Saturday, 31 October 2015

A Trip to the Doctor’s for Oliver

The following story was written by Tom, a reader of this blog who was inspired to write a sequel to my story 'Stephen's Mum has a Visitor'. He has kindly given his permission for me to post his story, the first one he has written.

A reminder that Wincy has also written and posted a story on his blog featuring Oliver and Stephen. The links are on the Story Index page which can be accessed from the top right of this page.

A Trip to the Doctor’s for Oliver - by Tom   

Mrs Evans was apoplectic with Oliver, showing her up in front of Mrs Wilding and young Stephen like that with his erect seeping winky, something would have to be done; there must be a reason why Oliver keeps touching his winky, was it just a wilful boy nastily obsessed and wilfully disobedient or was there possibly a medical reason for Oliver's behaviour?

Thankfully Mrs Wilding seemed to understand: “Oliver can't go home in those stained rompers, I wonder if a spare pair of Stephen's school shorts would fit Oliver, they do have a stretchy half elastic waistband and I could lend you a pair of Stephen's white school briefs as well.”

Mrs Evans was most grateful as Mrs Wilding went off to find the necessary items and she watched Oliver standing snivelling in the corner STILL with the offending erection, something would have to be done...

Stephen watched Oliver crying in the corner who cut a pathetic figure, apart from that erection, he thought. How big was it? It must been at least six inches, possibly as much as seven, while he knew that his own stiff winky was four and three quarters at best. Oliver didn't look a big boy normally, although considerably taller than himself, but Stephen couldn't help but admire Oliver’s appendage...

Mrs Wilding returned: “They are probably a bit small but I'm sure they'll get you home okay Vera.”

Vera Evans was most grateful. “Why thank you, I really can't apologise enough for Oliver’s nasty display, Felicity. I'm going to have to have a serious talk with him.”

“Oh don't worry Vera, we can have a chat about this next time we meet. Between ourselves I'm rather worried about Stephen in that regard.”

Vera Evans gave an exasperated and knowing look to her new friend, “Well, I'd better get him dressed...”

Mrs Evans turned to the snivelling Oliver in the corner. Stephen sat silently in the arm chair wide eyed at the afternoon's display.

“Oliver, come here.” Mrs Evans commanded. Oliver, still weeping, shuffled across the room with his erection as hard as ever. “What am I going to do with you? Stand still and don't you DARE move!”

Mrs Evans slapped Oliver's penis several times among much hip movement from Oliver but eventually, as Oliver wailed, his erection subsided.

“Now Oliver you are going to have to wear a pair of Stephen's school shorts and underpants and if I find you have marked these you will be in serious trouble,” Mrs Evans said as she  used a pocket tissue to wipe “winky” clean and dry.

“Step into these first...” Mrs Evans held out a small pair of brilliant white locknit boys Y fronts and Oliver gingerly put each foot into the proffered holes while Mrs Evans yanked them up. They were tight but would do for the trip home.

Mrs Evans then held up the junior boys school shorts with a strong elasticated back. They were a heavy quality item made of wool and polyester with a brilliant white nylon lining. Oliver couldn't believe he would get into them but he wasn't about to argue, he just wanted to get home and away from this cringing embarrassment.

The shorts were pulled up Oliver's long smooth legs and Mrs Wilding pulled the clip together stretching the waistband almost to its maximum. Oliver looked sullen and resigned to his fate as his mother held the waistband at the clip and pulled up the zip with a resounding zuuuup.
The shorts certainly lived up to their name… there was hardly any leg to speak of which barely fitted Oliver's athletic thighs. The school shorts were also quite tight around his rather full bottom. They were Stephen's school shorts from last year, with a mere one inch inside leg as recommended by the outfitters. Short on Stephen, they were incredibly short on poor Oliver. Stephen, looking on, couldn't help but notice the still clear outline of Oliver's winky straining at the front of his shorts in much the same way Oliver was aware was the case with his “naughty shorts”.

As soon as Mrs Evans got Oliver home by bus, much to the amusement of several schoolgirls she phoned the Doctor's to make an appointment for Oliver.

“Doctor Willis will see you now,” the receptionist called to Mrs Evans, as Oliver sat in the waiting room dressed in his full school uniform of brilliant white shirt, green and gold striped school tie, green v-neck school jumper complete with his junior elasticated waist school shorts with only a one inch inside leg. His ensemble was topped off by his navy-blue school blazer with school crest, matching school cap, long grey knee length socks with two green bands at the turn over and his best polished brown school sandals. He was the very picture of a perfect prep school boy, thought the receptionist as Oliver passed by. Was he a very tall 12 year old or could he possibly be older? Still, he looked VERY smart indeed she thought, much better dressed and consequently behaved than many young boys she had seen.

He must be at prep school the receptionist thought, after all he was in the uniform of a junior boy. But then again it was the school holidays. She was puzzled. I know, she thought, I'll just have a quick look at his file for his date of birth, that will solve the conundrum!

SEVENTEEN! Good grief she though, and only 3 months off being eighteen and still accompanied by his mother! And still in short trousers!!

