Au Pair Pt. 01

Content Warning: trans man character (man with a pussy), dilf, age difference, relationship with a power imbalance, boss/employee, noncon/dubcon, mild choking, breeding kink, pregnancy kink

Author's Note: for those unfamiliar with the term, an 'au pair' is a live-in nanny that provides around the clock childcare for their employer.

On the surface, Tony D'Angelo was the owner and operator of a successful construction business but one scratch to that thin facade revealed he was the head of the D'Angelo crime family-- and not a man to be taken lightly.

Unfortunately for him, that made finding reliable childcare even more difficult than usual. Two years ago his now ex-wife, Dana, had dumped him for the pool boy and gone off to Europe to live "a less complicated life" on the right side of the law with her new fucktoy simp of a much younger husband. In the process she'd left him with full custody of their then two year old daughter, Jenna, and he'd only seen his ex on holidays since.

In retrospect Tony was glad to see her gone and more than happy to have his absolute treasure of a daughter in his life full time, but his 'job' made things... complicated when it came to looking after her. He frequently had to leave at odd hours so finding someone to watch Jenna wasn't easy on short notice and the dubious legality of his 'work' meant that just throwing money at the problem wasn't going to land him a skilled childcare provider.

He needed someone who would understand the family business-- someone who wouldn't snitch to the cops the moment they got wind of just where most of Tony's money came from. His boys weren't exactly the sort he liked leaving Jenna with full time, even if he was confident they would never be stupid enough to let her get hurt. A bright little girl like his needed someone who knew what they were about when it came to handling and teaching young children-- someone who also knew Tony's business and could shelter Jenna from it until she was old enough to understand.

By the time Jenna was four Tony was at the end of his rope when one of his boys came to him with a solution.

"Hey boss, you know, I'm seeing this guy and he's got tons of experience with kids. Used to teach kindergarten and everything-- maybe you could hire him to keep an eye on your baby-girl, huh?" one of his lieutenants, Dante, had suggested during one of the gang's poker nights.

Tony had looked at him over his hand of cards and taken a pull off his cigar then tapped the ash into the tray at his elbow. "Yeah? And why's he not doing that now?" he asked as he exhaled a thick plume of smoke. Being wary of all the angles had kept him alive and in business this long-- it was a hard habit to drop, even if it meant looking a gift horse in the mouth.

Dante grimaced. "Well, he's got school debts and being a regular teacher doesn't exactly pay good money these days."

Understanding dawned for Tony as the motivation behind the suggestion clicked into place. Dante wasn't wrong-- teaching public school didn't pay for shit these days and anyone with student loans to pay back probably wouldn't look too close at where their fat new paycheck was coming from.

"He's family, too," Dante hurried to say as he took another card. "His auntie was in, back in the day, and he knows what I do for a living. He knows not to ask questions. Plus, he's great with kids."

Tony considered a moment, then finally nodded and said, "Alright, give me his number and let him know I'll call him Wednesday."

