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Show Me How

Summary:

A very depressed and single Dr. Michael 'Robby' Robinavitch stumbles across a sugar daddy website while browsing the internet. While ignoring friends and loved ones' concerns on his well-being, Robby decides to unburden himself from his loneliness by caving and finding a sugar baby for...companionship. As it tends to happen when lines are blurred, things complicate as the arrangement becomes less transactional and much more intimate than Robby could have anticipated.

Notes:

(See the end of the work for notes.)

Chapter 1: prologue

Chapter Text

It was the holidays. That's how it started. From all the festivities and glamorized commercial gifts of the season catered to give to friends, family, and romantic partners. Neither of which Robby possessed. Not anymore. Well, maybe only friends, if he eased up on the dramatics.


Shopping for Jack's birthday was what made him stumble into the situation. Despite nearly three decades of knowing the man, the amount of gifts they'd interchanged could be counted on a single hand. They simply weren't the type of men to give each other presents, and that'd been just fine. Until now.
Robby wasn't sure if he was buying a gift for who he could call his best friend out of genuine celebration for the man's birthday or out of the guilt he felt for pushing Jack away whenever he asked Robby how he was faring. Concern coming from the man who had taken up to standing at the roof of a hospital, mind you, uncomfortably close to its edge.


Admittedly, the website Robby had been skimming while brainstorming what a forty-five year old workaholic would want was rather sketchy. Pop-up ads would occasionally disrupt his browsing, and he'd huff before clicking out and continuing on. He had just come across a pretty nifty Swiss army watch when yet another ad consumed his screen. Rather than loading a betting website again, or another Chaturbate tab that made his face flush, he's instead taken to a website called Sugar Hush. The confusion on his face melts when he reads the introduction on the home page.

'FEELING LONELY? LOOKING FOR COMPANIONSHIP? SOMEONE TO SPOIL, NO STRINGS ATTACHED? FIND A SUGAR BABY NOW BY CLICKING THIS LINK! MEET UP WITH THE GIRL OF YOUR DREAMS AS SOON AS TODAY!'

Instinctively, Robby clears his throat and glances around the room, despite being in the privacy of his apartment. The large 'SIGN UP FOR FREE!' button glows tauntingly while his finger guiltily hovers over the exit button much longer than it should.


Yeah right, he thinks. Sugar daddy websites were for lonely, sad old men that didn't have anyone to spend their 401k on except for young pretty women that would never go out with them otherwise.


After a long moment of taking in the site, he shakes his head and exits out of the page.


You're not that type of guy, Robby, he tells himself firmly.

 


As it turns out, Robby was one of those lonely, sad old men looking for a pretty thing to spoil. Hours later, he remained wide awake in his pathetically empty queen-sized bed, listening to the sounds of the night city breezing in from his open window. Whenever he tried closing his eyes to get some shut eye (even attempting to count sheep, to his scoffing frustration), flashes of the website taunted him, so he'd opted for staring at the ceiling and hoping his exhaustion would eventually knock him out.


Would it truly be so bad to take a look into what being a sugar daddy is like? Was it so selfish of Robby to not want to be alone? To take care of someone else, like he always seemed to want to do to justify ignoring his own needs? Sure, the companionship would be coming from a woman potentially half his age, but how would that be an issue if she was on the website as well? They'd be grown adults, free to do as they please with their money and time….maybe even their bodies, too. The last part makes Robby swallow dryly.


Fuck it.


With a growling huff, Robby sits up and reaches for his laptop. He unfolds his glasses and perches them on the tip of his nose while he logs in. He bites his lip as he clicks on the web link for Sugar Hush, once again greeted by the tantalizing words.


"Ohh, what the fuck am I doing…" Robby mutters, but not once do his fingers stop moving around the keyboard.


Surprisingly, once he got past the shame of typing in his credit card information and ransacking his brain for a normal sounding username to use, cruising through the website wasn't so bad. He typed in personal information that would help the algorithm get a sense of what he might be looking for in the millions of women subscribed.


Name?  Michael Robinavitch. So far, so good.
Age?  As much as he wished it weren't so, he was at the halfway mark, so he begrudgingly typed in the dreaded 50. Actually seeing his age now while doing what he was doing didn't feel great, but he pressed on.
Sexual Orientation?
Robby actually found himself pausing at this question, but ends up just clicking on the heterosexual option, a faint dust of pink on his ears.


That's a problem for another day, he shakes his head. One mid-life crisis at a time, Robby.


And really, how long could a mid-life crisis even last? He'd be over this in a week, if work didn't get between it, he was sure.