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From: Thinking Horndog <im_a_thinker@yahoo.com>
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Subject: {ASSM} The Gambling Debt 5/21 {Thinking Horndog} (MF M+F MM M+M Mm Mf oral anal ir 1st noncon reluc blackmail cuck)
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Date: Tue, 10 Apr 2012 21:10:08 -0400
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Chapter 5
<1st attachment, "Gambling_Debt_5.txt" begin>

Author: T. H. Barker (Thinking Horndog)
Title: The Gambling Debt
Part: 5 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 5

	Crazy Joe sat at his desk, staring at his blotter.  "I bit off more
than I can chew with this one," he announced.

	"Boss?" Martin looked up.

	"The Tomaselli kid."

	"Yeah?"

	"Yeah.  She's absolutely fucking perfect.  You know what she said
today?  She said, 'I have a girlfriend who likes men -- would any of your
poker buddies like to meet her?'  I nearly fucking fell out of the car!"

	"Well, the mother is a fine piece..." Martin noted.  "Besides, does
she understand that 'liking men' isn't just being bounced on your knee?"

	"She says the girl has been fucking some guy since she was ten,"
Crazy Joe replied.  "Don't kid yourself -- she hasn't done it, but she knows
what she's there for -- and she's perfectly willing to do it."

	"It's all about her folks," Martin opined.

	"She knows they're fucked," Crazy Joe replied.  "You weren't there
when we sat there horse-trading in the back of the car.  The little slip TOLD
ME what you did to her mama and poppa, not the other way around!  Her and her
brother know every fucking thing -- apparently they were eavesdropping on
their parents while they had a fight or something."

	"No shit?"

	"No shit."

	"What's up with the boy?"

	"He's... willing.  He thinks he's capable of going both ways -- and
if it'll help, he'll kneel up with his ass in the air like a good little
twink," Crazy Joe related.

	"Would it help?"

	"Well, it would be a paying proposition," Crazy Joe replied.  "I'm
giving Tomaselli a credit for the girl -- and I'm pretty sure I'm gonna get
my money's worth and then some.  But I can sell the boy's cherries, just like
I planned -- he'll just be cooperative."

	"So get top dollar," Scott rumbled.  "Why don't you wave the kid
under Jerome's nose?  He'll be plenty broke in when Jerome is done with him,
but Jerome would probably get a kick out of having some young stuff that
didn't scream and shit when he fed him that sausage of his."

	"Good idea."  Crazy Joe picked up the phone.


	Jerome Willis was a pimp.  He ran about a dozen girls out on the east
side of town -- a definite low-rent district.  But he didn't trust a woman
any farther than he could throw one -- and if one populated his bed, it was
as likely to be for punishment as anything else.  Jerome was black and
considerably well-hung and he had a talent for being just brutal enough to
keep the full attention of his whores without taking them out of service.  It
was an article of faith with Jerome that if it didn't have a dick, it was
feckless and unpredictable.  Jerome liked man-pussy -- preferably boy-pussy
-- but that shit was hard to come by, and most of it wasn't willing to kneel
up and take his ten-incher.  Jerome was also a regular at Crazy Joe's poker
table.

	"Hey, Jerome, you comin' to poker?" Crazy Joe asked.

	"You gonna have some little piece squirming on your lap?" Jerome
laughed.

	"Got a new one -- a regular princess," Crazy Joe laughed back.
"Never been kissed -- but willing."

	"Lucky fuck..."

	"It's why I called, actually," Crazy Joe noted.  "I got a line on
something you might be interested in."

	"Oh?"

	"Your type.  Mid-teens.  Italian kid, kinda hot, twink build.  He's
got all his cherries, but he's... bi-curious, I guess it's called."

	"No shit?"

	"No shit.  You can play with his ass at poker, and if you like it, we
can talk price."

	"What are you thinkin'?"  Jerome didn't want to telegraph it, but he
was drooling.

	"We can go on performance.  If he kneels up pretty and smiles while
you ream him with that blood sausage of yours, maybe two grand.  If he gets
stupid, we'll knock off some.  That fair?"

	"If he's good, I might want to do him again," Jerome noted.

	"Standard rates after his cherry is popped -- that fair?"

	"Sweet!"

	"See ya Friday.  Bring your own lube."  Crazy Joe hung up.

