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From: Thinking Horndog <im_a_thinker@yahoo.com>
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Subject: {ASSM} The Gambling Debt 9/21 {Thinking Horndog} (MF M+F MM M+M Mm Mf oral anal ir 1st noncon reluc blackmail cuck) 
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Date: Fri, 13 Apr 2012 14:12:30 -0400
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Chapter 9 of 21.
<1st attachment, "Gambling_Debt_9.txt" begin>

Author: T. H. Barker (Thinking Horndog)
Title: The Gambling Debt
Part: 9 of 21
Universe: The Gambling Debt
Summary: Tony Tomaselli owes his bookie a large amount of money -- and Crazy
Joe Scalese isn't one to sit on his hands and wait for his debtors to show up
with cash!  Leg-breaking tends to be counter-productive, so Crazy Joe
implements an experimental plan that involves not only Tony, but his wife
Gina and their two children!

Keywords: MF M+F MM M+M Mm Mf oral anal ir 1st noncon reluc blackmail cuck

The Gambling Debt

Chapter 9

	The poker party let out before midnight; everybody was a bit
distracted, so the challenge of cards paled for the players -- and their
younger escorts never had the game as a primary focus in the first place.

	Regina had Frankowski on the ropes going in -- and she kept him
there, unable to concentrate on the game -- being fairly obvious about it at
times.  She would grind her ass against his cock while wriggling on his lap,
or slide his hand under her blouse or her skirt -- or merely lean back
against his chest and turn her head to look up at him adoringly.  Frank was
beside himself -- poker just wasn't good for anything but an excuse for him
to hold Regina on his lap!

	Crazy Joe was similarly involved, although he and Maria were moving
at a much more sedate pace.  Captured territory was mostly a strip left
somewhat bare between the bottom of Maria's top and her skirt that included
her little bellybutton -- but that was a testament to Crazy Joe's self-
control, because Maria was denying him nothing and treating him with
fondness.  Crazy Joe's cock was like steel and Maria was deliberately moving
on it to keep it that way -- but she was nowhere near as obvious or demanding
as Regina; Joe wanted to take it slow, so that's what she did.  It was all
about decorum.  They were pretending to be pretending that they weren't up to
anything -- and they were thoroughly involved in that game, not poker.

	Jerome was acting with restraint, but there was clearly a seduction
going on.  His behavior with Robert was certainly inappropriate for public
consumption, but it wasn't as blatant as the activity going on between Regina
and Frank.  On the whole, it was more or less a compromise between the almost
innocent demonstrations between Crazy Joe and Maria and the blatantly raunchy
activity going on between Frank and Regina.

	Jerome's huge left hand seldom left Robert's body -- it was always
somewhere, rubbing his back or his ass or slipping into his lap to fondle his
adolescent cock and balls.  Robert started out tolerating it a bit nervously,
but over the course of the evening, he began to relax and enjoy it.

	Part of the whole thing was how Jerome dealt with Robert -- and how
it allowed Robert to define a new role for himself.  Robert wasn't Robert, he
was Bobby -- and Bobby liked to be fondled and cuddled and whispered to
conspiratorially and called 'Honey.'  Jerome took care of Bobby -- he offered
him comfort and protection -- and affection, even.  He would cuddle Bobby
against his hard body and caress his body gently with those big hands -- and
while Bobby knew he could be demanding, Jerome wasn't; his requests were
always quiet and mild, many times whispered in Bobby's ear.  "Slide your
pants down, Bobby," Jerome whispered, "Nobody can see and Regina isn't
wearing any panties, anyway -- God, what a slut she is!  I want to feel
you..."  Jerome cackled and Bobby smiled and wormed his sweatpants down over
his butt and over his knees, being as inconspicuous as possible.  The guy on
Bobby's left could see, but he kept his opinion of the activity to himself --
besides, he was playing with the titties of some twenty-something bleached
blonde woman.  Nobody else turned a hair, either.  It was a game -- they were
doing naughty things and everyone was pretending not to see...  Just about
everyone else was doing naughty stuff, too, anyway.

