TransgenderChapter 5 of 8Ongoing

Au Pair

Au Pair Pt. 05

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Au Pair Pt. 05

Content Warning: trans man character (man with a pussy), dilf, age difference, relationship with a power imbalance, manipulation, boss/employee, noncon/dubcon, breeding kink, pregnancy kink, cuckoldry, exhibitionism, voyeurism, sex work, drug use (ecstasy), anal sex, sex with an unconscious person

Author Note:Just a heads up, this story is going to consistently be fairly dark so mind the tags!

Noah came around to the heady, familiar scent of Tony's favorite brand of cigars and after a moment's disoriented fumbling the man managed to push up off the pile of pillows he'd been draped across and onto his elbows.

"What happened," he asked, head swimming, mouth feeling like it was full of cotton.

Tony looked up from his phone and blew a cloud of smoke towards the ceiling before answering, "You were begging for cock so I brought you down here and gave you some." He smirked and added, "You were screaming like a bitch in heat, begging me to knock you up."

Begging for cock sounded about right for him, Noah thought unabashedly, still heavily buzzed enough that his sense of shame hadn't reared its head again yet. He'd always been a bit of a horny drunk in the right company-- the more he drank the quicker he was to spread his legs.

Still, that last part didn't quite sound like him.

"But I don't want kids right now," he began but was interrupted by a gush of wetness between his thighs accompanied by the lingering echoes of a shuddering orgasm and a soft, obscene moan. Panting a little, eyes rolling back in his head at the sensation, Noah reflexively spread his legs wider and flexed his abdomen, forcing more of the fluid out of gaping, battered cunt.

"Fuck, you're a hot mess," Tony said, sounding turned on rather than insulting as he watched from his seat on the small sofa nearby. He looked about to say something more but stopped when his phone rang. He scowled and got to his feet. "I've got to take this. You go get cleaned up," he instructed Noah then left the small room.

"'Kay," Noah replied absently, eyes locked on the pool of what he assumed was Tony's semen that had just leaked out of him. "Fuck," he added then flopped back onto the pillows and lay there for a minute.

He didn't stay long, though. While his thoughts were more sluggish than usual, Noah wasn't so high anymore as to forget literally anyone could walk into the room and find him with his legs spread, boss' come dripping from his pussy, and decide to take advantage of the situation. The man may have sold his body to Tony, but that didn't mean he was about to let justanyonehave their way with him. Especially not some random stranger.

Noah managed to find his shorts and clean up with some tissues enough that it wasn't obvious at a glance what he'd just been up to, then made his way back out into the hall. The former teacher wandered vaguely in the direction he remembered the nearest bathroom being but was but stopped along the way when he spotted a man in a corner booth selling some familiar pills. The previous one was starting to wear off, leaving Noah riding solo on liquor and champagne and Tony hadn't mentioned they were leaving any time soon...

The dealer caught him looking and flashed him a smile that drew Noah to him like a moth to flame.

"Hey, pretty boy, what you looking for? I've probably got it," the stranger said, coaxing him in closer with a crook of a long finger. He didn't have much going on in the looks department beyond being relatively fit but the dealer's smile was a killer and something about his demeanor made you want to spend more time in his presence.

"You have any more E?" Noah asked, words tumbling from his lips before he even thought about it as he dropped into the booth beside him.

"Of course," the dealer said with another one of his enticing smiles. He pulled out a pill bottle from inside his coat, rattled it, and named a price.

Noah automatically reached for the pocket of his jacket but realized he wasn't wearing it. He didn't even remember taking it off, now that he thought about it, though if he had to guess it was probably in the VIP room. "Shit," he cursed irritably and dropped his head back onto the booth with an annoyed sigh.

"Ah-- maybe later, then," the dealer said and began to put the bottle away again.

Now that he'd had the thought, though, Noah didn't want to let the pill go, so he reached out and said, "Wait-- can I... pay some other way?"

"Man, you know how much I get that line?" the dealer asked with a snort, but his eyes gave Noah the once over all the same. He must have liked what he saw, though, because rather than blow Noah off entirely, he jerked his chin and looked meaningfully at the au pair's hips then asked, "What you packing down there?"

Realizing what he was asking, Noah turned to face the other man more directly in the booth, spread his legs a little, and deftly dragged aside the crotch of his shorts to expose his pussy for inspection. The manreallyliked what he saw then so he glanced around and jerked his head again for Noah to move closer.

