Life's Little Dilemmas Chapter 3 Plus Illustration

 

Below is Chapter 3 of Life’s Little Dilemmas. As we all know life can be difficult at the best of times but Covid has really put the tin hat on it for most and after almost a year of lockdowns of one sort or another, foundations are being stress tested and cracks are beginning to appear. Hopefully these vaccines whenever we get them  will work and we may return to something approaching normalcy – whatever that means. Right now I’d settle for having a quiet beer in a bar.

It’s been over 3 months since the last chapter –apologies that’s far too long but hopefully St Jude’s amused you in the intervening period.  I’ve been having difficulty in concentrating even though a big chunk of this was written in Nov, so thank you for your patience.

The gist of the story so far is covered a few paragraphs in so you won’t have to reread the last chapter but I omitted the part where our hero (because he needed money) has developed breasts from a drug trial. It finished with an unexpected knock on the front door with William dressed s a maid in the hallway.  

My thanks and gratitude as always to those who were supportive enough to tick the ‘more’ box and especially those who left a comment –believe me,it means a lot to know people actually like the material I post. Hopefully you will enjoy this piece also.

Take care of yourselves, family and friends

Carrie

PS I know I said I'd change the illustration at the top before Christmas but events overtook me it will be done in the next day or two.

Life’s Little Dilemmas

Chapter 3

By

CarrieP

 

When ideas are confronted with reality there will always be surprises.

 

S

urprises can be pleasant or nasty, fortuitous or unfavourable, disconcerting or comforting but by their nature they usually arrive when one least expects them. As a rule I am not enthusiastic at the idea of being taken by surprise but of course like every rule there are exceptions.

 By far the most surprising of several surprises, a clumsy phrase I know but accurate nonetheless, involved my recent encounter with a young man whereby a sequence of events was put in train that resolved my current servant problem, namely the recruitment of a new housemaid. The initial surprise was that the young man, William, actually applied for the position obviously in the full knowledge that such a post is by definition exclusively occupied by a female. Equally surprising was that I not only agreed to this strange arrangement but actively encouraged it. Bizarre as this may seem once I had given it some consideration I thought it a splendid idea after all how many women could say they had transformed a male into a female and even better a servant girl at that? Of course there have been many situations both in business and socially where some women myself included have held sway over males, usually officious, opinionated dreadful men who quickly come to regret their impertinence,

However never have I contemplated feminising one. Until now that is.

Ah yes, life really is full of surprises but I digress and will bring you up to date on just how the story unfolded.

In the hallway of my home I had now standing in front of me my new domestic- William- dressed in the smart and traditional morning uniform of a housemaid. A grey dress over which was a very prim and formal starched white linen apron, the straps of which went over his shoulders and were tied in a large bow, a frilled cap completed the ensemble. His face naturally delicate was made prettier by his light make-up which I had applied earlier. Make-up is usually discouraged in servant girls but I felt it necessary in this case and it did indeed lend him a surprising degree of femininity. Despite displaying a mixture of attractiveness and timidity, which I find adorable, he somehow also managed to convey a sense of shame which given his circumstances I suppose was only to be expected. After all a male in a dress could not legitimately be called a man and if exposed would undoubtedly be subjected to mockery and laughter. Being dressed as a housemaid would only add an extra layer of derision and ridicule however I suppose that really is none of my concern. I also suspect a contributing factor to his downcast countenance was the tight and restrictive high-waisted girdle that I had insisted he wear. A necessary requirement as such a formidable garment will not only give him a womanly shape but it will have the added benefit of  as allowing him to experience what we women must endure on a daily basis.

  I had hoped that I would have had at least a few hours to tutor him in the fundamentals of femininity but an unexpected caller at the front door made this impossible. Inspecting the well groomed and conventionally attired maid in front of me I attempted to be as objective as possible in determining whether there was sufficient femininity about his appearance to succeed in this subterfuge. The face was more charming than beautiful and his figure as a result of his new corsetry did give him a waist and provided him with vaguely girlish hips. The girdle was long enough to restrict his gait so unless he told this visitor he was a young man I felt reasonably confident my unannounced guest would not immediately guess my maid was male. Another clearly irritated knock on the door focused my mind and making a slight adjustment to his cap I assured him he would pass muster and gestured to him to open the door and ensure he curtsied. After a little indecision on his part which unfortunately necessitated the threat of a cane to that back of his legs secured his obedience and he moved quickly to the door. He tried one last pleading glance at me but I remained resolute and he eventually succumbed to the inevitable and opened the door.

