Chapter Fifteen
I nside, Leo walked me to the cough, his hand hovering just above the small of my back.
“Sit,” he said gently, his tone leaving no room for argument.
I sank into the cushions, my legs still unsteady beneath me. He returned moments later with a glass of water, taking it with tremblings.
“Are you sure you’re okay?” he asked.
I took a sip, trying to steady my nerves.
I nodded, “Yeah, I’m okay...” taking a sip, “I think.”
The evening started off perfect—better than perfect, even. Em and I had hashed out some awkward truths, but then Kyle...my stomach turned at the memory of him—his weight pressing against me, his hand where it had not right to be. I tried to push the thought away, but it clung to me, sour and inescapable.
Leo sat beside me, his eyes steady and searching, “Drew, you don’t have to pretend. Not with me.” His hand rested lightly on my knee with reassurance.
His presence and warmth grounded me in a way I really needed at this moment. It radiated through every touch, given a small sense of safety back.
“I just can’t believe it happened,” I admitted.
Leo’s hand tightened around my knee, his jaw clenching,” Some people hide their true nature well. But it’s over now, Drew. He won’t hurt you again, I promise.”
Nodding, though the weight of the encounter still pressed knowing that Leo was right. Kyle wouldn’t get another chance. Not with Leo protecting me and the police hunting him down.
Fear seems to take space currently, leaving a bitter taste in my mouth. I moved closer, adjusting us so I could wrap his arm around my shoulders, pulling me into him. Once we got comfortable, my ear rested on his chest, letting the steady rhythm of his breathing calm my frayed nerves.
“Thank you,” I whispered, “For being there, for...stopping him.”
“Always,” Leo replied, his lips brushing against my temple, “I’m here for you, Drew. No matter what.”
I closed my eyes, letting his words wash over me.
“As my boyfriend?” I said, the words tumbling out unbidden.
“Boyfriend?” He repeated.
“After tonight, there’s no doubt I want you to be your boyfriend and you mine.”
Leo didn’t say a word.
I added, ”And you’re submissive.”
“Are you sure about this? We haven’t even experienced anything just yet,” Leo said, his voice softened.
Pulling slightly from his arm, I met his eyes where I could tell he was thrilled to hear me say that we’re now boyfriends, let alone being his submissive.
There was only one response I knew that befitted.
“Then enlighten me,” I said, pausing for a moment, “Take me to the playroom.”
He leaned in, his lips brushing against mine in a soft, lingering kiss igniting a fire deep within me. The kiss was tender, yet it carried the promise of something more-something powerful and consuming.
When Leo pulled back, he studied me for a moment, his gaze searching for mine for any hesitation. He wouldn’t find any, this is what I want. Offering me a reassuring smile before standing up, I did the same where he led me through the house again walking down the familiar hallway, and yet felt different-a surge of excitement took over.
Pulling the large painting away from the wall and entering the code, his hand placed delicately on the door handle ready to turn it but was met with a pause and turned his head slightly, “Remember this is a space where trust is everything, Drew. We go as far as you’re comfortable with, and if at any point you want to stop...don’t hesitate. Do you have a safe word in mind?”
Each word he spoke was laced with care and consideration, making it clear that my comfort and safety were his top priorities. Reinforcing the trust I’d already placed in him.
“I know, Leo. I wouldn’t be asking if I didn’t.”
“And your word?”
Not expecting to be placed on the spot like this, but at the same time it was needed-this word had to be unique. Taking another moment to think, searching for something that felt right, something that would stand out in the heat of the moment.
My mind wandered through various possibilities until one word surfaced-a word that embodied the ideas of transformation, of venturing down a rabbit hole into the unknown and forever changed.
“Cheshire,” I finally said, the word slipping from my lips with a sense of certainty.
“Cheshire it is...remember it,” he said, giving me a nod.
He turned the handle and opened the door, stepping in first, holding the door open for me. I followed, my heart beating a little faster with each step.