Oliver entered the doctor's room still not knowing why on earth he was there. He had naively assumed that his mother needed to see the doctor but surely she would have left him in reception, he thought?

“Good morning Dr Willis,” Mrs Evans said.

“Good morning Mrs Evans, what can I do for you?” the doctor responded looking first at Mrs Evans but then lingering on the unusual sight of a very tall prep school boy present before her. Oliver immediately noticed how very attractive the doctor was. She must be in her mid-thirties at most, Oliver thought, with long black hair she was the spitting image of…

But Oliver’s revere was cut short when mum explained the reason for their visit.

“Well Doctor Willis, it's really a problem that Oliver here is having... and I'm not sure if its a medical problem or Oliver is just being naughty.”

Oliver blushed profusely and looked extremely nervously at his mother. He was beginning to understand why mum had brought him to see Doctor Willis.

“Why don't you sit down and tell me all about it” said Dr Willis.

Mrs Evan sat down. Oliver was left standing.

Mrs Evans started with an “ahem” but proceeded to relay the events that had occurred on their recent trip to see Stephen and his mother. The troubling erections and Oliver’s constant need to fidget with his winky. No detail of the event was missed and Oliver was bright red and staring at his brown sandals. He was already embarrassed to be standing in the doctor’s office dressed in full school uniform, but this was nothing to what he was now hearing.

Doctor Willis listened intently, occasionally looking at Oliver with some concern and then back at his mother who mirrored the concern in her face as she continued: “You have no idea how embarrassed I was in front of Mrs Wilding, seeing Oliver standing there with a full erection. No matter how much I punish him he seems to wilfully disobey me. I wondered if it may be a medical problem and… you see I don’t want to punish him too much if it isn’t really his fault.”

“I see Mrs Evans,” Doctor Willis said sympathetically, “I can well understand why you brought Oliver to see me and asked for me specifically. As you know I do have a speciality in this area. Let me say straight away that boys of Oliver's age should be able to control themselves… their, ahem winkies... so let's do some basic checks first.”

Oliver was made to stand in front of Doctor Willis as she looked him up and down. Oliver was then told to take off his blazer and jumper and basic checks on pulse and blood pressure were taken.

Oliver was made to face Doctor Willis and he couldn't help but notice that she had rather a large chest under her fairly low cut dress. When Oliver looked down he could see the doctor’s cleavage in full relief. Then he gulped and felt beads of sweat prickle his forehead. Oh no! he thought, winky is getting stiff again! NOT NOW PLEASE!

As Oliver stood before Doctor Willis, his groin only inches away from Doctor Willis's face and with his shorts tightening clearly in front of her, Oliver began to feel tears of frustration welling up. He desperately wanted to adjust winky, but he knew he dare not.

“OLIVER! What is the meaning of this…?” Mrs Evans said and pointed at the large bulge that had appeared in the front of Oliver’s short trousers, “... right in front of the doctor! Have you no shame?!” Mrs Evans said and landed a sharp volley of stinging slaps on Oliver's bare thighs. Oliver burst into tears, blurted out his apologies and begged forgiveness.

“It’s alright, Mrs Evans, I’ll deal with this,” Doctor Willis said as she ignored Oliver’s pleading, “Oliver's pulse is a little high at the moment but that's understandable, however I think we should take a look at the problem area now...”

With those words and as he saw the doctor’s hands come closer to his school shorts, Oliver pulled away but another resounding slap on this upper thigh stopped him in his tracks. Doctor Willis pulled him to her side as Mrs Evans said sharply: “Hands on head, Oliver.”

Doctor Willis carefully unzipped Oliver's shorts and with the experienced hands of a mother only too used to this sort of thing, undid the two clips at the waistband. Oliver's shorts were eased past his burgeoning erection and slipped over his bottom and slid down his thighs with clear expertise of a woman who had done this sort of thing countless times.

Oliver's tight white schoolboys Y-fonts stared back at Doctor Willis, tented and strained, with a clear damp patch forming.

“I think we’d better have these down too, Oliver...” Doctor Willis said as she pushed her fingers into the waistband of Oliver’s junior schoolboy's underpants and eased them down. She leant forward slightly and noted the label stitched into the waistband at the back of the junior underpants  ‘Ladybird, Age 14-16 yrs’. As the doctor pulled the underpants past Oliver's winky his erection sprung out and hit her on the nose.

Mrs Evans was horrified: “Oliver! How DARE you…” As Mrs Evans began to scold her son, Doctor Willis recoiled from the appendage wiggling before her. She noticed clear pre-cum beginning to dribble from the tip of the penis.

“Not to worry Mrs Evans, leave this to me,” Doctor Willis said with a stern, matter of fact voice. She turned to Oliver: “Now let's have a look at you...”

With tears streaming down his face Oliver had no choice but to comply.

“Mrs Evans, first observations are that Oliver does not seem to have any pubic hair at all. I would have expected Oliver to have produced some hair by now... in fact most boys his age have a full growth of pubic hair.”

