Being Brave in Chicago

 Being Brave in Chicago

Story by Lisa

Inspired by Mountain Man John and a picture (below)

Prologue - A few years ago I posted this picture on "Similar Worlds" with the comment "I was so unsure about meeting him. I was in Chicago at a teachers conference. I brought my toys and with a shaky hand I texted my room number to him." A few days later Mountain Man John replied with this comment, "“There will be a keycard at the front desk for you, Sir” she amended with another text. Some time later, she was startled awake … had she actually slept? It took her a moment to remember where she was and realize what had woken her up – someone had accessed the electronic reader on the door, and the engaging of the heavy latching mechanism was loud in the still hotel room. She instantly became aware of the cool air from the AC blowing on her bare bottom. The hairs on the back of her neck prickled, as they stood on end and the knots in her stomach tightened. There was no turning back now …" I decided to write this story... it is has been on and off for past year or so.... here is the final story...

Thwack.

The sound was a sharp, wet crack that seemed to echo off the high hotel ceiling. My whole body jolted, a gasp tearing from my throat. The heat bloomed instantly, a fierce, stinging flower of pain right on the crest of my left cheek.

Thwack.

Another, on the right this time. Symmetry in agony. My fingers clawed at the white duvet cover, twisting the fabric into desperate knots.

“Count,” his voice rumbled from above me, a low, calm baritone that vibrated through his chest and into my spine, where I lay draped, utterly exposed, over his solid thighs.

“One,” I choked out, my voice muffled by the bedding.

Thwack.

“Two.”

It started with the sound of the door.

Some time later, I was startled awake… had I actually slept? It took me a moment to remember where I was and realize what had woken me up – someone had accessed the electronic reader on the door, and the engagement of the heavy latching mechanism was loud in the still hotel room. I instantly became aware of the cool air from the AC blowing on my bare bottom. The hairs on the back of my neck prickled, as they stood on end and the knots in my stomach tightened. There was no turning back now.

I didn’t move. I’d arranged myself carefully before my nervous nap: prone on the king bed, my face turned away from the door, my christmas pajama bottoms pushed down to mid-calf, the soft cotton a pointless ring around my ankles. My upper body was covered by the top. The rest of me was on stark, vulnerable display. The small arsenal I’d unpacked with trembling hands—a slender black cane, a supple leather strap, a tiny flogger with silky falls—lay on the bed next to me like surgical instruments.

The door opened, then closed with a soft, definitive thud. A lock engaged. Footsteps, measured and quiet, crossed the plush carpet.

I held my breath, I looked over my shoulder at him when… .

He came into my line of sight, and the air left my lungs in a quiet rush. George. Or not-George. He was… more. Tall, broad-shouldered, filling his crisp, white dress shirt and dark trousers with a tangible, masculine presence. His hair was salt-and-pepper, cut short and neat. His face was handsome in a stern, lived-in way, with lines at the eyes that suggested he smiled, though he wasn’t smiling now. His gaze was direct, a cool, assessing blue that swept over the room, over the toys, and finally, finally, landed on me.

On my bare skin.

A flush that had nothing to do with shame and everything to do with a sudden, dizzying rush of arousal heated my chest and face. I was completely known to him at that moment, in a way no one else had ever known me. The fantasy “Judy” was gone, stripped away with my pajamas, leaving only Lisa, trembling and exposed.

He didn’t speak at first. He placed a leather briefcase by the grey cloth couch, then slowly removed his suit jacket, folding it neatly over the back of a chair. The deliberate, quiet movements were more unnerving than any greeting. He rolled up his sleeves, revealing strong forearms dusted with that same grey-flecked hair. My heart hammered against the mattress.

Finally, he approached the bed. He didn’t touch me. He simply stood there, letting me feel the weight of his scrutiny.

“Judy,” he said. His voice was exactly as it had been in our late-night calls—assured, warm, but with an undercurrent of steel. “Or should I say, Lisa?”

“Lisa,” I whispered. “Please.”

