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Subject: {ASSM} The Gambling Debt 17/21 {Thinking Horndog} (MF M+F MM M+M Mm Mf oral anal ir 1st noncon reluc blackmail cuck)
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Chapter 17 of 21
<1st attachment, "Gambling_Debt_17.txt" begin>

Author: T. H. Barker (Thinking Horndog)
Title: The Gambling Debt
Part: 17 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 17

        Doris and Jerome were barely out of sight of the game room before
Jerome pressed her against the wall and loomed over her.  "I hear you gave
Bobby his first taste of pussy..."

        "Uh huh!"  Doris looked up at him and nodded, frightened.  Jerome was
a good foot taller than she was and his expression wasn't all that peasant.

        "Did you do a good fucking job?" Jerome demanded.

        "I did my best," Doris gibbered.

        "You didn't just get yours, did ya?"

        "Oh, no!  I made sure he had a good time!  I taught him things!"
Doris insisted.

        "What did you do for him?"

        "I sucked him -- that didn't take long."  Doris smiled in spite of
herself.

        "How was it?"  Jerome looked pained.

        "What?"

        "How did it taste?"

        "Sweet.  It was good," Doris replied, getting a handle on Jerome's
interest.

        "I missed that..." Jerome grunted, looking away.  "There was a bunch
of shit I shoulda done..."  He looked back at Doris.  "What else?  Did you
give him any booty?"

        "No," Doris replied.  "After one load in my mouth and two in my
pussy, he was done."

        "Your twat any good?" Jerome asked.  "You know he wants us to be
friends or something.  I get a piece of pussy every once in a while.  Pussy
is okay -- it's the other end that gets bitches in trouble."

        "The other end?"

        "Their mouths.  You aren't bitchy, are you?  I can't abide that --
I'll slap the shit out of you right in front of Bobby.  He needs to know how
to handle bitches," Jerome declared.

        "No, I'm not bitchy," Doris declared.

        "You don't impress me as bein' the brightest bulb in the circuit,"
Jerome grunted.  "Do you do as you're told?"

        "Well..."

        "Wrong answer."  Jerome grabbed her by the side of the neck and
locked his eyes with hers, his forehead pressed against hers.  "Bobby wants
something from you, you fucking up it -- understand?  Your mouth, that skank
pussy of yours, your asshole -- I don't care!  And if I take it into my head
to make Bobby feel better by poking one of your holes, I don't want to hear
nothing but gratitude, get me?"

        "Uh huh!"  Doris was about to pee her panties!

        "I know Crazy Joe has some enema gear lying around here -- you find
it and you clean out your ass, just in case Bobby decides he wants to kneel
us up side-by-side and see if there is any difference between a man-hole and
a woman-hole -- understand?"

        "Yessir!"

        "Least you got respect," Jerome muttered grudgingly.  He grabbed her
left tit roughly, "These real?"

        "Yessir!"

        "Good.  I don't want Bobby having to fuck with water bags.  You ever
fuck black dick?"

        "No sir!"

        "Want to?"

        "Yessir!"

        "You're pretty good with answers, anyway."  He grabbed Doris by the
upper arm and led her to a bathroom.  "You do what I told you -- I'll make
excuses for your ass."  He turned away and headed up the hall.

        Doris watched him go, her knees knocking.  Jerome could have fucked
her at just about any point in the conversation; he'd scared the shit out of
her -- but she was wet.  She found herself hoping that Robert DID plan a
threesome...

        There were bottled enemas in the linen closet in the bathroom.  Doris
used two...


        Jerome and Doris weren't out of sight before Regina presented herself
before Frankowski.  "Mr. Frank, how come you're fooling around with Momma?"

        "We're just messing with her head, Honey," Crazy Joe came to the
rescue.  "We're softening her up."

        "That's right, Honey," Frankowski agreed.

        Regina poked Frankowski in the chest.  "If you want to do things with
Momma, it's okay -- but I come FIRST!"

        "Yes, you do!" Frankowski agreed wholeheartedly, "Yes, you do!"

        "Okay, then."  Mollified, Regina headed back to the game console.