“Doctor, Oliver has had so few hairs down there… around his winky... but they were so few, light and straggly, that I thought it best to remove them… they were so untidy. In fact he didn't have any hairs at all around his winky until last year isn't that right Oliver?” Mrs Evans said through pursed lips.

Poor Oliver had no option but to reply: “Yes, yes… that's right, I got my first one two weeks after my 16th birthday,” Oliver snivelled.

“I see,” Doctor Willis said, “I think we had better “measure you up” Oliver. With that Dr Willis produced a ruler and placed it at the base of Oliver's penis and took careful note.

“Are you fully erect now Oliver?” She asked.

“Umm…” Oliver snivelled, “I… I think so Miss...”

“Well, Oliver is certainly more than okay for his age as far as penile length is concerned, Mrs Evans,” the doctor announced, “Five to six inches is quite normal for a boy his age, but Oliver here… his penis is very nearly seven inches in length... that's quite impressive.”

Gathering a tape measure from her desk drawer the doctor proceeded to wrap the tape around Oliver's erection, “Nearly 2.7 inches, that's certainly healthy... perhaps a little too healthy!”

“I'm going to check your foreskin now, Oliver” Doctor Willis said as she got up close again, giving Oliver a clear view down the top of her dress to her heaving cleavage. Oliver couldn't control himself at the sight before him and winky twitched upwards seemingly with a mind of its own. Oliver had butterflies in his lower abdomen and his upper legs felt weak, he'd never had a feeling nor a sight to see like this before.

Dr Willis took Oliver's erection lightly in her warm hand and started to slowly ease back the foreskin. Oliver, overcome as he was, sobbed out loud. Mrs Evans was heartily sick of the show that her son was making of the simple medical examination and her patience was beginning to wear thin.

As his foreskin was slowly retracted by the doctor, Oliver realised he couldn't help himself. His tummy was full of butterflies. His legs turned to jelly and his hips involuntarily thrust back and forward in tune with his sobs. A few seconds later and Oliver shot a huge volume of semen straight at the doctor's face and before she or Mrs Evans could react two more jets caught the doctor's cleavage and upper dress.

“OLIVER! You disgusting… perverted…” Mrs Evans was almost speechless with anger at Oliver for losing his self-control, but she managed to calm down enough to offer her apologies to Doctor Willis, “I'm so sorry doctor... I don't know what to say...”

Doctor Willis was stunned at Oliver’s behaviour, “Well, I haven't had that happen before in surgery,” she said through pursed lips and gave Oliver a stern look. A string of semen hung from the tip of Oliver’s penis and swayed as he was admonished by the doctor.

Oliver snivelled and sobbed and could only stare at his brown school sandals, framed as the sight was by the offending erection of his winky, still twitching at full extent as he sobbed.

Doctor Willis turned to Mrs Evans: “I'll have to go and clean up, fortunately I do have some clean clothes, will you excuse me for a moment?”

Mrs Evans snapped out of her disbelief: “Of course doctor. I'll deal with Oliver if you don't mind, I think he has quite a lot to apologise for,” and then looking very sternly at Oliver, added “Don't you!” with a measure of menacing force.

Mrs Evans reached for her handbag and shuffling through it, soon found the short discipline strap. It was really kind she thought of Mrs Wilding to lend her a spare one the other day, wondering as she did, where she could get such an effective implement for Oliver. After all, his eighteenth birthday was coming up, what a lovely present it would make, I must ask where Mrs Wilding got them from, she thought.

The doctor left the room and Mrs Evans stared at Oliver for a few seconds.

Holding the strap, Mrs Evans said in a low menacing voice: “Here… Now!”

Oliver, still snivelling, shuffled hesitantly across the room, his stiff winky still dribbling and swaying from side to side.

“Mummy, I'm very sorry, I didn't mean to...”

“You know what I want to hear, Oliver,” Mrs Evans whispered through pursed lips.

“Mummy… I'm… I'm very sorry... I really am. I’m so sorry that winky got stiff again, but...”

“Indeed it did Oliver, but that's not all winky did is it?” Mrs Evans continued.

“I'm very sorry, mummy... I don't know what winky did, honestly mummy…  Winky felt all… all… funny. I couldn't stop winky… honestly mummy. I didn’t want winky to...”

“What else do you have to say, Oliver... and be quick about it!”

Oliver snivelled again, and finally got the required words out, as Mrs Evans lightly tapped the strap in her palm.

“I'm very sorry mummy... I've been a very naughty boy again because I lost control of winky... and… and I'm very sorry about the white stuff that winky squirted at Doctor Willis…” Oliver took a deep breath and added, “I've been a very naughty boy, mummy and I... I… deserve to be properly punished.”

“I should think so too... and what will you be saying to Doctor Willis when she returns?”

“Please, mummy…”

“Come on, Oliver… What will you say to Doctor Willis?”

Oliver took another deep breath and told mummy what he’d say: “I'm very sorry Doctor Willis that I lost control of winky and that I let winky squirt white stuff on you...” Oliver said, but realising more was required, he continued, “... and I've asked mummy to punish me most severely for my misdemeanours…”

“That's better Oliver, now get over my lap NOW! It's time for you to atone for your wrongdoings.”

