Chapter 21: Pegging Lessons
The rain had stopped, leaving the alley glistening under the sickly yellow glow of a single, flickering sodium light. Puddles reflected the neon scream of a bar sign two blocks over, bleeding red and blue across wet asphalt. Derek stood just outside the circle of light, his good wool coat damp around the shoulders, his hands buried deep in its pockets. He watched his breath plume in the cold air, each exhale a fleeting ghost. He’d thrown up twice before leaving the house, his stomach empty and raw, but the taste of Jake and Margot still clung to the back of his tongue like a curse.
He walked across to the apartment building. It was a large, converted factory with big glass windows, high ceilings, and a busy lower level with shops, a gym, and a pool off the main lobby. It was clearly a young person's apartment building.
He rode the elevator up to the 12th floor and walked down the hall to unit 1285. Getting his courage up, he knocked on the door. It took a moment before Kayla opened the door. She had already changed from work into tight jeans and a low cut black top that showed off her ample curves. Her hair was down in loose curls and she was barefoot. Derek could hear the light laughter of the other interns coming from inside the apartment while the telltale smell of pot smoke drifted out into the hallway.
Kayla tilted her head, grinning at him with that same cruel cheerfulness she’d shown in the alley. “Hey LDCS. Welcome to our abode.” She stepped back, leaving just enough space for him to squeeze through. “Come on in, Derek. The crowd's all here.”
Kayla moved away from him, leaving the door open for him to follow her. Derek stepped into the apartment and the door clicked shut behind him. He was immediately hit with the sharp smell of weed and the faint aroma of strawberry body spray from Kayla’s perfume. The sounds of laughter and music grew louder as he walked further into the small apartment.
The interior was spacious despite the small square footage. The high ceilings made the apartment feel open and airy. The large windows that made up one wall of the apartment let in plenty of natural light even though it was evening now. The light reflected off the glossy hardwood floors and off the metallic finishes of the modern furniture.
Kathy, Janice, and Sven were all sitting on couches surrounding a coffee table loaded with drinks and a water pipe. They were huddled together, their faces a mix of nervous excitement and giddy anticipation. Next to the couch was a heavy duffle bag.
“Check it out guys. Our little bitch is right on time,” Kayla chirped, her voice echoing too loudly in the confined space. “We appreciate punctuality. Don’t we, guys?” She turned to the others, a cynical smirk twisting her lips.
Everyone clapped.
"Woohoo" Janice wooped.
"Fuck yea, now we can get this party started." Kathy growled.
Sven just nodded, smirking at Derek with a predatory gleam in his eye that made Derek's stomach twist. He recognized that look – it was the same one Margot had given Jake over breakfast that morning.
Janice stood up from the couch, swaying slightly from the weed, and walked over to Derek. She stopped right in front of him, close enough that he could see the dark smudges under her eyes and the way her lips were slightly parted. She reached out and ran a finger down the front of his coat, tracing the damp fabric.
"Aw look," she cooed, her voice thick with inebriation. "He dressed up special for us.
That’s cute." Janice’s fingers trailed over the lapel of his coat, then tugged it slightly, forcing him to take a step forward into the apartment. The movement made the wet fabric drag against his skin, and he shivered at the cold, clinging sensation. The hallway behind him felt suddenly very far away, the door a distant promise of escape—if he even wanted to escape anymore.
Kathy leaned forward from the couch, her beer bottle dangling between her fingers, condensation dripping down the glass onto the carpet. “Did he bring anything?” she asked, her voice sharp with expectation.
Kayla stepped forward, her bare feet silent on the hardwood, and picked up the duffel bag. Kayla unzipped the duffel with a loud, deliberate rasp. She pulled out a collection of leather straps, silicone, and gleaming black plastic. “Alright, ladies. Seminar time. The art of the strap. Theory is great, but practice makes perfect.” She held up a harness, fiddling with the buckles. “Kathy, you’re first. Come here. Let’s get you fitted.”
