High Roller by Lance
Without looking up Ollie knew it was Jenny. His face burned
with shame as she reached out to take his hand. He didn't want to be led out of
the casino like this but considering his immediate situation Ollie wasn’t in
any position to complain. With minimum conversation she gave him the money
needed to get his car out of the parking building and suggested he follow her
home without delay.
Jenny was his second wife; his first marriage was just as
his friend’s warned a total disaster, this was primarily due to his lack of
maturity and consideration toward anyone else. Eventually he met Jenny who was
considerably older and far more assertive. She soon witnesses what appeared to
be some child like nonsense and being rather intuitive she began to wonder if
her strong young lover might have some unusual behavioural issues. It was
during the height of passion that Jenny was clever enough to extract his most secret
desires. Ollie needed a mommy just as much as he needed a wife. Fortunately Ollie refused to listen to his
friend’s advice to stay well clear of this bossy cow and it wasn’t long before
they married. The marriage proved to be a success much to the bewilderment of
family and Friends who still to this day have no idea how this marriage works.
As Ollie drove home he couldn’t believe how stupid he had
been, if only he had quit while he was ahead, if only he hadn’t gone in at all.
He knew he had a gambling problem, they had discussed it and he knew he wasn’t
to go inside any casino. He had broken one of her golden rules and now he would
have to face the consequences.
The moment Ollie arrived home he went straight to the
bedroom. It was only 2.30 in the afternoon but he didn’t need to be told take a
shower and get ready for bed. Normally Jenny would tell him it will soon be
bedtime and put his pyjamas on, but this wasn’t his normal 7.30pm bedtime.
This was a nightie spanking.
Putting his nightie on was his way of telling Jenny he was
feeling very guilty and desperately wanted her to make everything better again.
An over the knee Pyjama spanking although unpleasant wasn’t anywhere as bad as
a nightie spanking. Putting his nightie on was effectively asking for a hard
spanking with her hairbrush and the added humiliation of being diapered. Even
though he didn’t want it, deep down he knew he deserved it and putting on his
winceyette nightie would ensure he’d not only be well and truly punished but
he’d also, truly forgiven.
Now sitting quietly of the side of his bed he could hear
Jenny down stairs tiding up the kitchen. He knew only to well she would soon be
up to deal with him. She’ll see him quietly waiting in his pink winceyette
nightie with the lovely bodice embroidery and nodding her head in sympathetic
approval she’ll open her panty drawer and take out that hairbrush of hers.
She had spotted this
horrid old brush in a collectables store and discreetly commenting on how
effective she thought it might be, when she noticed Ollie turn bright red with
embarrassment she just had to buy it. This wasn’t one of those modern
lightweight plastic ones. This hairbrush was more of an antique. It was fairly
large, oval in shape and made of a shiny dark hardwood. She called it her magic
brush because when liberally applied to Ollie’s bare bottom it could magically turn
him into a very obedient little boy and in the days that immediately followed,
her young husband would be far more respectful and very loving.
He hated feeling so miserable. He wished his wife could
simply forgive him and after a hug everything would be okay again, but he knew
it wasn’t going to be so easy. He had broken a golden rule and that meant an
early bedtime with a very sore bottom.
Evenly the door slowly opened, it was time and Ollie’s heart
pounded as he watched her open her panties drawer and take out that brush.
Sitting on the bed beside him she took hold of Ollie’s hand.
"Everything's going to be okay she whispered. I love you, you know that
don’t you?"
I-I'm sorry, sweetheart,” Ollie blurted out. "I'm
really, _really_ sorry."
"I know, dear. I know."
"Please don't be mad. I didn't mean to do it. I don't
know what came over me."
Her eyes became large and serious. "It was wrong for
you to go back to the casino, you know our agreement.”
"I know, sweetheart. I'm really sorry. I wasn't
thinking."
"You obviously feel you need a really good spanking,
you’ve got your nightie on, and so I can only assume you admit to deserving
one”
Ollie nodded his head; he understood his fate only to well.
"Oh darling, please! I'll be good, I promise. I'll never go in to a casino
ever again! I promise!"
"You said that last time dear and if I don’t help you,
you could very well do the same thing tomorrow. You must learn to think. You
are an intelligent young man -- and intelligent men do not gamble away all their
allowance.