Mrs Evans lifted her skirt up her thighs, she had no intention of getting her clothes ruined by Oliver's sticky mess. After a series resounding slaps to Oliver's bare legs, which caused a little on the spot dancing, Mrs Evans took Oliver's arm and guided the boy straight over her knee, being careful to make sure Oliver's still engorged winky was placed between her thighs and wedged stiffly against the underside of her left leg.

Oliver was sobbing as he felt winky pressed up against his mother's silk stocking and the light rubbing was causing poor winky to twitch again, he just couldn't help it and knew that his punishment would be the greater for winky's continued disobedience.

Mrs Evans, lips pursed, set about Oliver's bare bottom and thighs with the short leather two tailed strap. Short as it was, it was nevertheless a fearsome instrument; stiff as poor winky and over a quarter of an inch thick. Once again she thought how kind it was of Mrs Wilding to let her borrow her spare discipline strap.

Wailing howls were interspersed by regular thwacks as Mrs Evans set about the punishment, with Oliver's right arm twisted and pressed up against  his back to ensure he maintained his position. After only ten meaty thwacks, Oliver was crying like a baby when Doctor Willis re-entered the room.

“Ah doctor, I'll pause and have a break in Oliver's punishment for now as I know time is pressing” Mrs Evans said, as Oliver sobbed over her lap.

“Get up Oliver, NOW!” Mrs Evans instructed in a stern voice and Oliver scrambled in an undignified fumble to get off his mother's lap.

“Stand here next to me facing Doctor Willis. I want to hear what you have to say by way of apology for disgracing yourself.”

Oliver stood up straight to the left of Mrs Evans with winky still erect and pointing towards Doctor Willis. Oliver moved his hands to try to shield poor winky but the instruction to put his hands on his head from mummy, put paid to any thoughts of modesty or self-preservation he might have had.

“Let's hear it then Oliver,” Doctor Willis said.

“I'm… I'm… very sorry… very sorry indeed, Dr Willis… I’m sorry that I let... my… let winky get all stiff and I’m sorry if I upset you when winky squirted all that white stuff at you...”

Doctor Willis looked at Oliver, who was staring at the floor after his apology. She looked up from his brown school sandals to the seven inch twitching appendage that Oliver couldn't control and saw that it was still dribbling occasional stringy droplets that dangled towards the floor.

“AND Oliver?” Mrs Evans prompted.

Oliver bit his lower lip and continued, “...and mummy will punish me most severely when she gets me home and I will thank mummy most sincerely afterwards for helping me with my punishment”

“That's better Oliver, you know this is FAR from over but Doctor Willis has a job to do now so we must let her get on with it without further mishap, and if there is a mishap, you know what will happen to you don't you?”

Oliver sobbed and nodded his bowed head.

Doctor Willis, taking no chances this time, pulled Oliver towards her by the hand, and positioned herself out of the firing line as it were, at Oliver's side. “Now Oliver, lets complete that inspection shall we?”

The doctor, with one hand grasped around Oliver's waist took winky, as it continued to twitch between her thumb and forefinger and gently eased back the foreskin which had slipped forwards, to reveal the glans again. Oliver started to cry and once more tears streamed down his flushed cheeks.

“Does that hurt at all Oliver?” Doctor Willis asked.

“Err... not really Dr Willis,” Oliver sobbed, “but it makes me feel very funny, I think winky might be about to do something naughty again...”

Mrs Evans looked at Oliver with her most stern, no-nonsense face and Oliver realised he'd better get winky under control, or goodness knows what mummy or Doctor Willis might do.

During an extensive inspection of the glans and meatus of Oliver’s penis, which seemed to take an absolute age, Oliver thought of the strap mummy was still brandishing in her hand and by this means he managed to avoid a further embarrassment.

Doctor Willis examined Oliver's extensive shaft, slowly moving her inspection to the base of the penis in a thoroughly professional manner She had to hold it quite firmly as it kept twitching occasionally. Reaching the base, Doctor Willis ran her hand over his pubis and was amazed to find it even smoother than it looked.

“Well, that's unusual on a seventeen year old boy... absolutely no hairs starting at all... completely smooth...” Doctor Willis said as she ran her fingertips all around the base of Oliver’s penis.

Oliver blushed a shade of crimson that his mother hadn't seen before, not even on his bottom after a good smacking.

“Oh there has been the occasional one Doctor Willis,” Mrs Evans informed the doctor, “but they were so thin and wispy there was no point in leaving them... they looked so untidy so I simply pulled them out with my tweezers. They come out very easily don't they, Oliver?”

Oliver knew better than not to reply, “Um, yes mummy, there has only been a few...”

“Now Oliver, I'm going to check your testicles,” Doctor Willis added, being careful to remain out of winky's firing line.

Oliver was terrified. He had barely survived the prolonged inspection of winky. Doctor Willis took hold of the root of Oliver's seven inch throbbing appendage with one hand and lifted it slightly from the horizontal. Then she gently cupped Oliver's testicles in her other hand, rolling them between her fingers. Oliver gasped and immediately started thrusting as a natural reaction but Doctor Willis, quick as a flash, released the testicles and applied a series of resounding slaps to Oliver's thighs which Oliver could do nothing to prevent as his poor winky was still tightly gripped by Doctor Willis.

