It must be that time of year. A visit to Whipstock Grange beckons shortly where, under the tutelage of a stern headmaster and formidable mistress, schoolboy days shall lovingly be recreated. Pants come down and bare bottoms are caned and strapped, and the only difference from real schooldays is that those of us whacked bear it all willingly. It was never thus at my old secondary modern. There whackings were rife but recipients reluctant. The only common denominator was, I am sure, that the cane wielders of yesterday enjoyed smacking bottoms as much as the folks at Whipstock. They just had to pretend they didn't. Musing on all this has sparked a rich seam of stories. Knocked out four in the last few weeks, including the long opus called Harry and Alexandra. Saving that until the end of the month. This is a small one, purely for light amusement. A shy man buys a raffle ticket and wins a prize that you would never get on the National Lottery. If you don't like it think of me getting my due at a certain establishment. Who knows, perhaps Edwin Chitterson might be there. Alfred Roy
Edwin Chitterson was not a particularly interesting chap. He
had few hobbies and a singular lack of interest in sport. He did not join
clubs, cultural or social, and rarely ventured out in the evenings. He had
never married and did not make friends easily. He left school when he was
sixteen and for the last twenty years worked, meticulously and methodically, in
the local bank. He wasn’t a loner or a misfit, just not interested in the
general raft of activities. He preferred his own company. He read widely and
visited numerous architectural sites. Castles and cathedrals, monasteries and
stately homes captivated. But always on his own. It was not an interest he
could share. I suppose you would say he was shy. But even the shy have their
own hidden desires and passions, often unbeknown to themselves, and Edwin
Chitterson discovered his on the day he won a raffle prize.
Against his better judgement he was persuaded to attend an
upmarket adult charity dinner with some of his bank colleagues. The word
‘adult’ should have triggered a warning. It was a large, well intentioned,
event and, under the respectable cloak of charity raising, almost anything was
permissible. A sponsored ‘skinny dip’ in the hotel pool raised over five
hundred pounds, an auction of a variety of dubious objects raised another three
hundred, and in the true spirit of the evening a prize was given to the person
who attended the dinner in the most outrageous outfit. Edwin Chitterson
indulged in none of these things. He attended the dinner in sober and
unimaginative clothes, he did not strip for the uninviting pool, and he
declined to bid for any of the auctioned objects. He was singularly
disinterested in purchasing a turkey baster, failing to understand the laughter
this object produced, and easily resisted a leather outfit clearly designed for
an overweight midget. His only temptation, an antiquarian book on Deviant
Sexuality, was equally passed over. Much as he was attracted to the book he was
not prepared to make that interest public. But with some reluctance he did
purchase two tickets, at two pounds and fifty pence each, for a kinky raffle.
It seemed harmless enough by the standards of the event and besides, he
reasoned, he was unlikely to win. But win he did. Not the first prize, a £250
voucher for a health farm, but one of the three mystery runner up prizes. Each
valued at £100.
His was the second of the three runners up numbers to be
called. Self consciously he made his way to the top table and hastily chose one
of two brightly coloured envelopes remaining. The first runner up had picked up
a gold envelope and as Edwin returned to his table with a garish red one he
heard raucous laughter. He placed the envelope in his jacket pocket, refusing
all pleas to open it, and considered it a wise decision. The gold envelope
contained a voucher for a sensuous massage at a well known local establishment.
Hence the laughter from an adjacent table. Before he left he discovered that
the third envelope, glitzy silver, contained Ann Summers vouchers. When pressed he said he had opened his and it
contained gift tokens for quality books on erotica. He doubted if he would take
advantage of it. Other than that he refused all requests to elaborate.
He had not opened it. He did not know what the envelope contained.
Saying it contained invitations to erotic books seemed a mild response, in the
context of the event, and it served its purpose. A little probing, a little
teasing, and mildly inebriated minds moved on to more interesting matters. He
congratulated himself on his deflection of salacious interest. Sensuous
massages and sexual artefacts clearly had more appeal than books. Regardless of
content. But Edwin Chitterson would not be a normal, curious, person if he did
not muse on what strange promise the envelope actually held. He was naturally
eager to get home and open his prize in the privacy of his flat. When he did
so, after a suitable interval, he nervously opened the shiny red envelope and
read the details of the high quality, beautifully printed, voucher it
contained. He read it at least three times before he totally absorbed the
contents and its possible implications.
