discreet, glancing at him from the corner of my eye, but it was impossible to be subtle. He noticed. Of course, he noticed. His gaze locked onto mine across the crowd, and my stomach did a strange little flip. It wasn’t just that he was attractive—he was—but there was something about the way he looked at me. Intense. Focused. As if he already knew exactly what I was thinking and what I wanted, even though I wasn’t sure of it myself.

And then, as if it were the most natural thing in the world, he started walking toward me. My heart raced, and I suddenly felt very aware of how average I must have looked in comparison—just another guy at Pride with a beer in hand and a cheap tank top. Yet his eyes never wavered as he closed the distance between us, a slight smirk on his lips.

When he finally reached me, he didn’t bother with small talk. No introduction, no pleasantries. He looked me up and down, his smirk widening slightly. “Have you ever submitted to a master before?” he asked, his voice low and steady, cutting through the noise around us.

I blinked, caught off guard. My first instinct was to laugh—it was such a bizarre, bold thing to ask someone you’ve just met. “What, like right here at Pride?” I said, grinning, trying to brush it off as some kind of joke. “That’s a hell of a pick-up line.”

But he didn’t laugh. He didn’t even smile. His expression stayed exactly the same, calm and confident, like he had all the time in the world and no doubt that I’d take him seriously. “I’m not joking,” he said simply.

There was something about his tone, about the sheer audacity of him, that made me falter. He wasn’t drunk, but his presence alone made me feel tipsy. “Well, I mean…” I stammered, unsure of what to say. I tried to lean into the moment, matching his intensity with a cheeky grin. “Maybe I could give it a try?”

His eyes narrowed slightly, and he tilted his head, studying me. “You’ve been drinking,” he said, his voice firm, almost scolding. “I would never take a slave who wasn’t in full control of himself. Submission requires clarity. You don’t have it right now.”

The way he said it—so matter-of-fact, so sure of himself—made me feel small in the best and worst ways. For the first time, I realized that this wasn’t just a game to him. He was serious. Deadly serious.

Before I could respond, he held out his hand. “Your phone,” he said.

I hesitated for a moment, confused, but the way he looked at me left no room for argument. I fumbled in my pocket, pulling out my phone and handing it to him. He took it without a word, his gloved fingers moving quickly over the screen. When he handed it back, I saw that he had entered a new contact: Master Jonathan.

“When you’re sober,” he said, locking eyes with me again, “and when you’re ready to submit properly, you’ll text me.” He leaned in slightly, his voice dropping just enough to send a shiver down my spine. “And when you do, be sure you’re ready to give me everything.” He grabbed my dick. 

With that, he turned and walked away, leaving me standing there, phone in hand, heart racing, and erect. It wasn’t until much later, when I was home alone, staring at his name in my contacts, that I realized he had planted a seed in me that I wouldn’t be able to ignore.

Back in his house, it remained quiet and I strained to listen for any sign of him. Then I heard it: the creak of a floorboard, distant but distinct. My breath hitched as the sound grew closer, each step deliberate and measured. The unmistakable creak of leather boots followed, the sound sharp and commanding, matching perfectly with the man I’d envisioned. I held my breath as he descended the stairs, his movements unhurried, purposeful. There was a faint tapping noise as well, rhythmic and deliberate, like the sound of something hitting the bannister—the riding crop, I realized. He was carrying it, just like in his profile picture. My heart pounded harder.

I couldn’t see him, but in my mind, I could picture him perfectly: the tight leather vest hugging his chest, the gleam of his gloves as he gripped the crop, the polished boots that seemed to echo authority with every step. My imagination painted the scene vividly, filling in every detail as the sounds grew louder, closer. The air around me seemed to change, growing heavier as his presence filled the space. His breathing was faint at first, almost imperceptible, but as he neared, it became clearer, more pronounced. I could feel the energy radiating from him, an aura of dominance that made my skin prickle.

He didn’t speak as he approached. The silence was more powerful than any words could have been. My body tensed as I felt him circle me, the soft creak of leather boots moving slowly around where I knelt. I could hear the faint rustle of his clothing, the brush of gloved fingers trailing along the banister or tapping the riding crop against his palm. My heart was racing now, my breath shallow and quick. I was shaking—not out of fear, but out of a potent cocktail of excitement, arousal, and the overwhelming need to please him.