Mrs Evans jumped from her seat with her strap in hand and quickly applied a few expert blows to Oliver's bottom as he tried to move away, but it was hopeless as Doctor Willis had him firmly held by his penis and five additional stingers met with Oliver's mid thighs.

Finally Doctor Willis announced that she had seen enough and Oliver. Exasperated, poor Mrs Evans said that she had just about as much as she could take of Oliver's antics for one day.

“If you are finished doctor, I'll get Oliver dressed again,” Mrs Evans said.

“Oh yes, you can dress him now. I think I have most of the information I need... an unusual case, but I have seen this sort of thing before,” Doctor Willis said in a matter-of-fact voice whilst eyeing up Oliver who continued to both sob and throb.

“If you like, I can deal with that erection for you... it won't take a second,” Doctor Willis added.

“If you would please doctor... that's most kind of you,” Mrs Evans replied.

Doctor Willis once more took hold of the still heavily engorged penis and, with a series of expert flicks of her finger aimed at the very tip of Oliver's member, swiftly succeeded in getting the erection to subside as Oliver howled, snivelled, and rapidly stamped his school sandals.

Although the penis was still noticeably tumescent, it was at least pliable enough for Mrs Evans to get Oliver's white Ladybird underpants back on properly. She then picked up Oliver's junior boy’s school shorts and opened them out, testing the rear elastic as she did so. She offered them to Oliver: “ Come along...right leg up, good boy, that’s it... now the left leg.”

Mrs Evans dressed Oliver, easing the shorts up his legs and over his thighs, looping the rear of the shorts over his bottom in time honoured fashion. She took hold of the front of the shorts at the waistband she pulled them into place, easing then over Oliver's still swollen winky before fastening the the double clip. Mrs Evans noted they were getting a bit tight for Oliver. He must have grown the last few months, she thought and made a mental note to get him back to the school outfitter's for a new pair.

Mrs Evans pulled up the waist to ensure the shorts were firmly in place before she finally did up Oliver's zip after a slight struggle getting it past the bulge of his boy-bits. Oliver, with his school blazer and cap back on, looked every inch the junior schoolboy, she thought. If the public were going to see his reddened thighs, that's no more than he deserved for his display this morning, she thought!

“I think we need to have a few words in private, Mrs Evans. Perhaps if Oliver went and sat in the waiting room?” Doctor Willis proposed.

Mrs Evans was, as ever, keen to oblige the doctor. She turned to her son: “Oliver, go and sit in the waiting room until I'm finished with Doctor Willis and I don't want ANY trouble do you hear?” she added whilst waving her discipline strap before she replaced it in her handbag.

Oliver was acutely aware that his eyes must look very red from all the crying but that was as nothing to the rosy red glow of his thighs, so he left the doctor's office with real trepidation. As he entered the waiting room his gaze was immediately met by the receptionist, who's eyes widened when she saw his reddened thighs. Then Oliver looked around and saw there were eight people all doing the same thing! Everyone was looking at his bare and very red thighs! Oliver didn't know where to look... he felt so ashamed. What made it even worse was the only available seat was next to a young blond girl who already was staring at him wide-eyed and silently giggling with her hand over her mouth.

Oliver could do nothing but proceed, with all eyes on him and sit next to the giggling girl. How much worse can it get? he thought. She looks to be only about fourteen and worse still, he was sure he'd seen her at his school!

The girl watched his every move as Oliver shuffled across the floor. It felt like he'd walked a thousand miles before he sat down, head bowed staring at his T-bar schoolboy's sandals.

Suddenly a hand appeared on his thigh, just below the rucked-up hem of his school shorts, which startled him: “It’s Oliver isn't it?” said the girl, “I'm sure I know you, don't I?”

Oliver's heart went into overdrive.

Part Two can be found here

Monday, 5 October 2015

Scott's Story - Part 8

After being given a strip-wash and put into my new pyjamas by Miss Emily, who had given me Teddy to carry, I confess I was glad to get back up to my bedroom again. Even though it was still quite early nothing suited me more than to be put to bed and left alone. It was horrible knowing that I had been watched by children who had been playing outside the house as I was prepared for bed by Miss Emily in front of the sitting-room window.

Up in my bedroom Miss Emily made sure I knelt down by my bedside to say my prayers which of course had to include thanks and apologies to mum and Emily. Thanks for them taking so much trouble and taking the time to make sure I was better behaved; thanks for my new school uniform and the blisteringly short grey trousers; thanks for my new play-clothes and thanks for the jimmy-jams I was wearing. I included a long list of apologies in the hope that Emily would not find any reason to address my shortcomings and I finished off with a heartfelt plea: “Please help me to be a good boy…”

After prayers Emily held up the bedclothes and I slipped between the sheets. I held tightly onto Teddy as Emily made sure I was tucked in properly. Instinctively I pushed my arms underneath the sheets, but Emily gripped my upper arms and pulled them out again.

