Wednesday, 16 May 2018

PPM offers some advice

Dear Pyjama Punishment Monthly

Even though I admire and enjoy your publication I must confess to having had doubts about the methods employed to discipline errant boys. Imagine my surprise when I discovered for myself that your recommendations could be deployed successfully.

My nephew is fifteen and typically lacking in manners and respect for his elders. One evening, after a heated debate about his staying out late, I decided to try a little experiment. While he was taking his bath, I locked his bedroom door. I then selected a pair of my most voluminous pyjamas, a yellow floral pair of robust flannelette and returned to the sitting room to await his return.

Soon, he was standing in front of me holding a wet skimpy towel in front of himself to cover his modesty. He demanded access to his clothes but I calmly told him that I had decided he was not going out tonight and pointed to the floral pyjamas warming on the radiator. 

I told him he could either put the pyjamas on or remain naked - the choice was his. Of course, he blustered about his 'rights' and such nonsense that he had picked up at school until I told him that he was still a child and under my strict jurisdiction.

He then pathetically attempted to change my mind by reminding me that I was expecting the female members of my book club. Foolishly, he assumed that in some way that would sway my decision. 

I informed him that future circumstances depended entirely upon him, if he wanted to be seen naked by my lady friends totally naked then that would be so, alternatively, he could appear modestly attired in his infantile sissy pyjamas. 

Having time now to consider his options, he decided the sissy pyjamas warming on the radiator were his best option. I watched triumphantly as he stepped into the pyjama bottoms and slipped on and buttoned up the pyjama jacket.

As I had anticipated, the pyjamas were far too large for his slender frame so I assisted by turning up the sleeves of the jacket and pulling the bottoms up high to shorten the length of the bottoms. He struggled with the unfamiliar female button arrangement and I happily fastened them for him. 

The effect on him was staggering, almost immediately after putting on the female pyjamas and being enveloped in the soft caress of the cosy winceyette material he was a different person. 

He politely requested that he be allowed to go straight to bed but I informed him he had to stay up to say night-night to my guests. When he asked me how we would explain his appearance he called me 'aunty', something he had not done for weeks.

We would say he was recovering from flu, I advised.  He had been so ill that he had run out of clean pyjamas and that aunty had let him borrow a pair of her warmest winceyette pyjamas I told him reassuringly. 

When my guests arrived he was politeness personified, sitting quietly and only speaking when spoken to. Everyone accepted our explanation of his unusual attire, some even commenting on how sweet he looked in his floral feminine pyjamas. Only when Miss Gotobed, produced her camera, saying she must have a picture of such a delightfully polite little boy, did he murmur an objection?

By now I felt sufficiently confident to give his bottom a little smack, he gave a small cry of distress before he complied, admittedly somewhat shyly, sitting coquettishly on my lap - a picture that is prominently positioned framed on my mantelpiece to this day.

At seven o'clock I told him it was time for bed and to kiss everyone night-night  He did so a little hesitantly but without a murmur and soon I was tucking him into bed in my daughter's old bedroom.

The next day I kept him dressed in his floral pyjamas to reinforce my newfound discipline and after school, on Monday I took him shopping and bought him some female pyjamas of his very own. His pyjamas are infantile little girl ones, in primrose and pink; soft winceyette with a frilly lace Peter Pan collar and teddy bear motifs.

Since then, if I feel he has misbehaved, I only have to clap my hands and say, ‘pyjama time please’ and no sooner have I spoken then he is ready for bed dressed in his girls' pyjamas, cuddled up beside me.

Thank you PPM for promoting this truly effective style of discipline.

Yours truly


Phillip Jones left a comment that I felt was worth a posting of its own. (Slightly edited by me)

It is always very humiliating being supervised by younger females and I have had the misfortune to experience this myself. My sister was two years younger than me but when she became thirteen, mother gave her full authority over me and she excelled in humiliating me with bath times and getting me into my pyjamas ready for bed.

My ex-wife was seven years younger than I was and it was she who initiated one of the worst experiences of my life.