        A couple of minutes later, Jerome returned.  "Sorry about the delay.
Doris is gonna be awhile -- she had some cleaning up to do.  You're gonna
have to hang out for a while, Frank."

        "That's fine."  Frankowski decided to curry little Regina's favor by
watching her play video games.

        Crazy Joe waited until after Gina's break to ask Jerome, "What REALLY
happened?"

        "I told her to wash out her skank ass in case Bobby wanted a piece,"
Jerome related.  Crazy Joe snorted laughter.  "She's about as dumb as a box
of rocks, but she seems to have some respect."

        "I put her on Robert," Joe related, "It wasn't an accident.  I really
don't want him to ever know that, though."

        "No, you're right -- I want to win fair and square," Jerome grunted.
"My shot..."  He made to head off.

        Joe stopped him.  "Hey, do me a favor," he asked, "Fuck with these
two a little.  I know you probably won't dick either of them tonight, but I
enjoy watching them deal with it."

        "Gina's pretty cool," Jerome murmured.  "She'll be hard to shake.
Tony -- he's fuckin' scared of me."

        "Yeah," Crazy Joe agreed.  "Whatever."  Jerome nodded and went off to
shoot.


        Crazy Joe and Tony won, but it was a close call; when the game was
over, Gina announced that she, too, needed to go to the bathroom.  Gina
merely got directions, however, and when she got there, the bathroom door was
closed.  "Hello?" she inquired, rapping on the door.

        "Yes?"  It was Doris' voice.

        "Are you okay?"

        "Yeah, but I'm busy.  I'm not using the toilet, though -- not yet."

        Gina opened the door to find Doris knelt over the bathtub with a
bottled disposable enema in her hand.  "What's this?"

        "That Jerome guy said do it."

        "Yeah, so?  Why?"

        "In case Robert wants my..."  Doris skidded to a stop.  "Uh, about
Robert...  I'm not a predator or anything.  Crazy Joe put me up to it.
Robert was kind of screwed up after Jerome, I guess, worried that he was gay.
So Crazy Joe..."

        "Asked you to do him a favor?" Gina finished, dropping her thong and
settling onto the toilet.

        "Uh huh."

        "How do you know Crazy Joe?"

        "I didn't.  Regina, um, introduced us.  I'm not real sure how she
knows him..."

        "Through Maria, I think," Gina supplied.  "Want some help?"

        "Please?"

        "You don't seem to be real well -informed about what's going on,
here," Gina mused as she inserted the tip into Doris' rectum and began
squeezing the thin plastic bottle.

        "THAT'S for sure!"

        "Why are you doing this -- because Jerome said to?  Or does Crazy Joe
have a hammerlock on you?" Gina asked.

        "Jerome.  He's scary!" Doris insisted.

        "He's a pimp, you know."

        "Maybe that's it..." Doris mused.

        "What do you think is going to happen tonight?" Gina queried.

        "I think I'm gonna get fucked," Doris replied.  "By who, though --
that isn't clear."

        "How do you feel about that?"

        The look Doris gave Gina said, 'Can I be honest, here?'  Gina said,
"Go ahead, I won't tell -- and I won't judge."

        "I don't think I'm a slut or anything, but I'm looking forward to it.
This is an adventure for me, sort of.  The whole thing kind of fell on me out
of the blue.  I don't think Crazy Joe would let me go home, anyway -- there
is something going on here that he wants me to find out, I think."

        "Probably," Gina nodded.  "Everybody here has their dirty little
secrets.  Joe is enjoying the idea of having them come to light.  He's
goading that Frank guy and Jerome to mess with us, too, for the fun of
watching us react."

        "You said something about hammerlocks..."

        "I can't tell you why, but Joe has a grip on me and my husband.  He's
a bookie -- did you know that?  He'll probably tell you himself at some point
why and how far it goes, just to embarrass us, but the short version is that
Tony was out of work and broke and made some bad bets..."

        "Oh.  That's interesting..."  Doris grunted as a cramp hit.  "I'm
going to need the toilet..."

