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From: Thinking Horndog <im_a_thinker@yahoo.com>
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Subject: {ASSM} The Gambling Debt 7/21 {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 13:10:06 -0400
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Chapter 7 of 21
<1st attachment, "Gambling_Debt_7.txt" begin>

Author: T. H. Barker (Thinking Horndog)
Title: The Gambling Debt
Part: 7 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 7

	Meanwhile, Crazy Joe's guests were arriving for the poker game.
Hammer had picked up Regina from school on schedule -- and Joe had had an
office girl give her mother a call confirming her arrival -- supposedly at
the Tomaselli home, but in actuality at Crazy Joe's retreat in the high-rent
district at the edge of town.  Then Hammer went out separately for Maria and
Robert.  Maria asked Hammer for some insight into exactly how she should
dress, and got, "Like a little girl.  Put on a dress and some cute cotton
panties -- nothing too sexy.  Dress like you did when you were eight.  Buckle
shoes and ankle socks would be nice, but whatever you can turn up.  You
aren't a big girl for this.  No bra -- you don't need one, and you want to be
too young to wear one.  If the outfit is accessible, that's nice, but you're
not there to act slutty -- not going in, anyway.  Let Crazy Joe bring out the
slut in you -- don't bring it to the table."  Maria absorbed this, reflecting
that it was all good advice.  "Take some pajamas or something, too," Hammer
added.

	"What about me?" Robert asked.

	Hammer pursed his lips.  "Good question.  You're more of a display
piece -- and if I know Jerome, you're gonna get groped.  Nothing tight -- a
track suit or lounge pants over some running shorts or something.  Got
anything tight and sleeveless for a shirt, like a wife-beater?"  Robert did
have a couple of sleeveless shirts, so he got into one with a band logo on
it.  "Is your shit swinging free?" Hammer asked as he eyed the result.
"Jerome will probably spend half the night with his hand on your dick.  Bring
a second outfit, in case..."

	The pair rode in the back; Robert took the opportunity to say to
Maria, "I'm pretty sure I'm gonna be doing a lot of gay stuff tonight.  Crazy
Joe has promised he'll provide me a girl at some point, afterward, but I'm
kind of scared about how I'll come out of it.  It's going to be embarrassing
for me -- and for you..."

	"I'm going to be on Crazy Joe's lap and he's going to be touching
me," Maria countered.  "I want you to understand that it's my job to enjoy
it.  I'm gonna be good for him -- anything he wants.  Don't get upset!"

	"I won't," Robert promised.  "It's all about getting the money for
Mama and Poppa.  I'm going to be doing my best to have fun, too -- I don't
think I'm gay, but I think I can enjoy this if I don't get too embarrassed.
Please understand..."

	"You do what you have to, Big Brother.  I understand," Maria
insisted.

	"Thanks.  You, too."  Their minds at ease, they settled back to
finish the ride in silence.


	Maria settled into her role immediately on arrival, dashing up to
Crazy Joe and saying, "Hi, Uncle Joe!  How's my favorite guy?" -- and tugging
his hand so he would lean down for a buss on the cheek.

	Crazy Joe was delighted!  "Hi, Maria!  How's my favorite girl?"

	"I'm just fine, Uncle Joe!  When do we play cards?"

	"In a little while, Hon.  In a little while."  Crazy Joe cuddled her
to him.  "Who does your wardrobe?"

	"This old thing?" Maria giggled, spinning in a circle to display her
skirt and the tank top that was just a touch too short.  The outfit wouldn't
have sparked much comment on her at nine or ten, but the bumps under the top,
small as they were, might have caused her mother to require Maria to dig out
a bra.  The top wasn't a midriff -- it was just a tiny bit too short,
revealing a VERY narrow strip of skin -- and the skirt was a wide item that
technically went almost to the knee -- but it flared, showing a bit more than
that.  Maria didn't possess ankle socks, but she had the type that didn't
show much, only covering the foot itself -- and sneakers.  The result was the
look of a young girl in play clothes -- and growing out of them.  If
anything, Joe would have preferred different footwear, something Maria picked
up on right away.  "I have some sandals, in case my feet get hot.  "Want to
see?"  She dug in her overnight bag, producing a pair of white sandals with
wide straps.  "What do you think?"

	Crazy Joe pursed his lips.  "We wouldn't want your feet to get hot."

