Scott's Story - Part 10

As it turned out it wasn’t to be the only time Scott Harris found himself dressed in a sailor-suit. His mum had thought the outfit ‘charming’ on the occasion Scott had returned home with Emily after their visit to Miss Fairchild’s Emporium (See Scott’s Story - Part 9). To Scott’s utter dismay his mother agreed straightaway when Emily suggested to her that the sailor suit be bought for him to wear.

Scott was even more distressed when Aunty Violet made an unannounced visit and he was caught wearing his new costume. Aunty, however, was thrilled to see Scottie in the sailor-suit outfit. It was exactly as Scottie had thought on the way home, ‘just the sort of hideous outfit that would gain Aunty Violet’s enthusiastic approval’.

“Why it’s simply adorable!” she trilled, “Yes, Scottie must have it…”

Scottie was made to stand on a footstool so that Aunty Violet could properly examine what was to be the latest addition to Scottie’s humiliating new wardrobe. He reflected how earlier in the day, when he was in Miss Fairchild’s shop, he’d thought his new short-trousered school uniform was the most embarrassing outfit he’d been made to wear... until, that is, the sailor-suit had been produced. As he felt Aunty Violet’s fingers checking the seams and quality of the the stitching of his outfit, Scottie couldn’t help thinking he was wearing the wimpiest costume imaginable. He couldn’t think of anything that could possibly be worse.

Aunty Violet was most impressed by the little shorts. The sort of shorts, side-buttoned with no fly and no pockets, which might have been designed for an infant to wear and were now being worn by a boy of nearly sixteen, appealed to Aunty Violet’s sense of propriety.

“Proper boy’s shorts!” she pronounced, “… nice and short so their legs get lots of wholesome fresh air and sunshine… and no pockets to tempt naughty boy’s fingers to fiddle where they shouldn’t, isn’t that right, Scottie?”

Scottie blushed beetroot-red in front of his aunt. How did all these women seem to know exactly what he was thinking? It just wasn’t fair of them to think that all he ever thought about was playing with himself, however true it might be. But however much he did think naughty thoughts, he had very little opportunity to act on them these days, not since Miss Emily became his babysitter. If only he had not been put back into the Third Form… his own stupid fault, he knew only too well… but why had mum insisted on recruiting a thirteen year old girl to look after him?

It had all started off innocently enough; Emily would be given the front-door key to let Scott into the house after school. Scott couldn’t be trusted with a key, not since he’d managed to lose the one he’d been entrusted with. That incident necessitated mum having to pay for a new lock, an expense she was unwilling to risk having to make again. Within a very short space of time Emily managed to make herself indispensable... at least in mum’s eyes. Emily offered to stay in the house after school and make sure Scottie sat down and began his homework. She also started to make helpful suggestions on how to improve Scottie’s behaviour.

Mum and Emily got on like a house on fire and each new suggestion of Emily’s turned out to be a another step nearer the School Outfitter and Scottie’s humiliating demotion… to be put back into short trousers.

It’s hard to convey the trauma a boy such as Scott Harris endures when the privilege of wearing long trousers is withdrawn. There is nothing that quite compares to the right of passage a boy undergoes when he is allowed to wear long trousers for the first time. For boys it is a visible sign they are growing up and on their way to manhood. No longer will they have to display their smooth bare legs in public; no longer will it be assumed they are not old enough to do the thousand and one things grown-ups do. Wearing long trousers means gaining respect, not least respect from boys who are still not old enough to wear anything other than short trousers.

If an older boy like Scottie is observed wearing short trousers, it is fair to assume there is good reason for him to be so attired. Of course it could be nothing more than a mother’s desire to see her son smartly dressed and for lots of boys nothing is smarter than a nice brief pair of short trousers. So it would not do to assume a boy is dressed this way as a punishment for instance. It was never Emily’s intention to punish Scottie for his academic failure by suggesting that he be put back into short trousers. Her reasoning was to help Scottie improve his behaviour and to keep him out of trouble. Emily quickly found out all about the naughty boys Scottie had been associating with and simply saw that by putting him back into short trousers it would deter him from seeking out their company. As it turned out the last thing Scottie wanted was for his comrades in mischief to see him wearing short trousers and when they did catch sight of him wearing his extremely brief short school trousers they chased him and made it clear that if he was caught they’d debag him, throw him in the muddiest pond they could find and haul his little-boy short trousers up the nearest flag pole.