"Alright, baby, hop on and we'll get you what you want," the dealer said as he shifted some to unzip the front of his pants and pull out a dick of respectable size. "Never had boy pussy before-- you better make it worth the pill," the man added as he quickly gave himself a few pumps and slid on a condom.

He should have been mortified by the prospect of turning tricks for drugs at the club, and he was, but there was no denying Noah was aroused as well and he slung his leg over the dealer's hips to mount him with barely a second thought. He sighed pleasurably at the gentle spread of his lips when he dropped down onto the other man's cock and began to ride him at a quick pace that matched the furious beat of the music piped in through the speakers overhead.

"How's that?" he asked in a soft voice directly by the dealer's ear. The man didn't have to answer, he could tell he was enjoying himself from the pay he was panting and grabbing at Noah's hips. "You like your first taste of boy pussy?" he added a little smugly as he tightened around the man on the upstroke and loosened again on the drop in an effective milking motion he'd perfected for Tony.

"What the fuck, dude, this is insane," the dealer groaned, groping at the rest of Noah's lithe body while the au pair worked him over. He came a moment later with a shuddering groan that left him twitching and panting as he blew his load into the condom he'd put before they started.

Pleased with himself despite his embarrassment, Noah climbed off the man and claimed his reward, popping the pill and washing it down with a complimentary shot the dealer poured for him.

"Brother, you ever wanna do some high end escort work you just give me a call-- I've got someone I can put you in touch with," the dealer said and passed him a card. Noah blinked and accepted it automatically, but tossed it in the trash can just as soon as he made it to the bathroom.

He barely had time to relieve himself and make it to the sink to wash his hands before the door swung open again to admit Tommy. His friend looked flushed, definitely drunk, but mostly irritated, Noah could tell at a glance.

"Where the hell have you been? Did I-- " he lowered his voice and approached Noah with a fierce but awkward look about him. "Did I just see you fuck a guy in a booth for pills?"

"Just the one pill," Noah said, which was just starting to hit. He'd be mortified tomorrow by how easily he admitted to prostituting himself for drugs, but for the moment he placed a hand on the muscular expanse of Tommy's chest and relished the softness of his cotton shirt.

No doubt his skin would feel even better.

"You want a go?"

The simple question killed whatever lecture Tommy was about to give him before the man could even open his mouth. "What?" he asked stupidly, as if he couldn't believe his own ears.

Noah stepped in closer so he was pressed flush to his friend, both hands on his chest, hip-to-hip so he could feel the hard line of Tommy's cock through his jeans. "You want to fuck me, right? I know you like me-- you're always staring. Have been for years."

"I-- you're high," Tommy said and took a step back admirably. Not so admirably that his cock wasn't making an absolute tent out of the front of his pants, though.

"Andyou'redrunk."

"Youhave aboyfriend,"Tommy insisted half-heartedly, eyes positively devouring Noah as the au pair took a step, turned to face the mirror over the bathroom sink, and tugged his tiny shorts down over his hips to expose his ass and the slick folds of his pussy.

Noah planted his hands on the edge of the counter and arched his back enticingly while he looked at Tommy in the mirror. "I won't tell if you don't."

Tommy had protested twice, but he wasn't strong enough to do so a third time at the sight of everything he'd wanted for years was offered to him on a silver platter. "Fuck," he swore and stepped up behind Noah and ran both hands over his incredible ass. "Fuck, I've wanted you for so fucking long," he hissed softly as he worked his pants open with one hand and started to finger Noah's pussy with the other.

"Then hurry up and take me," Noah demanded, that familiar heat overtaking him again. His body was going to be an absolute ruin tomorrow, but for the moment he could have choked to death on a cock and still felt it wasn't enough.

Behind him, Tommy stopped fingering Noah and paused. "Did you let that dealer come in you?" he asked incredulously.

"No," Noah answered truthfully, "that was someone else."

"How many people have you fucked tonight before me?" Tommy demanded.

Noah looked at his friend in the mirror and while Tommy was clearly irked, the way his cock was practically throbbing in his hand was all the sign the au pair needed to know the man may have been annoyed but he wasalsoaroused by the thought of fucking someone else's sloppy seconds.

