Will remained on all fours, his tights sodden and uncomfortable. His arse empty at long last.
“So now it is time to deal out the punishment – and the reward!” declared Alexander.
“A reward?” Raymond repeated, his eyes widening.
“Oh yes. To have undergone such a trial and beaten your fellow slave so decisively deserves a reward, don’t you think, Yorick?”
The hose-maker barely had time to reply.
“And yet,” Alexander continued. “I have always prided myself on being a fair man, and it seems clear to me that this little slut here was forced to take far more food up his boy pussy than did the other one. I wonder if the contest was truly equal.”
“Your integrity does you credit, Master Alexander,” said Yorick, without a trace of irony.
In his exhausted and demoralised state, Will nevertheless experienced a flicker of hope. He watched Raymond’s face fall into stunned incredulity.
“Thank you, Yorick. Yes, the more I consider the matter, the more it seems to me that we should have a final round in our little contest. And I have an idea to determine which of these page boys will be declared the ultimate winner.”
Alexander glanced pointedly at both Will’s and Raymond’s bulging crotches.
“I suggest we milk them, Yorick. Thus shall we discover which of them possesses greater self-control. The one who cums first will be declared the loser and will be duly punished.”
“Superb! Simply superb!” Yorick was practically salivating in anticipation.
“And let us continue to allow chance to decide which of us will masturbate which slave…”
Alexander produced a coin. It whirled in the air before landing at his feet. “You will take the yellow bitch. And I shall yank this filthy little bird’s pathetic boycock.”
Raymond was clearly suppressing his indignation that victory in Alexander’s kinky game might yet be snatched from him, but he knew better than to challenge his master. Will dared to nurture a small piece of hope: could it be that, secretly, Alexander wanted him to win?
“Lie on your backs!” came the instruction.
Both boys did as they were bidden. Their naked torsos rested on the rugs, their stockinged legs bent so that the soles of their feet lay flat on the floor.
Alexander and Yorick knelt beside the two of them. Raymond groaned as a stomach cramp hit him. There was no longer any reason why Raymond should not empty his bowels of the fruit salad nestling within. But Will thought he knew enough of Raymond’s character by now to know that his pride and arrogance would mean he would not want to lie there and soil himself, especially not in front of Will. Will’s spirits rose yet further. His rival would therefore have to focus on keeping his arse clenched tight and fending off orgasm.
“Let us begin,” said Alexander, with a devilish smile playing around his lips.
He reached into Will’s sticky hose and grabbed the boy’s cock. It pulsed instantly, and Will immediately began to try and conjure the most unappealing images that he could. The fat, gap-toothed Mistress Olwen, old Dirk, the village bumpkin, cows, goats, pigs… anything that might cause his dick to soften.
But of course Alexander was having none of that, as he expertly tweaked and manipulated the lad’s thickening member.
“Does that feel good, boy?” he murmured. “You like the feeling of me rubbing that chocolate all over your sissy little prick?”
Will whimpered slightly.
“What a little slut you are, getting turned on like this. I’ve made you take a dump in your tights, and all that mess is still lying there. You filthy little bitch, humiliated in your own gunge. Do you know what a fucking disgusting state you look right now? Bits of banana clinging to your arse, your bumcheeks covered in melted chocolate. Marshmallows clogging up your hose. And your poor violated arse finally emptied. Maybe we should do something to rectify that…”
Will groaned as he felt his overused anus stretching once again, as Alexander started to pop the melting marshmallows back inside him.
“How do they taste I wonder?” he asked, as with one hand he continued to wank the boy’s rock hard dick, with the other he took a chocolatey marshmallow from the seat of his sopping tights and pushed it into Will’s mouth.
“Swallow it, bitch.”
Will gagged slightly as he did so at the thought of where the candy had so recently resided, but even that wasn’t enough to lessen the arousal at his groin. Alexander was simply too skilled at masturbation, he lamented.
“How is your bitch doing?” the Steward asked.
“He’s struggling a little but I think he’s enjoying it,” replied Yorick. “I hope he’s not enjoying it too much for his sake!”
Alexander turned his attention back to Will. “Are you getting close, boy? Remember, you need to stave off your orgasm or it will go hard for you…” He chuckled at his pun. “Maybe we need one of those big old plums to revisit its cosy former home. And let’s give you some potion first.”