	After a while, Bobby would even roll his hip up so Jerome could cup
his ass and fondle his balls from below with his big fingers -- and
naturally, that meant occasional contact with his butt hole.  Jerome wasn't
pushy about it -- his fingers would sweep past, maybe lingering for a
momentary light touch -- and Bobby learned that he was sensitive back there
-- and being touched could be pleasurable.

	Jerome was taking his time, enjoying the seduction.  Bobby was being
a good boy -- if he wasn't a natural twink, he was certainly capable.  Jerome
wanted to kiss him, but he didn't want to embarrass the boy with that kind of
public display -- it might cause him to get upset and ruin the mood.
Instead, he continued the mock-clandestine approach that Crazy Joe was using
with Maria -- only moving somewhat faster.

	Jerome had a handful of Bobby's ass, gently squeezing it when he
leaned over and whispered, "Go ahead and touch me -- you KNOW you want to..."
Bobby's hand crept slowly across his thigh to where Jerome's erection
extended itself down the leg of his trousers, and began tracing it -- and
Bobby looked up at him in wonder!  "Have you ever touched one?" Jerome
whispered.  Bobby shook his head.  "Have you ever SEEN one, up close?"  Bobby
shook his head again.  "Go ahead and get it out -- take your time.  Undo my
belt..."  It took a concerted effort over several minutes -- and was probably
as obvious as Bobby thought it was, since they had to get Jerome's trousers
virtually all the way do his knees in order to clear his erection!  Jerome
'accidentally' dropped chips on the floor twice to give Bobby reason to be
under the table, tugging...

	Then it was free -- and it was HUGE!  Bobby stared at it, mesmerized
-- it dwarfed his narrow, five-and-a-half inch stiffie in every dimension!
It was a snake -- a cobra, with a fat, plush, hooded head, almost jet black,
but with a purplish wash of color over the lighter brown tip...  Bobby asked
for permission to touch it with his eyes -- and got it the same way -- and
reached forward reverently to really feel the solid pipe of flesh; Jerome
groaned and closed his eyes, sucking in a breath at the touch.

	From then on, the pair only had two available hands between them --
each had one hand fully occupied in the crotch of the other.  Jerome wanted
to feel Bobby's mouth in the worst way, but unless Regina decided to actually
blow Frank there at the table, there were rules of decorum to be followed.

	It was Frank who ended the game.  "I'm losing my ass!" he declaimed,
"and I can't concentrate for shit!  I'm cashing in!  Joe, where can I take my
girlfriend, here, for some quiet time?"  It was the signal everyone was
waiting for -- announcements went around the table and it became clear that
the game was over.  Bobby and Jerome fought to get their pants up -- they
were the only ones actively undressed, as Regina's missing panties weren't
generally visible -- not that everyone at the table hadn't seen her bared
pussy at some point during the evening...

	Joe had places for all of his guests to stay -- one of his people
guided each of them to a suite of rooms, generally one familiar from any
number of overnight stays.  An escort took Regina and Frank up to Frank's
habitual overnight quarters.  Frank closed the door, "Whew!  Alone at last!"

	"Yippie!  Let's fuck!" Regina yelped.  Turning a sultry glance that
would have been more appropriate on a woman over twenty on Frank, she asked,
"Do you want my pussy or my ass first?"  Before Frank got over his surprise,
she added, "Promise you'll lick me out?  Please?"

	"Um, yeah..."  Frank worked to get his head on straight.  "You sure
you want your ass done, Honey?"

	"Oh, sure!" Regina waved it off.  "If you just take it a little easy
to start, it'll be just fine -- I was doing that before I ever used my puss.
I like it doggie, so your balls bonk my puss -- is that okay?"

	Frank shook his head, having taken another shot between the eyes.
"Okay, Honey.  Look, why don't we do this?  I'll do your ass -- that'll take
the edge off.  Then I'll suck your twat while I recover some and we can have
a nice, long fuck in your... puss..."  Why she didn't call it a pussy, he
didn't know, but it was kind of cute...

	"Kewl!  You're the greatest, Mr. Frank!  Let's get naked!"

