Scenario: A series of episodes based around the idea of a special escort agency set up by a woman called Molly Malone and the spanking adventures of the girls who work for her.
High summer and the air simmered gently as the sun sat lazy in the sky
peeking in through the blinds of Molly Malone's office as she
interviewed the, potentually, newest recruit for her Spanking Agency. A
50 year old gentleman by the name of Bernard Bertram Bigglesworth the
Third who sat opposite her in an outfit that made him look like he had
just walked out of a 1950's catalogue and who was the bearer of a smart
slicked back grey quiff and a bushy moustache that made him look even
more like he came from another era. Molly smiled as she listened to his
lyrical tones and the way he made each word sound like a story in
itself. The man was an out and out charmer.
"...oh crikey," he said thoughtfully. "Forever and a day I suppose. The
Mater and Pater were brought up religious and strict so it was only
natural that they did the same with the six of us. Myself and five
sisters that is. Any misdemeanour or hint of mischief was met with the
strap which hung by a hook on the back of the pantry door. Many a time I
would come home to find an elder sibling yelling blue murder bent over a
fireside chair as Mater strapped seven bells out of her bare bottom. I
suppose that's where the seed was sown for this sort of thing."
Molly glanced down at his resume. "A teacher then a Headmaster?"
Bigglesworth reached up and twitched his nose. "Indeed. I was always of
an inquisitive bent. Always had a keen interest in all things and
sharing those interests with others - especially children as I grew
older. I followed the usual route in these things. Mastered at
University and got my first teaching position at a private school."
He nodded. "Yes. Quite rare back then for a private school. A good thing
for it broadened my life experience and no doubt helped when I decided
that I wanted to be a Head of my own school eventually some day."
Molly sat back in her leather chair. "So tell me how you got into this thing we do."
"Well, to be quite honest, it all came about suddenly and was completely
out of the blue." he began. "By the time of the first.." he paused as
his eyebrows rose slightly as he recalled the circumstances. "..episode,
I had been Headmaster for a mere three months at a local Grammar school
for year thirteen's and above. Basically learning on the job and,
despite the extra responsibility, was quite enjoying it as I had a good
group of support staff and teachers around me. The school was old school
in its governance and standards were set by a series of rules that were
originally outlined in the early 60's."
"For things like corporal punishment." said Molly.
"Indeed," he nodded. "Part of my remit was to mete out any punishments
that were deemed neccesary and to make sure all pupils understood the
rules of the school."
"How where those punishments dished out?"
"Depended on circumstance. The lesser evil was a bend over slightly
sandshoe across a skirt or trousers through to the greater evil of a
sturdy caning across the same. Different horses for different courses as
it were. Actually," he mused. "Canings were very rare and were always
"So, this first experience?" asked Molly.
"Her name was Miss Tait." he began. "Florence Tait. She taught English
Lit and Art History. Very well read and was well liked in the staff
room. At the time of the first session she was about 42. I'd describe
her charms as opulent." He paused. "May I be liberal with the
Molly smiled. "Please do."
Bernard cleared his throat. "All arse and tit she was. Long curly raven
hair. Blessed with a country figure. Like two copper pots on top of each
other. She always wore floral dresses even in winter and was quite old
fashioned in her manner and ways. It was early May. A Thursday from
memory. About 4pm. I was busy with some mundane task or other when there
was a knock on my study door and to my surprise I found Miss Tait
standing in front of my desk not a moment later looking decidedly
awkward. I asked her if something was amiss and she nodded. To cut a
long story short, she confessed to a matter of pricked conscience that
had troubled her for several weeks and that she had, in a moment of
madness, helped herself to a number of items for her own personal use
that were regarded as school property."
"She stole them?"
He nodded. "Apparently so, Miss Malone. Nothing missing had been noted
on the routine stock check by my secretaries recently so I was a bit
bemused by this turn of events. I always found Miss Tait to be a
stickler for rules and an upright member of staff so this was all most
alarming. I told her that I would have to report her confession to the
relevant authorities which would, in all probability, mean either a
suspension of her contract or outright dismissal. As you can imagine,
she was distraught by both her behaviour and the likely consequences of
her actions. Terrible situation all told for she was an admirable
teacher and a cherished member of my staff. I was quite perplexed and
disappointed in equal measure. But there seemed no other course of
action to take."
"So what happened next?"
