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Subject: {ASSM} The Gambling Debt 13/21 {Thinking Horndog} (MF M+F MM M+M Mm Mf oral anal ir 1st noncon reluc blackmail cuck)
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Chapter 13 of 21.
<1st attachment, "Gambling_Debt_13.txt" begin>

Author: T. H. Barker (Thinking Horndog)
Title: The Gambling Debt
Part: 13 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 13

	"I have a girlfriend," Crazy Joe explained, as Hammer Thornton came
up the walk, "and I'm being faithful -- so I'll limit myself to the visuals
and watch Regina while you do the performance piece with Hammer."

	"Uh, okay..." Doris muttered, dazed.  Hammer was a big, beefy guy who
had clearly been in a fight or two.  He came through the door cautiously.

	"Boss?" Hammer asked.

	"Ms. Hicks has offered to give young Robert his first taste of
pussy," Crazy Joe explained, eyeing Doris to see her reaction, "but we all
need to see if she has her ducks in a row for the job, so we're gonna eyeball
the merchandise and then I want you to take her to her room and check her
out.  No rough stuff -- this is about whether she can seduce a kid and give
him a happy memory.  Test everything, though."

	"Okay."  Hammer seemed as confused as Doris.  "Why don't you...?"

	"I'm saving myself for my committed relationship."

	"Oh, you mean...?"

	"Yes," Crazy Joe cut him off and Hammer realized that he wouldn't
want this woman to know about Maria.  He nodded, understanding.

	"Right."  If the Boss wanted to have a 'committed relationship' with
a fourteen-year-old, it was none of Hammer's business.

	"Have a seat," Joe waved Hammer toward the couch.  "If you would show
us..." he asked Doris.

	Doris stood there, blinking.  'Did I say yes?  Yeah, I offered it...'
She flicked a glance at the kitchen.

	"I'm sure Regina has the good sense to stay out of sight," Crazy Joe
assured her.  Actually, Regina had peeked a couple of times already, and Joe
was getting a kick out of it.

	Doris popped her eyes and puffed out a sigh, then reached behind her
neck and pulled the tie loose, then grasped the bottom of the halter and
pulled it over her breasts and on up over her head.  Gravity had been given a
lot more time to work and Doris had clearly been a mother -- but her pink-
nippled cones barely sagged.  "Nice," Hammer grunted.  "They real?"

	"Yes."  Doris was mildly miffed, but it helped to counter her
embarrassment.  She undid the snap and zipper of her shorts and shoved them
and her panties off over her ass as a single unit.

	"You shave?" Hammer handled the follow-up.

	"It's thin and it looks like crap if I let it grow," Doris replied.

	"Let's see the whole show," Hammer directed, making a twirling
motion.  Doris did a three-hundred-sixty degree rotation, checking the
kitchen door in the process -- but Regina had sneaked to a position beside a
chair in the dining room.  "Nice ass," Hammer commented, "Plush.  Bring it
here."  Doris moved to Hammer and stopped before him and he directed, "Turn
around and bend over.  Spread your legs some."  He then proceeded to rub her
ass, then run his finger down the crack past her asshole and on to her puffy
pussy lips, then turn his hand over and slide it between her legs to rub her
slight pot belly -- which was of course at it's most visible, with her bent
at the waist.

	It was pretty embarrassing, but...  "Do you do this often?" Doris
asked, her voice carefully neutral.

	"Huh?  Naw -- I'm just enjoying myself.  You don't mind, do you?"
Doris' outer labia were swelling and popped open as he answered, revealing
her pink slot and the passage to her womb.  Hammer ran a finger along her
clitoral hood, up and down...

	"No, I guess not..."  Doris' voice sounded congested.

	Hammer grabbed a handful of her ass, mauling and squeezing.  "Go show
the Boss that pretty pink slot of yours."

	Doris didn't bother to argue, she just went over and presented
herself, bent over, to Crazy Joe.  Joe didn't touch her -- he didn't need to.
"Very nice."  Doris was clearly aroused.  "Have her show you her bedroom,
Hammer.  I'll wait here and entertain Regina when she comes out."  Regina
covered her mouth to keep from snorting from her hiding place by the chair --
Momma sure looked worked up!