Kathy stepped forward, a giggle escaping her lips before she bit it back. She was the smallest of the three, with sharp, clever eyes. Kayla helped her step into the harness, tightening straps around her thighs and waist, adjusting the heavy O-ring at the front. Next, Kayla selected a dildo from the bag—a sinister, veined thing of dark purple silicone. She made a show of clicking it into the ring.
“Your tool,” Kayla said, slapping the silicone lightly. It wobbled. “Now, for our demonstration model.” She turned her bright, utterly ruthless gaze on Derek. "Clothes off. Hands and Knees. You know the drill.”
Derek’s body moved before his mind could form a protest. The numbness that had sustained him since sunrise was cracking, replaced by a sharp, prickling dread. He took off his clothes and set them on a chair. He tried not to look anyone in the eye as he stood there naked and exposed in front of the group.
"OMG, what is that thing on his dick?" Janice asked.
"It's a chastity cage." Kayla answered. "His wife keeps his useless dick locked up while she fucks other guys."
"Wow, I can see why she locked it up. It's so tiny." Kathy commented.
The group erupted into laughter.
Kayla clapped her hands, her smile wide and wicked. “Alright, let’s begin. Kathy, take your position. Derek will be your training dummy.”
“Crawl over here,” Kayla instructed, pointing to a spot directly in front of Kathy.
Derek crawled. The posture was the ultimate degradation, more so than kneeling. It reduced him to an animal. He stopped before Kathy, his head bowed. He could see her scuffed sneakers.
Kathy’s grin was all teeth as she dropped to her knees behind Derek, the harness creaking with her movements. Derek felt the cool air hit his bare ass as he knelt on all fours, his hands trembling against the hardwood floor. He closed his eyes, focusing on the weight of the chastity cage, the way it imprisoned him even now.
“Good. Now, Kathy, approach from behind. You want good leverage. Feet shoulder-width apart. Grip his hips.” Kayla was all business, a workshop instructor. Kathy moved uncertainly behind him. Derek felt small hands grip his sides. “Now, line it up. Don’t be shy. Use your free hand to guide it.”
A cold, slippery pressure nudged against him, wrong and invasive. Kathy’s breathing was quick and shallow behind him. “I—I think it’s…”
“Just push,” Kayla encouraged. “It’s not fragile.”
Kathy pushed. There was a brutal, tearing resistance, then a sudden, shocking inward invasion. Derek gasped, a sharp, wet sound. His fingers scrabbled against the wet asphalt. Pain, bright and searing, lanced through him.
“See?” Kayla said, her voice cheerful. “You’re in. Now, establish a rhythm. Short thrusts to start. Get a feel for the mechanics.”
Kathy began to move, her motions jerky and uncoordinated. Each movement was a small agony, a violation that scraped a raw nerve. Derek pressed his forehead to the cold floor, focusing on the texture of the wood. He tried to float away, to disconnect.
Somewhere above him, Janice was laughing, the sound high and wild, and Kayla was saying something about “taking turns” and “making him last.” Then he felt the air shift as Kathy pulled out of him with an obscene wet sound. He didn’t look over his shoulder but he knew what was coming—Janice’s louder, sloppier footsteps, her fingers digging into his hips, her breath hot on the back of his neck. “Goddamn, he’s tight,” she grunted, and then she pushed in, sharp and quick, no warm-up, no mercy. The silicone filled him brutally, and Derek bit down on his own knuckles to keep from screaming.
Janice’s hips slammed against his ass with wet, heavy slaps that echoed through the apartment, each impact jolting another muffled cry from his throat. Kathy watched, her lips parted, her cheeks flushed with something between arousal and discomfort.
Kayla clicked her tongue. “Janice, pace yourself. Don’t treat him like a fucking sledgehammer. You’re not breaking concrete.”
