Pyjama and Early Bedtime Punishment becomes permanent for this office worker

Philip had thought himself very lucky when Gertrude Hinkle began taking an interest in him. The twenty six year old virgin was flattered that an attractive thirty eight year old female actually spoke to him about anything other than work. 

He was supposed to be the office manager but he knew most of the women in the office openly disregarded his instructions and laughed at him behind his back. Philip was the newcomer amongst years of experience who had been "fast tracked" into middle-management thanks to his late godfather securing him a position in the company.

Gertrude was different, she would listen to him  sympathetically nodding as he moaned about his "useless staff". Eventually she knew all his secrets. He just couldn't help telling her about his trips to a special lady who once a month would spank him and tell him he was a naughty boy. Of course it was never quite what he anticipated, quite what he imagined,  quite what he looked forward too, but it was the best he could ever hope for wasn't it? Then he told Gertrude how he paid for his excursions. He had been smart, Head Office had never suspected a thing. He hadn't wanted marriage, no, that had been Gertrude's idea, he didn't really have much choice did he? Not if she did what she said she would do. She had chosen his suit and arranged everything, even chose his Best Man, since he had no friends.
At first it had been heavenly for him, she ordered him about, told him exactly what to do and how to behave and took him across her knee and smacked his bottom. Then one day she smacked and smacked and smacked until he was wriggling and bucking and writhing on her lap but still she continued. He screamed and cried real tears of pain. She hugged him, kissed him and tucked him into bed. She comforted him and told him she would look after him. And now she does.
Philip is now a thirty three year old virgin who is treated like a toddler. Gertrude is his mummy and he is never allowed to  act his age. You would think Philip would be grateful, ecstatic to have fulfilled his fantasy. But no, now he cannot choose when he will get his bottom smacked, he cannot choose when he will go to bed, he cannot choose which clothes he will wear. Ever.    

Nanny Susan concluded. To be honest I got confused about how to finish the story. This is the version I intended to post to Betty's story Board site to finish it off. It is a re-write of the end to Philips Treatment, but it seemed a bit harsh and not in keeping with the mood of the earlier parts. I cut short the ending on the story site to maintain the cosier feel. Anyway, it is finished with now.

