Visiting My Headmistress

This account is of my first visit to my ‘Headmistress’.

I had been reported for misbehaviour and instructed to report to the her study. On entering, I was initially berated for having picked on Amanda (a girl in my form) to such an extent that she was desperately upset, and in tears. I was accused of having lifted her skirt, tried to pull her knickers down, and pulled her pigtails. Additionally, Miss Jones, my form teacher, had my satchel in which was one of Amanda’s pigtail ribbons. I protested that I had found it on the ground after I had been teasing her but was accused of stealing it – why hadn’t I handed it in to lost property ?

Headmistress now decreed that, having got poor Amanda into such a state by teasing her about her gymslip and attacking her, I should now find out what it was like to wear girl’s school uniform. Escorted by Miss Jones, I was sent to change – into blouse, navy gymslip, navy knickers and white knee-socks. Mary-Jane’s on my feet completed the ensemble and a very embarrassed Allan was taken back to the Head’s study.

Headmistress inspected me, straightened out the pleats of my gymslip and gave me a lecture on why gymslips were pleated. Completing her inspection, she and Miss Jones then enquired how Allan felt about being dressed in girl’s clothes ; whether he enjoyed standing there with a short skirt around his thighs. They informed me that, in a moment, Amanda would be invited to come and see me get my punishment. As I think a schoolboy in such a humiliating position would, I begged them not to let Amanda see me like this, but to no avail.

Anyway, there followed, initially, a session across Miss Jones’ lap for a thorough hand spanking. The slipper (actually a plimsoll), a leather paddle and a short strap were also used until Miss Jones eventually released me. I was sent to stand in the corner, hands on my head and eyes closed, whilst they discussed me and my conduct. Then Miss Jones left to fetch Amanda, and when they returned Amanda’s first question was “Why is Allan dressed in the girl's uniform Miss ? He looks cute” – just the sort of statement to embarrass a schoolboy in this situation. She was told it was punishment for how she had been treated. She sat down and was questioned on the circumstances of my having upset her whilst I continued standing in the corner.

After a while, I was summoned to the Headmistress’s desk. Here I was again berated for my treatment of Amanda and had to apologise to her. I mumbled "sorry" and was instructed to say it properly - and to curtsey to Amanda. I had to explain again that her hair ribbon, which had been found in my satchel, I had found on the ground and intended to return to her ; I was once more accused of having stolen it, or at least having intended to hold on to it as a ‘trophy’. Finally Amanda was told that, whilst I had been spanked by Miss Jones, I would now be spanked by the Head, and she could witness that – despite my pleas not to be spanked in front of her.

So it was back to the middle of the room and across the Head’s lap. Knickers down (in front of Amanda, despite my further protests), and, after she had inspected what Miss Jones had done, there ensued another lengthy spanking consisting of hand, slipper, strap, and wooden hair-brush. I lost count of how many spanks I received or how long it took. Amanda was apparently enthralled, making comments about how red my bottom was. Suddenly it was “Right, off you get” – with another dozen spanks for not moving fast enough ; since the Head only gave me half a second, this was grossly unfair, but I didn’t (dare) protest.

Finally, it was standing, gymslip up and knickers down so that I could be inspected – both by the Head and also by Amanda before she left us and I found myself in front of the Head’s desk again. Miss Jones reappeared. Before I received the final part of my punishment, however, it was decided that I should be made to change into a junior gymslip. This consisted of a short pleated skirt with a bib at the front and cross belts coming over the shoulders. I protested “Miss, you can’t make me wear that – it’s a Junior School uniform” ; this was rebutted with “you don’t deserve to be dressed in a senior uniform when you’ve been behaving as you have.” I was sent to change.

On my return, my further protests that the skirt was much too short – it didn’t even cover my knickers - were ignored. "It will make sure it doesn't get in the way," I was told. My clothing was adjusted, my skirt flounced and tie straightened. I was told off for my shoulder strap being twisted, and made to give the Head and Miss Jones a ‘twirl’ so that I could be fully inspected all around.

So, finally, it was across the whipping horse. Miss Jones started with a few hand-spanks, then gave me a dozen with a three-tailed tawse.She certainly knew how to wield it !! She finished off with a dozen strokes across the bottom of the buttocks with a very thin, whippy cane. That really stung !! Then it was Headmistress’s turn again. She commenced with what she called “the school spanker” – a wooden table tennis bat. That covered the cheeks of my bum thoroughly, and she moved on through various other implements including a strap and various paddles. Again I had no idea of how many spanks but eventually she stopped and brought out her canes.

She started with some strokes of the lighter cane – 18 strokes delivered in a quick, 'whippy' fashion which stung without being particularly painful. She then moved on to the heavy cane, starting with six good hard strokes across my bottom, then another six in rapid succession, all lower on the buttocks, at the top of the thighs. The effect of these, delivered without pause for breath, certainly took my breath away, and I think they were the nearest I had come to actually having tears in my eyes. At the same time, I was being reminded that this punishment was for how I had treated Amanda, and I was warned that if I didn’t behave myself Headmistress would dress me in a gymslip again and have several boys from my form brought in to witness my punishment. Naturally, I begged not to have her do that – I would never live it down ! But the threat remained. Finally, the Head gave me a further, final, twelve with the heavy cane at ‘normal’ speed, and then told me my punishment was over.

AllanBurns AllanBurns
61-65, M
4 Responses Dec 31, 2010

Nice, entertaining story, did you actually do this (in role-play of course)? I love role-play, I suppose it's the little boy inside me! I think I would "enjoy" trying out this scenario!

Absolutely ! "Amanda" and "Miss Jones" were each played by my Headmistress's assistant. I was originally dressed as per my avatar (that photo was taken at this particular session) and later "made" to change into the very short maroon bib and belt skirt. This was only one of our sessions ; unfortunately Miss C 'retired' about 5 or 6 years ago.

Great, I would have really liked your Amanda and Miss Jones, such a shame Miss C has retired!

Fantasic, i too love wearing a gymslip and being caned across my navy blue knickers

i would love to be cane over my school skirt just the feeling of bending over headmaster desk having my boottom cane over skirt then pull up skirt over panties

Very hot story<br />
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I'd love to be hand spanked over my school skirt - not sure I'd like to be caned though - ouch.