	"It's this way..."  The way Doris took Hammer by the hand and pulled
him up from the couch was a dead giveaway -- clearly, she couldn't wait!  The
pair disappeared rapidly up the hall.

	Crazy Joe beckoned Regina, who settled on his knee, transparently
rubbing herself on it.  "Tell me, Honey -- was Daddy demanding?"

	"No, but her boyfriend after Daddy was -- he was the guy who
introduced me to sex.  He could be bossy, and a little rough, sometimes.  I
didn't mind -- Momma didn't, either," Regina related.

	"I noticed that."  Thinking back, Joe recognized several points at
which Doris COULD have been more forceful in her denials or bristled at a
request or comment.  "I don't think your momma has it in her to be a hooker
-- but she'd make someone a fine mistress."

	"I'm real hot, Uncle Joe!  Can I suck you?" Regina begged.

	"No you may not," Joe replied, "But if you lean back against me, I'll
rub your pussy.  I don't want Maria upset with me."

	"Okay."  Regina got up and stepped out of her panties and settled in
Crazy Joe's lap, leaning back and spreading her legs so his fingers had room
to work.  Joe started rubbing her nether lips with three fingers.  "Uuuhhh!
Kiss me?"

	"No.  And you need to keep the noise down, or I'll have to stop.  We
don't want your mother distracted," Joe retorted.


	Hammer was handling Doris' distractions; they'd barely gotten the
door closed to Doris' bedroom before Hammer said, "Turn on the air
conditioner."

	"I can't afford it," Doris replied.

	"I didn't ask if you could," Hammer replied.  "Just do it.  We're
gonna get all hot and sweaty if you don't."  Doris went over and turned the
unit on and came back and Hammer directed, "Kneel up and suck!"

	Doris didn't argue -- she went digging in Hammer's fly and was happy
with what she surfaced there, "Ooooo!"  It had been months and months since
she'd even SEEN a cock, and this one -- and its owner -- were making an
impression!  She set out to give her very best blowjob -- but Hammer cupped
the back of her head and made sure she gave another five percent, anyway.
Doris liked that in a man, for some odd reason; it had been a problem with
Julian, her ex, who COULD have stopped any number of arguments between them
by just being forceful and backing her down.  Fred, her boyfriend, had pushed
back many times, verbally and even physically, which made the verbal control
more legitimate; Doris knew that he wasn't just talking to feel his lips
move.  Fred had been pretty demanding, actually -- and Doris had dealt with
it and everything had been fine until her brother Mark had come along and
seen SOMETHING about Fred that he didn't like and that gave him a handle on
the man that was firm enough to get him to leave her.  There was some excuse
about there being another woman -- but Doris really wasn't the type to put a
man on the street over that; she'd have just tried harder.

	So she sucked, and enjoyed it, and didn't let the occasional push to
get him into her throat bother her.  Doris didn't just 'do' deep-throat --
but if you pulled her into your crotch, you could pop through and she would
manage not to puke on you.  Hammer did that several times.

	From Hammer's perspective, the puffy little redhead wasn't hard to
look at and delivered a pretty decent blowjob -- and he liked that she would
take a little shit from him without bitching about it.  He enjoyed her mouth
for a couple of minutes, but the Boss was probably getting bored, so he
stopped and said, "Awright, let's fuck."

	"How do you want me?"  Doris was all for it.

	"On your back, I guess.  Grab your knees."  Doris arranged herself
such that Hammer was able to address her pussy by squatting a little,
standing beside the bed -- and he pushed himself right in without farting
around about it.