Congratulations.
You have won a free, one hour, consultation:-
with
Mistress Emerald
Corrective and Sexual Therapist
Newcomers Welcome
See reverse of voucher for contact details
Edwin Chitterson turned the voucher over and read the details
of the telephone number and the consultation times. His first instinct was to
tear it up and dismiss it. But the more he thought about it the more he was
attracted to the proposition. He retired that evening in a pleasant if nervous
state. The prospect of Mistress Emerald had strangely produced a warm and rare
stirring in his loins. He would spend a long and sleepless night.
It took him about three days to pluck up the courage to ring
the number. When he did he immediately relaxed. Mistress Emerald was a softly
spoken mature lady with an understanding approach. And the fact that he won a
consultation with her in the charity raffle singled him out as a different sort
of enquirer. He quickly elicited the fact that she had lost her younger brother
to the obscure disease the charity dinner was supporting and her involvement
became clear. He also gathered that she had attended the dinner as a guest and
was aware that the red envelope contained her donation. Her comment that she
rather hoped that the shy young man who had won would take advantage of the
prize both excited and unnerved him. After some probing he admitted that he had
never visited such a person in his life but that the services on offer appealed
to his nature. She laughed gently and posited a crucial question. Did he wish
to visit her for a chat, some clients did, or did he wish to experience her
full services? Edwin Chitterson fell silent for a moment and took a deep
breath. He would like her full services. Providing she acknowledged he was a
novice in such matters. In for a penny in for a pound she said. Or in his case,
two pounds and fifty pence. He smiled and they fixed up a date and time. He replaced
the phone and, sitting down, realised he was sweating profusely.
He found her address quite easily. The drive was sixteen
miles but he had, fortuitously, picked a pleasant day and the traffic was
light. He parked as instructed, a local supermarket with a free two hour stay,
and walked to the block of flats indicated in the conversation. It was a small,
attractively built, block with a nicely laid garden of shrubs and trees. He was
just about to phone her to say he had arrived and obtain her flat number when
he received a small shock to his system. Already agitated in nervous
anticipation his anxiety notched up a level when a girl he slightly knew
emerged from the building. She worked for a rival bank and had been a guest at
the charity dinner on an adjacent table. She smiled when she saw him but
quickly passed. He was relieved that she did not stop to speak as he was
uncertain as to what he would say. But the proximity of someone who knew he had
won a prize in a dubious raffle at the place where he intended to claim its
promise created disturbances in his demeanour. It was a combination that did
not appeal to the cautious and shy Edwin Chitterson. Instincts to abandon his
appointment vied with his desire for a watershed experience. He had never done
anything in his life. All adventures, especially sexual ones, took place in his
head. And dominant women figured large in such dreaming. He could not deny
himself this deep seated need. The raffle ticket had given him an unexpected
opportunity. He could not let a fleeting meeting with a vague acquaintance
thwart it. He phoned the advertised mobile number and, five minutes later, pressed
the appropriate bell.
He knew not what to expect. He said hello when she opened her
door and stepped in when invited. She smiled back and directed him to a large
and comfy room. She was older than he thought, possibly early forties, average
height and slimly built. Her dark hair matched her dark and simple dress. She
wore little make up and no jewellery. The room was scattered with comfy chairs
and cushions and was clearly her living area. Books, flowers, and glassware
bedecked tastefully walled shelves. The central area of the room, beautifully
carpeted, was clear of any furniture other than a small empty table at the
furthest end. Its bleakness contrasted unfavourably with the rest of the
furnishings. She said nothing other than a reminder that he had requested they
did not converse until after the consultation. And that ceased when he decided.