	"What about the other slip?" Martin asked as Crazy Joe sat back.

	"Well, she's a questionable, at this point," Crazy Joe mused.  "See
if Frankowski is interested."

	Martin nodded and got on the phone.


	'Frankfurter' Frankowski was an 'insurance man' -- meaning he ran the
'protection' racket in town.  He was reasonably honest about it, though; the
rates weren't excessive and you didn't fuck with one of his customers -- he
made examples of thieves and arsonists and such that he caught, and his
informant network got him to a thief before the police nine times out of ten.
The cops generally just had to find out who was in the hospital after a
robbery to catch their man.  Convenience store holdups were WAY down in town
as a result...  As for the 'frankfurter' it wasn't a kielbasa or anything --
just a normal-sized cock -- but Frankowski spent a lot of time scratching it.

	"Ladies Night at poker," Martin informed him.

	"Shit.  Joe's got a new squeeze?" Frankowski grunted.

	"Yeah.  Fresh.  VERY fresh."

	"So he'll be rubbing her panties under her dress, getting people all
hot, but not really doing shit."  Frankowski was well aware of the fact that
Joe liked to take his time breaking in a new 'girlfriend.'  It would likely
be several weeks before the little slip sat naked on Joe's lap, if she had
any sense -- or it could happen Friday, if she didn't.  Frankowski had seen
it go both ways -- and sampled pieces that pissed Joe off.

	"Yeah, well, Joe asked me to call you because he's got a line on
something the same age but well broken in," Martin replied.  "Something you
could use the frankfurter on -- and who would thank you for it, if you
weren't too rough."

	Frankowski frowned at the phone.  "No fuckin' shit?"  Frankowski
generally got little girls when momma and daddy refused to pay their
insurance payments -- a generally unpleasant situation for the little girl
and her parents.  Frankowski was omnivorous -- he fucked women of all ages,
and the occasional male -- the latter group as punishment, usually, rather
than for fun.

	"That's what is advertized," Martin replied.  "There are details to
work out -- we're not going to set up anything unless you're interested, but
she's looking for something to play with.  Joe figured the frankfurter might
be itchy."

	"Kind of him.  Yeah, shit, if he can arrange it, I might like to have
somebody hold my cards for me," Frankowski allowed.  "What's the rate?"

	"Still to be determined, but cheap, probably," Martin replied.

	"Cool.  I won't want to just rub her twat under her dress, though."

	"I don't think she'll want you to stop there, either," Martin
chuckled.

	"I'm in."

	"See you there."


	When Martin related Frankowski's interest to Crazy Joe, he responded
with, "Send Maria a text.  Ask her to call me."  Ten minutes later, Maria
heard a buzz coming from her clutch purse and opened it to see the text on
the cell phone Crazy Joe had given her.  Since she was in English class, she
had to wait almost a half-hour, but she was on the phone as soon as the lunch
bell rang.  "Joe?"

	"Hi, Baby.  Couple of things.  That girlfriend of yours?  I might
have found somebody who wants to party with her -- but I don't want any
surprises, you know?  Can you bring her around when I come for you tonight?"

	"I'll see what I can do, Joe," she promised.

	"Okay, Baby.  We'll just talk.  I need to hear that she understands
what is going on, you know?  No surprises."

	"Uh huh.  I understand."

	"Tell your brother I need to talk to him, too."

	"Okay.  Anything else, Sweetie?"

	Crazy Joe grinned into the phone.  "No, that's it, Baby.  I'll see
you after school."

	"Okay.  Bye!"  Maria hung up.

	Martin eyed Crazy Joe.  "What did she do?"

	"Called me 'Sweetie.'  Don't let THAT out in public!" Crazy Joe
laughed.

	Martin laughed.  "She's something, all right."

	"At the rate she's going, she'll inherit the fucking business!" Joe
laughed.


	Maria let nothing get in the way of finding Regina.  "We need to
talk."

	"Okay..."  Regina looked cautious.

	"Can you meet me in the parking lot after school?  My man friend
wants to meet you."

	"Yeah?  Why?"

	"He says he might know somebody.  But he wants to be sure you
understand what's what," Maria explained.

	"Oh.  Yeah, okay."  Regina let it soak in for a minute and added,
"Cool!"

