Regrets...He's Had A Few - Short Story plus illustration

 

It’s been a while.

This is a short piece which would usually take a few weeks to write but my levels of concentration are practically nil and it took over two months. There are plenty of ideas but at the moment I’m struggling with various issues so not sure when the next post will be.

To any Ukraine readers – my thoughts, support and best wishes are with you.

Thanks W – This one’s for you.

 

Take care

Carrie

Regrets…He’s Had A Few.

By

CarrieP

For William, every day was one of regrets.

So many regrets.

For the decisions he had made or more accurately, the ones he did not make.

Regret, for bending so easily to his future mother in law’s forceful personality. Regret, for compliantly and unquestioningly taking the various herbal supplements she had insisted would greatly benefit his body and mind. Regret, for not immediately refusing to wear the dreadful unmanly clothes she had bought for him , the shirts that looked more like women’s blouses in silk and satin, the wide legged and high-waisted pants, the two inch patent leather shoes with tiny bows. Regret, for being brow beaten into addressing her as Mummy.

Regrets, for these and so many other things that had degraded his masculinity and weakened his spirit.

 However, his greatest regret was for allowing himself to slide carelessly, almost unconsciously from a red-blooded, vigorous, independent male into a weak, helpless ,vulnerable facsimile of a man.

For weeks he was forbidden to view himself in a full length mirror  he still should have been alert to the small yet noticeable changes in his body, the nascent round mounds on his chest that grew bigger as the days went by and at the same time there was a corresponding reduction in the size of his genitalia. Now barely visible, his manhood appeared to be hiding of shame in his pubic hair.  Noticeable also, was the increase in the size of his buttocks, accentuating his small waist and giving him a vaguely hourglass appearance. The little masculine strength he’d possessed had ebbed away and his arms now resembled those of a girl. At first he refused to even acknowledge these developments but eventually when his future mother-in-law finally allowed him access to a mirror he was forced to confront a new reality. Horrified at the girlish figure reflected back at him he burst into tears, much to the delight of the assembled servant girls.

He pleaded with his fiancée, but Caroline, having warned him on numerous occasions of her mother’s overbearing persona and telling him forcefully to stand up for himself,  felt he had no one to blame but himself for allowing it to happen.  She conceded that his altered figure was most unfortunate but she expected the effects of the herbal supplements to diminish in the coming months.  To his consternation she also informed him she would be away on business for several weeks and it would be in his best interests not to voice his grievances too vigorously  as her mother could be most unreasonable when annoyed. It would be better for everyone, including himself,  if he ensured her mother was kept happy. Caroline pointed out that her mother, a powerful society matron, was used to getting her own way and life would be so much easier for him if he was more compliant, adding in a factual manner, that he had managed this quite well to date.

However, despite Caroline’s  well intentioned advice  and in an effort to regain his self-respect  he tried to rebel but his feeble attempt at asserting his fading masculinity was quickly dealt with and he immediately  found himself draped over his mother-in-law’s knees, receiving a sound spanking with her wide antique silver hairbrush.  Of course he squealed and kicked his legs but she was far too strong for him, finally exhausted and unable to break free he submitted to her punishment. His utter humiliation was compounded by the presence of a number of her housemaids who had been dusting and vacuuming their mistress’s bedroom when the unfortunate incident occurred. Naturally they  made little attempt to hide their amusement at his mortifying predicament.

After the abject failure to regain some semblance of manliness he was left in no doubt he would now be firmly under her control and subject to her authority in all matters. He was now under no illusion as to what was expected of him – obedience and subservience. From that moment he was required to address her as ‘Mummy’, yet another source of hilarity for the servants.

Not wishing to repeat the ignominy of another spanking he meekly accepted his fate and continued to wear the ghastly clothes Mummy had ordered him to wear, the palazzo or capri pants, the satin pussy bow blouses. He  dreaded  having to accompanying her to fashion shows or on  various shopping trips to  exclusive stores  where much to her delight and his embarrassment he  was often mistaken for Caroline by the other middle aged matrons. His only consolation was that there were no other males present.

Bedtime brought little respite. His future mother-in-law was greatly unimpressed by his own nightwear, finding it far too inelegant and unsightly for the exquisite décor and feminine ambiance of his new bedroom. She insisted he should wear something more suitable to compliment the genteel surroundings of his boudoir. Of course he briefly considered a protest but her steely stare and the prospect of being placed over her knees quickly dissuaded him of even broaching the subject. She dispatched Agnes, her lady’s maid to retrieve some of her own pyjamas for him. All were heavy satin in pink, lavender, peach and other similar feminine hues with intricate embroidery favoured by women on the sleeves and lapels.  He watched dejectedly as Agnes, laid out a pair in a soft rose colour on the bed, her lips forming a faint yet unmistakable derisory smile as she arranged them neatly on the satin quilt. Needless to say it was an extremely restless night for the young man, the satin enveloping him was agonisingly tortuous yet at the same time excruciatingly pleasurable.