Nanny Susan lowered the cot rail and gently ushered Robert toward the waiting bunny rabbit motif covered bedding. He was slightly reluctant at first but her firm hand placed strategically on his backside guided him as he climbed on the mattress.
The base of the cot was only a few inches from the floor, yet the rail extended to the level of the alcove.
 "Into beddy-byes, there's a good Baby Bobbykins, time to go sleepy byes, snuggle down now." She cooed. Instead, Robert stood defiantly on the cot mattress.
"It's vewy erwee fo beddy-byes Nanny Thusan, too erwee, me no thleepy." Nanny Susan didn't argue, instead she raised the cot rail, secured it in place, opened the skylight window and went to fetch another bottle of sleepy time milk.
Robert felt a bit silly, standing there in the cot in his babyish pyjamas, wearing nappies, so he grabbed hold of the metal bars of the cot and gave, what he imagined was a firm rattle. Instead of course he hardly disturbed them. Next he turned his attention to climbing out. Disturbingly though, he discovered, that due to the incline of the alcove the widest gap available was far too small to climb through. He was effectively imprisoned  in the cot. His thoughts clouded once again and he sat down with a plonk.
Nanny Susan returned with a large bottle of sleepy time milk, passing it to Baby Bobbykins through the bars of his cot he eagerly took it. He liked sleepy time milk.
"That's a good boy, all gone." Time for night-nights, Nanny will see you in the morning when we will be extra loving to Aunty won't we?"
Robert nodded, the chill from the open window encouraged him to snuggle under his blanket and he sleepily took his dummy from Nanny Susan and settled down to a very early bedtime for a seventeen year old.
The next morning Robert was taken downstairs and put into his high chair. Nanny Susan was feeding him detestable milky pudding and his bib was once again encrusted with the spillage. he was still wearing his yellow, footed bunny rabbit pyjamas  and underneath his thick fluffy nappies and rubber baby pants which, up until ten minutes ago had been quite dry. He had begged Nanny Susan to let him go to the bathroom but se had been insistent  that he had to wait until after breakfast, of course the inevitable had occurred and he now sat uncomfortably in flooded nappies and having to swallow semolina pudding for breakfast.
"Here comes the choo-choo train." Nanny Susan's spoon was poised to insert the yuckiest mouthful of semolina yet into Baby Bobbykins reluctant mouth, when Aunty walked in the kitchen.
It is difficult to convey Roberts reaction to seeing Aunty. Nanny Susan's spoon was swept aside as he bobbed up and down in his high chair, clapping his mittened hands together in a frenzy of delirium as semolina was sent cascading around the kitchen.
"Well, well what a welcome. It has been a long time since anyone has been that pleased to see me."
Aunty took Robert under the arms and lifted him out of the high chair and sat her seventeen year old nephew on her lap, just as she used to.
"Oh Baby Bobbykins, how sweet you look wearing your bunny rabbit jim-jams, you told me you didn’t want to wear them any more, you said they were far too babyish for a big boy of seventeen like you, remember?"
Robert blushed. He did recall the big argument  they had.
"Me sowwy Aunty. Baby Bobbykwins wuvs his bunny wunny jim-jams. Me weally sowwy for being a naughty boy and making you sad. Pwease fogive mi. Pweeeese?" 
Aunty stroked his hair.
"Do you promise to be a good boy and obey Aunty and Nanny Susan without question?
"Oh yeth Aunty, I do, I do."
Aunty directed a smile toward Nanny Susan.
"Well then, let's get you cleaned up and ready for a new start to a new day shall we."
Every time Aunty entered the room, Robert would gleefully run toward her and hug her tightly. He clapped excitedly when she spoke to him and he snuggled into her and chatted happily to her in baby talk as she sat him on her knee. Baby Bobbykins had indeed embraced Nanny Susan's recommendation.
What's more, he had come to accept his daily routine of trips out to the park in his pushchair, a walk around the duck pond holding Nanny's or Aunty's hand dressed in his little boy outfits for all the world to see. Indeed he was now so well known in town that hardly anyone took notice of them any more.
The young man who regressed almost to babyhood. A sad case but still, he was well looked after, and you never know, he may snap out of it one day.
Then home again, a bath, nappies pinned on, rubbers, jim-jams and an early bedtime in his snug little cot, of which there is no escape. And all really achieved with the help of daily doses of sleepy time milk.