	"OH!"  He was in deep, right away, and there really wasn't any issue
with lubrication or anything.  When he got going, it was GREAT, too -- better
than Fred!  "Yeah!  Yeah!  Huh!  Huh!  Go!  Go!"  After those few words,
Doris settled back to "Uh!  Uh!  Uh!" -- but the tone and the sense of
urgency changed regularly, running up the scale until she clutched at his
hands on her knees and threw her pussy up at him wild-eyed and went,
"HUUUUUHHH!!  HUUUUUUHHH!!  HUUUUUHH!!" and her pussy clamped down on his
cock.  Hammer had to stop the first time to keep from blowing a nut, but he
let her have it the second, pumping out a flood in her, silent, but making
faces that said he was too busy enjoying it to care what he looked like.
Then he backed out of her and grabbed her arm and tugged her around sideways
to the edge of the bed and presented his gooey cock.  "Clean me up."  Doris,
still disoriented from her second orgasm, opened up and sucked him in,
collecting the puddle of semen his glans had shoveled back out of her upon
his withdrawal.  Hammer grabbed her head and made sure she didn't go anywhere
until she'd finished, then said, "Put on a robe or something so we can go
back out."  He was dressed before she got organized in a short bathrobe,
waving her out impatiently.

	Regina hopped down off Crazy Joe's lap, looking somehow guilty about
something, Doris was distracted by Hammer moving abruptly to his report.
"It's good shit, Boss.  She's real... I dunno... easygoing?"

	There was something about the look on Hammer's face...  "You didn't
play too rough?" Joe asked.

	"No, no..."  Doris answered for Hammer.  "He was... a little
demanding -- but I like that."

	Crazy Joe nodded.  "Okay.  The boy is Maria's brother Robert.  Maria
is coming over tomorrow to study something or other with Regina tomorrow for
a couple of hours, and Robert will be along.  No doubt they'll sit in
Regina's room and giggle or something.  Regina assures me that they'll stay
out of the way while you see to Robert."

	"She can't afford the electric, Boss.  Can't run the A/C," Hammer
erupted.

	Joe reached in his pocket and peeled another hundred off his roll.
"If the temperatures don't moderate, you can put this against the expense."
He put the bill on the table.  "If they do, I'm sure you'll find something
else to do with it.  Are we all set?"

	"Yes."  Doris was still trying to come to grips with the turn her
afternoon had taken.

	"Thank you for your hospitality."  Joe got up and headed out.

	Hammer was more direct.  "Thanks for the fuck."  His expression said
'I'll be back' as clearly as if he'd been a Terminator.

	"You're welcome..."  It wasn't clear whether Doris' reply was meant
for Joe or for Hammer -- or both.  She gathered her robe about her and
followed the men to the screen door and watched them get into the car and
leave.  Then she turned to her daughter.  "Regina..."  She waved a finger.

	"Momma?" Regina replied warily.

	"You shouldn't have...  Never mind."  Doris gathered herself.  "What
does this Robert look like?"

	"Oh, he's HOT for a young guy!" Regina insisted.

	"For a young guy?" Doris murmured.

	"Well, yeah.  I like older guys, you know?" Regina said carefully.

	'Probably misses her father,' Doris mused, and dismissed the whole
thing.  "Okay, so he's hot, right?"

	"Very!"

	"I can't you believe you did this, but..."  She waved at the money on
the coffee table.  "We really need that.  I hope you don't think less of
me..."

	"Momma, if I hated the idea, would I help you?" Regina retorted.  "I
didn't want to see you working for some nasty ol' pimp -- and I heard about
Robert..."

	"So what happened with Robert?" Doris asked.

	Regina paused for a moment.  "Actually, it was a lot like this.
Robert had to do it -- for money, and to help his family.  The guy was real
nice to him, though."

	"Uncle Joe couldn't fix it?"

	"I guess not." Regina lied, shrugging.

	"That Joe... He sure seems stuck on his girlfriend..." Doris mused.

	"Yeah..."


	Tuesday was a day of great anticipation for Maria and Regina -- and
Doris, for that matter.  The girls planned to do homework, at some point, but
they spent most of the day trying to figure out how they were going to get to
see Regina's mother seducing Robert...

	Robert, of course, was going in blind -- he had no idea what was up.

