The Return of the Hustler
By M.C.
Twelve years after a beautiful woman hustler totally humiliated a large, tough, athletic macho man, she unexpectedly returned - and had a surprising proposition for him.


Author's note: Still cooped up in my house because of you-know-what, I've
reread an old story of mine called "The Hustler". I can't believe that I wrote
it nearly twenty years ago! It was posted here on my bookshelf in May of 2000
when we were still young and innocent - that is to say pre-9/11. Tempus fugit.

Anyway, as I was reading it I got the idea to write a sequel. But because
twenty years on seemed like too long a timespan (I'd like the characters to be
in their mid-30s), I decided to make it only twelve. You needn't read the
original "The Hustler" as I will summarize it in the first few paragraphs of
this story (in the first person) but you may if you like. Anyway, hope you're
all maintaining your sanity in this difficult time and please stay well. And
now for the story.

Enjoy,

M.C.

The unforgettable evening when I met Sheila - the hustler It's been twelve
years since I was completely humiliated by Sheila, a beautiful female hustler
who masterfully lured me into a series of athletic contests and then proceeded
to easily beat me in every one of them; culminating in literally destroying me
in our final contest - a wrestling match! I must have outweighed her by at
least fifty pounds and stood six inches taller than she did; and that's not to
mention that I had been a wrestling champion in both high school and college.
And yet she still managed to wipe the floor with me - and in my very own condo
too!

It started out innocently enough with what I thought was a friendly game of
eight ball for a dollar in the local pub that I frequent. But each time she
would beat me she offered to play again - for double or nothing. At first I
thought that she had just gotten lucky in winning the first two or three
games. But after she beat me five times in a row, I began to suspect that
maybe I was being hustled.

But what was really annoying was how Sheila would giggle every time she beat
me; as if she was rubbing it in. Only later did I realize that that was indeed
what she was trying to do - but I was just too full of myself at the time to
see it. She was baiting me and I, naively, was swallowing the bait - hook,
line, and sinker.

"Well, that was fun Richard. I believe you owe me sixteen dollars now if my
math is correct. Right? Care to pay me now? Or maybe you would like to try
your luck at something else?" (This dialogue isn't exactly as it was in the
original story, but I like it better). "I noticed that there's a bowling alley
right across the street. Would you like to bowl a few games?" Then she giggled
again and added, "Maybe you can win your money back; tee, hee." Her giggling
completely blinded me into walking straight into the trap that she was
masterfully maneuvering me into - just as she had intended it would. Like the
master hustler that she was, this beautiful woman was using my masculine pride
and ego against me; and it was working like a charm for her. So we went over
to the bowling alley.

For the first six or seven frames Sheila kept our bowling scores close -
allowing me, a fairly good bowler, to think that I could actually beat her.
But then she turned on the heat by throwing consecutive strikes to defeat me
handedly in each of the three games we bowled against each other. So after
three more defeats at Sheila's hands I gave up. I couldn't beat her at
bowling. "Gee Richard, that makes $128 dollars you owe me. Wanna try something
else? There are some tennis courts right down the street with lights. How
about we play a few sets of tennis? Double or nothing on each set. This is so
much fun; tee, hee, hee."

As I look back upon it now, it was obvious that I was being played by a master
hustler. But, unfortunately for me, my macho male ego prevented me from seeing
what Sheila was doing. And besides, I was a fairly good tennis player. Not
great mind you, but I felt that I was certainly good enough to put this girl
in her place and, there-by, retain the macho image that I had of myself. She
had already beat me at both pool and bowling; (and in the presence of many of
my friends too). How could she possibly also beat me in tennis? I mean after
all, she's just a woman; right? And so I accepted her challenge.

It proved to be a mistake. For after toying with me for the first few games in
each set - and thus allowing me believe that we were more or less of equal in
skill - Sheila then proceeded to crush me with an awesome display of tennis.
Beating me 6-4, 6-3, and 6-3 - and that was after giving me a 2-0 advantage to
begin the final set!

"Gee Richard, it looks like that makes $1,024 that you own me now (remember,
this all began with a simple, seemingly friendly one dollar bet on a game of
eight-ball in the pub only two hours earlier). Would you like to try your luck
at something else? Tee, hee, hee."

