The First Letter to David

Stephanie looked at the letter she’d just finished writing. It was addressed to a sixteen-year-old schoolboy by the name of David who was the son of Stephanie's dear friend Margot Widnes. The letter was a record of the events which took place the previous day at David’s house when the sixteen-year-old had been taken to task by his mother for failing to take his schoolwork seriously.

Stephanie was sure David would rather forget about what had happened, which was quite true, but Stephanie had other ideas. She decided to put into writing exactly what occurred, so that the boy had a permanent reminder of what to expect in future if his behaviour didn’t improve.

The letter is self-explanatory, but it will help the reader if it is put into context:

David had been told by his mother to report to the living-room at three o’clock sharp for a 'talk'. Unfortunately for David this was precisely the time at which Stephanie had decided to call on her friend Margot. Stephanie had just sat down with Margot to catch up on each other's news, when in walked David.

As David entered the room Stephanie was astonished to see the sixteen-year-old was dressed in full school uniform which included a blazer and school cap. Stephanie was even more surprised when she saw David was wearing a pair of short grey school trousers that bared the boy’s thighs right to the top of his long smooth legs.

It became apparent to Stephanie, as she watched David being given a stern dressing-down, what was about to happen, so she volunteered to leave and allow Mrs Widnes to deal with her son in private. But Margot Widnes said she wasn’t in the least bothered about Stephanie staying to watch ‘how we deal with naughty boys in this house’ and insisted her friend remained.

Stephanie looked at David standing in front of her dressed in his school uniform. She could tell by the way the sixteen-year-old avoided eye-contact and shifted his weight from one foot to the other that he was very uncomfortable indeed about Stephanie being there. But the boy knew it would do him no good to complain.

Stephanie saw what was going through the boy’s mind and therefore decided that it was her duty to remain, however onerous that duty might prove to be…

My dear David (the letter began),

I am writing to you because I want you to understand what it was like to watch you yesterday afternoon as you were reprimanded by your mum.

In doing so I want you to appreciate that I have the full agreement of your mum who feels that your future behaviour may benefit from having a complete record of what I witnessed yesterday. I need hardly add that I shall expect you to keep and look after this letter as you may well be asked to produce it at some future date.

No-one who saw you being dealt with could say that it was in any way unwarranted. You had been told before on many occasions that your behaviour was becoming unacceptable.

I can only hope that you’ve learnt your lesson and that is why I’m taking the trouble to write this letter. It is intended to be a record of all that happened; to remind you of what will happen if you are naughty in future.

From the moment you walked into the living-room yesterday David, I found it hard to believe I was looking at a sixteen-year-old boy. From what your mum told me, you’ve been acting more like a twelve-year-old. Perhaps that’s why you reminded me of a twelve-year-old yesterday, David. Do you really want everyone to think you’re only twelve-years-old?

I’m sure I could have been forgiven for thinking you were indeed younger than your sixteen years when I saw you yesterday afternoon, as I had no idea older boys were dressed in short trousers for school these days. Yet there in front of me was a boy of sixteen dressed in short grey school trousers, long grey school socks, tan T-bar sandals, grey Trutex school shirt and brightly coloured red & gold school tie. To complete your school uniform you were also wearing your school blazer and cap, both red with gold piping. And very smart you looked too!

The short school trousers were very short and I noticed how your smooth thighs were bare almost right to the top. I could see these very brief short trousers caused you an immense amount of embarrassment by the way you kept glancing at me as I looked at your bare legs. You have lovely legs David and I shall speak to your mum and see if we can't keep you in short trousers for school for a little while longer. It would be such a shame to hide your beautiful smooth legs away in long trousers.

Your mum did tell me that you’ve pleaded with her on several occasions to be allowed to wear ‘longs’ out of school, but she said that while you behave like a fractious little boy, then you will be treated just like a little boy. And little boys as you know wear short trousers, don’t they David?

You were already red-faced when you were called to stand in the middle of the living room front of us, David. I little realised that you must have known what was going to happen. Your mum told you to put your hands at the back your head and that’s when I saw you rub your bare thighs together in anticipation of what was coming.

You squirmed with embarrassment when you found out that I was going to stay and watch. I looked up at you, but you avoided my eyes as you coyly looked at the carpet at your feet. You must have known at that point you would be getting a much closer look at that carpet later! Try as you might, you couldn’t stop blushing in front of us because you knew what was going to happen next.

First you were told to remove your school blazer, but to keep on your school cap even though normally boys aren’t allowed to wear their caps indoors. Then you had to return to the middle of the room facing us and put your hands back behind your head.