The soft click of the door shutting echoed in the silence. He turned to face me, his eyes reflecting both desire and care.
“We’ll start off slow,” he said, voice gentle yet commanding, “Just follow my lead.”
“Yes, Master Leo,” I replied, the words unfamiliar on my tongue, yet somehow...right.
Pleased by my answer Leo says, “Over there on bed is a box,” Looking past his shoulder, a medium sized white box wrapped in a large black ribbon laid before us. ”Take that box around the corner as there is a room, please wear only what’s inside.”
“Yes sir,” I said in an understanding voice.
Doing as instructed, I walked past Master Leo taking the box from the bed, which was extremely light, and headed towards some black curtains matching the bed sheets which I’ve never noticed before.
Slipping through, it was a decent sized room lit by nothing but neon red lights. There was a small vanity with a chair and large full length mirror. Placing the box on the vanity, I stripped off the reminisce of my tuxedo until I was in my briefs folding them on the back of the chair.
Pulling the ribbon off, I was unsure of what to expect. Removing the lid, it was a glittery black bunny eye mask and nothing else. I ran my fingers over the soft glossy texture of the mask. The simplicity of the item only heightened ectasy about it–something that spoke to the nature of what was about to happen.
Slipping it over my eyes, I adjusted it until it fit snugly against my face and walked over to the mirror. The reflection staring back at me was myself and someone new.
The neon red light cast a faint, otherworldly glow across my figure, accentuating the curve of my jaw line and the slight parting of my lips as I breathed-I’d never seen myself like this before.
So exposed, yet so empowered.
Each second spent looking at my reflection seemed to intensify the sensation, the mask acting as both a shield and a conduit for the sensual side of myself. My pulse quickened with anticipation as I imagined what Master Leo would think, what he would do when he saw me like this.
There was one last thing to do. Master Leo’s only instructions was for me to wear the mask, nothing else, which meant stepping back out completely naked. It wasn’t the nudity itself that unsettled me—he had already seen every inch of me, explored me in ways that left no secrets. It was the vulnerability of it all.
Every time we are together, he pushes boundaries, drawing me into something new, something uncharted. Tonight was no exception.
I took a deep breath, feeling the cool air brush against my skin as I left the small boudoir and made my way back to Master Leo.
Once in the main room, the environment shifted dramatically. Darkness cloaked the space, turning it into an intimate abyss. The only source of light came from above—a soft, sultry glow in shades of deep amber and crimson. It bathed the bed in warm, seductive hues, casting gentle shadows that danced across the silky sheets. The light was low and inviting, its intensity akin to the flicker of a candle, teasing the eye and drawing attention to every curve and fold.
“Don’t be shy,” Master Leo said, “Come to the bed.”
Without saying any word, I casually walked over standing only a few inches away unsure what to do next.
Master Leo’s presence was magnetic, commanding the room even in the near darkness. The spotlight carved long shadows into the space, making it feel both confined and infinite at once. He didn’t move closer, his exact location unclear, yet the weight of his gaze was unmistakable—like a physical touch that traced every inch of my exposed skin.
“You look...exquisite,” Leo murmured, his voice low and filled with approval.
The praise felt sexy to me. Here I was standing in a room completely naked with nothing but a bunny eye mask on and a spotlight showing every bit of me.
I started to get hard.
“The mask suits you. It brings out something rather primal that’s been waiting to be unleashed.”
“Thank you, sir,” I told him.
There was a moment of silence.
“I see you’re getting aroused. Your dick gets harder with every passing second. Tell me, boy, does this please you?”
He wasn’t wrong. My dick was semi-hard and growing as my balls ached. I could feel his gaze still traveling over my body, taking every inch of me. It made me feel worshiped, like I was the most precious thing in his world at the moment.
“It does please me, sir,” I responded.
“And the mask, how does it make you feel?”
What was I going to say?
I didn’t want to say the wrong thing and kill what hasn’t even started. I wanted to say all the right things...things that would drive my dominant crazy, make him pleased, and pulse race with just my words.