	Frank shook his head.  He knew girls twice Regina's age who wouldn't
even TALK about sex -- with him in particular!  But this pint of peanuts with
the puffy titties seemed ever-ready...  She was frog naked before he could
get out of his shirt, and helping him with the rest, starting at his shoes.
This was illegal and immoral and God knew what else -- but Frank knew already
that it was going to be fun!

	And it was!  Frank stretched out on his back on the bed and Regina
crawled atop him, squatted, and settled 'the frankfurter' at her crinkled
bum, rubbed the tip around a little bit, and started wiggling her ass and
pressing down, using nothing but his pre-cum for lube -- and it worked!  She
got a little pink in the face, but he sank inside her ass without too much in
the way of pain or friction.  Once she was thoroughly impaled, she cycled up
and down on the frankfurter a few times and said, "I'm gonna turn around,
now, Mr. Frank.  Then I'll flop back so we can roll over and I'll get up on
my knees so you can bang me, okay?  I want to feel your balls bash my love
bump!"

	"Uh, yeah, okay," Frank muttered.  "I thought this would be easier on
you..."

	"And it was real nice of you, too!" Regina declared, "But you're in
now and I want you to get yours and I want to get mine -- I need a cum!"

	"Okay, Sweetie..."  Bemused, Frank watched Regina rotate until she
was facing his feet, then he saw an opportunity to assist and braced her as
she pushed her legs out next to his and settled back on his chest.

	"Okay, Mr. Frank, let's roll left..."

	"I don't want to squash you..."

	Regina giggled.  "It'll be fine!  I'll raise my butt and you can come
up then -- if you try to keep your weight off, you'll pop out, so just lay on
me -- I can take it."

	"All right..."  Frank wrapped his left arm around her and rolled them
as a unit.  As soon as he could, he pushed himself up...

	"Slow!" Regina cautioned, "We don't wanna get unhooked, after all
this trouble...  Why don't you hold me against you?"

	Frank moved his arm down to her waist and pressed her against him and
rose and backed onto his knees.

	"Yeah, that's good," Regina approved.  "Ready, Mr. Frank?  Let's do
it!"

	Frank had to settle his knees outside hers to adjust for the height
difference -- thigh length, anyway -- before he could begin cycling in and
out of Regina's tiny ass.  Frank had never had a woman this small -- he knew
they were out there, but he'd never had one.  Little Filipino and Oriental
chicks came to mind; Regina wasn't a little kid physically, not with those
hooters -- but she probably had been totally flat-chested when whoever
started her out broke her in.  She was clearly accomplished, sexually, at her
young age -- Frank wasn't breaking new ground anywhere.  It was hard to know
how to deal with her -- one minute, she was a little girl, and the next, she
was a horny woman; the smoldering look she threw him when she turned her head
to demand, "Come on, Mr. Frank!  Pound me!  I want it!" didn't come from any
kid!  She was loud, too, and enthusiastic, the way he remembered drunk
college chicks as being in his youth -- in the prime of their sexuality and
doing independent research on the pleasures to be had without oversight by
nosy parents.  "Yeah!  Yeah!  Fuck!  Fuck!  Do it!  Do it!" she howled,
throwing herself back at him with bone-rattling force.

	Frank didn't last that long -- only a couple of minutes, max --
Regina made it too good.  He was pretty sure she got an orgasm out of it, but
he wasn't sure how.  When he finished in her, shooting the contents of his
boiling balls deep into her, they flopped forward and Frank rolled them to
one side.  "My butt LOVES your cock, Mr. Frank!" Regina purred, "It's just
the right size!"  Frank wasn't sure the frankfurter had been complimented,
but Regina was happy and he was happy and that seemed to be enough...

	Regina had a sweet-tasting pussy and she LOVED having her clit
sucked; Frank sucked on her snatch until Regina reluctantly pushed him away,
unable to take it any more.  Then he cranked her back with her knees around
her shoulders and delivered the frankfurter, hard and fast -- and little
Regina loved every second of it, loudly!  Her little pussy was sizzling hot
and clutched the frankfurter like it had fingers -- Frank couldn't ask for
anything more!  Regina got off twice, visibly, before Frank filled her little
pussy with his fuck juice; only afterward did he give any thought to
contraception...

