Miles
The day came to pass, and Miles got ready to go to Jordan’s.
The black turtle neck and black pants he chose for the occasion made him look leaner, and his polished dark shoes taller. No one could have guessed he was heading toward a humiliating night, because dinner would probably end in some twisted sexual game.
Miles sauntered to his doom without fear; there were only a few days left to his captivity, and nothing Jordan could do would change the fact that he’d get back at him, one way or another.
He knocked on his tormentor’s door, shivering from the cold that seeped into his bones, even though he was wearing a thick leather jacket and woolly gloves.
As Jordan appeared in the doorway, wearing plain jeans and a white tank top, Miles bowed his head in reverence.
“Hello, sir.”
He might as well keep up appearances to the end.
“Hi, boy,” Jordan replied with a smirk, his cock already bulging through his pants. “You want a drink?”
“A beer will do, sir, thank you.”
Miles was authorized to sit with a simple nod, and he wasn’t even asked to strip, which was new. If he hadn’t known any better, he’d have thought Jordan was half-decent.
He sipped his beer while Jordan seasoned their food before stuffing everything, roast beef and potatoes, in the oven. It looked like they wouldn’t starve tonight, but Miles would’ve liked to be anywhere else but here. The couch was comfortable, the apartment luxurious with its exposed beams and expensive furniture, but he didn’t feel at ease. The feeling of his locked cock constantly reminded him that Jordan was nothing more than a manipulative bastard, and he wasn’t even subtle about it.
Jordan’s broad shoulders rolled as he cleaned the utensils he had used, and then he sat next to Miles, smelling of cologne and aftershave. Jordan’s nipples were hard, and the look he gave Miles from under his long lashes suggested he was ready for a bit of fun. So, Miles sank to the floor, leaving his beer to warm on the coffee table.
“You look gorgeous tonight, you should dress like that more often,” Jordan commented, stroking Miles’s hair, almost lovingly.
“Thanks, sir.”
Miles wandered back to Austin. The guy wouldn’t be the love of his life, but he had been more mindful than Jordan had ever been, and the pounding Miles had received from him had turned out to be more than decent. What had been less ideal was how foul the bathroom was, and how painful Miles’s attempts at getting hard were.
And the sense of normalcy Jordan was intent on faking right now was unnerving at best, a travesty of what their relationship should’ve been from the beginning.
All it did was anger Miles further, but he kept a straight face, and after unzipping Jordan’s pants and freeing his cock, Miles wrapped his lips around his length.
The taste of precum was salty on his tongue, and more came out as he sucked on it. For once, Jordan didn’t force his head down; he didn’t hold him in place to make him choke. Miles was allowed to go at his own pace, working on the cock he was taught to worship without external interference. The whole experience was pleasant, in a way, and Jordan’s moans had Miles aroused and leaking through his chastity cage.
Fuck me, this guy ruined me.
For real.
He cupped Jordan’s balls, pulling on them gently even if he wished he could beat them black and blue. Instead, he kept on sucking until Jordan was panting and thrusting into his mouth.
“Your mouth’s the best,” Jordan said, pushing a thumb in Miles’s mouth. “Strip for me, take your time. I want to enjoy the show.”
Miles did as he was told and seductively rose to his feet, touching himself, pinching his nipples through the fabric of his clothes, groping his caged cock, and letting his hips sway like a bitch in heat. His hole was still sore from yesterday, and he hoped that Jordan wouldn’t notice he had been opened by someone else, somehow.
The punishment for this would surely have him begging for mercy.
“Fuck yeah,” Jordan whispered, watching Miles throw his turtleneck in his direction.
Jordan caught it and sniffed it, eyes rolled back, his cock throbbing bigger, cockhead half covered by his foreskin.
To Miles, this would’ve been extremely hot if it hadn’t been for the fact that he hated Jordan with a passion. What he loved about him, however, was his handsome face, body, and beautiful cock. He couldn’t deny it; he loved the smell of this dick after a day of work, and if its owner had been a decent human being, then Miles would’ve gladly submitted to him willingly.