Janice gasped, pulling back slightly even as her thighs trembled. “Shit. Sorry.” But she didn’t stop. Her rhythm smoothed out, awkward but earnest, and Derek felt the pressure deepen, the burn becoming something else—something dangerously close to pleasure, which only deepened his shame.
"Oh, check it out guys. We have an audience." Kayla exclaimed, pointing at the large floor to ceiling window.
Everyone turned toward the window. Across the courtyard from the loft apartment, a group of people were hanging out on their balcony having a party. They had clearly noticed what was going on and were all watching in rapt attention.
A few people were taking videos on their phones, the red recording lights blinking in the dark like malevolent eyes.
"Look at that!" Janice gasped, voice thick with sudden arousal. "They’re watching us! Fuck me, I’m gonna come before too long."
"Good," Kayla said, her voice dripping with approval. "Make him your bitch while they watch. Show them how we train our office pets."
Janice's rhythm lost all pretense of inexperience now. She worked Derek's hole with long, deep strokes that had him whimpering with each thrust.
Each time she pulled back, her fingers dug bruises into his skin, and every time she slammed forward, her pelvis met his ass with a wet, meaty smack that echoed through the room.
"Look at him," Kayla crowed, pacing around them in slow circles like a ringmaster. "Look at how he takes it. Derek’s such a good little slut for his new owners."
Derek couldn’t respond. His mouth hung open, saliva dripping down his chin onto the floor. His legs trembled, his arms shaking as he tried to stay on all fours. His cock, confined in the chastity cage, ached with denied pleasure, swollen and throbbing against the metal bars.
Sven stepped in front of Derek and unzipped his pants. "Let's give them the full show, faggot." he growled, gripping Derek by the hair and pulling him to his hardening cock.
Derek gagged as the familiar salty, earthy taste filled his mouth. He could feel Janice working him harder, her cock pistoning in and out of his ass with brutal precision now. Each thrust forced his throat onto Sven’s cock, making him gag and choke, saliva dripping down his chin, mixing with the tears streaming down his face.
The taste of cum, sweat, and cum-slicked cock filled his mouth as Sven began fucking his face in earnest now, using him like the hole he was. Derek could only whimper around the thick cock in his mouth, his body serving as a fucktoy for all of them.
“That’s it,” Kayla cooed, circling them again. "Pin that bitch!" Kayla crowed as Sven's hips began to piston in earnest.
The room smelled thick now—sweat, silicone, cum. The videos across the courtyard caught every wet slap of Janice's thighs against Derek's ass, every choked gasp around Sven's cock. Derek felt dizzy, his vision tunneling as the three of them used him like furniture with a pulse.
Kayla dropped to her knees beside Janice, leaning in to whisper in Derek's ear, her breath hot and sweet from the strawberry vodka she'd been sipping. "You love this, don’t you? Being nothing but a tight little hole for us to use. You're such a fucking cock slut." Her voice was low, almost husky, and Derek felt a shudder run through him that had nothing to do with the cold. He couldn't deny it—not even to himself. The shame was exquisite, the degradation unbearable yet intoxicating. He whimpered around Sven's cock, his body betraying him completely.
Kayla reached under him, running her fingers down his belly, over his cock cage, brushing his dangling balls as Janice continued to pound his ass. "Cum for us little cock slut." Kayla whispered in his ear. "Cum like a bitch with a dick up your ass and a cock in your mouth." Kayla's voice dripped with cruel encouragement as she whispered these words directly into Derek's ear, her hot breath sending shivers down his spine despite the degrading situation. Her fingers traced circles on his hip, just above the cage, and beneath Janice's merciless thrusts that were now rocking his entire body. Derek could feel his own cock throbbing painfully within the confines of the chastity cage—so close to release but ultimately denied. He moaned around Sven's cock, the vibrations sending another wave of pleasure-pain through his body.
Kayla's hand moved lower, slipping between Janice's thighs and his own shaking body.