Will had been dreading the potion. The damn stuff made him so horny, it would be ten times harder not to cum, he feared. And it had been a whole week since his masturbatory transgression in Yorick’s workshop. He was desperate to orgasm again. He just hoped that he could delay the moment longer than Raymond could.
The now familiar, heady aroma. The rush to his head, the slowing of his heart beat. That animal effect that just made him want to grind his crotch against something, to have his arse penetrated. He got his wish as he felt the thick roundness of the plum pushing against his hole. Not again, he thought. He couldn’t take that big fat fruit up his backside another time, surely…
“Up it goes, bitch… That plum’s going where the sun doesn’t shine. Shoved right up your horny little chute. Look at you in your mucky tights! Degraded. Humiliated. Excited. Me wanking off your chocolatey cock. And that plum deep up your boy butt…”
Will’s anus stretched, stretched, stretched - and in the plum went.
“Ugggggh!” he grunted, as the combination of the painful insertion, the effect of the potion and Alexander’s firm rubbing of his prick combined in one heady and fateful hit.
He tried to stop it but it was too late. The sensations had built and there was no going back. The only possible outcome was to release them.
“There we go, boy,” cooed Alexander as he milked his slave boy’s meat. Thick white cum spewed into the boy’s tights, mixing and mingling with the melted chocolate fondant.
“Ah – ah – ah…” the lad gasped as Alexander continued to yank expertly at his throbbing organ.
With his other hand, Alexander freed his own massive member and ejaculated silently over Will’s crotch: both man and boy’s cum mingling in a steaming pool of white liquid. Alexander let out a shuddering breath. He looked over to see Yorick successfully wanking off his charge, and Raymond filling his yellow tights with cum, as the melted mush of the banana slid out of his bum and into the seat of his hose.
Alexander wiped his hands clean on Will’s smooth and sweaty chest. “Oh dear, oh dear, oh dear,” he muttered. “If only you could have held out for a few moments’ longer. But it was not to be. I gave you a second chance, bitch, and you blew it. Now you’re going to have to suffer the consequences…”
“Such is your peasant depravity, I can see that nothing less than my personal attention will be sufficient to discipline you. We shall begin a weekly training session in the castle dungeons where I shall oversee your progress.”
Will nodded miserably, well able to imagine how Alexander’s training programme would pan out.
“As for you, young Raymond. I have a great honour to bestow to you. Clearly you have great things ahead of you, and it seems only right that you should begin a career path that, if you are hard-working and fortunate, may see you achieve the post of Chief Steward yourself one day.”
Will smarted to see Raymond’s smug sneer. He truly did look like the cat that got the cream, lapping up Alexander’s praise greedily.
“With this in mind, I am promoting you to a more senior position. As of this evening, you will serve as the personal steward of Sir Wilfrid.”
The effect on the dark-haired youth was instantaneous. His eyes widened and his mouth dropped open, stunned. Yet it was very clear that this was not a happy or a welcome surprise.
“Oh, Sir,” Raymond gibbered. “Please, no, please not Sir Wilfrid. I’ll do anything” –
“Hush, hush, now,” said Alexander. “I want no false modesty. You may feel that you are not personally worthy to wait on his illustrious personage, but I have every confidence that he will find you most satisfactory.”
“Please, Sir. I’ll scrub pots, I’ll clean out the stables” –
But once again Alexander interrupted him. “No more of this now. Yorick will you take young Raymond away, clean him up, and dress him in a uniform befitting his new elevated station. Particoloured hose perhaps? I believe Sir Wilfrid is very fond of purple.”
Raymond bit his lip, but nevertheless a big tear welled up in his eye and rolled down his smooth cheek.
“And you have no need to thank me, young man,” said Alexander blithely. “Your obvious strong emotion speaks volumes. Off you go, now. And good luck in your new role.”
Yorick grabbed Raymond by the arms and practically had to carry the distressed youth from the room. Will heard his fellow page’s pleas echoing and fading into the distance.
Alexander turned to regard Will, the faintest twinkle in his eye. “Are you still here, bitch? I suggest you go and get yourself and your tights cleaned up. I expect them to look as good as new when I see you serve Lord Geoffrey at dinner tomorrow…”
Will had staggered back to his bed in the dormitory via the well in the courtyard. He had encountered some sniggers and amused looks from various servants as he went, to see him dishevelled and smeared in sugary food. Then again, thought Will miserably to himself, the sight of him humiliated in some way was becoming an all too common occurrence in the castle.