Following a most fitful sleep, the morning brought even more troubles. As he removed the dreadful satin pyjama to his utter horror he discovered a glaring stain in the groin area, clearly visible on the soft material. In an attempt to conceal the shameful blotch he wrapped the pyjama top around the bottoms before placing them in the laundry basket, he showered and dressed quickly before Agnes made her appearance. Now fully dressed in the awful clothes that Mummy had laid out for him the night before - a hideous plum coloured palazzo pants and what he tried to convince himself was a silk shirt rather than a ladies blouse- he greeted Mummy’s maid. The look of disappointment on her face was quite noticeable. Agnes had on numerous occasions insisted on dressing him on the flimsy excuse that he did not have a valet, these were most humiliating experiences as she fussed over him treating him like a five year old. Quickly following Agnes was one of the housemaids who, to his great relief, emptied the laundry basket before Agnes could examine them. He allowed himself a small sigh of relief, his embarrassing secret was safe.

Until of course that night, when both Mummy and Agnes entered his bedroom. He had already removed his clothes and was just about to put on the appalling teal coloured satin garment that had been laid out on the bed for him. A knock on the door and Mummy’s voice made him reach for the matching heavy quilted full length dressing gown in the same womanly colour.

“The housemaids have informed me of an unusual stain on your pyjamas” Mummy said walking past him into the room, Agnes following closed the door. William’s face turn crimson as Agnes, with a contemptuous smile, held up the offending article.

“I…ah…I…it…”he spluttered.

“No need for explanations.” Mummy said in a conciliatory tone “I understand the male has very little self –control, isn’t that so?”

“I…it…I did not…it was …”he continued to stumble.

“As I said, no self-control.” Mummy continued.”Fortunately there is a solution. Agnes, show Master William the remedy to the male problem.”

He gasped as the maid, unable to disguise her delight, held up a long, sturdy yet distinctly feminine garment.

“To ensure that you have no further embarrassing incidents you will wear one of these every night under your nightwear.” Mummy informed him.

He tried to speak but no words left his mouth.

“Your night girdle.”Mummy explained impassively as if this was an everyday occurrence. “And as an added precaution Agnes has suggested a sanitary pad. Ladies wear them at night during their time of the month to prevent disagreeable leakage. A girl can’t be too careful, don’t you agree William?”

As she handed him the heavy girdle a barely audible squeak escaped from his throat.

“Now put it on like a good boy.” Mummy said “Or perhaps you would like Agnes to assist you?”

This was a hideous turn of events and he was completely overwhelmed by her demands but as Agnes brought the evidence of his embarrassing ejaculation closer to his face he understood there was nothing he could say that would allow him an escaape.

He hands trembled as he held the girdle, the white satin of the front and rear panels separated by a denier of elastic far heavier than he had ever encountered.

“Come along William, no need to be so modest.” Mummy instructed in a clearly impatient voice, adding “You have nothing we have not seen before.”

Turning his back and still with his dressing gown on, he tentatively and very awkwardly placed one foot into the girdle, then the other and began to draw the heavy garment up his legs. Reaching his thighs he began to struggle. Before he could object, not that he was capable of such an act of defiance, Mummy relieved him of the dressing gown.

“No need to be shy William.” she laughed lightly.

Naked and exposed he pulled and tugged the girdle over his thighs and looking down between his legs he could feel tears of shame welling up inside as he saw the sanitary napkin nestling in the girdle’s gusset.

“Oh do get on with it William.” Mummy said curtly, her irritation beginning to show.“Ladies do this every day, just grin and bear it like we do.”

Feeling more vulnerable and exposed than ever William continued to draw the monstrous garment over his thighs and felt the pathetic shrunken sexual organ between his legs settle into the folds of the soft sanitary pad. His shame intensified and did his best to contain the tears welling up inside.

“Maybe you are right Agnes.” Mummy addressed her maid as she watched her future son-in-law strain to pull the girdle up his body, “Perhaps he does need a lady’s maid to assist him.”