She bid him to remove his shoes and stand in the centre of the carpeted area
and close his eyes. When he did so she stood behind him and placed a blindfold
over them. For a moment there was silence and darkness and then Edwin sensed
his jacket being removed. Then he felt delicate hands loosening his tie and
undoing his shirt. He held his breath and stood as still as he could. He felt
his shirt being released and taken from his body. It was a long slow process
but soon he was down to his under vest. And then those same delicate hands
undid the belt on his trousers and, tantalisingly, released the button that
held them up. No woman, no person, had ever done this to Edwin. Now it was
happening and he could not see. Slowly his zip was pulled down and those same
hands deftly lowered his trousers to his feet. She did not ask him to step out
of them so they remained where they fell. Never had he felt so vulnerable and
never had he wondered more on what was to happen to him next. He had no desire
for the sensations to cease and was aware that his excitement was becoming
evident. Not only to him but to his silent tormentor. The delicate hands, hands
that had expertly undressed him so far, gently lowered his underpants. Slowly
over his hips and down his thighs, past his trembling knees, and finally to his
feet. Now he was virtually naked, other than the vest and he drank in the
sensation of his release. Again there was silence and stillness. And then he
felt those same hands and soft fingers gently brush his shaft and cup his
filling balls. Soon the whole of his manhood, rigid now, drank in the exquisite
unfamiliar. Exploring, probing, holding. The pubic hairs, the long penis, the
smooth testicles. All touched and investigated. Edwin thought he would faint at
such heavenly sensations. And then it stopped. Silence again. Stillness.
Darkness. A vest being lifted. Removed. Naked. A hand, a gentle hand, lightly
touching his bottom. Sensations now behind him, desire in front. The hand
lingered, cupped each cheek, probed and explored again. Including the crack in
between. And then, a smack, a thwack, a feeling of leather, pain, sharp pain, a
warming strike. Across his backside. Light at first, and then firmer, harder,
quicker. Six, eight, twelve. Sharp whacks across his behind. Stinging, hurting,
pleasant. And he never lost an inch of his thrusting desire. He drank in the
burning behind him and the surging in front of him and prayed, eyes firmly
closed in the darkness, that it would never end.
He waited, expecting more pain or probing. Then hands at his
feet, removing his fallen trousers, his underpants, his socks. Edwin, totally
naked, with a woman he could not see or hear. Only sense. And then the tying.
Something around the base of his shaft. Cold. Hard. Tight. More rigidity. And
hands taking his, leading him forward. His waist, sweating and warm, touching
against cold wood. The table. Pushed down. Bent over. Legs firmly spread,
constricted balls and cock hanging free. And something cold touching his
bottom. Cold and hard. Like the table. Smooth and thin. And tapping, across his
raised and naked cheeks. A cane, he thought. It must be a cane. He trembled,
his desire surged. The cane struck him, light at first and then harder. He
raised himself to welcome it. Harder he seemed to be saying, harder please. The
cane struck again, lashed at him, and his juices continued their relentless
rising. On around the twentieth stroke, the twentieth or more slash of the
unseen cane to his naked backside, Edwin Chitterson ejaculated. Exploded.
Released all the seed in him that had lay dormant for weeks or months. The
flood of his juices, spurred on by the stinging fire of a cane, left him in
heavenly throbbing spurts that seemed never to cease. Until his body collapsed
in sheer exhaustion at the enormity of the experience. As glowing inner warmth
surrounded him he released gentle tears of joy. It had all taken no more than
twenty minutes.
He dressed and they chatted. Over a warming cup of tea and a
filling piece of homemade cake. Victoria sponge, so light it melted in the
mouth. He had enjoyed the experience, wished to see her again. As a paying
client. Her sensuous attentions had released something in his repressed
personality. He told her about his life, his architectural interests, his job.
She told him a little about hers. About her late brother and the disease that
killed him, long and slow and painful. And about her sister, the girl who had
left the building when he arrived. This information initially disturbed him.
Would he have rung her bell if he had known that? She saw the concern on his
face. She knows what I do, she said, but she is very discreet and does not
condemn. It was her who persuaded me to support the charity, she said. She had
called in to tell her to take it gently with a very shy man she admired. Edwin
Chitterson absorbed all this and had no regrets. Mistress Emerald, corrective
and sexual therapist, had been a promise well worth winning. He could not talk
about it, did not want to talk about it, but he would remember it and replay
it. Two pounds and fifty pence, twenty heavenly minutes. It was a different,
more contented, man who left the building. He had played a raffle, grasped its
unexpected prize, and rejoiced. If he sang on the way home no one should be
surprised.
Alfred Roy (2013)
See Also - I Have Never Seen Whipstock Grange / Whipstock Revisited
To Come:
Harry and Alexandra (FM/fm)
The New Neighbour (M/m)
Crying for the Cane (M/m)
Mrs Wilmer meets Miss Jones (F/f)