The Tale Of A Shirt’s Tails

By Endorphin


Copyright 2025 by Endorphin, all rights reserved

[2,265 words]

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This story is intended for adults only. It contains depictions of forced nudity, spanking, and sexual activity of preteen and young teen children for the purpose of punishment. None of the behaviors in this story should be attempted in real life, as that would be harmful and/or illegal. If you are not of legal age in your community to read or view such material, please leave now. 

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The Tale Of A Shirt’s Tails
By Endorphin

The Scene

It’s a hot and sunny June morning in 1966. At Saint Pádraig’s Grammar School for Boys in town of Ballycommon in Éire the boys are returning for the first day after the Half‑Term break.

The Tale

14‑year‑old Seamus McCartney had leisurely walked with his friends up the main staircase and turned from it onto the 2nd floor landing. He’d taken no more than a dozen steps towards his 3rd Form classroom, when Mr Findon, the Deputy Head with special responsibility for discipline, stopped him in his tracks.

The school had a strict policy regarding School Uniform, which the boys were required to wear smartly and correctly. Seamus was wearing his grey trousers properly fastened around his waist with a belt and totally hiding his blue and yellow striped boxers. His black formal shoes were shining (having been polished just before leaving home). Although they were hardly visible inside the trouser legs, his grey knee‑length socks were fully pulled up.

It being a fairly hot day, Seamus naturally wasn’t wearing the optional grey school pullover and, like many of his friends, he had taken advantage of a Summer Term waiver to leave his Blazer at home. This meant that his outermost garments, and the first things a teacher was likely to notice, were his shirt and tie. Fortunately for him, his tie was properly tied, with the front end neatly overlapping the slightly shorter one behind it. The neat knot was pulled right up and centred nicely between the two ‘wings’ of his shirt collar – there was nothing whatsoever about the tie to attract Mr Findon’s attention.

However the same couldn’t be said for Seamus’s shirt. “McCartney,” said Mr Findon, “Why are you wearing your shirt with its tails hanging outside your trousers in defiance of the school’s Uniform Rules, which require your shirt to be tucked into your trousers?”

“It’s too hot, sir, to have everything tightly tucked in, I need to let some air circulate,” replied the lad – hoping for some leniency on account of the weather.

“You know full well McCartney that we will not accept slovenly appearance when you are in School Uniform and an obvious ambassador for the school. Report to my Office at the start of Morning Break,” said Deputy Head, not willing to compromise in any way on the sartorial standard he expected of his pupils on behalf of the school.

At the start of the morning break, when he’d much rather be kicking a football around the playground, Seamus knocked on Mr Findon’s door but got no reply, so he stood in the corridor waiting for Mr Findon to return. After most of Seamus’s 15 minutes Break time had thus been lost, Mr Findon appeared and called Seamus onto his Office.

“Tell me again why you are not wearing your uniform correctly,” said the teacher. Seamus repeated that it was too hot and he wanted to let air circulate to his body to keep cool. “Well,” said the teacher, “We’d better make sure that you get plenty of air circulating over your body then.” As he opened a window he said, “Remove your shirt and tie, putting them neatly folded on the side‑table over there. Then come back to stand in front of me – Oh, remove your shoes too.”

Seamus hadn’t expected this but, somewhat bewildered, he did as he was told and soon returned to stand shoeless and bare‑chested in front of the teacher.

Mr Findon, who was now seated on a chair in front of his desk, reached forward and undid Seamus’s belt, followed by releasing the button and clip that still held the boy’s trousers up. As the zip fly was undone, gravity ensured that the trousers started their descent towards the lad’s feet, exposing his trendy underpants.

“That’s better now, isn’t it?” said Mr Findon, “There’s much more fresh air reaching your body now.” As he was saying this, he pulled Seamus over his knees, adjusting his position until the lad’s bottom was in a suitably raised position for chastisement. This quickly followed as Mr Findon’s hand made hard contact with the boy’s backside, protected only by his thin underwear – ‘SMACK!’

Seamus had only just fully appreciated the pain when the hand made further rapid contacts, well distributed over the two buttocks: ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ … ‘SMACK!’ As this was happening, Seamus was wriggling as much as he could to try to avoid the painful swats – but Mr Findon’s other hand was holding him down firmly.

Mr Findon instructed Seamus to stand in front of him again, with his hands on his head. Seamus thought that his spanking was over, but the pause was to enable Mr Findon to pull the boy’s underpants down so that they joined his trousers around his ankles. Mr Findon then turned round a bit and picked up a well‑(mis)used size 12 gym shoe from on his desk.

“Back over my knee,” was a command that Seamus really didn’t want to hear, knowing that the teacher’s target would now not even have the small amount of protection given by his thin underwear. No sooner was the lad in position than the shoe started raining down more fire onto Seamus’s gluteus globes: ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ Seamus’s legs were now waving around in the air and soon dislodged his trousers and pants onto the floor. The punishment continued unabated: ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ … ‘WHAP!’ Seamus was sobbing and calling for Mr Findon to stop, long before the shoe ceased to amplify the fire in the lad’s bum.

Mr Findon instructed the almost naked lad to stand before him again. “Pick up your trousers and pants. Fold them neatly and add them, with your socks, to your other clothes on the chair. You said it was too hot to wear your Uniform correctly; however, either you wear it properly or not at all. Since we must ensure that you can keep cool, as you say you need, you will remain naked for the rest of the school day. You can put your shoes alone back on to protect your feet. All your teachers will be informed that you are authorised, and required, to be naked today. Return here after classes to retrieve your clothes.”