I wanted so badly to see him, to lift the blindfold and confirm that the man I had imagined matched the one standing before me. I wanted to feel his hands on me, to hear his voice, to be touched, claimed. But instead, all I had were the sounds: his boots against the floor, the creak of leather, the quiet, deliberate pace of his movements. He paused behind me, so close I could feel the heat of his presence. His breathing was steady, controlled, just inches from me. My body ached for him to touch me, to claim me in some way, to validate the trust I had placed in him by coming here, by kneeling like this, exposed and ready.

And then he moved away. The sound of his boots faded slightly, his presence retreating. I clenched my fists, frustration and longing surging through me. I wanted to cry out, to beg him to come back, to touch me, to do something, anything. The denial was sharp, cutting through the haze of excitement. He was testing me, I realized. He was setting the tone, showing me that this was his game, his control.

I bit down hard on the gag, struggling to keep myself composed. He hadn’t even touched me, and yet I was trembling, aching for more, desperate to feel his dominance in more than just sound and presence. The waiting was excruciating, and I hated it, but I also craved it. This was what I had come here for, and he knew exactly what he was doing.

The moments dragged on, each second stretching into eternity as I knelt there, sweating, trembling, and straining to hear every little sound. My body felt like a live wire, every nerve ending on high alert, aching for something—anything—to happen. I was excited beyond words, yet the tension was agonizing. He was keeping me right where he wanted me, balanced on the knife’s edge between anticipation and desperation.

I heard his boots creak again, the sound subtle but deliberate, signaling his movement. My heart leaped as the noise drew closer, each step measured, purposeful. He stopped just in front of me, and I felt his hand on the gag. Slowly, he unfastened it, the cool air brushing my face as he pulled it away. My mouth was dry, my lips cracked, and I instinctively tried to wet them, rolling my tongue over them as I struggled to bring some moisture back.

Before I could fully recover, I felt something firm press against my lips—the riding crop. My breath caught in my throat. "Bite," he commanded, his voice low, steady, and firm. I obeyed instantly, my teeth closing around the leather-covered end of the crop. I could taste it: faintly metallic, slightly bitter, and strangely intoxicating. He lingered for a moment, letting me hold it there as if testing my obedience. Then he said, "Release," and I let it drop from my mouth.

He began circling me again, his boots brushing softly against the floor, his movements as slow and deliberate as before. My head was spinning, trying to follow him, to predict what he would do next, but he gave me nothing. Suddenly, the crop was back against my lips, and he repeated the order: "Bite." This time, I clamped down harder, eager to please him, eager to prove myself. He lingered again, letting the moment stretch, making me hold it as I trembled with the effort of remaining still.

When he pulled the crop away again, I heard him step closer, and I felt his boot against me—high, firm, pressing into my crotch. My breath hitched as my body tensed. The pressure sent a jolt of sensation through me, and I couldn't help but shift slightly, gasping for air. For a moment, I thought he might kick me. The idea sent a thrill of fear and excitement through me, but instead, he pulled his foot away, leaving me teetering on the edge of relief and frustration.

Then the crop was back again. This time, he pressed it against my lips but didn’t stop there. Slowly, deliberately, he pushed it further into my mouth. I opened wide, letting it slide in, the leather shaft grazing my tongue. He pushed it deeper, past the point of comfort, testing my limits. My breathing quickened, shallow and uneven, as I fought against the gag reflex building at the back of my throat. He pulled it out slightly, then pushed it back in again, repeating the motion with increasing intensity, simulating oral sex. My cheeks burned with humiliation and arousal as I struggled to take it, to submit to the rhythm he set. Just as I thought I couldn’t handle any more, he pulled the crop out completely, leaving me gasping for air.

I felt him move behind me, the soft creak of leather signaling his approach. The crop trailed down my back now, cool against my heated skin, making me shiver. He moved it with agonizing slowness, teasing me, taunting me, letting me feel every inch of it. Then, without warning, he tapped it lightly against my bare cheeks. The contact was barely more than a whisper, but it sent a jolt through me, my body instinctively tensing in response.