I smiled as I saw your mum put a hand around the back of your bare legs and pull you towards her. Did I notice you try and stay where you were, David? Maybe, but not for long, as mum is clearly very used to dealing with silly behaviour like that, isn’t she? Yes she is, because you felt a sharp smack on your thigh, didn’t you David? A very sharp smack which was so loud and unexpected it made me jump. It made you jump too, didn’t it David? I bet it really stung because I could see where your mum’s hand had left a bright red mark on your leg. You certainly moved quick enough after that smack to where your mum wanted you to stand!

And why do you think your mum wanted you to stand closer to her? Was that why you tried to stand your ground? You knew, didn’t you David, that mum was going to take down your short trousers and you didn’t want me to see you standing there like a little boy with his trousers down. In that case you had your thigh-smack for nothing, because I watched as your mum’s hands came up to the waist of your short trousers.

I wonder what it was like when you felt mum’s hands pressing against your tummy as she undid the clip at the waistband of your short trousers? I think you were very silly to wriggle as you must have known what would happen. Three more smacks on your legs made you yelp and look even more like a twelve-year-old than ever. You bit your bottom lip as though to stop yourself from crying, but I was pleased to see you kept your hands on your head where they were supposed to be.

I had to remind myself that I was looking at a sixteen-year-old, but it was very difficult David. You looked so contrite as you stood with red smack marks on your bare legs, biting your lower lip as you struggled not to cry in front of me and your mum. You looked nothing like the sixteen-year-old boy I had been assured you were. At that moment, as you stood obediently in front of your mum, waiting for her to take down your little short trousers, if I’d been told you were sixteen-years-old, I’d have said: “but he can’t be… surely not. Sixteen?! I don’t believe you… Sixteen?! Never! Why, he looks just like a twelve-year-old…”

Yes that’s exactly what you looked like, David… a naughty twelve-year-old schoolboy. A naughty twelve-year-old schoolboy who’s about to have his short trousers taken down by his mum. I wonder how you felt. You must have been very embarrassed having me watching you because I could see your eyes as they glanced my way, to see if I was looking. Oh I was looking alright, David, watching everything that was happening; looking at those lovely red smack marks on your legs and wondering if they were still stinging; waiting to see what would happen to your school uniform; thinking about how many items of your school uniform would be removed. You see at that point I didn’t know what your punishment would be, David. But I could see that you knew what was to happen.

I imagine that must have made things a whole lot worse for you, knowing what your mum was going to do… only this time it would be done in front me. Did that set off the butterflies in your tummy, David? You certainly shivered with embarrassment and bit harder on your bottom lip as you felt your mum’s fingers pulling at the zip-fly on your short trousers. I smiled as I heard the soft buzz of the zip as it was pulled downwards. Could you feel the pressure of your mum’s fingers on the front of your short trousers as they gently tugged at the little zip? I bet it felt as if you’d reached the point of no return. You knew then that I’d see you having your trousers pulled down, pulled right down, a boy’s worse nightmare. Yes, David you knew that I was going to see you with your trousers down around your ankles.

But let’s not get ahead of ourselves shall we David?

You know what happened next, don’t you David? Yes, another leg-smack! How silly you were David. Fancy pulling away from mum as she was about to open the front of your short school trousers. You know she has to loosen the front of your trousers before she can pull them down. It was your own silly fault your mum had to smack your legs again. Only this time the smacks were much sharper, real stingers. I could see that by the way you jumped and yelped. A sixteen-year-old boy? A silly little twelve-year-old, more like. Smack! Smack! Smack! Your mum certainly knows how to smack bare legs, doesn’t she David?

I could see that your eyes were damp as you stood still, waiting to have your trousers taken down. With both legs red from your mum’s smacks, what a sight you presented! Your nose began to dribble, but wisely you kept your hands on your head. Again I had to remind myself that you were sixteen-years-old and not twelve as you looked, standing there in your mum’s living-room.

Finally mum pulled open your short trousers so that I could see the white polyester lining. And that’s not all I could see, was it David? No, because when mum pulled open your school trousers she undid the bottom two buttons of your grey school shirt and pulled your shirt-tails apart so that I could clearly see your underpants. They weren’t just any old pair of underpants either, they were white cotton, school uniform underpants, weren’t they David. That any boy of sixteen should still be wearing school uniform underpants was unbelievable! Surely no self-respecting sixteen-year-old boy would dare to be seen in white schoolboy underpants! Yet there you were David, standing in the middle of the room, plainly wearing underpants that no boy over fourteen would be seen dead in!