His business had always thrived off his keen sense for opportunity and Tony knew he'd be a fool to pass this one up.

~~~

The pieces fell into place quickly after that and it wasn't long before Dante's boyfriend was sitting across the desk from Tony in his home office for an in-person interview. All his paperwork and qualifications checked out but Tony always liked meeting a person face-to-face so he could get the most accurate read on them.

Noah Russo had just turned twenty-five, making him almost twenty years Tony's junior, but he looked about twenty thanks to the baby-face the good lord had blessed him with. He was leanly built with short-cropped brown hair and features that bordered on pretty more than handsome-- particularly his big, dark eyes. It was his lips that were most captivating to the casual observer, though-- they were full and had a pleasant way of moving when Noah spoke in his low, soothing voice. His ears showed signs of piercing, though he didn't wear any earrings to the interview with his tidy collared shirt and pressed slacks.

Overall the younger man gave off a very affable air that Tony had no doubt parents and children alike got along with well. Even he found himself smiling while he asked Noah questions and he wasn't the sort to be easily moved by that sort of nicety.

"Dante says you know the sort of work we do," Tony remarked in a leading tone that Noah understood implicitly.

"I do," he answered immediately. "The aunt that raised me did the same kind of work. I don't care what you're doing to pay your bills, Mr. D'Angelo-- you can count on my discretion so long as I'm getting paid what was promised and its not directly endangering your little girl."

"Of course," Tony said, stern but approving of the line the younger man had clearly drawn. "I never bring my work home." Noah smiled politely, understanding, so Tony continued, "Since I sometimes have to come and go at all hours, I need a live-in nanny-- where are you staying now?"

Tony hadn't mentioned to Dante that he was looking for an au pair, so Noah looked surprised, but answered, "I'm living with my boyfriend, Dante at the moment, but-- well, that would work as long as you don't mind me moving some of my stuff in and will still guarantee the allotted amount of time off I mentioned before."

It was a fair ask, so Tony agreed. He tried to make sure he was home at night as much as possible anyways and in the worst case scenario he could call a short term babysitter or one of his boys to look after Jenna if he had to. It was the day-to-day stuff that was really important.

"Works for me," the man said and pushed a carefully written contract his lawyer had drawn up for him already across the desk towards Noah.

The younger man took a few minutes to read the paperwork over thoroughly and Tony respected his desire to do so-- honestly, he might have thought less of him if he hadn't.

In the meantime he took the opportunity to study Noah. Tony was bisexual and when it came to guys he generally went more for more muscular types like himself, but the man before him certainly had his charms. He had a lean build but wasn't without his muscle and Tony hadn't been able to avoid noticing the incredible ass on him. His hips were wider than average for a man, accentuated by his narrow waist and strong shoulders, but Tony had forced himself to stop categorizing his potential au pair's assets after that. They were simply too distracting in an interview setting.

He was trying to hire this man, not fuck him, after all.

"This all looks good to me," Noah said eventually then signed the paper with a flourish and Tony flashed him a pleased grin.

"Great, you can move in tomorrow."

~~~

Hiring Noah was one of the best decisions he'd made in awhile, Tony decided by the time a week was out.

Jenna absolutely adored the man-- had since the end of day one when Tony had made sure he was available to be home all day for a change just to be sure the pair would get along. The four year old's glowing reports to him about Noah and all the things they'd done together that day when Tony came home to tuck her in at night over the course of the next week only solidified the matter for him.

Noah was easy to get along with for Tony too and, even better, minded his own business-- which was to take care of Jenna. While Tony made sure to never bring any of the more dangerous elements of his work home, he still held meetings with his lieutenants and other business partners at his house on occasion and Noah had kept not just Jenna, but himself, well clear every time so Tony could focus on his work, which the mob boss greatly appreciated. Having an extra person in the house could have been awkward, but fortunately it wasn't with Noah, especially with how busy Tony was for those first two weeks after hiring his new au pair. He'd been putting off a lot of stuff in favor of looking after Jenna himself and he was relieved to finally be able to take care of it without having to worry about keeping an eye on his daughter.

Two weeks after Noah moved in the results for the additional background check he'd paid a local PI for showed up in his email inbox and Tony glanced over it while he lay in bed one night. He'd been satisfied with Dante's vouching for Noah so he'd forgotten he'd ordered it at all in the weeks since so it's arrival came as something of a surprise.

At a glance it was all stuff he already knew-- but there was a slight addendum at the end with extra content the PI had managed to dig up during his investigation.

Noah, it turned out, had a FansOnly account he'd been using to help make ends meet before Tony hired him.

Despite having no objection to that kind of work himself, alone and in his bed well after midnight, Tony was unable to resist clicking the link to view some of the free material Noah had posted to lure paid subscribers in. The younger man had been smart enough to keep his face out of frame since he was a teacher, but by that point Tony had seen him in enough t-shirts to recognize the sleeve tattoo on his right arm.

Tony had made it clear that since the man was a live-in nanny he didn't care if Noah dressed casual, which meant the younger man wore a lot of t-shirts and jeans around the house when their paths crossed anytime Tony wasn't at work-- but now the mob boss knew the wonders that were lurking under the au pair's unassuming sartorial choices.

It turned out that not only was his belly button pierced, but so were both of his nipples. Tony's nipples were pierced too, but one thing Noah had that the mob boss most definitely didn't was a gloriously wet and needy cunt.