I knelt there, my breathing ragged, my body trembling, completely at his mercy. I didn’t know what would come next, but I knew I wanted more.

The room fell silent again as his boots moved away from me, the sound fading into the distance. My chest rose and fell with shaky breaths, my skin damp with sweat as I knelt there, waiting. I listened intently, trying to sense where he was or what he was doing. Then I heard it—the familiar creak of leather, but this time it was different. It wasn’t the sound of his boots against the floor. It was the groan of leather stretching and compressing as he sat down. I imagined him in the chair from his profile picture, the same confident, commanding posture that had drawn me to him in the first place.

His voice cut through the silence, calm yet firm. “Crawl to me,” he said.

I hesitated for only a moment, shifting from my kneeling position onto all fours. My limbs were stiff, and I felt slightly off-balance, but I did my best to steady myself. My knees and hands pressed against the floor as I began to move, inching toward the sound of his voice. The hood I wore blocked my vision completely, and I could only rely on sound and instinct to guide me. My breathing quickened as I got closer, each movement a mix of awkwardness and determination.

Then my head bumped against his leg—a solid, leather-clad thigh that stopped me in my tracks. My stomach clenched in embarrassment, but he didn’t reprimand me. Instead, he simply let me linger there for a moment before giving his next command. “Good,” he said, his voice low and controlled. “Now lick.”

I paused, the weight of the order settling over me. I lowered my head to the floor, my lips brushing against the leather of his boot. Slowly, tentatively, I began to lick, my tongue gliding over the smooth surface. The taste was faintly salty, a mix of leather and the heat of his body. “Slowly,” he warned, his tone sharp, cutting through my nerves.

I obeyed, moving upward with deliberate care, tracing the seam of his boot with my tongue. But I must have gone too fast because his gloved hand suddenly gripped my hooded head, stopping me in my tracks. “No,” he said firmly. “From the beginning.” He pushed me back down to the base of his boot, and I started over, my cheeks burning with frustration and arousal.

Each time I tried to climb higher, I found myself going too quickly, too eager to please, and each time he forced me back down, his grip strong and unyielding. The pressure of his hand on my hood sent a thrill through me, a reminder of his control and my submission. By the fifth attempt, I finally managed to get it right. My tongue moved painstakingly slow, following the line of his boot to his trousers, my body trembling with the effort of holding myself back. When I reached the top, my head was level with his crotch, and I could feel the heat radiating from his body. His thighs framed my face, the leather pressing against my cheeks, and my heart pounded in my chest.

I stayed there, motionless, as I felt his hands move to the laces of the hood. My breath hitched as he began to untie it, the soft scrape of leather against leather filling the room. The hood loosened, and finally, he pulled it off. The air felt cool against my damp skin, and I blinked rapidly as my eyes struggled to adjust to the light. Everything was a blur at first, the world coming back into focus slowly. I was so close to him, my face mere inches from his leather jock, that I couldn’t see much else. The scent of leather was overwhelming, intoxicating, and I could feel the strength of his thighs against my face, the sheer power of his body enveloping me.

I wanted to look up, to see his face, to take in every detail of the man who had brought me to this moment. But I didn’t dare. I knew my place. He was my master, and this was his game. All I could do was wait, trembling with anticipation, desperate for whatever he had planned next.

I knelt there, my breathing shallow and my senses overwhelmed. The smell of leather was thick in the air, mixing with the musk of his body, and I could feel the heat radiating from him, so close to me. My lips tingled with anticipation as I waited for his next command, desperate to please him, to show him that I was worthy of his attention. He was silent for a long moment, letting the tension build, before finally speaking.

“Start from the tip,” he said, his voice low and steady, as he undid his jock.

I swallowed hard, my mouth still dry, and leaned forward, my lips hovering over him. My eyes were locked on the tip of his cock, barely concealed by the tight leather jockstrap. My pulse quickened as I hesitated, unsure if I should begin on my own or wait for further instruction. He didn’t rush me, didn’t move, just waited patiently, letting the pressure build in my mind.