One afternoon as Robert had been put to bed particularly early after happily consuming a second bottle of sleepy time milk, he was hazily aware of Aunty and Nanny Susan staring down at the seventeen-year-old youth as he lay in his cot.
He woke up to find he was lying naked on a blanket downstairs. Where was Nanny? Where was Aunty? Sitting himself up his hand brushed against on object. It was a traditional baby’s dummy. He placed it straight into his mouth and happily began to suck upon it.
Objects were strewn about the floor, he attempted to stand up but was unsteady and quickly sat down before he fell. Sucking on his dummy he crawled forward and was happy to discover his nappy, loosely pinned and a pair of his rubber pants. Knowing he should be in bed he attempted to pull on the nappy himself before he also came across his bunny rabbit pyjamas, at finding them he cuddled them to his body before pulling on the footed pyjama bottoms before buttoning on the top.
“Hmm. I see.” Said a strange female figure carrying a briefcase, alongside her stood another strange female.
Roberts lower lip began to quiver before the comforting arms of Nanny Susan sat him upon her lap. Apparently they both wanted to talk to Baby Bobbykins but he was much more interested in being entertained by her gently bouncing him up and down. He always seemed to enjoy those sessions and she had to shush him quiet as he started to giggle and laugh and wanted to talk to her.
“It’s very unusual regressive behaviour indeed.” Said the strange female as she copiously made notes.
“Yes it was a quite rapid regression over quite a short period." Aunty proclaimed.
"As you saw for yourself, his urge to act in an infantile manner is still well established.”
Robert began to take more notice of the conversation.
“This behaviour was witnessed at its onset you say?” Asked the briefcase lady who was taking notes.
“Oh yes.” It was Nanny Susan speaking now.
"He was seen outdoors by the girls from the local  school here in his babyish pyjamas acting as if he was a little boy. Then he insisted we buy him a pushchair and take him into town sucking on a baby’s dummy dressed as a child in short trousers."
Aunty continued. "It was soon after that I discovered the nappy and the bunny rabbit pyjamas in his bedclothes, soiled, I am afraid to say.”
She dabbed her eyes with her handkerchief as she spoke. 
Roberts head was losing its haziness and the meaning of the conversation was penetrating his rapidly clearing mind.
“Wait a minute, not baby.. baby…boy.."
 He murmured. Unfortunately for Robert, Nanny Susan quickly popped the baby’s dummy into his mouth and held it firmly in place.
“Mmmmmmmpfh!”
“Is he trying to say something?” Asked the note taking female.
Robert's hand reached up onto Nanny Susan's but hers was the stronger she held the dummy firm.
“Oh dear, he was telling me he needs a drink, will you excuse us please?”
“Of course young lady, we have seen enough. Off you go and look after Robert. I do so admire you for standing by him. A lot of girls your age would have been reluctant to help. Goodbye and goodbye to you too Robert I hope you get better soon.”
The female tousled his hair; Robert widened his eyes in a desperate, plaintiff cry for help and started to flail his arms about wildly. Nanny Susan held the dummy tightly and rapidly exited the room.


Robert was in the nursery; lying on the changing table his hands and feet encased in mittens and bootees. He was tightly pinned into nappies and plastic pants and resplendently buttoned into a pair of Thomas the Tank Engine, flannel footed pyjamas. The quieter was firmly positioned in his mouth and a dribble of saliva was already wending its way down his chin toward his, “Baby Bobbykins” bib. His peek-a-boo bonnet was in place and tied neatly under his chin.  

His Aunty, Nanny Susan and Miss Bracegirdle stared at the helpless Baby Bobbykins .
Nanny Susan tweaked the brim of his bonnet “He took me by surprise at how quickly the medication wore off, I will have to increase the dosage.”
“Well,” Aunty said, looking down at Robert, “thanks to you Nanny, it worked to our advantage. In a short while, once the committee’s recommendation is confirmed I will legally have jurisdiction over Roberts affairs.
Robert looked up at his mother with puzzlement.
She tickled his chin, as she spoke.
“My dear when your parents died their assets were left in trust for you. I had to make do with a limited amount each year.

When you turn eighteen in a few months time you will have access to a substantial amount of wealth. Far too much for a boy like you to be entrusted with. I couldn’t possibly have allowed you to have control of all that money."

Aunt Harriet paused to fussily adjust the frills on his bonnet.
“Fortunately, I now have power of attorney over your financial affairs, thanks to your awful regressive illness. No one would let a little boy have access to all that money would they Baby Bobbykins?”

