The Memoirs of a Boy - Part 5

 

After the hairbrush spanking administered by Miss Mary’s mother, Mrs Fletcher in the front room of their house, it finally dawned on me there was simply no way out of my predicament. I felt so ashamed of myself that I was quite unable to even approach, much less peek over the wall of guilt and disappointment which I had built up and that now surrounded me. I was truly trapped within the confines of this self-made rampart.

That night as I had lain in my bed, a sad and sorry boy, the tears trickled onto my pillow. I had tried to do my best, but clearly my best was just not good enough for Miss Mary. She had shown her trust in my progress by allowing me to demonstrate to her mother how much I had learnt under her tutelage, but I had let her down. I realised my clumsy behaviour would have consequences, but I never for one moment considered the prospect of my being spanked with a hairbrush, bare-bottomed over Mrs Fletcher’s lap. 

I had become conditioned to receiving sharp smacks from Miss Mary to my bare thighs for my multitudinous failings and so fully expected to feel my legs being warmed up yet again. In the few brief moments before Mrs Fletcher spoke to my mother on the telephone it had passed through my mind how humiliating it would be for my bare legs to be smacked by Miss Mary in front of her mother. With this in mind you might imagine how I felt when my naughty shorts, as Miss Mary had christened them, were pulled down by Mrs Fletcher prior to my being taken over her lap to have my bottom spanked with a hairbrush. Shocked isn’t the word. All I was wearing underneath my shorts was a boy’s support thong, the thin strap of which pressed deep between my buttocks, leaving the cheeks of my bottom quite bare. The only saving grace was that wearing the thong meant that at least I was spared the further indignity and humiliation of revealing my private parts to them both as I was made ready for my spanking.

It’s hard for me to explain why I so readily came to accept Miss Mary’s authority, but if I was ever asked to define my philosophy I would say that it was to do anything for a quiet life. Was that so wrong of me? 

Take the continuing enforced wearing of short trousers. If I tried to draw my parents attention to the fact that most, if not all of my contemporaries were to be seen in long trousers; or heaven forbid that I should complain or moan that I was still dressed in short trousers, this would be seen as proof positive that I was still too immature to be allowed longs, since in their eyes a strong, fit boy would take these clothing restrictions in his stride. In other words a mature boy would just get on with it; he wouldn’t whinge or complain as I was doing.

I think I must have first put forward my argument for long trousers sometime around my thirteenth birthday, perhaps in the delusional hope that I would receive a pair of longs on the day, or at least soon after I became a teenager. At this stage my request was politely ignored and I was left to ponder on life’s inequalities as I sat bare-legged in a class full of long-trousered boys, made constantly aware of this fact by the feeling of the hard wooden seat against my bare thighs. 

Within a few months, there being no sign of a change in my mode of dress, I pressed my case for long trousers once more only for it to be brushed aside and to be told that I didn’t need them. No other explanation was forthcoming and again I was left to stew in my own juices. At school I became something of a laughing stock, especially among long trouser wearing younger boys who thought it great fun to mock me, calling me names and even vying with each other to get close enough to my bare legs to deploy the age-old fiendish schoolboy weapon of the elastic band, stretching and snapping it against the flesh of my exposed legs. The boys would cheer when one of their number scored a direct hit, which not only stung as if I’d been attacked by an angry wasp, but left visible a sore red mark for everyone to see.

My parents must have noticed the results of these schoolboy pranks but thought nothing of it. I wouldn’t be at all surprised to be told they had assumed it was some sort of silly game played by young boys like me. So of course their view with regard to my clothing remained unaltered; I was still not yet old enough to be promoted to long trousers. 

So to me the reason I remained in short trousers appeared to be simply that of my age, but as my fourteenth and fifteenth birthdays came and went, it became apparent the stance of my parents had changed subtly. From then on I sensed the continued presence of short trousers as part of my daily apparel was because of my perceived immaturity. Whenever I tried to raise the subject; that I was now surely old enough to be allowed long trousers, one or both of my parents would, as I have said, interpret my requests as continuing proof that I was still far from mature enough to live up to the responsibility as the wearing of long trousers would, in their view, entail. It seems obvious to me now that it was the belief of my parents that boys, once promoted to long trousers, would be expected to discard the attributes of boyhood. From their perspective it was therefore no doubt seen as a kindness for them to keep me in short trousers.

And so this in many ways explains my acceptance of Miss Mary’s authority over me. You see I had reached the conclusion that the only way I could hope to convince my parents of my maturity was to accept my status; that being what can best be described as a junior boy. I resolved that no longer would I begrudge their strictures. I would, as far as I was able, consent to my strict clothing restrictions no matter how humiliating it was for me to be seen bare-legged in public. 

The continued wearing of short trousers meant that I was also subject to various restrictions in keeping with my status about which I have written previously. Rules such as early bedtimes along with the need to be constantly supervised and kept busy to prevent mischievous behaviour were part and parcel of my teenage years. These measures of course accounted for the banishment to my bedroom during those evenings when mother and father entertained their guests in our house.

Needless to say my attempts to appear as a mature teenage boy ready to be granted the privilege of wearing long trousers came to the most ignominious end. As a result of Miss Mary finding me out of bed, prostrate on the landing at the top of the stairs trying to eavesdrop on the party given by my parents downstairs, I became beholden to her when she agreed not to say anything to my parents about what I had done. The rest you know: how, after all my hard work for which I received good grades in my exams, I was finally rewarded with my first, and as it turned out last, pair of longs. With pride I wore my newly sanctioned long trousers only to be told, not more than two weeks later, to beg my parents to be kept in short trousers. This was to be Miss Mary’s reward for supervising me during numerous study sessions held at her house.

It is little wonder that mother was upset by my rejection of their decision to allow me to wear long trousers. Although hardly unexpected, her reaction hurt. Not only had I been forced to reject their concession, my longed for desire for a pair of proper boy’s long trousers, but in the process I had brought upon mother the indignity of her having proudly explained to family friends that I was at last a boy mature enough to be allowed long trousers, only to find out that she was wrong. In her view I had behaved like a spoilt little boy who throws his toys out of the pram.