It was a rare occurrence, but I was actually not working one weekend and we decided to hold a barbeque on Saturday. My wife invited a few of her friends and her mother. It was a hot day and I was tasked to cook for our guests, all going fine until my wife asked me to get her a drink, as I was still tending to the food I replied, “why don’t you get it I am busy, can’t you see I am standing here cooking for your guests?”

My wife gave me one of her angry looks and well grabbed me by my ear, she was a strong, dominant person and I was helpless as she led me into the lounge. She gave me a telling off that all our guests could hear and then put me over her knee and smacked my bottom.

When she was stopped spanking me she stood me up and took me to the bathroom, first washing my mouth out with soap for answering her back and then she bathed me and dressed me in an infantile nightdress.

She led me downstairs outside into the garden and stood me in front of my mother-in-law and her female friends. “This naughty little boy would like to apologise for his bad behaviour and he is going straight to bed after he has said nighty-night to everyone.”

I had to say goodnight to all our guests individually and when I had finished my wife took me upstairs to the spare bedroom and put me to bed with a blankie teddy bear and a babies dummy in my mouth. She closed the windows and drew the curtains and then left me in darkness.

I could hear our guests laughing at my embarrassment and enjoying themselves while I was tucked up in bed at 3 pm in the afternoon. I went to sleep knowing I would have the embarrassment of having to face our guests sometimes again and my mother-in-law in the morning. Now everyone knew how I was treated as a silly little boy by my younger wife. 

Sunday, 13 May 2018

Babysat by a younger girl. This was sent to me by someone who prefers to remain anonymous

When I was a 16-year-old boy my mother obtained an evening job that meant she was out of the house from 5 until 10 pm. Because I had once been in a little trouble that had resulted in my being escorted home by a policeman, mother insisted that Jocelyn, a neighbour babysit me. I was aghast, as she was only 15 and I did not want anyone let alone a 15-year-old girl babysitting me. 

Jocelyn was taller than me and very strong, she excelled on the athletic field. Once, a schoolboy bullied her younger brother, she cornered him in the school playground and lowered his trousers then humiliated him by spanking him on his bare bottom in front of everyone.

She would arrive a few minutes before my mother left the house and from the outset was very strict and I never dared disobey her. I was free to do what I liked until 7.30 when it was time for my bath. The first time she told me it was my bath-time, I thought she was joking and laughed however, I quickly discovered she was not joking as she immediately took me across her lap and spanked me like she had the boy at school then stood me in front of her and removed my clothes herself as she told me off for being a naughty boy. 

Once in the bathtub, I was shocked to realise that I was to be bathed under her close supervision. When she wasn't satisfied with my efforts at cleanliness, she would grab the flannel and wash me all over and I often received a smack to my bottom as I stepped out if she hadn’t been satisfied with my behaviour, she would tell me she had often spanked and bathed boys while she was babysitting them and that I would be no exception despite my age.

After my bath, Jocelyn insisted I put my pyjamas and slippers on which as you can imagine, I was not happy about, a 16 year old ready for bed in pyjamas and slippers before 8 pm.

Usually, my mother would arrive home at 10.15 and embarrassingly, I would already be tucked up in bed with lights out as Jocelyn determined that my bedtime was 10 pm.

Jocelyn babysat me until I was 17 and nowadays I regret never having never another female as formidable as she was. 

Thursday, 26 April 2018

Kept in Pyjamas by my Aunt

I have been quite poorly recently and was invited to spend time convalescing at my aunts, by invited of course I mean ordered. Promising to be there at four, it was only just after twenty past when I drove into her drive. Upon my arrival, it was obvious aunty was in a distressed state. I was upbraided for being late and worrying her by not calling. (She always thinks I will have been in an accident) 

Aunty proclaimed I was looking 'tired and peaky' and used her no-nonsense voice to order me straight upstairs to take a bath, she ignored my protests that I had showered before I departed and as usual, I was overruled and quickly found myself turning on the taps.

After only ten minutes soaking, aunty barged in and insisted on taking charge of my ablutions. She always maintains I don't wash my boy areas well enough and taking the sponge from my hands, proceeded to clean between my legs and then pulled my foreskin back to clean,"where little boys forget". I immediately protested and shouted out what aunty calls 'naughty words'.