Events had culminated in Emily and Scottie visiting Miss Fairchild’s Emporium and his return home dressed in what was destined to become his sailor-suit. And as he stood quaking on the footstool in front of his Aunty Violet, Scottie couldn’t help but wonder what else the Fates had in store for him.

Scottie had every reason to worry about what other humiliations might be heaped upon him. Why, for instance, was Aunty Violet visiting? Scottie couldn’t remember her ever just ‘dropping in’ as she had just done. Aunty Violet’s visits were normally planned along the lines of a State Occasion… ever more reason for Scottie to feel nervous.

There was indeed a reason for Aunty Violet’s flying visit. Put simply she needed to vent her frustration on someone and as none of her usual outlets were available to her, she chose instead her sister Susan for that honour.

Aunty Violet began her exposition by making clear her views on those who let the side down and how she thought a special circle of hell should be reserved for anyone who lacked a sense of duty. All this was nothing new to Susan who had heard her sister rant on about the lack of moral fibre in the youth of today, but it put the wind up Scottie as he stood feeling very exposed on the footstool. Scottie couldn’t stop himself from fiddling with the hem of his ludicrously brief sailor-suit hot-pants, for which he was admonished by his aunt.

“Stop that fidgeting at once!” she bellowed, “If you can’t keep your hands still for two minutes, you’d be better off putting them on your head!”

It said a lot for Emily’s influence that Scottie, unsure whether Aunty Violet was actually ordering him to put his hands on his head, looked over at Emily for guidance. No words were needed and Emily merely nodded her head. Scottie lifted his arms up and clasped his hands behind his head.

Scottie was then left standing on the footstool with his hands up behind his head. He was subsequently completely ignored as his mum and Emily sat down to find out from Aunty Violet what had happened to cause her to visit her sister.

It appeared that a dear friend of Aunty Violet had a daughter, Penelope, who was soon to be married. Plans were far advanced and arrangements had been made, the church booked, the reception finalised and invitations sent out. There were to be four bridesmaids, each in identical outfits. The bride’s twelve year old brother, dressed in an outfit designed to complement that of the bridesmaids, was to be the ring-bearer.

“... but the whole thing has turned into a nightmare,” Aunty Violet said, with barely contained rage, as she explained how ‘the boy’ had contracted measles and had to be whisked off to a distant relative least he spread the infection and make matters even worse.

“He’ll be in quarantine for weeks,” Aunty Violet continued, “and won’t be able to attend his sister’s wedding… Penelope’s absolutely heartbroken… it’s completely upset her plans. So selfish of Simon to catch measles... now of all times… typical boy.”

Aunty Violet long held the view that boys of all ages were put on this Earth to irritate and annoy, so her undisguised lack of sympathy for Simon was nothing new to her sister Susan. Scottie’s mother held broadly similar opinions of the male species.

The considered opinion was that somehow Simon had managed to contract measles on purpose and that he did so with the express intention of shirking his duty. There were no words of comfort to be found for the boy.

Of course Emily understood completely how dispirited Penelope must have felt to have her wedding plans wrecked by her selfish younger brother. She expressed her sympathy and, after a few moments, thought she might make a suggestion:

“Couldn’t Scottie help?” she asked.

“Scottie help? In what way, Emily?” Scottie’s mum asked.

It has to be said that Scottie didn’t understand how he could possibly help either, so his mumbled question, “What can I do?” wasn’t so much an offer to help as a genuine query. However, the penny dropped for Aunty Violet and she kindly left it to Emily to explain.

“I think I can guess… I don’t know why I didn’t think of it m’self,” Aunty Violet beamed, “But... you tell them, Emily.”