Robert tried to sit up, his head quite clear and his anger manifest, but surrounded by three women he was quickly pushed back down and his wrists and ankles were quickly secured in the restraint cuffs on the changing table.
“Mmmmmmmpfh!”
“Now, now Robert,” his Aunt went on.
“Miss Bracegirdle has kindly agreed to join our little team. he so enjoyed meeting you she will be designing and making some delightfully infantile outfits for you to wear that will confirm your regressive natures to the good people of this little town of ours.
Susan will continue in the role of Nanny, she and her mother will be joining Miss Bracegirdle in living with us in our lovely new house in the country. There is a big garden where you will be able to sit in your pushchair and have lots of naps; I may even buy you a special baby’s pram so we can take you out for a stroll, won’t that be nice? No need to thank me I can easily afford it.
Your days will be short. Up at nine, plenty of exercise, walks in the garden and into town to show off your new little boy outfits then back for bath time and jim-jams at three and beddy byes by three thirty.
Robert struggled against his restraints as the teat of the bottle was forced into his mouth.
 “Of you go to sleepy-byes Baby Bobbykins,” his Aunts voice was saying from a long way off.
“Only three more years as a little boy until you are twenty-one, then we must persuade the authorities all over again to renew my jurisdiction. But don’t worry, by then you will be used to your nappies and jim-jams and you won’t ever remember being anything other than an obedient little Baby Bobbykins.”

mogg has posted another part of his excellent story, Anthony is Invited to a Party. It features the hapless boy re-entering the party wearing his blue striped winceyette pyjamas to suffer yet more humiliations. Don't forget to leave a comment for mogg after enjoying the read.

Letters from Pyjama Punishment Monthly. "Write to Matron", was a feature introduced to later editions of PPM. No doubt intended to widen its appeal, there were lots of letters such as these about short trousers.

Dear Matron

I live in the UK and a year ago when I was 17 my mother forced me to wear full schoolboy uniform including grey short trousers as a punishment for misbehaviour. Since then I have been educated at home using private tutors and have had to wear my school uniform and short trousers every day including weekends. I am also taken out in school uniform for shopping trips and doctor and dental appointments. Even though I appear a lot younger than 17, I look too old to be still wearing shorts and it can be terribly humiliating. Most schoolboys in the UK wear long trousers by the age of 11 so I look like an older boy dressed like a little boy. Mother has also re-instated  bedtimes and I now have to go to bed at 8.30 each night. I have protested that this is far too early for a boy of 17 but she is adamant. My mother says that short trousers have made me obedient and respectful and she plans to make me wear them for several more years! Are other boys of my age  kept in short trousers and school uniform as a punishment? Do you think my mother is right to treat me this way?

Michael

Dear Michael

Your mother is perfectly entitled to dress you this way. As she is no doubt supporting you financially you must wear what she buys for you. Is it so bad? I bet you look very smart in your uniform. Short trousers are ideal outdoor wear, it is very healthy for a young boy to feel the elements upon his skin. Similarly with bedtimes. 8.30 strikes me as a sensible bedtime during the week when you have lessons the next day. Remember an hour before midnight is worth two afterwards.

Matron

Matron
Older boys would be far better behaved if they were kept dressed as children in school short trousers as Michael was. My father remarried when I was 14 and I became the stepsister to an obnoxious 16 year old boy who had no respect for authority. Daddy was headmaster of a boys prep boarding school in Wales (this was the early 1970s) and promptly put my stepbrother into the school and into short trousers. He was kept in a class of 12 year olds for two years and wore shorts all the time, school holidays included.
When he was 18 he was sent to the senior school but kept in short trousers even though nearly all the other boys wore longs. He stayed at the school for three years and for the last two years was the only boy in his class still in shorts despite being five years older than the other pupils.

Short trousers made him respectful and obedient and he did as he was told without question. Although over two years older, he was always deferential towards me and accepted my authority in all matters. In his twenties he was still sometimes punished by my father by being made to wear short trousers for a weekend which caused him great humiliation particularly in front of my girlfriends who loved teasing him and treating him like a naughty little boy.
Ms Wendy Kirkbright

Dear Wendy
Thank you for your most interesting letter. Your father obviously understood the value of short trousers as a means of imposing discipline. Perhaps you could write again letting us know if you played any part in your step-brother's punishment and how old was your brother when he was finally allowed out of short trousers?
Matron