Maybe not at first, but eventually.
Miles kicked off his shoes and removed his socks.
Would I have? He asked himself as he let his pants drop to his ankles.
“How’s that cock feeling?”
“I,” Miles swallowed, tugging at the elastic band of his black boxer briefs. “I wanna cum so bad, master.”
“We got the whole night ahead of us. Who knows, I might let you cum multiple times.” Jordan stroked his meat, winking at Miles.
“I’m only here to serve you, sir,” Miles replied, discarding the last of his clothes.
Now naked, he stood in front of Jordan without shame. He knew everything about him after all, there was no need to be ashamed, no need to blush, no need to hide. The precum oozing out of his slit was the most humiliating thing; it showed the situation turned him on, that his status as an owned slave was somewhat impacting him positively.
Miles wanted to grab his own dick, jerk it like a madman until he shot his load all over the place, to sully Jordan’s face with his cum and slap his dick across it before sticking two fingers in his manhole. This made Miles’s cock jump, and that’s when he knew not everything was lost.
Breaking him would take longer than a couple of weeks, and he’d get out of this free and stronger.
Gayer too…
But he had made his peace with that, only he’d be gayer on his own terms.
“Get over here,” Jordan ordered. “Spread your legs and finger yourself for me.”
Miles obeyed, choosing to sit on the floor, his back propped against the coffee table and his legs up on the couch on either side of Jordan. He spat on his fingers, sucked on them, and stuck a knuckle in his hole. It was sensitive; it had been overused lately. He winced and pushed a second finger into it, biting his lower lip as he stared deep into Jordan’s eyes.
“Good slut,” Jordan said, wanking his cock slowly. “You’re gonna fuck yourself on that dick?”
Miles nodded.
“What are you gonna do, slave?”
“I’m gonna fuck myself on your cock, sir!” Miles answered, stretching his hole with a third finger. “Fuck…”
“Good fuckin’ boy.”
A shiver ran through Miles’s body, and his chastity cage twitched. The insults had been oddly gentle; there was no meanness behind them, and Jordan looked down at him with a gentleness Miles didn’t know he was capable of. This dance was well planned, and Miles was playing his part beautifully. He relaxed, ready to take Jordan. If he earned his trust and made him believe there might be a chance he might stay once their bet reached its end, then his betrayal would hit harder.
Maybe it’d even teach Jordan a lesson in humility and basic human decency.
“I’m ready, master. Can I sit on your cock, please?” Miles pleaded, faking his eagerness.
“Don’t stop until I fill you up, boy!” Jordan instructed, lubing his cock with saliva.
Miles hopped into Jordan’s lap, balancing himself to align his entrance with his dick. He held onto Jordan, staring into his eyes as he let his cockhead slip into his hole smoothly. Miles stopped moving, clenching around Jordan’s glans but not allowing him to go any further. There was a silent plea in his captor’s eyes, a hint of submission, and a yearning for more. Miles throbbed in his cage; that’s where he wanted Jordan, right on the brink of losing his shit.
But he didn’t, he didn’t hump, only frowned and licked his lips as he tried to anticipate what would happen next.
Miles slammed down, burying Jordan’s cock deep inside his hole in a single thrust. His balls slapped against his ass once, and then he stopped moving again, squeezing his entire length until it was almost painful. Miles fucked himself leisurely, his hands wrapped around Jordan’s throat like a collar.
He felt powerful in that moment, though he knew he could only do that because Jordan allowed it.
That’s how it should be.
Fuck, his cock feels so good.
The pace was torturous for Jordan, whose first instinct would’ve been to plow Miles until he was begging for mercy.
Right now, Miles was driving, and he found he enjoyed sex a million times more when he was in control of what would happen. There was no doubt Jordan would turn the tables at some point, but in that instant, Miles allowed his mind to go blank.
When it wasn’t forced, Miles quite enjoyed having Jordan inside him, and he looked all the more attractive as he complied.
His dark skin glistened with sweat, and the smell of it drove Miles to new heights, taking over his senses. He leaked, precum dripping on Jordan’s belly.
