Brief Encounter spanking story: ‘The Gambler’

Anthony has sent along another excellent story for the Brief Encounter story contest, and, although he wasn’t eligible for the prize – it’s a great read. Thanks, Anthony!


– Dana

The Gambler


by Anthony


It was finally Ryan’s stop. There was a prolonged screech then he had
to nudge a pregnant woman and three tourists out of the way with his
knee to get out the train doors. The thing is, he thought, if you
didn’t work in the City, you bet your nattiest bermuda shorts that you
didn’t belong on the commuter train during rush hour.


The train wooshed its goodbye, hurtling away to its next destination.


Uh-oh, wait! He turned and beckoned to the almost vanished train.
Something was wrong here. Really wrong.


What should have been a bustling train station, his station, the
station he frequented each work day for better or worse, was
completely empty. Empty as in not a living body within sight.


A white painted sign on the pitted and tagged concrete wall adjacent
to the tracks exclaimed: Nowhere Station.


Nowhere Station?


What the hell had he stepped into now? Furthermore, what deranged
person put graffiti on the wall of Nowhere Station?


That was when he heard the sound. Sound was a charitable word for what
was most certainly a guitar in great pain somewhere down the tunnel:


And the sons of Pullman porters
And the sons of engineers
Ride their fathers’ magic carpets made of steel.
Mothers with their babes asleep,
Are rockin’ to the gentle beat
And the rhythm of the rails is all they feel.


Good God. His day was worsening by the second. Against better
instincts he started walking toward the noise, apologizing to Arlo
Guthrie for what he’d find.


Rounding a bend in the tunnel, he saw a upper-middle-aged man in a
worn herringbone sport coat seated on a concrete step, picking at the
guitar.


“You know, if you don’t practice, it plays hell on your fingers to
start up,” the man said, focusing on his strings and not looking
Ryan’s way. “Kind sir,” the man finally looked up at Ryan, “I broke a
string – would you have five bucks so I can get a replacement?”


Ryan considered offering him a twenty to take up a different
instrument, but said “Where am I? Please tell me you’re a figment of
my imagination.”


“You have arrived at Nowhere. Don’t you think I’m real?”


Ryan just shook his head.


“Are you comin’ or are you going?”


“I take that train every day,” Ryan said. “I’ve never had this happen.”


“I gave up the smokes,” the man said, strumming absentmindedly, almost
pleasantly. “That’s what killed him, you know?”


Nowhere Station was humid this day, and the man was sweating
profusely. He slid his pick between a couple strings in the neck of
the guitar and reached for an accent of red color in his coat’s breast
pocket. Ryan considered offering him a clean handkerchief but quickly
recanted.


“He told me a lotta stuff beforehand though, and you know at the time
it always sounds good.”


Suprisingly Ryan saw that instead of the expected handkerchief, the
man had pulled out a clean and folded pair of red panties and was
ready to wipe his brow with them. The man caught the mistake and shook
his head. “I been doing that more, lately. Like to say it’s because I
gave up whiskey, but there’s a small chance it might also be age
related.”


He laughed and pulled muddied linen from some other crevice that Ryan
didn’t want to know about, wiped his brow and returned the
handkerchief. The man waved the red panties in the air, “I keep these
laundered. They have sentimental value for me.”


Ryan was transfixed by the panties, estimating that they didn’t really
appear to fit the man. The man asked “Ever been on the other side,
young fella?”


Ryan looked from the gyrating panties, directly into the man’s eyes.
Back to the panties. Back to the man’s eyes.


“I’m not sure who you are,” Ryan said slowly. “I don’t even know where
I’m at. I never thought I’d say this…but all I really want at this
point in the worst way is to see the gray walls of cubeland and the
world’s most boring financial spreadsheet on the dismal flat panel
display on my desk.”


“The other side,” the man continued. “You know what I mean? You don’t
always have to give, you know? You can also be a winner on the
receiving end.”


“After I met him on the train coming here and we parted company,
abruptly,” the man reflected, “I thought I’d turn good overnight. Just
like magic.” He laughed. “You know, old man meets young man. A taste
of some advice and then I’m a shark too.”


“Well, I started hanging out here more often, and I met a lot of good
people.” The old man looked at Ryan. “People like yourself that would
drop in for a bit, then leave for Somewhere Else Station.” He added,
“You won’t be staying long here either, my friend.”


Ryan nodded agreement on the first thing the man had said that made sense.


“I didn’t play the guitar so well then, but I always had a deck of
cards with me. So, when they came to the station, always a little out
of sorts, I’d be the Welcome Wagon, the Greeter, and somehow no matter
who it was, we always ended up playing a single hand of poker. For
some small wager.”


“Of course I still got the cards,” the man said, laying the panties
over his leg temporarily and pulling out a boxed deck from his sport
coat pocket, handing them to Ryan.


“I didn’t get good overnight, but I got passable, especially with more
practice. And more confident. I started winning more than I lost.
Anyway, one day a fine young woman dropped in. I remember her
distinctly ’cause she was wearing a bright red dress. Well, and ’cause
of the rest.” He laughed.


