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Disclaimer: I don't have anything to do with or own How I Met Your Mother nor any of the characters or settings, specifically Robin Scherbatsky and Sandy Rivers. I make no profit from this fictional story

Summary: Set within season 6 but no spoilers. Robin has been hired at World Wide News but only as an unpaid research assistant job. She needs money and a place for advancement is coming up. Her boss is hot so it's not really prostitution.

Pairing: Robin Scherbatsky/Sandy Rivers

Codes: MF, Anal, Finger, Oral



How I Met Your Mother: Getting Ahead
by The Chemist

"Why the hell did I turn down being that currency rotation specialist for Million Dollar Coin Flip," Robin Scherbatsky asked before taking another long pull of her beer.

"Because you have self-esteem," her best friend Lily answered, sitting across from her at their favorite bar.

"Nope, that wasn't it," the gorgeous brunette retorted. "Oh right, to work at World Wide News. Well, work is a loose term. Is it work if you don't get paid?"

"Don't be so discouraged Robin. We are with one of the best global news agencies. You have to put in the dirty work to get ahead," the more mature teacher explained.

"And if you mean put in time on your back for your boss when you say dirty work then yes, you are probably right," Robin retorted bitterly as she ordered another drink.

It was a poorly kept secret around World Wide News that Sandy Rivers, the head news anchor for the company, had final say on hirings from the research team. So far in the half-a-year Robin had worked for the company, 5 people had been promoted by Sandy. All were women. All were extremely attractive. All were known to have rather extensive sexual experience if office gossip was anything to go by.

"Oh shoot, I need to get back home. Marshall is making dinner...but I could always cancel," Lily offered, though it was spoken in a way that gave off the impression she didn't want it taken up on.

"No, you go have dinner with your perfect husband," Robin shooed her away. "I need to get back to the apartment anyway. I have another interview tomorrow so should probably get a good night sleep."

The friends finished their drinks before leaving McLaren's together before heading in their different directions. It was a somber walk back home for Robin, seeing happy couples out on the street or people getting home from their clearly fulfilling jobs. She had neither, and though her interview for a better position was tomorrow, she held no hope of getting the job.

Those were the thoughts that floated about her mind as she settled in for a restless sleep that night. She had dreams, well nightmares, of still being in the research division of World Wide News until she had grey in her hair. All while her friends succeeded, Ted designing a New York City skyscraper, Lily winning teacher of the year, Marshall making partner at his Environmental Law Firm, and Barney...well Barney continuing to be Barney.

"No! No this will not happen," Robin swore to herself as she woke up that morning.

Robin had been paying her dues with the massive new agency for 6 months now and yet there was no movement on her situation. Her savings were getting drained even if she was living with Ted, who was fronting her rent. New York was an expensive city and what made it even more frustrating was the fact several other girls in the research wing had moved on to better opportunities.

"Now it's my turn," Robin said into the mirror as she finished straightening her hair.

Looking at her reflection actually made the Canadian wet between the thighs. She had her big chance with the boss today and was dressed the part. Right now she had on only her lingerie, all black consisting of a bra to push-up her modest yet perky tits, a thong to highlight her scuplted ass and garter belt to hold up her matching black stockings.

A quick look at the clock told her she had to getting moving if she was going to catch her train. She stepped into her high heels, which better showcased her long, flawless legs before buttoning up her white blouse and pulling up her tight-fitting business skirt. She got several long looks from fellow commuters, which only served to reinforce that her dress attire was the right choice for today.

* * *

Luckily the day was passing by quickly, which was better than she expected. Her interview was at the end of the day, which normally made the day stretch out and feel endless. However, today she had a sense of calm about her, a plan firmly in place about how to handle it. She didn't dread the meeting, instead she was resigned, confident and prepared.

"Another job interview, Robin," the petite Nora asked her.

"Yup. With Sandy fricking Rivers," the leggy brunette replied.

"Well good luck, he's a massive pervert," Nora warned before wishing her luck in a more sincere attempt as she left.

"That's what I'm hoping on," Robin said to herself, fixing her top to make sure her modest cleavage was on display.

She headed back to her desk briefly to close up her station and return what she had been working on before grabbing her purse and heading to the big office at the end of the floor. She stopped and gave her name to the secretary and only had to wait a few minutes until a young woman was ushered out of the office by Sandy Rivers.

