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Subject: {ASSM} The Gambling Debt 12/21 {Thinking Horndog} (MF M+F MM M+M Mm Mf oral anal ir 1st noncon reluc blackmail cuck) 
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Chapter 12 of 21.
<1st attachment, "Gambling_Debt_12.txt" begin>

Author: T. H. Barker (Thinking Horndog)
Title: The Gambling Debt
Part: 12 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 12

	Tony was sitting on the upper level of the sauna, so Gina spread a
towel across the lower level and stretched out flat on her back  Neither of
them bothered to cover up.  They were quiet for a bit, then Gina ventured,
"This is nice."  Tony nodded agreement.  After another long moment of
sweating in silence, Gina said, "I'm thinking about getting a tattoo."

	"Oh?"  Tony blinked.

	"Yeah.  I know what I want -- it's all about placement."

	"Oh?"

	"Yes.  I'm thinking, 'slut,' in some nice, cursive script.  Placement
is the issue, though -- I need to be able to hide it sometimes, but make it
highly visible to strange men."  Gina's eyes glinted.  "Maybe you should get
one, too -- one that describes you.  'Wimp' or 'cuckold,' maybe -- no, that
doesn't quite cover it.  'Bitch,' I think..."

	"Gina!" Tony erupted.  "Dammit!"

	"What?" she flared.  "Okay, I'm mad!  What are you gonna do about
it?"

	"You're not the only one!  And from the sound of things, you'll be
getting even for a long time," Tony rasped, "A LONG time!"

	"Well," Gina backed off, "Getting even, as you call it, takes a toll
on me."

	"I'm sure.  How are you feeling?" Tony shifted to being solicitous.

	"Better than when I got up.  My mouth hurts, and I probably look like
that Jolie woman, and my ass is sore.  I'm surprised my cunt isn't worse..."
Gina complained.  "How about you?"

	Tony worked through his surprise at Gina's term for 'vagina' -- he'd
never heard her say that word in their entire married life together!  "Well,
I don't have a... cunt... but the other two places are sore, for the same
reason.  The rest of the injuries, well, aren't visible."

	"Oh?"

	"It'll be a while before I re-grow any pride," Tony related.  "Bikers
and blacks are going to be hard to look in the eye.  And if you think I don't
feel any guilt..."

	"Martin said something," Gina replied.  "I gather that I'm supposed
to fuck guys, but..."

	"Yeah.  It doesn't quite put you in the same place," Tony confirmed.

	"How bad is it when you have to?" Gina asked.

	"You're supposed to resist to the bitter end," Tony said dully.
"You're supposed to die first.  It's... ugly... when you realize that you
don't have the guts..."  He gazed at the door, not really seeing it.  "Martin
and Scott had me tied down -- I couldn't do anything.  But last night..."  He
paused again, for a whole minute.  "A couple of kicks in the balls and I
rolled over like a... pussy..."  He shook his head.  "They didn't just work
on you that day -- they worked on me, too.  They didn't use drugs -- they
didn't have to.  They used you -- and they used me.  They didn't break me
then, but they cracked the shell -- and they taught me that I could do those
things.  So when I was lying there, holding my crotch, I remembered that
doing those things didn't hurt as bad as having my balls mashed, and coward
that I was..."  He covered his face.

	Gina reached up and touched Tony's calf.  "I'm still mad, and I still
may never forgive you, but -- well, I didn't understand.  I guess it IS
different..."


	An hour later, Gina and Tony were home.  Tied up in their own issues
as they were, they didn't notice anything amiss with Maria or Robert --
although, frankly, Robert was the only one showing any symptoms.  Maria was
at peace with herself over her decision and the consequences.

	Sunday was spent in mutual avoidance -- nobody wanted much to do with
anyone.  Monday, the kids went off to school and Tony went off to work, and
Gina gave a sigh of relief that they'd made it through the weekend somehow.


	Regina had been bothered some by her mother's comment on Saturday
morning.  The whys and wherefores of her parents' breakup weren't clear to
Regina -- it had been explained to her as 'Daddy doesn't love Mommy anymore'
when she was seven and she'd not revisited the subject, but it seemed to be
about something that Daddy either had or had not been giving Momma.  Daddy's
temporary replacement -- a guy named Fred -- seemed to keep Momma pretty
happy, despite being pretty demanding -- and he'd been pretty good at sex,
Regina had to admit -- but then THAT had been a problem with Uncle Mark...
At this point, Uncle Mark was probably wondering why he had intervened in the
first place, since now HE was playing sex games with Regina when he could,
but he'd broken Momma and Fred up and now Momma was alone again.  Momma
generally didn't talk about money, but she'd let it slip that Daddy was out
of work -- or supposedly out of work, as Momma put it -- and the child
support wasn't coming in the last couple of months.  Since Momma seemed to be
seriously thinking about sex for money as a way to tide them over, Regina
thought that maybe she should lend a hand...