	Crazy Joe and Hammer picked them up as had come to be the usual
thing.  Robert rode up front, as usual, too.  But Hammer, who was usually
quiet, had something to say...  "I hear you're wanting to check out pussy..."

	"Well, yeah..."

	"When I was your age, there was a lot of doors open I didn't see, you
know?  Shit blew right by me.  I guess what I'm saying is if you think you're
seeing an opportunity, you probably are.  If you kinda reach down and grab
yourself by the balls and take the chance, you might just get your dick wet."

	"Uh, thanks for the advice..." Robert stammered.

	"Look," Hammer went on, "I know Joe promised to tighten you up -- but
if you can do it yourself, it's probably better in the long run.  So I kinda
wanted to open your eyes, you know?"

	"Thanks..."

	"No problem.  I'm around."

	A couple of minutes later, they pulled up at the Hicks.  Doris came
to the door in a bikini top under a semi-transparent beach cover-up and a
short, wraparound skirt.  Hammer nudged Robert.  "I'd fuck that.  You would,
too, if you're smart.  Young bitches don't know shit about fucking -- we have
to teach them.  She knows all about dick, I bet."

	"I'll, uh, bear that in mind," Robert mumbled.  The girls were out
already, so Robert got a move on.  As Hammer pulled away, Joe's voice came
over the intercom, "Laid it on a little thick, didn't you?"

	"I figured if he was thinking about it goin' in..."

	"Yeah, probably."  Joe settled back in the limo seat.  This would
work or it wouldn't...


	Doris seemed unembarrassed at her state of dress.  "I was out back
trying to get a little more tan," she related.  "I have to get it in small
doses, or I just freckle.  The season will be over soon..."  Robert nodded,
taking her in.  Regina's mom looked a lot like Regina -- and there was a lot
to like about Regina.  If her mom was anything like her...  He scoped Doris
out of the corner of his eye, trying not to get caught at it.

	One look at Robert and all of Doris' reservations about the whole
thing fled.  He was so cute!  She had his attention, too -- he wasn't that
good at hiding his glances or schooling his expression.  'This is going to be
fun!' she decided.

	For the moment, she set him up at the dining room table -- Regina and
Maria went off to Regina's room.  "Can I get you anything?" Doris asked
Robert, bending low next to him to provide him a drop-shot for his eyeballs
between her breasts.

	"I, uh, don't think so..."  Robert couldn't tear his eyes away.

	"Don't hesitate to ask..."  Doris swayed off.

	It took ten minutes for Robert to settle down and concentrate on his
studies.  Was Ms. Hicks coming on to him?  Hammer said he should go with his
gut in such situations...  Ms. Hicks was seriously hot!  Somehow, he managed
to get going on his homework...

	Doris had gone to some effort with the planning for the seduction,
and the only real question was 'how long will it take Robert to finish his
homework?'  The answer was 'not long' -- which was a good thing, because the
afternoon sun was going to make Doris' primary gambit pretty transparent
after four o'clock.  But Robert finished quickly and started fidgeting, so
Doris was able to come in from the kitchen and move things along, "Can I get
you anything, Robert?" she asked, bending low before him, "Anything at all?"

	"Um, uh, no..."  Robert tried hard to look at her face, but Ms.
Hicks' boobs were a powerful draw.

	"Are you sure?"  Doris waited until Robert shook his head and stood
up.  "The girls probably aren't accomplishing much -- I guess your mother is
coming around eight.  Are you busy?  I wonder if you could help me with
something..."

	"Sure..."

	Doris beckoned for him to follow her to the kitchen, "The back porch
light is out.  I have a ladder, but it's kind of rickety.  I was hoping that
you might hold it for me while I change the bulb..."  The replacement bulb
was pre-positioned on the counter; Doris gathered it up and swayed out the
back door in front of Robert, her ass swaying in a wraparound that only went
to mid-thigh.  The ladder was pre-positioned, too, so it was open under the
fixture in a flash.  It was actually a tall step-stool -- and it would have
been fine, but Doris -- like Regina -- wasn't very tall.  Robert was slight,
but he was nearly a head taller at five feet eleven.