	"Okay, a couple of things," Maria admonished.  "This is a favor, you
know?  You asked.  You know my man friend isn't known for being super nice,
so you can figure that his friends aren't, either -- but if he says the guy
will be cool, I believe him."

	"Okay."  Regina nodded.

	"Second -- he's mine, you know?  Don't get ideas.  I need to not get
messed over, here, because my family needs me," Maria pointed out.

	"Okay, no problem."  Regina nodded.

	"Okay, I'll see you after school."


	Maria waited until after school to talk to her brother.  "Robert, Joe
wants to talk to you, but there is something else going on, first.  Okay?"

	Robert frowned.  "Okay.  Sissy, you're asking for it, here.  You're
not letting me help you.  Things could happen."

	Maria sighed.  "We already know what's going to happen.  Right now, I
have some control over it, but in the end..."  She shrugged.  "Don't worry,
okay?"

	"I can't really stop," Robert mumbled.

	"You can't fix it, either -- so worrying doesn't help," Maria pointed
out.

	"Yeah, okay."

	"Just get in the front with Hammer.  When Joe and I are done, he'll
call you back," Maria directed.

	"Okay."


	When the limo pulled up, Maria leaned into the car and told Joe,
"Robert doesn't know about the other thing."

	"Okay."  Joe pushed the button to raise the privacy barrier between
the passenger area and the driver's compartment as Robert got into the car
beside Hammer Thornton.

	"I'll be right back."  Maria went off to find Regina -- who, as it
turned out, wasn't that far away.

	"Nice car!" Regina murmured as she followed Maria into the passenger
area.

	Crazy Joe sat there examining a pudgy little freckled redhead with
jiggly cone-shaped titties and some baby fat.  Regina looked back, rubbing
her nose, while Hammer pulled the car out into traffic.  After a few moments
of pregnant silence, Crazy Joe said, "Maria tells me you've been telling her
some interesting stories."

	"We talked about men," Regina agreed cautiously.

	"Men my age?"

	"Some a little younger."

	"What do you do with men, Honey?"

	"Fun things."

	"Just talking to you about this is kind of dangerous," Crazy Joe
noted.  "Maria says you asked her to hook you up.  I need to know that you
are for real and that you aren't working for the cops or something."

	"I understand."

	Crazy Joe frowned.  "The more I think about this, the less I like it.
You could be wearing a wire..."

	"I'm not."

	"Prove it."

	Regina threw her top over her head and stood, bracing herself on
Crazy Joe's knee while she undid her skirt.  When it fluttered to the
floorboards, she asked, "Okay?"

	Crazy Joe pursed his lips.  "I should probably check the bra."  The
thin cotton panties displayed everything, including a camel-toe that was just
beginning to sprout thin hair.  Regina just leaned up and let Crazy Joe feel
her chubby breasts.  When he was done, he waved at the seat, "Toss me that
stuff."  He went over the blouse and skirt meticulously while Regina sat
there in her underclothes, apparently unperturbed.  "Okay," he said finally,
handing her back her things and waving for her to dress.  "You seem to be on
the up-and-up.  It's unusual for a girl your age to ask..."

	"Yeah, I know.  Everything has to be kept super-secret," Regina
agreed.  "I'm used to it."

	"So give me a little history," Crazy Joe invited.

	"My stepdad started playing with me when I was ten," Regina related.
"It wasn't much right away, just a little extra stuff while we were playing
-- touching my legs up high and stuff.  His thing -- can I say dick?"

	"Sure."  Crazy Joe's eyelids drooped.

	"His dick would get hard.  I would tease him by rubbing back and
forth on it while I sat in his lap.  Momma never seemed to notice.  It got so
I was liking it, too, and I went from that to rubbing myself.  One day, Daddy
offered to rub me through my panties, and I said yes.  It was WAY too good
not to do all the time, so I started rubbing him, and a little after that, I
decided my panties were in the way and his underwear was, too.  Real soon
after that, he showed me how nice licking was, and I learned to suck him.  We
were good like that for, oh, a couple of months, I guess, but he wanted more,
so he started playing with my butt."  Regina sat staring at nothing for a
bit, then brought herself back.  "When we went at it slow, everything was
good -- and I went from fingers to sitting on his dick -- but he would get
all anxious sometimes and rush things -- and that hurt!  One day, he got too
wild and I yelled -- and, well, he got caught."  Regina looked a little
diffident.  "I don't want to say who by, okay?"