For my outburst, the flannel was re-soaped and thrust into my mouth. "Naughty boys who say naughty words get their mouths washed out and earn a smacked bottom." She scolded, as I attempted not to swallow the soapy water that was swishing around my mouth.

"Come along, upsy-daisy," she sang as she removed the bath plug. The water gurgled away as she hoisted me out of the bath. Grabbing a towel from the radiator she gently massaged my skin dry. Aunty was very gentle and the warm towel soon had me almost dry but as she dabbed between my legs I gave out a small cry.

"Ouch." Aunty slapped away my hand and examined me more closely. "Are you drying yourself properly?" she queried. Your skin is chaffed, aunty will have  to put some cream on for you."

A pair of my 'visiting pyjamas' was warming on the bedroom radiator as aunty led me in by the hand. Quickly she guided my arms into the sleeves and buttoned me into the paisley winceyette pyjama jacket before indicating for me to lie on the towel she had lain on the bedspread.

"Legs up." Before I knew it my legs were thrust vertically upwards. "Hold that position." She ordered as she prised open the lid of a tub of Sudocrem.

"Aunty no!" Taking no notice she held my legs aloft with one hand and smeared cream all over my scrotum, penis and between my legs until she was satisfied.

"It's a good job I noticed, I shall have that skin problem completely cured before you leave."

She lowered my legs slightly and manoeuvred my feet into the pyjama bottoms and raising them. "Up," she said and I obediently lifted my bottom so that she could pull the pyjamas up over my bottom.

Standing beside the bed she tucked my pyjama jacket into the waist of the bottoms and pulled back the bedclothes. "In you get. It's bedtime for you."

"But aunty it's only five o'clock," I protested glancing at the bedside clock.

"Late enough for little boys who are not well and don't know how to look after their pee-pee area."She replied tucking me in and telling me to take a nap and that she would bring me up some soup a little later.

I had been at my aunt's for less than an hour and I had been bathed and put into pyjamas then tucked into bed. Could it possibly get worse?

More on short trousers and early bedtimes. Phillip Jones sent this as a reply to Wendy and I thought the content very worthwhile posting.

Good evening Wendy I hope you do not mind me replying to your post.

You remind me of my own sister who had my parents permission to babysit me and had permission to put me across her knee when required.

I too was kept in short trousers until I left home at 21. I had to wear shorts to school until I was 14 but every time I came home from was told to go and put my short trousers on to do my homework.

My bedtime was 6.30 pm but my sister, who is younger than me by two years, was allowed to stay up much later. When I complained to my mum that it was not fair, she told me my sister was a lot more mature then me and that I should consider her to be my babysitter.

From then on, my sister was the one left in charge when my mum went out and my sister always insisted on putting me into my pyjamas as soon as she left, even it it was only 4 pm!

Soon after I was married, my wife had a discussion with my mother who told her how I had been dealt with by her and my sister. My wife was entirely in favour of this style of discipline and one afternoon, when we where having an argument, my wife ordered me to go straight to bed. She led me upstairs to get my pyjamas on and get into bed.

That meant the spare bedroom and as she tucked me in she told me that my mother was right and that I was an immature child and from now on she would be treating me as one.

My wife did used to put me over her knee
and get me ready for bed dressing me either in little boy type childish pyjamas or a little girl type night dress.

My bedtime was 7 pm and I had to be in pyjamas ready for bed at 6 pm or even earlier if I had misbehaved. 

If she had friends coming over or if she was going out, my mother-in-law would babysit me which was humiliating and embarrassing as sometimes my wife would not have time to get me ready for bed so my mother-in-law would bath me and dress me in my little boy pyjamas or nightdress.

I wonder if my experiences are similar to you and your brothers situation?


Thursday, 19 April 2018

Short Trousers For Her Younger Brother. Thank you to Wendy from whom I received this letter.

