Midnight Letter

The lid was secured open, and he said

"come here boy".

Jake made his way, attempting to hide his cock. Richard slapped his hands away and hit the head of his cock. "Hands behind your back, boy."

He stood before the opened chest, and his heart raced and pounded in his chest.

The buffet was filled with all types of impact tools.

A paddle like the gym teacher at school had.

A second paddle painted black with 1/2" holes drilled in straight lines on it.

A narrow black leather belt.

A 2-1/2" wide black leather belt.

A Scottish tawse, a severe looking three stranded belt made of stiff leather, each finger 2" wide, connected to a wooden handle, covered with intricate braded leather.

A jockeys leather covered crop, and a severe looking British rattan cane with a hooped handle rounded out the collection. Richard pulled a knob to a drawer, and picked up a dark wooden handle, about 4" wide, which clamped on a stiched double layer of hard leather, 4" wide by 16" long. He slapped his hand with the implement and said "This will do nicely."

"Move to the chair boy"

Jake slowly obeyed, standing behind the back of the straight back wicker chair.

"Grab it with both hands and lean into it"

He immediately obeyed. The man stood behind him, and kicked the inside of his ankles, making him spread his legs wider. Then wider still. His balls hung between his legs, exposed, and in harms way.

Richard went to the buffet and extracted a container. He opened it and with two fingers pulled out a large glop of some type of oil product. He moved behind Jake, who noticeably flinched when he moved behind him. He started in the center of his lower back, then moved in circular motions on each buttock, then lower where the thigh joined the butt. Then between his cheeks, four fingers prodded and pulled upwards until finding his anus; Two, then three, then four fingers entered. Jake grunted and pushed away only to cause the fingers to go deeper. A free hand grabbed his neck and squeezed, lips near his ear......"Don't move boy".

The hand inside him pushed deeper still, him, still as can be, his breathing ragged and short.

The hand on his neck pushed him farther down, until the top of his head was in the seat of the chair.

"Don't move from this position"

"Do you understand?"

A meek "yes" bleated out.

Richard retrieved the harsh wooden leather

device, and slapped his hand with it, the sound echoing through the room.

Richard tested the weight of the wooden leather paddle in his palm, the thick slab of polished oak wrapped at the business end with a stiff, unforgiving strip of cured, stiff leather. The slap against his own hand had been sharp, promising. Jake's breathing hitched audibly, his body still locked in position--ass raised high, greased, legs splayed wide, balls hanging freely, head pressed down into the woven seat of the wicker chair, fingers white-knuckled around the backrest.

"Ten strokes to start," Richard said calmly, circling behind the trembling young man. "You will count each one. Miss a count and we begin again. Understood?"

"Yes... Sir," Jake whispered, voice already strained.

The first crack landed without warning--hard leather meeting oiled flesh with a loud, wet thwack. Jake jolted forward, a guttural cry escaping him as fire bloomed across his right cheek.

"One!"

The second came just as fast on the left side, lower, catching the tender undercurve where thigh met ass. Jake's hips bucked involuntarily.

"Two!"
Richard paused to admire his work: the skin already blooming a deep, angry pink beneath the sheen of oil. He dragged the cool edge of the paddle between Jake's spread cheeks, teasing the slick, stretched hole that still glistened from the earlier fingering.

"You're clenching, boy. That's only going to make it hurt more."

He brought the paddle down again, this time directly across both cheeks in a heavy, centered stroke that made the firm globes flatten and ripple. Jake's legs shook.

"Th-three!"

By the fifth stroke Jake was panting openly, sweat beginning to bead along his spine. His cock hung heavy and half-hard between his spread thighs, betraying him with every punishing impact. Richard noticed and reached underneath, giving the thickening shaft one slow, mocking tug.

"Getting hard from your punishment already? Filthy little thing."

The next three strokes came faster--crack-crack-crack--alternating sides, each one harder than the last. Jake's voice cracked on "seven" and "eight," the numbers barely intelligible. His ass was a blazing canvas of overlapping red marks, the skin hot to the touch when Richard ran a rough palm over it.

For the final two, Richard stepped closer, pressing his own clothed erection against Jake's burning cheeks while he spoke directly into his ear.

"These last ones are going to be low. Right where you sit. You're going to feel them for days every time you move."

He pulled back and delivered them mercilessly--one after the other--low enough that the edge of the leather licked against Jake's balls and the sensitive skin just behind them. Jake howled, body jerking hard against the chair, tears pricking at the corners of his eyes.

"Nine... Ten! Fuck--ten, Sir!"

Richard set the paddle aside and stepped in close again, his large hand kneading the punished flesh roughly, spreading the cheeks apart to expose the twitching hole once more. Two thick fingers pushed back inside without preamble, scissoring and stretching the oiled ring while Jake whimpered and pushed back despite the pain.

