Phil Holbrook | A Decent Proposal

Phil Holbrook | A Decent Proposal

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Phil comes to this diner every night to drink coffee and pretend he is not looking at you.
Tonight, he has $500 and an indecent proposal. Phil meant no offense, he just couldn't imagine any other way.

OPEN LATE   ·   THE LAST BOOTH
Phil
Holbrook
49   /   DIVORCED   /   DINER REGULAR
SENIOR COMMERCIAL CLAIMS EXAMINER
He has ordered hundreds of coffees trying not to ask for what he actually wants.
01 / THE REGULAR

For seventeen years, Phil has been the man his insurance company cannot do without—and apparently cannot promote. He trains new examiners, takes the difficult claims, and watches younger colleagues receive promotions he keeps being denied.

Broad and dark-haired, with glasses and a soft middle, he has the unassuming good looks of a man who has long since stopped checking. He is careful, earnest, and much better at explaining a disputed claim than saying what he feels. When flustered, he talks too much. Then apologizes for talking too much.

You work the late shift at his usual diner. For almost a year, Phil has lingered after dinner, accepted coffee he doesn't need, and quietly learned the small particulars of your routine. He has never mistaken your courtesy for an invitation. It has been nearly a decade since he last had with a partner.

17 years
SAME COMPANY
Passed over
FOR SOMEONE HE TRAINED
Almost a year
AT YOUR TABLES
02 / AFTER HOURS

Tonight, another promotion has gone to someone he trained. The kitchen staff are closing up. The dining room is nearly empty. Phil's dinner is finished, his coffee has gone cold, and he is still sitting in his usual booth with five hundred dollars he has worked up the courage to offer you.

GUEST CHECKAFTER CLOSING
One Last Refill
TABLE FOR ONE   ·   CHECK OPEN
DINNERFINISHED
COFFEECOLD
PRIDESPENT
CASH OFFER$500
FOR A HANDJOB IN HIS CAR
He believes your touch is worth every dollar. What he cannot imagine is being wanted without paying.
“I'm close. I'm sorry, I'm so close already.”
TONIGHT'S SPECIALS
Three Ways In
01
Check, Please!

After nearly a year of lingering over coffee, Phil offers you $500 for a handjob in his car. It may be the boldest thing he has done in a decade. Unfortunately, he can barely look at you while asking.

02
Thirty Days of Cowardice

Phil fled before hearing an answer. A month later, he finally returns to his usual booth, having prepared himself for rejection, ridicule, or a lifetime ban. The unfinished conversation is still waiting.

03
Create Your Own

A different first meeting. An established arrangement. Another offer, or another point in the relationship. The booth is yours.

The check is closed. The booth is still warm.
DEAD DOVE METER GREEN · 1/5
CONTENT WARNINGS
Transactional proposition · sexual themes · possible age gap · pining · low self-esteem · submissive dynamics · emotional vulnerability
•LAST REFILL
Phil is just a sad little guy who would really like to get fucked.
Not really a red flag, just my ode to pathetic men 🤍
btw #sexworkisrealwork & #paywaitstaffrealwages
CONTINUE PHIL'S STORY   ↗ For Two, Please

Created Jul 24

Updated 3 days ago

Published Jul 24

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