I grew up in South Africa in the 1970's and 1980's, where schoolboys in short trousers were a common sight. Most boys wore shorts until they were sixteen or older - usually the standard grey flannel short trousers in the winter months and khaki shorts in the summer, always with the standard schoolboy knee socks with the turnover top. Some schools made shorts compulsory for even the seniors so boys would wear them until they were eighteen, nineteen or older if they had to repeat years.

My brother, who was two years older than me, was a typical example. Short trousers were compulsory for all boys at his school where he remained until he was eighteen. He cried when my parents then told him he was to remain wearing shorts until his twenty-first birthday. They were firm believers in keeping boys in short trousers for as long as possible as a means of control and to stop them getting big ideas. Up to the age of twenty-one, he wore shorts at all times and was never once allowed long trousers. His first pair of longs was a present for his twenty-first birthday and he wore them that day with great pride.

My parents felt that boys were immature and grew up far more slowly than girls and as a result should be treated and dressed like children for longer. I was allowed stockings and tights at fifteen and to wear makeup at sixteen and was regarded by my parents and others as a sensible young lady. My brother was still being put to bed at 8 pm when he was eighteen while 

From my fifteenth birthday, I was his designated babysitter, having been given authority over my brother and I was always left in charge when our parents went out. He had to do as I told him or else it was not uncommon for him to go across my knees for a spanking and be put straight to bed, sometimes well before 8 pm. People who did not know us automatically assumed that I was the eldest and because he was treated him like a little boy.

During his twenties he was occasionally punished by my parents by being made to wear short trousers, together with his old school uniform of blazer and cap, for a whole weekend. It was not surprising that he did not venture far from the family home while dressed like this but he was seen by a few visitors and subject to ridicule.

I think my parents were totally correct to keep my brother in short trousers to twenty-one and beyond. He was well behaved, obedient, demure and polite. He also looked extremely sweet in his shorts and my girlfriends would teasingly tell him what a smart little boy he was which always made him blush with embarrassment.

I do not have children yet but if I have boys, I hope I will keep them in short trousers until their mid or late teens or even older. I agree with my parents that boys are far less mature than girls and should be kept as children for much longer. Keeping them dressed in short trousers is an excellent way of reminding them of this fact. 


Thursday, 12 April 2018

Pink Pyjamas for a Naughty Nephew? Perhaps not!

It was four o’clock on Saturday afternoon and I had just been given a bath by my aunt. This had entailed an intrusive interrogation with a soapy flannel of the most intimate parts of my body ending with a mouth soaping so intense that I gagged several times as aunty worked the flannel around my mouth.   

"Come along, you naughty little boy, I will teach you to tell lies to aunty." My crime had been to "forget" to tell aunty I had crept out of the house for five minutes to have a crafty cigarette when I was supposed to be busy polishing the cutlery. Unluckily for me, I had forgotten about Miss Masterton, the spinster who lived opposite. She had used her binoculars to spy on me and had telephoned aunty to inform her that there was a miscreant outside wearing pale blue little boy pyjamas and smoking a cigarette. Of course, I was even more naive when I foolishly denied my crime after aunty had confronted me. Sadly, Miss Masterton appeared in person to confirm my guilt I had no choice but to confess and so found myself being stripped out of my rocket ship pyjamas and unceremoniously deposited into a soapy bathtub.

Aunty dried me roughly and marched me naked downstairs. To my horror, Miss Masterton was still there, she smirked as I attempted to cover myself. Aunty slapped my hands aside. "Not only did you lie to me about smoking but you lied about sneaking out of the house too. Well my lad, perhaps you won't be so keen to be seen in public wearing these." It was only then that I noticed that in Miss Masterton's lap was a pair of pink floral winceyette pyjamas. 

Grinning like a Cheshire cat she held up the pyjama jacket. With aunty behind me ensuring my compliance Miss Masterton guided my arms into the soft, brushed cotton, frilly pyjama jacket and I was turned to face her as she buttoned me into it. The pyjama jacket had a ruffle neck that was fastened with two buttons at the very top. "No please," I begged pathetically. Miss Masterton and Aunty ignored my protests and merely continued adjusting the sleeves of the pyjama jacket that had elasticised cuffs.