        "No problem -- I'm done."  Gina wiped and flushed and got up.  Doris
shifted back to the toilet. And Gina sat on the edge of the tub.  "About
Robert..."

        "I did my best to make it good for him and teach him a few things
about women, you know?  I'm not a hooker.  I said something about being horny
and needing money in front of Regina and suddenly Joe showed up -- but it was
more of a favor..." Doris sputtered defensively.

        "I didn't know Joe cared," Gina mused.  "He's kind of surprising,
actually, but I'm on the wrong side of things.  Thanks, I guess."

        "Okay."  'Whew!'

        "Look, I think things are going to get wilder and wilder, so expect
it," Gina mused.  "That bunch could spread us both on the pool tables -- and
they might.  You seem to be okay with the sex part, so I'd suggest just
rolling with the punches."

        "Okay."  Doris started voiding -- and the sounds and the smells were
less than appetizing.  "Sorry!"

        "No problem -- I'm going back."  Gina got up.

        "Do you need to do this?" Doris asked.

        "I did it at home, beforehand," Gina replied, and let herself out of
the bathroom.


        Since there was a break, the men filtered off to the bathrooms.
Jerome headed back to one near the servants' quarters.  It was a larger, more
public item with a couple of urinals.  Hammer came in while Jerome was
pissing.  "How's it going?"

        "Oh, fine."  Jerome shook his head.  "Bitches."

        "What about 'em?"

        "They piss me off.  Bobby hooked up with this redhead and I probably
have to be half-assed nice to her.  I gave her some crap in private, but you
know how they are."

        "That's the older one, right?  Not the kid?" Hammer asked.

        "Yeah."

        "Just shove your tool in her," Hammer advised.  "She likes being
handled.  I think she's into kink -- one of those BDSM bitches that likes to
get whipped and shit.  I know for a fact that if you grab her by the neck and
shove your tool down her throat, she gets all gushy on you.  Problem is, I
can't deal with that shit, long-term.  I know you don't like bitches in the
first place, so she's got two strikes against her going in, but if you just
want one that behaves herself, you might want to look at that one twice."

        "No shit?" Jerome blinked.

        "Boss wanted her to fuck Robert -- and he wanted to know if she was a
good fuck.  So I did her -- and I wasn't particularly romantic about it.  She
loved that shit.  Boss rolled right over her, so I did, too -- and she told
her kid she wanted to see me again.  Hell, I made her ride up front with me
tonight and shoved my tool down her neck while I was driving.  She just
sucked it up.  Just tell her you know she's a fucking slut and to quit
farting around, and she'll bend the neck and do whatever..."

        "I could use a half-dozen of those!" Jerome laughed.

        "Yeah.  Submissive, I think they call 'em," Hammer mused.  "She
brings out the worst in me -- I'm gonna have to stay away."

        "Huh."  Jerome went to the sink and washed his hands.  "Come to think
of it, she was real respectful."

        "There you go..."


        With the return of Gina and then Doris, Crazy Joe switched up the
teams.  He put Frankowski and Gina together, took Doris, and partnered Tony
and Jerome.  Frankowski made a couple of opportunities to pat Gina's ass --
usually winking at Regina in the process -- and Jerome played with Tony's at
least once, nearly causing Tony to drop his cue.  Frankowski and Gina won the
first game, and played each other while Crazy Joe and Doris lost to Tony and
Jerome.  Jerome had a couple of short conversations with Doris, who continued
to be respectful; Robert, who was watching both of them closely, wandered
over to ask Jerome about it.

        Jerome cocked his head.  "Bobby, what did you hope for, bringing us
together?"

        Robert shrugged.  "I honestly, don't know."

        "You know me and women don't get along."

        "Yeah."

        "Doris and I seem to be doin' okay, though.  I just wanted to make
sure she did everything she ought to have done, you know?  I didn't want you
missin' out on nothin'."

        "That's nice."

        "I want to win fair and square," Jerome insisted.

        "Um," Robert grimaced, "What if this isn't something you can win?  I
mean anybody, not just you."

