Andy was eleven and a half years old in the summer of 1991 and had enjoyed the holidays. Now they were almost over, though, and the time had come to buy his uniform for the new school year. He was just over 5ft tall, an average height for his age, and his mother had been complaining at the rate at which he'd gone through pairs of trousers last year, as he had been out of school shorts since then. He attended a quite traditional prep school which was very strict on uniform, and Andy secretly wished that he had not bowed to peer pressure and worn longs the previous year. He remembered how smart he had looked in grey shorts and kneesocks, and how free he felt dressed like that. The white lining made them extremely comfortable and they were tough enough to last for ages, which would please his mother.
"Mum, could you get me shorts for school instead of trousers?" Andy blurted out in the car on the way to the outfitters. He had been thinking this over for days and had decided to risk the teasing of his friends.
"Good Heavens, Andrew, what a surprise! Are you sure? You won't be able to change your mind once they're bought, you know!"
"Yes Mum. They're smart, comfortable and cheaper. I don't mind as I won't be the only one in them this year." Which was true, a small number of boys always wore shorts and nobody teased them about it.
Three pairs of shorts were duly purchased, reaching to about four inches above the knee, along with the necessary kneesocks to go with them, which had red bands around the top. He also had a new red blazer with the school crest on the breast pocket, and found himself almost looking forward to the first day of the new term. He was determined not to put up with any laughter or joking about his appearance.
The last week of the holidays passed too quickly, as it always did, and one Monday morning it was time to get up and get ready for school. After a cursory wash, he put on his underwear and then the socks, quickly pulling them up to his knees and folding down the tops so the red bands were clearly shown. His grey shirt and tie followed, until finally he reached into the open drawer and took out the shorts. As he pulled them on he couldn't believe how good the white lining felt against the skin of his legs. After adding pullover, also with red bands around the V-neck, and shoes of course, he took his blazer out of the wardrobe and put it on, stepping back to admire his reflection in the mirror. He looked and felt great. The jeans that were his standard home wear lay forgotten on the floor where he had casually kicked them off the night before, joining the mound of other casual clothes waiting for his mother to pick up, which he knew she would.
Andy had spent too long getting ready, so he wolfed down the usual tea and toast without saying much to either parent but he could tell they were impressed by his appearance. He knew his father wouldn't say anything as he was too busy getting ready for work himself, so his mother's "You look nice, dear" was the only comment. This was OK with him, and he grabbed his school bag and ran out the door. His prep school was only a mile away and he always cycled there, so he flung open the garage door, grabbed his bike and pedalled for all he was worth. Corporal punishment had been abolished at his school years before, so he wasn't worried about getting caned, but he could do without a detention on the first day back, he thought.
He arrived just in time and joined the stragglers going into the cloakroom to put their things away before assembly. He met his best friend Peter almost straight away, who choked on the "Hi" he had been going to say and looked at his shorts in surprise.
"Did your parents make you wear those?"
"No. I decided to do it. I like them and they're good for messing around in."
"You didn't say anything about that when I came over on Saturday! They make you look like you're really junior. Still, Henry, Tim and Alan are wearing them so you're not alone in our class." And with that the new term started. Others of his friends made similar comments but nobody really had a go at him. He settled in and forgot about it.
After a long and very average day at school, finally the going-home bell rang out. With a sigh of relief, for the last lesson was Geography (which he hated) Andy stuffed his homework into his school bag, said goodbye to Peter and the rest of his friends, and ran to collect his bike. He rode home as fast as he could, not because he was late but because it was windy and raining and he wanted to get there.
His mother had his tea ready. "Not so smart now, I see, shorts or not!" she smiled, noting his dishevelled appearance. He smiled back and tucked his shirt in haphazardly as he stuffed a jaffa cake into his mouth. "Your jeans are washed but they're not dry yet." she said as he sipped his tea. "Don't worry, Mum, I'll keep my uniform on today." he replied, which surprised her but she made no comment.
"Your father and I are going out this evening. He has a new manager at the office and we've been invited to dinner. It has all been very sudden and a bit awkward, really, as your usual babysitter's busy."
"Mum, I'm too old for a babysitter."
"Well, that's as maybe, but we've managed to arrange one. It's very kind of him, too, at the last minute like this."
