Lady Sheffiels’s Chess Match

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Lady Charlotte Sheffield enjoyed watching chess matches while she took her afternoon tea. Not that Charlotte was an intellectual snob. Not at all. You see her chess matches were conducted to satisfy her erotic fetish; to see two men trying to concentrate under the most trying of conditions. Competency at the game was of course important, but equally so was self-control.

The rules were simply. Acceptance of an invitation merited a fee. It didn’t take much of one to entice young chess players of average skill who were akin to the proverbial starving artists.

The games were timed with each player given fifteen minutes. Running out of time meant a loss and what a loss entailed. The loser would be caned by the winner to her ladyship’s heart content. And what a big heart she had.

As If this all didn’t provide enough stress the players would be sexually stimulated by two young, unseen house servants working over their privates beneath the game table. Were a player to succumb during play and ejaculate he would immediately lose the match.

Oh what fun!

“My Lady,” said the butler. “Here are the contestants for this afternoon’s match.”

Charlotte looked up from her wing chair which sat atop a step giving it an air of a mini-throne there in her Great Room. Both of the young men were wearing modified tuxedos which the butler had had them exchange for their street clothes. The modifications were that they were wearing white dickeys with black bowties and black skirts which could be spread open at the front.

“My Lady, I’m Henri Bonnet. I do so appreciate the invitation,” said one as he bowed and kissed her extended hand.

“You don’t sound French,” she said as she looked down at the man in his mid-twenties wearing black horn rim eyeglasses. He appeared to be a borderline nerd.

“No ma’am. My departed father was from Paris. No, I am quite British.”

“Then you’ve had the cane?”

“Most certainly. But today I plan to do the caning,” he said as he gave a smirk to his opponent standing beside him.

As he slowly straighten up he stared at the rattan cane there in Her Ladyship’s lap. Lord it looked vicious. Truly man-sized and of a raw texture.

“My Lady, I’m Bruce Hathaway. Such a pleasure in meeting you,” said the other with a shy bow.

Charlotte looked him over carefully. This Bruce was likely gay. Then all shy young men were certainly not gay. But his pale white skin and sandy hair and blue eyes would clearly turn on gays. Certainly he had been exposed to the gay community, if nothing else. Charlotte extended her hand.

Bruce looked at her hand which demanded attention. With trepidation he took it and kissed while his eyes remained riveted on the monstrous cane there in her lap. He had expected a school cane; not this horrid thing.

“Your tea, my Lady,” said the Butler as he presented a tray.

“Thank you, James.”

“Mister Hathaway; Mister Bonnet.”

The two men took their teacups and saucers.

“Tell me gentlemen, are you up to date with the latest chess conventions?”

The two looked at each other, questionably. “I assume so, my lady,” replied Henri.

“So you know the Bucharest Gambit and the Sicilian Slant; the Mondovi Movement and the King Arthur Flanker?”

The two young men’s mouths dropped open. Slowly they turned to look at each other as if to say what? Then Charlotte laughed.

“Just kidding, young men. They only exist in my head.”

Both sighed in relief and took sips of their tea while still standing there before the throne in their formal attire, mindful that they were wearing black long skirts rather than trousers.

At that moment they heard a girlish giggle come from beneath the chess table over which a ruby colored sheet was draped. Lord but they sounded young with girlish glee. Charlotte smiled.

“So you know the rules, gentlemen?”

“Yes ma’am. Fifteen minute limits and the loser gets the . . . gets the . . .”

“This,” replied Charlotte as she pointed down at the horrid cane there on her lap. “I call her Betsy.”

“Right. On the bare?”\

“Of course.”

“How many, ma’am?”

“However many I wish, naturally. You do ask rather silly questions.”

“Yes ma’am. Sorry,” replied the sandy-haired shy one. “This format is rather new to me.”

“Then do take your seats gentlemen and let the game begin.”

– – – – – – – – – – –

The two shy young men took their seats facing each other. They put their teacups and saucers down and studied the timers. Only then did the butler present the chessboard and chess players. Now the rumors they had heard were confirmed. The chess pieces were custom made.

The pawns were three year-old naked boys postured to pee with their hands on their hips. They appeared to be made of porcelain. The knights were on horseback with their naked buns raised on high like racehorse jockeys. The bishops had their cocks and balls outside of their priestly gowns.

The king was a king-sized cock raised on high with a royal crown atop its cock’s nob. xslot The Queen was a pole dancer whose crown was atop her pole. As if the game format wasn’t already challenging enough!