"Holy shit," Tony groaned to himself as he lay in bed, lights out but for the glow of his cellphone while he watched a video of Noah fucking his greedy little pussy with an absolutely massive dildo.

The recording of Noah moaned wantonly in Tony's ear through the screen of his phone and the mob boss felt himself get hard while he watched. The way the much younger man's flat belly undulated as he rolled his wide, alluring hips to ride a fat dildo shaped like a horse's cock was absolutely hypnotic and Tony wasn't sure he'd ever seen anything more arousing.

"Are you gonna fill me up, Daddy?" the recording of Noah panted. His face wasn't in frame but knowing him as he did now Tony could imagine a needy, desperate sort of expression on the pretty-boy's face when he said it and groaned as he shoved his hand down into his pajama pants to jerk himself off.

"You're so good, Daddy, look at how big you are-- my tiny pussy can't handle it," Noah whined pathetically and ran his hands up his abdomen to his chest where he rolled his thick, pierced nipples between his fingers while he thew his head back and panted for breath. He leaned backwards until the dildo sheathed in his cock-starved cunt forced his stomach to bulge outwards and Tony worked himself harder, all rational thought cast aside in favor of what could only be deemed a breeding frenzy at the sight. He'd never realized he had a weakness for boy-pussy, but when Tony came a moment later it was the hardest, most overwhelming orgasm he'd had in years.

"Fuck!" he swore under his breath and thrust restlessly into his own hand as he blew a huge load across his own hairy stomach. "That's right, baby, let Daddy fuck that pretty pussy," he moaned, hips jerking erratically as he imagined fucking his daughter's nanny.

~~~

Tony subscribed to Noah's FansOnly under a pseudonym at the highest tier after that and spent a great deal of his time in bed at night going through the available backlog of videos and pictures the younger man had posted. His newfound taste for boy-cunt was overwhelming and the mob boss couldn't get enough. Tony spent entirely too much time masturbating to Noah's content, filling his trash can with cum soaked tissues while he jerked off to his maddeningly hot videos and imagined his dick in place of the man's toys.

"Why don't you ask Daddy?" Tony overheard Noah tell Jenna one day not long after and had to fight down an erection. They were in the kitchen and he was passing through the living room on his way to get breakfast when he heard Noah's question.

Fuck, he thought silently while he fought for control. Luckily, he'd been quite busy at work in the week since he'd discovered Noah's side-hustle and the younger man was discreet enough in his work to excuse himself in the evening when Tony came home so he could spend some quality time with Jenna-- but now he'd heard the man say 'daddy' in person and it was enough to bring him to the edge.

Desperate not to force his daughter to witness him with a half-chub at the breakfast table, Tony detoured into the bathroom and washed his face with cold water at the sink. When that didn't work he found himself grinding against the edge of the counter in an attempt to assuage his arousal. God damn! He'd swear he hadn't felt his horny since he was in his twenties, but now in his forties he couldn't stop jacking off just because the hired help happened to have a tight cunt and a FansOnly.

Plus he was hot.

And breedable. Just... so insanely fucking breedable. The idea of someone having a pussy while still maintaining a man's appearance and libido was so erotic that Tony hardly knew what to do with himself. The mob boss had only ever had the one child with his ex-wife before their divorce but he'd always wanted more. He'd grown up with five siblings himself and had wanted the same for Jenna until his wife had decided she wasn't into it and left him for a younger man.

"Let Daddy breed you-- let Daddy put a baby in you," Tony panted quietly to himself as he humped the counter's edge, the rounded end only just shy of too much for his raging hard-on until he reached the end of his rope and whipped his dick out then jacked himself off into the sink. "That's right baby, fuck yeah," he moaned, hand moving in quick, decisive jerks along his hot, pulsing shaft where it protruded from the front of his jeans while he imagined Noah's cunt wrapped tight around him.

~~~

"Morning, sweetheart," he said to Jenna with a warm, loving smile a couple of minutes later when he had gotten himself back in some semblance of order and was able to think moderately straight.

"Morning, Dad!" she exclaimed brightly and shoveled another bite of cereal into her mouth.