“And about time.” the clearly exasperated and elegantly attired figure snapped announcing the arrival of Eleanor Forsythe, one of my closest friends. As she brushed past in a whirl of expensive perfume and even more expensive fur my new maid who was so taken aback by her entrance stood open mouthed and forgetting to curtsy.

“Eleanor.” I greeted her a tad nervously “Such a pleasant surprise. I wasn’t expecting you until next week.”

“Oh you know me Felicia darling, the country bores me after a few days.” she said, kissing me on both cheeks and embracing me so tightly our breasts nuzzled together in a most pleasant squeeze. The sensation was not lost on Eleanor and she couldn’t resist kissing me lightly on the lips and added with her usual mischievous smile “I felt the need for a little excitement. Chasing after a fox all over the countryside for hours on one of my aunt’s ghastly horses can become tiresome quite quickly.”

Suddenly becoming aware of a third party she turned her full attention to the obviously anxious maid.

“You never told me you engaged a new girl, darling.” she directed her comment to me but her grey eyes lingered on William making no pretence of examining him head to toe.

Her inspection lasted merely seconds but I could clearly see from the poor lad’s face it seemed like hours.

“A pretty little thing.” she finally delivered her verdict in a breezy tone and as was her wont however her gaze continued to loiter on the girlish outline achieved by his girdle and brassiere and with a gleam in her eye she smiled at William and added “An improvement on your last girl, what was her name…”

“Sarah.” I reminded her.

“Ah yes, Sarah.” Eleanor said adding in her usual nonchalant manner “Although she did have a nice bosom.”

William began anxiously fingering the skirt of his uniform in a manner that did not go unnoticed.

“Oh not that yours isn’t…ah…”she laughed lightly searching for an appropriate word as her extended fingers grazed gently across his slightly protruding girlish breasts before eventually settling on the most appropriate word she could think of “…agreeable.”

The facial expressions on my new maid’s face appeared to fluctuate between panic at Eleanor’s increasing scrutiny and embarrassment at her backhanded compliments regarding his figure and attractiveness. She has always enjoyed teasing new servants but for a moment I thought the unfortunate young man was going to faint.

“When you’ve quite finished with your appraisal of my new housemaid,” I intervened a little testily before William succumbed to a fit of the vapours “perhaps you would join me in the drawing room.”

“Don’t worry darling.” she answered me although her eyes were still fixed on William as she slipped off her coat and handed it to him “ As you are aware I need a second maid but I promise I won’t steal her away from you. Unless of course she wants to leave, do you my girl?”

I thought I saw his legs wobble slightly as he took her coat, his eyes pleading for an intervention.

“Enough Eleanor!” I responded, again a little sharply and trying to distract her  slipped my arm into hers and moved her towards the drawing room door “Now come tell me all about your dreadful sojourn to the countryside and that poor horse that had the misfortune to have you riding him.”

“It was a gelding.” she snorted and over her shoulder I could see William pale slightly as she continued with a rather coarse laugh “The only type of male I would associate with.”

As we turned towards the drawing room I glanced  back at the clearly perturbed statue like figure holding Eleanor’s coat, I instructed him as much with my facial expression  as with my voice “After you hang up Miss Forsythe’s coat proceed to the kitchen and I’ll ring the bell  when I need you.”

Settling myself on the sofa I could not but help noticing the way Eleanor gingerly lowered herself next to me.

“Breaking in my new corselette.” she explained with a mournful sigh and a resigned look as she adjusted the hem of her skirt over her knee before complaining rhetorically “Why ever do we put up with these ghastly foundations?”

 “Oh I think we both know the answer to that question?” I replied patting her on the knee.

“Vanity, yes I know, and I suppose the discomfort is worth it...” she laughed “But it is so annoyingly tight.”

“They always are at first, we all know that.” I smiled empathically “But just look what it has done for your figure, you look absolutely wonderful.”

“Yes I suppose the end does justify the means.” she replied and in the way women do when alone with each other she slipped her hand briefly inside her blouse and tugged gently at the cups of her corselette to adjust them to her satisfaction before continuing “A little nuisance is worth enduring to be able to fit into this skirt. And speaking of discomfort, your new maid looks a little anguished. She’s a peculiar thing, pretty enough in an odd way I suppose but a little ungainly, almost as if she’s uneasy in her own skin.”