Now that I had rejected the opportunity to at last wear long trousers, I was faced a future of indeterminate length constantly dressed in thigh-baring short trousers. I really didn’t think matters could get any worse, but of course they did. Somehow Miss Mary had arranged for me to work throughout the long summer holidays in a café run by the mother of one of her friends. 

There I was, under the impression I would at last have some time to myself, blissfully ignorant of what was in store for me. Gone then was the opportunity to hide hide myself away so that as few people as possible could see me wearing the short trousers I found so humiliating. Then all of a sudden it was revealed to me that I was to work in a well frequented café. In such a place there would be no escape; everyone would be able to see that I still wore short trousers.

It seems as if I was the last person to find out what I’d been signed up for and that only happened when Mrs Fletcher let the cat out of the bag after I’d dropped a cup and saucer at her feet. It was my reaction to this unexpected news that resulted in my hairbrush spanking in front of Miss Mary.

Miss Mary claimed it was to be a ‘surprise’ for me. Well, it certainly was a surprise, although not in the way I suspect Miss Mary had intended it to be. Did she really think I’d be thrilled to have my summer holidays ruined? Or perhaps she knew what my reaction would be and relished the opportunity to be involved in humiliating me further? But I realise it would be foolish of me to try and understand her motives. No doubt she thought she was doing it for the best and in that respect I am sure she had the full support of my parents.

Shortly after my unexpected appearance over Mrs Fletcher’s lap for a spanking I was introduced to Miss Mary’s friend Rebecca. It had been decided that Rebecca would interview me on behalf of her mother who ran the café. I think I’ve made it plain enough already that I didn’t want this summer job in the first place and of course it had crossed my mind for me to be as uncooperative as I dared. But in the end it didn’t really matter how I presented myself to Rebecca. I think all she wanted was to see what I looked like and maybe to confirm that, yes, I was still kept in short trousers.

It was mother who ‘suggested’ I wear my short trouser suit for the interview. This was, and still is, a bespoke suit made for my fifteenth birthday with shorts, while not quite as short as my grey pull-up naughty shorts, were nevertheless still somewhat shorter than my school shorts. The shorts of this suit were held up by trouser braces which, when adjusted properly by mother, meant that my shorts were pulled up nice and tight at all times. Of course that was when I was fifteen and I’d since grown some more, so you can imagine how extremely short they looked on me at the age of seventeen. The suit came with a ‘bum-freezer’ jacket, the style of short jacket that barely reaches the waist of the wearer. Bum-freezers are very close in style to the jackets of ‘continental’ suits so popular for boys a few years back. The colloquial name given to the jacket is because the seat of the trousers is fully displayed, leaving boys such as me wearing short trousers feeling more exposed than ever. The jackets seemed to simply draw attention to the ridiculous brevity of the wearer’s trousers. 

Of course in accordance with mother’s wishes I wore my all too brief short trouser suit for my introduction to Rebecca. 

I was soon to learn how to  properly address her. In fact that was the first thing that Miss Mary made known to me as she invited me to, “Say ‘hello’ to Miss Rebecca.” I couldn’t help but notice conspiratorial glances pass between them.

“Well I’m pleased to see you so smartly dressed, Georgie.” My heart sank when I heard Miss Rebecca address me using the form of my name that so far only Miss Mary had used. My subservient rôle was thus quickly established. “You’ll be given a uniform to wear,” she added.

“What do you say, Georgie?” Miss Mary prompted.

I looked from one to the other and back again. I was pretty sure what Miss Mary wanted me to say. I felt a fool saying it, but I said it anyway.

“Thank you, Miss Rebecca.”

Of course now I was left wondering what this uniform would be like. I tried to put a positive spin on matters by telling myself that at least I would be wearing long trousers, as I couldn’t imagine Miss Rebecca’s mother would for one moment countenance a boy working in her café dressed in short trousers. I didn’t dare ask if this would be the case.

Miss Rebecca then started to look me up and down. She walked around me making no attempt to disguise the fact she was examining me closely, paying particular attention to my short trousers. It was most unnerving. Miss Mary kept a steady eye on me and urged me to stand up straight, something I thought I was already doing.

It was inevitable that worse was to come and that another of my hopes would be dashed.

Miss Mary spoke: “Tell Miss Rebecca what you told your parents, Georgie.”

Miss Rebecca looked quizzically at Miss Mary, clearly keen to hear what this was about. She might not have known, but I did. I was loathe to reply and reveal what I had said to my parents.

I ummed and ahhed until Miss Mary spoke again:” Come on, Georgie, we haven’t got all day. Tell Miss Rebecca what you said to your parents.”

There was nothing for it. I was forced to tell Miss Rebecca that I had told mother and father that I did not want to wear longs, that wished to remain in short trousers.

Miss Rebecca let this news sink in for a second or two before speaking: “Oh, so that’s why you’re wearing a short trouser suit! I had wondered why a boy your age was still wearing shorts.”

This interview was turning out to be even more shaming than I imagined.

Miss Mary added more fuel, stoking the flames of my embarrassment: “Yes, Georgie much prefers to wear short trousers, don’t you Georgie? His mother even bought him a pair of longs, but he didn’t want to wear them, did you, Georgie? She was most upset and very annoyed with him,” she explained to Miss Rebecca.

Even though it was not true that I preferred to wear short trousers, I was still forced to agree with Miss Mary for reasons that I’m sure you are by now fully aware. 

Miss Rebecca thought for a moment. Ignoring me she spoke to Miss Mary: “Well, I’ll have to speak to mum about this. Personally I can’t see there will be a problem for Georgie to wear short trousers at the café… I mean there shouldn’t be any health and safety issues if Georgie insists he has to wear short trousers…”

I wasn’t sure about health and safety regulations or how they could affect the way I was dressed, but from my experience with mother I knew what a handy target my bare legs would be if my work at the café wasn’t of a sufficient standard.

