Chapter 5: The Breakfast Tease
The low ache in Mike’s ass started as soon as he stirred the next morning. Not pain, exactly, but a deep, persistent awareness, a throbbing echo of the dildo, the fingers, Trent’s relentless mouth. It felt empty, stretched, and demanding. He shifted, the familiar leather of his bedside chair groaning under his weight as he pulled on fresh socks. The memory of Trent’s whispered command – "Ready by 5" – sent a fresh jolt through his groin. But 5 PM felt like an eternity. He needed relief now.
He padded towards the ensuite, then paused. Maria’s vanity. The bottom drawer, rarely touched. Old makeup, dried-up lotions and tucked beneath a silk scarf, a small, discreet box. Inside, nestled in velvet, lay Maria’s modest silicone dildo – smooth, purple, about the length of his hand. He’d bought it for her years ago, forgotten. Now, it looked like salvation.
Back in the bedroom, door locked, pants around his ankles, Mike leaned back against the wall. He grabbed the lube he sometimes used to jerk off with and wetted the tip hastily. He smeared it, moving his coated fingers down to his hole. As he rubbed the liquid into his ass he let out a deep groan. Even that felt so good. He positioned the toy and pressed it to his still-loose hole. It slipped in easier than he expected, the familiar stretch a balm to the demanding ache inside. He worked it slowly, shallowly at first, then deeper, chasing the pressure against his prostate. A few minutes of focused rocking, and the tight coil in his gut released. He groaned softly, head thumping against the wall, as the immediate, gnawing need subsided. Relief, sweet and simple. He pulled the slick toy out, noticing the precum stretching from the tip of his cock to his clean work pants. He gathered as much as he could on his hand and licked it clean, kick his pants to one side and went to the bathroom to clean everything up. Once redressed, he saw the toy sitting on the side and dropped it into his work bag. Insurance.
Work was a blur of spreadsheets and muted desire. The ache returned, a low hum beneath his concentration. During a mid-morning lull, Mike grabbed his bag and slipped into the large, rarely used restroom on the third floor. Locked in a stall, pants down, he retrieved the dildo. He worked it in quickly this time, the silicone sliding home. The fullness soothed the hunger instantly. Riding a wave of reckless abandon, he pulled out his phone. He angled it down, capturing the obscene image: his hairy thighs spread, his hand gripping the base of the purple dildo buried deep in his ass, a slick sheen visible around the stretched, puffy rim. He sent it to Trent with a single word: Needy.
The response was almost instantaneous. A photo flooded his screen. Trent, standing at a public urinal, sweatpants pulled down just enough. His massive, thick cock hung heavy, the swollen purple head glistening with a thick bead of precum, poised to drip onto the porcelain. Below it, a text: Starving. Stay hungry. Mike shoved the phone away, slamming himself back onto the dildo with a choked gasp, the visual of Trent’s cock searing into his brain, amplifying his own desperate rocking until his ass shuddered through a quick, messy release onto the stall floor. He pulled the toy to his lips and licked the ass cream from it, wiping the rest from the floor with toilet paper. That was getting easier to achieve as he practiced. It was like learning to wank all over again, but at 47.
He made it home just as Maria was grabbing her keys by the front door. "Mike! Perfect timing," she smiled, adjusting her scarf. "Off now to meet up with the girls. The details are on the fridge, the cottage address, the landlords details. I won't text much as we'll be busy, but you have Trent." Her eyes, sharp but kind, scanned his face. "You look… good. Relaxed. Trent’s good for you."
Mike flushed, adjusting the strap of his bag, acutely aware of the damp, used dildo inside it. "Yeah. Yeah, it’s… it’s been good. We’re getting along. Both learning a lot about each other. And ourselves. All that"
A knowing, slightly mocking smile touched her lips. "Getting along? Mike, darling, you're practically glowing. You're falling in love with that boy."
The bluntness stunned him. He met her gaze, the truth of it undeniable, terrifying, and exhilarating. He couldn't lie. Not really. He shrugged, a small, almost shy smile breaking through. "I can't disagree."
Maria laughed softly, a warm, rich sound. She leaned in, kissed his cheek. "Good for you. Honestly? I wouldn't blame you if you did hook up with him." She winked, then turned, pulling the door open. "Life's short. Have fun." The door clicked shut behind her, her words echoing in the sudden quiet of the hallway. I wouldn't blame you... he couldn't deal with it now. Not with his time with Trent so close.