“Oh she’s new to domestic service.”  I said truthfully “And you know how it is with girls that enter service late they find it difficult to adjust to their new lives. After a week’s training he will be as proficient as any of Mother’s housemaids.”

“He?” Eleanor laughed, immediately pouncing on my momentary lapse “The girl may not be a beauty, perhaps does look a little boyish and is no doubt somewhat gauche but describing her as a ‘he’ is a little harsh, darling, don’t you think?”

“A slip of the tongue.” I corrected myself. “I had a brief encounter with a young man earlier and it must have distracted me.

“Yes, given how irritating and imbecilic they are I suppose I can understand how a brush that ghastly sex would be a little disconcerting.” she replied to my relief “Although I do remember some years ago your mother telling me about when she was at her finishing school the headmistress accepted a number of males. It appears they were the unruly and rebellious sons of mothers who wished to have their behaviour modified and act in a more obedient and deferential manner to ladies in general and their mothers in particular.”

“Yes now that you mention it I do seem to recall her telling me a similar tale.” I answered hoping she would not continue this story further.

Of course I was only too well aware that Mother was very fond of recounting tales from this period of her life to her inner circle of friends which Eleanor and her own mother had been a part of for as long as I remember. Luckily her new corselette was a more pressing issue.

With a vaguely pained expression she rose from the sofa and moved to the fireplace ostensibly to check her hair and make-up but I strongly suspect it had more to do with the discomforting tight embrace of her new foundation wear. Although she would never admit it, Eleanor can be a little vain and I suspect she deliberately chose a corselette at least a size too small. As we all know corsetry although necessary can be quite uncomfortable at the best of times and on occasion I too have resorted to such measures so naturally I can empathise with the hardship she was undergoing.

“Some tea I think.” she decided unilaterally, a little to my irritation but as always I disguised it reasonably well  and before I could stop her she had pulled the cord for the servants’ bell, adding a little sarcastically as she refreshed her lipstick “I hope your new girl has enough wit about her to manage such a simple task.”

I had hoped Eleanor’s visit would be very brief and her encounter with my new maid would be her only one for at least a week until I had a reasonable amount of time to train him properly but her insistence on taking tea put paid to that particular plan. My hope was he would have composed himself a little prior to hearing the servants’ bell and taken confidence in the fact that this visitor had not detected his, or should I say our, secret. As he was expecting me to summon him at some stage he should not be too surprised when the bell did eventually ring.  I expected he understood that if he did not make an appearance I would have to explain to my guest why my maid did not answer her bell. Although this was such an unusual situation I could not be sure of how he would react.

Patience is not one of Eleanor’s strong suits and within thirty seconds she was on the verge of ringing the bell a second time, I tried to distract her with a little gossip about mutual friends which thankfully worked. Luckily a few moments later a timid knock at the door announced the maid’s arrival and an alarmed face peered around the door. I breathed a sigh of relief  but it was another second or two before the rest of the body reluctantly emerged as if propelled by some invisible force prodding it.

Under Eleanor’s somewhat irritated gaze the figure nervously made its way in what could only be kindly described as an awkward, ponderous motion to where I sat. It was a little like watching a newborn foal take its first unsteady steps.

“You rang Madam.” William said meekly, thankfully remembering mistress- maid etiquette. His eyes clearly conveying his deep anxiety he suddenly recognised the signal my raised eyebrows transmitted and he curtsied.

“It certainly took you long enough girl.” Eleanor said in a sharp tone. “And straighten up for heaven’s sake you’re walking like a bricklayer.”

Being only too well aware that the poor boy’s state of mind was quite fragile and he was still coming to terms with his new circumstances, I was concerned that Eleanor’s rebuke may be just enough to induce sudden panic and a subsequent escape. His face once again relayed his mounting fear and I was quite concerned my plans for him could easily be derailed at this early stage by Eleanor’s brusque manner. I had to act and decided reassurance and a kind word would be the best course of action.

“Eleanor!” I was forced once more to admonish her and for William’s benefit in a tone that left little doubt as to the vexation I felt at her criticism of my servant. “The girl is new to domestic service please try to be a little more tolerant.”

“Oh Felicia darling, you are far too protective of your girls.” she retorted, a little peeved by my intervention on William’s behalf but after seeing the frightened doe-like expression on his face her voice softened and she conceded “But I suppose I am a little a little tense.”

“Time of the month?” I said.