	Maria took them and ran to sit on a chair, then deliberately raised
her legs high, one by one, while pulling off the sneakers, displaying her
panties.  Crazy Joe settled into a chair across from her to watch, enchanted,
thinking, 'How does she do it?  She has to be acting, but she's perfect.
Such innocence...  And pink cotton panties with hearts...'

	Maria looked up while buckling on a sandal, "Is Regina here?"

	"Yes, she is, Honey," Crazy Joe confirmed.  "She's playing out back.
When you're done with that, why don't you get Hammer to show you where she
is?"

	"Okay, Uncle Joe."  Maria had her foot on the chair seat while she
buckled the sandal, making sure he got a panty shot.  "As soon as I do this."

	"Take your time, Honey."  Crazy Joe watched her avidly.

	Maria didn't artificially extend things -- she finished and got up,
gave Crazy Joe another peck on the cheek, and took Hammer's hand.  "Will you
take me back to Regina, please?"

	"Sure, Honey."  Hammer shook his head -- this one was SOMETHING!  He
led her off.

	Crazy Joe shook himself and turned to Robert.  "That probably works,"
he noted, eyeing Robert's outfit.  "Did you clean yourself out?"

	"What?"

	Crazy Joe nodded to himself.  "Getting fucked in the ass is messy,
boy, unless you empty yourself out first.  Ever had an enema?"

	"A couple of times, I think," Robert offered, uncertain.

	Crazy Joe nodded.  "You'll do it again, then."  He waved at a minion.
"Get Michelle."

	Michelle turned out to be a bleached blonde, not overdone anywhere,
in her mid-twenties.  "Take Robert, here, upstairs to one of the bathrooms
and give him an enema or two.  Clean him out good -- he's gonna be meeting
Jerome tonight.  Oh, and make him happy about it, WITHOUT giving him a nut.
I promised Jerome a virgin."

	"I... don't think I understand, Joe," Michelle muttered.

	"Simple.  Fill him up, then suck his dick or jack him or something so
he has some feminine attention to take his mind off the cramps and shit," Joe
explained.  "Just don't let him get a nut.  Let him play with your titties or
something.  He's worried that when Jerome gets done with him, he won't be
attracted to women or something -- you might end up being his first piece of
pussy."

	Michelle eyed Robert.  "How old are you?"

	"Fifteen," Robert replied forthrightly.

	Michelle turned a dubious glance on Crazy Joe, who frowned at her.
Turning to Robert, he asked, "Do you jerk off?"

	"Yes."  Robert blushed.

	"And you squirt baby juice, right?"

	"Uh huh."

	"See?  He's qualified.  You worry about doing what I tell you to do.
You're not exploiting him -- I'M exploiting him and JEROME is exploiting him.
You're giving him what every boy his age wants -- right kid?"

	"Yeah."  Robert nodded.

	"Be nice to him.  Show him a good time -- without going overboard.
Handle it."

	Michelle pursed her lips.  "Okay, Boss.  Come on, Honey."  She took
Robert's hand; Robert scrambled to grab his overnight bag and let her lead
him off.

	Crazy Joe chuckled to himself, thinking, 'Of course, he's gonna
associate having a gutful of water with being horny like a motherfucker...'


	Maria was out back on the deck with Regina.  "How's it going?" she
asked the redhead.

	"Great!  I can't wait!" Regina gushed.  She eyed Maria.  "Nice
outfit!"  Regina was wearing a red rubber-band type top that accentuated her
small, puffy breasts and showed lots of midriff, a short skirt and flip-
flops.  Her hair was in braids, but that was the only thing about the outfit
that made her look young.  "Crazy Joe has to love that look!"  Regina grinned
and added, "I'm shooting for something else..."

	Maria nodded.  "I know."  She bit her lip.  "Look, my brother is
gonna be there, too -- with this gay guy.  Robert isn't gay, but he's doing
what I'm doing, you know?  Please don't mess with him about it."

	"No, I get it."  Regina eyed Maria.  "Look, do you LIKE Joe?"

	"Well, I know my folks aren't happy with him -- but he hasn't done
anything to me," Maria replied, "And I think we understand one another.
Yeah, he's okay.  I plan to have fun if I can.  I'm gonna try to see to it
that he does, too, but I don't think he's gonna make it hard on either one of
us."  She smiled.  "I like the look he gets on his face when he looks at me."

	"You're gonna be fine -- I can tell!" Regina enthused.  "Look, I'm
gonna want to play with my man -- I hope you understand.  I like sex stuff --
it's fun!"