"Good boy," Richard murmured, voice low and dark with approval. "Now keep that ass up. We're not finished. The paddle was only the warm-up."

He reached for the container of oil again. "Time to see how deep you can really take it."

Richard withdrew his fingers slowly, letting Jake feel every inch drag against his sensitive walls before pulling out completely. The boy's hole winked and fluttered, already puffy and slick from the earlier invasion.

"Stay exactly like that," Richard ordered.

Jake heard slippery noises behind him, but he dared not look around or raise his head off the wicker chair.

Richard coated his girthy cock generously with more oil lube, letting the excess drip obscenely down its length and onto the floor. A clump of grease hung from his ballsack.

Jake's breathing quickened as he heard the wet sounds behind him.

Richard pressed the blunt head against the slick opening and rubbed it up and down, teasing. "You're going to take every inch of this, boy. I want to see exactly how deep you can handle it tonight."

He pushed forward. The fat head popped inside with a wet sound. Jake groaned loudly, his knuckles digging into the chair.

"Relax... breathe," Richard commanded, one hand gripping the boy's hip while the other steadily fed more of the thick shaft in. Inch after inch disappeared into Jake's stretched hole. When he was about halfway, Richard paused, letting the boy adjust to the girth.

"Fuck... it's so thick," Jake whimpered, voice shaky.

"You're doing well. Halfway already." Richard moved slowly, watching the boys rim cling tightly around the invading flesh rod. Then he pushed deeper -- past the curve -- until nearly three-quarters of its length was buried. Jake's thighs trembled violently and a broken moan escaped him.

Richard leaned over his back, lips brushing his ear again. "Deeper, boy."

He applied steady pressure. Jake's body resisted for a moment, then yielded. The last few inches sank in and his cock was fully seated. Jake cried out, a mix of pain and overwhelmed pleasure, his cock now rock-hard and leaking steadily onto the floor beneath the chair.

"Good boy," Richard praised, voice rough with lust. He gave the boy a few short, shallow thrusts, making sure Jake felt the shaft deep inside him.

"Look at that. You took it all. Every fucking inch."

He left it buried for a long moment, one hand reaching underneath to stroke Jake's aching cock in slow, torturous pulls. Every time Jake tried to rock back or adjust, Richard slapped his burning, paddle-reddened ass sharply and slammed his cock deeper into his gut.

"Don't move. Just feel how full you are."

Then Richard began to thrust for real -- long, deliberate strokes that pulled his cock almost all the way out before driving it back in to the hilt. The wet, obscene sounds of oiled manflesh fucking deep into Jake's ass filled the room. Each thrust made the boy's body jolt forward against the chair, his head still pressed down into the seat, ass presented high and helpless.

By the time Richard had worked up to a punishing rhythm, Jake was babbling -- half-formed pleas, moans, and broken "Sirs" spilling from his lips. His hole was stretched obscenely around the girth, flushed dark and glistening.

Richard suddenly pressed all the way in and held there, grinding the cock in small circles so his curved head rubbed relentlessly against Jake's prostate.

"You're going to cum like this, boy. With my cock buried as deep as it can go. And then we'll see if you can take something even bigger."

His hand tightened on Jake's throbbing cock, stroking faster. "Now. Cum for me."

Valerie, on her hands and knees outside of the heavy door, peering in under the threshold, watching her boyfriend be taken by her dad.

She watched as he was made to lick up his cum that had shot to the floor. Jake looked toward the door, on his knees and elbows, slurping up his whitish cum from the hardeood floor. His eyes moved to the door, and his eyes locked onto Valerie's eyes. He froze, immobile and totally embarrassed. His heart pounded in his chest and his ears flooded with the sound of rushing blood.

-----------------------------

Valerie looked to yhe clock on the wall and at ten minutes, she stood and walked to the living room. She was pleased that Amber was there, waiting for her as she had agreed ten minutes earlier.

Val walked over to the coffee table and picked up the heavy wooden hairbrush.

She hefted it in her hands and looked at Amber.

"Last night I told you no masturbation without permission. You played with yourself all night. I could hear you and smell you all night."

Amber blushed as she looked to her feet.

Mindlessly she mumbled "Yes, Ma'am."

She didn't know where that came from; Val had not asked her, she just said it. What Val had said was true. There was no denying any of it.

Valerie pointed to the arm of the leather couch.

"Lift your skirt and drop your panties. Bend over the arm."

Her command was direct, firm, and left no room for disagreement. That time, short as it was, had passed. She was owned property now.

Amber did as she was told. She bent over the firm leather, and rested her head and chest on the seat of the couch. Her feet dangled above the floor, her pale bottom pointing to the ceiling.

She was ready.

So she thought.

