To the Manor Bound Ch. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Stunned into silence Peter returned back up the spiralling staircase to his room, happy for the moment to be allowed out of the dripping wet bikini; anything would be more modest. Though the outfit he found waiting for him on the bed - again with a little note from Lord Madison, this time informing him that he was due to begin his secretarial training - would hardly be called modest in even the most debauched societies - using a modest amount of fabric perhaps but hardly creating a modest appearance.

Again, Peter examined himself in the mirror before leaving the room; biting his bottom lip and trying to reassure himself by telling himself that it would have made a perfectly good ladies business suit were the shirt not so tight that it was effectively impossible to do up the last two buttons and the skirt so short that his arse cheeks were near continually falling out.

As he re-opened the door to the central sitting room Peter found Lord Madison and Mr Tyler already seated in the same overstuffed leather chairs he had sat in that first evening of his sentence at Hambleton Manor.

"Ah Francine, so good of you to join us. Fetch us two large brandies, the Martell I think."

Outside the large bay windows the sun was just beginning to sink as Peter poured out two large tumblers full and then stood by patiently holding them on the tray, waiting for the two older men to take their drink, all the while his skirt riding further up.

Once the tray was emptied his Lordship motioned dismissively with his hand away from them and towards the table that he had arranged earlier, now completely set up for secretarial work with an old-fashioned ribbon typewriter and a swivelling office chair.

"Do try and keep up girl, and remember that I'm going to dock your pay for every typo that I find your bubble brain has made." Lord Madison spoke over his glass as Peter positioned himself ready to begin keeping minutes and then turned back to Mr Tyler, "It's the only way that you can break in a new girl . . . to a secretarial position at least."

Mr Tyler coughed, eager to begin, "If we could get down to business your Lordship, there's been talk that the commons are going to introduce new legislation

Peter started typing, moving his fingers uncertainly over the stiff keys of the typewriter. More used to the easy tap of a laptop keyboard it took him some time and patience before he was able to catch up with the conversation and when he did he was forced to almost immediately stop and look down at the seat of his chair; the quicker that he typed the more obvious it became that the steadily building buzz of a vibrator was throbbing through the chair and against his buttplug. From the corner of his eye Peter saw Lord Madison flash him a dirty grin and he realised that it was intended as a twisted incentive to keep up with their conversation.

Mr Tyler leant forward in his chair to speak, "To be perfectly frank with you, your Lordship, I'm starting to worry about this newly proposed bill: it's vague enough to get some cross-party support and you know that any kind of censorship will cripple my trade.

Lord Madison dismissed his concerns away with a wave of his hand, "My dear old boy you need not worry about it for a moment longer. The very second you've taken your seat in the lords the matter can be shuffled off to a secondary committee who can bury it so deep in the files of Whitehall that it won't see light again, let alone fresh ink."

Mr Tyler furrowed his brow a little, "I don't doubt that it will, but how can you be sure that you'll be able to get me a seat?"

"I've been about the place all my life and I've got dirt on half of them and know how to cater to the sexual peccadillos of the remaining half. I just need you to back up your side of the agreement."

"Well now you know I'm always happy to extend my little print, video and internet empire, but to be honest with you I just don't rightly know whether there's a market for it."

Lord Madison raised an eyebrow, "Has pornography ever not sold?"

"Hah!" Mr Tyler's jowels wobbled a little under his chin as he laughed, "Not in my forty odd years of experience."

Peter's hands froze for a second as he finally realised where he recognised Mr Tyler from: he was one of the largest pornographers in the country; indeed Peter had once attended a protest outside of his headquarters regarding the exploitation of his models. He was only brought back to his secretarial duties when the word tracker on the keyboard registered the pause, cut the vibrations, and sent a small, but significant, electric shock to his cage.

Lord Madison reclined in his chair once more and gestured with his hand over an antique map of the traditional counties of England, "I trust that you've seen sufficient proof of my influence over the past few days and your visit this afternoon; as far as I am concerned the only remaining question remaining is which county seat you would most prefer to be raised to."