	"We're all doing what we're here for," Maria replied.  "Some of it
maybe we wouldn't be doing if things were different -- but we're here.  Let's
just have fun, okay?"

	"Okay!"


	Meanwhile, Robert was having an odd time of it.  Enemas were
unpleasant at a minimum, and sometimes downright painful -- but Michelle's
bare titties were wonders of nature that he couldn't get enough of!  She
played with his cock and balls some, but he was pretty hair-trigger, so after
she squeezed the base of his cock a couple of times pretty harshly to keep
him from spraying, they decided to limit themselves to allowing Robert
exploratory rights above her waist.  She filled him, twice, from the big red
rubber bag with the tube, flooding his cringing ass and gurgling water
through his intestines -- and then lay on her back on a towel on the tile
floor in a position where Robert, who was on all fours, could reach the
gravity-flattened cones of her breasts with his hands and mouth, counting out
ten minutes by the clock each time for Robert to suffer while being
transported by the joys of discovery of a forbidden area of the female form.

	At the end of the exercise, he showered, emerging clean inside and
out, and relatively happy with his lot.  Michelle returned him to Crazy Joe's
presence -- and Joe's first question was for her, rather than Robert.  "So,
how bad was that?"

	Michelle dimpled.  "Well, it was kinda cute, actually.  I think maybe
I have a little more respect for young guys..."

	Crazy Joe chuckled.  "And you?" he asked Robert.

	"The enemas weren't fun -- but Michelle was... very nice..."

	"What do you figure the chances are that you won't like women?" Crazy
Joe asked.

	"Um, pretty poor," Robert admitted.

	"Well, be careful, now, and don't let Michelle's little demonstration
turn your head in the wrong direction about what you're gonna do tonight,"
Crazy Joe admonished.  "You need to give Jerome the same break you gave
Michelle -- actually, you need to bend over backward a little!"  'Or maybe
forward...' he added to himself.

	"I understand," Robert nodded.

	"If you kiss off one sex, you might find that you're tossing off half
of your future opportunities to get your dick wet," Crazy Joe noted.  "I'm an
old guy and it's too late to change, but if I was your age, I might have
played both sides..."

	Robert nodded again, thoughtful; Crazy Joe left it at that, moving on
to,  "Why don't you help Michelle lay out the chips and drinks and stuff?"

	"Sure."


	Frankowski arrived first.  Crazy Joe sent Robert after the girls, who
were more than happy to get started with their evening.  "Regina, this is...
Frank..." Crazy Joe introduced them.  Frankowski's real name was Leon -- but
nobody called him that.  "Frank is your date for the evening."

	Regina turned on the charm, smiling hugely.  "Hello!"

	"Yeah, hey -- hello!" Frank responded, bemused.  "Ain't you pretty?"

	"Why, thank you!" Regina beamed.  "My!  You're a BIG guy!  I'm gonna
have a lot of fun sitting on YOUR lap!"  She leaned close and in a stage
whisper added, "I squirm a lot, you know -- you might have to hang on real
tight..."

	Frankowski was incredulous!  "W--well, I'll be sure to do that!"

	"Goody!  Let's go pick a chair!"

	"Uuuhhh, you run along, Honey -- I'm right behind you.  I need to
talk to Joe for a second..."  Frankowski watched Regina toddle off, bemused,
then turned to Crazy Joe.  "Is she for real?"

	"According to her, she's been fucking around since she was ten,"
Crazy Joe related.  "I stuck a finger up her -- didn't I, Honey? -- and she
offered to let me finger her asshole, too..."

	Maria solemnly nodded confirmation.

	"Either she's the world's damnedest liar, or she's here to fuck,"
Crazy Joe added.  "Have a ball..."

	"What do I owe you?" Frankowski asked.

	"Let's call it three for full service.  If she rolls over and fails
to provide anything willingly, we'll wipe the slate -- and you can just take
it."  Crazy Joe shifted his glance to Maria, who nodded thoughtfully,
indicating that she thought it was fair.  "She's gonna play, though -- she
asked to be here.  I'll probably keep the money in a fund for her or
something -- maybe she can start a school for little Lolitas with it..." he
added, chuckling.  He turned to Maria, "Why don't you go into the poker room
and make sure that Regina doesn't settle into the big chair on the end --
that one's ours."  Maria nodded and left after coming forward to give Joe a
peck on the cheek.

	Frank waited until she was out of the room to say, "I CAN'T BELIEVE
you said that, right in front of her!"