She nodded her confirmation and forced a smile as she took a step closer to him,

“Just for these few days every month I wish I was a male. They get away with so much.” she lamented like many of us  do at this time  before turning to the uniformed figure and by way of explanation or perhaps even a half hearted apology added with a sardonic smile, ”I suppose we all get a little grumpy at this ghastly time. Even servant girls, I imagine. Isn’t that so, my girl?”

I didn’t know which was more amusing, Eleanor reflecting on her menstrual cycle to what she considered a mere housemaid or the consternation William was experiencing ,his face growing paler as he tried to formulate a response. His eyes caught mine and I nodded discretely.

“Ah… umm…y…yes… Miss.” he eventually managed to scramble a reply and curtsied in what I can only presume was an attempt to both ingratiate himself with my guest and to convince her of his newly assumed sex.

His pallor did not go unnoticed by Eleanor either.

“Of course … I understand.” she said in an almost conspiratorial tone and her voice dropped and became more sympathetic “We are both close to having our little visitor I suspect. Have you started yet?

“Ah…emm…ah…I…” he spluttered his face becoming paler.

“No need to be embarrassed my girl.” she continued as I lurched between suppressing laughterand praying he would not faint. Eleanor, reaching into her purse retrieved a small, but to any woman, unmistakeable item and handed it to him. “Try this, one of my friends came up with this idea, it does not need a belt or safety pins to hold in place. I’m not sure they will take off so to speak but I do find them extremely good and very absorbent. You can put it on whilst you’re preparing the tea. They are a little too bulky but simple to use and perhaps a little awkward to fit first time.”

William just stood there, speechless and rooted to the spot, his expression oscillating somewhere between disbelief and mild trauma. I heard a slight, barely audible whimper which Eleanor thankfully seemed to miss and knew I had to intervene. However she did note his bewildered and dazed look and laughed,

“Maybe I should fix it in place for you.”

I thought I saw his knees wobble.

“Have you lost your tongue, William?” I said tersely without thinking and before I had time to correct the lapse Eleanor pounced.

“William!” she repeated in a tone I knew was bordering on the suspicious and which she immediately confirmed in the manner her eyes were drawn to the maid.

“Silly me, I meant Wilhelmina, of course” I replied immediately “The young man I encountered earlier must still be on my mind.”

The look on Eleanor’s face grew even more quizzical, while William’s took on one of rising alarm.

“Run along Wilhelmina.” I delivered he order with a little too much haste and a wave of my hand but panic seemed to prevent any movement as he remained motionless still clutching the sanitary pad Eleanor had given him.  In a slightly louder voice and accompanied by unmistakable facial signals I added “And don’t forget utilise the little…ahem… gift Miss Forsythe has given you.”

The tone of my voice appeared to rouse him although he did look quite befuddled and turning to leave he stopped almost as if some bell inside his head rang out a reminder he suddenly and rather clumsily swung around and bobbed a curtsy before quickly darting for the safety of the door. From the expression on Eleanor’s face as her eyes followed him I sensed that there would be some awkward questions. The thought crossed my mind that he may decide to attempt an escape but dismissed this immediately as a vision sprang into mind’s eye of his hand reaching for the front door only for him to realise he was wearing a maid’s uniform.

No, I thought, as I smoothed my skirt to await Eleanor’s interrogation. Although he may have considered fleeing he is now safely in the kitchen desperately trying to compose himself. I suspect once he has done so Eleanor’s high-handed manner will compel him to somehow comply with her suggestion and fit the sanitary pad into his girdle.

I had to suppress my laughter at the thought of him trying to fix such an article into his new foundation wear. Not the most dignified of undertakings at the best of times.

Will he adhere to her instructions? I wondered silently.

“Well, I must say Felicia.” Eleanor began returning her attention to me as the door closed behind the departing maid, “A most baffling state of affairs, what on earth is going on?”

“Whatever do you mean, darling?” I replied nonchalantly as I could and picking up the latest edition of Vogue I casually leafed through it.

“Don’t be coy.” she continued, her voice now taking on an almost inquisitorial tone. “Your new girl?”

“What about her?” I replied my eyes still on the magazine but Eleanor, as usual, is not easily put off. I cursed myself for my incredibly stupid lack of awareness.

“Well for one thing, she is the one of the most ungainly girls I have ever encountered including those dreadful hockey girls we knew at school. In fact she makes them look like Bolshoi ballerinas” she said, her beautiful large eyes searching mine for clues. “For another, she didn’t appear to know what a sanitary pad was.”