"Step." Miss Masterton commanded as she held the pyjama bottoms at my feet. I put first one leg then the other into the pyjama bottoms. Miss Masterton slid the pyjamas up over my thighs and positioned them precisely on my waist. Using her hand she smoothed the brushed cotton material against my groin. I moaned slightly and she felt my excitement at her touch. Miss Masterton laughed and placed two fingers under my chin, raising my head and forcing me to stare into her face.

“Your nephew looks so sweet wearing his frilly pink floral pyjamas, I think I shall have to bring more pairs for him to wear." Her hand, masked from my aunt's view, continued to casually caress the brushed cotton of my pyjama bottoms in a manner that almost caused me to disgrace myself further.

"Please do," replied Aunty who inadvertently rescued me with the promise of a spanking. "He will be wearing frilly pink winceyette pyjamas for the foreseeable future so I will need plenty of pairs for him. Now, get over my lap, I’m going to deliver a smacked botty to you.”

I tried to protest but aunty only became angrier. She put me across her lap and moved me into her preferred position before removing her slipper and using it to administer an extremely painful spanking, so painful that I was reduced to tears and stood sobbing, ruefully rubbing my pyjamaed bottom as aunty informed me that my bedtime would immediately be changed from 7.30 and that my new regular bedtime would be 6.30. She then turned to Miss Masterton and asked her if she could think of additional punishments.

Miss Masterton paused for a moment before saying. "What if you were to bring him across to my house tomorrow at say 10 o'clock? He will be wearing his new pretty pink pyjamas, of course, we could get him to try on more of my pyjamas and I could pick a suitable pair for him to wear whilst he performed some household chores for me. You needn't stay. I would be  certain to bring him back in time for his new bedtime."

She smiled serenely as she spoke. "I may need to put him across my lap myself if his behaviour warrants, I trust that would be permissible?  Like you, I do so believe in maternal spanking's to persuade naughty boys to do as they are told"

Aunty enthusiastically agreed, adding that it was every females duty to regularly spank the males under their control. It was then decided to take tea outside and I was instructed to put on my quilted dressing gown and pink slippers.

The two ladies sat chatting in the pergola as I arrived with the tea tray and poured tea into the china tea-cups. One each for aunty and Miss Masterton. My plastic sippy cup containing warm milk stood incongruously alongside the silver teapot.

“Come here.” ordered my aunt as she unfolded the white towelling bib that also resided on the tray. My aunt positioned me with my back toward her and tied the humiliating baby bib around my neck. She took a sip of her own tea before pulling me onto her lap and presenting the sippy cup to my lips.

“There now, isn’t it better to be a good little boy and do as aunty says instead of getting smacked bottoms all the time?” I nodded compliantly as I swallowed my warm sleepy time milk, opposite I could see Miss Masterton smiling, obviously enjoying my embarrassing predicament.

Aunty snuggled me closer, tightening her grasp, she was almost nibbling my ear as she told me. “I think I will keep you dressed in Miss Masterton's, lovely soft winceyette pyjamas for a while yet until you learn to appreciate what a lucky boy you are to have such a loving aunt. What do you think Miss Masterton?”

“Oh yes, I think pink floral winceyette pyjamas are perfect garments for your nephew to wear, may I also suggest that along with his bib and sippy cup, you think about introducing him to night-time nappies and perhaps a baby’s bottle and also a dummy?” 

“What wonderful suggestions,” aunty replied.  Miss Masterton’s eyes had been fixed upon my face as she had made her suggestions and I realised to my horror that my aunt was going to let Miss Masterton have a big influence on my future.

My sippy cup emptied and aunty cradled me in her lap. As always happened after I finished my sleepy-time milk my eyes become heavy and I struggle to stay alert. 

“Never mind 6.30, 6 o’clock appears to be a more appropriate bedtime,” laughed aunty. “Let’s get you tucked into beddy-byes.” I drowsily kissed Miss Masterton night-night as aunty took my hand. Put straight to bed wearing my frilly, pink floral pyjamas with the looming prospect of nappies and baby dummies to look forward to, I wondered why I had ever married aunty.