"Who is it?" Andy asked resignedly.
"One of the clerks at your dad's office. His name is James Roberts and he'll be coming home with your father later. Now, finish your tea and go and do your homework."
Two hours later, and with Maths and History homework done, Andy stretched out and put a CD into his stereo, which sat on a shelf over the desk in his bedroom. Turning the volume quite low, he leaned back into the big executive-style desk chair his dad had bought him a few months ago, and shut his eyes.
Fifteen minutes later he was woken by his mother's voice. "Andrew, come down here and meet James."
"Coming, Mum." he replied sleepily, and slid out of the chair. Turning off the stereo, he shook himself awake and took a long drink from the coke can on his desk. Tucking in his shirt, again, he went downstairs. In the hallway was a man of about 30, Andy guessed. He was of average height and build, had short dark hair combed into a straight parting on one side, and wore a new-looking business suit.
James smiled as Andy walked up to him. "Hello there. Andy, I believe."
"Yes, Hi"
"I'm sure we'll get on fine."
Andy' father looked at his watch. "Hurry up, dear", he said to his wife, "we'll be late." With that, they left. Mum must have got ready while I was doing my homework, Andy thought. He turned to James, who was looking at him.
"Want to watch TV?"
"OK. What's on? I like your uniform by the way. Very traditional and proper for a boy your age."
"Er.... thanks." Andy was a bit taken aback. "I'll look at the Radio Times".
He walked into the sitting room, followed by James, and they both sat down on the sofa. Andy picked up the magazine and turned to the relevant page. "There's not much on except soaps and sitcoms." he said. Despite this, they both sat there and watched the screen blankly for a good half hour before James looked at the clock and said "It's about time for dinner, I think. Your mum left it out ready to re-heat. It'll only take a few minutes in the microwave."
He disappeared into the kitchen. There was the usual sound of food preparation, and ten minutes later James reappeared with two trays balanced rather precariously in his hands, wobbling slightly. The kitchen door was behind the sofa so Andy didn't see him come out, and just as James turned to hand the tray to him, he stood up and knocked it flying, all over the babysitter's new suit.
"Sorry, James" he said, and meant it. "I'll get a cloth."
"Yes, you better had."
The clean-up was less than perfect, but would have to do. Afterwards they shared the one remaining dinner between two plates and ate the somewhat cold remnants of it in an uncomfortable silence. Eventually they finished and plonked the trays on the coffee table.
"When I was your age I'd have got a spanking for that. My dad would have used his hairbrush. Hard."
Andy looked at James in surprise. What a thing to say! Still....
There followed another awkward silence, during which Andy thought carefully. He had often wondered what it would be like to be properly spanked. His school didn't use the cane anymore, of course, and his parents would never dream of hitting him, so he always assumed that he would never find out.
He reached a decision and took a deep breath.
"I'm very sorry for ruining your suit, James, and I'll take a spanking. I'll go and get my dad's hairbrush."
He got up and went out to the hallway. James's eyes widened in absolute astonishment. Andy couldn't possibly have guessed, but he was an enthusiastic, if secret, participant in adult role-play spanking. Although he didn't really agree with the use of corporal punishment at school (except as a last resort) or especially in the home, to spank a real boy dressed in grey shirt, grey school shorts and kneesocks (now around his ankles, of course) was a chance he didn't want to miss. He would never normally dream of doing such a thing, but there was a legitimate reason to be angry and, well, the boy seemed to have volunteered!
Andy walked back in carrying the hairbrush, and handed it to James. It was wooden, quite heavy, with a long 7in handle and a business area about 4in square, James saw. Perfect for spanking. "Andy, are you sure about this? You certainly deserve punishment, but it's not really my place to spank you."
"Yes. Don't worry, I won't tell my parents and I'll make sure no-one sees the marks."
I just don't believe this, thought James. He collected his thoughts. "Well, OK then. But I warn you, it'll be a proper long spanking and it will hurt a lot."
"Oh. Er... I know. How many whacks do I get?"
"About a hundred and fifty, probably. I can't be exact."
A hundred and fifty? For a split second he thought about refusing to go through with it, but that would be missing his chance. He took another deep breath.
"I'll do whatever you say."