	Joe just shrugged.  "If there is a stupid bone in Maria's body, I
haven't found it.  She's fourteen going on twenty-four.  That girl knows
EXACTLY how our little game is gonna be played, and she's as prepared as she
can be and still be a virgin."

	Meanwhile, in the 'poker room,' Maria thought it incumbent upon her
to say something to Regina.  "Mr. Frank is impressed, but he wonders about
you.  Uncle Joe made promises -- including one that you would play whether
you want to or not."

	Regina waved it off.  "Everything will be fine -- I'll take good care
of Mr. Frank -- I like him already!"  When Frankowski entered the room
moments later, Regina went right up and took him by the hand and said, "Come
on, Mr. Frank, let's go cuddle somewhere."

	Ten minutes later, they were back.  Regina went to the sideboard and
collected a coke, opened it, took a swallow and swished it around in her
mouth for a bit before swallowing it, then asked, "Now can I kiss you again,
Mr. Frank?"

	Bemused, Frankowski muttered, "Sure you can, Sweetie..." and bent a
bit to accept a kiss that clearly had a lot of tongue action in it.  When
they'd finished, Frankowski said, "Why don't you keep our chair warm while I
greet the other guests with Joe -- okay?"

	"Okay.  Regina settled onto the chair and eyed him sidelong.  "Hurry
back..."

	"Oh, don't worry..."  Frankowski wandered out.

	"See?" Regina wrinkled her nose and giggled.  "Mr. Frank is AAAAALLL
taken care of..."


	Meanwhile, Frankowski chased down Crazy Joe.  "WHERE did you GET
her?" he erupted.

	"Why?" Joe eyed Frankowski, wondering what could have happened in so
short a time.

	"Maria must have said something, because no sooner do I get in the
room than Regina grabs me by the hand and says, 'Let's go cuddle!'"
Frankowski related.  "The next thing I know, we're on the couch in the den
and I've got one finger in her twat and one in her asshole, pumping -- the
little bitch wasn't wearing no panties -- while she swallows my cock!  I've
had REALLY expensive whores give me worse blowjobs, too!  So I bust a nut and
she creams on my fingers and she thanks me for the cum and surfaces some
Kleenex for me to wipe my fingers with while she tucks the frankfurter away
and we go BACK to the poker room, where she rinses her mouth out with a coke,
then proceeds to shove her tongue down my throat!"

	Crazy Joe laughed out loud!  "So, she's good?"

	"Fuck!  I want one just like her!"

	"She ain't mine," Crazy Joe admitted.  "Not in any permanent way,
anyway.  Maria found her -- or vice-versa."

	"Well, if the rest of the night goes like that, I owe you -- BIG
time!" Frankowski declared.


	Two out of three of the other players brought their own entertainment
in the form of escorts in their twenties -- Regina dismissed them as 'old
hags' with a sniff and a wave.  The third came alone and was envious of
Frankowski as Regina slithered all over his lap and insisted that she hold
his cards so he could bet with one hand and fondle her little titties with
the other.

	They'd already started when Jerome finally arrived.  "Sorry," he
apologized, "I had to give Leticia a lick upside her head.  She thought tips
were hers to keep..." He rolled his eyes.

	"Well, she gets tips for doing a good job," Crazy Joe rumbled.
"What's the harm?"

	"That shit sounds good until you try it, Joe," Jerome argued, seating
himself.  "In the first place, if you give a woman very much money at all,
she'll find some way to get her ass in a jam with it -- and in the second, if
you get soft with them at all, they think you've gone soft in the head --
then you have to re-educate them, which costs you money 'cause they can't
work while they heal up.  And they whine about how they didn't know...  Trust
me -- it don't work."

	"You're dealing with the wrong kind of women," Joe began.

	"Well, DUH!" Jerome cut him off, popping his eyes.  "They're WHORES!"
Several of those present laughed; Joe grinned a bit, himself.  The escorts
looked a little miffed -- but it wasn't their place to open their mouths in
THIS forum...

	Robert, having visibly nerved himself up, circled the table to
Jerome's seat, "Can I get you something to drink?"

	"Well, hel-looo!" Jerome took in Robert's youth and his curly black
hair and his narrow form.  "What's YOUR name?"

	"Um, Robert..."

	Jerome grimaced.  "So formal!  You should be a Bobby!  Can I call you
Bobby?"

	"O--okay."