As Henri was studying his opponents big bad black cock-king the butler started his clock. Quickly he advanced one of his peeing boy pawns and hit his timer-clock which started Bruce’s.

It wasn’t until three moves later that the house servant girls began to make their presence known by making their own moves. Just as Bruce had lifted his knight he felt his skirt pulled apart beneath the table followed by a feminine hand placed midway up his thigh. Suddenly he didn’t know where to put his knight down.

At the same time Henri felt his skirt pulled apart and the room air on his privates. Lady Sheffield noted the startled look on the young men’s faces and smiled as she took another sip of her tea. Bruce was still trying to determine where to set his knight down. The knight’s naked butt up in the air like that didn’t help his concentration. Ding went the timer-clock as his knight took a pee-boy pawn.

Feeling the pressure of the timer Henri took a black pawn only to have Bruce take his knight with his black bishop with his big bad black cock standing upright out of his robe. Take that, implied the bishop. As is that wasn’t enough the ding of his timer was heard, adding to the pressure.

Down below feminine hands began to caress the inner thighs of the two players. Both Bruce and Henri rose to the occasion. Below the table, that is.

Charlotte took another sip of tea as she saw the two young men squirm and begin to pant. Panting in lust was not inductive to intellectual thought processes.

A frenzy of piss-boy pawn exchanges were made as Bruce felt a tongue begin to lick his balls and as Henri felt his nuts cupped in one hand and his shaft begin to be licked.

“How’s it going, Brucee-boy,” inquired Henri with a smirk as he hit his timer.

“Screw you.” Ding.

“I’m sure you would like that.” Ding.

Now Bruce’s balls were cupped and began to be gently squeezed as a tongue licked his shaft. “Shit.”

“Is there some problem Bruce,” inquired Lady Sheffield.

“No ma’am; no problem. SHIT!”

“I hate to point this out Bruce, but aren’t you beginning to run a tad low on time,” said Charlotte with a smile.

As Bruce stole a glance at his timer he felt his knob enter a warm female mouth as his nuts continued to be squeezed and un-squeezed. Must think; must think, he instructed his brain. Unfortunately his brain had other things on its mind, namely his cock and balls. In his haste he made a significant error.

“Check.” DING

“What? Oh shit.”

But Henri’s little victory was short lived as he felt his knob enter a warm mouth as his balls continued to be messaged. God but did he ever want to thrust.

As Bruce attempted to study his dire situation he felt that mouth over his cock-knob move down onto his shaft as his balls continued to be manipulated.

Must think; must think.

“Gentlemen,” interrupted the butler. “Fair warning that Mister Bonnet has three minutes thirty-five seconds now remaining and that Mister Hathaway has one minute ten seconds remaining. Thank you.”

“Might we take a time-out,” asked Bruce.

Lady Sheffield chuckled. “That’s cute.”

Tick tick tick tick

Talk about pressure! There was the pressure of the match, the pressure of the clock and the pressure in the cocks beneath the table inside of your servants’ mouths.

Bruce move a piece quickly to place his king out of check for the moment. He hit his timer. Ding.

Henri had just about decided on his next move when he felt that warm mouth about his knob quickly advance until he felt a feminine nose abut his abdomen. Now he wasn’t quite sure.

Tick tick tick tick

Feeling a momentary sense of relief in knowing that the clock was now running down for Henri, Bruce relaxed a bit. That was the moment that his cock entered the throat of the lass down below. He gasp as his head lifted up towards the ceiling. Will he come now, wondered Lady Sheffield?

Both men now had to struggle in not ejaculating. Oh God no. Don’t cum, boy; don’t.

“Check. Check mate,” announced Henri with his next move. Fortunately that proved enough of a shock to keep Bruce from cuming. But unfortunate in that he had lost.

The two house servants abruptly belayed their affections. Quickly they pinned the men’s black skirts back to keep their fronts and their rock-hard, unsatisfied cocks exposed. Her Ladyship would certainly want to watch their manhood as one delivered the horrid cane and the other accepted it. Often she had seen the caner’s cock remain on high while the canee’s cock withered. But one never knew. Individual differences, you know.

“Bravo, Henri. You are my champion.”

With that Lady Sheffield extended the horrid cane. Henri had no choice but to stand up to accept the honor. As he did so with a bow Charlotte studied his wet goodies which were xslot Giriş in a black forest which matched the color of his black horn rim glasses.