Ready by 5. Trent’s command pulsed in his veins. He’d taken a half-day, the afternoon stretching before him. He cleaned up meticulously in the shower, paying special attention to his tender hole. It felt different now – used, open, belonging. The soreness was minimal, a testament to Trent’s brutal expertise. He dried off, the towel catching on the roughened skin around his rim. Remembering the notification, he went to the front porch. An Amazon box. Trent’s name, but the message had said it was ‘for him to swallow’. He tore it open.
Inside: not sex toys. Bottles. Zinc. Pygeum. L-Arginine. Sunflower Lecithin. Selenium. He recognized them – supplements Trent had mentioned offhand, bragging about monstrous loads and more stamina. Good for him to swallow. Understanding dawned, filthy and thrilling. Trent wanted him at his peak. Plentiful. Underneath the bottles, in it's own sealed package was a white jockstrap. Thick cotton, wide waistband, practical. Exactly like the ones he’d worn under his rugby kit decades ago. A stark contrast to the delicate lace Trent had adorned him with before. This felt… functional. Athletic. Primal. He changed into it immediately. The familiar, snug support felt grounding, yet charged with new meaning. His cock filled the pouch comfortably.
He descended the basement stairs, heart pounding. The familiar scent – dust, old paper, Trent’s sweat, weed – wrapped around him. The scene that greeted him was unexpected. Trent stood near the full-length mirror, shirtless in his usual sweatpants. God he looked good in them. Around the mirror, three cameras on sturdy tripods were positioned at different angles, their red recording lights blinking ominously. On the floor directly in front of the mirror lay a thick exercise mat, covered by a large, dark blue bath towel. Next to the mirror was a monitor on an extendable arm.
Next to the mirror was a monitor on an extendable arm. Mike froze on the bottom step, his gaze snapping from the cameras to Trent. Panic, cold and sharp, cut through his arousal like a razor. "What the fuck is all this, Trent? Cameras? You filming?" His voice sounded strained, too loud in the quiet basement. "Are you out of your goddamn mind? What if someone hacks this shit? Finds it? My face? My fucking asshole plastered online?" The potential fallout – Maria, his job, the sheer, crushing humiliation – crashed over him. "That’s insane. Absolutely not."
Trent didn't flinch, his expression calm, almost amused. "Chill, daddy," he said, his voice a low rumble. "I get it. Scary shit." He walked towards the closest camera, his movements deliberate. "C'mere." He beckoned Mike closer, his tone brooking no argument. Reluctantly, Mike stepped forward, his heart hammering against his ribs. Trent grabbed Mike’s shoulder firmly, pulling him directly in front of the lens. His other hand flipped a switch on the side of the monitor arm. The screen flickered to life.
Mike stared. On the monitor, their bodies were clear: Trent's powerful frame, Mike's hairy torso in the white jockstrap. But their faces were completely obscured by a shifting, swirling digital blur. He watched Trent's blurred head turn towards him on the screen. "See?" Trent said, his voice disembodied from the blurred face. "Faces? Gone. Any tattoos, scars, birthmarks – anything that could ID us? Poof." He tapped the monitor casing. "New tech, man. Top shelf. Encrypted uploads, anonymous cloud storage. Secure as fuck. Nobody's seeing our mugs." He looked at Mike, the blurred image somehow conveying his intensity. "But you need to see. That's the step. Not just feeling it. Seeing it. Seeing what I do to you."
Mike exhaled shakily, the sharp edge of his fear dulling slightly under Trent’s certainty and the undeniable evidence on the screen. The blur worked. It was still insane, reckless, but… contained. The image of his own blurred body was strangely arousing. "Okay," Mike muttered, the word thick. "Okay. But… fuck." Trent clapped him on the shoulder. "Relax first. Smoke." He steered Mike towards the sectional, grabbing a fat pre-roll and lighting it. They passed it silently for a few minutes, the familiar warmth spreading through Mike’s limbs, loosening the tension coiled in his neck and shoulders.
"Got your pic today," Trent said, taking a deep drag. "Stall looked cozy. That purple dick treating you right?" He smirked, blowing smoke towards the ceiling.
Mike flushed, remembering the frantic bathroom stall, the desperate relief. "It… did the job," he admitted gruffly. "Felt empty after last night. Needed filling."
"How's that sweet hole feelin' now? Sore? Open? Just… hungry?" Trent asked, his eyes darkening as they roamed Mike's body.
"Hungry," Mike confirmed instantly, the truth a low thrum in his belly. "Feels… different. Open. Soft, almost. Like it’s waiting." The weed made the confession easier, smoothing the edges.