"It was then it all got very peculiar," he said. "She asked if there was
some other way the matter could be dealt with without having to report
it. I must admit I was slow on the uptake at first. I asked her what she
meant and her face turned bright red. A "punishment" she said. A proper
punishment as in a physical chastisement. Well, I have to say Miss
Malone, I was completely flummoxed and flabbergasted at her suggestion!
Was she implying I should take her in hand personally and give her
bottom a good thrashing instead of reporting her? Indeed she was! There
are few times I am at a loss for words but I was rendered speechless for
a few moments. I asked her if she was serious. She nodded. Completely
serious. She explained she needed to feel as though her crime was dealt
with on a more personal level. She needed to suffer for her misdeeds.
But she said she understood if I was unwilling to deal with her in this
"So when did you decide you were willing to deal with her this way?" asked Molly.
He laughed and held his hands up. "Oh goodness, straight away of course.
I confess to the occassional day dream of taking one or two of my
female members of staff in hand and giving their big bottoms a good
spanking. But it would never ever have crossed my mind to have one of
those female members of staff I day dreamed about asking me to do if for them." He reached up and fiddled with the knot of his tie. "And who was I to say no to such an offer?!"
"No, indeed. So you spanked her?" asked Molly.
"Not the first time, no." he replied. "I realised I had to be more
formal in my attitude and punish her in a fitting manner. So I asked her
if she was sure she wanted to do this. She nodded. I told her to lock
my study door, to come over and bend over my desk. I explained that I
was going to give her bottom a good caning and that six would be over
her skirt with another six over her undergarments.I watched as she did
as she was told and was faced with her skirted bottom waiting for me to
do whatever it was I was going to do. I then went and got the school
cane from the cupboard and approached her rear. She looked over her
shoulder at me and bit her lip. Taking stance, I measured the length of
the wood and swing before tapping the business end of the rattan across
her upturned rear. "Six" I said. And six she got. I was quite firm. She
did a little gasp and dance at each of the six and I allowed her to rub
her arse to ease the sting before the final dose. I then stepped behind
her, grasped the hem of her skirt and pulled it up over her wide hips. I
will say one thing about Miss Tait, the woman has excellent taste in
French knickers and seamed stockings with garters. I was quite taken
aback by how full and tasty her bottom looked in her lingerie. Most
impressive. Several salubrious thoughts passed through my head at that
moment I must admit. Being a confirmed bachelor does have its advantages
in matters of the opposite sex. But such musings were for later and I
administered the last six cuts of the cane firmly across her beam and it
was most satisfying to hear her yelp at each one. I bade her stand up
and watched as she grasped each arsecheek and give them a furious rub to
ease the pain. "Thank you." she sighed and, to my complete surprise,
kissed me on the cheek before removing her person from the room. All in
all, a most illuminating, surreal, and rewarding experience that I
thought was the end of it. Except it wasn't of course. Far from it."
Molly watched as his gaze drifted and a smile passed his lips. What an
interesting little adventure to have she mused. "Sounds wonderful.
Please go on."
"Well, as you can imagine, the next day at the staff meeting was rather
awkward. All prim and proper but laced with overt glances between Miss
Tait and myself. I was quite fired up and had made liberal with the
experience afterwards. Rolling it around my iD as it were. Nothing more
transpired until there was another knock on my study door a week or so
later after school hours. It was Miss Tait again. She explained that she
had had another lapse of judgement and needed to be punished to free
her from guilt. Only this time she suggested I give her a good spanking
over my knee. And I did. A damned good one too. Over her skirt, over her
knickers, and at her request, over her big bare arse as well. I must
have spanked her for a good twenty minutes.
She got up, pulled her red lacey knickers over her bright red bottom and
looked at me with a glint in her eye. I was sat in my chair feeling in a
rather amused and aroused state wishing she would disappear so I could
bring some relief to the old flag pole. I'm not ashamed to admit I was
blowing steam from both ears by that time. Then Miss Tait said something
quite unexpected but completely thrilling. "Do you want me to take care
of you, Headmaster?" she asked. I blinked and said something pathetic
like "I beg your pardon?" She bit her lip and glanced down at my
impatient crotch. "Your ardour. Your thing. Do you want me to take care
of it?" she asked again. She was blushing and so was I when the penny
finally dropped I can tell you. Who was I to refuse such an exciting
invitation? I blustered something inane and nodded. Next thing I know,
and pardon the choice turn of phrase, she was sucking my cock like a
prize rhubarb and did so until I fired off a first class volley of pent
up frustration from the old walnuts. She then cleaned me up, popped me
back indoors, gave me a peck on the cheek, and left me sat there as limp
as a wet noodle wondering what the hell had happened to my well ordered
Molly sat laughing. She looked at him as he sat there with a wistful
look on his face. "Never underestimate a woman's cunning when she gets
an idea into her head, Mr Bigglesworth. Especially an idea regarding
sex." she grinned.