	Crazy Joe shrugged.  "Okay."

	"There was some trouble -- the guy who caught him was all upset and
made him divorce Momma and leave -- without telling her why.  I felt bad
about that -- Momma was real upset.  But then it turned out that Stepdad had
another, older girlfriend, and I didn't feel so bad."  She sat staring at
nothing again for a while, then resumed.  "Things were kind of sucky for a
while -- but the guy who caught Stepdad that day was worried about what we'd
done and how and how I felt about it and did it hurt and we had long
talks..."  Regina grinned impishly, "and I seduced him.  That's the word,
right?  When you talk somebody into sex?  He would ask a question and instead
of just telling him the answer, I would show him.  I showed him how Stepdad
rubbed my pussy and how I rubbed his dick...  It took a couple of weeks, but
he slowly got the idea that he wasn't hurting anything and that I wanted it
-- and then we REALLY got going!  I think he was a little upset when he found
out that the only problem I had that day was that Stepdad was in a big hurry
and my butt wasn't wet, so it hurt..."  She shook her head smiling.  "He's
NEVER in a hurry!  I have to kind of push him along, sometimes.  I remember
the day he opened up my pussy -- he must have taken four hours getting me
ready!  I was afraid Momma would come home from shopping and catch us!"

	Crazy Joe pursed his lips.  "So you do it all, then."

	"Yes."  Regina nodded.  "After a while, the excitement was over and
my man friend had to go back to where he lives -- and he only gets to see me
maybe once a month, and sometimes we just can't get any alone time..."

	Crazy Joe chuckled.  "So you have an itchy pussy."

	"Uh huh."  Regina nodded.

	"That's quite a tale," Crazy Joe mused.  "If it's true -- and you'd
have to be a pretty good liar, I admit, to put that over -- you don't have a
cherry..."

	Regina raised one leg and pulled aside the crotch of her panties.
"Feel.  I'm wet -- it'll be okay."  Crazy Joe sat up and rubbed Regina's
split with his middle finger and then sank it inside.  "Oooo!  Big fingers!"
Regina grinned and winked at Maria.  "You'll like that."  She turned a
coquettish look on Crazy Joe, "Want to feel my butt hole too?"

	"No, I'm convinced."  Crazy Joe extracted the finger, but Regina
grabbed the hand and sucked her juices off the finger before releasing it.
"You're quite a tease.  Will you mind if my friend wants to have his fun
right there at the table?"

	"No, not really," Regina replied, totally blas�.  "You won't be doing
much with Maria Friday night, will you?"

	"No, probably not," Crazy Joe agreed.  "I'll be taking my time."

	"That's fine.  I promised Maria I wouldn't do you -- that's okay,
right?  She's possessive."

	Crazy Joe turned to Maria and grinned from ear to ear.  "No, that's
fine.  If I didn't have Maria, I'd be interested, but I try to keep it to one
girlfriend at a time."  He glanced out the car window.  "Where should we take
you?"

	"Back to school is fine."

	Crazy Joe tapped on the partition.  "Back to school, Hammer."  He
returned his attention to Regina, "Okay.  Can you get out Friday night?
Things will be complicated, since Maria's folks won't be home and probably
shouldn't hear about things..."

	"Well, it SHOULD be a sleepover..."

	"Her parents can't know, because she'll be with me -- and they're,
well, unaware.  Tell you what -- I'll have a girl in my office carry my cell
and if your momma wants to talk to Maria's, she'll pretend that's who she
is," Crazy Joe proposed.

	"Okay."

	"Maria's folks will probably be picked up around six-thirty, and I'll
be swinging by the house at probably seven-thirty.  How will we get you?"

	"Ummm, can you just pick me up after school and keep me?" Regina
asked.

	"Yeah, okay.  That works," Joe nodded.  "I'll have Hammer take you up
to the house before he picks up Maria and Robert."  He eyed her.  "Wear a
skirt.  Wear something that can be changed to be sexy, I guess -- but not
something your momma won't let you out the door in.  I guess you can't get
into trouble in school clothes, right?"