As a test, Miles dipped his fingers into the little puddle and brought them to Jordan’s parted lips, who stuck out his tongue without being asked to, licking off the precum he was offered.
“You like how I taste?” Miles asked, picking up the pace.
“Shit,” Jordan shut his eyes. “Yeah, I do, so much.”
“You wanna cum inside me?” Miles clenched his asshole, causing Jordan to pant harder. “You wanna breed me, sir?”
Jordan stayed silent, his Adam’s apple bobbing up and down as he swallowed, breathing through his nose and exhaling through his mouth. Miles grabbed his top’s balls, feeling them tighten as he rode him harder. He was sweating too now, unable to contain his moaning. His prostate was on fire, and his dick was pressing into its prison and leaking more and more.
He was nearing his orgasm.
“I’m getting close, too, sir. Can I cum?”
“Yeah, whenever you like,” Jordan panted, lost in his own pleasure.
Suddenly, he grabbed Miles’s hips and began fucking him mercilessly, first in the same position and then with Miles pinned chest-first into the couch. He couldn’t move; he was trapped, and Jordan took full advantage of his vulnerability. His cock was angled in such a way that it felt bigger, and as he drilled into Miles, he bit his neck, not too hard, but enough to burn and leave a mark.
He marked me, the fucking bastard, like a fucking animal. Miles resentfully thought, doing his best to handle the fucking without crying out.
There was pleasure to it, too, but his lack of trust in Jordan kept him from enjoying the moment. Yet, the relentless beating of his prostate brought him to the edge.
“I’m cumming, sir, I think I’m cumming!”
“Go on, boy,” Jordan rammed into him. “Fucking cum for me.”
Miles released his seed, hands-free, untouched like the good sub boy Jordan wanted him to be. Jordan removed his cock and scooped some of Miles’s own cum, applying it to his cock before thrusting back into him.
Soon, Jordan’s movements became more erratic, ragged, and without warning, he flooded Miles with long ropes of cum. Miles had his head buried in the cushions, and he felt each spurt fill him progressively until he was full.
Jordan held him in place, kissing his back as if they’d shared a tender moment.
The pleasure had been there, but there was no love, no trust.
“Keep my cum inside.”
The emptiness that followed as Jordan left disgusted Miles, not because he had totally hated what had happened, but because he hated the feeling of his gaping hole craving more.
He just wished Jordan wasn’t such an asshole; otherwise, he’d have loved every second of their time together.
Fuck no, stop this! Miles scolded himself.
Sure, the dick was nice, but that wasn’t enough.
When Jordan came back, he had a massive dildo in one hand and the chastity cage’s key in the other, and a devious smile on his face.
“This is nine inches. Think you can wear it for the evening?”
“Sir, I…”
“If you can, I’ll free your cock for the evening, too… If you can’t, well…”
His words hung in the air. If Miles couldn’t take the dildo, he wouldn’t get unlocked. He just wanted some freedom, to feel his cock throb without constraints.
“I can take it, sir,” he agreed begrudgingly.
“Good boy, I knew you’d make the right choice,” Jordan sniffed the air and threw the dildo and the key to Miles. “Fuck, the oven!”
The flavor of roasted meat was thick and salivating in the air, and Miles couldn’t believe they hadn’t noticed the smell, but fortunately, it hadn’t burned to a crisp.
He was left to uncage his dick and plug his hole.
The dildo was a tight squeeze, but his loose asshole swallowed it with barely any protest. There was a little pain when it inched in, as he wasn’t used to taking anything this big. But he’d get used to it, he told himself.
When his cock was freed, it sprang to life instantly, and the urge to stroke it was overwhelming.
“Everything’s ready,” Jordan chuckled. “Well, I see your cock is ready for another round.”
“Thank you for allowing me out of the cage, master.”
“You’re welcome,” Jordan kissed him. “You have a long night ahead of you, trust me.”
Miles shuddered. He eyed the entrance door.
Just a few more days, and then he’ll be the one begging.
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