        "You mean any guy?" Jerome asked.

        "No, I mean ANYBODY," Robert clarified, "Guy or girl.  I don't think
guys are going to win or girls are going to win -- maybe one particular guy
may, or one particular girl -- or maybe one of each..."

        Jerome frowned heavily.  "I don't get it.  Want to run that by again?
I'm thick..."

        "Um, yeah, let's start over," Robert murmured.  "Okay, look -- you
can win, but if you do, it's a win for you, not a win for the boys' team.
And if you were to lose, it probably wouldn't be because you were a guy, but
something else, like your age, maybe.  Doris isn't really competing, I don't
think, because she's closer to your age than mine and doesn't think it'll
work -- but if she DID compete, she would win or lose for herself, not
because she's a girl -- got it?"

        Jerome frowned.  "Yeah, I think so.  You think you can go either way
-- or maybe both -- depending on the person."  He looked pained.  "Am I too
old?"

        "That isn't clear, Jerome," Robert said gently.  "Maybe not.  Maybe
not for now, but it could come up later.  For now, well, let's just do things
for now."

        "Okay, Honey."  Jerome pulled the slight teen to him, holding him
backed against him.  Robert didn't fight it -- and it only lasted until
Jerome's next shot, anyway.


        The games over, Crazy Joe announced, "Dinner time!" and led them to
the dining room.  Crazy Joe organized seating, with Maria on his right,
followed counterclockwise by Frank and Regina, Doris at the foot of the
table, and Robert, Jerome, Tony and Gina coming up the left side.  Once
everyone was seated, Crazy Joe said, "For dinner conversation, I'm going to
ask each of you in rotation a question and ask you to respond to the group.
You can pass, but I'll come back -- and some of you won't like it."  He
turned to Gina, "Why are you here?"

        "Because you told me to be," Gina replied.

        "Care to amplify?" Joe pressed.

        "Because he owes you a lot of money," she said, pointing at her
husband, "and I have to help pay it back.  I basically have to do as I'm told
until that happens."

        Crazy Joe turned his attention to Tony.  "You're being punished for
all this.  Tell us all how.  Start with why."

        Tony looked at his plate.  "I got into hock with Joe for about ten
thousand dollars.  I lost the money gambling, trying to win money to feed my
family.  I'm being punished by watching my wife get fucked by a lot of
strangers and, well, taking some of that myself.  I'm being punished by
having to watch what it has done to my family and our relationship."

        Doris' eyes were HUGE!  This kind of thing actually happened?
Looking around, she noticed that no one else seemed surprised -- even Regina.
But Regina didn't look happy...

        Crazy Joe turned to Jerome, "I'd appreciate it if you told us all why
you dislike women so much."

        Jerome grimaced.  "Mama was a whirling bitch with an eighteen-inch
ruler and a bad attitude and she had no use for men of any age.  The older I
got, the worse it got.  Grandma was worse, if anything, and I had an aunt who
was probably top of the heap when it came to bitchiness.  There were no men
in my house.  I had one sister, and she was the enemy.  When I got loose..."
He shrugged.  "The cunts I run as whores are just as bad -- stupid and
vicious and noisy and if you don't slap 'em upside the head regularly, they
get into fucking trouble."

        Crazy Joe nodded.  "Robert, you're the first of the younger set I'm
going to ask a question.  I don't think you have any cherries left.  How was
it?"

        "It was good."  Robert looked around, mildly defensive when he eyed
his parents.  "It was ALL good."

        "You were exploited at least once, and from a legal perspective
twice.  Do you FEEL exploited?" Crazy Joe asked.

        "No."

        Crazy Joe turned to Doris.  "So, Doris -- how was Robert?  Please
describe what you did with him."

        Doris blinked, looking around.  Then she looked at her plate.  "It
was good.  I got into a little tiny bikini and asked Robert to put baby oil
on me, and then I made sure he knew he could get away with things.  When he
got brave and started masturbating me, I took him in the house and gave him a
blowjob, and then we had sex.  He was an absolute stud and I loved it!"  At
the end of things, Doris, too, was eyeing people, looking defensive.