	Regina cornered Maria after first period.  "Do you know what Mr.
Frank does?"

	"Well, no," Maria admitted, "but it's probably illegal.  Uncle Joe is
a bookie -- and I KNOW THAT is illegal..."

	"Do you think he has hookers working for him?"

	"I honestly don't know..."

	"Can you ask Uncle Joe?"


	So Maria got on the cell phone.  Joe was tied up, so he said, "We'll
talk about it when school gets out, okay, Honey?  Bring Regina around..."
Maria related this and the girls were both waiting when the limo pulled up.
Robert was, too -- but he hung back until the car arrived and then got in
quickly, up front with Hammer.

	"So what's up?" Joe asked Regina.

	"Does Mr. Frank have hookers?" Regina asked.

	Crazy Joe cocked his head.  "You're a little young.  You could have
quite a career, but I wouldn't put you on the street..."

	"Me?" Regina blinked.  "I don't think it would be as much fun.  No,
Momma is talking about it.  Daddy is out of work and not sending money, and
things are getting tough -- and I think Momma misses sex."

	"Frank hires hookers -- he doesn't run a string of them.  He gave me
some money to give to you, but I don't think your momma would be thrilled
hearing how you earned it," Crazy Joe related.

	"He did?"  Regina was wide-eyed.

	"Yeah, we were talking about putting it in an account somewhere for
college money or something -- I couldn't figure out how I was going to get it
to you without your momma wondering what was up."  Crazy Joe mused for a
moment.  "What does your momma look like?"

	"Well, like me, but bigger..." Regina related.  "She has bigger
boobs, but the shape is the same..."  Regina had fat cones, as Crazy Joe
remembered well.  "She's a little... thick... but she can do a bikini okay.
She's a little taller than me, but not much -- we run short in my family."

	"Has she ever hooked before?" Crazy Joe asked.

	"I don't think so -- that's why I was asking about Mr. Frank.  I
wouldn't want her working for somebody nasty," Regina explained.

	"Jerome runs hookers -- but they're streetwalkers -- and Jerome has a
low opinion of women in general," Crazy Joe mused.  "I think your momma would
be better off if she didn't get their habits.  I could talk to Jerome about
her, but I have something else in mind..."

	"Like what?" Regina was all ears.

	"Do you think your momma could be interested in, say, young Robert?
I'm sure Maria has told you that we owe him something...  I would prefer that
his education in sex with a woman didn't come from a hooker," Joe related.
"I don't think that's fair to him.  But if your momma took him under her
wing, I could push the money Frank gave me for you at her as payment..."

	"I like it!" Regina gushed.  "I like it a lot!"

	"Maybe we could engineer something where you two girls go over to
your house to study and Momma takes a shine to Robert..." Crazy Joe mused.

	"Ooooo!  Yes!  Yes!"  Regina bounced on the seat.

	"Okay.  We'll take you home after we drop off Maria and Robert.  Do
you want to pitch this, or should I help?"

	Regina thought about it.  "Maybe you should help..."

	"Fine."  Joe turned to Maria and looked a lot less certain of things.
"Honey, we need to talk.  I've been presented with a moral dilemma."

	"What's wrong?"

	"Your folks did well on their first outing -- VERY well.  Your mother
organized things and she worked some... extras... into the deal.  The upshot
is that between what they did and what you and Robert have done, the
remaining debt is small enough for your father to pay out of pocket."

	"That's good!"

	"Well, it is and it isn't, Honey -- because we'll have to tell them
why.  Your mother, in particular, is gonna take it hard -- she was trying to
keep you and Robert out of it and no doubt she thinks she's got things well
in hand.  The truth is gonna be a shock," Joe explained.  "It might tear your
folks apart!  She's already all over your Poppa about this."  He looked out
the car window.  "It's too late for your brother -- but I could release
you..."

	"No you can't!" Maria flared.  "I won't allow it!"