I ventured to offer a compromise: “I - I don’t mind wearing long trousers at the café… honestly… I mean I don’t want to cause a problem…”

Miss Mary scotched that idea straight away: “Don’t be silly, Georgie. What would your mother think if you suddenly started to wear long trousers after you told her you didn’t like wearing them? I think she’d be even more upset with you than ever.”

Miss Mary was perfectly correct. The thought of how mother would react if she saw me dressed in longs didn’t bear thinking about. I kept quiet about long trousers and the subject was not mentioned again.

Miss Rebecca decided to take me along to the café to meet her mother in order to obtain her approval for my employment. Two things crossed my mind. The first in which I had wishfully thought Miss Rebecca’s mother, Mrs Cable, would decide that I was not suitable was quickly followed by the thought that, well, at least I would be earning something for my work. As I warmed to this thought, the idea occurred to me that I might even be able to save enough to buy myself a pair of long trousers, even though I would undoubtedly have to wear them in secret. At this last thought I brightened up a little. Maybe working at the café wouldn’t be so bad after all.

I was wrong on all counts.

Mrs Cable was perfectly happy to have me work at the café during the busy summer months. However, she then went on to explain that I would be receiving something she called ‘work-place experience’ and for some unfathomable reason which I did not understand, I would receive no remuneration since this was not classified as paid employment.

She continued, “... but you may receive tips from those customers who wish to reward you for your service. These are put in a pool and shared out with the girls at the end of the day.” The 'girls' being the waitresses Janet and Judy. 

My hopes that I might be able to buy myself some longs having been scotched by the news that I would not be paid, rose again only to be dashed moments later by Mrs Cable’s next words: “Your share of the tips will be put towards the cost of your uniform… and since you insist on wearing short trousers I have been told by the catering suppliers these will be a one-off and therefore more expensive than a regular outfit.”

I almost had to bite my tongue when I heard this. I so wanted to tell Mrs Cable how I would gladly wear a regular uniform, but Miss Mary’s warning of what my mother’s reaction would be prevented me from saying anything.

I didn’t realise it at the time, but this arrangement by which the tips given to the staff were shared did not go down at all well with Janet and Judy. They were quite happy with the current arrangement for dividing the tips between the two of them. Now they would only be getting a third of the pooled tips instead for half each, so you can imagine how my arrival on the scene went down with them. They resented my presence from day one..

My work at the café was closely watched by Miss Rebecca. I was given a name-tag on my first day. My heart sank as I saw the name ‘Georgie’ printed on the plastic card. Now more people would be calling me by a name so closely associated with my status, a status that I could only think of as that of a ‘junior boy’. There didn’t seem to be an end to my humiliations. I reflected on the events of the past few months and tried to work out how my life had taken a turn down this awful path. Sure, my parents had always been very protective and this manifested itself in my being kept in short trousers far beyond the age at which teenage boys would normally be seen wearing them. My introduction to Miss Mary had certainly been a major event and before I knew what was happening, she had skilfully ensured that I, who I have to remind you is two years older than her, became subservient to her wishes. There didn’t seem to be any way out of my plight, but what sealed off any exit from the mess I was in was my own stupidity, being caught by Miss Mary doing something I was foolish enough to think would not be discovered.

It was simply one thing after another and now I was to be a short-trousered waiter at the café run by the mother of Miss Mary’s friend, a girl, Miss Rebecca, who was about the same age as me. The badge was yet another reminder of my junior status. The uniform itself made me even more self-conscious than ever. Sure, I was given an apron, but it was so small as to be hardly worth the effort of putting it on. The apron barely reached the tops of my thighs and wasn’t large enough to cover my bottom at all. Because the little shorts they provided for me to wear were so short, the effect was make it seem, when viewed from the front, that I wasn’t wearing any trousers at all. This just encouraged customers to poke fun at me before insisting I turn round so they could see if I was indeed wearing anything. This gave them a splendid opportunity comment upon my bottom which was encased in the snuggest little shorts Miss Rebecca’s mother could find courtesy of the catering clothing suppliers.

It will come as no surprise I’m sure when I tell you that my mother became a regular habitué of the café. And it wasn’t long before my bare legs felt the sharp sting of one of her well-placed hand smacks. I have forgotten the reason, but this public admonishment by mother gave the green light to other customers who were dissatisfied with my service to use the same method as her to show their disapproval. It wasn’t long before I was leaving the café each evening with my thighs glowing red.

Family Values - Pyjama-time

The well brought up boy should follow a daily routine to keep him fully occupied and prevent the sort of mischievous behaviour that so often lands them in trouble. A boy’s pyjama-time is an important aspect of this regime, part of the formal structure of his day. In some households pyjama-time has become something of a ritual during which the boy is made ready to be put into his pyjamas by being undressed in the family room at a set time of the day. Whether or not there are visitors present it makes no difference and the preparations for the boy’s pyjama-time proceed as normal.

Thirteen year old Oscar is one such boy who, even though he thinks that now he’s a teenager he should be allowed to put on his own pyjamas, is still subject to what has lately become an increasingly embarrassing routine. Mummy continues to get Oscar ready for his pyjama-time in the same way as she’s always done ever since he was a little boy. Even now that he has begun to enter puberty Oscar is still undressed in the family room. Mummy isn’t at all bothered if one of her neighbours has popped round for a gossip. If it’s Oscar’s pyjama-time, she sets about getting her son undressed and ready to be put into his pyjamas just as she’s always done.

One day Oscar returned home from school to find mummy having a cup of tea in the living room with their new neighbour who had called round to introduce himself.

“Come and say ‘hello’ to Mr Wheeler, Oscar,” she told her son, “He’s just moved in next door.”

Oscar dutifully did what he was told and went to stand in front of the neighbour before offering his hand to shake with Mr Wheeler.

“What a polite young boy you have, Mrs Pipe,” Mr Wheeler said turning to Oscar’s mother. “And I might add a very smart young boy as well. It’s not often you see a boy dressed in proper school trousers these days.”

Mummy smiled: “Oh, you mean the short trousers Oscar is wearing? We try our best, although Oscar’s not above complaining… he’s been pestering me for a pair of long trousers like some of the boys in his class wear to school,” she explained.

