More from the archive of Pyjama Punishment Monthly

I thought you may be interested to learn how Timmy's petticoat education proceeded.
It had been arranged for Miss Healy to live in and tutor Timmy throughout the summer break. She was aware of Timmy's past, and, while she approved of my use of childish pyjamas to control his behaviour, she frowned upon him wearing male apparel however smart. Miss Healy advocated that Timmy would benefit by being dressed as a schoolgirl for tutoring purposes. She also suggested that he be confined to strictly girlish nightwear from the early evening. While not opposed to these ideas, I was at pains to point out my belief in an inexpensive approach to petticoat discipline. Miss Healy allayed my fears, accurately predicting that charity shops could provide our needs quite economically.
I must admit I enjoyed taking the reluctant Timmy shopping for his new wardrobe. Underwear was bought new; skirts, blouses, stockings and tights were all purchased second hand. I was particularly pleased when I spotted a delightful pair of brushed cotton pyjamas that were ideal for Timmy. They had been well laundered, but were incredibly soft and feminine. Pale green winceyette with a small white floral motif and a Peter Pan collar that buttoned to the neck. Timmy would look incredibly sweet in them.
Timmy's typical day would start with an inspection by Miss Healy, ensuring his schoolgirl uniform met her high standards. She insisted blouses be buttoned up to the neck, and that hemlines be just below the knee. A full morning of revision and written work would follow for Timmy until lunchtime. Timmy eats his meals sitting on his special 'low chair'; simply a shortened kitchen chair that ensures extra care is taken over table manners. A slapped hand or wrist is appropriate if something is spilled or dropped.
 Much to Timmy's distress, we took him for regular afternoon walks. Miss Healy believed petticoat discipline should be a humiliating experience, accordingly she would expose Timmy to possible ridicule by stopping inside a busy shop to fussily button up his cardigan, or noisily smack the back of his legs for failing to hold a grown-up hand near a busy road. Upon our return, Timmy would have further studies to concentrate on until it was time to put on his lovely soft girlish pyjamas.
Timmy's recent tantrums had been about his bed and pyjama time, Miss Healy was adamant that no concessions should be given, consequently, Timmy could find himself pyjama clad by five o'clock, or even earlier if inclement weather had prevented our afternoon walk. Miss Healy often liked to tease Timmy in front of the whist club ladies in order to humiliate him further. She would hold up his pyjama jacket like a matador's cape, swiftly pulling it away each time he tried to put his arms in the sleeves. Eventually she would slip it around his shoulders before slowly buttoning the jacket up to the neck. Then she would hold his pyjama bottoms out of reach above her head. Everyone found it extremely amusing to see him pleading to be allowed to put on his girlish pyjama bottoms, while making futile attempts to grab them, wearing just his pyjama top.
Miss Healy and I thought that Timmy would gain by learning how to sew.  His first challenge was to make and sew pom-poms onto his furry slippers. This he managed very well, and he seemed quite proud to show off his handiwork. Then I taught him how to work from a pattern and use a sewing machine. He produced a simple but very pretty cotton blouse that he wore with obvious pride. Rummaging around one day, I found a pattern for girl's pyjamas dating from the nineteen sixties, I decided these would be Timmy's next challenge. A remnant of pink, brushed nylon material was donated for the purpose and, with a little help from myself, an honourable result was eventually attained.
I decided that the finished garments deserved a special unveiling ceremony, so the next evening I took Timmy into his bedroom to dress him in his new pyjamas. The jacket, in true sixties fashion, had a laced ruff collar, frilled cuffs and a lace bodice. As I pulled up the pyjama bottoms, I realised Timmy had never worn brushed nylon before. Only now, as he began to squirm uncomfortably where the high collar chaffed his neck, would he begin to understand how we suffered as young girls, having to wear those wretched nighties and pyjamas that created their own aurora borealis when you took them off. I must admit to being quite pleased to see Timmy suffering in the same way.
 
Timmy's face was as pink as his pyjamas when I ushered him into view. Miss Healy had arranged the seating to imitate a catwalk. I marched him up and down the row of ladies, giving a commentary on the nightwear as I pointed out the finer points of his needlework. Then as the embarrassed Timmy stood awkwardly in front of us, I presented him with a crochet bed jacket to keep his pyjamas clean while he attends to his household chores. Timmy blushed uncontrollably as I tied it in place with ribbons and he buried his face in my lap as we all enjoyed his discomfort.
Miss Healy is set to leave us shortly but, as I watch Timmy dusting, wearing his pom-pom slippers, pink brushed nylon pyjamas, and crocheted bed jacket, I know I have her to thank for expanding my application of petticoat discipline, and ensuring Timmy continues to reap the benefits.