	"Maria..."

	"NO!"

	"It might hold your family together..."

	"And it might not!  Mama is already acting cold toward Poppa -- I
don't think ANYTHING will help -- but if she stops having to..." Maria began.

	"Sweetheart, my people made some changes to your mama," Joe told her.
"She's going to WANT to... well... play around -- even if she and your Poppa
stay together.  We, well, trained her to get the itch..."

	"I heard something about drugs..." Maria mused.

	"We wanted her to embarrass your Poppa by being very cooperative and
enjoying herself in front of him, so we used some experimental stuff.  It
worked better than expected," Joe related.  "Your mama isn't going to be
satisfied with one guy at a time all the time.  It's kind of a long-term
punishment for your Poppa, because one way or another, he'll get his nose
rubbed in it."  Joe wanted to say, 'I'm sorry,' but he couldn't do it --
besides, it wouldn't fix things.

	"This was way at the start..." Maria confirmed.

	"Yes."

	Maria nodded.  "It doesn't change anything.  In fact, it just means
that having you release me is a waste of time."  She waved her finger at
Crazy Joe, "But you have to take care of Mama!"

	Joe nodded.  "I'll find a way.  Let's get you home..."  He hit the
intercom, "Home, Hammer -- theirs."  The car changed directions at the next
intersection; Hammer had been orbiting.  A couple of minutes later, they
arrived at the usual drop-off point.  "Mum's the word on this thing with
Regina's mother," Joe cautioned.  "It will be a lot better for Robert if he
never knows that it was arranged -- and we don't have it locked down, anyway.
Have him stick his head in the window, okay, Sweetheart?  Actually, why don't
you two get out and let me brief Robert in private?"

	"Sure."  Maria leaned up and kissed Joe on the cheek.  "When do you
plan to break the news?"

	"Thursday.  That will give us a couple of days to work on Robert's
problem and things like that before..." Joe explained, adding, "Besides,
that's when they'll expect it."  Maria nodded and got out of the car, waving
for Regina to follow.

	"Robert..."  Maria waved at the back of the car.  Robert nodded and
got in.

	"A couple of things," Joe told Robert, as Robert settled diffidently
into the seat.  "I'm working on the feminine companionship angle.  We don't
want just some hooker for you -- that wouldn't be fair.  Give me a couple of
days."  Robert nodded, clearly not pleased.  "Hang in there," Joe pressed.
"I'm trying to get it right."  He sat back and sighed.  "Second is the matter
of where your parents are.  Since you two helped and they did a pretty good
job on their first outing, they can get out from under this week.  I didn't
foresee this -- or the kind of shit-storm it is likely to produce at your
house.  Your mama has a lot more in the brains and spirit departments than I
anticipated -- and it means that when she finds out why they're off the hook,
it's probably gonna cause your folks to go through a serious rough patch.  I
could lie to them and tell them it isn't over, but I don't like doing that --
even though a couple more outings might settle things down."

	Robert grimaced.  "It might make things worse, too."

	"Yeah, I know.  I can't give you your cherries back -- and you
probably don't want them, anyway -- but I'm not that far along with your
sister.  Problem is, she refuses to back out..."

	"You could make her..."

	"I've considered it, but..."  Joe looked hangdog.  "I can't -- I'm
too fond of her.  I think it's mutual, too -- if I thought she was just
playing the game, I could do it, but..."  He shrugged.  "Why don't you check
on that?  If she's only doing it for the money, I might be able to cut her
loose."

	"Okay, I will," Robert agreed.

	"Be careful about it -- she's as smart as her mother, at the very
least!" Joe warned.

	"Okay."

	"See you tomorrow.  Regina and Maria are talking about going to her
place to study -- I'd like to drop you there, too, just to get a look at
Regina's place.  Frank has taken an interest, you know?  He might want to
send her a care package or something."

	"Sure."  Robert shrugged.  Did he have anything better to do?  No...

	"Let Regina in," Crazy Joe dismissed him.  Robert got out and handed
Regina back into the car.  Hammer, who had been standing by to do that, got
back in and the car pulled away.

	"Joe says you and Regina are planning some study thing at her house,"
Robert opened the conversation with his sister.  "He says he wants me to look
at Regina's place and see if she needs anything, because Mr. Frankowski might
want to send her a gift or something."

	Maria nodded.  "That's okay, right?  I know it might be kinda dull
for you..."