As the attention of the two men was drawn to a wall-map of the ancient counties of England- and a few counties were dismissed out of hand due to their respective peers being close associates of Lord Madison - Peter slipped a new sheet of paper into the typewriter and continued his typing as seamlessly as he could manage:

"PLEASE HELP ME! I AM BEING KEPT HERE AGAINST MY WILL! LORD MADISON IS POWER-MAD! HE HAS TURNED ME INTO HIS SISSY MAID BY FORCE AND IS KEEPING ME HERE BY BLACKMAIL! I AM BEGGING YOU, PLEASE CALL THE POLICE!"

With their backs turned to him momentarily Peter quickly folded the paper and hid it neatly between his breasts, giving a little prayer that it wouldn't be the straw that broke the camel's back and caused another button to fly from his straining shirt.

"Well now, I've always taken a bit of a shine to Southmoltonshire, if you're sure that the seat would come with enough prestige to carry the vote."

"My dear old thing, all such noble ancient seats of England convey enough authority to cover any of your needs . . . but I can clearly see that you need further convincing. Francine, a moment outside."

Tottering back onto his heels Peter followed Lord Madison out of the door, feeling both the smooth silk of his panties and the lecherous eyes of Mr Tyler rubbing against his arse as he walked away. Out in the corridor Lord Madison leant close to him, pinning him to the wall.

"Clearly my guest requires a little further education - hardly surprising as I believe he attended a state school - in the finer points of aristocratic privilege. Privilege which I believe you are now in a suitably trained position to demonstrate."

By now, after five long hard weeks of training and gradually learning the mind of his Master, Peter instinctively knew what Lord Madison was suggesting. "But he- he mi-"

"Yes, yes, he might notice that your little clitty is a fraction bigger that most girls, but you have other 'assets' you can make fine use of in a situation like this." At that Lord Madison rested his hands over Peter's breasts and pushed him back against the wall, fondling them whilst looking into his eyes as he spoke slowly, "Do not let me down Francine."

Before Peter had a chance to object Lord Madison had spun him on his toes and pushed him back through the door to the sitting room. Suddenly presented with the rotund figure of Mr Tyler leaning against the mantelpiece Peter stuttered to a stop and unconsciously smoothed out where his dress-shirt had been ruffled.

"C-can I refresh y-your glass Sir?" Peter found himself deferring to the older man, mostly still out of sheer nerves at the risk of being discovered, and letting his eyes settle downcast as he asked.

"Much obliged my dear, another splash of that brandy." Mr Tyler held his glass close to his chest, thus forcing the young maid to draw up face-to-face with him and appreciate how diminutive his stature was in comparison to the wealthy industrialist.

After filling the glass back up with the same 1962 vintage that he had been served on his first night in the manor house - though, naturally, minus the chloral hydrate - Peter turned and saw the faint silhouette of Lord Madison waiting in the doorway, the remote control to his electric shock-collar swinging like a pendulum from one of his fingers: it was now or never for Peter.

Curtseying as he presented the refilled glass Peter simply allowed his knees to continue to fall until he was kneeling, prone, in front of Mr Tyler. Looking on with as much bemusement as arousal, Mr Tyler sipped on his brandy as he watched Peter begin to slowly unbutton his shirt and the cartoonishly huge breasts bursting free and rubbing against his leg.

"H-his Lordship h-has asked me to extend to you all the privileges of the estate during your time here." Peter's face burnt with humiliation as he leant forward to unbutton the trousers of his guest.

But he was stopped in his tracks by Mr Tyler laying a hand on the back of his head and tilting it upwards to look at him. "Not so fast young lady."

"B-b, I-, that is Lo-"

"Yes, yes, I know: your master has ordered this, but you see I work in a business where I'm constantly surrounded by beautiful women who all think that they can make it big just by sucking my cock, some of them just as pretty as you my dear. So you're going to have to do something pretty special if you want this, and I want to see just how eager you are to fulfil your Master's orders." He took another long slow sip from the tumbler before continuing, "Beg," He smiled, "Beg for it."