Matron

My stepbrother was punished by being made to wear short trousers up to the age of 27. He was made to wear them with his prep school uniform so he looked like an overgrown schoolboy. Typically he was kept like this for a weekend or two but he also had to spend two whole weeks of a family holiday in his punishment clothes when he was 24.
He hated being teased by my girlfriends and his face would go crimson with shame and embarrassment at their comments but he always managed to stave off the tears. He would often sneak off to his bedroom when my friends arrived at the house but I would go upstairs and drag him down to the sitting room by his ear so they could have a good laugh at his expense. They used to really torment him.
My father initiated most of his punishments and often took my step-brother out in his school uniform complete with short trousers several times during these periods.He often attracted strange looks as he undeniably looked too old to be dressed as he was. When we were on our family holiday we went to the cinema and for walks in the local park with him in his short trousers with his blazer and cap. He hated the humiliation but it certain made him well behaved. He looked very sweet and angelic.
Ms Wendy Kirkbright

Dear Wendy
Thank you for writing again and giving us a further insight into your fathers treatment of your step-brother. If the ultimate outcome was that of  a well disciplined, well behaved male then it was all worth while and you played your part in achieving this. A little bit of teasing is character building is it not?

Matron

A response to Lionel's letter. As I feared, Lionel's letter did not go down well with my Aunty. She instructed Mrs Jacobson to contact Lionel's wife to recommend several punishments one of which is documented below. I have little option other than to post it direct as my Aunt ordered me to do as I would not want to suffer any consequences due to another mans foolishness.

Lionel, you really are a silly man.

"Could you possibly have a word with your Aunt and ask her to E Mail my wife via your blog site and dissuade her from having such silly notions as I have no intention of being 'pyjamaed', treated as a servant or allow myself to be otherwise humiliated by a group of silly women."

You should know that I have written to Mrs Sykes -Patterson direct, to inform her of your pathetic, "appeal" to Wincy and no doubt by now you will have been punished in a suitable manner for your insolence accordingly. 

I though, take great exception to the tone you use. A group of silly women indeed. Let me tell you that we "silly women" are far superior to males and the sooner all men are subject to strict pyjamaring regimes and early bedtimes the better.

I sincerely hope your wife dresses you in your modified pyjamas and parades you in front of her sewing circle and Bridge club friends to emphasise how pathetic you really are. What is more, I want her friends to follow her example and impose a similar regime on their husbands too, letting it be known that it was your behaviour and actions that initiated their  pyjamarings.

I have proposed that your wife, Mrs Sykes-Patterson and Ms Clark arranges a garden party and that each female brings a specifically wrapped parcel that contains a pair of pyjamas especially made for their respective male partners. The men will  then come forward to select and unwrap their parcel.

They would hold up their pyjamas for everyone to see, then their partners will approach them to assist them in donning their new pyjamas. Once the male is duly pyjamaed, he will line up and watch as his compatriots unwrap their parcels and are attired in the nightwear their female partners have chosen for them until all the males have been subject to a pyjamaring.

Imagine your fearful anticipation Lionel as you nervously rip open the parcel to  unveil the nightwear your wife has decreed you must wear. You hear the gasps and at first, stifled laughter of the other ladies present as they feast their eyes on your voluminous pink striped pyjamas. Your head is bowed as you are publicly buttoned into the pyjama jacket. The top button secured with a safety pin to ensure closure.

Your hands disappear as they are enveloped by the length of the pyjama jackets sleeves and your miserable manhood is cocooned behind a mass of winceyette that cascades down and rests inches above your knees. And now Mrs Sykes -Patterson steps you into the pyjama bottoms, tent like, they are raised chest high and the extra long pyjama cord is passed around your waist before being tied off with several granny knots. The laughter from the ladies present is louder now as the full effect of your pyjamaring becomes apparent, the overlong pyjama bottom legs puddle at your feet  and you shuffle away to join the line of equally ludicrously attired males.

Who is the silly one now Lionel?

Mrs Jacobson