“Good boys always sleep with their hands on top of their bedclothes where they can be seen,” she explained as she placed Teddy under one of my arms. “Baby-sitters must always be able to see a boy’s hands…” Emily said just as if she was reciting something she’d been taught. “Promise me you’ll do that…”

“Yes, Miss Emily,” I said and wondered if Emily meant what I thought she meant about the reason for keeping my hands on top of the bedclothes. It made me shiver just to think that Emily might know what boys get up to when left to their own devices… and if she did, what that might mean for me!

“Now straight to sleep, Scottie… and no getting out of bed. Do you understand?”

“Yes, Miss Emily… I promise,” I said and clutched Teddy tightly.

I hope it doesn’t get me into trouble, but after Emily left my bedroom and closed the door behind her, I lay in bed thinking... thinking how much I wanted to play with Willy Winky.

Willy Winky itched to be played with, but with my hands laid obediently on top of the bed-spread I could only lie there frustrated. You’re probably going to ask why I didn’t just push my hands underneath the bedclothes and play with Willy Winky, but to tell the truth I was simply terrified Miss Emily would come back and catch me, so that I just couldn’t run the risk. Besides I was nearly sixteen and I’m sure you realise what happens when a boy of that age plays games with Willy Winky. The last thing I could afford was for Miss Emily to find… well, you know what she would have found! The evidence would have been damning and I couldn’t bear the thought of having Miss Emily, let alone mum because you can be sure she would have been told, telling me off as they examined by pyjamas.

I can’t imagine there could be anything more humiliating for a boy than to be forced to admit that he’s been playing with Willy Winky, especially if he has to admit to doing so in front of mummy or his babysitter. Can you imagine what Miss Emily would have said? It makes me shudder to think. She probably would have pulled me by the ear and taken me to see mummy… and it would only have taken one look at the damp stains on my pyjama bottoms for mummy to know I’d been playing with Willy Winky.

There was another reason why I was afraid to play with Willy Winky which is going to make me sound like a complete dork, but as you more than likely already think I am one already, I may as well tell you. It was Teddy. I simply couldn’t play with Willy Winky in front of Teddy and certainly not after Miss Emily had ‘talked’ to him downstairs. As it turned out this was probably just as well, because when Miss Emily came back into my room an hour or so later to check up on me she straightaway took Teddy, lifted him up to her ear again…

... then, just like she’d done downstairs, she ‘talked’ to him: “Has Scottie been behaving himself, Teddy? Has he been a good boy?” she asked.

I tried to tell Miss Emily that I had been a good boy, but she just “shushed” me to be quiet while she 'listened' to what Teddy had to say.

“He did what, Teddy? Scottie got out of bed without permission? Yes, Teddy, that was very naughty of him… very naughty…”

I must have looked shocked… which I was. How did Teddy know? No… what I meant was how did Miss Emily know? All I’d done was to slip out of bed for a couple of minutes and look out of the window… how did she know? It was no use my trying to deny it, although I’d been very careful to make sure I was as quiet as a mouse and pulled the curtains back just as they had been.

“Did you get out of bed, Scottie, when I made it perfectly clear…?” Emily paused to listen to Teddy again, “Yes, Teddy… you think so? Yes, Teddy, I agree Scottie has been very naughty and… but… well, Teddy, if that’s what you think I should do…”

I looked from Miss Emily to Teddy and back again, eager to know what Teddy was telling Emily to do. Emily was so convincing that I truly believed Teddy was talking to her. Nevertheless just like the silly schoolboy I was, my instinct was to deny that I’d done anything wrong. Me? Get out of bed? Certainly not!

“No… please, Miss Emily, I’ve been in bed the whole time… honestly,” I said, little realising how much worse I was making things for myself.

“Are you sure about that, Scottie?” Emily asked in a sly sort of voice that should have warned me she knew I was not telling the truth, “Teddy seems to think differently…”

“Honestly, Miss Emily, I haven’t moved… I even,” and I don’t know why said this, “I even kept my hands on top of the bedclothes like you said.”

It was Teddy’s turn to speak to Emily again and as she nodded in response she kept up a commentary: “I see… yes… Scottie did what… oh, yes… I see… over there by the window… Thank you so much, Teddy… What’s that… oh, don’t worry, I’ll see to that all right…”

Emily looked at me. Her eyes were positively glowing with indignation: “Teddy tells me he has proof you’ve been fibbing, Scottie…”

“... but I haven’t…”

“Don’t make it worse for yourself, Scottie. Teddy says you got out of bed and went over to the window and looked out through the curtains…”

“... I didn’t…” My head was spinning. How could Teddy possibly ‘know’ exactly what I’d done… let alone ‘tell’ Miss Emily? It didn’t stop me from digging myself into an even deeper hole than I was already in.

“Honestly… I didn’t, Miss Emily…”

“Then how do you explain that mark in the talcum powder spilt over there, Scottie?” she asked, pointing to a white patch on the floor, “You see Teddy told me that you’d peeked out of the window and you must have trodden in the powder…”

I felt my stomach turn somersaults.