"Fantastic Jennifer. You'll hear from me soon about the position," Sandy said in that booming voice of his. "Okay Robby, I can see you now."

"It's Robin actually, Robin Scherbatsky," the leggy brunette corrected, standing up and extending her arm to shake hands.

"Yes, yes you certainly are," Sandy said as he took a good look at the stunning woman. "I'm sorry but do you actually work here? I thought this was an internal job posting?"

"Yup...for the better part of half the last year," Robin answered as he took her through the office and into a more private anteroom.

Where the actual office was a wide open room complete with wall-to-ceiling glass walls, this smaller room was enclosed to give privacy. It wasn't large, maybe a 12x12 space complete with a leather sofa, which Sandy took a seat on, and 2 large chairs across from it with a glass table in between them.

"Okay Robin, so you are here applying for the vacancy..."

"I'm sorry to interrupt you Mr. Rivers but I'd love to cut to the chase and save you some time. I value working for World Wide News and you specifically, which is why I'd really love the chance to work directly under - or on top of - you," Robin said, throwing out her Hail Mary right away.

"Oh wow, Robin," Sandy said with alarm though judging by the note in his tone, he was playing it up.

Robin stood from her seat and walked around to where the news anchor was on his sofa, undoing one of the buttons on her blouse in the process. She undid a second then a third before needing to untuck the shirt to get the last one, leaving it open to reveal her perky boobs and toned, fit stomach.

"And I feel words can't quite capture how badly I want that to happen but I might be able to show you by offering something that proves how motivated I am," Robin continued. "Something very special."

"Well...my curiosity and attention are all yours Ms. Scherbatsky."

Robin had to fight back a smile at the way the older man stuttered just a little bit, losing his normally perfect composure. She tested him once more by undoing the zipper on the back of her skirt before letting it slid off her long legs to show off her stockings, garter and thong. She lost her blouse as well to give him the full affect of her lingerie before sitting on the sofa right beside him.

She didn't say a single word as her right hand massaged right over his groin, feeling his hardening cock strain against his trousers. She undid his belt and pants, looking him dead in the eye as she did so before fishing out his manhood which was now fully erect.

"I think you are making a hell of an impression for this job opening," Sandy cooed, tucking a loose strand of her silky hair back behind her ear.

She nodded her head as her hands began tugging down his dress pants, requiring Sandy to hike his hips off the sofa so she could get them down around his ankles. Robin couldn't stop herself from bulging her eyes at the sight of his cock, picking it up into her fist and pumping it gently yet firmly at the same time.

"You have a really big dick," she said with a tone of amazement and longing.

"I know," Sandy replied smugly.

With a wicked grin on her face, Robin glided his cock towards her face before engulfing his bulbous head between her lips. The brown-haired man couldn't help but let an audible moan as her hot wet mouth worked the first half of his cock over. Sandy was dangerously close to losing control and popping his load in her mouth once she worked her bobbing to a blistering pace but he found his center and just enjoyed the performance.

"Yes. Suck it babe," Sandy moaned in delight towards the dirty brunette.

"Mmmmm," Robin moaned as she noisily slobbered on his meat stick, right in the middle of his office.

The famous news anchor grunted and groaned as her warm mouth sucked on his sensitive member as she felt momentum. It was clear she was a professional when on her knees, making him think of all the fun they could have if he gave her the new job. His thoughts were paused suddenly as her free hand reached down to cup his balls before rolling them gently with her fingers.

"Yes! Get that dick good and wet with your mouth," Sandy encouraged, hand resting on the back of her head.

When it came to oral, Robin's game was on point. She had a few different styles she deployed so her vast amount of boyfriends and fuck buddies over the last few years were always kept happy and never bored.

After she stroked her lips onto his pole for several bobs she pulled her mouth off him altogether with an audible pop so she could lower her head further. The feel of her wet tongue sliding from his tight ball sack up the entire length of his cock felt great, which Robin knew it would. She went back to her regular blowjob but would periodically lick the entirety of his manhood, hearing him coo his appreciation when she did so.

"Do you like that, Mr. Rivers," she asked with a cocky smile.

"Mhmm...you might just get that promotion after all," he said, pulling her face towards his so he could press his lips to hers.