	"Right," Regina nodded.

	"You can always pack something else in your overnight bag -- but
don't put anything in there your Momma will find and freak on you at the last
minute.  I'm gonna give my friend a glowing report on you -- and I don't want
egg on my face," Crazy Joe warned.

	"Okay."

	The car pulled up to the curb on the next block from the school and
Crazy Joe waved Regina out.  "See you Friday."

	"I can't wait!"  Regina giggled and gave Maria a hug as she got out.

	"Sit up front with Hammer for a bit, Sugar," Crazy Joe told Maria.
"I need to talk to your brother -- man talk."

	"Okay, Sweetie," Maria agreed.  "Did I do good?"

	"Sure looks like it.  If she isn't the real deal, she's the damnedest
midget policeman I ever saw!" Crazy Joe chuckled.

	Maria got out and tapped on Robert's window.  "We're switching."

	Robert nodded and got out of the car, holding the door for his sister
and closing it behind her.  Then he got into the seat facing Crazy Joe.

	Crazy Joe sat back and pursed his lips.  "Got a gig for you.  It's
good news and bad news.  If you handle it and show a good attitude, you can
probably write your own ticket -- serious bucks against your old man's bill.
That's the good news.  The bad news is that it'll be a fucking challenge --
the guy is black and hung like a porn star.  It'll also be at the poker
party, so he might start feeling you up in front of your sister.  Now I know
that's serious embarrassment and all that, so I'll have a word with him, but
he like his boys, and he could even get a little romantic as the night goes
on.  In any case, you'll be there as a boy toy, and there is no hiding that."

	Robert sat staring out the window.  "What else?"

	"Once I turn him loose on you, you're gonna get fucked.  You can do
your best to make him happy and have a ball, or you can get stupid.  Either
way, he's gonna do you -- but you come out a lot better if you don't piss him
off -- and if you REALLY trip his trigger, well..."

	Robert stared out the window some more, then murmured, "I'm worried."

	Crazy Joe frowned.  "What about?"

	"If I do this -- maybe more than once -- what does it do to me?  Will
I stop liking girls?"  Robert's eyes were troubled.

	Crazy Joe pursed his lips.  Technically, he shouldn't give a shit
what happened to the boy -- and he wasn't much of a father figure.  But this
could affect his relationship with Maria, which was looking like something
unique...  "If it turns out you only like boys, it won't make any difference.
I guess if you were to spend a lot of time fucking boys before you get any
pussy, it might skew your outlook.  Tell you what -- I'll rustle up a piece
of ass for you to make comparisons with sometime in the next few days-- how's
that?"

	"Yeah, that might work..."  Robert nodded.

	"You need to not let it eat you, boy.  Kids your age play with each
other's dicks all the time and grow up to father fourteen children on three
different women.  It's an experiment.  Check it out -- see if it's good.
I'll get you a pussy to try out for comparison.  Maybe you'll like one or the
other -- or maybe you'll like both.  Deal?"

	Robert gathered himself.  "Deal."

	"Awright, send Maria back -- and tell Hammer it's time to go home."
Crazy Joe waved him out of the passenger area.  After the swap, Maria pressed
herself to Crazy Joe's side all the way home.

	That put the younger generation on the same long slide as their
parents -- into Friday.  Regina pitched the overnighter to her mother --
successfully -- Wednesday evening, and reported it to Maria on Thursday.
Maria forwarded the information to Joe Thursday afternoon.  Martin called the
house and asked Tony if he had money -- and he said no, of course -- so he
asked to speak to Gina.  "Hey, Hot Stuff!"

	"Hello."  Gina was a good deal less enthusiastic.

	"What's the old man know about the plan for tomorrow?" Martin asked.

	"Nothing.  We've been avoiding the subject," Gina replied.

	"Good.  One of us will be by around six -- and we'll keep him busy
until we're all in the car on the way, then we'll lower the boom."

	"Okay," Gina agreed.

	"See you then.  Make sure you're all squeaky everywhere -- we'll do
up the old man at six."  Martin hung up.

	"What was that?" Tony asked.

	Gina sighed.  "He wanted to have a little fun.  Anyway, they'll be by
at six."

	"Okay."  Tony left it at that -- which was the way Gina wanted it.

<1st attachment end>


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