"No Sheila," I said with as much humility as I could muster at that point.
"But we'll have to go back to my condo for me to give the money to you because
I never carry that much cash with me." Humiliated now, we walked back to my
condo which was located only a few blocks away.

"My, my, what a lovely collection of trophies you have here Richard," Sheila
said as we entered my condo and she looked over at my large trophy case. "I
see that you're really quite the athlete, aren't you? And look, you even have
trophies for wrestling." She then looked closely at them. "Were you really a
champion wrestler in both high school and college Richard?"

"Yes, indeed I was Sheila." And then I said something that I've regretted
saying ever since. "Would you like to wrestle against me? Double or nothing?"
I was smirking when I said this, thinking that at least when I beat her in
wrestling I could not only win back the money I owed her but also salvage some
of my masculine pride.

My challenge was met by an unexpected giggle. "Gee Richard, I've already
beaten you in pool, bowling and tennis. How would you feel if I also beat you
in wrestling? I mean what a blow that would be to your masculine ego? That
you, a champion wrestler, would also be outwrestled by me; a mere girl. I
don't know if you would be able to handle that.

Maybe you should just pay me what you owe me and let's let it go at that. Tee,
hee, hee." I was totally furious at Shelia now. Yes, she beat and humiliated
me I front of my friends in pool, bowling and tennis. But now she had the
hutzpah to make fun of my wrestling challenge too? I outweighed her by at
least fifty pounds, stood a good six inches taller than she did and not to
mention that I was indeed a champion wrestler in both my high school and
college. What chance could she possibly have against me? "Very well then
Sheila," I confidently responded, "let's wrestle then - double or nothing."

And that would prove to be perhaps the biggest mistake of my entire life. For
despite the superior size and strength advantage that I had over her, Sheila
easily dominated me just as easily as she had at the pool table, the bowling
alley and on the tennis court. In short, she thrashed me; tossing me all
around my living room as she saw fit. And as a final humiliation, this
incredible woman lifted me up with her strong arms, placed me on her shoulders
and whirled me around with an airplane spin before unceremoniously tossing me
onto my trophy case; totally smashing it in the process.

After Sheila took the $2,000 that she hustled me for (generously she let me
off for the hook for the extra $48) she sat down on my chest and brushed her
pretty blond hair.

"I want to thank you for this lovely evening Richard. I had a wonderful time."
Then she leaned over and kissed me on the cheek, gathered up all of her things
and left; leaving my physically beaten and psychologically crushed body lying
in complete shock on my condo floor. (This is where the first story ended).

It took me a long time to finally get to my feet after Sheila left my condo.
Fortunately I managed to hold off crying until she left; there-by salvaging
the tiny bit of what was left of my masculine pride after this amazing woman
had totally crushed me. For although the physical wounds that I had suffered
at her hands from our wrestling match healed within a short period of time,
the psychological wounds that I suffered from the ease in which she beat me in
everything probably never will. In short, Sheila did indeed crush me that
evening; body and soul. Nevertheless, life does go on as they say.

Twelve Years Later

Since that fateful evening I managed to recover most of my pride and
reputation. After all, I could still beat practically all of my friends in
most sports. And I actually improved in the sports that Sheila had beaten me
in. I had gotten a good job at an advertising agency and was making a fair
amount of money. So, all things considered, I was doing rather well in life. I
even managed to put that terrible evening with Sheila behind me; well for most
of the time that is. Every once in a while though I would think about her and
how easily this beautiful woman had dominated me in practically every sport
that I was good at - including wrestling; teasing and humiliating me as she
did.

But for the most part I had moved on. And then ... "Well, well, if it isn't my
old friend Richard. How ya doin?" I was at my local pub (yes THAT pub) facing
the bar with my back turned towards the female who said this. But I didn't
have to turn around to see who it was; her voice had been permanently burned
into my conscience ever since that fateful evening twelve years ago; and it
was the last voice that I ever wanted to hear. Nevertheless I turned around
and found myself staring straight into the beautiful face of the woman who had
so thoroughly dominated and humiliated me. "Wanna play a friendly game of pool
for old times' sake Richard? And I really do mean friendly with absolutely no
money involved." Looking down at her (as I said earlier, I was a good six
inches taller than she was) I forced a smile and somehow managed to say, "Well
hello to you too Sheila.