They didn't kiss for long as they both knew where they'd rather her lips be. She wasted no time bending back down and taking half his meat spear into her mouth, bobbing repeatedly so his bulbous head poked the back of her throat. He could hear the extra spit pool onto his shaft when she did so, making the blowjob get noisier and allowing her hand stroking the lower portion of his dick move at near the speed of light.

"That big dick tastes so good in my mouth," Robin told him after another lengthy spill with her head in his lap.

"Fantastic," he said, already steering her face back down. "Keep you head down there."

The sounds alone from the blowjob were erotic enough to keep him aroused, let alone how it felt. Wet slurping noises filled the small anteroom of his office as Robin showed great energy to bob routinely on his dick. The tall Canadian would mix in the odd moan, which caused her tongue to vibrate on his cock, or gasp for air after holding him down her throat for a spell.

While normally Sandy didn't condone a girl spitting, unless it was spitting his cum into her friend's mouth to share, he gave Robin no ill will as she spat some of her drool unto his member. Her fist used it as lubricant, somehow going even faster now as it pumped along his entire length. Robin hovered her mouth right above his tip though, using her tongue to lash out tenderly at his pee slit which made the news anchor toss back his head and moan.

"Oh God! Keep going," Sandy bellowed.

She knew he was close but she didn't think merely wiggling her tongue along his tip would do it. She was banking on him being like most other guys who got off on watching as the girl took his balls into her mouth, sucking them one at a time while using their broad tongue to rub the curved surface. As she did so to Sandy now, he proved that he too was like all her other conquests.

"Yes Robin...I'm close...wanna...gonna cum on your pretty face.

The leggy brunette was pleased that her ordeal was coming to a close and that the new job would be hers right after taking his money shot onto her gorgeous face. She allowed him to moved her, positioning her head on his stomach but letting her continue stroking his cock as that was pushing him over the edge of his orgasm.

"Yes, yes, yes...here it comes!"

At the last second he took his cock back from her and leaned it right against her nose as he lightly rubbed his shaft, finishing himself off. The white jizz came shooting out of his tip before arching downward, the first streak catching Robin on her forehead before the second and third streaks welled in her left eye and against her nose. Finally he pressed his tip into her mouth, the remaining dribble collected on her tongue before Robin played the good girl and swallowed it down.

"So did I get the job," Robin asked hopefully, the cum taste still on her tongue and her face still streaked in sticky jizz.

"Haha, maybe. You still have to pass the 'at home' test," Sandy revealed as he walked to his desk before pressing a button on his phone. "Anna, call for my car to be brought around."

* * *

Sandy lived close by to the massive News Agency building in one of the nice condos in Manhattan. It was good that they had a few glasses of scotch on the way out of the building to help Robin keep her nerve, although she had come this far already so she may as well see it through.

Robin barely had time to register any details of Sandy's bedroom as the second they were through the door he spun her around and crammed his tongue into her mouth. He hadn't allowed her to get dressed once leaving World Wide News, giving her a trench coat to hide her lingerie, which had already been discarded leaving him to paw at her barely covered body.

"Won't be needing these," Sandy said, removing his own clothes with Robin helping before undoing her bra. "Mmm, small but oh so suckable."

"Mhmm yes...lick my nipples," Robin cooed as her hand went back to stroking his cock, hard once again.

"You ready for me to fill your little pussy up," the older man asked, unable to wait any longer.

"Yeah...I want you to fuck me so good," the leggy woman replied, putting as much sultry into her tone as possible.

"I bet that pussy is already wet for me," Sandy continued his dirty talk as he laid his naked body down on his bed.

"Soaked," Robin retorted, already having striped out of her thong before climbing overtop to straddle his waist.

She was just as tight as Sandy expected, the girl only in her garter belt and stockings. She sat on his cock and only managed to get less than half his 8 inch member into her pink hole. However, Robin was the determined sort so she let gravity do the work as she pressed her body weight downward until she felt her boss' thighs against her toned ass.

"Mhmm...oh," Robin moaned as she was completely filled by Sandy.

The first few times she rode him to the top and back down were slow, allowing herpussy to stretch to accommodate his decent girth and spread her juices. As she got use to his size she started to buck a little faster, only working the upper half of his member and whipping him into a frenzy in the process.