	"I'll do my homework, too..." Robert waved it off, more concerned
with the other thing.  "Joe says that Mama and Poppa can pay off -- but that
there's gonna be trouble when they find out what we did..."

	"Yeah, we talked," Maria groused.  "He wants me to back out of our
deal.  I won't do it!" she insisted.

	"Well, why not?" Robert asked.

	"It won't help -- Mama and Poppa are going to be mad at each other
anyway -- but I gave my word and Joe gave his, you know?"

	"I know, but if he's offering," Robert said carefully.

	"He doesn't want to -- he's just trying to be fair.  But I don't want
him to, either -- I LIKE Joe!"

	Robert frowned.  "What he's doing..."

	"Isn't right?" Maria finished.  "Isn't that for ME to decide?  He's
so gentle -- you have no idea!"  She shook her head.  "You hear about how
terrible it all is -- but look at Regina!  She LOVES older guys!"  She shook
her head.  "Whatever he is to other people, he's very nice to me!"

	Robert knew when to drop it -- Maria was getting worked up.  He let
it go -- besides, he had his answer.

	At home, Maria went right to work on her mother and got provisional
approval right away; the fact that Robert would be along was a plus for
Gina...


	Doris Hicks was more than a little surprised to see the limo pull up
out front of her somewhat shabby home.  Even more surprising was the well-
dressed but dissipated Italian-looking guy who got out of the car behind her
daughter.  Doris wasn't dressed for company -- she had on a halter top,
shorts, and flip-flops due to the heat and her frizzy red hair was tied up
with a scarf to get it off her neck -- the heat STILL hadn't let up and Doris
had no air conditioning anywhere but the bedroom area upstairs in her old
house, provided by a window unit -- which she couldn't really afford to turn
on with no money coming in from Julian.  There was no time to fix things,
either -- they were coming up the walk, fast!

	All she could do was meet them at the door.  "Good afternoon!  Can I
help you?" she asked Crazy Joe pleasantly.

	"Could be," Crazy Joe replied.  "Regina seems to think we ought to
get acquainted."

	"Momma, this is Maria's Uncle Joe," Regina made the introduction.

	"Come in," Doris managed, shaking the proffered hand.  "I'm Doris
Hicks..."  She led Crazy Joe into the living room, which was spotless, if
dumpy.  "Can I get you something to drink?"

	Regina was nodding from behind her, so Crazy Joe said, "Sure.  What
do you have?"

	"Well, iced tea..."

	"Perfect."  Crazy Joe settled into a chair.

	Regina took off for the kitchen ahead of Doris, and was collecting a
glass when her mother arrived and hissed, "What's going on?  Why is he here?"

	"We're in trouble, right?" Regina replied.  "You said the other
day..."

	"Regina, I was just kidding!" Doris lied.

	"No you wasn't," Regina insisted.  "Besides, you haven't done it in a
while and you're cranky -- that's one reason you're thinking about doing it
that way."

	"Regina!"

	"Come on, Momma -- I know THAT much!" Regina retorted.  "I didn't
want you to go out and get in trouble.  Uncle Joe knows people.  Why don't
you talk to him?"

	"What does he know?"

	"Quite a bit..." Regina looked away.  "I had to tell him what was up
to get answers."

	"God..."  Doris covered her face.  "How COULD you?"

	"I don't want some pimp guy hurting you!" Regina snapped.  "I'm
TRYING to help!"

	"Thanks, but..."  Doris shook her head.  She would wade through the
embarrassment and pass the whole thing off...  The ice went into the glasses
and she poured the fresh brew from the pitcher -- Doris made sun tea, largely
because it was inexpensive, but also because it didn't taste like a mix.
"Get the sugar, Honey."  Regina did as she was told, leaving her own glass in
the kitchen, and followed her mother back into the living room.

	Doris handed Crazy Joe a glass.  "It's unsweetened..."

	"Good."  Crazy Joe took a sip.  "Did you talk?"

	Doris turned bright red.  "There's been a mistake -- I made a remark
and..."

	"Sit," Joe directed, in a tone that said he was used to being obeyed.
"Let's clear the air.  I'm not Maria's uncle -- it's just one of those things
you say to simplify things.  I'm a business acquaintance of her father.  I
like Regina -- she's something you don't see every day -- so when she came to
me, I took notice of the fact that she's looking out for her momma."  He
looked over at Regina.  "I'll take it from here, Honey."  Regina nodded and
left the room, going back into the kitchen to get her tea.  "So what did she
tell me that isn't true?  You're divorced, and you don't have a job, and the
old man has chopped off alimony and child support -- right?"