“The mask makes me feel…” I lingered. ”Desired. Sexy. Obedient.”
“Obedient?” Leo repeated, “Are you going to obey me?”
“Fully,” I said.
“I want you to get on the bed and kneel.”
I complied, my knees sinking into the mattress surface. The Position felt vulnerable, but the sound of Leo’s voice kept any fear at bay.
“Spread your legs a bit, just enough to keep you steady.”
Repositioning my leg, I rested my ass on the heels of my feet, placing my hands on my thighs awaiting further instructions.
“Good boy. Now, I want you to take your hands and start from the top of your chest and slowly roam over every inch of you-no part of you is to be left untouched. Understood?”
“Yes, sir.”
My hands migrated up to my pecs pressing softly and gradually running them down. The act of touching myself in this manner, knowing Leo was watching, added an extra layer of intimacy and excitement to my core.
The sensation of my fingers brushing over my nipples, teasing the sensitive flesh, drew a soft gasp from my lips as they hardened-a sound I knew he would savor.
“Beautiful,” Leo’s voice cut through the darkness like velvet, smooth and commanding. “I want to see you lose yourself, Drew. let the pleasure take over.”
As I continued down, tracing the lines of my abs, feeling the tension coiled beneath the surface, ready to snap. It was maddening, each area my hand grazed heightening the ache between my legs.
“You’re pre-cumming.”
I looked down to find a string of glistening fluid left the tip of my cock, nearly reaching the sheets. Normally when I pre-cum it's usually a dribble, nothing compared to this.
“Touching yourself for me must be a bigger turn on than you realized,” his voice thick with approval, a dark edge of desire lacing his words.
How words sent a fresh surge of arousal through me, and I bit my bottom lip, trying to stifle the moan that threatened to escape. When my fingers finally wrapped around my erection, I let out a breath I hadn’t realized I was holding. The warmth of my own grip, coupled with the goosebumps on my skin, made the first stroke electrifying.
“You know what would please me?” Leo asked.
“What would please you sir?”
“Before you stroke yourself, I want you to taste your own pre-cum. Relish the taste in your mouth.”
I have never done anything like that before.
Tonight, Master Leo is not holding back and I didn’t want him to. This was exactly what I wanted. Being told what to do and I obeying his every whim, without a hint of hesitation.
Pausing for just a second, allowing the weight of Leo’s command to settle in. The idea of tasting my own pre-cum was both thrilling and slightly intimidating. Yet, pleasing Master Leo ignited a fire within me. My need to satisfy him eclipsed every shred of doubt, leaving only an urge to submit entirely to his command.
Wiping up the dripping mess with my fingers, watching as the click fluid clung to my skin, my lips parted and the tip of my tongue teased the edge of my finger, savoring the salty, slightly sweet taste as it spread across my tongue. I closed my eyes, letting the flavor linger.
It was strange, tasting myself like this felt erotic. The same fluid that Master Leo wanted to savor all the way home the first night we truly connected. I swallowed, feeling a sense of pride in my obedience.
“Good boy,” Master Leo’s voice rumbled, “Now, continue stroking yourself. Slowly. I want you to enjoy every second of it.”
Wrapping my head around my cock again, this time with a new level of focus. Each stroke was deliberate, slow, and intentional. More pre-cum leaked out, easing the movement of my hand causing heat to build between my legs.
“I want you to keep going until you’re on the edge, until you can barely hold back,” Master Leo purred.
The rhythm of my hand was focused, waves of pleasure steadily building. The heat of each stroke spreads through my body, making me tremble with the effort to hold back.
“Stop,” his voice sharply cutting through the haze of pleasure.
Frozen, my hand stilling immediately, even though my body screamed for release. My body filled with tension was almost unbearable-sitting there, throbbing painfully with need, on the cusp of coming.
“Good boy,” he said, his voice soothing now, almost tender, “You’re close aren’t you?”
“Yes, sir,” I whisper, my voice shaky.
“Do you want to cum stroking yourself, or do you want to me to fuck the load out of you?”