	"Uh, I could do this..." Robert offered.

	"I couldn't ask you to," Doris replied.  "If you were to fall, it
would be just terrible.  Just brace the ladder -- it'll be all right..."  Up
the ladder she went, bulb in hand -- just high enough for Robert to get an
eyeful of the lime-green thong that matched the bikini top that had been
hidden under her skirt!  The vertical strap virtually disappeared between the
cheeks of Doris' plush ass...  Doris had deliberately placed the ladder a bit
off, so she had to bend and stretch to get to the bulb.  She spread her feet
as wide as possible on the ladder step and said, "Oh, damn -- I have to lean
a bit.  Hold my legs, please?"

	Robert found himself with one foot on the bottom step of the ladder
and both arms wrapped around Doris' thighs -- with his nose nearly IN that
ass!  It was an incitement to riot -- and Robert was NOT unaffected!

	"I need just a bit more height..."  Doris stepped up with one leg and
went a bit higher -- and Robert's field of view went under the skirt to a
point where her open stance displayed the tiny panel covering her pussy at
point-blank range.  "Keep me steady, now!"  Robert clutched the stool with
one hand and a thigh with the other while he gazed, mesmerized, at Doris'
crotch.  Doris fooled around with the bulb for at least two-and-a-half
minutes, letting Robert smell her arousal along with taking in the visual
feast.  By the time she couldn't linger any longer, Robert's cock was trying
to tear its way out of his jeans!  She backed down without warning,
deliberately causing him to drive his hand into her crotch, "Oops!"

	"Sorry!" Robert lurched backward.

	"No harm done, Honey," Doris beamed at him.  "Thanks so much!  It's
wonderful having a man around to help with these things..."  She gave him a
little hug.

	"No problem, Ms.--"

	"Call me Doris, Honey -- nobody calls me that..."  Doris put the
ladder back against the wall.  Then she turned him, pretending to consider
something, and asked hesitantly, "You wouldn't mind helping me with something
else, would you?"

	"Nooo..."  'Are you kidding?' Robert thought.  'Just give me another
opportunity...'

	"It's getting late, but I can only be out in the sun for a little
while, anyway, or I burn.  Do you think...  do you think you could put some
oil on me?"  She put a hand to her mouth in a gesture that said that she knew
that she was pushing things a bit.

	"S--sure!"  'HOLY SHIT!' Robert thought, dazed.

	"Oh, good!  I'll stretch out on this lounger here on my stomach, and
you can rub it on..."  Doris pointed out the baby oil.  Reaching down, she
released the skirt.  "Do you like my suit?" she asked, posing.

	"Oh, yes!  Very nice!"  Robert, allowed to ogle openly, did so.

	"It's so nice to have my efforts to look nice appreciated," Doris
purred, then turned slowly and swayed to the lounger.  "I use baby oil
because it's good for my skin, so feel free to give me a good rub, don't just
slather it on.  Get all the little nooks and crannies..."  She spread
herself, face down, on the lounger, her head on her crossed arms.

	Robert's hands shook as he picked up the bottle.  'Give me a good
rub...  Get all the nooks and crannies...  I'm gonna cum in my pants!'

	"If you want to, you can take your jeans off so they don't get all
oily," Doris said, carefully not looking at him.  "I won't look."

	"I don't..."

	"Your mom probably wouldn't appreciate me getting oil on your jeans,"
Doris cut him off.  "Trust me."

	Robert skinned out of his jeans and went to work, Hammer's words
ringing in his ears.  'If you think you're seeing an opportunity, you
probably are...'  Robert started oiling with Doris' right calf, wondering how
he was going to keep himself under any control at all as he moved up.

	Robert had Doris well-oiled to just above her knees and was wondering
how he was going to attack the next site when Doris murmured, "Oooooh, that's
good!  I can't wait to feel your strong hands on my back...  Do you think I
should take my top off?"

	Robert drew a breath.  "Well..."