Ollie looked around frantically, praying, hoping against
hope that something would save him. At first Jenny had been so nice and
understanding he'd thought that this time, just maybe... but in his heart of
hearts he knew there was no escape. In a moment he'd be back over her lap
having the gambler walloped out of him. The image made Ollie tremble.
"Please, dear," he begged, sliding to the floor on
his knees. "Please ma’am, don't spank me so hard”
"That’s enough," she whispered patted her lap.
"Come on, be a good boy and get across my lap please dear."
Ollie found him self-standing and a moment later he was head
down over her knee. It was such a bizarre position. He hated this so much, he
felt so helpless and out of control. All he could think about was how much he
wanted to get up; it was so unfair. Ollie knew he had been disobedient but he
was sorry and he told her he'd never, do it again.
Why couldn't she give me a break, just this once? Other boys
my age go to the casino and do much worse things but none of them ever get
spanked.
With her soft voice quietly scolding him, he whimpered as
she slipped his nightie up clear of his bottom. "Quiet now. Everything is
okay. "You've been a very naughty boy and you're going to have to take
your medicine. We both know I wouldn’t have to do this if your mother had taken
care of you when you where a little boy, don’t we?
Yes Ma’am.
So now it’s up to me to do mommies job for you isn’t it?
Yes Ma’am I guess so.
You know it's going to hurt, but you also know I'm only doing
this because I love you so much and we also know this is what you truly need
from me isn’t it? ”
"Please, ma’am, don’t spank me--"
"Not another word, young man!" she said in that
stern voice she has at times like this. She followed her command with a hefty
swat of her big hairbrush and as it smacked down on Ollie’s bare bottom her
young husband gave a shriek of legitimate terror. Soon the unmistakeable sounds
of an old fashioned spanking filled ever room in the house. He gasped and
howled as her brush rose and fell with deliberate intention to case the pain
that was needed. Ollie kicked and pleaded unashamedly, but Jenny was determined.
She gave him exactly what he needed, a real full on bare bottom spanking. She
smacked away until his bottom was bright red all over, and her young husband
was transformed into a well-spanked little boy, full of remorse and crying real
tears.
There, there now, up you get she said, finally putting her
hairbrush aside and waiting for him to stand.
Ollie tried unsuccessfully to wipe away his flowing tears as
he continued crying and gasping for breath.
Wrapping her arms around him she held him close. “I love my
little boy so very much," you know that don’t you Ollie. No matter what
happens, no matter what you do, no matter how many times I have to punish you –
Mommy loves you more than anything else in the whole world!"
Pushing Ollie gently back she stared into his tear filled
eyes. "Do you understand me? Nothing you do can ever change that. Yes, I
have to use my hairbrush, but it's over quickly, and you know you can trust me,
I’d never tell anyone you still need to go over mommy’s knee. You do trust me
don’t you?
"Yes mommy," he gasped hugging his wife as he
continued sobbing.
He felt so warm and secure; this was the part of his
childhood that had always been missing. Fortunately he had found a very special
wife that understood his bizarre need for her to not only love him but to also
be the strict mommy he so desperately required in his supposed adult life.
Off you go now she
whispered.
Yes mommy.
She watched in
admiration as her very obedient little boy gingerly took up his position in the
corner of the bedroom. It was a sight she had come to enjoy; he would now be
required to stand facing the corner for the next hour. Having to stand with his
nightie held up displaying his bright red bottom comes with an advantage. Ollie
is able hold the front of his nightie against his face, muffle his sobbing and
wipe away his flowing tears.
$20.00’s well invested Jenny thought to herself as she
returned the hairbrush to her draw. He’ll be extremely respectful and very
passionate; the sex is going to be heavenly, he’ll strive to please me for at
least a week. Yes indeed, best investment I ever made….
Such are the rewards
for any wife who takes the time to fully understand her husband. Eventually
you’ll discover that deep down, all husbands are just naughty little boy that
will always need your maternal guidance and lots of discipline.
“I’ll have one hour
of nice quite corner time thank you Ollie and then I’ll be back to put you in a
diaper and tuck you into bed. I bet a week of 6.00 o’clock diapered bedtimes
will do your gambling the world young man?”
“A week?” He asked astonished.
“Do you want to raze it by a week of very sore bottoms as
well”?
“No mommy”.
“Well best you don’t gamble with fate, now face that corner
and be very quiet”?
“Yes mommy, thank you Mommy”.
“That’s much
better”.
The End
Omg,I'm squirming with a trouser tent!
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