“Emm… I…”I faltered momentarily allowing her to raise my faux pas once more. “Well you said it was a new type, it probably confused her.”

“Mmm…” she didn’t sound convinced, before throwing down another challenge “And addressing her as… William?”

“A mere slip of the tongue. That’s all.” I answered as casually as I could and tried to deflect adding in an indifferent tone “By the way, have you seen the Spring Collection from Paris? Dior and Balmain have some wonderful creations.”

“Oh for heaven’s sake Felicia, what on earth is going on?” Eleanor retorted evidently quite sceptical by my response and ignoring my attempt at diversion. Suddenly and to my horror I noticed her eyes drawn to one of the chairs close to the large bay window and cursed myself once more as she stood and moved across the room.

“And what have we here?” she declared holding up the coat I had told William to remove but had forgotten he had left it on the chair. Fixing me with those grey eyes of hers she snorted sarcastically, “I suppose there is a plausible explanation for a man’s coat and hat residing in your drawing room.”

Before I could even begin to concoct some vaguely credible excuse she immediately swooped on my hesitancy and sniggered,

“And I would love to hear it, darling.”

A moment or two passed as I thought about fabricating some story about the coat’s owner helping me to repair something or other, or perhaps assisting me with some heavy parcels but I knew Eleanor would wish to see evidence of such an enterprise.

Felicia darling,” Eleanor didn’t wait for my reply, not that I had anything remotely resembling a plausible explanation “As I have already asked, what on earth is going on?”

                                          ************************

Stepping into the hallway from the drawing room William could feel a weakness at his knees and his heart thumping in his chest, after closing the door behind him he felt a little light headed. Nevertheless despite this anxiety he instinctively knew he should remain still and attempt to gather his thoughts. His first reaction was to turn towards the front door and flee however the reflection in the large mirror opposite quickly dissuaded him of the idea. He instantly understood that the primly uniformed housemaid looking back at him would not only look distinctly out of place in a busy city street but would surely attract the unwanted attention of passers-by. Visions of people pointing and laughing at him flashed into his brain, he knew it would not take long for his true sex to be discovered and the undoubted subsequent involvement of the police. He could be arrested and brought to court, perhaps even a prison sentence, the prospect was frightening. Even if he escaped prison the ensuing publicity would render hopeless any prospect of returning to some form meaningful employment. How could he hope to recover from such a scandal? His life would be ruined.

He was trapped.

Slowly the oxygen began returning to his brain, realising escape was out of the question and hiding in his room was not an option as it would only exacerbate his problems he swallowed hard and he began to move down the spacious tiled hallway toward the kitchen. The unfamiliar brushing of the satin slip he now wore against the equally peculiar sensation of his silk stockined thighs immediately struck him of just how ensnared he now was. He tried to avoid glancing at yet another mirror as he approached the entrance to the kitchen but the ghastly fascination was too much and catching his reflection he gasped. And although horrified at the image he nevertheless had to admit, albeit grudgingly, that at first glance he appeared more female than male

Although not the first time he had seen his new and altered appearance he remained nonetheless bewildered, unable to decide whether to be relieved at not immediately betraying his true sex or disgusted at the feminine figure he now resembled.  His eyes were drawn to the breasts he had previously kept tightly and secretly bound, they now stood proud supported by Miss Goodbody’s brassiere, his girdled waist exaggerated his hips giving him a slight yet distinctive girlish shape. Finally dragging his eyes from the mirror he entered the kitchen and suddenly realising he was holding a soft length of cotton padded material his eyes widened in horror. The recognition of what the item represented and what was expected of him left him close to tears.

“Surely Miss Forsythe would never check whether I actually…”he murmured out loud, unable to bring himself to complete the sentence.

Perhaps…, a measured voice answered from the fog of confusion inside his head, but have we not witnessed the type of woman she is? Could we really put it past her? Such an authoritative presence, the kind of woman who demands her every instruction is carried out to the letter.

“But…”the empty room echoed to his forlorn voice as he stared at the uniquely feminine article “this!”

She views us as female and believes she is being helpful and kind. What happens if she insists on checking?

“Surely…she would never…”he blurted

But what if she does? the voice quickly and forcefully interrupted Everything will be ruined, we will be exposed, lose everything, the salary, the accommodation, the possibility of a position with the Marchioness of Dunraven.