Some? Oscar blushed. That was unfair, he thought.  All of his classmates wore long trousers! The subject of Oscar’s school trousers was a sore point with the thirteen year old. Oscar thought he should have been promoted to long trousers ages ago; none of the boys in his class at school wore short trousers any more. Maddeningly though his mummy always told Oscar there was plenty of wear left in his short trousers and she didn’t see why he shouldn’t continue to wear them. Unfortunately a couple of growth spurts didn’t help Oscar’s cause; that he was old enough to be allowed long trousers. Mrs Pipe pointed out that if she had promoted Oscar to longs, she would have had to buy him new trousers each time his legs grew a bit longer, whereas he could happily carry on wearing the same pair of short trousers however long his legs got. Mrs Pipe might also have added that she thought her son looked so cute and adorable wearing short trousers that she’d had them all specially altered to be as thigh-baringly short as possible, but she was far too discreet to admit it. He’s got such lovely legs, she would say to herself, it’s a shame to cover them up.

“Mummy tells me you’re in the Boy Scouts, Oscar,” Mr Wheeler said to the boy whose face turned a slightly deeper shade of pink. Oscar was a shy boy and always felt nervous when a grown-up spoke to him in expectation of an answer.

When Oscar failed to reply Mr Wheeler smiled: “What? Cat got your tongue? When I was your age I couldn’t wait to get changed into my Boy Scout uniform, especially when our patrol was going to be camping out.” He paused before adding brightly, “Tell you what, why don’t you go and get your Boy Scout uniform to show me and I’ll tell you if it’s like the one I used to wear.”

It was mummy’s turn to smile. She thought it was a splendid idea and told Oscar to take Mr Wheeler up to his bedroom and show him his Boy Scout uniform.

Oscar led the way upstairs and along the landing to his bedroom. They went in and Mr Wheeler looked around the room as Oscar opened his wardrobe and pulled out one of the drawers where his scout uniform was kept. Oscar’s single divan bed was covered with a candlewick bedspread on top of which Mr Wheeler saw a pair of traditional boy’s pyjamas. On the small table next to the other side of the bed Mr Wheeler’s eyes came to rest upon a glass measuring jar between the bedside light and a small bedroom clock. Standing inside the jar was what looked like a thermometer… a long slim clinical thermometer with a bulbous red rubber tip. Mr Wheeler didn’t need to be told this was a boy’s rectal thermometer. He leant forward slightly and squinted enough to read that it was the ‘Junior’ size model. Next to the jar Mr Wheeler saw a small tub of what was undoubtedly lubricating jelly of some sort to be used to ease the passage of the thermometer as it entered Oscar’s bottom.

That thermometer must be the first thing Oscar sees in the morning when he wakes up… and probably the last thing he sees at night, Mr Wheeler thought. A reminder, as if any were needed, of the embarrassment, shame and discomfort he endures when mummy decides to take his temperature. 

Oscar got out his Boy Scout uniform to show it to Mr Wheeler and immediately saw what Mr Wheeler was looking at. Mr Wheeler’s head turned back in Oscar’s direction. Their eyes met for a brief moment before Oscar looked away blushing.

Oscar was so embarrassed about Mr Wheeler seeing his rectal thermometer by his bedside that he was barely able to look at him as he held up his Boy Scout uniform for inspection.

He certainly is a very shy boy, Mr Wheeler thought before he spoke: “Well, it looks as if it’s the same,” he said dubiously as he looked at the uniform Oscar was holding, “I know, why don’t you put your uniform on so that you can show me properly… I’ll help you get changed if you like…”

Oscar didn’t know what to do. He knew that grown-ups had every right to take his clothes off and undress him, just like at the paediatric clinic he attended regularly for check-ups… and after all taking his clothes off was exactly what mummy did at every pyjama-time. Oscar also knew there was nothing wrong about grown-ups seeing him in the nude just like like his PE teacher after every games lesson, or the Scoutmaster at Scout Camps and not forgetting that his parents regularly saw him bare too of course. But even though all of his mum’s friends had also seen Oscar naked at one time or another, it still felt a bit unusual for someone he’d only just met for the first time less than half an hour earlier, for that person to take it for granted Oscar would agree to them helping to take his clothes off.

Nevertheless, unusual or not, when Mr Wheeler reached out and without another word spoken, took hold of and pulled up Oscar’s sleeveless school jersey, Oscar obediently lifted up his arms to let his new neighbour take the jersey off. The woollen pullover, V-necked with Oscar’s school colours woven along the boarders, was stretched inside out over Oscar’s head, ruffling up his hair as it did so. 

Mr Wheeler lifted the jersey up and right off as he pulled it free from Oscar’s arms. He tossed the pullover onto Oscar’s bed and immediately brushed his hands over Oscar’s head to straighten the boy’s hair.

Mummy insisted her son always had a traditional schoolboy haircut at the barber’s and Oscar was sent regularly every two weeks to Mr Fenner’s for a trim whether one was needed or not. Oscar’s short-back-and-sides was something else Mr Wheeler had noticed when they met in the living room. He was pleased to see a boy with such a smart schoolboy haircut.

“There… that’s better,” he turned and sat down on Oscar’s bed. “Now, we had better get these school trousers of yours off next don’t you think?”

Faced with this question, Oscar could do nothing but agree to Mr Wheeler’s proposal Whether it was intended to or not, it certainly made the boy even more embarrassed to be asked to to take part in this way in his own undressing.

Unperturbed by Oscar’s obvious embarrassment, Mr Wheeler kept up a running commentary as he undid the metal clasp at the waist of Oscar’s short grey trousers. He talked to Oscar, asking him questions about school; what were his favourite lessons? He asked Oscar about scouts; what did he enjoy most about scouting? Oscar answered politely as he watched what Mr Wheeler was doing.

The confidant, no-nonsense way in which Mr Wheeler unzipped the fly of Oscar’s short trousers served to reinforce his authority over the boy. Mr Wheeler pulled open the fly to reveal Oscar’s briefs and was pleased to see that Oscar wore traditional white cotton junior schoolboy underpants. They were clearly compliant with the uniform regulations of Oscar’s school. None of this boxer shorts nonsense, Mr Wheeler thought as his hands slipped around and eased the open shorts back over Oscar’s bottom.