“Fuck me, sir. I’m gonna cum if I touch myself,” I expressed mid-pant.
A small growl could be heard coming from the darkness.
“Lie back on the bed,” he commanded, filled with dark and dripping authority, “and spread your legs wide. I want to see every part of you.”
Feeling a little flushed, I obeyed, reclining onto the cool stain sheets. My thighs feel apart, allowing Master Leo complete exposure. The bed dipped under his weight as he approached, eyes roaming over me, devouring me like a predatory savoring his prey, making me tremble under his intent focus.
“I’m going to take you to your very edge, pushing you past where you’ve ever been before. Tell me again what your safe word is.”
“Cheshire,” I quickly tell him, more as a reminder to myself than anything.
“That’s right,” Master Leo said, his voice full of affection, “You’ve been a good boy. Now, just relax and let me take of you,”
And with that, he began to touch me, sliding over my skin with agonizing slowness starting from neck down to my cock. Master Leo’s lips claimed mine, soft at first, then hungry, coaxing a moan from deep in my throat as his teeth then grazed my bottom lip.
Master Leo shifted, pulling a cuff from behind him and around my wrist, the leather snug but not too tight. He repeated the process with the other wrist, and ankles.
In a swift move, chains restrained every cuff making me unable to move. He took a step back to admire his work, assessing and making sure I was still okay.
Saying the safe word at any moment would make all of this stop, but this has been the most comfortable I’ve ever been. Being expose like this made me fucking wanted.
Having a good look at Master Leo as he stepped back, he was already dressed for the occasion wearing nothing but a leather harness perfectly contoured to his predominant chest and distressed dark jeans that barely hugged his hips before slipping off.
Apparently come fuck me jeans are a real thing.
“I’m going to use a flogger now, do you know what that is?”
“No,” I tell him, “I’m a quick study, though.”
A smile tugged at the corner of his lips.
Reaching over to a side table, he carried what I assumed to be the flogger-a tool I had only heard about in foolish conversation. It was a leather-bound handle with multiple soft leather strands attached.
He let the strands drape across his hand as he approached, the sound of the leather brushing, a soft whisper in the otherwise silent room.
“This,” he started, holding the flogger in front of me, “is going to bring you slight pain with unyielding amounts of pleasure, in a way you’ve never felt before.”
“Yes, sir,” I replied, “You won’t have to repeat yourself.”
He furrowed an eyebrow with excitement. Trailing the soft leather strands across my chest, jolted me slightly to the unfamiliar sensation. He smiled. Then over my thighs-the sensation was light, almost ticklish, sending shivers and goosebumps all over. Each pass of the flogger left something in its wake.
He stepped back slightly, the tool resting loosely in his hand. Master Leo’s gaze was steady and calm, as if he were measuring not just my body but my readiness. His movements had a quiet authority, the kind that made my breath hitch before he’d even touch me.
When he raised the leather toy and let it fall across me, it landed with a soft snap—barely more than a caress—my nipples tightening instinctively in response. His lips curled into the faintest hint of a smile, though his focus remained absolute.
Again, he raised the strap, this time allowing the supple leather to linger on my skin before napping it back sharply. The sting was light but known. I bit my lip, trying not to whimper, but the sound escaped me anyway—a needy exhale that seemed to please him.
“How does it feel, boy?” he asked, voice low and thick.
Mid-breath, “Incredible,” my voice taking the leather’s onslaught sensations.
Smiling yet again, he was pleased with my response, “Good. I want you to remember this feeling, the control you have over it.”
Moving from my chest, he struck this time across my thighs, the sound of leather snapping against my skin with a sting let out a moan in me. The pain was more pronounced now, and yet, was of a delicious kind.
Master Leo didn’t relent. His strokes alternated between sharp, stinging strikes and softer, teasing caresses, each one purposeful. When he focused on my chest and thighs, the heat spread like fire beneath my skin, but when he drifted lower, near my cock, his movements became maddeningly delicate.