-----------------------

The heavy wooden hairbrush felt solid and warm in Valerie's palm as she stepped behind Amber's upturned bottom. The leather couch creaked faintly under the girl's weight, her skirt rucked up around her waist, pink panties tangled around her knees. Amber's smooth, pale cheeks were still faintly marked from the previous night's hand spanking--soft roses on ivory.

"You agreed to the rules, Amber," Valerie said, her voice low and steady, echoing every lecture she'd ever received. "You agreed to my authority. And the very first night, you broke the most important one." She rested the broad back of the brush against Amber's right cheek, letting the cool wood tease her. "No touching that needy little cunt without my permission."

Amber whimpered, shifting her hips. A glistening strand of arousal already clung to her inner thigh. "I'm sorry, Miss Valerie... I couldn't help it. I was so worked up after--"

Crack!

The first stroke landed with a sharp, resounding smack. Amber yelped, her bottom rippling under the impact. A bright oval bloomed instantly on her right cheek.

"You don't get to help yourself," Valerie continued, bringing the brush down again on the left cheek. Crack! "That pussy belongs to me now. Your orgasms belong to me."

Crack! Crack! Crack!

Valerie spanked with steady rhythm, covering every inch of Amber's squirming bottom. The girl's legs kicked, her toes scraping the floor as she tried to twist away. Each solid smack of dense wood on soft flesh echoed through the apartment. Amber's pale skin rapidly deepened from pink to vivid red, then to a hot, angry crimson.

"Ah! Ow! Miss Valerie, please--!"

"You'll take every single one," Valerie scolded, pressing her free hand firmly on the small of Amber's back to keep her in position. "And you'll thank me after. Because this is what happens when you disobey your roommate. When you act like a horny little slut instead of following the rules."

She angled the brush lower, catching the tender undercurve where bottom met thigh. Amber howled, bucking hard. Fresh tears spilled onto the couch cushion. Yet even as she cried, her hips pushed back slightly after each impact, offering her burning cheeks for more.

Valerie smiled darkly, her own pussy throbbing beneath her yoga pants. She could smell Amber's arousal--sweet, musky, unmistakable. The girl's cunt was visibly swollen, lips puffy and slick, clit peeking out as if begging for attention she wasn't allowed to have.

Crack! Crack! Crack!

"Ten more," Valerie announced. "These are for lying there dripping while I punish you. You love this, don't you?"

Amber sobbed but nodded frantically. "Y-yes, Miss Valerie... I do... I'm so wet it hurts..."

The final ten were delivered harder, slower, each one accompanied by a firm lecture about chores, respect, and who was in charge. By the end, Amber's bottom was a blazing, bruised scarlet, marked with overlapping oval prints. She was crying openly but grinding her mound against the arm of the couch in desperate little motions.

Valerie set the brush down and ran her palms over the scorching flesh, squeezing and kneading the punished cheeks until Amber whimpered and moaned in equal measure. She slid two fingers along Amber's soaked slit, gathering the slickness, then pushed them deep inside without warning.

Amber keened, pushing back onto the invading digits.

"You're not cumming," Valerie reminded her, fucking her slowly with two fingers while her thumb brushed lightly over the swollen clit. "Not until I decide you've earned it. Now stand up."

Amber shakily rose, face flushed and tear-streaked, panties still around her ankles. Valerie marched her to the corner, nose to the wall, bright red bottom on full display.

"Hands behind your head. Legs apart. I want that wet cunt visible while you think about your new place in this apartment."

Amber obeyed with a broken little sob. Valerie stepped close, pressing her body against her roommate's back. She reached around and cupped one of Amber's breasts through her shirt, pinching the hard nipple.

"Good girl," she whispered, lips brushing Amber's ear. "You're going to be so well-behaved from now on. And if you're very good... maybe tonight I'll let you lick me while your ass is still this sore."

Valerie left her there and returned to the couch, picking up her phone. She snapped a quick photo of Amber's blazing, displayed bottom--anonymous enough, but clearly well-punished.

Valerie: Sent photo She took her first real hairbrush spanking like such a good little slut. Bottom is glowing. She's dripping down her thighs in the corner right now. I'm soaked too, John. This power feels incredible.

She set the phone aside and watched Amber tremble in the corner, already imagining the long list of rules she would write--and enforce--over the coming days.

Later that afternoon, after releasing a sniffling, obedient Amber to carefully make lunch (standing, of course), Valerie's mind drifted back to her father's house. To Jake. She wondered if he was still feeling the aftereffects of that "talk" with Daddy. The memory of watching through the crack in the door--Jake's face pressed into the chair, ass raised and glistening, taking every thick inch of her father's cock while he sobbed and leaked--sent a fresh pulse of heat through her core.

She wondered if Jake would ever dare touch her again. Or if he now belonged to Daddy too, in some new, filthy way.

Valerie smiled to herself, sipping her coffee while Amber moved gingerly around the kitchen, wincing with every step.

The apartment was going to be very well-run indeed. And Valerie had only just begun.