“Pull up your shirt, Oscar, so you can see what I’m doing… we don’t want your shirt-tails getting in the way, do we?”

“No, sir,” Oscar replied respectfully as he took hold of the bottom of his short-sleeved grey school short and pulled it up to bare his flat, smooth tummy.

“That’s it, Oscar, right up…”

Oscar was made to pull his shirt all the way to the top of his chest. His school tie dangled down below the now rumpled grey shirt, hanging between his tight, pale pink nipples.

“Good boy, Oscar… we’ll soon have you out of this school uniform at this rate, won’t we?” Mr Wheeler said cheerfully as he gave the brief school shorts a gentle tug, guiding them down Oscar’s smooth legs.

Oscar, as his school regulations prescribed, was wearing long grey soft woollen socks. Woven into the turnover tops were Oscar’s school colours, just like they were in his pullover. Mr Wheeler leant down to lift each of Oscar’s legs in turn in order to remove the the boy’s shorts. He put them to one side on Oscar’s bed next to the pullover.

“Right… what shall we take off next, Oscar?” Mr Wheeler asked, making it sound as if it was Oscar’s idea to be undressed by his new neighbour.

Oscar’s pale pink cheeks grew a little darker as he replied: “Please, sir… my socks, sir?” The rising inflection of his reply made it plain how nervous Oscar was feeling.

“Yes, that’s a good idea, Oscar… We may as well get your school socks off while I’m sitting down before we go any further… Come on, you can help… lift up your leg and put your foot on the edge of your bed… that’s it… good boy, Oscar, you’re being very helpful… but don’t forget to keep your shirt pulled up.”

Mr Wheeler was in no rush and took his time as he ran his hand over the soft woollen school socks. He had been pleased to see that Oscar kept his socks pulled up nice and smart, unlike lots of untidy boys Mr Wheeler could mention. Once more he thought what a well brought up boy Oscar was and Mr Wheeler slipped his fingers inside the top of the sock in front of him. He felt the warm flesh of the boy’s smooth leg as he began to slide the sock down to Oscar’s ankle. He lifted the foot up and rested it on his thigh as he eased the sock back over the heel while Oscar concentrated on keeping himself upright standing on one leg while at the same time using both hands to hold up his shirt. Finally Mr Wheeler pulled the sock all the way off Oscar’s foot, baring the boy’s leg right up to the little white underpants. He kept Oscar standing on one foot as he examined the boy’s foot. It was a tempting sight, but Mr Wheeler suppressed the urge to tickle the boy’s toes. Instead he took hold of the leg and placed Oscar’s foot down on the bedroom floor.

“Next leg, Oscar… and I think we’ll have those underpants of yours off once we’ve finished with your school socks… okay?”

Oscar’s pink cheeks turned a shade darker still as he was forced to cope with the knowledge that his underpants were also going to be taken off. Although Oscar knew very well that he wasn’t allowed to wear underpants with his Boy Scout uniform, he was rather hoping he would be spared the shame of having his underpants removed and being bared completely nude in front of his new neighbour.

Almost whispering he replied: “Yes, sir.”

The quiet, nervous voice of Oscar made Mr Wheeler even more aware of just how shy the boy in front of him was. He pulled down and took off the remaining sock from Oscar’s other leg. The socks were added to the growing pile of Oscar’s schoolboy clothes.

Mr Wheeler stretched out an arm. He took hold of Oscar’s left leg and pulled him a little closer, ready to deal with the underpants. With both hands he took hold of Oscar by the waist and had just pushed his fingers into the waistband of the underpants when Oscar’s mother appeared as she walked through the doorway into her son’s bedroom.

Mr Wheeler looked up and spoke to Mrs Pipe: “Oscar is going to put on his Boy Scout uniform so that he can show it to me properly,” he said and began to ease the crisp white underpants back down over Oscar’s bottom, in the process baring it completely. The underpants were tugged down at the front sufficiently for Mr Wheeler to see there was a complete absence of pubic hair at the base of Oscar’s penis… although Oscar’s boyhood for the moment remained covered by the underpants.

“Well I’m not sure there’ll be any time for that this evening,” mum said, clearly not at all bothered that Mr Wheeler was in the middle of undressing her son - far from it, it seemed. After all it was only to be expected that if Oscar wanted to show off his Boy Scout uniform to Mr Wheeler his school uniform would have to come off first.

Unperturbed Mrs Pipe came into the room to turn back the candlewick bedspread in readiness for Oscar’s bedtime. She uncovered the pillow, picked it up, fluffed it up and put it back before taking Oscar’s pyjamas, which had been lying on top of the bedspread, and placing them neatly next to the pillow. She turned to look at Mr Wheeler, who had by that time moved his fingers round to the front of Oscar’s underpants prior to lowering them.

Mrs Pipe spoke: “When you’ve finished undressing Oscar would you bring him downstairs to the living room… it’s very nearly his pyjama-time.”

Oscar glanced wide-eyed at his mother. He looked worried and if he’d had a hand free Oscar would have been sorely tempted to bite a finger-nail or two, something he hadn’t done for ages, as it dawned on him that he was to be expected to go downstairs completely bare naked. He was thirteen for heaven’s sake, but clearly it was to be pyjama-time as usual!

Mr Wheeler noticed the worried expression on Oscar’s face. He also noticed that Mrs Pipe made no attempt to pick up and take Oscar’s pyjamas with her, so obeying her bidding Mr Wheeler carried on getting her son undressed.