"Good," Trent purred. He stubbed out the joint. "Time to see what you're waiting for." He stood, his presence suddenly filling the room again. He held out his hand. Mike took it, letting Trent pull him to his feet and lead him towards the mat laid before the mirror. Trent gestured. "Down. On your back. Head here." He pointed to a dark, sturdy foam block positioned at one end of the mat. Mike lay down, the thick towel soft beneath him. He settled his head on the block, his body angled slightly upwards, his legs falling open naturally. His ass was perfectly positioned towards the mirror. Trent knelt between his spread thighs.
"Look," Trent commanded softly, his gaze fixed on Mike’s exposed hole. Mike turned his head, craning to see the reflection. Trent reached down, his thumbs gently parting Mike’s ass cheeks further. Mike stared. The tight, neat hole he’d known for nearly five decades was gone. In its place was a soft, swollen mound of pink flesh, glistening slightly with lube residue. The rim was thick, puffy, protruding slightly like engorged lips. It looked… open. Vulnerable. Used. "Jesus," Mike breathed, shocked. "That’s… that’s mine?"
"All yours, baby," Trent murmured. "Look at that beautiful, fat pussy you grew for me." He traced a fingertip lightly, feather-soft, around the outer edge of the swollen rim. Mike felt the touch as a delicate spark, a whisper against nerve endings he hadn't known existed. He watched in the mirror as his own hole seemed to pulse faintly under Trent's touch. Trent continued, stroking the puffy skin, circling, never penetrating, just exploring the transformed landscape with a possessive reverence. "So soft," Trent breathed. "So fucking wet for it already." Mike felt the connection snap into place – the delicate, almost ticklish sensation radiating from his ass directly linked to the obscenely plump, glistening slit he saw reflected. It wasn't just his ass anymore; it was a needy, sensitive thing Trent had cultivated. "Oh fuck," Mike whispered, arousal flooding him, his cock straining against the cotton jock pouch.
Trent picked up a remote. "Lights, camera," he muttered, pressing buttons. The basement lights dimmed slightly, leaving the area around the mat bathed in a focused, soft glow. The cameras’ red lights blinked steadily. He pulled the monitor on its arm closer, positioning it directly above Mike's head, angled so Mike could see the screen without straining. He tapped the screen. "Watch."
On the monitor, Mike saw a close-up, high-definition view of his own swollen, pink hole. The detail was shocking: the crinkled texture of the puffy rim, the slight sheen of natural slickness already gathering, the darker pink inner folds just visible. Then Trent’s face filled part of the frame. He leaned in, his lips puckered, and placed a soft, deliberate kiss right on the center of Mike’s hole. Mike gasped, both feeling the warm pressure and seeing it magnified on the screen. Trent kissed again, slowly, wetly, his lips lingering, then he began to lick. Broad, flat strokes of his tongue swept over the entire swollen area, coating it in spit. Mike watched, mesmerized, as his hole visibly quivered under each pass, the flesh darkening, becoming slicker. Trent pressed his face deeper, his tongue stiffening, and began fucking the hole shallowly with just the tip, the obscene slurping sound loud in the quiet room, perfectly synced with the image on the screen. "Oh god, Trent," Mike moaned, his hips twitching upwards.
Trent pulled back slightly, gathering a mouthful of spit. He let it drip thickly from his lips onto the glistening hole, the glob landing with a wet splat that Mike both felt and saw on the monitor. Then Trent dove back in, sucking hard, pulling the entire puffy mound into his mouth. Mike felt the incredible pressure, the vacuum, saw his flesh being drawn tightly between Trent’s lips. Trent released with a pop, spit and Mike’s own slick forming viscous strings. He sucked again, harder, rhythmically, slurping deep, then pulled off, the swollen rim glistening obscenely. "Tastes like heaven," Trent groaned, spitting another heavy glob directly onto the center before swirling his tongue around the stretched opening, gathering the mixed fluids and swallowing. He repeated the cycle: kissing, licking sloppily, spitting, sucking hard, slurping – turning Mike’s ass into a glistening, spit-slick mess. Mike was transfixed by the visual spectacle on the monitor – the intimate, raw close-up of his own body part being worshipped and savaged simultaneously. His cock was leaking steadily inside the jockstrap, a damp patch spreading.