Bernard blew out his cheeks. "And that's not even the end of it!" he exclaimed.
"There's more?!" laughed Molly harder.
He nodded. "A few days later, a Friday, after school hours, I was
writing and checking reports in my study when there was a knock on the
door. It was Miss Tait again. Only this time she wasn't alone."
"There was someone else?" exclaimed Molly. The man was turning out to be the Indiana Jones of spanking.
"Miss Tompkins. Geography. About 25. Tall. Blonde. Very slim. Quite
bosomy. Quite shy when talking to her. Not one to put the first foot
forward. Miss Tait turned and told her to come in as it would be
"alright." You can imagine my reaction. Stunned amazement and a
rocketting libido. Next thing I know Miss Tait is explaining that they
had both been bad girls and needed to be dealt with right now. She went
on to say that Miss Tompkins was of like mind and that she was agreeable
to "anything and everything" that would transpire from there on in.
I stood up and asked Miss Tompkins if she understood what that meant.
She nodded. "Yes sir." Sensing that they both wanted me to take control
of the situation, I told them I was going to give them each a good hand
spanking on the bare arse followed by a good slapping with my leather
Then I had a moment of inspired inspiration and told them I was going to
do all this after they had removed all their clothes and had sucked me
off first as I reasoned that having a raging hard on would affect my
ability to administer their punishments dilligently. They both glanced
at each other then said "Yes sir." I walked over, locked the door and
stood watching as they each stripped naked. A most impressive sight it
was. Once naked, they came forward, pushed me against my desk so that I
was leant back against it. Miss Tompkins undid my zipper, reached in,
and extracted my fast extending member and gave it a jolly good wanking
before she offered it to a similiarly kneeling Miss Tait who took it
into her mouth and sucked on the knob end for all she was worth. For the
next five minutes they passed my prick between them, laughing and
giggling, and eventually made me spurt a not inconsiderable amount of
jungle juice over their proffered bosoms.
A most splendid time was had by all. Then I spanked them both. One
after the other. Hard spanking. Hard enough for them to cry out in pain.
Hot red arses for them both. After a short period of recuperation, I
made them stand side by side, naked, bent over my desk with their arses
in the air and I then belted them enthusiastically with my leather belt
for a good ten minutes. By the time I was done their backsides were all
shades of mottley hues and they came over to offer me kisses and
thanking me for dealing with them in such a stern fashion. I thought
that was that but no. Miss Tompkins sighed that her pussy was all wet
and that a good hard fucking was the only way she was going to ease the
itch inside. So they helped me to remove my clothes and we all ended up
shagging each other silly for the next hour or so. I was quite worn out
when we called it a day. A month later and, as time and events unfolded,
I'm surprised I didn't end up in hospital considering how our little
Molly blinked. "Expanded? How many women did you end up dealing with?!"
Mr Biggleworth flapped his hand in the air and looked to the ceiling. "Oh, by the end of term it was about five."
"FIVE?!!" gasped Molly.
He gave her a wink. "I guess word spread through the female members in
the school staff room that their dear old Headmaster was a vigorous
spanker of naughty big girl's bottoms and wasn't averse to the odd
session of kinky sex either." He looked at his would be new employer. "
You're not shocked are you , Miss Malone?"
Molly shook her head. "Not a bit," she laughed. "By the way, you're hired. Welcome aboard the Spanking Agency."
Author Notes. Whew, first story in
awhile. Bit rusty but think it's a nice way to get back into the swing
of things again writing wise. Doing a story for The SPANKING AGENCY is
always a fun experience and I've wanted to get a more mature man into
the mix as it opens up one of the aspects of spanking that interests me -
older man/younger woman stories. Hope you enjoy reading it and will
post more spank fiction as and when. Ian.