Although Oscar’s pyjama-time had become increasingly embarrassing for him, he was in a sense fortunate that at least he wasn’t to be put into a shortie pyjama-top. He should have known there is always a boy worse off than he was, indeed a boy of fifteen who lived near Oscar was regularly put into a shortie pyjama-top during the summer months at his pyjama-time. No matter how much this boy pleaded with his mother that he was too old, that he was fifteen and that boys his age should have pyjama-bottoms as well as pyjama-tops, she would tell him that once she’d finished undressing him in the family room, he was to fetch one of his shortie pyjama-tops. Mr Wheeler wasn’t to know it yet but, like Oscar, this boy’s pyjama-time ritual required him, after he’d been undressed, to go and fetch his pyjamas from his bedroom and bring them back downstairs. Just like Oscar, he would be told to put his pyjamas on a low side table, so that when mummy was quite ready to get him dressed, his pyjamas would be close by.

Oscar couldn’t help but look down and watch his school uniform underpants being pulled slowly down by his new neighbour. With Oscar’s underpants still only halfway down Oscar’s smooth thighs, Mr Wheeler paused to look at the boy’s penis, now fully exposed. It was clear to see that Oscar’s slim penis had already begun to develop as his puberty progressed.

Mr Wheeler smiled and looked up at Oscar: “No hairs yet, then?”

Oscar’s cheeks darkened a little more as he shook his head a little from side to side and mumbled, “No, sir… not yet.”

“Not to worry… some boys don’t get their hairs for ages… you’ll have to be patient.”

This didn’t seem to cheer Oscar up one bit as he watched and lifted each leg in turn so that Mr Wheeler could take off his underpants. Oscar was still holding his grey school shirt up and was now bare from his chest right the way down to his feet. Mr Wheeler stood up, suddenly towering over the boy.

“Right, let’s get the rest of your school uniform off. You heard your mother, it’s nearly your pyjama-time… better not keep her waiting, eh?”

Once more Oscar was forced to respond and agreed to Mr Wheeler carrying on getting him undressed.

“No, sir…”

Next it was Oscar’s school tie that has been dangling down on his bare midriff. Mr Wheeler made a great fuss about pulling up Oscar’s shirt collar and loosening the tie before undoing the knot so that he could take it off to add to the pile of Oscar’s clothes at the foot of his bed.

The thought of how these clothes would have to be folded properly, passed through Mr Wheeler’s mind. Once I’ve got Oscar completely undressed I’ll give him a lesson on how to look after his school uniform, he thought.

Mr Wheeler spoke: “You can let go of your shirt now, Oscar.”

Oscar did as he was told. The shirt flopped down, but the tails, such as they were, didn’t quite reach the boy’s pubis, leaving him bare from there downwards. Mr Wheeler started to unbutton Oscar’s shirt from the top. The buttons were a bit fiddly to undo and it was a few minutes before his fingers reached the bottom button of Oscar’s grey, short-sleeved school shirt. He undid this last button and pulled the shirt open to reveal Oscar’s pale bare chest and small, pale-pink nipples. As he opened the shirt Mr Wheeler’s thumbs brushed across the little nubbins. Oscar shivered as his nipples were touched and his face grew redder still as in his embarrassment he drew attention to its cause.

Mr Wheeler smiled indulgently, “You’re a sensitive one and no mistake… not to worry, Oscar, boys’ nipples can be very sensitive at this stage of… of growing up I mean,” he added when he saw a puzzled look flicker across Oscar’s face.

This of course made Oscar even more embarrassed than ever. Then he got the shock of his young life when his neighbour playfully tweaked his left nipple. It was all over in a second but it made Oscar gasp and squirm when he felt Mr Wheeler’s fingers pinch and twist the tight nubbin. It was the sort of trick Oscar’s PE teacher would play on unsuspecting boys in the school changing-room after gym. The teacher would sneak up behind a boy, reach round and with unerring accuracy pinch the boy’s nipple, giving it a playful tug. 

Mr Wheeler laughed good-naturedly as he let go of Oscar’s nipple. It was, he noted, now a stiff little nubbin though it was undoubtedly a bit sore after being tweaked.

Not giving Oscar a chance to rub his sore nipple, Mr Wheeler pushed the open shirt back over Oscar’s shoulders, baring them in the process. He then leant over and pushed the grey school shirt down Oscar’s arms.

“Turn around for me Oscar so I can take off your shirt.”

Oscar dutifully turned so that his back was now facing Mr Wheeler who then took hold of one of the boy’s arms and pulled it out of the sleeve. Immediately Oscar used his free hand to soothe his nipple. Mr Wheeler smiled as he freed Oscar’s other arm and put the crumpled shirt on the the bed with the rest of Oscar’s school uniform. 

Oscar was now completely bare of course and Mr Wheeler decided that he better give Oscar that lesson on how to fold his clothes properly. Oscar still had his back to Mr Wheeler who leant over the boy’s shoulder making Oscar twist his head and look up to his neighbour.

“Pick up your school shirt, Oscar and show me how you can fold it properly… I’m sure mummy doesn’t want you leaving your clothes in a heap like that.”

Oscar lifted the shirt up and held it in front of Mr Wheeler, clearly unsure what he should do next.

“Come on, Oscar, you must know how to fold your shirt by now… here, let me show you.” And with these words Mr Wheeler set about demonstrating the best way to fold a boy’s school shirt.

He then unfolded it again: “Here you are, Oscar… you try it.”

Oscar’s attempt at shirt folding was not a success and Mr Wheeler was forced to lean over him and take hold of Oscar’s wrists as he patiently guided the boy through the manoeuvers necessary to achieve the perfectly folded boy’s short-sleeved shirt.

“There we are, Oscar and I expect that soon you to be able to show me how well you can fold your shirts,” Mr Wheeler said and thereby implying in future he would be helping Oscar to get ready for his pyjama-time again. “Now, we’d better get a move on… mummy will be wondering what’s taking us so long to get you undressed.”

It was kind of Mr Wheeler to help Oscar fold the rest of his clothes. Socks, short grey school trousers, pullover, shirt, school tie and junior schoolboy underpants all neatly folded and laid out on top of the candlewick bedspread.

“There we are… nice and tidy. That’s much better isn’t it Oscar? Now let’s get you downstairs.”