"Remember yesterday?" Trent rasped, pulling his mouth away. His fingers, slick with spit, found the puffy rim. "Gape for me, baby. Open that pretty hole up wide. Show me how hungry you are." Mike remembered the incredible sensation, the stretch. He took a deep breath, focused, and bore down, pushing out with muscles deep inside. On the monitor, Mike watched, awestruck, as his swollen, spit-slicked hole began to open. Slowly, tremblingly, the thick pink folds parted like a flower blooming in fast motion. The dark, moist inner tunnel was revealed, clenching rhythmically around nothing. Trent blew a sharp puff of cool air directly into the gaping hole. Mike felt it rush inside, a shocking, intimate intrusion, and saw his hole flutter wildly on the screen. "Fuck yeah," Trent growled, mesmerized. He traced the very edge of the dilated rim with a single fingertip, the touch feather-light but electrifying against the hypersensitive, stretched flesh. "Look at your hungry cunt, Mike. Begging to be fucked."
The combination detonated him. The visual – his own hole gaping obscenely wide on the monitor, vulnerable and slick. The physical – the puff of air deep inside, the impossibly delicate tracing on his stretched rim. The knowledge Trent had done this, made this. A raw, guttural shout tore from Mike’s throat, completely beyond his control. His back arched violently off the mat as his cock erupted untouched inside the jockstrap. Thick jets of cum pulsed, soaking the cotton pouch immediately, warmth spreading as he convulsed, his gaping hole spasming wildly around nothing but cool air, captured perfectly on the monitor above him. "UUUNNGGHH! FUCK! TRENT! OH GOD!" The orgasm ripped through him, relentless, powered by the sheer visual and sensory overload. He couldn’t shut his eyes; he stared, dazed, at the screen showing his own ruined hole still quivering, dripping spit and lube, as wave after wave of pleasure crashed over him. He collapsed back, panting, utterly spent, the monitor still displaying the aftermath of his surrender. Trent just watched the screen, a dark, satisfied smile spreading across his face.
Mike lay utterly spent, limbs loose, chest heaving, his white jockstrap soaked dark. The monitor’s harsh light still displayed the aftermath: Mike’s gaping, spit-slick hole clenching rhythmically on nothing, a glistening pink portal nestled in his hairy ass. The air hung thick with the scent of sex, weed, and lube. Trent chuckled low, a rumble of pure dominance. "Fuck, pussyboy. You painted that pouch good." He reached down, his thumb finding Mike’s swollen rim, tracing the puffy edges. Mike flinched, oversensitive, a weak groan escaping him.
"Easy, tiger," Trent murmured, his touch turning unexpectedly gentle. "Just admiring the work." He glanced at the monitor, a thoughtful look replacing the predatory grin. "Gotta take care of this masterpiece." His fingers, slick with Mike’s own juices from the rim, slid up, pressing firmly into the yielding muscle just behind Mike’s balls, working the tense perineum. Mike sighed, the unexpected pressure both grounding and deeply relieving the trembling aftershocks. Trent kept massaging, strong thumbs working the tight spots along Mike’s inner thighs, his touch shifting from claiming to caring. Mike felt himself drifting, exhaustion and residual pleasure pulling him under.
He jolted awake to a startling sensation. Solid. Cold. Pressure blooming low inside him. Mike opened heavy eyelids, blinking in the dimmed basement light. He tilted his head down, peering between his legs. Trent knelt there, slowly pushing a smooth, cold silver metal sphere, slightly larger than a golf ball, deep into Mike’s slicked, open hole. It slid in with surprising ease thanks to the lube and Mike’s stretched state, disappearing completely. It left behind only a flat, circular base flush against his skin, adorned with a single dark, glittering blue stone in its centre. The cold metal inside him contrasted sharply with his heated core.
"Easy, easy," Trent soothed, patting Mike’s flank. "Just a little friend. Helps with that needy ache, stops too much tightening." He gave the jewelled base a light, proprietary tap. "Suits you." Mike shifted. The plug was an undeniable presence, thick and unyielding, a constant reminder filling the emptiness. Oddly, it wasn’t painful; the ache did recede, replaced by this solid, cool fullness. Trent helped him sit up, the plug shifting inside him, a firm pressure against his prostate that made him gasp softly. "C’mon, big guy. Over here." Trent guided him by the elbow towards the back of the basement, behind the large sectional couch.