The young man remained silent, desperately trying to formulate a reasonable response but could not. All that he had heard was true. Being dressed as a girl, employed as a housemaid and required to wear such a humiliating uniform was deeply and excruciatingly shameful but the alternative was penury and a dreadfully uncertain future. Still, the question loomed large. Could the lure of a salary beyond his wildest expectations and lavish lodgings justify such an ignoble and cowardly desertion of his masculinity?

You know quite well what awaits us if don’t comply, the voice whispered gravely. Do it now before Miss Goodbody rings for tea. Otherwise…

In a trance like state he lifted the uniform’s heavy lined skirt and starched apron and underneath his satin slip his hands fumbled for the top of the tight girdle which he managed with the greatest difficulty to tug down. With fumbling and shaking hands not to mention having no idea where to position the article he eventually managed to settle the pad into the only place he could think of- the girdle’s gusset.

Probably better if our member is tucked back tightly between the legs, the voice helpfully suggested, it will ensure there is no unsightly bulge just in case Miss Forsythe actually checks. I believe girls are quite sleek in this area, it would not do to have a protrusion no matter how small in such a place.

So immersed in this delicate operation he complied without hesitation and after fixing the pad as best he could he manfully drew the girdle up his torso, whimpering quietly as it compressed his middle once more in its nylon and satin grip.

His hand passed over the front of the girdle and he almost gasped out loud as he failed to find any hint of his sexual organ. It helped of course that his anxiety had helped to minimise the offending organ.A quick glance confirmed the satin material contained no evidence of masculinity whatsoever.

No time to admire ourselves, he was told, now fix our slip in place and make sure the skirt and apron fall correctly. The last thing we want is to embarrass Miss Goodbody in front of her guest.

Dejected by the notion, that now even underneath his feminine clothing, there was no trace of his masculinity he nevertheless managed to shake this despondency and turned his attention to the task at hand. Satisfied his manhood was adequately concealed he adjusted his slip and skirt, he sighed and suddenly became aware of his surroundings and the reason he was there in the first place. He quickly crossed the kitchen floor and commenced to assemble the various items for the ladies’ refreshments. As he began to move about he immediately felt the strange and bulky presence between his legs and for a minute or two had to adjust his gait ever so slightly to accommodate the cumbersome item lodged in such a sensitive area. He tried to rid his mind of the humiliating position he found himself in but the alien object between his legs together with the unfamiliar feeling of air circulating around his lower limbs made this impossible.

It was becoming evident to him that his outward conversion to a female was accompanied by a similar transformation underneath his maid’s formal uniform, the strain of elastic against his skin and the gentle brush of his satin slip on the silk stockings attached to his tight garters were a constant reminder that he no longer resembled a member of the male sex. The constant clicking of heels echoing on the hard tiled floor merely reinforced this new shameful reality.

He tried to distract himself from his humiliating situation by busying himself with the chore to which he had been assigned but the peculiar feelings he was experiencing made this very difficult. The sudden jangling of the old fashioned servants’ bell startled him and he immediately banished these new physical sensations to the back of his mind. He knew he would be expected to appear in the drawing room within minutes. His hand trembled slightly as he poured the hot water into the teapot and had to compose himself before he lifted the tray.

Deep breaths, the voice quietly assured him. Don’t worry, you look every inch a servant girl. Keep your back straight and take short steps. Just remember you are dressed like a housemaid, now act like one.

 

                                               ************************

 

Hearing the soft knock on the door I reluctantly drew my lips away from Eleanor’s and feeling her hand gently squeeze my left breast I smiled and kissed her once more before reluctantly stepping away.  Taking a few moments to compose myself I adjusted my blouse and straightened my skirt before moving to the mirror over the fireplace where  I checked my appearance, freshened my lipstick and repositioned a few stray strands of hair.

“That colour really does suit you darling.” Eleanor said as she joined me and puckering her lips performed a similar action adding slyly, “I notice our new little servant girl is wearing the same colour. I wonder what else she’s wearing has a similar colour.”

“Eleanor!” I feigned mild offence at the remark as I fixed my jewelled barrette in place and catching her face in the mirror continued “Please behave. I don’t want to lose another maid so soon.”

I imagined the slight delay in answering the poor boy’s timid knock only increased his anxiety and finally satisfied I was presentable I issued the instruction.

“Enter.” I said in a clear commanding voice.