Robin had slept with many men countless of times so had perfected her craft. She didn't want to do one thing for too long lest become boring and predictable. After the rapid stroking she drove down fully onto his dick and sat there, grinding her hips back and forth. It worked as she felt his hands grope her tight ass harder and suck the nipple between his lips more urgently as well.

"Feel that big cock stretching you pussy," Sandy grunted as her snatch glided along his entire length.

"Yes...fill me...stretch me," Robin cooed. "Fuck me just like that. Deep and slow."

Sandy took back some control, using his strong arms to help hold her propped up on her knees so that he could drive his hips off the bed and into her. His cock completely left her pussy on the way down only to spread her velvety lips as his rounded head pushed back inside. They both felt his entire track deep inside her snatch, the wetness lubricating her tight walls and driving them both mad with hormones.

Robin wasn't oblivious to the fact his fingers kept grazing over her puckered asshole either. They never stayed on the spot for long, but the sheer number of times he touched her on the crinkled starfish was far from accidental. Not that the leggy brunette minded. Hell, she couldn't count with her fingers and toes the amount of times she'd been fucked in the ass, let alone the other times a guy, or girl for that matter, only stuck a finger into her brown eye.

"Oh yes! I love that hard fucking dick in my pussy," Robin swore, her dirty mouth on full display.

"Good...because the forecast has lots more in your future," Sandy said, using the voice he did to announce the news which oddly turned Robin on more.

For the next several minutes they used each other, Robin motioning up and down while Sandy groped, sucked and thrusted. They had found their stride together and the sheer number and volume of their moaning was proof of that. Even when the news anchor got around to spanking her firm ass, hard enough to leave a red mark on her sunkissed skin, Robin found herself smiling and hoping for more.

"You're such a bad girl. Sleeping with the boss to get ahead. That deserves to be punished," Sandy said, spanking her toned ass once more.

"Yes! Punish me," Robin screamed, riding his cock even harder.

The only noises able to be heard now were the more visceral grunts coming from the pair, but even those were muted compared to the sound of Sandy's palm cracking the fleshy ass of Robin. If listening close enough you could make out the wet slapping noise of his cock pounding deep in her snatch as well, and the lighter thumping of his balls as the bounced up and smacked against her puckered hole.

"You love this don't you," Sandy exclaimed, bringing a finger to push into Robin's mouth.

"Mmhmm," the leggy brunette murmured her agreeance as she sucked the digit.

It became clear to Robin why Sandy had her suck his finger and coat it in her spit as he transferred it from her mouth and back behind her. This time his finger did more than graze against her crinkled orifice as she felt him rub around the outer ring until he rested right over the center.

The Canadian was far from an anal virgin so her asshole but up little fight as he pushed against it until his finger disappeared up to the first knuckle. He didn't attempt to fuck her backdoor just yet with the digit, only letting it soak within the first few inches of her tight opening to let her get used to the feeling, and also to see if she would be angered with a little anal play.

"Ah Fuck...Oh my God," Robin moaned, her orgasm building quite nicely.

"Harder! Faster," Sandy demanded, using his free hand to spank her ass once more. As he felt her pick up the speed to a frenzied level he smiled up at her for following directions so well. "Good girl...that's it baby."

If the finger in her ass, which she had always loved when a guy did as they were fucking her, was the start of her building climax then the harder ride was the push it needed to get even stronger. He had pushed the digit in even further which was the exact thing she wanted when she started rocking backwards on his dick every time she descended down.

"Oh...I'm gonna cum," she announced. "Oh God!"

In truth Sandy didn't care one way or another if the brunette with the great body came or not. He fucked her all the same, keeping the same thumping rhythm even though it was rather exhausting and bordered on feeling too good. After all, he still had a lot planned with Robin or whatever her name was.

"Fuck yea...just like that," Robin said, her eyes closed tightly as she felt her orgasm within reach.

"OH! Keep fucking me like that! I'm gonna cum," she announced, each word shouted louder than the last. "I'm cumming!"

Robin felt the familiar overwhelming feeling of tingles shooting throughout her lean body. She became light-headed, her vision went blurry as it felt like instant lightness spread through her body...except for her clit which just felt like a series of fireworks being lit off. She had to fight from blacking out, instead collapsing down on top of Sandy, unable to think, move or speak for a few moments.