What were your thoughts as you felt your mum’s fingers slide up the outside of your legs, David? I almost felt sorry for you as I looked at the expression on your face. A trickle of snot had dribbled down onto your upper lip and I could see you so wanted to twist your head and wipe it off onto your shirt-sleeve, but wisely you didn’t. You looked so desperately uncomfortable and I could see the glistening, viscous mucus was tickling you so much that I decided to wipe your nose for you.

Your mum paused with her fingers tucked inside each leg of your short trousers. Her thumbs gripped the outside of the legs. She was ready to pull your school trousers down. I got up and stood at your side. You looked at me David as I placed my left hand on the nape of your neck. It was like I was about to wipe the runny nose of a junior schoolboy and again I had to ask myself if I was really holding the head of a sixteen-year-old boy? Your face was so smooth, David. As my fingers brushed your chin and your upper lip, I felt your soft skin and wondered how long it would be before you needed to shave. A year? Eighteen months? Longer? Whichever way it would be a long time before this teenaged boy could claim to be anywhere near grown-up.

I wiped your upper-lip and then placed the tissue over your nose. I gently squeezed your nostrils and spoke: “… let’s have a big blow David and we’ll have a nice clean boy… good and another one to make sure… that’s a good boy…”

I wiped your nose again before I sat down again. Luckily for you David you remembered to thank me, or I’m sure your mum would’ve had something to say.

Then it happened, the moment every schoolboy dreads. Your mum’s fingers still gripped the legs of your short trousers, then, with a gentle but firm tug, mum pulled your short trousers down over your bottom. She held onto them as the unzipped front opened out wider to give me an excellent view of your school underpants. Now I could see the boy bulge that pushed forward and it was plain to see that your underpants were designed for younger boys than you David. On you, schoolboy underpants looked to be embarrassingly small. Maybe that’s how they are supposed to look. But you didn’t look at all pleased to have them on show so that I could see them.

Your mum paused leaving your short trousers hanging precariously at the top of your legs. As I said, your tight little schoolboy underpants were now on display and I wondered what mum was going to do next.

Mum pulled you closer still. This time you behaved yourself and escaped anymore leg-slaps. Now you were close enough for her to reach up and finish unbuttoning your grey Trutex school shirt

One by one your mum unbuttoned your school shirt from the bottom up and that’s when I had my next surprise… you were wearing a vest! A white cotton school vest tucked neatly into your underpants. I could hardly believe you could look anymore like a junior schoolboy than you were already, but now… now that I could see you were wearing a school vest…

I was distracted from my thoughts as your mum told you to turn around. Your grey shirt was hanging open giving me a tempting glimpse of your white school vest. Your red and gold school tie was properly knotted so that your shirt collar was nice and tight, the collar button still done up. You shuffled, careful not to let your short trousers slip any further down, until you faced away from us. Without more ado mum took your shirt-tail, pulled it up your back and tucked it into the back of your collar. Next you were told to turn back round.

I knew you were in serious trouble David, but you looked so funny standing there in front of us with your hands still firmly pressed against the back of your head. Really, David I had to stop myself from laughing out loud because now, with your grey school shirt pulled right open, I could see your white school vest and underpants were just like a twelve-year-old boy would have to wear to school. Like I said, you were still wearing your school tie and it hung down looking quite silly resting on top of your vest. Looking down I could see that your short trousers were only just clinging to your bottom. Of course, below your smooth thighs, below your bare knees were your long grey school socks with red and gold rings, your school colours, around the turnovers. And on your feet, those juvenile-looking T-bar school sandals.

What happened next David? Well we all know don’t we? Yes, it was time to take down your trousers. Once more I could see you bite your lips in apprehension as you watched your mum take hold of the hem of your short trousers. With one gentle tug to each leg we watched as the trousers tumbled down your legs to land in a crumpled heap around your ankles.

I was quite surprised when at that point your mum stopped to ask me if I would like a cup of tea. I’m sure you remember how she explained that she always liked to have a break and stop for a cup of tea when she was getting you undressed and ready for one of her little ‘talks’ with you.

And perhaps it is the right time for me to pause and bring this letter to a close, David. Do remember though, this only describes the first part of what I saw happen to you yesterday.

I shall continue in another letter and remind you of how I saw your underpants being taken down by your mum and how I got to see… well, you know what I saw David…. and very embarrassed about it you were too!

Yours affectionately,

Stephanie