        Joe nodded.  "Note that we're not condemning anyone here.  Several of
us wanted Robert to have that encounter."  He turned to Regina, "Regina?"

        "Yes, sir."

        "How old were you when you had sex the first time?"

        "I was, um, ten, I think.  You're talking about my cherry, right?
Not blowjobs or anal?"  Regina didn't look at her mother.

        Doris' eyes were HUGE and her mouth was open wide -- but nothing was
coming out.  Finally, she got out, "WH--WHAT?"

        "Quiet, Doris," Crazy Joe admonished.  "You can start at the
beginning if you like."

        "I think Fred and I started just after I turned ten," Regina related,
looking at everything but her mother.  "We started out just playing tickle
and stuff, but his hands wandered and my hands wandered and pretty soon we
were touching each other in places we weren't supposed to."

        "Fred?" Doris muttered.

        "Fred, Momma.  Uncle Mark caught us -- caught Fred doing my butt --
and that's why he left," Regina said quietly.

        "Oh."

        "Let me finish, Momma.  Fred didn't do anything to me I didn't want
him to do.  I rubbed my puss on the lump in his pants and after a while we
decided that clothes were in the way.  He licked my puss and I sucked him.
He didn't twist my arm -- it felt good, so I did it.  His dick felt good in
my butt and it felt good in my puss -- and if he hadn't rushed things that
day going into my butt without anything to make it slippery and I hadn't
yelled, Fred would probably be here..."  Tears ran down Regina's cheeks.
"I'm sorry, Momma!"

        Doris got up and went over to console her daughter.  "It's, well,
it's all right, Sweetie."

        "Is it?" Regina sniffled.  "Is it really?  It needs to be, because
I'm still doing it!"

        "What?"  Doris exclaimed.  "With who?"

        Frankowski raised his hand.  "That would be me."

        Doris looked back and forth between them.  "But why?"

        "Because I like it!" Regina blubbered.  "Because it feels good!
Because they know how and they're nice to me!"

        "But, Honey..."

        "Boys my age can't, or won't -- or don't know how!  Mr. Frank is a
sweetheart!" Regina offered by way of explanation.

        Crazy Joe interjected at this point, "So how do you figure this
compares with, say, what you did for Robert, Doris?"

        Doris took it between the eyes.  "I...  Uhhh..." she muttered
faintly, then licked her lips.  She turned to Frankowski.  "You didn't hurt
her..."

        "No, Ma'am.  She asked for everything I gave her and was happy to get
it -- and I was happy to provide, if you know what I mean.  She was...
joyful!  It was a kick being with her!  I've never had anyone like her!"
Frankowski insisted.

        "I guess it's okay, then..." Doris said, looking dazed.

        "Oh, thank you, Momma!"  Regina caught Doris in a hug.  "Thank you,
thank you, thank you!"

        Doris turned to Frankowski, "How did you two get together?"  'Was he
cruising the school parking lot?' she wondered.

        But Frankowski turned to look at Joe.  "Joe set it up."

        "I asked Maria to ask Joe to find me someone," Regina amplified.

        "How did Maria...?  How did Joe...?"

        "Joe and I are seeing each other," Maria explained quietly.  "Regina
and I... figured out that we were doing the same thing.  I'm not as far
along, but that's because Joe is taking it slow."

        Crazy Joe sat back.  "I think we can take it as a given that Frank
and Maria have answered their questions."

        "Not totally!" Gina burst out, looking at Maria.  "Tell them why!"

        Maria sat up and looked around the table.  "Mama thinks it's because
Crazy Joe forgave thirty-five hundred dollars of Poppa's debt to get me.
Well, that was the start of it -- but it isn't all there is to it.  Mama and
Poppa are earning the thirty-five hundred anyway -- and I'm with Joe because
I WANT to be with Joe!"  She sat back, looking triumphant.  Gina covered her
face.  Tony pursed his lips and stared at his plate.

        "I guess maybe we're all unmasked, now..." Crazy Joe said quietly.
"Anyone for dessert?"

<1st attachment end>


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