	"Come here and let me look at you -- no, go to the barmaid and have
her make me a BIG Cape Codder and be sure to bring it back!  I think we
should get to know one another, don't you?"

	"Uh huh," Robert nodded, then backed away cautiously and turned
toward the bar.

	Jerome turned to regard Crazy Joe.  "He's precious!  Where did you
find him?"

	"Actually, he's Maria here's older brother.  Say hello to Jerome,
Honey."

	"Hello, Jerome," Maria said, politely.  "Pleased to meet you."

	"I'm pleased to meet YOU, too!" Jerome responded.  "You don't mind if
Bobby sits with me, do you, Dear?"

	Maria cocked her head and managed to sound innocent while her eyes
projected a somewhat more worldly expression.  "I think that will be fine..."

	"Oh, dear!  I underestimated you, didn't I, Honey?  Did I
underestimate Bobby, too?" Jerome asked.

	Maria took that under advisement.  "Maybe not."

	"I'll be gentle," Jerome promised.

	"Okay," Marie nodded.

	Jerome popped his eyes at Crazy Joe, who grinned.

	Robert was back.  "I have it..."

	"Come sit right here on this stool beside me, Bobby," Jerome purred,
patting the seat, "and we can get to know one another.  Just put the glass in
that ring there..."  Robert gingerly did as he was told -- and the very next
thing to happen was Jerome wrapping an arm around him and hugging him to his
hard, muscular frame.  "So, Bobby, where are your parents?"

	Robert froze.  Crazy Joe answered for him smoothly, "They're out
tonight, working.  I'm babysitting."  He smiled.

	"Oh, I see..." Jerome knew a forbidden subject when he stumbled
across one.  "So how old are you?"

	"Can we play cards?" somebody rasped.

	"Fine."  Jerome glared at the grouch.  "Deal me in.  Usual table
stakes?" he asked Crazy Joe.  Joe nodded.  Jerome fished and envelope out of
his pocket.  "Bobby, Honey, take this to the barmaid and get me some chips."
He released his grip on Robert, who climbed off the stool without managing to
appear hurried -- and was back in plenty of time for Jerome to drop the ante
in the pot.  "You hold the cards, Honey, like your sister and the other
girl," Jerome directed, pulling Robert back in.  "I want to rub you a little.
Is that okay?"

	"Sure," Robert croaked.  He sat there, picking up cards, rearranging
them according to Jerome's pointing finger while Jerome's other big hand
wandered around under his shirt.  Jerome was totally different from Michelle
-- but there was something about the aura he gave off... something sexy...
Robert relaxed and let the hand wander where it would.

	Maria and Crazy Joe, who were both watching, relaxed, also.  Maria
settled back against Joe and turned her head to kiss his cheek and Joe ran
his hand over her bare belly, just under her top.  Things were going well
with Robert, so they could stop worrying, for now.

	Regina sat on Frank's lap, smiling a Mona Lisa smile and panting a
bit through her nose; Frank had his middle finger buried deep in her pussy,
rubbing her inner lining and her clit both.  After a minute or two, Frank had
to clamp his hand over hers to keep her from dropping his cards while her
eyes rolled up and she shook like a leaf and panted through her nose like she
was running a marathon.  Everybody stopped to watch until she flopped back
against Frank and whispered, "I owe you a big one for that, Mr. Frank..." and
kissed his cheek.

	Jerome's hand moved south during the next hand.  When it was over, he
leaned over to Robert and murmured, "Bobby, Honey, run in the other room and
get rid of those gym shorts -- they're in the way."  Robert nodded and got up
to do as he was told, apparently unconcerned.  Jerome was more than pleased
when he returned, his sweatpants somewhat tented, and climbed back up on the
stool.  From Robert's perspective, the results were well worth the effort, in
no more than a minute, Jerome's big hand was fondling his cock and balls.  "I
want that," Jerome whispered in his ear, "But it isn't polite to suck cocks
at the table, so we'll wait..."

	Uncle Joe's hands wandered all over Maria, keeping away from places
that were patently naughty, but possessing her, nonetheless.  Maria found
herself wishing that he would do more -- Regina was OBVIOUSLY having the time
of her life -- but she schooled herself to patience.  Wiggling a little on
the hard ridge tenting Uncle Joe's lap was allowed, however, and she took a
certain perverse pleasure in making sure it STAYED hard...

	And cards fell and were flipped over and bets were won and lost and
chips clinked and they moved from player to player, depending on who won the
most recent pot...

<1st attachment end>


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