“I thought that Scottie could take Simon’s place as the ring-bearer… that’s all,” she added modestly.

Scott felt as if he’d received a blow to the solar plexus. Take Simon’s place? Be the ring-bearer at Penelope’s wedding? Not likely!

“MUM!!” he wailed from his position atop the footstool.

“Quiet Scottie!” mum snapped, “We’re listening to what Emily has to say.”

“I’m sure Scottie would love to help out at Penelope’s wedding,” Emily continued, “You’d like to help, wouldn’t you Scottie?”

Scott was lost for words. It was all he could do keep control of himself and not lose his temper in front of everyone… besides, he knew very well where that sort of behaviour would lead! Instead he blustered and blurted out: “Yes… but… but…” Scottie didn’t get the chance to add, “... anything but a ring-bearer…” before Aunty Violet ignored him and got up another head of steam:

“Do you know, if Cicely hadn’t swanned off to Cap Ferrat, I’d have taken my woes to her and unburdened my problems,” she said,  “I’d never in a millions years have thought Scottie would be a suitable replacement for that selfish boy, Simon. Fancy getting the measles… why the wedding might have had to be postponed… but for Scottie. I’m really so grateful for your suggestion, Emily. Now everything can go ahead as planned. We just need to get Scottie round for a fitting, then there’s the rehearsal… Oh I can’t tell you what a weight off my mind it is…” Then, for the first time that Scottie could remember, Aunty Violet actually turned and thanked him. “You know Scottie, m’boy, you’ve done our family proud stepping in like this and volunteering your services as ring-bearer at Penelope’s wedding. When all seemed lost you stepped into the breech…” she paused as Scottie blushed with pride on hearing his aunt’s praise. Out of the corner of his eye he could see that Emily too was smiling proudly. “... of course, Simon is a few years younger than you Scottie, but I’m sure we’ll be able to squeeze you into his lovely little costume…”

Doubts quickly began to rain down on Scottie. Listening to the unexpected praise from Aunty Violet had so distracted him that he’d quickly forgotten that Simon was to wear an ‘outfit’. Scottie cleared his throat:

“Um… Aunty Violet… um, what type of outfit was Simon going to wear for the wedding?”

Aunty Violet beamed: “Why a charming little sailor-suit, of course!”

Scottie’s knees nearly buckled under him. A sailor-suit! Why a sailor-suit?! Why couldn’t it be something else, anything other than a sailor-suit?! Then Aunty Violet explained how Penelope’s ‘intended’, the groom, was a Naval Officer and that the whole wedding had been planned around a nautical theme.



Two days followed during which Scottie, perhaps unsurprisingly, tried his very best to wriggle out of his forthcoming rôle, but to no avail. Emily finally put her foot down and said she wanted to hear no more of Scottie’s silly nonsense. It was an honour, she told him, to be given the responsibility to walk down the aisle in front of all the assembled guests, leading the bride and her bridesmaids. He might even be allowed to give a little speech at some point in the ceremony. Scottie blanched at the thought. It was already giving him nightmares just thinking about walking down the aisle in Simon’s sailor-suit. How much worse could it get?

The very next day found Emily and Scottie at Penelope’s mother’s house for Scottie’s fitting. Scottie was smartly dressed in his school uniform for the occasion. Emily had even taken him to the barber’s shop for a ‘trim’. It was Emily’s idea of course, even though Scottie’s hair was already very short by comparison with all the other boys at his school. Mrs Bloom, Penelope’s mother, was most impressed when she was introduced to Simon’s replacement.

“My, but he is a smart young boy and short trousers too!” Mrs Bloom said, as she complimented Emily, “He’s a bit taller than Simon. How old is he?”

“Scottie’s fifteen years old… nearly sixteen actually,” Emily could see the puzzled look on Mrs Bloom’s face, so she went on to explain, “Scottie was put back a year at school and so his mother and I decided to put him back into short trousers as a sort of reminder for him to behave, buck his ideas up and work harder…”

“What an excellent idea… I must remember that for when Simon grows up,” Mrs Bloom said, “Any trouble and he’ll be put straight back into short trousers.”