What's the matter? Have you run out of money? It's only been twelve years."
"Not quite Richard. As a matter of fact I'm doing quite well thank you. But as
I said, it would be a 'friendly' game. In fact I won't even giggle when I beat
you (wink)." Once a hustler, always a hustler I guess, But I accepted her
challenge because, as I said, I had improved since I last confronted her and I
wanted to see if I could take her now; and so we played. "Not too bad
Richard," Sheila said after she deftly sunk the eight ball with a beautiful
bank shot to win her third straight game. "I can see that you've improved
since the last time we played. Wanna try a little bowling now?"

"No Sheila. I can see that you'd only beat me in bowling again too. So what
would be the point?"

"The point would be to simply have some fun. But O.K. I get it. Tell you what
Richard; I'm hungry. So how about I treat you to a nice steak dinner. I
understand there's an excellent steakhouse near-by on Third Street. Are you up
for a good steak dinner on me?" Despite the humiliation that this beautiful
woman had put me through twelve years ago, for some reason I sensed that
something about her was different now; that she actually wanted to take me out
to dinner. And did I mention that Sheila was also gorgeous? So I accepted her
offer; and besides, I never turn down a free steak dinner.

"So Richard," Sheila began as we sat down at our table in the restaurant, " I
hear that you're doing quite well for yourself since we last met. A good
position in an advertising agency, local amateur golf champion three years in
a row. We should have played golf last time (smirk). Maybe we still can - but
it would only be a friendly match of course."

"I see that you've been doing your research Sheila." "All one has to do today
is simply type in a name on the internet and all the information about them
comes up immediately Richard. It really didn't involve any research at all. I
was just curious as to how you were doing since we last met." "Well then as
you know, I haven't done too bad for myself. So what about you Sheila?

Have you given up hustling macho, self-centered, egotistical guys?" "Pretty
much. A few years after our 'encounter' I decided that, since I had
accumulated a rather large nest egg, I could afford to become what I had
always wanted to be. So I enrolled in a good law school and became an
attorney. And because I finished first in my class, I was hired right away by
a good law firm and am now a junior partner. You see Richard, because I was
such a great athlete, not to mention and an expert in martial arts as you may
remember (wink), hustling was just a way for me to support myself while I was
attending university. But because I found it quite easy - and very lucrative -
to lure macho men into athletic contests against me, I decided to do it for
several more years after I had graduated until I had enough money to go to a
good law school.

So you see Richard, hustling for me was always just a means to an end;
although a very enjoyable one at that."

"So what are you doing here now ?"

"Well as I said, I'm a junior partner in a very prestigious law firm and they
recently decided to open up an office here in this city and I was chosen to be
in charge. It's a great opportunity for me so I jumped at it. Then I looked
you up on the internet and found out that you were still living here; so I
decided to meet you."

Shelia paused for a few moments as if deciding on what she wanted to say next.
"Look Richard, I know you must hate me for what I did to you twelve years ago;
I mean who wouldn't.

After all, I not only beat you in pool, bowling and tennis, but then utterly
destroyed you in wrestling - in your own condo. Not to mention smashing you
into your trophy case. The reason I did that by-the-way was because you lost
your cool and started punching me during our wrestling match. That really
pissed me off so I decided to teach you a lesson. And if it makes you feel any
better, I actually felt bad about doing that afterwards. But there's a
cardinal rule among hustlers - never show any sympathy towards the person
you're hustling. I know that must sound very cold-hearted to you.

But as a hustler, showing compassion can have a deleterious effect on what
you're trying to do - which is to take as much money from your 'mark' as you
can." A long period of silence then followed. And it was only after the waiter
brought over our steaks (delicious steaks I should add) that I got up the
courage to ask, "So Sheila, where do we go from here?" A broad smile then
broke out over Sheila's beautiful face.

"Well Richard, I'm sure that perhaps we might come up with something."