Mr Wheeler saw Oscar glance in the direction of his pyjamas. He sensed Oscar wanted to say something but was too shy to do so. He probably wants to tell me not to forget his pyjamas, Mr Wheeler thought and smiled to himself, but Mrs Pipe didn’t pick up Oscar’s pyjamas when she came to turn back his bedspread, so I’d better leave them where they are. I’m not familiar with Oscar’s pyjama-time routine so it would be presumptuous of me to do otherwise. Yes, best leave Oscar’s pyjamas where they are, he concluded.

“Get a move on, Oscar, we haven’t got all night,” Mr Wheeler urged the boy when he saw Oscar hesitate slightly before leaving his bedroom. Oscar padded barefoot… and bare everything, along the landing before turning towards the stairs and descending them down into the hall.

Mr Wheeler followed Oscar closely as he climbed down the stairs in front of him. He was right behind Oscar as the boy approached the front-room. Mr Wheeler placed his hands on each of Oscar’s shoulders from behind and they both stood in the doorway.

Mr Wheeler spoke: “Oscar’s ready for his pyjama-time… aren’t you, Oscar?”

He held Oscar’s shoulders firmly, keeping the boy stood in position with his hands at his sides facing his mother. Mrs Pipe waited and looked at her son expectantly. Oscar realised he’d have to say something and thereby acknowledge that he was standing naked in the doorway of the front-room. It took a few seconds before Oscar answered.

“... er, I’m ready for my pyjama-time…” he said blushing more profusely than ever. 

“Well, I am pleased,” Mrs Pipe said, before adding, “Sometimes you make such a fuss when I get you ready for your pyjama-time… and now here you are standing there all undressed and ready to be put into your pyjamas without any fuss at all. I wonder if I shouldn’t ask Mr Wheeler to come and help me get you ready more often…” Mrs Pipe suddenly stopped and looked up at Mr Wheeler in the doorway. “Oh, I am sorry, that was very discourteous of me… I expect you’ve got better things to do than to get Oscar undressed and ready for his pyjama-time.”

Mr Wheeler was honoured to be asked: “Why, I’d be delighted to help you with Oscar whenever you need an extra pair of hands… I’m only next door, so just let me know.”

It has to be said that the look on Oscar’s face was not one of unalloyed joy. Had he but known that his expression only served to confirm his mother’s view that an extra pair of hands would indeed be very useful, Oscar might have attempted to keep a straight face instead instead of the anxious frown he was wearing.

“Thank you, I most certainly will,” Mrs Pipe said in reply.

Mr Wheeler stood behind her naked son. What he did not expect was Mrs Pipe’s seemingly utter lack of concern, almost bordering on contempt, for Oscar’s obvious discomfort, not to say embarrassment, as he stood totally bare in the doorway. Once more Mr Wheeler marvelled at the casual indifference shown by mothers towards their son’s nudity, a subject of which he’d had some personal experience in his own teen years.

Mrs Pipe addressed her son: “Where are your pyjamas, Oscar?” she asked.

“I’m afraid they’ve been left upstairs,” Mr Wheeler apologised on Oscar’s behalf, “Oscar didn’t say anything and I assumed…”

“It’s not your fault… Oscar should have told you. Never mind,” she said waving a hand dismissively, palm facing outwards, above her head, “Oscar can go and fetch his pyjamas in a minute.” She turned and told Oscar to go and get the footstool so that he could have somewhere to sit while he waited.

The ‘minute’ turned out to be somewhat longer than sixty seconds and inevitably Oscar began to fidget. After the second time of being ticked off, Oscar was ordered to sit on his hands in an attempt to stop him fidgeting.

Five minutes later Oscar was again admonished for fidgeting. This time he was told to put his hands on his head as he sat on the footstool. After sitting naked on the footstool in the middle of the front-room with his hands on his head for a further ten minutes, Oscar was finally told by his mother to go and fetch his pyjamas from his bedroom.

Relieved to leave the room and to be out of sight of his mother and Mr Wheeler, Oscar went back upstairs to his bedroom. He picked up his boy’s pyjamas, but knew better than to put them on and somewhat slowly returned to the front room where Mr Wheeler and his mother were still chatting away, seemingly unconcerned by the naked boy bringing his pyjamas.

“Put your pyjamas down there,” his mother said pointing to the small table by her chair, “We’ll get you ready for bedtime in a moment.” She turned back to continue her conversation with Mr Wheeler. Oscar stood and waited. He hadn’t been told to sit down again and was obedient enough not to do so unless he was given permission. This of course made him feel more exposed than ever and there was a real concern that at any moment someone would call round to visit his mother. Like any boy left naked waiting to be put into his pyjamas, he just wished mummy would get on with it so he didn’t feel so nervous and vulnerable. 

Oscar couldn’t help himself and it wasn’t more than a minute later that he was told off for fidgeting again.

“For heaven’s sake sit down, Oscar,” Mrs Pipe snapped, “and you can put your hands back on your head.” She turned to her neighbour: “Honestly, Oscar can’t keep still for more than two minutes.”

Mr Wheeler smiled: “I’m afraid thirteen year old boys are not renowned for their patience.”

Mrs Pipe sighed: “How true…”

Oscar did as he was told and looked almost relieved to be sat down rather than standing, perhaps feeling a little less as if he was on display.

When mummy did eventually pick up Oscar’s pyjamas it was only to show them to Mr Wheeler. She passed him Oscar’s pyjama bottoms and Mr Wheeler examined them thoroughly. He looked up at Oscar who blushed when he saw his neighbour deliberately checking the front of the pyjama bottoms for any signs of naughty nighttime behaviour… at least that’s what Oscar guiltily thought Mr Wheeler was doing and he blushed a deeper red accordingly.

Mrs Pipe noticed what her neighbour was doing: “Yes, I’m afraid Oscar has reached that age,” she observed.

“You mean Oscar has started to play with himself… masturbate, I mean?”

This was a bombshell and no mistake for Oscar. He thought he’d been so careful and that his secret was safe. Mummy hadn’t said anything and like all boys he thought she would never suspect that he played with himself. Now for some reason she felt able to talk openly to their new neighbour no matter how shameful it was for Oscar to be exposed as a boy masturbator in front of them as if it was no big deal.