James moved to the middle of the sofa and sat on the edge, holding the hairbrush tightly. "First of all, pull your socks up! That's right. OK, lie across my lap and put your hands on the floor in front, with your head down as far as possible."
Quivering slightly, Andy did as he was told. James moved him forward slightly so that the tightly stretched seat of Andy' shorts was raised against his legs, paused a second, and brought the hairbrush down on the left of the boy's bottom with a resounding crack.
"OW!"
Without more than a second or two between each whack, James brought the hairbrush down again and again, spanking each side in turn.
"OW OW AAAHHH OW OW OWWWWWW". Tears were beginning to leak out of the corner of Andy' eyes.
After a minute or so James stopped, shifted Andy a bit more forward, took a tighter grip on the handle and applied himself with renewed vigour to the boy's bottom. This time, though, he concentrated on a single spot on each side, whacking it up to six times in succession, before moving to a different spot. Andy howled.
"AAAAAAAAOOOOOOOOWWWWWWWWWWWW AH AH OWWWW" he cried, tears now streaming down his cheeks. He couldn't believe the pain and that he had allowed James to do this.
The rhythm of whacks and cries continued for over two minutes more. James was determined to spank Andy soundly and left no part of his bottom untouched as the hairbrush cracked down hard all over the seat of his shorts, six times in one place, four in another, five somewhere else, leaving Andy weeping loudly, tears dripping onto the carpet.
James stopped. "Stand up."
Andy slowly and painfully levered himself off James' lap and stood up, as did James himself. He looked at him through his tears, breathing heavily.
"Twenty more to go. Face the sofa, take your shorts and underpants down and bend over, putting your hands on the seat and your head right down between them."
Andy couldn't believe that he was going to be beaten on his bare bottom. "My bottom hurts, James!" he cried. "No more, please, not on my bare bottom."
"Silence! Bend over!"
There was no point arguing further. Snuffling, he meekly stood in front of the sofa, undid the clasps at the waist of his shorts, undid the zip, and let them drop to his ankles. He then slid down his underpants to meet them and bent over for the rest of his punishment.
"All the way over, Andy, with your head touching the seat like I said." The boy complied, breathing heavily, and waited for the spanking to start again. James folded Andy's shirt tail onto his back and out of the way, took up position behind him, and looked at his bottom. It was deep red all over, with several shiny areas that were beginning to darken into purple bruises. He selected one of these in the centre of the left cheek, changed his grip so that he was holding the handle as low down as possible, raised the hairbrush over his head, took aim, and brought it down hard. Andy responded with a high-pitched howl of pain.
"AAAAAAAAAAAHHHHHHH"
James beat Andy slowly and methodically, two whacks on one cheek followed by two on the other, until all twenty had landed. Each was very hard and in almost the same place as the previous one on that side, leaving a big deep bruise, already going black at the edges, in the centre of each. Andy cried uncontrollably, wailing more loudly each time the hard wood struck his bottom, but managed to stay in position by pressing his head into the cushion and digging his fingers into it. Finally it was over and Andy crumpled into the sofa, sobbing, his shorts and underpants falling from his ankles into a crumpled heap. He stayed there for a good five minutes.
"Are you all right?" asked James, at length, when the crying had reduced to sniffles.
"Yes, I'm OK. It feels like my bottom is one big bruise."
"You're not far wrong! You took it very well. You probably need to get yourself a drink and go upstairs now, though, and get some sleep. Clean yourself up in the bathroom, have a look at the marks, and think about how you're going to manage to sit down at school for the next few days!"
Gingerly, Andy sat up on the sofa. "Yes. OK. Good night, James."
"Good night, Andy. I'll tell your parents that it was me who spilt the food, and I'll pay for the dry cleaning myself. I think you've had enough punishment without losing pocket money too!" He grinned at Andy, who grinned back. See you on the CP scene in a few years time perhaps, thought James, making a mental note to get discreetly in touch when Andy turned eighteen.
Slowly, Andy reached for his clothes and stood up, gasping from the pain of the bruises as he moved. He pulled on his pants and shorts as gently as possible but they still rubbed against his bottom.
"OW!"
His eyes watered again, and he angrily wiped the tears away as he limped to the kitchen, rubbing his bottom gently with his right hand. Now he knew what it felt like to be well and truly spanked!