Eleanor and I monitored the progress of my new maid crossing the drawing room floor, his face fixed in concentration as he moved slowly and  to my surprise remarkably gracefully to where we now sat by the large bay window.  I was pleased to note that he had used the willow patterned china and had arranged the various items in a neat and precise fashion. It took me almost a week to teach Sarah my former housemaid how to organise a tea tray properly. This small but important point was not lost on Eleanor and she communicated her approval to me by an almost imperceptible arching of her eyebrows. I returned her gesture with an equally subtle nod of my head. Of course the poor boy was completely unaware of our admiration for his domestic skills as his entire focus was on ensuring he did not trip and lose the tray or its contents.

“Thank you Wilhelmina.” I said and from the corner of my eye noticed a smirk on Eleanor’s face.

“Most impressive.” Eleanor gushed in a voice that she managed to sound genuine but of course she could not leave it at that and added in a vaguely unsettling tone “For a girl new to domestic service.”

“Ah…emm… I…ah…thank you Miss.” he babbled incoherently but somehow recognising this was meant as a compliment he curtsied.

“Yes well done Wilhelmina.” I joined in to reassure the boy with a smile which seemed to ease his anxiety a little.

“Thank you Madam.” he answered and grateful for my approval he curtsied once more.

Eleanor watched him closely as he laid the various items on the table and from his nervous expression I could tell he was aware of this also.

“And tell me Wilhelmina,” Eleanor addressed him directly “Have you used my little gift?”

“Ah…I …err… I…”he stumbled with the answer as a vivid pink blush lit up his cheeks.

“Eleanor!” I protested, weakly I have to admit, “You are embarrassing the girl.”

“Nothing to be embarrassed about, we are all girls after all.” she declared and turned to William “Isn’t that right my dear.”

“Ah…I…”William continued to splutter

“These new pads can be a little tricky to fit the first time.” Eleanor said and although smiling her eyes locked onto his not allowing him to look away “Now lift your skirt so I can be sure you have positioned it properly.”

“But…I…please…it’s…”more incomprehensible stammering poured forth from his mouth.

I wondered what was going on in his mind and maybe Eleanor’s outrageous suggestion was the last straw. Of course even if he did such an attempt would be useless as while he was in the kitchen I took the precaution of locking the front door. One can never leave things like this to chance.

“Now, girl.”Eleanor snapped, her impatience quite evident.

Breathe and keep calm The voice inside counselled. The pad is fitted perfectly and our member is neatly tucked away. There is no evidence of masculinity. Remember you’re a servant girl and must do as you are told. Breathe and remain calm.

Perhaps it was shock, maybe the severe tone of Eleanor’s voice after all she can be extremely strict with her servants but I strongly suspect it was the vulnerability foisted on him by the mortification of being forced to wear female clothing. Whatever it was I keenly observed the consequences as his head dropped in abject humiliation and his hands slowly lifted first his skirt and then his slip to reveal the satin fronted girdle with delicate lace edging. I admired both but then I should, as they were mine and I do have excellent taste in lingerie and foundation wear.

“Closer, girl” Eleanor instructed her voice softer now but remaining authoritative nonetheless.

William seemed close to tears as he advanced slowly before coming to a halt in front of us his groin area level with our faces. His expression, a combination of fear and shame, silently pleaded with me as Eleanor moved closer to satisfy her curiosity. A pathetic yet sweet whimper escaped from his mouth as the back of her hand caressed the girdle’s heavy and wide satin panel.

“This is very like one of yours darling.” she said, her eyes not moving from the garment. “And the slip is the one I gave you for your birthday last year.”

I could see he had taken great care in not only affixing the feminine product but in concealing any obvious evidence of that disgusting male appendage. A casual visual inspection would suggest the region was female.

But Eleanor, as I knew only too well was anything but casual.

She looked up and smiled at him, her fingers still lightly stroking the satin panel.

“You are a very lucky girl,” she said softly although I’m certain he was not of the same opinion. Her fingers lingered a few seconds more before she added “To have such a considerate mistress. I do hope you are grateful.”

I suspected her referring to him as a girl in such close proximity calmed him somewhat as he nodded eagerly before answering in a voice that was a little higher and more feminine  than I expected.

“Oh…yes Miss… very lucky.”

Eleanor’s features imperceptibly morphed into an almost saintly expression and her mesmerising stare ensured his eyes remained latched firmly onto hers as she spoke softly,

“Now part your thighs like a good girl.”