Ryan leaned forward, interested despite himself. “Red? You mean red
like the panties?”


That man nodded and continued, “She had short black hair and a lean
frame. Confused like the others, but it wasn’t gettin the best of her.
When I first saw her, she looked short, but then standing next to me,
nose to nose, she musta been at least five and a half, probably three
or four more than that. She was young, but she held herself up in
conversation.”


The man paused his story, scratching at his chin. “I don’t wanna say
bossy, ’cause it wasn’t that exactly. She did have a certain air about
her, though, that made it look like she was used to bein’ listened
to.’


“Anyway, like the others, I friendly-talked for awhile, then when it
felt good I suggested we do a quick, single game of five card draw. I
asked her, I said ‘You do know how to play five card draw, right?'”


“Well, she’d nodded and smiled and told me that where she was from
they played a lot of cards and that it sounded like fun.”


“And get this, my young friend,” the guitar man leaned in toward Ryan.
“She says to me: ‘I’m sure you’ll want to have some type of stakes
involved. I’m afraid I don’t carry much cash, but I do have an idea of
what we could play for.'”


“Well, then she nearly knocked my socks off with a proposition for the
winner. If I won, she said, she’d stand in front of me, and slowly
strip off the exquisite–that was her word, exquisite–silky red
panties she was wearing under her red dress. And that those panties
would be mine for all of time.”


“But get this,” the man continued. “She said the flip side of it was
that if she somehow got lucky and won, and she figured there wasn’t
much chance of that, that I’d have a sore bottom for a week,
guaranteed. Cause she’d take off her black shoe (‘This one right
here’) and bend me over the concrete we’re sitting on right now. Then
she’d lower my trousers and paddle my behind with the sole of that
shoe.”


The man asked Ryan, “Now does that sound like a wager or what?”


Listening to the story, Ryan wondered if guitar man was putting him
on. It was the strangest thing he’d ever heard of and if he ever got
out of Nowhere Station, the happy hour crowd was going to love this
one. Truth or not be damned.


“Honestly, I wanted those red panties bad. I wanted to watch her slide
them down her thighs and over those tight little calves. And to see
her lift each high heel, one at a time, to step out. I wanted to see
how that beautiful red dress clung to her tight bottom as she bent
over to pick up the panties and hand them to me.”


The man reached in his sport coat, retrieved the handkerchief, and
wiped his brow again.


“I know what you’re thinking and you’re wrong. You’re thinking that
this proves that every so often the good guys do win and that life
does have a few happy stories.”


“Well I let her deal, and it sure started right. I was anything but
out of aces – in fact, she’d dealt me not two of them, but three. And
all that before the draw.”


“Well, of course we weren’t playing draw the way it’s normally done,
with an opportunity to add to the pot, bluff, and so on. And I don’t
know why I did it, but when I saw the three of a kind, I leaned over
to her and said, ‘I much would like to see those panties, but if you
want to fold now, we’ll call it off and forget we ever started this
game.'”


Ryan saw humor flare in the man’s eyes as he continued. “Well,” he
said, “she wanted nothing to do with that. She was going to start what
needed to be finished, and she wanted just one card.”


“To make a long story short, when we flipped ’em I still had those
beautiful three aces, but she had something better. She had a lot of
hearts. Lots and lots of them. Enough that it made my stomach churn.”


“I’ve thought about it since. She wasn’t much surprised about the
outcome, but she did mention how those hearts almost matched her
dress, and the panties that I couldn’t see. But then she said that
what the cards were going to match most would be my red hot bottom
when was done spanking me.”


The man stopped for a bit, cocking an eye at Ryan. “I’ve always kept
my word. And I did so on that day as well. She spanked hard and fast
and I squirmed like a little boy. And the shoes off those dainty
little feet put a lot of hurt in my backside. The only thing she
really said as she paddled me was ‘I’ve done a little bit of this
too.'”


“Well, my friend, the story does have a happier ending.”


Ryan noticed that train tracks below were starting to vibrate, only
slightly now, but the man noticed as well. He nodded at Ryan.


“Happy, just like your story’s gonna end. Anyway, when she was done,
she gave me one last hard smack on the behind, this time with her
hand, which hurt nearly as bad as the shoe, and then she almost had to
scrape me out of a ball. My eyes were running. True to her word, I
couldn’t sit comfortable for a long time. But what she did, as I knelt
there looking at her, she slid out of those silky red panties in the
most graceful way, she lifted them up in front of my eyes, then she
slid them into my pocket as slick as all get out. And I’ve had ’em
ever since.” The man smiled and nodded at Ryan.


The tracks were rattling noticeably and Ryan saw an opportunity. “I’m
late for work,” he told the man, rising to his feet and starting back
where he had departed the train.


As he turned back over his shoulder and yelled “Thanks, but I don’t
believe you!” Ryan heard the terrible guitar burst back into action
and somewhere among the screeching he picked up a few of the words:


…
if you’re gonna play the game, boy, you gotta learn to play it right.
You got to know when to hold ’em, know when to fold ’em
Know when to walk away and know when to run.


before the rest was lost in the roar of the approaching train.