"Good girl," Sandy said as he lightly thrust up into her through the last of her orgasmic bliss.

Robin came back to full awareness, realizing that this wasn't a boyfriend who wanted to cuddle. No, this was her boss who decided if she got the big new raise and much better pay. She was far from done here and she needed to see the task done to completion so she swung her long legs from around her body and knelt next to his lap.

She didn't say a word to Sandy as she bent down to hover over his groin before taking his extremely wet in her hand and guiding it into her mouth. She moaned as she tasted herself on his erect pole, forming a tight seal around him with her lips and bobbing up and down. She took him as deep as possible, sticking her tongue out further as well to collect more of her cum as she could.

"Tastes good to lick my cum from your cock," Robin said with a big smile. "Now I want you to put that dick in my ass to let me get the promotion."

"Those are fair terms," Sandy replied after thinking about it for half a second.

Robin was already in motion after giving him a quick kiss, turning her back to him as she straddled his lap once more. She didn't want to call herself a pro when it came to sex since that made her sound like a prostitute, but she took pride in her ability.

His cock was drenched from her cumming on him and the added spit she applied, so as she sank her body weight onto his member she felt her sphincter give way. Inch by inch he pushed into her bowels, the news anchor smart enough to know that Robin was in complete control in this initial phase. Which was wise, because in her first descent she took him all the way into her anal opening.

"Awh...yeah," Robin moaned.

Sandy was absolutely shocked and filled with amazement at the same time as he watched and felt the slender brunette ride his cock from tip to base at a slow yet steady pace. For Robin, she found that she was just a flat-out fan of anal sex. It felt more intense, activated more pleasure centers in her brain and orgasmed more often. However, that could all be cancelled out by an over-pompous partner but luckily Sandy didn't appear to be that.

With her arms reaching behind her to hold herself up against Sandy's chest, Robin used her well-toned legs to drive her up and down his very slippery cock. She could feel every inch of him sliding in and out, which simply couldn't be felt with vaginal sex. She could even feel his balls slap against her pussy as she went all the to his base

"Fuck me Sandy," she told him, sitting down fully in his lap.

That was clearly her passing the news anchor the baton for him to take over control, which he gladly did. He made Robin recline further against his chest, relaxing her so that he could push his hips upwards, plowing into her ass. He started off at roughly the same slow speeds she was going, but slowly got faster with each thrust.

"Oh shit," he groaned, as Robin wasn't the only one thriving in the more intense sex.

"Yes. Fuck my ass just like that," she urged through a series of moans.

Sandy did just that. He placed his hands on her stocking-covered hamstrings to hold her legs up and out to give him better access to her tight backdoor, allowing him to thrust as hard as he wanted. He kept his stride smooth which helped keep her relaxed, as did when Robin used her own free hand to reach between her thighs so she could coupled the anal sex with stimulating her clit.

"Oh my God...you're stretching my ass so much," Robin told him.

"My word, you really do enjoy a dick in your ass," Sandy commented, his hips continuing to thrust up and spear her asshole.

"Yes! Keep fucking my ass," she continued to encourage.

A few things happened all at once to Robin. First she felt her boss start fucking her even harder, which was expected. After all, everything was going smoothly and she was proving she could handle herself well. But his hand coming around to replace hers between her leg, first rubbing her clit like she had been doing but then actually cramming two fingers into her well-used pussy.

Robin felt like blacking out from the sheer intensity of the pleasure being elicited in her brain. To have both her sensitive holes filled and stretched out at the same time, all while his palm rubbed her clitoris was like a new high better than any drug. She think she came but she couldn't be sure, but judging from the way Sandy slowed his thrusting she had a good idea he did and that her sphincter had become a living, organic vice around his cock.

"I want you to taste your fucking asshole," Sandy demanded, knowing it would allow his stamina to improve as well.

"Whatever will get me that job," she answered without delay, swinging from his lap in the process.

She knew that some, or a lot of men found this act to be so kinky and arousing that Robin had sucked on a cock numerous times after it was fresh from her ass. With Sandy was no different as she gripped him at the base to hold him upright then started sucking on his dick, really swirling her head and making audible sucking noises for his benefit.