Tentatively, I extended my tongue, flicking it lightly against him. The leather was warm and smooth, and I moved slowly, barely daring to breathe as I focused all my attention on the tip. I circled it with my tongue, following the curve with deliberate care, tasting him as I went. I wanted to go further, to take more, but I held back, remembering his earlier warnings about patience. This was his show, not mine, and I knew that any misstep would only earn me another lesson in control.

“Good,” he murmured, his voice rumbling above me like a growl. “Now further.”

I obeyed instantly, trailing my tongue downward, tracing the shape of his cock through the leather. My hands remained at my sides, trembling slightly as I resisted the urge to steady myself against his thighs. I worked my way down inch by inch, savoring every moment, every taste, until I reached the base. I paused there, waiting for his approval, my breath coming in short, shallow gasps.

“Again,” he commanded. “Start over. Slower.”

I bit back a groan of frustration but obeyed, pulling back and starting again at the tip. Each time, I went slower, more deliberate, forcing myself to focus on the task and nothing else. His hands remained at his sides, but I could feel his presence looming over me, his dominance a palpable force that made my skin prickle with excitement.

When he was satisfied, he shifted in the chair, and I felt him rise to his feet. The sound of leather creaking and boots settling on the floor filled my ears, and I instinctively leaned back to give him room. He loomed above me now, his full height and presence making me feel small, insignificant, and utterly his.

“Stay where you are,” he said, his tone sharp, almost teasing. He adjusted himself, the leather of his jockstrap creaking as he pulled it down, finally revealing himself fully. My breath hitched as I looked up, my gaze drawn to him like a magnet.

“From the tip,” he repeated, stepping forward so that I had no choice but to tilt my head back, his cock inches from my face.

I leaned forward again, my lips brushing against him, and I began to work my way down, slowly, carefully, taking him into my mouth inch by inch. He reached out, his gloved hand gripping the back of my head, not forcefully, but with enough pressure to guide me, to remind me that I was under his control.

As I took more of him, he began to move, slowly at first, his hips rocking gently forward and back. I could feel his cock growing harder against my tongue, filling my mouth, and I fought to keep up with him, my head moving in time with his rhythm. He didn’t speak, didn’t make a sound, but his control over me was absolute.

Then he began to thrust in earnest, his movements firm and deliberate. My hands instinctively reached for his thighs, gripping the leather for support as he took me deeper, filling my mouth completely. My heart raced as I struggled to keep up, to give him what he wanted, to surrender to him completely. Every inch of me belonged to him in that moment, and I reveled in the feeling of being used, of being exactly where I was meant to be.

My mouth felt empty as he pulled out, leaving me gasping softly, saliva dripping down my chin. My tongue flicked across my lips instinctively, tasting him still, but the absence was maddening. My cock was throbbing, achingly hard, the frustration of not being touched driving me nearly mad. I could feel the strain in my body, every nerve ending hyper-aware of him towering over me.

As I knelt there, trying to steady my breath, I dared to look up. For the first time, I saw his face clearly. The sharpness of his jawline, the confident smirk, and the piercing eyes that seemed to see straight through me—it was all exactly as I had imagined, maybe even more so. He was striking, a vision of control and dominance wrapped in leather and presence. My heart raced as I locked eyes with him for a fleeting moment before quickly lowering my gaze in deference.

He noticed my arousal, his eyes flicking downward to my erection, which was straining painfully against its freedom. The tension in the air was palpable, and I couldn’t help but squirm slightly under his gaze. Then he spoke, his voice calm but laced with wicked amusement.

“You’ve got two options,” he said. “I can lock that pathetic little cock of yours in chastity for the rest of the session, or”—he paused, leaning closer, his gloved hand tracing the air near my throbbing cock—“I can kick you in the balls. Hard.”

My stomach dropped, and my head spun with the implications of his words. Chastity or pain—neither option was what I wanted. What I wanted was obvious. I wanted release. I wanted him to make me come, to finally let go of the unbearable tension that had been building since I walked into this room. But the choice he presented offered no such relief.

I hesitated, my mind racing. A chastity device would mean denial, the cruelest frustration of knowing that my cock would be locked away, rendered useless for his amusement. But the alternative—his boot connecting with my most sensitive parts—made me shudder in fear. The thought of that sharp, sudden pain was almost unbearable, but... a strange part of me wondered if I deserved it, if I needed it.