	"Yes, but..." Doris began.

	Crazy Joe rode right over her.  "You wouldn't have made the remark
unless you were thinking about it -- but I don't think you're falling back on
something you've done before -- am I right?"

	"Uh, no..."

	"Personally, I don't think streetwalking is a good way to get sex,"
Crazy Joe continued.  "Even if you were seriously looking at getting into the
business, I think you should start out at a different level.  I know a guy
who knows a guy -- but I don't think you want him to run you -- he's been
burned and he doesn't like or trust women."

	"But I didn't..." Doris began.  Crazy Joe just looked at her.  She
took a breath.  "Okay, I did.  But you're right, I was hoping to avoid the
whole streetwalker thing and just, you know, bring in a little money to make
things easier."  Somehow, lying about it seemed like a waste of time -- the
man seemed to know better, anyway, so why bother?  There was something about
him -- an attitude.  He'd seen it all -- she couldn't surprise him.

	Crazy Joe wrinkled his nose.  "The commercial part of the transaction
is something you have to get used to -- and some women really don't, and it
screws up the sex part.  That said, I have a proposal for you -- piece work
-- a one-shot deal.  Would you object to introducing a young guy -- say, a
fifteen-year-old -- to sex?"

	Doris blinked.  "Fifteen?"

	"Yeah.  Look, this is a favor I owe -- you would be helping me out.
The kid had his cherries popped -- by a gay guy.  Now, it went really well,
but the boy isn't sure he isn't gay -- and isn't sure he wants to be -- so he
needs to try the other flavor, you know?  And it needs to be done right --
not by a hooker.  It needs to be done by someone who can take him all the way
and give him the whole experience -- and make him feel good about it."

	"So it wouldn't just be a quick fuck..."

	"No.  I would rather the boy never realized that it was arranged at
all -- I would want him to think you took a shine to him and decided to show
him the ropes.  Now, if you were to do this, well, we wouldn't talk about it,
but I would owe you a favor.  In the meantime, there was a little gift I
wanted to give Regina for helping Maria through a serious personal issue --
something that she would have some difficulty explaining to you, so it's best
that I do it in person."  Joe reached in his pocket and peeled five hundreds
off his roll.  "Maria had to work her way through an important decision here
recently, and Regina provided help and advice and I wanted to show my
appreciation."  Crazy Joe eyed Doris significantly and said, "This is totally
different from the other thing, but I'm sure you will see to it that the
money goes to help you both be more comfortable."

	"Um, yes..."  Doris realized that Crazy Joe was deliberately muddying
the waters.  Was this really for Regina -- or was it a bribe to have sex with
a boy?  Almost certainly it was the latter...  She was holding the money
before she could think to object.

	"I wouldn't want you to think I'm rude, or anything, but since I want
this done right -- you're good at it, right?" Crazy Joe asked.

	"What?"  Doris blinked.

	"Sex.  The basics, anyway.  I mean, no offense, but if I hooked him
up with a dead lay, he might end up gay for no good reason..."  Crazy Joe
eyed her.

	"No, I do all right," Doris muttered, embarrassed.

	"I'm sure you do," Joe agreed, thinking, 'Your daughter sure does...'

	"I can see how important it is..." Doris muttered, thinking, 'Is he
asking me to fuck him?  Yeah, he probably is.  He's very smooth about it,
though.  Besides...'  She fingered the bills in her hand, 'there's this --
and I could use a little...'  "Maybe..."  She shot a glance at the kitchen,
"Maybe I should... demonstrate, or something..."

	Crazy Joe followed Doris' glance.  "Since Regina brought us together
more or less specifically for the purpose, you probably won't have to expend
a lot of effort hiding it from her..."

	"Very true..."  Doris squared her shoulders.  "What would you like?"

	"Oh, visuals, I guess.  Some oral.  Straight sex.  Do you do anal?"

	"I have," Doris admitted.

	"He's been done, but I don't think he's returned the favor.  You
needn't try to get it all in with him in one pass, though."

	"I can do this," Doris thought.  "All right.  Now?"

	"Just a moment."  Crazy Joe went to the front door and opened it,
"Hammer!"  He beckoned his driver from the car.  Doris stood there,
thunderstruck!


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