"Two guys and a trans girl with the best tits you've seen in your life," he answered unashamedly, riding high on the thought of cucking his friend with two total strangers and his own boss who secretly employed him full time as his personal whore.

Tommy spat and Noah flinched a little when he felt it hit his asshole rather than his cunt. "Fuck, bitch, if I'd realized you were such a slut I would have done this years ago," the man said and proceeded to force his cock into Noah's ass raw.

The sudden spread of his hole made the au pair gasp and he would have yelled if Tommy hadn't slapped a hand over his mouth to keep him quiet.

"Don't you fucking scream, not until I'm done with you," Tommy growled and pushed harder, forcing himself in deeper while Noah groaned into his palm. "Shit you're tight," he panted, struggling not to come immediately, but he grinned all the same and added, "You're giving that cunt if yours away to anyone who asks but I guess I get to be first here tonight at least, huh?"

Noah shuddered as his friend forced his way into his ass, but after a moment it was easier than expected. Easier than anal usually was for him-- especially with only spit and his own lingering juices for lube. The excessive drinking and ecstasy had left his entire body loose and that went for his ass too, apparently, letting him take Tommy to the hilt with little effort on his part after the initial stretch.

Tommy soon began to thrust, but it wasn't enough for Noah, who pulled his friend's hand from his mouth and said, "Harder, fuck me harder!" Tommy tried, but between the ecstasy and the fact Tony had been breaking his ass in on the regular with his massive hog of a cock when he wanted it extra tight at home, Noah barely felt his friend's prick. "Come on, like you mean it!" he demanded and threw his hips back to meet Tommy's while he reached between his thighs and rubbed his swollen clit in an attempt to get himself off.

It wasn't enough, though, it wasn't anywhere near enough, and Tommy came well before Noah was ready, grunting and groaning the whole way through.

Tommy pulled out with a sigh and a pleased look on his face, but that faltered when he glanced up at Noah in the mirror and witnessed the disappointed look on the other man's face.

"Seriously, after all that talk?" Noah demanded, pent up and on the edge now. He hadn't gotten to come with the dealer either, but at least that guy had given him ecstasy in exchange for using his body to get off. Tommy was looking at him like he expected Noah to be blown away by what little play he'd given him.

"Uh--" Tommy began, but was interrupted by a man in the doorway that both of them had been too distracted to notice enter.

"Fucking pathetic," Tony said of the performance.

Elation and fresh arousal surged through Noah like a wildfire. "Daddy! Oh, god, daddy, please, fuck me. I can't-- hah," he groaned a little as he started playing with his clit again and arched his back in invitation to his boss. "I can't come without you."

"Who--" Tommy began, but Tony was already pushing him out of his way and unzipping his pants.

"Out of the way, boy. I'll show you how you put a whore in his place."

"Yes, oh god yes," Noah moaned and spread his legs, practically shaking with anticipation as he braced his hands on the counter again. "Please fuck my pussy, Daddy. Use me!"

Tony pushed the fat head of his cock into Noah's dripping cunt while Tommy stared on, flabbergasted, dick in hand as the older man stepped in and claimed what he'd thought was now his. The guttural groan of ecstasy that echoed up out of Noah as his boss mounted him for the second time that evening made Tommy flinch and look away, suddenly aware of his own obvious shortcomings.

"Stand against that door-- don't let anyone in til I'm done," Tony commanded Tommy while he fucked Noah with quick, hard jerks of his hips.

Against all reason, Tommy, still dazed, obeyed, eyes locked on Tony and Noah all the while.

"I take my eyes off of you for five fucking minutes and you start running around fucking anything that will have you like a cat in heat," Tony snarled, though in the mirror he was grinning ferociously while he watched his au pair pant and moan, completely overcome by his assault. "If you wanted more E, you could have just asked, you dumb slut," he added and produced another pill from his pocket then pushed it into Noah's slack-jawed mouth.

The au pair swallowed reflexively, eye-lids fluttering as he sucked and licked Tony's fingers before his boss withdrew them. "Sorry, daddy, I forgot my money upstairs," he confessed. "I didn't let him come inside, though, promise," Noah panted as an afterthought.

Tony snorted. "With all the whores around here trading in kind he knows better than to not wrap it up." He glanced sidelong at Tommy then, and said, "At least you got something from him-- better than you can say for letting that idiot fuck you."