She traced the underside of his rigid cock where it pressed against the cold metal bars of the cage, the sensation making Derek's hips jerk involuntarily despite himself. "See how hard you get, little bitch?" she murmured, her fingers circling the base through the confining plastic. "All locked up but still trying to fuck. Who knew a prison would make you so horny?"
Derek's vision swam as Janice's thrusts grew more erratic, her breath coming in ragged gasps behind him.
She was losing control, her movements becoming more desperate, more primal. The wet slapping sounds of their bodies echoed through the apartment, mixing with the sounds of Sven's cock pistoning in and out of his throat with bruising force. Derek could barely breathe, his air supply cut off by the thick shaft filling his mouth. He gagged but there was nowhere to go, no way to escape the relentless assault on all three of his orifices.
Kayla's fingers continued their torment, tracing patterns on his trapped cock, occasionally giving the cage a sharp tug that sent jolts of unexpected pleasure through his body. "Such a needy little slut," she purred, her voice thick with amusement.
"Do you think your wife would be proud of how well you're taking this, Derek? How you're finally being useful for something?"
Derek whimpered around Sven's cock, the vibrations sending another wave of shame through him. The fingers tracing his cock cage gave it a sharp tug, and he couldn't help the involuntary buck of his hips.
Kayla chuckled darkly. "That's it, baby. Let us hear how much you love it. We know you do."
Derek gasped and he felt his orgasm hit like a freight train, squirting his cum through the bars of his cock cage all over the hardwood floor.
Janice's thrusts became erratic, her nails digging into Derek's hips hard enough to leave marks as she neared her own climax. Her breath came in sharp gasps behind him, "I'm gonna- gonna-"
Kayla's fingers tightened around Derek's cage in response, giving it a sharp twist that made his hips jerk involuntarily. "Good girl," she murmured, her voice dripping with approval. "Make him yours while you come."
With a cry that was half laugh, half sob, Janice buried herself deep inside Derek and came with a shuddering gasp, her body trembling against his ass. The sudden fullness of her cock buried inside him as she pulsed against him pushed Derek right to the edge of his own control.
Sven groaned above him, his hips pistoning faster now. The thick cock in Derek’s mouth swelled before jerking violently, hot cum spurting down his throat in thick, salty waves. Derek gagged and choked but Sven held him there, forcing him to take every drop, his grip on Derek’s hair bruising.
"Swallow it all, bitch," Sven growled, his voice rough with satisfaction.
Derek obeyed, his throat working around the cock still lodged in his mouth as he forced down the cum. When Sven finally pulled out with a wet pop, a thick strand of saliva and cum connected his lips to the tip of Sven’s dick for a moment before breaking.
It landed on the floor between them with a soft splat. Derek’s knees trembled violently. He remained on all fours, chest heaving, ass throbbing, his mouth still slightly open and slack with exhaustion.
Kayla stood up slowly from where she had been kneeling beside them. She wiped her chin with the back of her hand and then casually wiped her hand on Derek’s bare ass—leaving a damp streak across his skin. “Perfect,” she said, her voice light and satisfied. “Damn this was fun.”
Behind them, the apartment erupted into laughter and applause, and the sound was echoed from the other balcony across the courtyard.
For a moment, Derek stayed on all fours, unable to move, his breath coming in ragged gasps. His chastity cage was warm and swollen against his skin, the bars pressing into his trapped cock with every involuntary pulse. He could feel the wetness between his legs, cum and spit mixing with the sweat that slicked his thighs.
“Get up bitch. I've got a great idea." Kayla announced. "Let's go out on the balcony and see if anyone wants to come over to play."
Kayla suggested, clapping her hands together like an excited child. She reached out, tugging Derek up by his hair until he was forced to stand, his knees wobbly beneath him. She gave his hair a sharp tug, making him whimper.