William although extremely disorientated, heard the remark and despite his confusion and self-pity  immediately recognised his situation could indeed  get worse if he failed to placate his future mother-in-law. He redoubled his efforts and making one last effort he managed to settle the girdle an inch or so below his ribcage. Almost at once he felt the constriction of the garment on his abdomen, the girdle’s crotch squeezed tightly against his genitals and he was aware of the unfamiliar bulky sanitary pad pressing against them.

Mummy and her maid observed the pitiful figure before them with amused expressions and William suddenly became conscious of the small yet prominent feminine mounds hanging from his chest. He lifted his hands to cover them which caused even more delight to the onlookers; he could hold back the tears no longer and began sobbing.

“Oh dear.” Mummy said in a sympathetic voice and drew him to her bosom to comfort him. “No need to cry my darling boy, you’re just tired and a little confused.”

Agnes lifted the pyjama top over his shoulders and meekly he allowed her button it, she pulled down the bedclothes and sitting him on the bed drew the satin pyjama pants up his legs then helped him stand.

Mummy slipped her hand between his legs and looked him directly in the eyes as she squeezed firmly, his eyes dropped to the floor in shame.  The large wad hugging and protecting his now diminutive organ meant he was only vaguely aware of a slight pressure.

“Perfect.” she said with a satisfied smile and gesture to her maid to confirm her conclusion.

“Oh yes, Madam.” Agnes grinned in confirmation. “Fits wonderfully, just like it would with a girl. One could not tell the difference.”

William could hold back his tears no longer and began to cry.

“Yes, just like a girl Madam.” Agnes repeated her face unable to conceal her satisfaction at the outcome.

“There, there William.” Mummy consoled him and dabbed his cheeks with a tissue as she put him to bed.” No need to be upset, this is for your own good.  We don’t want another embarrassing incident, now do we?”

“But…” was all he could manage to reply as Agnes slipped a heavy satin sleep mask over his eyes.

“Hush now and sleep.” Mummy said, “You will feel so much better in the morning.”

The morning merely brought a further erosion of his masculinity, as if by magic, and to his great disappointment not to mention discomfort Agnes appeared just as he awoke.

“Good morning Master William, I hope you had a restful night.” she greeted him in a breezy fashion fussing and straightening the heavy quilt with the deep quilt, she added with a snigger. “Madam has asked me to check for any…leakages. When you are showering I will inspect your girdle and pad.”

When he emerged from the bathroom he saw Agnes had made the bed and laid out his clothes for the day, the usual ghastly ensemble of clothes that at best could be described as unmanly, high waisted pants in coral with wide legs and a matching shirt in silk which was, in reality, more of a blouse with long sleeves that ballooned out at the elbow and gathered again at the wrist. Dreadful,  of course but over the last several days his resolve  had been so weakened  and undermined  by Mummy’s overbearing personality he now felt quite helpless. However despite this erosion of his masculinity he could not prevent himself gasping at the sight of the long legged panty-girdle and long-line brassiere which lay next to the clothes.

“These pants are particularly tight fitting.” Agnes said, picking up the object of his terror and displaying the girdle to him between the fingers of either hand , she smiled encouragingly  “So you will require a little help ensuring they accommodate your figure properly. This is the ideal foundation wear for just such a purpose. Now be a good boy and put it on.”

He looked at the garment in her hands and recoiled in horror which brought an immediate reaction from the maid. Her eyes narrowed and her expression grew darker, an almost inaudible growl reached his ears.

“Now” she barked.

He had never heard her speak in such a tone and he was so alarmed he instantly took the girdle trying to steady his shaking hands. Turning his back to her and still wear his long quilted dressing gown, he placed one foot and then the other into the girdle’s legs and as he had done the previous night began sliding  it up his thighs, gyrating his hips as he did so. He found it easier than the previous night as the rear of the garment had a long zip running down it separating the satin material and so did not have to wrestle with it as much. The thought struck him that he would now spend almost twenty four hours encased in women’s foundation garments. However, the threatening look on Agnes’s face immediately concentrated his mind and he somehow managed to struggle into it. Covering his private region and most of his buttocks he nevertheless laboured to locate the zip at the rear. The maid immediately took charge and removed hi s dressing gown,  in the process she brushed  against his small yet promising fleshly breasts with her hand. He could not be sure if his blush was as a result of wearing a girdle or having his exposed breasts touched. Not that it mattered , not only was he humiliated but completely helpless and at her mercy.

“This is exactly why you need a lady’s maid, young man.” Agnes said as she stood behind him and began zipping the girdle.

He felt as if he had tight heavy bandages enclosing his thighs to his knees as the heavy elastic mesh compressed his flesh, the dainty lace at the hems belying the strength of the fabric. He gasped as the maid began zipping him into the long, heavy garment and as she worked her way up the garment his gasp turned into a whimper.