“I…” My voice cracked, barely a whisper. “I think… I want…” My words faltered, and I swallowed hard. “I want you to kick me.”

He laughed, loud and sharp, a sound that cut through the air like a whip. The condescension in his amusement stung almost as much as his next words. “You’ve already forgotten the first rule,” he said, stepping closer, his gloved hand gripping my chin and tilting my face upward. His eyes bored into mine, and I felt small, insignificant, and completely at his mercy. “I decide what happens to you. You’re mine. You don’t get a choice.”

My heart raced as his words sank in. Of course, he was right. I wasn’t here to make decisions. I was here to surrender, to give myself over to him completely. I felt a flush of embarrassment and shame, but also a flicker of relief. He would decide. He always would.

Releasing my chin, he turned away briefly, and I heard him rummaging through something—a drawer, perhaps. My body tensed, my mind racing with possibilities, until he turned back to me, holding a chastity device in one hand. The metal gleamed in the light, cold and unforgiving.

“You’re going to have your cock locked away,” he said with a smirk. My breath hitched at his words, my confusion growing as he tossed the device onto the nearby table. What did he have planned instead? What punishment—or pleasure—awaited me next? My cock twitched involuntarily, and I bit my lip, knowing that whatever came next, I was utterly his.

He tilted his head slightly, a cruel smirk curling his lips as he gazed down at me. “You’re too hard,” he said, his voice dripping with mockery. “That cock of yours is refusing to cooperate. Can’t have that now, can we?”

I barely had time to process his words before it happened. Without warning, he lashed out, his boot connecting with me so hard that the world around me blurred. The pain exploded through my body like fire, sharp and unforgiving, and I collapsed to the floor, gasping for breath. For a moment, I couldn’t think, couldn’t move, couldn’t do anything but reel from the shock. My vision darkened at the edges, and my chest heaved as I struggled to regain control.

The suddenness of it was almost more devastating than the pain itself. My mind raced, and for the first time since arriving at his house, I felt regret—raw and suffocating. Why did I come here? The thought echoed in my head, louder than the pounding of my heart. I had been so eager, so desperate to serve him, but now, sprawled on the floor with agony coursing through me, I felt a wave of doubt. No matter how attractive he was, no matter how commanding or charismatic, I didn’t know if I could handle this. The pain was too much, and I felt utterly broken.

But then, something shifted. A different thought crept into my mind, tentative at first but growing stronger with each passing second. You wanted this. The realization hit me like a second blow. I had come here to give myself to him, completely, without reservation. This wasn’t about comfort or ease; this was about surrender. About proving my worth—or lack thereof. About being nothing. And if anyone was going to reduce me to that state, it was going to be him.

He was the embodiment of control, strength, and power, and I craved his approval as much as I feared his wrath. The pain wasn’t just punishment; it was a test. A measure of how much I was willing to endure, how far I was willing to go to please him. I wanted this. I needed this.

Gritting my teeth, I forced myself to move. My limbs felt heavy, and my head was still spinning, but I pushed through the pain. Slowly, shakily, I rose back to my knees, my body trembling but my resolve solidifying with each passing second. When I was finally upright again, I bowed my head, waiting for him to notice, to acknowledge that I was still here, still his.

He didn’t say a word, but I could feel his approval in the way he loomed over me, his presence suffocating and intoxicating all at once. I braced myself for what was coming, knowing that this was only the beginning. The pain, the humiliation—it would all pale in comparison to what he had planned. And I would take it all, for him, because he was my master, and I was his to break.

His boots shifted slightly, the leather creaking as he reached down for something. I didn’t dare look up, but I heard the faint metallic clink and knew immediately what it was. The chastity device.

“Good boy,” he said, his voice softer now but no less commanding. “You’re learning.”

He stepped closer, the gleaming device now in his hand, and I couldn’t help the shiver that ran down my spine. He knelt slightly, bringing the device level with my throbbing cock. The anticipation was unbearable, but I held perfectly still, not daring to move or speak.

“This is where you belong,” he said, and the cold, unyielding metal pressed against my skin.

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