Mike blinked. A sturdy, professional-looking massage table stood there, draped in a thick, soft white towel. He hadn’t noticed it before amidst the camera setup. "Hop up. Face down. Head in the hole." Trent’s voice was calm, directive. Mike obeyed, climbing onto the padded surface, resting his face in the cushioned ring. The position was comfortable, the plug settling deep as he relaxed onto his belly. Trent moved to the head of the table. Mike heard a bottle open, then felt a stream of gloriously warm oil drizzle onto his lower back. The scent of eucalyptus and almond filled his nostrils. Strong, skilled hands began working the oil into his shoulders.
Trent, Mike remembered belatedly, was a trainee physiotherapist. This wasn’t foreplay. This was treatment. The hands were expert, finding knots Mike hadn’t known existed in his traps, his rhomboids, down the length of his spine. The pressure was firm, therapeutic, working out deep-seated tension carried from years of rugby and desk work. Trent worked methodically down Mike’s back, over his flanks, to his powerful glutes. He spent significant time here, working the dense muscle with deep, gliding strokes and targeted pressure. Then his thumbs found the area around the plug’s base. The touch was clinical, precise. Trent carefully gripped the jewelled base, twisted it slightly, and pulled the cold metal sphere slowly out. Mike felt the stretch of its widest point passing his rim, then the sudden cool air. Trent’s oiled fingers immediately massaged the puffy rim itself, applying gentle pressure, stretching it slightly, then soothing with circular motions. He added more warm oil directly to the sensitive opening, his touch nourishing the strained tissue. Mike groaned, the sensation utterly different from Trent’s usual ministrations – healing, not claiming. After several minutes of this focused attention, Trent re-lubed the plug and slowly, firmly, pressed it back home, the metal coolness returning to Mike’s core. He gave the base another pat. "Good boy."
Trent moved down to Mike’s legs, working the hamstrings and calves with the same focused intensity. Time became fluid under the expert hands and the warmth of the oil. Eventually, Trent nudged him. "Flip." Mike turned over onto his back, the plug a solid anchor within him. Trent began again on his chest, shoulders, down his arms, working the pectorals that still bore the faint impression of lace from the night before. His hands moved lower, over Mike’s hairy belly. They brushed Mike’s cock, resting flaccid against his thigh in the soaked jockstrap. The touch was incidental, professional. Despite the exhaustion and the therapeutic context, Mike’s body responded instinctively, his cock giving a faint twitch, plumping slightly. Trent noticed but didn’t linger, his hands moving past to work Mike’s quadriceps. There was no sexual charge in his touch now; his focus was entirely on the muscles, releasing tension. He finished with Mike’s feet, a surprisingly blissful pressure on each arch. "Alright," Trent said, his voice low. "Relax now. Stay put." He draped another thick towel over Mike’s front. "Twenty minutes." He turned off the bright light directly above the table, leaving Mike in soothing semi-darkness.
The rhythmic kneading, the warmth, the profound relief in his muscles, and the strange comfort of the plug lulled Mike into a deep, dreamless doze. He surfaced slowly, the basement quiet except for the low hum of electronics. Pushing himself up on his elbows, he saw Trent. The cameras were packed away. Trent sat on the couch, laptop open on his knees, phone in hand. He was scrolling intently. As Mike’s eyes focused, he saw the images on Trent’s phone screen: close-ups of men’s gaping, used assholes, stretched wide, some dripping cream. A familiar, possessive pang shot through Mike. He swung his legs over the side of the table, the plug shifting inside him, a reminder. "Should I be jealous?" Mike joked, his voice still rough with sleep, nodding towards Trent’s phone.
Trent looked up, a slow smirk spreading. He turned the phone slightly, flashing another graphic image of a cavernous, glistening hole. "Got nothin’ on you, pussboy," he said, his tone amused but firm. "This amateur hour shit." He locked the phone, tossing it aside. "How’s the equipment?" Mike stood, the plug’s presence suddenly more pronounced. He shifted his weight. It felt surprisingly solid, anchoring, a constant low-level fullness that soothed rather than aroused. "Surprising," Mike admitted. "But... yeah. Calming. Didn’t know it could feel like that." He glanced at the digital clock on Trent’s laptop: 8:07 PM.
"Good," Trent said, closing the laptop. He stretched, muscles rippling. "Shower. Get dressed. We’re getting food. Keep it light, clean." He winked. "Gotta keep that sweet hole prepped for later. No spicy bullshit clogging up my playground." He grabbed Mike’s discarded clothes, tossing them towards him. "Move it, stepdaddy. I’m fucking starving." The promise in his voice, the casual ownership, sent a fresh, warm shiver through Mike, the plug a silent accomplice nestled deep within him.