Needless to say, Scottie was squirming with embarrassment at how he was being discussed as if he wasn’t there. What was even worse was the way Mrs Bloom looked him up and down as if he was a prize exhibit at the County Agricultural Show. Scottie half expected her to prise open his mouth in order to inspect his teeth.

“Good pair of legs… nice and smooth too…” Mrs Bloom observed and after noting how much standing about there’d be as part of the ring-bearer’s duties, she pronounced, “He’ll do…” She then lead the way through to the front-room where the fitting of Scottie’s costume would be carried out. As they did so the high-pitched giggling of four girls who’d been watching Emily and Scottie’s arrival from the upstairs landing could be heard. The girls dashed downstairs already dressed in their bridesmaids’ outfits. Scottie turned his head towards the giggling. He’d never seen so much pink in his life before.

But even the sight of the bridesmaids’ dresses didn’t prepare Scottie for the shock on seeing the ring-bearer’s… his costume.

Laid out neatly on a table in the front-room was an unbelievably brief sailor-suit outfit… briefer even than the one Scottie had worn. It looked as though it would barely have fitted the twelve year old Simon, let alone fifteen year old Scottie. But that aspect of the ring-bearer costume wasn’t the first thing Scottie noticed. What was impossible to miss was the outfit’s shade of shocking pink. Like the bridesmaids’ dresses, the ring-bearer outfit was liberally detailed with little bows and nautical touches, but it was hard not to be overwhelmed by the outfit’s overall pinkness.

Scottie, once he felt able to speak, whispered to Emily: “I thought it was supposed to be a sort of navy wedding… sailors wear blue don’t they?”

“Oh yes,” Emily replied, “the sailors will be wearing blue, but the girls will be wearing pink.”

“But I’m a boy… I should be wearing blue…”

“No Scottie, you’re not a sailor, you’re going to be the ring-bearer… that’s different,” Emily explained, “You see Scottie, the ring-bearer is what’s called a ‘supporter’, part of the bride’s escort… like the bridesmaids. Penelope wants the bridesmaids dresses to compliment her wedding dress and the ring-bearer’s costume to compliment the bridesmaids… I’m sure you understand that.”

Scottie did not understand. No matter how well Emily explained things, Scottie couldn’t understand why he had to be dressed up, all in pink, like a sissy.

Before Scottie could say anything else to Emily, Mrs Bloom stepped in to speak to Emily and again ignored Scottie: “I do hope you like the ring-bearer costume Scottie will be wearing…”

“Yes, it’s lovely, Mrs Bloom,” Emily replied, “I was just explaining to Scottie how you’ve themed the outfits and he’s really looking forward to trying it on, aren’t you Scottie?”

Scottie would have exploded with indignation hadn’t he had the eyes of four bridesmaids, Mrs Bloom and Emily upon him. Feeling how this was possibly the most unfair thing that had ever happened to him, Scottie was nevertheless compelled to meekly reply that, yes, he wanted to try on the humiliating pink sailor-suit.

“Better get him undressed then, hadn’t we?” Mrs Bloom said as she turned to Emily, “Would you mind…?” indicating that her help was needed. To his horror Scottie found out that his fitting was to take place in front of the giggling girls right there in Mrs Bloom’s front-room. And this would also involve him being stripped bare-nude!

It seemed as if Scottie would never be afforded any privacy as Emily and Mrs Bloom started to undress him. When he did protest no sympathy was forthcoming.

“Oh don’t make such a fuss, Scottie,” Emily chided him, “We have to get you undressed so that you can try on the costume Simon would have worn…”

Mrs Bloom, who was clearly very experienced in getting young boys out of their clothes, soon had Scottie’s school blazer off along with his tie. She then unbuttoned Scottie’s grey school shirt while Emily started on Scottie’s school shorts. Before he knew it, Scottie was standing in the middle of the room dressed in nothing more than his white school vest and junior boy’s underpants. No one seemed to mind the girls being there… only Scottie who was blushing a fire-engine red. When he asked if the girls were staying he was told how they had come and changed into their bridesmaids’ dressed especially. This was so Mrs Bloom could see Scottie, once fitted in his ring-bearer costume, and the girls together to make sure everything was in order.