Four Hours Later

I lay on my back on my bed with Sheila lying on top of me - Sheila is always
on top. "If you want to be on top Richard, then you'll have to earn it," she
said to me. Yes, we did have a wrestling rematch - and guess who won? Well,
who was on top? Hint: it wasn't me. "You may think that I'm saying this just
to flatter you Richard, but it's the absolute truth. Of all the men, and there
were more than I can count, that I've hustled over the years, I enjoyed
hustling you the most (I honestly didn't know whether to take that as as an
insult or a compliment). I guess that's why I came back to you. I've never
done that to a client before (I would have said victim instead of client). I
mean you were so much fun (did she mean fun to beat up and humiliate?).

"And not to mention very lucrative Sheila."

She looked down at me (don't forget, Sheila was on top) and laughed, "Oh
Richie, do you think that the $2,000 I took from you that day was serious
money? I hate to break this to you sweetie pie, but for me that was just
pocket change. I've hustled rich men for literally tens of thousands of
dollars in a single day. You guys think that you're all so tough; in fact your
macho image is all but built on it. I guess I really shouldn't complain about
it though.

I mean after all, it's that myth that you macho men have about yourselves that
enabled me to put myself through both the university and law school. So I
suppose that I should be grateful for it. But it really is just a myth."

"Sheila, you not only beat and humiliated me in front of my friends in eight
ball, bowling and tennis - and giggled as you did so - but also destroyed me
in wrestling right here in my own home. And now you're telling me that you
enjoyed it?"

Sheila sighed. "You were my mark for that night Richard. A guy who thought he
was the cat's meow as the cliché goes. In other words, the perfect guy for me
to hustle. But did I steal your money from you? Did I pick your pocket? Rob
you at gunpoint? Did I cheat in any of our contests? No. I won them all fair
and square; didn't I? And don't forget, it was you who started punching me
when I was beating you in wrestling; remember?"

(Sheila was right about that. I lost my cool and did start to punch her - not
that it did any good; she still wiped the floor with me anyway)."

"Was it really my fault that you were just too gullible not to see what should
have been obvious to you? Especially after I beat you in tennis. I even gave
you a 2-0 lead the start the third set; remember? And I still beat you 6-3.
But that male ego of yours so blinded you to what I was doing that you even
allowed me to manipulate you into a wrestling match. I hold a black belt in
Ju-jitsu honey. There was never any doubt that I could beat you. I do
apologize for tossing you onto your trophy case though; that was mean. But I
was so pissed off at you for punching me."

A long period of silence followed with Sheila resting her head on my chest.

Then she softly said, "I know this must be difficult for you Richard, to have
me here after what I did to you. But I have changed since we last met. I'm an
attorney now; and a good one.

And your life seems to be progressing well too. We're both in our mid-30s now,
and we're both unattached. So the question I have to ask you is this - do you
really want to spend the rest of your life alone? Could you be happy with a
woman who can beat you in every athletic contest? Because I don't believe in
losing to a man on purpose just to satisfy his ego. It's disingenuous. I am
what I am and I refuse to be anything less than that - a strong, competitive
and yes, very tough woman when I need to be.

So, can you

deal with that kind of woman Richard? Because if you can't then just say so
now and I'll get up and leave. And I promise I'll never bother you again."

One Month Later

I guess I also must have changed. Does the passage of time really make us all
wiser?

Maybe it does. Because I did what I thought would never be possible for me to
do; I actually forgave Sheila for what she did to me. Yes, I forgave the woman
who had totally beaten and humiliated me twelve years ago. She has since moved
into my condo (it was much bigger than the apartment that she was renting),
and shipped all of her belongings over. And I'm not even jealous that Shelia's
athletic trophies outnumber mine by roughly two-to-one. She offered to put
some into storage but, perhaps as a sign of my maturity, I said that that
wouldn't be necessary (we did have to buy a much larger trophy case though).

And despite the fact that our professions keep us both extremely busy during
the week, we always make time on the weekends for, you guessed it, sports. So
far I have yet to beat this amazing 'superwoman' once in anything. She even
defeated me - the three-time city amateur golf champion - by six strokes!
Sheila told me afterward that she wouldn't enter this year's tournament, even
though I told her that it would be all right with me if she did. "That's O.K.
sweetie pie," she said as she playfully pinched my cheek. "I'm not here to
torment you anymore. But I can give you some pointers on how to improve your
game. Your putting totally sucks you know. How many times did you have to take
three putts from twenty feet out today? I think that's something I should be
able to help you with. One of the many things that I learned from hustling
macho, athletic guys is the wisdom of that old golfing cliché: 'You drive for
show, but you putt for doe'. It really is true." Sheila was right about that -
she's a fantastic putter; and my putting does leave a lot to be desired.