As the task was completed, the bell rang to signify the end of the morning break and Seamus, humbled and totally embarrassed to be naked, made his way to his next lesson. Of course he’d been naked with his classmates in the showers after Gym, but to have to spend most of the day nude took him well out of his comfort zone. Then, of course, there was the matter of his well‑chastised backside. Being naked, all his mates could see it was bright red with the welts showing up as they turned to blue‑black bruises. Sitting on the hard plain wooden classroom chairs just added to his pain.

Lunchtime was even more embarrassing as it wasn’t only his classmates who could see his nakedness and know that he’d been thoroughly chastised – it was the whole school, including the teachers and kitchen staff, some of whom were female. He wanted to curl up and hide, but had to stay where he was.

Last period of the day was Gym. Seamus’s nakedness was even more obvious when he did star‑jumps, handstands, etc. as his well‑developed uncircumcised penis and testes bounced up and down almost seeming to shout out to all and sundry, ‘look at me – I’m naked!’

Seamus had hoped to be able to get his clothes from Mr Findon’s office and make a quick getaway when the bell rang, marking the end of school. However, the Deputy Head’s door was locked and the lad had to stand in the corridor outside as the rest of the boys piled by. Many applied a sneaky hand spank to Seamus’s exposed rump! Practically everyone else had passed him and left the school by the time Mr Findon returned. Seamus was pleased to be once again fully dressed! He made sure this time that his shirt tails were firmly tucked into his trousers before heading home and hoping that his father would never learn of this incident and punish him still more.

Unfortunately for him, his parents had already been informed (as was usual after any corporal punishment). Fortunately, when he was made to bare his buttocks for his father to see the ‘damage’, Mr McCartney only gave him one relatively light hand spank, saying that Seamus’s backside looked to have been spanked enough. However, he said, “Boys, including developing teens like you, don’t need excessive modesty. You are to spend the rest of the evening naked as you were at school.”

“But that means Vicky and Mum will see me and my exposed private parts – that’s not fair!”

His dad responded, “Your sister is now 13 and she needs to learn about a boy’s special parts. It’s not only fair but you must learn not to be so excessively modest, and it will be a good opportunity for her to see what a boy has ‘down there’. So, go to your room and strip off completely then come back down for your evening meal – and don’t try hiding your genitals.”

Seamus knew that if he tried to refuse, he’d still be stripped naked by his father – and be seriously spanked too! He tried to linger in his room but soon had to come down for his meal, very embarrassingly letting the womenfolk see the parts of his developing body that he kept so private.

After eating he had to help clear the table. Vicky watched intrigued as her brother’s penis bounced up and down as he walked. Soon the two of them were instructed to join their father in the living room.

Seamus was required to stand in the middle of the room with his hands behind his head so that Vicky could see and feel his whole body – ‘how terribly embarrassing and humbling for him!’

Mr McCartney hadn’t actually seen his son naked since he was just over 8 years old and able to safely take a bath without having to be supervised. He noted that the lad was already well developed for 14, with a long, plump penis and quite large testicles. He observed that Seamus’s foreskin extended well beyond his glans.

Vicky felt the muscles of her brother’s arms, which were well developed after much time spent in the gym. She ran her hands over his pert nipples, giving the teats a squeeze and pull (as a baby does when feeding from its mother – but more vigorously!). Seamus didn’t like that – it hurt as she roughly played with them!

Vicky, attention soon reached her brother’s genitals. This was the point where their father started describing his son’s genitals. Starting with the penis, he described how it has two uses, for urinating and for sexual coupling.

He went on to say that the skin at the end of it (called the ‘foreskin’) is designed to slide back when the boy is aroused, exposing the sensitive glans (or knob). He instructed the boy to pull it back, so that Vicky could see his glans. He noticed that Seamus struggled to get it right back over the rim of his plump glans. With the foreskin back in its normal position, Vicky was allowed to retract it for herself. She pulled it back rapidly, eliciting a shout of pain from her brother as the tight skin tried to stretch over the wide rim of the glans.

Vicky’s attention turned to her brother’s scrotum and testicles. She felt their weight and started rolling them about in her fingers. She wanted to know how solid they were and started to squeeze them. Seamus was soon screaming with the pain, as his sister’s grip on his most precious possessions tightened rapidly!

Vicky learnt a lot from being able to see and handle her embarrassed naked brother’s normally hidden bits. If truth be known, Mr McCartney also enjoyed being able to see all of his teen son’s body and how Vicky was able to learn from handling his privates. Seamus was just mortified to have had his naked body used like the sex education dummies that had been in use at school last year to teach the boys about their own bodies and puberty.

To complete Seamus’s embarrassment, his duvet was removed from his bed and he was instructed that he was henceforth to sleep naked on the bed rather than in it! What’s more, his father thought it would also be good for him to be naked all the time while at home in future – unless there were adult guests around – he would just have to be seen naked by his and Vicky’s friends.

Without telling his son, Mr McCartney soon started making secret plans for him to be circumcised, at the start of the school Summer holidays, to overcome the problem of puberty induced phimosis – that Seamus hadn’t even realised he had!

Had Seamus attended to tucking in the tails of his shirt that morning, he’d have been spared all of the indignities and also retained his foreskin, which he’d used to obtain great pleasure as he relieved his daily urges. Who would have thought that something as innocuous as shirt tails could cause such embarrassment and misery!

[The End]






   
   
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