Biting his bottom lip Peter allowed his training to kick in as he swallowed yet another lump of his pride and tried not to let on how disgusted with himself he was. "Please? Please can I service your cock Sir?"

"What was that? I could barely hear you, I'm sure you can manage better than that lass."

"Please Sir, please let me worship your cock. I'm begging you, pleading you, let me prove how much I want to serve you by submitting myself to your cock." The words came from between Peter's lips in a flurry and he barely knew where they had come from.

Mr Tyler simply chuckled and slowly undid his flies, "Well alright then young lady, since you did ask so nicely I'm only too happy to oblige."

His already semi-hard cock flopped out from his trousers and, whilst neither as thick or as long as Lord Madison's, it was certainly bigger than Peter remembered his own cock being, and as this thought came to him he felt his tightly constrained penis involuntarily try to harden in its chastity cage.

Peter shuffled forward on his knees as he lifted his breasts up to engulf the bobbing, throbbing cock of Mr Tyler. As he started slowly stroking the cock he found that he was faced with an impossible choice between watching the thick, bulbous head bouncing nearer and nearer to his face or making eye-contact with the leering, sweaty Mr Tyler.

The hypnotic training he had undertaken kicked in with the efficiency of clockwork though, even without Peter realising it, and he made sure to make as much eye contact as he could stomach. What he found harder to stomach though were the lewd phrases he found himself spouting, though he managed to convince himself for the moment that he was simply trying to speed up the process.

He found himself moaning, "I can't wait for your cum in my mouth," and, "You're the biggest I've ever had!" This last moan was certainly untrue as Peter could still see Lord Madison standing in the doorway, his cock straining against his trousers.

Mr Tyler grunted and stuck a thick, sweaty finger into Peter's gaping mouth for him to suck on as he thrusted ever faster between Peter's breasts. Suddenly more embarrassed by this wantonly sluttish act Peter broke eye contact and looked down just in time to get a face full of cum as Mr Tyler shot load after load over his cheeks and tits and into his open mouth.

With both of the older men distracted Peter took the opportunity to slip the folded note into Mr Tyler's pocket. He had only just had enough time to remove his hand before Mr Tyler casually pushed him away onto his back on the floor and, taking out his wallet, casually peeled off a couple of twenty pound notes and dropped them down onto Peter.

It was only then, with money sticking onto his cum-drenched tits that Peter suddenly started to wonder about the exact nature of the new publications Lord Madison was talking about, and who would be starring in them . . .

He was only woken from this reverie by the sound outside the door of the two men shaking hands on their shady backroom contract of which he had been used as a mere sex-toy prop.

Nevertheless, after lapping up the cum from his body at the direction of His Lordship, Peter found that he was able to go through the rest of the evening with an additional amount of spring and verve in his step, excited at the thought that he would soon be able to get out even as Mr Tyler pulled off and left him alone with Lord Madison once more. He found himself acting like the perfect maid that Lord Madison was intending to turn him into - without a single worry in his mind at how naturally it was now all coming to him.

He continued dusting the library with limper wrists than ever before, he perfected the beef wellington that Lord Madison had ordered for his dinner, and he curtseyed demurely as his Lordship ordered him to his bedchambers for the night - expecting the ring of sirens at any moment.

Shutting the bedroom door behind him Peter closed his eyes and exhaled, allowing himself a fleeting moment of happy security; fleeting because when he opened his eyes he saw a third note pinned to his pillow in the same position as the ones pinned to the outfits he'd worn earlier. With a growing sense of dread and disbelief Peter picked up the note and immediately recognised his own handwriting and his own plaintive cries for help.

"Did you really think it would be so easy sissy?" Peter span on the toes of his stilettos, almost losing his balance in the process, to see his Lordship standing in the doorway, his arms cross and a familiar cane hanging from his fingertips. "Did you really think that I wouldn't notice your pathetic attempts to slip our visitor a note?"