Later that evening as we were lying in bed (with Sheila on top of course) I
asked her what else she learned while hustling arrogant men out of their
money. "I learned that the stronger and tougher a man tries to project
himself, the weaker he actually is. You, for example, are a lot stronger now
than you were when we first met the day I hustled you. I deliberately left
here before you started to cry because I saw that you were clearly on the
verge of doing so. And now you don't mind if I have twice as many athletic
trophies as you have on display. And you even said that you wouldn't mind if I
were to participate in the city's annual amateur golf tournament - even if
that meant that I would beat you; as I undoubtably would. To me that shows
both your maturity and your inner strength Richard."

"I'm just accepting the reality of the situation Sheila. Have you ever had any
problems with collecting money from people you've hustled?" "It has happened
occasionally; but I have ways to deal with that problem."

When I asked her how, Sheila giggled (she was looking down at me with her
elbows on my chest and her chin resting on her interlocked fingers) and said,
"Let me tell you about one of the last guys I hustled. He was very, very rich
and thought he was the greatest thing alive - in other words the perfect mark
for me. Well, after I beat him in everything he challenged me at, he owed me
$50,000. Since he said he didn't have the money on him, and I only accept cash
because I've had problems cashing checks, and also because I had another
hustle set up for the very next day in a different city, I couldn't wait
around. So I decided to give him a two week extension to pay me."

"Well, after the two weeks came and went and I didn't hear a single word from
him and he never bothered to return any of my calls, I decided to pay him a
surprise visit. I drove up to his large home in Beverly Hills - with a Ferrari
parked in the garage - and walked in on him. Fortunately for him he was alone
when I entered his home so he wouldn't be embarrassed by what I was about to
do to him."

"And what was that?"

"Well, after he ordered me to get out of his house or he would call the
police, I beat the crap out of him. Although he was a large, strong, athletic
guy like you Richard, he didn't give me too much of a problem. As you found
out, I'm more than capable of taking care of myself (wink). After I gave him a
good beating, I took him across my knees and gave him a good spanking with my
strong right hand on his naked buttocks. I don't think that I ever heard a man
cry so pathetically."

"And did he pay you in the end?"

"Yes. First he wanted to write me a check for the $50,000 he owed me; but as I
said, I only accept payments in cash. Then he said he'd pay me the following
morning when his bank opened. But as that old saying goes, 'fool me once,
shame on you, fool me twice, shame on me'; so I decided you 'babysit' him
until the following morning." Then Sheila began to laugh. "I forced him to
strip off all of his clothes and lie down on his back in his bed. Then I tied
his wrists to the bedposts, stripped myself and used his tummy for my pillow
for the night. And I do have to admit, his tummy made a very comfy pillow;
tee, hee, hee. Anyway, the following morning I drove him over to his bank and
he withdrew the money he owed me. Then I drove him back home. I dispensed with
the kiss on the cheek before dropping him off though as I thought that would
be a bit 'over the top'."

"Do you miss hustling Sheila?"

"Hmmm, that's a very good question Richard. I'll have to think about it for a
bit." After 'a bit' Sheila said, "There are some things that I do miss, aside
from the money that is. I miss the excitement of the start of a hustle when I
begin to manipulate some self-absorbed, macho man into athletic competitions
against me and then proceed to thrash him in one sport after another. I miss
the satisfaction that me, a mere woman as many of them no doubt thought of me
at the start of the hustle - like you undoubtably did when we first met
Richard (smirk) - could crush them in their best sports. Yes, I have to admit
that it was a great feeling - even an erotic feeling - for me to ground their
male egos into dust. Call it a little bit sadistic if you like; but that's
what I felt. Now I get that same satisfaction in the courtroom after I win a
case. So, to answer your question Richard, yes, I do miss it. But it was
getting time to move on with my life. And now, thanks to you and your
forgiving me for what I did to you, I think we can both look forward to a
great future together. But we definitely do have to work on your putting
honey. It's absolutely atrocious (wink)."