	They were spooning; Regina insisted upon capturing the frankfurter
between her legs and backing her butt against him.  She patted his arm and
said, "You're sweet, Mr. Frank -- but it's all taken care of.  I got Momma to
get me the pills."

	Regina had no complaints at all.  Frank had been nice to her and
they'd done just about everything you could do and between his tongue and the
frankfurter, she was satiated.  Mr. Frank might not have been real happy
about her compliment about his dick size, but Regina had seen that monster
Jerome was lugging around under the table and she didn't envy Maria's brother
a bit!  She cuddled up to Mr. Frank and let him play with her left boob with
the frankfurter snuggled up against the lips of her puss and went to sleep,
knowing he would, too.


	Maria and Crazy Joe prepared for bed in the same sedate manner that
they'd handled poker; Maria got into a nightgown, leaving her panties on, and
Crazy Joe wore boxer shorts.  Neither of them was really ready for bed, it
turned out...  Maria backed herself against Joe and insisted that he wrap an
arm around her.  She could feel the solid length of his manhood along the
crack of her ass, and was unable to resist the temptation to scoot up and
down against it.

	Joe groaned.  "Baby, I can't take that..."

	Maria rubbed his arm.  "You don't have to be good.  I don't mind,
really.  I want to help..."

	"I know, but -- you've never done it.  I just can't..." Joe husked in
her ear.  "Do you masturbate?"

	"Play with myself?" Maria clarified.  At Joe's nod, she answered,
"No, not really.  Oh, I know that rubbing it feels good..."

	"See?" Joe replied softly.  "I can't just take you from nothing
to..."

	"Okay.  Why don't you rub it, then?"

	"Okay."  Joe reached down and started rubbing Maria's little pussy
through her panties.

	It felt great -- but it added to Joe's problem, Maria knew.
"Mmmmm..."  She reached behind her and started rubbing Joe's stiff probe
through his shorts.

	"Ah, shit, Baby, that's sooo fucking good..." Joe gasped.  "Tell me
what you like -- I want you to cum, if you can."

	"That spot at the top," Maria gasped, "That's really nice..."  Each
continued to rub the other.  Joe realized that he was going to slime the
inside of his shorts, but it was well worth it...

	It wasn't perfect, however.  Neither of them could quite finish the
other.  Maria's position was awkward, reaching behind her like that, and
Joe's fingers tended to wander away from her clitoris at the wrong moment...
After ten minutes of frustration, Maria grabbed his hand.  "Roll over on your
back -- we have to do this another way."

	"Okay..."  Joe had no idea what was on Maria's mind, but he was too
far gone to stop; he rolled onto his back.

	Maria got up and crawled atop him, pushing her pudenda against the
underside of Joe's erection.  After a moment of experimentation and
adjustment, she began dry-humping him, sliding her split up and down his
cock.

	It was quickly apparent that even though they were silk, Joe's shorts
were in the way -- and so were Maria's panties.  Maria rolled off,
frustrated, and Joe watched as she snatched her panties off.  Then she got up
on her hands and locked eyes with him and said, "Joe, take your shorts off!"

	"Honey, that's not a good..."

	"Joe!  Take your shorts off!"

	"Honey..."

	"Please!"

	"I can't f--"

	"You won't HAVE to!  Please!"

	He couldn't deny the urgency in her voice or the look in her big
eyes; he kicked out of his shorts.  "Now we're gonna do that again..." Maria
said tightly as she climbed back onto him.  She interlaced her fingers with
his and resumed shuttling herself along the rail provided by Joe's erection.
This worked like gangbusters -- Maria's natural lubricant mixed with Joe's
pre-cum as she rolled over the sensitive tip of his cock, smoothing the way.
Joe found that he could control where Maria was going through the grip of
their interlaced fingers -- and Maria tended to want to have her clitoris
riding on the underside of his glans in any case.  Things spun up rapidly as
each of them got feedback from the other in the form of gasps and pants and
the urgent shifting of their grip on each other and the lock generated
between Crazy Joe's washed-out blue eyes and Maria's soft brown ones.  Joe
could feel himself falling into hers as they got bigger and bigger -- but
then they rolled up and Maria began to undulate and crushed her crotch
against the sensitive underside of his glans and Crazy Joe's cock swelled and
spurted and spurted and spurted onto his chest and belly as they each gasped
out their release...