But why, Scottie wondered, do the girls have to be here while I get changed?

“Oh do grow up, Scottie… nobody is in the least concerned about seeing you with no clothes on,” Emily said as she pulled Scottie’s vest out of the elasticated waistband of his underpants.

It was at times like these that Scottie had difficulty in remembering that Emily was only thirteen years old, very nearly three years his junior. But as he didn’t want to risk a scolding from Mrs Bloom, who looked as if it wouldn’t take much for her to lose her temper with him, Scottie stood still while Emily peeled off his school vest and then eased down his underpants right in front of the four bridesmaids.

There followed much talk about the ring-bearer’s little costume and Scottie was made to wait as he stood in his birthday suit in the middle of the front-room. When the costume was held up for everyone to admire… everyone apart from Scottie that is… he saw that it was even worse than he thought. The violently pink hot-pants style sailor-suit shorts were actually trimmed with tiny lacy hearts and arrows. The buttons at the side of the shorts were heart-shaped with little anchors inset. There was lace trim everywhere and the sailor hat, which Scottie was to be allowed to wear in the church, was embossed with the words ‘HMS Cupid’.

The cushion upon which the rings would be carried, was itself a model of cuteness. The word ‘love’ was embroidered on it in a number of prominent places and of course it was made of the same pink satin material from which Scottie’s costume was made.

The girls thought it was going to be so cute to have Scottie walking down the aisle in front of them. They couldn’t wait for the ‘big day’ and at that moment Penelope walked into the room. Without bothering to acknowledge Scottie’s nudity, she looked him up and down.

“Is this Simon’s friend?” she asked, “The boy who’ll be taking my brother’s place as ring-bearer?”

“This is Scottie,” Emily informed Penelope, “He’s agreed to stand in for Simon at your wedding. We were just getting ready to let Scottie try on the ring-bearer’s outfit, so you’ve come at the right time.”

Scottie was so desperate to put matters straight, but nobody was listening to him. He didn’t know Simon… as far as he was aware he’d never even met him. He certainly did not agree to take Simon’s place, leastways not in the way Emily implied. It was Aunty Violet and Emily who between them had badgered him into ‘volunteering’. But nobody was interested in what Scottie thought and everybody ignored him, as if having a totally nude body standing in the middle of the front-room was an everyday occurrence. Mind you, thought Scottie, if this is the sort of thing Simon has to put up with, it’s no wonder he managed to get measles… I wonder how he did it, Scottie pondered.

“Scott… Scott Harris, stop day-dreaming and come over here,” Mrs Bloom called. It was time for Scottie’s fitting.

“We thought underpants would ruin the line of the shorts,” Mrs Bloom explained to Emily, “So we didn’t intend to have Simon wear any… would be alright with you if we took the same approach with Scottie?”

“Of course that will be fine,” Emily replied, “Scottie has a sailor-suit of his own and he’s not allowed to wear underpants with that… in fact he’s not allowed to wear underpants with any of his play-clothes, are you Scottie?”

Scottie managed to croak out a reply in the affirmative. He was by this time wishing Emily and Mrs Bloom would just get on with things.

“Are you sure the costume is going to fit, mum?” Penelope asked.

“I’m afraid it’s going to have to fit, Penelope. We haven’t time to make alterations at this stage.”

The pink sailor-suit top was the first part of the costume to be tried. It did not auger well for the rest of the costume, but the only significant problem was that Scottie was a taller boy than Simon, consequently the top only just reached Scottie’s tummy-button. No matter how much the top was pulled, it couldn’t be stretched any further. Unperturbed, Mrs Bloom and Emily carried on with the fitting and made Scottie step into the sailor-suit hot-pants-style shorts.

“Careful, Scottie!” Mrs Bloom scolded him when his heel caught on the tiny shorts.