In truth there was very little taste, especially nothing disgusting so she was more than happy to blow Sandy after fucking her ass for the past while. She bobbed down on his member time after time, using her tongue to rub his shaft all while transferring more spit to his surface. He hadn't cum yet and she was certain he'd want to continue back in her backdoor.

"I want some more," Robin told him after cleaning off his dirty cock.

"Oh, you're going to get more," Sandy agreed readily.

As if they had read each other's minds, while Sandy was getting up onto his knees Robin was rolling over and propping herself up onto hands and knees with her tight ass pointed back at him. Now kneeling directly behind the stunning woman, Sandy leant down and spat directly into the center of her still gaping asshole. Robin didn't mind being spat on since lubrication was the secret for great anal sex, and now with her hole and his shaft slick in saliva, they were ready.

"Oh my God...yes," Robin hissed as he entered her bowels once again.

This time she was loose right from the start so Sandy didn't have to go nearly as gingerly. Going balls deep right from the start, he pulled back and started slamming into her asshole with speeds already faster than when she was on top.

"Oh fuck! So deep in your stretched out ass," the older man grunted.

As he held steadfast onto the curves of her hips where her narrow waist bellowed out to create the modest curves, Robin wiggled her booty enticingly for him. The combination of her words and now the side-to-side grinding made the news anchor want to blow his load right then and there, but he held that at bay. Instead he took up the invitation each time by rearing back before spiking her on his spear in her rectum time and time again without fail.

"I love that I can feel your balls slapping against my pussy," Robin cooed.

She continued her steady chorus of telling Sandy to fuck her ass, taking her deeper and harder, which he was more than willing to comply with. He was proud of his vast sexual experience and even though he had cum on her face an hour ago, he couldn't help but feel the familiar pressure building again deep in his loins.

"Such a dirty girl...wanting it in the ass to get ahead at work," Sandy hissed in her ear, his thrusting growing harder but more erratic.

"Oh my God that feels so good," Robin groaned, loving the intense penetration.

Her asshole felt better than words could describe on his dick. A large part of that was due to the fact he could slam as hard and as fast into her brown eye as he wanted and she was up to the challenge. More than up for it in fact as it seemed the more intense he fucked her, the more she moaned and enjoyed it.

His observations of her were extremely accurate as Robin was under him and loving every passing second of the sodomy. She had learnt from many partners that anal sex didn't have to hurt, in fact it could be just as if not more pleasureable than traditional sex. Though his thrusts were getting harder, they were not painful to her, especially with her hand rubbing her clit as furiously as she was doing.

"Fuck, shit, fuck," Sandy said under his breath.

He knew he was going to cum soon but he'd use every trick in his belt to delay it. He drove and deeply then slowly pulled all the way out, kneeling tall above her and looking down at her gape. He did that again and again, each time slower than the last and holding himself out of her backdoor until she started to close up then dove back in.

"Is my asshole gaping wide open for you," Robin asked in her sluttiest tone, knowing the answer.

He went back in and stayed inside her this time but kept going at a slow, almost painfully slow pace. Even that wasn't working though. He had come too far to stop the avalanche that was his pending orgasm and the only thing he could do was embrace it. Which is what he did, ramping back up to thumping his throbbing member back into her ass, forcing her to take him balls deep.

"Oh God! Keep fucking me," Robin demanded, sensing how close he was to cumming.

"Yes, yes, yes...here it comes...UUGGGHHHHH," Sandy grunted as he came deep into Robin's asshole, coating her anus with his spunk.

Robin could feel his dick jerking inside her ass as he held himself balls deep. He made odd howling noises as his jizz painted her inner walls until finally he was spent. He stayed inside her until he started softening, at which point he backed all the way out and flopped onto the bed. Knowing this for what it was, Robin got dressed again, only feeling the cum starting to trickle down her leg before sliding her thong back on to hold it contained until she leaving.

"I look forward to seeing you around the office Robin," Sandy said, holding the bedroom door open for her, a clear sign for her to see herself out.

"So that does mean I got the promotion," she asked, fully clothed once more.

"As long as we agree that every other Thursday we carve out some mentor-mentee time then I think I can offer you the new position," Sandy explained. "And by that I mean my dick making your ass wide open."

"I guess I'll see HR in the morning about my new job details," Robin said, agreeing to her promotion.

    

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