His au pair arrangement with Noah meant the man would always fix meals for Jenna but wasn't obligated to do so for Tony, which was fine by the mob boss. The pair was eating cereal and eggs this morning but Noah had been thoughtful enough to boil a few extra eggs for him while doing theirs so he could join in when he came down.

"Thanks," Tony said when he saw the eggs and started to peel then eat them. The nanny smiled at him and it sent a shock straight down to the root of Tony's dick despite his having only just gotten off a minute before.

"No problem," Noah said warmly, dark eyes crinkling sweetly at the corners while he spoke. "If you're ever home and want to eat at the same time as us you just let me know. It's not really any more effort to cook for a third person."

Pleased by the thoughtfulness but still low key aroused, Tony thanked him and tried to focus on his breakfast.

Noah, in turn, was mostly focused on Jenna, which was only right considering how much Tony was paying him to do just that, and it provided him plenty of opportunity to get a good look at the much younger man. If he'd been cis he wouldn't have really been Tony's type based on his leaner build alone-- but knowing the man was sporting an absolutely exquisite cunt and perfect, suckable nipples left Tony craving Noah's body like a drug.

The longer Tony watched the younger man the more he wanted him...the concept of a man that could get pregnant and bear his children was so agonizingly arousing to Tony he felt like he was losing his mind.

"Dad, can Noah and I go to the zoo today?" Jenna asked from where she at across him from the table.

"'Course, sweetheart," Tony told the four year old with a smile, then told Noah, "Just take whatever money you need out of my wallet. It's in my coat by the door."

"Alright," Noah responded with another smile that Tony had to drag his eyes from lest his dick start twitching again. God, how long had it been since he'd been this fucking horny? He'd just jacked off in the bathroom and now his au pair was threatening to get him going again without even touching him...

"You want to come?" Noah asked an Tony immediately shook his head.

Yes, Tony thought immediately, only just barely able to keep a straight face. I want to come over and over again in that tight little cunt of yours until you're pregnant, then I'll keep you pumping out kids until we've got a whole herd of them. I'll have to hire more help because you'll be too busy flat on your back with my baby in your belly and my cock in your pussy to do anything else. You'll make such a good boy-mommy nursing our babies by day, then I'll suck your tits at night while I fuck you pregnant again...

"Sorry. I'd love to but I've got stuff to do today. Maybe next time."

~~~

Tony didn't get home until after Jenna and Noah both had turned in for the night by design and made his way immediately into his bedroom. Not long after he got showered and fell into bed, though, he realized he'd received a notification that Noah had gone live on his FansOnly.

The mob boss tried to resist the temptation but failed and opened the link that had landed in his inbox some fifteen minutes before when he'd been in the shower. What he found there sent him immediately rock hard where he lay in bed.

Noah was in his room-- his room in Tony's house, laid out face-down with his legs spread in front of his camera while he stroked his fat, throbbing clit with one hand and fingered his wet, freshly shaved pussy with the other.

"Jesus fuck," Tony groaned at the sight. He felt borderline dizzy as all his available blood flooded straight towards his dick to give him a hard-on so powerful it hurt. Reacting immediately, the mob boss spat in his hand and began to masturbate furiously to the view.

"You want me, Daddy?" Noah whispered, only just audible to the mic built into the phone he was obviously filming with. "You want to fuck my tight little pussy?"

"Yes," Tony groaned and threw his head back, hips and hand jerking in tandem to get himself off.

"Daddy," Noah moaned, soft and wanton while he fingered himself. "I want you...please fuck me, Daddy, please? My pussy needs your thick cock," he groaned, fingers moving faster across his dripping pussy and twitching clit.

On the verge of coming himself, Tony hesitated as a thought occurred to him. He'd given Noah the room just down the hall from his. He could have the man right now... if he wanted him.

It was a bad thought-- a thought a good man would never have, but...well, Tony wasn't a particularly good man.

You didn't get to be the head of the D'Angelo crime family by being good, after all.

Cock still fully erect, Tony rolled out of bed and eased his door open then entered the hallway. He checked that the light was off there then made his way by memory to where he knew the door to Noah's room was.