She had done this to me on many an occasion so I knew that he felt almost compelled to obey her without a second thought and as his thighs slowly separated her hand slid gently between them and quietly nestled there. Such was her control over his emotions that although he remained silent and his facial expression did not reveal panic, his eyes told a different tale. Confusion, fear, shame and more besides, all spinning around inside that poor masculine brain of his and unable to communicate his fears by any means whatsoever. Another low whimper left his mouth and I guessed Eleanor had moved her fingers gently. She waited a few seconds for the moment to pass before repeating the procedure which naturally elicited the same result, only this time his mewling was more pronounced. Her hand remained for a few seconds longer and I perceived a slight tremble in his knees.  I suspect Eleanor detected this also and she reluctantly removed her hand but not before squeezing gently on the pad and smiled reassuringly at him. The last thing she wanted was a fainting episode. If he really was a girl I expect that by now he would be quite moist between the legs, what the condition of his male organ was I have no idea as the sanitary pad did an excellent job in secreting the vile object.

“I’m sure it’s a little cumbersome.” she said with a smile concluding his inspection “but so very necessary, isn’t that right, my dear?”

His brain still dazed and confused from her ministrations he found himself nodding in agreement. She gently eased the slip and skirt from his fingers and arranged them to her satisfaction around his knees before patting him gently on his tightly girdled buttocks.

“Now that was not so difficult, was it?” she continued smiling and waited for him to acknowledge it with another nod.

He looked blankly at me for direction.

“You may go Will…” I began before quickly correcting myself “…Wilhelmina, I will 

Before I could finish the sentence Eleanor interrupted me,

“Do you know darling,” she began, addressing me but her eyes remaining on the disoriented housemaid “Wilhelmina is really not a name for a servant girl it is far above her social station. I have an Aunt Wilhelmina, a formidable, imposing woman I doubt she would be impressed that your maid has the same name. Not only that, you have already referred to her as William on a number of occasions. It is far too overpowering a name for such a timid creature, we should really try to find something more suitable, more feminine.”

“What did you have in mind?” I asked as I watched an expression of yet more disbelief creep into William’s face

“Oh I don’t know, Sarah… possibly Jane, Hilda perhaps.” she said looking at William for inspiration.

“My last maid was a Sarah.” I replied “I would prefer a change, Jane, a little too plain I think and Hilda…oh dear… so old fashioned.”

Just as I said this I noticed a little animation began to slowly steal back into William’s face and the poor dear suddenly began to realise yet another part of his identity was being taken away from him. Surely he must have realised I could not continue referring to him as William and Eleanor was right Wilhelmina is far too patrician a name for a housemaid, female or male. I felt a little sorry for him and suggested to Eleanor,

“Should we ask hi…” I faltered before recovering immediately “…her?”

“Ask a housemaid her opinion?” Eleanor dismissed my proposal out of hand with a laugh. “What would your mother say to that darling? No she is your servant and you can name her what you wish.”

“Isn’t that right my girl?” Eleanor once more fixed the pitiful figure with her steely stare, the unfortunate young man still probably having flashbacks from her inspection could only nod his agreement.

 

“Something traditional but not old fashioned.” Eleanor mused still concentrating on his face which clearly began to make William nervous once more. “Something with a pleasant sound, easy to remember and pronounce and in keeping with her personality, of course.”

“What about Nancy?” I said.

“Nancy!” Eleanor repeated a smile coming across her handsome face. “Perfect.”

“Nancy...”I smiled repeating the name and looked at the young man “Nancy the housemaid. Far better than Wilhelmina.”

“And more appropriate.” Eleanor said and turned her attention once more to the cheerless youth “Don’t you think…Nancy?”

Both of us were beaming at him and I could see the working of his brain behind his sad eyes telling him not to risk further humiliation or perhaps worse by disagreeing.  It was clear to me – and to him- he had little choice but he nevertheless tried in his pathetic manly way to plead with me.

“I..ah…but…”he bleated but seeing my eyes narrowing slightly he quickly came to his senses. Humiliation engulfing him, his eyes dropped to the floor as he answered Eleanor.

 “Yes Miss.” he murmured.

“You should really thank your mistress, girl.” Eleanor said a little sternly “After all it she gave you such a pretty name.”

“Thank…Thank you… Madam.” he managed to say and noticing Eleanor’s eyes on him curtsied.

“Now run along Nancy.” I said “I’ll ring when I need you.”