"Hey," Tommy began to object but shut up at a sharp look from the mob boss. Whatever buzz Noah's friend had going when he'd entered the bathroom was fading fast now and his survival instincts were sharp enough to know better than to challenge the enormous, dangerous looking man helping himself to Noah's body.

"S-sorry, daddy, he's my friend--"

"So?" Tony demanded. "Looks like I'm gonna have to teach you a lesson about keeping your fucking legs closed in public, huh?"

He pulled out of Noah's pussy with an almost audible pop, making the younger man gasp, then pressed the head of his cock to the tender pucker of his ass. "Wait--" Noah began, but to no avail as Tony rammed his enormous dick, still slick from pounding the au pair's pussy, into his ass in one brutal push.

Noah reallydidscream, then, but it was into Tony's heavy palm as the mob boss anticipated his reaction, muffling the noise into little more than a whimper.

The difference between Tony and Tommy's dicks was night an day-- Noah had barely felt a stretch with the latter but the moment his boss started moving his hips again he felt the older man really might turn him inside out. He was going to break him for sure Noah thought as his eyes rolled back in his head, knees giving out so Tony was forced to catch him.

"You're not getting off that easy," the older man growled in his ear when he looped his arms around Noah to pin his slender body back against the broad swath of his powerfully muscled chest. He rolled his hips and continued to fuck up into Noah's ass, grinding into him, churning his guts like so much butter.

Able to do little else, Noah reached down and stroked his clit again, panting wantonly as he watched his boss fuck him in the mirror, Tommy completely forgotten. "Fuck! Oh fuck, daddy, I can see your dick!" the au pair groaned as he realized he could, in fact, see a slight distortion in the surface of his belly with every thrust of his boss' cock. Entranced and unspeakably turned on by the sight, Noah pressed his hand just over it and moaned at the sensation of feeling the man's dick from both sides. "You're so deep," he mumbled, head lolling back against Tony's shoulder.

Stomach practically empty of anything more substantial than champagne and hard liquor the extra dose of molly was starting to hit Noah hard and fast the longer they went on like that. The slide of Tony's calloused hands over Noah's feverish skin felt like the finest silk to the au pair's drug addled mind and the distant music pounded through him like his own heartbeat, carrying him away in a tide of indescribable pleasure. The darkness closed in as Noah came again with a trembling sigh and fading whimper.

~~~

The sight of Noah coming completely undone in his arms made Tony come again as he watched their rough coupling in the mirror. It was enough to make him consider having a few big, floor-to-ceiling mirrors installed in his bedroom so he could enjoy the sight in the comfort of his own home. No doubt the show would be even hotter once he'd managed to knock the boy up, too...

"Get out," Tony told Noah's pathetic little cuck friend who had been watching them the whole time and jerking while he thought they weren't paying attention.

The look he gave the brat was enough to make him come with a pitiful little moan but at least the guy had the wherewithal to look embarrassed about it after while he quickly zipped up his pants.

"Lose Noah's number while you're at it," Tony told his retreating back. "I don't want to see you again." The guy only paused briefly as he opened the door, then rushed out, face red.

Well and truly gone, Noah could stand kind of haphazardly if he gripped at the sink's edge while Tony cleaned up and pulled the au pair's shorts back up to cover his ass. When he did the lips of Noah's pussy, swollen with arousal and repeated pounding, poked out either side of his short's tiny crotch. It was absurd, but undeniably erotic-- enough so Tony couldn't help but crouch in front of the younger man to lick and suck at them for a moment while soft cries of gratification bubbled up and out of the disoriented au pair.

When Noah's knees nearly buckled again Tony gave up licking at the fat stub of the man's clit through the fabric of his shorts and lead him out of the bathroom. He found Mark waiting nearby and instructed him to gather up their things from the VIP room then headed for the back door of the club where a hired car waited for them.

It was past two in the morning but there was plenty of neon lights to illuminate the alley they emerged into. A few steps out, though, and Noah's legs finally gave up the ghost as he blacked out. Tony caught him easily and swung his lithe, thoroughly debauched body up into his arms then carried him the rest of the way to the car.

The driver hopped out promptly and opened the rear passenger door so Tony could place Noah on the seat inside the sleek, black limo.

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