A faint, almost imperceptible nod. “You prepared the tools. You assumed the position. Good.” His eyes trailed over the curve of my bottom. “You’re nervous.”

It wasn’t a question. I managed a tiny nod, my cheek scraping against the duvet.

“That’s appropriate. This is a serious thing you’ve asked for. A gift you’re giving, and a trust you’re placing.” He paused. “Do you want to proceed, Lisa? Now, while you’re cold and afraid? You may safeword at any time. Red for stop. Yellow for pause. Do you remember?”

“Yes,” I breathed. “Green… for green.”

“Good girl.” The praise, low and sincere, sent a new, different shiver through me. “Then we begin with the basics. The connection of hand to skin. The foundation.”

He had me stand in front of him and then had me step out of the pj bottoms. He sat on the edge of the bed, the mattress dipping profoundly under his weight, reached out and pulled me over his lap. A large, warm hand settled on the small of my back, not restraining, just present. His other hand smoothed over one pale globe of my bottom, a slow, almost clinical caress. My skin jumped at the contact, goosebumps rising.

“Cold,” he murmured. “We’ll warm you up.”

And then his hand lifted.

The first spank wasn’t hard. It was a firm, crisp pat that made me flinch more from surprise than pain. The sound was shockingly intimate in the quiet room.

Smack.

Another, on the same spot. A low, spreading heat began to build.

Smack. Smack. Smack.

He began a slow, rhythmic tempo, covering every inch of my sitting area with those firm, stinging slaps. The pain was bright and clean, a sharp focus that drove every other thought from my head—the conference, my students, the strange city outside. There was only the sound, the heat, the heavy pressure of his thighs under my belly, and the solid, warm hand on my back.

The pace increased. The spanks grew harder. The sharp cracks became louder, wetter. A low whimper escaped me. My toes curled.

“Breathe, Lisa,” he instructed, his voice still calm. “Don’t hold your breath. In… and out.”

I tried to obey, gasping into the duvet as the fire built. He was methodical, thorough, painting my skin with a uniform, pink blush. The sting began to deepen into a throbbing, pervasive ache. I squirmed, my hips giving an involuntary little jerk.

His hand paused, resting on the now-hot skin. “The easy part is over,” he said. “Now, we count. You will thank me for each one. Do you understand?”

“Yes,” I whimpered.

His hand lifted higher. I tensed, every muscle clenching.

THWACK.

The blow landed with a force that drove the air from my lungs. It wasn’t just a spank; it was a statement. A bolt of pure, white-hot sensation exploded across my skin.

“One,” I sobbed. “Th-thank you.”

THWACK.

“Two! Thank you!”

He found a brutal, perfect rhythm. Each heavy, open-palmed blow landed with precise, devastating impact, layering pain upon pain on the same tenderizing flesh. My world narrowed to the cycle: the searing impact, the blinding flash of hurt, the gasped number, the choked gratitude, and the half-second of dreadful anticipation before the next one fell.

By ten, I was crying freely, hot tears soaking the duvet. By fifteen, my body was bucking against his hold, my pleas and thanks becoming a messy, incoherent litany. The heat was incredible, a radiating furnace that consumed my entire backside. I was raw, exposed, completely undone.

He stopped at twenty. His hand, the instrument of my torment, came to rest gently on the blazing skin, rubbing in slow, soothing circles. The contrast was exquisite torture. I shuddered, a broken, wet sound escaping me.

“Very good,” he murmured. “You took that beautifully. But we’re just beginning.”

He helped me to stand. My legs were jelly, my face was a tear-streaked mess. I could feel the fierce heat radiating from my backside, the skin tight and throbbing. He guided me, his hands firm on my shoulders, to the left side of the dresser. He positioned me, bending me over the dark wood dresser, my chest pressed to the cool, smooth surface. My reddened bottom was presented high, an offering to the room.

“The strap,” he said.

I heard him move to the nightstand, where he had moved the implements. The soft shush of leather being lifted. My heart, which had begun to slow, seized again.