The softness there only amplified the ache, leaving me throbbing, my body begging for release. I knew better than to expect it—not yet. Master Leo wouldn’t allow it. He was testing me, pushing me to the edge of keeping me there, and I craved it as much as I feared it.
Each stroke was a contradiction, both punishment and reward. The sting of the harder hits sent a jolt through me, igniting nerves I didn’t even know existed, while the featherlight grazes made me tremble with frustration. My cock pulses in time with my racing heartbeat, straining, desperate, but I couldn’t let go. Not until he decided. That was the unspoken rule.
My body wasn’t my own in these moments—it was his instrument, his canvas. The tension was exquisite, a perfect blend of agony and anticipation. I let out a shuddering breath as I surrendered further, the ache in my thighs, my chest, my cock all blending into a heady cocktail of desire.
I wanted to beg, but I wouldn’t—not yet. Instead, I arched toward him, silently pleading, knowing he could see the surrender in my eyes, This what he wanted. To push me further. To see how far I’d go. And I was ready to fall apart for him, one aching, sultry stroke at a time.
I was on the edge.
I ready and wanting him to fill my hole and fuck me senseless.
“Fuck me,” I loudly said.
Master Leo slowed down, bringing the flogger to rest against my skin. He leaned in close, his breath against my ear, “Does my boy want to be fucked now?”
“Please,” I said, barely audible.
“Please what?” He asked, his voice teasing.
“Please fuck me until I cum,” I begged.
Leo stilled for a moment, I thought he might deny me. But then shifted, adjusting the straps, and positioned himself between my legs as his weight pressed against me. The tip of his cock teasingly grazed the entrance and stayed there for a beat, and I thought I might unravel entirely before he even began.
When he finally pushed forward, his cock entering me, my body opened for him in a slow, delicious stretch that made my toes curl. A sound escaped me—soft and unguarded.
“Master..." I said, a whisper like prayer on my lips.
“That’s it, boy. Let me in.”
Master Leo pushed into me, filling me inch by inch that had me moaning low in my throat.
“You’re so tight,” Leo groaned, gripping my hips as he buried himself inside me, “Fuck!”
Allowing me to adjust, stretch, my hands clenched into fists. My breaths deeper and more apparent, he thrusted into a punishing rhythm. Each one drove me closer and closer to my edge.
He moved slow at first, making me feel every inch of his cock as he reached my prostate, tethering me to the moment. His hand trailed down the curve of my spine until it reached the swell of my ass, his thumb pressing and massaging the area adding an additional sensation of him pumping his cock into me.
The rhythm grew faster, each one a command my body couldn’t ignore—building relentlessly, as though he were playing a symphony composed of my every moan.
“Master Leo,” my voice broke.
“Hold on,” he commanded, his voice in a rough growl, “Not yet. I want you to feel you lose control, want to see you come apart under me.”
It was torture...pure sweet torture. Every nerve in my body was on fire, every thrust driving me closer to the edge until I was dangling over it. And then, just when I thought I couldn’t hold on any longer, Master Leo reached down, his hand wrapped around my cock.
“Cum for me, boy,” he ordered, his voice dark, “Now!”
His words were my undoing. I climaxed shuddering while Master Leo erratically thrusted, his grip on my hips tightening as he followed me over the edge, spilling inside me with a low guttural moan.
We were both still, the only sound in the room was our ragged breathing. Leo’s body was warm and solid against mine, his presence grounding me as the last waves of pleasure rolled through me.
Pulling out, and I whimpering at the loss, Master Le’s hand were gentle as he released the cuffs, pausing to massage the tender marks they had left on my wrists and ankles. My body quivered as he gathered me into his arms, holding me close as if to anchor me in the aftermath of it all.
I melted into him.
“I’m gonna take you to bed,” he whispered.
Master Leo carefully lifted me from the bed, his strong arms holding me close as he carried me from the playroom to the bedroom. The air between us felt charged, yet comforting, as the intensity of what just happened began to settle in my mind.