“... because I can see footprints by the window… your footprints, Scottie…”

I looked to where Emily was pointing and there were smudges of white talcum powder where Teddy had said I’d been looking out of the window. I felt sick.

“Now will you tell me what you did, Scottie?” Emily said sternly.

I nodded. “I… I heard someone outside… the children who were playing outside earlier.” The children who had watched me when Emily gave me a strip-wash and put me into my new pyjamas in the front-room, I reminded myself. “... and I wanted to see if they were still looking at the house…”

“... and what did you do, Scottie?”

“I got out of bed…” I gulped feeling more like a naughty boy than a teenager of nearly sixteen.

“Despite that fact that I told you not to…?”

“Yes, Miss Emily… I’m sorry, very sorry, but…”

“Teddy says you must be punished for disobedience…”


“Teddy was very insistent. He said that as you had deliberately got up out of bed when you were told… and you fibbed saying you didn’t.”

“But, please, Miss Emily, I couldn’t help it…”

“Honestly, Scottie, you sound just like one of the little twins I used to babysit. Whenever one of them did something naughty, they would say, ‘but I couldn’t help it, Miss Emily,’” Emily paused, “But it didn’t do them any good because they both got their bare bottys spanked for naughtiness.” I must have looked puzzled, because she added, “You see, Scottie, the boys were identical twins, so I never knew which one had been naughty, so to make sure I always gave them both a smacked botty.”

“But… but, you wouldn’t smack my botty…?” I realise I must have looked and sounded totally pathetic as I pleaded with my thirteen year old babysitter.

“Why ever not, Scottie?” Emily said calmly, “Teddy tells me you’ve been a very naughty little boy… getting out of bed and then fibbing was very naughty…”

“Oh, but… please, Miss Emily…” It was really stupid of me to argue, but name me a boy who doesn’t when faced with the prospect of a smacked botty.

Emily ignored me and spoke to Teddy: “Do you think I should let Scottie off, Teddy?”

I was really worried about what Teddy would say and watched nervously as Emily held Teddy to her ear and listened.

“Hmm… really? You think Scottie was that naughty, Teddy… But Teddy, it was only the first time Scottie got out of bed without asking permission… Yes, but Teddy… hmm, I see… Yes… alright, Teddy… yes, that’s what I’ll do then…”

Without another word spoken, Emily placed Teddy at the foot of my bed, positioned him so that he was watching me, and then she left the room.

As soon as she closed the door I began to beg Teddy to tell me what he’d said to Emily. It was utterly stupid of me, I know, but I was terrified about what Emily had planned for me. Having her talking and listening to Teddy as if he was alive was… well… but how did Emily know I’d got out of bed? It wasn’t until Teddy ‘told’ her about the talcum powder… oh, it was madness… But how did she know I’d been naughty?

Teddy said nothing and I never did find out.

Teddy was still keeping his watchful eyes on me as Miss Emily came back into my bedroom. In her hand she held a hairbrush which she placed on my bedside table. She leant over and pulled my bedclothes back.

“Time to get up, Scottie…” she said.

“What… what are you going to do?”

“Teddy wouldn’t listen to me,” she explained, “He insisted you be punished for your naughtiness… If it were left to me, I’d have let you off with a warning, but Teddy says you’ve got to be taught a proper lesson…”

“Oh, please Miss Emily… don’t listen to Teddy…”

“I’m sorry, Scottie, really I am, but Teddy knows best… Teddy saw you get out of bed, Teddy saw you pull open the curtains… and Teddy saw you step into the talcum powder…”

“... but, Miss Emily…”

“Come on, Scottie… up you get… best be a brave little soldier with Teddy watching you.”

As she said this, Emily moved Teddy and put him up on a shelf so that he was looking down where I would receive my punishment. I don’t know who I was more afraid of; Teddy or Miss Emily.

Emily sat down on the edge of my bed, within reach of the hairbrush, and made me turn to face her. For a few minutes I was lectured on the subject of obedience, before she tugged the cord that held up my pyjama-bottoms. The knot came undone and Emily gently pulled the striped material. That was all it took before my pyjama-bottoms slipped down my smooth legs and fell in a puddle at my feet. She continued my lecture and then undid the lower two buttons of my pyjama jacket. Emily stood up, stepped around me and lifted up the back of the pyjama top. This she tucked into the collar, before she turned and sat down on the bed once more.

As I stood there with my boy-bits on display in front of her, Emily continued to lecture me on the dangers of getting out of bed without permission, telling me I might have tripped and fallen in the dark; how I could have slipped and knocked something over. What did I think I was doing disobeying a perfectly clear instruction?

All the time I could see Teddy out of the corner of my eye watching me being ticked off.

Miss Emily had perfected the art of the lecture, no doubt she had plenty of practice on those two unfortunate boys, the twins she babysat before answering mum’s advert. In the end I was near to begging Emily to get on with it. My sense of shame was heightened to an unbearable degree.