He didn’t make me wait. I heard the soft swish of it cutting the air a moment before it landed.

THWAP!

The pain was different. Broader, deeper, a dense, thunderous ache that sank into the muscle beneath the skin. A sharp cry was torn from me.

THWAP!

It landed an inch lower. The ache spread, merging with the sting from his hand into a symphony of hurt. He was an artist, and my skin was his canvas. He used the strap in measured, heavy strokes, covering the territory he’d already pinkened, driving the heat and the pain to a new, profound depth. The cries turned to ragged sobs. I gripped the footboard until my knuckles were white, my body arching and twisting with each blow.

He paused, running the cool, smooth leather over the burning welts. “Halfway,” he said, his voice a little thicker now. I could hear his own breathing, deeper, more controlled. The realization that he was affected, that this was winding a tight coil inside him too, sent a desperate, shameful thrill through my core. I was soaked, my own arousal a slick, undeniable truth between my thighs.

“Please,” I heard myself beg, not knowing what I was asking for.

He answered with the cane.

It was the smallest implement, but it inspired the most primal fear. He had me kneel on the grey couch, my upper body draped over its back, my welted, throbbing bottom presented at a perfect, vulnerable angle.

The first stroke was a revelation.

SWISH-CRACK!

A thin, blazing line of pure, concentrated fire etched itself across the crest of both cheeks. It was a pain so sharp, so specific, it stole my voice. All that came out was a strangled gasp.

SWISH-CRACK!

Another line, parallel and just below. Tears streamed down my face silently now. The pain was beyond crying out. It was a bright, clean agony that sang through my nerves, lighting up my entire being. He gave me six, each one a masterpiece of precise torment, each one layering a new, searing stripe over the broad, aching bruise of the strap and the general fiery blush of his hand.

When it was over, I collapsed forward over the couch, a boneless, weeping heap. I was a raw, exposed nerve. Every breath made the welts throb. The room swam.

I felt him kneel beside me. His hands, so capable of delivering such pain, were suddenly infinitely gentle. He gathered me up, pulling me into his lap as he sat on the couch. I curled into his chest, my tears soaking his shirt, my sore bottom carefully suspended in the cool air. He held me, one strong arm around my shoulders, the other stroking my hair, shushing me softly.

“Shhh, Lisa. You did so well. So perfectly. It’s over now. Just breathe. Let it go.”

His tenderness undid me more completely than the cane ever could. Great, heaving sobs wracked my body as the storm of sensation—pain, shame, vulnerability, and a shocking, profound arousal—crashed over me. I could feel the hard ridge of his erection pressed against my hip through his trousers, a mirror to my own desperate, slick need. We were both there, in the aftermath, laid bare.

He held me for a long time, until my cries subsided into hiccups and shivers. He fetched a cool washcloth from the amazing bathroom and gently dabbed my face. He didn’t touch the angry, welted landscape of my bottom, letting the air soothe it. He just held me, his presence a solid anchor in my shattered world.

Eventually, my breathing evened out. The sharpest edges of the pain had softened into a deep, glowing, full-body ache. A heavy, spent calm settled over me. I nuzzled into his chest, inhaling the scent of his soap and starch and skin.

“I have to go,” he said softly, his lips against my hair.

I nodded, unable to speak. He shifted, helping me to stand on wobbly legs. He pulled my pajama bottoms up with exquisite care, the soft cotton a whisper over my tortured skin. He dressed himself, putting his jacket back on, becoming the handsome, anonymous stranger once more.

He paused at the door, his hand on the handle. He looked back at me, standing there in the dim room, wrecked and whole.

“Thank you, Lisa,” he said, and his voice held a world of sincerity. He continued, “We’ll talk again later and maybe we can meet again.” I nodded and said, “Yes sir.” as I smiled back at him. 

Then he was gone. The door latched shut with a soft click. I was alone, the ghost of his hands and the fire on my skin the only proof he had ever been real.