	"I'll get a tan line if I don't, won't I?" Doris queried.  "Just pop
the clasp, Honey..."  Robert undid the clasp and laid the ends aside with
shaking hands, and was just settling back when Doris added thoughtfully,
"It's a waste doing the top if I'm going to get thong marks.  Would you do
the honors?  I'll raise my butt so you can get it off..."  Robert stood
there, straddling the foot of the lounger, thinking, 'Please don't cum!
Please don't cum!  Please don't cum!' as Doris raised her ass a bit so he
could draw the thong down off it.  Somehow, he managed to get it to her knees
without stopping to blow a wad in his briefs...

	"It's working..."  The couple was in plain sight through Regina's
bedroom window.  "From the look on his face, Robert likes girls a lot!"
Regina giggled.  "And Momma's being shameless!"

	"Well..."  Maria cocked an eyebrow.  Regina's antics in Mr. Frank's
lap had been pretty shameless, too...  Regina just grinned.

	Once the thong was at knee level, Doris lowered her ass and lifted
one knee at a time to facilitate Robert's completion of the removal, then
gusted, "Please, rub me!  Go nuts -- I'm loving it!"  As soon as the thong
slid over her ankles, she spread her legs.

	Robert groaned.  Her pussy was RIGHT THERE -- and she'd given him
carte blanche!  This was EXACTLY what Hammer was talking about -- an
opportunity -- a BLATANT one!  Ms. Hicks -- Doris -- was WIDE OPEN!  All he
had to do was play his cards right...  He wormed his way between her spread
legs and started applying oil to her back.

	Shoulders, upper back, ribs...  Robert worked his way down to Doris'
ass, wondering how far he could go.  "Mmmmm, wonderful!  Don't forget the
sides..." Doris moaned.  Robert shifted back up and worked her sides, her
armpits -- and the swelling that represented the sides of her breasts as they
were mashed against the lounger.  What Robert couldn't see as he listened to
Doris' quiet groans and rubbed the sides of her breasts was the spiky nipples
poking the towel between the slats of the lounger back.  They were swollen
and needy and rubbing the towel gently to Robert's motions and throwing
sparks everywhere!  Things were rapidly reaching the point where there was a
real question regarding who was seducing whom...

	Robert backed off to start working on Doris' thighs, feeling the
confidence of his control of the situation.  Doris was hot -- he could SMELL
it and knew instinctively what it was!  She was aroused, and if things
continued as they were, she would get MORE aroused...

	"Oh, yes..." Doris crooned as Robert's hands slid up and down her
thighs.  "Get everywhere -- we don't want me to burn in tender places..."

	'If that isn't an invitation...' Robert thought.  He ran his hands up
her right thigh, pressed together at the thumbs, running parallel -- and let
the fingers of his left hand slide into the hollow on the inside that was the
atrium of Doris' pussy.  Doris' response was to moan softly.  'Okay...'
Robert shifted thighs -- and this time, he brushed Doris' swollen pussy lips
with his fingers.  Doris moaned again.  Robert gathered himself and shifted
back to the right, and this time, when he reached the top of her thigh, he
rode his right hand over her ass cheek and began kneading it while leaving
his left pressed against her pussy!  Doris' response was to shift her left
leg further out, cocking it, granting Robert full access to her pussy!  'Holy
shit!  I'm in!' Robert gasped to himself, rubbing Doris' pussy lips.

	"Ogod!  That's Heaven!" Doris moaned.

	Robert kneaded Doris' ass with his right hand while his left made
squishy noises smearing Doris' pussy juice around her split.  After a moment
or two of delighted exploration, he switched thighs again, moving his hands
up to knead her left ass cheek with his left hand while his right probed her
pussy.  Doris' split was wide open and wet and Doris moaned as he rubbed her,
finding the bump of her clitoris with his fingers.

	Doris couldn't hold out for long.  Opening her eyes, she croaked,
"Let's go inside and you can do the front!"

	Robert blinked -- THAT made no sense!  Then he grinned, realizing it
meant that they were moving on to other things...

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