“Mister Hathaway, if you would rise and present yourself to her ladyship,” instructed the butler who now had a towel draped over his arm like a waiter.

Bruce’s face blushed as he too now rose and took his stance beside Henri. Charlotte studied his wet, unsatisfied cock and balls and couldn’t help but make the comparison.

“Why Bruce. What a big cock you have.”

“Thank you, my lady.”

“Quite the handsome one, I should say.”

“And your pubic hair. Why it’s the same sandy color of your head hair. Did you realize that?”

“Yes ma’am. I’ve been told.”

Bruce’s blush deepened as Henri looked down with envy.

“Butler. A blue ribbon, please.”

“Certainly, my lady.”

That said the butler proceeded to tie a blue ribbon about Bruce’s upright cock.

Lady Sheffield gave a polite hand-applause.

“Now Henri, if you would be so kind as to beat the shit out of this wimp. I want his losing ass to be thoroughly welted, you understand.”

Both men recoiled at the Her Ladyship’s abrupt change in language and attitude.

“Ugh; certainly. With pleasure, my lady.”

At this juncture the butler relieved both men of their tux coats leaving only their short white dickeys and bow ties above their waists. He also removed Bruce’s black skirt. Henri’s skirt remained on but with the front still pinned back to reveal his cock which appeared to have even become more rigid in his knowing that he was about to cane the sandy-haired Bruce. The young man now resembled an orchestra conductor wearing black tails, save for the detail that his front was bare from his dickey down.

The butler had Bruce stand right in from of her ladyship seated on her elevated throne with his legs spread and his hands behind his head. It looked as if he were offering his cock and balls to her in tribute, which was true. Of course he was also now offering his bare ass to Henri while the butler stood at one side with discrete, sophisticated attention.

“Would you like more tea before we begin, Mr. Hathaway,” offered Charlotte.

At first Bruce couldn’t believe his ears. But while she patiently waited for a response he finally replied. “Not for the moment, ma’am.”

“Perhaps you, Mister Bonnet?”

“Perhaps later, ma’am.”

“In that case I suppose we should be getting along. If you would do the honors, Mister Bonnet.”

“Yes ma’am.”

“With authority, remember.”

“Yes ma’am.”

Henri looked at Bruce’s lily-white ass. It was hairless. Just a tidbit plumper and it could have passed for female. So you have a big cock. I’ll show you, you bastard.

His swishing of the cane caused Bruce to jolt a little but his cock with its blue ribbon jolted more-so.


Bruce’s eye open wide in amazement, as did his cock. Que pasa?

Lady Sheffield took a few cashews. The main event was on.


Bruce’s mouth opened wide in surprise as did his eyes. The blue tails of the ribbon tied to his upright cock jiggled. Bruce couldn’t believe the intensity of the pain. Perhaps he shouldn’t have accepted the invitation after all. But while he was dwelling on that:


Bruce’s hips jutted forward in absorbing the cut. With his legs spread his balls swayed as his cock and ribbon danced.


Charlotte took another sip of tea. Her hand went back to the bowl of nuts as she eyed Henri’s rock-hard cock with its jerking movements under the caning. It seemed that Henri wanted to smash poor Bruce with it as much as with the cane. The young man was really enjoying himself now after all that prior stress. So you have a big one; so what.


“Oh please. Not so hard. Mister Bonnet you really . . .”


“I’m sorry Bruce. What did you say,” inquired Henri.

“I said.”


Without taking her eyes off of Bruce Charlotte scooped up a few more cashews. Umm. Good, but a tad salty.



Bruce’s hands came flying down from behind his head and flew to his tortured ass. This caused his hips to thrust forward towards Lady Sheffield, as did his cock.

“BRUCE! Behave yourself. You are acting like a child. Now take your spanking like a man.”

Bruce looked down at the lady munching on her cashews through tearing eyes. His ass was ablaze from the eights cuts of the horrid cane.

“My Lord, you are crying. James.”

The butler came forth and wiped Bruce’s eyes with his hand towel.

“Mister Hathaway, your hands are not where they belong.”

With Bruce’s hands back in position behind his head Henri smashed him with the hardest stroke yet while James was still dabbing away his tears.


“There; there; Mister Hathaway. It’s merely a spanking, you know,” said the butler. “Do control yourself, sir.”

SWISH xslot Güncel Giriş THWICK!! SWISH THWICK!!