He awoke exhausted the following morning strangely exhilarated. Whether by accident or design, Alexander had neglected to plug his arse again at the end of their lengthy session, so for the first time in many weeks he was able to move around without that ever-present reminder of his lowly position shifting around inside his butt. He pulled on his tights, still damp from having been washed and wrung out the previous night.
Then he looked across to the other side of the cellar, where Raymond’s bed lay – clearly Raymond’s exalted new position also came with different sleeping arrangements. He celebrated silently the fact that the vindictive older boy would no longer be watching over his every move. Still, he was intrigued as to what Raymond’s duties would be in serving the mysterious Sir Wilfrid – a name Will had not even heard mentioned in all his time in the castle – and why he was so reluctant to fulfil them.
His day passed reasonably uneventfully – which for Will was a relief these days. And at dinner, without the sullen watchfulness of Raymond ready to criticise his every move, he performed confidently and made no mistakes.
As was his habit, the sophisticated Lord Geoffrey made the most of fondling Will’s bottom through his tights as Will served the dessert tray.
“I see you have dispensed with this page boy’s plug, then, Alexander,” he observed blandly. “I think that’s rather a pity. Such a beautiful arse should be full.”
Alexander nodded. “I agree, my Lord. But it is my experience that if a boy is kept plugged permanently, the arse muscles become loose, which prevents a man taking his full pleasure. Also, the danger is the boy loses control of his sphincter. I’m sure my Lordship would not wish to see the lad soil his tights.”
He looked at Will pointedly given their adventures of the previous evening. Will blushed and looked down at the flagstone floor.
Geoffrey slipped his hand down the back of Will’s tights, and inserted a couple of fingers into his arse. Will flinched.
“I see your point, Alexander, but it seems to me this lad’s hole remains as tight as a young girl’s – in spite of the attention it has received. Still, you know best in household affairs, I suppose.”
“Thank you, my Lord. Now, what will you take for your pudding? I can recommend the plums most highly...”
That evening, Will was surprised to see that a newcomer to the dormitory was occupying Raymond’s old corner of the cellar. It was a young man, perhaps twenty. He was tall and slender, and his green waistcoat and particoloured green and brown hose hung slightly off him, as if he had lost weight since the time he had been fitted for it. Will was surprised to find himself experiencing a certain level of distaste at the fact that the tights were not figure-hugging as was usually demanded. Alexander’s regime was clearly having an effect on him!
The newcomer’s hair was sandy coloured and he had large soulful grey eyes and a pretty, almost feminine face. The most noticeable thing, however, about him was his pale pallor and the dark circles around his eyes. He stooped slightly, and looked as if he had suffered some kind of recent trauma.
Mortimer, the chirpy red-haired lad who slept in the bed next to Will noticed him observing the newcomer.
“His name’s Bernard,” he informed Will, solemnly. “He’s the page that Raymond has replaced.”
“Ah,” whispered Will. “So he used to work for Sir Wilfrid then?”
“That’s right,” nodded Mortimer, pulling off his orange hose and slipping under the blanket of his bed.
“Who on earth is Sir Wilfrid?”
“Don’t you know?”
Will shook his head.
“Well, I suppose you haven’t been here long, after all. He’s the old uncle of Lord Geoffrey. Hardly anyone’s seen him for years. He lives in the squat tower and hasn’t left it for as long as anyone can remember. He’s supposed to be about a hundred years old. He can barely walk and he’s half-senile. Only one page is assigned to wait on him and satisfy his every whim. Every couple of years or so, the page is replaced. They say that even the strongest lad can only last that long.”
“Why?” asked Will. “What happens to them? What do they have to do?”
“Who knows? They all come back here looking like Bernard over there, shadows of their former selves.”
“So it was him who used to stand at the window of the tower and watch me when I was being given my purge.”
“I imagine so. Probably wanted to share in castle life in some small way. Maybe he even fancies you,” Mortimer smirked. “Although given the alternative he had on offer I shouldn’t say that was very surprising.”
Will chose to ignore that remark. “Will he be alright?”
“I’ve no idea. Sometimes they recover. Sometimes they don’t. But I’ve never yet heard of a page who wanted to talk about what happened to them whilst they were working for Sir Wilfrid…”
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