Finally Miss Emily patted her knees and told me it was time for me to learn my lesson. I followed her instructions and positioned myself across her lap. Emily might well have been only thirteen years old, but she had no difficulty in dealing with this fifteen year old boy. I found myself with my toes barely touching the floor, whilst my head was all but pressed into the bedroom carpet. This left my bare bottom perfectly presented for Miss Emily’s attentions.

As I quivered with anticipation Emily continued to admonish me as she made final adjustments to my position across her lap.

“Now, Scottie, I want you to remember that it was Teddy who asked me to give your naughty botty a smacking because you got out of bed… Do you understand?”

“Yes, Miss Emily…”

“... so I’m going to let Teddy decide how many spanks your botty deserves…”

“Yes, Miss Emily…”

“... but remember, Scottie, Teddy was very upset and very annoyed with you…”

“Yes… yes, Miss Emily..”

“I think the least you can do is to say you’re sorry to Teddy… Do you agree, Scottie?”

“Yes, Miss Emily….” I twisted my head sideways and looked up at Teddy who was staring down at me draped over Emily’s lap, “I’m sorry, Teddy… I’m sorry I got out of bed, Teddy… I promise I won’t do it again…”

“That’s a good boy, Scottie… I’m sure Teddy will make sure you keep your promise. Now I think we’d better get on with your spanking, don’t you, Scottie?”

“Um… um… yes, Miss Emily.”

That was the last comprehensible word I spoke.

I don’t know how Miss Emily learnt to wield the hairbrush with such precision, but it was extremely effective. Within minutes I was wailing like a banshee, pleading with her to stop, although my words were quite unintelligible.

It wasn’t much longer before my eyes were full of tears and I was crying like a baby, but apparently Teddy was not satisfied that I had been sufficiently punished.

“Teddy says you are wriggling far too much, Scottie,” Emily said as she continued with my punishment, “Teddy says you are to keep still for your smacks…”

But it was impossible for me to keep still. The hairbrush spanking was unlike anything I’d experienced before. I couldn’t control myself. I continued to wriggle and cry my eyes out. I bawled and sobbed, but it made no difference to Miss Emily who I reckoned must have been the strictest babysitter that ever lived.

And still Teddy was not satisfied that I had been sufficiently punished.

By now my nose was running and snot was dribbling over my top lip which I was quite unable to wipe away. Although the mess of mucous tasted horrible, it was the least of my concerns as I jerked and bounced about under the torrent of smacks from Miss Emily’s hairbrush.

There was a pause in the barrage of spanks while Emily ‘consulted’ Teddy.

“... I see… yes, Teddy, I know it was very naughty of Scottie, but you can see how he’s crying his eyes out like a little baby… surely that’s enough? Really Teddy! Oh dear me… well, if you say so… yes, I know Scottie has to be taught a lesson in obedience… very well then…”

Miss Emily addressed me: “Scottie, Teddy says I’m to give you a hand-spanking on your bare botty…”

“Oh, please, Miss Emily…” I sobbed and begged to be let off any further punishment of my red-hot bottom. The thought of even a hand-spanking on top of the hairbrush smacking made me plead shamelessly with my strict babysitter.

“I’m sorry, Scottie, but Teddy insists… and as he saw you get out of bed without permission, it’s only proper that he decides when you’ve been punished sufficiently…”

I felt Miss Emily’s hand rub against the tops of my thighs and across my bottom as if she was trying to find the right place to start my spanking. If I’d have given it any thought I would have felt enormous sympathy for the boys Miss Emily used to looked after. What was it she said? If one of the twins misbehaved, she gave both boys a smacking on their bare bottys? I wonder if they had a Teddy to keep watch over them?

The hand-spanks started, and soon enough I was twisting and wriggling over Miss Emily’s lap. Her hand might have been small, but it seemed to seek out all the little places that had somehow been spared the hairbrush.

Finally… finally Teddy was satisfied I had been properly punished. I was made to tearfully apologise to Teddy and to promise not to be naughty. Miss Emily fetched a wet face-cloth and wiped my face before sorting out my pyjamas.

“I… I’m sorry, Miss Emily…” I said as my pyjama bottoms were pulled up and the white cord tied up again. Fortunately the soft nap of the winceyette didn’t  hurt my bottom too much.

“Let that be a lesson, Scottie,” Emily said as she brushed my ruffled hair straight, “Be grateful it wasn’t worse…”

WORSE!! I thought… what could possibly be worse?

“Let’s get you back into bed, Scottie… You should have been fast asleep ages ago…”

This was said as if nothing had happened.

“Please, Miss Emily, may I sleep on my tummy?” I asked, “My botty is still very sore…”

“Hmm… very well,” Emily said with more than a hint of kindness in her voice, “but put your hands on your pillow… that’s right, either side of your head.”

“Thank you, Miss Emily… I will be a good boy,” I promised.

“I should hope so, Scottie… Now settle down and go to sleep,” Emily said as she tucked me in and placed Teddy next to my head, “Teddy will look after you… nighty-night.”

Miss Emily turned out the light and left my bedroom. I looked at Teddy through my still damp eyes: “I’m sorry I was naughty, Teddy…”

I drifted off to sleep still none the wiser as to how Teddy knew I’d been naughty and crept out of bed earlier...