The butler turned to look at her ladyship to see her nod to the young man’s cock. There was pre-cum oozing out. So he switched from dabbing tears to dabbing pre-cum. Daintily, of course. And while showing respect.

While this was being done Henri turned to see the heads of the young servant lasses now sticking from under the chess tablecloth. They giggled when he gave them a thrust of his exposed cock. The butler motioned for them to hush.

“Let’s see the progress. Bruce, please turn around.”

Charlotte looked at the young man’s pale white skin against which the raw red tramline welts stood out so pronouncedly. How delicious. No wonder he had cried like a baby.

“Very nice. I must congratulate you.”

“Thank you ma’am,” replied Bruce.

“Not you, you fool. Mr. Bonnet; he has such a nice touch. Are you perhaps a golfer?”

“Thank you ma’am,” replied Henri. “I must admit that I rather enjoyed it. And yes; I do play a little golf.”

“No doubt, from the look of your manhood. Is that pre-cum that you too are now oozing? James.”

The butler returned and took a close look. Yes, there was a drop. So he reversed his towel’s sides and dabbed it away, respectfully, of course. In this manner Bruce’s pre-cum was on one side of the hand towel and Henri’s on the other.

“Will that be all,” asked James of his mistress.

“Of the cane? Oh I suppose so. Mister Bonnet has done such a splendid job, don’t you think?”

“Yes ma’am. He shows distinct promise.”

“Turn back around and face me, Mister Hathaway. And Mister Bonnet, if you would stand to his side.”

Charlotte looked at the two young men still wearing their white dickeys and black bow ties standing before her with their cocks amazingly still at attention. Only Bruce’s cock bore the blue ribbon. Charlotte was still amazed at the contrast between Henri’s average sized cock protruding from his black pubic hair and Bruce’s monster protruding from its sandy colored hair. That it matched the color of its owner’s head of hair and that Henri’s match the color of his black hair and black horn rim glasses, was most notable. Yes; most notable.

Even more odd what that each had a passive personality even though Henri had shown his lustful side.

“James, please refresh my tea and give our young contestants some.”

In no time at all Lady Sheffield was back to sipping more tea as she looked at the two men gingerly sipping theirs as they stood before her with their cocks still at attention as if in salute.

“Gentlemen, I have had quite enough of admiring your male organs in full heat. If you now would be so kind as to return them to their natural state.”

Henri smiled. He had had quite enough of seeing Bruce’s big cock with that damn ribbon which made him feel that his own was pathetic when in fact it was quite normal.

“Gentlemen; now enough. Please cease and desist from your presenting your cocks to me in this disgusting manner. I have had quite enough of this display. It is rather, after all, rather rude after I have asked you to cease and desist.”

Henri and Bruce exchanged glances as they continued to sip their tea. Just how should they do that?

“Well? Do I have to do it myself? Now stop this.”

That brought smiles to their faces.

“Gladys; Marie. Two icepacks, please.”

Suddenly the tea didn’t appeal. Icepacks? Perhaps for Bruce’s welted butt, but for their cocks?

Moments later James was there with his silver tray with two bluish tubes of packed ice. Gladys took one and slid it over Henri’s cock while Marie did the same to Bruce.

With their cocks sheathed in blue ice packs she found them now less offensive. Yes it was better now seeing them with their upright cocks sheathed in ice with only their cockheads protruding out one end. Nevertheless it was bazaar seeing them in that condition while still holding their tea cups and wearing their formal white dickeys.

The cold applied to their cocks began to make them tremble. In turn their teacups began to shake upon their saucers so that they now had to hold them in separate hands. They looked at Lady Sheffield with pleading eyes. Oh please; please.

Under these freezing conditions the blood had quickly drained out of the men’s sheathed cocks. As their cocks withered and retreated the frozen tubes of ice were lowered like the lowering of a flag.

Suddenly Henri’s icepack fell to the floor to reveal that his pecker had shriveled up like a turtle’s head retreating into its shell. But Bruce’s sheath remained on while pointing down.

Henri felt humiliated. It was as if he were cockless. His hands were trembling so much.

“More tea, sir,” inquired James with a slight smirk.

“That’s enough,” said Henri as he squatted down and laid his teacup and saucer down on the floor beside his ice sheath. As he began to weep he put his hands over his face.

Bruce looked down at the pathetic Henri and then at Lady Sheffield. As if needing to, he took both hands in sliding his ice sheath off his cock all the while smiling in triumph.

Charlotte herself smiled in contentment. There was one in total humiliation and the other with his ass totally thrashed.

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