Peter collapsed onto the edge of the bed, his knees shaking and his eyes falling down to Lord Madison's shoes.

"I think that one stroke per word should be sufficient punishment to teach you never to try a scheme like this again, sufficient for tonight at least. Which to my count makes it a nice round forty of the best across your bare little backside. Lie down on your front."

Peter tried shaking his head, tried putting up an objection; the familiar sight of the dangling cane and his Lordship's intimidating stature now all it took to make him cower.

"I've had enough playing for today Francine so I'm not even going to tell you a second time." And with that Lord Madison roughly grabbed one of Peter's ankles and secured it tightly to a bedpost, ignoring the pleas and flailing as he worked quickly and efficiently moving from one limb to the next. When Peter was finally completely secured spread-eagled and face down on the bed the micro-skirt had ridden up fully around his waist leaving only the pathetic little scrap of a g-string against his arse. Taking the silky material in one hand, his Lordship pulled hard giving Peter a humiliating wedgie until the fabric ripped away from his body.

After pausing to work the pre-cum stained panties into his servant's mouth Lord Madison raised the cane above his shoulder.

Schwip!

His Lordship was indeed done playing games with Peter as he forewent his standard routine of mocking and belittling his maid as he punished.

Schwip!

Instead he worked the thin cane with an almost animalistic vigour against Peter's bare skin, working up a sweat that broke through his dress shirt.

Schwip!

Peter thrashed and pulled at his bonds but all to no use as he couldn't even make the sturdy oak-frame bend, let alone free himself.

Schwip!

Eventually he buried his panty-stuffed mouth into his pillow and tried to count away the remaining strokes.

Schwip!

The moment the fortieth stroke fell his Lordship collapsed down on top of his young maid, biting down on his neck and ear as he groped at his raw arse-cheeks and growled in his ear, "Perhaps I ought to include you as part of the deal with Mr Tyler, see how you enjoy being bought and sold like a common whore."

He stood back up and straightened his tie once more as he listened to the panting gasps of his sissy, "I will say this much though, congratulations on reaching a level of femininity that you were able to successfully convince a complete stranger that you are a woman. Now all you need to do is learn to convince yourself and accept your new position. Think about how much more easily, and how much more enjoyable today would have been: you would simply have engaged in a little light housework, followed by some intellectual stimulation to keep your mind active, and then finished by having sex with one of the country's most eligible bachelors, if you would only convince yourself." His Lordship bent over and placed the cane sideways gently between Peter's lips. "I believe I shall leave you to consider that matter privately until the morning. Sleep well Francine."

And with that Lord Madison took his exit, not even bothering to close the door behind him. So that was how Peter spent the night: tied firmly to each corner of his bed with his legs wantonly splayed, the ripped fragments of his pre-cum stained panties resting under his nose, a tortuous cane gripped tightly between his teeth, and with his brightly-red burning arse openly on display.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
18 Comments
AnonymousAnonymousover 1 year ago

Please list as humiliation. Not a turn on. This is a great story for a book but it does not belong in erotica reading.

theresa628theresa628almost 3 years ago

Love this story. Can't wait for the next chapter. xxx

AnonymousAnonymousalmost 5 years ago
Wonderful

A really well written story that I have read a huge number of times. I beg that more in this vein be written.

dr_lungsdr_lungsover 5 years ago
loving the series

really great series. hope you write more at some point.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Trapped and Trained Ch. 01 Man is drugged, then dressed up and trained to be a slut.in Transgender & Crossdressers
Property of the Master Ch. 01 Caught in a girl's swimsuit and dominated.in Transgender & Crossdressers
Captured to be Sissy Slave Ch. 01 Man is captured to become sissy maid, fuck toy.in Transgender & Crossdressers
Lesser of Two Evils A man's choices will transform him into a cum slut.in Transgender & Crossdressers
Groomed to Depravity Ch. 01 A college boy's life goes awry on Halloween.in Transgender & Crossdressers
More Stories