Between them and with a bit of extra help from Penelope, Mrs Bloom and Emily drew the little pink sailor-suit shorts up Scottie’s legs.

“Just as well Scottie’s got such smooth legs,” Penelope remarked.

It was certainly also just as well the little shorts were side-buttoned. It made it easier to deal with Scottie’s boy-bits.

“He’s a bit more developed than Simon…” Penelope observed.

“Scottie’s nearly sixteen apparently,” Penelope’s mother informed her daughter.

“Good lord… well I never would have thought it… I mean, by the looks of it Scottie hasn’t even got a single pubic hair yet!” Penelope replied and then casually took hold of Scottie’s penis prior to squashing it into the tiny shorts, “What do  you think I should do with his thing… up, down or sideways?”

“Winky?” Emily interjected.

“Winky?!” Penelope guffawed, “Winky! Are you sure he’s nearly sixteen?”

At this remark the bridesmaids who were watching the proceedings, started to giggle again and voice their suggestions was to which way ‘winky’ should be placed in the sailor-suit shorts. One of the bridesmaid even went so far as to help Penelope position Scottie’s penis… pointing downwards.

Amid much pulling, squeezing and pushing, Mrs Bloom, Penelope and Emily and with the occasional help from one of the bridesmaids, Scottie was finally fitted into the little pink sailor-suit shorts. The satin material of the shorts showed every crease and bulge and clung to Scottie like a second skin. It felt most uncomfortable, but Mrs Bloom was pleased with the result.

Next Scottie was helped into a pair of knee high white pelerine socks. The ribbed design featured tiny anchors intertwined with hearts and Cupid’s arrows. Shiny pink, single-strap maryjane shoes were considered to be the only footwear that could complement the rest of the ring-bearer outfit and these were duly fitted. They were a little tight for Scottie, but Emily assured him they would stretch a bit if he wore them for a few hours each day before the wedding. Scottie was finally helped into a pair of white lace gloves and the ‘HMS Cupid’ sailor’s cap placed on his head.

The girls thought the ring-bearer outfit looked cute; to Scottie it was simply a shameful symphony of sissiness.

Scottie was then presented with the ring-cushion and told how to carry it with his arms outstretched. The muscles in Scottie’s arms quickly started to ache, but Penelope insisted this was how Scottie was to carry the cushion down the aisle. Scottie was told to walk around the room and scolded for dragging his feet.

“Lift your feet up, Scottie… You’ll ruin the whole ceremony if you scrape your lovely shoes.  That’s it lift your knees up nice and high… yes, that’s it… Do you think you could get Scottie to practice his walk, Emily?”

Emily agreed to make sure Scottie got plenty of practice.


Back home and for once relieved to be back in his school uniform, Scottie, still somewhat shocked and overwhelmed by the awful pink, sissy outfit, actually begged Emily to let him wear the sailor-suit that had been bought for him from Miss Fairchild’s Emporium. He knew there was no getting out of being the ring-bearer at Penelope’s wedding… his Aunty Violet would see that he did his ‘duty’… but did he have to wear that awful, humiliating pink costume?

“Please, Miss Emily… please don’t make me wear that outfit again,” Scottie pleaded.

“It’s not up to me, Scottie,” Emily replied, “... and besides, even if it was up to me, I’d still expect you to wear it…”

“... but it’s not fair!” Scottie blurted out almost in tears, “It’s a sissy outfit and everyone will laugh when they see me wearing it at Penelope’s wedding!”

“No they won’t, Scottie… It’s a nice outfit… and the ring-bearer is very important,” Emily said in an effort to console Scottie, “When the congregation hears the ‘Wedding March’ everyone will turn around and all eyes will be on you Scottie, as you walk down the aisle at the front of the procession, carrying the cushion with the wedding rings. Simon will be so disappointed he was ill and couldn’t be the ring-bearer. When he sees the wedding photos…”

“Wedding photos…?” It hadn’t occurred to Scottie there would be evidence of his humiliation.

“Yes, wedding photos, Scottie… of course there’ll be wedding photos.”


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