But it was. A very big deal and Mrs Pipe was relieved to be able to talk to her new neighbour about what she called Oscar’s ‘boy problem’. She had known for some time that her son masturbated, but didn’t know what to do. She had talked privately to Oscar’s paediatrician who had simply told her that it was a phase lots of boys go through and not to worry, Oscar would soon grow out of it.

From the tone of her voice Mr Wheeler could tell the sort of advice Mrs Pipe wanted to hear: “Would you like me to have a little talk with Oscar?” he suggested, “I mean, I know that we’ve only just met, but if it would help…” he paused for a brief second before sympathetically adding, “This can be a difficult time for boys of Oscar’s age when they begin to grow up and see their bodies developing… the onset of puberty can be very confusing for them.” 

There was an unmistakable look of relief on Mrs Pipe’s face as she replied: “Would you? Could you? It would certainly put my mind at rest about it… you know I spoke to Oscar’s paediatrician about him masturbating and…”

Her words were cut short by a shocked response from Oscar, sat naked in the middle of the room on a footstool with his hands pressed firmly on his head. This was too much: “Oh MUM… You didn’t… mum… please…”

It was clear that Oscar was very upset to learn that his mother had talked to his paediatrician, but when he saw the look in her eyes he knew that he better not say any more. It wasn’t fair. Mums didn’t realise just how embarrassing it was for them to be talking about what their sons got up to, especially when the boy is convinced he’s been so careful that he thinks his mum would never guess.

Mrs Pipe continued: “... and, well, let’s just say that they weren’t very helpful.”

Mr Wheeler was sympathetic: “That’s a shame. I would have thought they’d have been a lot more supportive.”

“Yes, I agree, but that’s why I’d be so grateful if you would have a little talk with Oscar about it… about masturbation I mean.”

Although he realised how embarrassing it must have been for Oscar to be sitting naked in front of them as they discussed his masturbation ‘problem’ as if he wasn’t in the room, Mr Wheeler wasn’t about to let that bother him. “Maybe later… when you’ve put him to bed.”

Mrs Pipe thought this a splendid idea and picked up Oscar’s pyjama-top.

“It’s about time we got you into your pyjamas, Oscar,” she said, in a tone that made it sound as if it was Oscar who was responsible for the delay in getting him dressed for bedtime. This came as a relief to Oscar who instantly stood up and went to stand in front of his mother, eager to be put into his pyjamas at last. He had been naked for almost an hour since their new neighbour, Mr Wheeler had undressed him in his bedroom. Oscar didn’t fancy the idea of the ‘talk’, but it couldn’t be as bad as spending half the evening in the nude… could it?

As it turned out the talk wasn’t as bad as Oscar had feared. Nonetheless it was still a nerve-racking experience for the thirteen year old. Oscar had only ever talked to his close friends about wanking and certainly the subject of masturbation had never been broached in the presence of a grown-up before, least of all his mother. As boys of Oscar’s age always do he was sure his mother would never find out or even suspect that he masturbated. In fact Oscar and his friends were pretty certain that mums didn’t even know what wanking was. So lying tucked up in bed and having to talk about masturbation with Mr Wheeler was a new and anxiety inducing experience to say the least.

“You know lots of boys think their mums don’t know what they get up to, Oscar, but you’d be surprised… you’re just lucky you haven’t been caught,” Mr Wheeler told him.

“I think you know it is naughty to play with your penis, don’t you, Oscar? But I know that’s not going to stop you. I wouldn’t be at all surprised if you told me you masturbated with your friends.” The look on Oscar’s face confirmed Mr Wheeler’s suspicion. “Yes, I thought so. I bet there’s a lot of rivalry among you and your mates… encouraging each other, daring and egging each other on as you masturbate in front of each other. Isn’t that what you do, Oscar?”

Oscar couldn’t bring himself to admit to Mr Wheeler that he did indeed masturbate with his friends. Blushing he simply nodded.

“Yes, I thought as much. But you must realise, Oscar, that masturbating whether it’s with your mates, your best buddy, or on your own, you have to learn to control yourself… do you understand?”

Oscar again nodded shyly.

“So what I want you to think about, Oscar, is whether you are going to be a good boy and be open with me and tell me what you get up to so we can talk about it, or whether you are going to be secretive and try to hide what you’ve been doing. It’s no use thinking that your mum won’t find out what you’ve been up to, because she will…” Oscar looked alarmed, but Mr Wheeler assured him, “Don’t worry I won’t tell her because I won’t need to… mums are like that, they find out things, that’s what they do. So it’s all about controlling yourself, Oscar and that’s where I want to help. I want you to learn to masturbate responsibly… will you do that for me?”

Again Oscar nodded even though he was unsure what masturbating responsibly meant. He simply wanted the talk to finish so that he could have a good wank before he went to sleep. All this talk about masturbation had naturally resulted in an erection which Oscar prayed Mr Wheeler hadn’t noticed. Oscar shifted about in bed as he tried to make less obvious what was happening underneath the blankets.

“That’s good, Oscar… now, so that I can help you do that, I need you to keep a record of when you masturbate… a masturbation diary. Can you do that?”

Oscar was horrified and the expression on his face reflected how he felt.

Mr Wheeler smiled indulgently: “Oscar, I know how often boys your age masturbate.” He looked down at the bump about halfway down the bed that Oscar hadn’t managed to completely disguise. “And I can see that’s what you can’t wait to do the minute I go… well, be careful when you do, Oscar and try not to make a mess… you’re spunking up now, aren’t you?”

Oscar visibly squirmed. Of course he was spunking up! He was thirteen! Shyly, he nodded.

“Yes, I thought so… now in future every week you and I will sit down and you will show me your diary… your masturbation diary and we’ll talk about what you’ve been up to… agreed?”

Oscar had little choice but to agree.

Mrs Pipe was thrilled when back downstairs in the living room Mr Wheeler told her how Oscar had agreed to meet him each week to have a chat about what he called ‘boy stuff’. Mrs Pipe suggested the meetings take place at Mr Wheeler’s house. She explained: “Oscar is more likely to talk to you at your house than he would do at home.”