“Hush now Master William, and breathe in.” Agnes spoke softly with not even the merest hint of her previous displeasure in her voice and as the zipper reached its destination he felt the tight embrace of the girdle constrict his torso. He immediately recognised this garment was far more confining than the one he wore the night before.

She ran her hand over his tightly restrained satin clad buttocks and squeezed gently, his helplessness was overwhelming, his eyes closed as if to blot out the shame but the real reason was he knew what was coming next and he was powerless to resist.

With his eyes remaining closed he felt his arm being lifted and a thin strip of material slid up onto his shoulder immediately followed by a similar sensation on his other arm. A tear ran slowly down his cheek as he felt more heavy elastic being wrapped around his chest and tightened  as Agnes quickly placed the brassiere’s hooks into to the corresponding eyes.

“Your first brassiere.” She said, her voice a mixture of pride and triumph. Placing a finger under his chin she lifted his head and told him to open his eyes, when he did not comply he felt a sharp blow to his backside and although the heavy material softened the impact his eyes opened automatically.

The full length mirror reflected a familiar masculine face but a figure that would not be out of place in an advertisement for ladies foundation wear. The tight girdle, extending from just below the ribcage to just above the knee moulded his male trunk into a more womanly shape, the matching long-line brassiere containing his small yet plump bosom suggested a reasonably attractive feminine figure. Agnes smiled as she made minor adjustments to the brassiere’s straps.

“Madam will be pleased.”

“Madam certainly is.” Mummy’s voice rang, suddenly announcing her entrance, her admiration for her maids work clearly etched on her handsome face. “What a wonderful figure.”

William, feeling the brassiere’s shoulder straps biting into his flesh and the tightness of the heavy girdle constricting his abdomen and thighs squirmed visibly.

He made a feeble attempt at a protest but if either of the women heard they ignored it as they quickly helped him get dressed.

“My friends cannot wait to meet you.” Mummy said as she placed a string of pearls around his neck,” I have told them how adorable you are and how Caroline is such a lucky girl. Now we have a lot to do as they are arriving this afternoon and staying for the weekend.”

Underneath his sturdy foundations William’s stomach lurched at the very idea of meeting anyone dressed in such a fashion.

The day was spent supervising the housemaids as they prepared the various rooms for their mistress’s guests. Having spent several days in the emasculating clothes Mummy had chosen for him, William had almost grown used to the smirks and the mocking remarks of the maids as they went about their chores. And today was no different. They admired his blouse and his new pants saying how fetching the colour was and how his pearls complimented his outfit. But worst of all was their admiration for his figure which to any female eye could only be achieved through the strictest of girdles.

Likewise Mummy’s friends were gushing in their praise for his choice of outfit and how he had the ideal physique for such an ensemble. To his horror he was told there would be a dinner in his honour that evening at the private members club they all were members of.

As ladies do, they assembled in Mummy’s luxurious and spacious bedroom in the late afternoon for drinks and to discuss plans for the evening ahead.

“You do realise Theodora.” one said eyeing William “There may be a difficulty in William gaining entry. As we all know, it is a female only establishment. ”

“But he is so adorable, not like other males, darling.” another said and to his embarrassment, tracing her hand across his slightly protruding bosom. “He could very easily pass for a girl.”

Knowing glances were exchanged, Mummy and two of her friends quietly  left the room while the other s gathered around William seemingly unable to contain their curiosity. Hands caressed his face; he felt another touching his brassiere encased breasts, he felt his buttocks being squeezed gently and worst of all, the sensation of a hand between his legs.

Frozen to the spot, his mind in complete turmoil, he could nether move nor speak.

After what seemed like an age , he heard Mummy’s voice from beyond the gaggling female throng.

“Royal blue would really suit him. Of course he would have to wear a corselette.”

“And matching petticoats of course.” Another voice added.

William turned to see Mummy and her friends enter with several dresses and voluminous petticoats.

He barely noticed the hands unbuttoning his blouse and another pair undoing his pants.

“We should try the pink satin one first.” one of the women said “Pink is a delightful colour for our type of male. It has such a calming effect. We can put him into the royal blue satin afterwards.”

“I’ll ring for Agnes, she can help us in case he becomes a little agitated.” Mummy smiled as she began unzipping William’s girdle “One never know there may still be a little masculinity in there, isn’t that right William?”

“Aaah…”

The sound was barely audible as he felt female hands grapple with his brassiere and girdle.

“Don’t worry my darling boy.” a voice said “You will be the prettiest girl there.”