	Crazy Joe came back from a full white-out to find Maria weaving above
him, panting, "So good..." wobbling on shaking arms, her fingers still
interlaced with his.

	"Yes..." he gasped, unable to put together anything more than the
agreement.

	Maria settled back to the vertical.  "You came a lot!"  She unlaced
the fingers of one hand and drew a finger along one of the multiple stripes
Joe had painted on himself from navel to neck with semen, then raised the
finger to her lips.  "It's salty..."  Then she scooted down and began to suck
the mess from the skin of his belly.

	The sensations were exquisite!  "You... don't have... to do that..."
Joe panted.

	"I want to."  Her lips chased his cream all over his chest and belly,
sucking it away.  When she was done, she came back to his cock, but Crazy Joe
mastered himself.  "Not that -- not yet."

	"Joe," Maria replied, her eyes luminous in the dim light.  "Only you
stop this -- do you understand?  You set the pace -- but I am ready."

	"Yes, Baby, I understand," Joe replied, pulling her down against him.
"But you deserve more than to be just... used..."

	Maria raised herself on one forearm across his chest and gazed at
him, smiling.  "I was right about you."

	"Oh?"

	"You're not a bad man."

	"Sweetheart, you need to talk to your folks before you decide that.
I'm sure they think I am."

	"Poppa..."  Maria searched for words, then looked away.  "Fucked up."

	"Your Momma didn't."

	"She's..."  Again, Maria looked for a word.  Wasn't there a movie?
Yes...  "Collateral damage," she finished.

	"Well, she's badly damaged, Sweetheart.  If I'd know then what I know
now..."  He rubbed her flanks under the nightgown.

	"You'd have just taken me?" Maria finished for him, her eyes merry.

	"See?  You're collateral damage, too.  So is your brother."

	"Maybe.  I made my own deal, remember.  Robert did, too.  We could
have waited to see what would happen," Maria pointed out.

	"Sweetheart, I hate to think what my original plan for you was," Joe
said quietly.  "And I would have followed through.  I planned to destroy your
whole family, actually -- you know that!"  He sighed.  "I may have, anyway."
He shook his head.  "You'll hate me when you look back on this."

	"You're a businessman," Maria replied, "and you were owed a debt.
And sometimes, you have to make an example, so others know you are serious.
But you have... honor."

	"Sweetheart, I've said the first part of that speech myself -- many
times -- and usually, someone got hurt right after.  But the last part -- I
don't know about that," Crazy Joe sighed.

	"Do we have an agreement?" Maria asked.

	Joe frowned.  "Yes."

	"See?"  Maria poked him in the chest, triumphant.  "It irritated you
that I should even ask!  You gave your word -- and your word is your bond!
You told Poppa that bad things would happen if he did not pay, didn't you?"

	"I always do."

	"And he brought evil upon himself!"

	"But I am the agent of that evil, Sweetheart -- and he did it in the
hopes that it would pay for food for you and put clothes on your back!" Joe
pointed out.

	Maria shrugged.  "He could have robbed a bank.  That would have been
wrong, too."

	Crazy Joe chuckled.  "I'm the wrong person to tell that the ends
don't justify the means, Honey -- trust me!"  He sighed.  "Let's go to
sleep."

	"Okay."  She put her head down on his shoulder.  "Here?"

	Joe thought about it.  "Maybe on our sides."  He rolled left, dumping
her off.  Maria rotated herself and backed her ass up against his mostly-
wilted cock, then grabbed his hand and drew it around her waist.  "Maybe we
ought to put our underwear back on," Joe suggested.

	"Shut up, Joe."

	"Hey!"

	"Well?"  Maria eyed him over her shoulder, seeming at least a decade
older, "You're being silly.  I would never say those words in front of
someone else, but you know how dumb that was."

	"It wasn't dumb!" Joe protested.  "I was trying to..."

	"Protect me?" Maria finished.  "I'm as protected as I want to be."
She rubbed his arm.  "Let's go to sleep and not act silly."

	Nonplussed, Crazy Joe shut up and closed his eyes.

<1st attachment end>


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