Kayla opened the sliding glass door and pulled Derek out on the balcony with her, waving across to the group on the opposing balcony. Janice followed them outside on shaky legs, the thick dildo sticking out obscenely from her jeans, glistening with lube and remnants of shit and blood from Derek's abused ass.
Kathy and Sven stayed inside, passing around the water pipe, laughing like this was just another rowdy night of college shenanigans.
The cool night air hit Derek's naked skin like a slap, making him shudder. He stood there completely naked with his chastity cage dangling for all to see.
Kayla yelled across to the other balcony. "Hey guys, anybody else want a piece of this bitch?" Kayla called out, her voice bright and brash in the quiet night air. The nearby balcony party went quiet for a moment, watching them. Then a few heads leaned in, murmuring among themselves.
One guy with a handlebar mustache leaned over the railing, squinting into the darkness. "We want to watch more. Some of us may join in. Do you guys want to come over to our party? Room 1221."
"We'll come over, but only if at least one of you agrees to let our bitch blow you." Kayla responded.
"Oh shit girl, you are the best." Janice said, laughing.
There was another moment of silence as the group on the other balcony murmured to each other.
Then a tall, lanky guy in a faded band t-shirt spoke up. “I’ll let him suck me off. But only if he does it right here where we can all see.”
"We'll be right over." Kayla promised with a big grin and turned to Derek with a mischievous sparkle in her eyes. "Get dressed bitch. We're going to the party. Leave the cum on your face though. This will be hilarious."
Kayla giggled, clapping her hands together like an excited child. There was still a rogue drip of cum sliding down Derek's chin, and she wiped it away with a playful flick of her finger, leaving a streak across his cheek. "This is going to be so much fun!"
Derek nodded, his body still trembling from the ordeal, and began gathering his clothes again. The laughter from the other balcony had resumed, more boisterous now, and as he dressed, he couldn't help but notice the appreciative eyes on him. He wasn't entirely sure if they were watching him dress or watching him leave a trail of cum on his own collar.
Derek pulled his shirt over his head before he could think about it too much. The fabric stuck slightly where it brushed against his damp skin. He found his shoes by the front door and slipped them on, the laces dangling untied. The apartment buzzed with laughter and the occasional shout from inside, the water pipe making its rounds. He paused at the door, his hand on the knob.
Kayla appeared beside him, suddenly close enough that he could smell the strawberry vodka on her breath again. "You're not gonna bail on us, are you LDCS?" she asked, her voice playful but with an edge. Her fingers traced the outline of the chastity cage through his pants.
Janice, Kathy, and Sven had packed the toys back into the duffle bag and put on their shoes and met them at the door. They headed out of the apartment in a group, their laughter bouncing off the hallway walls and Derek walking silently between them, the cum still dripping off his face.
The elevator ride down was a blur of Kayla pressing impatiently on the lobby button while Sven leaned against the mirrored wall, smirking at Derek’s reflection. The doors slid open with a soft ding, and they spilled out into the bustling lobby with its neon signs and hum of conversation.
Derek tried to keep his head down, but noticed the strange stares from some of the people they passed, probably guessing at what was all over his face.
The walk to the next building was short but felt endless. Derek’s shoes squeaked slightly on the wet pavement, the sound mingling with the distant bass of a bass-heavy playlist coming from one of the building’s open windows. Across the street, the party on the other balcony had grown louder, the silhouettes of bodies moving rhythmically beneath the flickering lights of the courtyard.
The mustached guy—who introduced himself as Rico—was still leaning over the railing, his dark eyes gleaming as he watched their approach. A red Solo cup dangled from his fingers, condensation dripping onto the metal railing below.
“Come on up guys,” Rico said, grinning at Derek with slow appreciation. “Everyone is excited to meet you.” He took a long sip from his cup, the liquid leaving a faint stain on his mustache.
Kayla stepped forward, her posture all business despite the playful nature of her earlier comments. “We brought a gift,” she announced, gesturing toward Derek with a flourish. “He’s been trained."