It all started about ten minutes into the PE lesson. Maybe because it was a cold day and they were outside on the rugby pitch, or maybe it was those eggs which Tim had for breakfast, but he was suddenly aware of a griping pain in his stomach, and he clutched it as he ran towards the ball.
“Clark!” shouted the PE master, Jones, “What’s up with you?!”
Such sympathy, thought Tim, as he doubled over in pain. Jones jogged up to him, frowning,
“Spot of trouble?”
Tim nodded weakly, his head swimming. Jones commandeered Wiggins, a pale spotty boy, and gave him orders to take Tim to the sickbay, no dawdling. As Tim shuffled off the pitch, he thought to himself he must look rough, if Jones had not even questioned him.
Tim’s thoughts turned to the sickbay, in a small building in the corner of the grounds. He was not an infrequent visitor, but seeing the Assistant Matron, Miss Cartwright, often helped him feel better. Miss Cartwright was the subject of half the school’s dreams. She looked like she’d walked off the set of one of the American films they watched at weekends, coiffured brown hair set in waves on her head, spilling in curls down her neck. She had large eyes, rosy cheeks, and a beautiful smile. Her legs did funny things to his insides, as did the swell of her breasts under her tight uniform. Wiggins knocked at the sickbay door and a loud, deep voice shouted “Come in!”
Wiggins pushed the door open and then ran off.
“Don’t just stand there, boy, come in,” barked the voice and in one second Tim’s hopes of seeing Miss Cartwright were destroyed. It was Matron. Matron was in charge today and Miss Cartwright, her deputy, wasn’t there. He looked at her in disappointment. A large, plump lady of – he guessed – about 60 – he didn’t know women’s ages but she was definitely older than his mum. She had short, no nonsense salt and pepper hair and a fat face with dark beady eyes under thick grey eyebrows. No big red lips like Miss Cartwright’s. Just a large, ugly mouth without lipstick.
“Right then!” she barked, sitting up and giving him the once over. “What’s the matter with you?”
It only occurred to Tim long after he’d left school, that the usual way they were treated was not the nicest way to treat young boys. Matron seemed to doubt any boy who came to her, as if all of them were skiving. Naturally, some were, but in cases of obvious illness, each boy was still given the third degree. Tim managed to say what was wrong with him, as his stomach was still churning. Matron sent him off to the toilet and when he returned, no better, she took his temperature. So brisk and business like, none of the tender caring which a sick boy might expect from his mother. She looked at the thermometer.
“Ok, you’ve got a temperature. I’ll give you some painkillers. You can go through and lie down for a while. There’s no one else here. Take your boots off and don’t get mud on my bedspread. There’s a set of pyjamas in the cupboard. I’ll be in to check on you in a while.”
Tim swallowed the tablets, and then went through to the bedroom. He got changed and climbed into the comfortless bed, pulled up the blankets and settled down for a rest. It was very quiet and he soon felt warm and sleepy. He wished Miss Cartwright had been there. As soon as he thought of her, his cock stirred and he reached down a hand and put it down his pyjamas. Slowly touching it, he played with the shaft, and twirled his hand around the head. It grew in his hand and he thought of Miss Cartwright and how lovely she would have been if he had told her that he was ill. Soon he was stroking it rhythmically as he imagined her soothing him, a hand on his head, then a cool kiss on his forehead as she tucked him in. He was pulling at his cock now, it was standing up straight and hard and the more he imagined the more aroused he became and it was really lovely now thinking of her, feeling this excitement, imagining her here, and –
“You boy! What DO you think you’re doing!?” came a shout, and Tim’s hand shot out of the bed, his face flushing, his fantasy rudely interrupted. Matron strode over to the bed, flung back the covers and stared at his cock which was quickly shrinking.
“How dare you!” she shouted, making him blush harder. “In my sick bay! Revolting little boy! Get up!” She grabbed him by one arm and thrust him to one side of her. “I’ve never seen anything so disgusting!” she went on, as if boys and their bodies were a mystery to her.
“Sorry Miss!” he spluttered, wondering what she was going to do. She was red in the face and seemed horrified at what Tim knew every boy in his dorm did, at least once a night.
“I’ve never seen anything so disgusting!” she boomed. “It’s a filthy habit! I suppose you do it all the time?!” she asked. Tim shook his head, he wasn’t going to tell her how often he did do it.
“There’s only one treatment for this,” she growled, looking into his face. Tim wondered what revolting medicine she was going to shove down him. “Dirty boys who touch themselves need a good long spanking! Don’t they!”
With those awful words, Tim’s stomach lurched and his head spun. A spanking?! At his age? He’d been caught a couple of times doing things he shouldn’t have, such as scrumping apples and teasing the caretaker’s cat, and these things had been duly punished – but that was by the headmaster in his study, with a slipper. Not a spanking like his mum might have given him when he was little.
“I’m not a baby!” he complained but Matron wasn’t listening to him. She sat squarely on the bed.
“Right,” she declared, “Get over my knee!” and with her big beefy arms she hoisted poor Tim into position over her lap, so that his feet were dangling and his bottom was sticking up. With a big fat hand, Matron began spanking poor Tim.
“Oww, oww!” he called as the first smacks made contact. He did not want to let her know he was bothered but the smacks caught him by surprise. She spanked hard and fast, without a warm up. Tim wriggled to make it harder for Matron to spank properly.
“Keep still!” she ordered and pinned Tim’s legs under one of her enormous thighs. Tim could not move now and the spanking went on and on, the smacks fell harder and harder, stinging his bottom through the pyjamas. He felt his buttocks itching, a curious sensation, and each smack stung like wasps. Matron took hold of his pyjama waistband and she pulled them down to expose his bare bottom. The sore skin felt hot against the cool air. Matron began spanking again. Tim screeched as the smacks fell on alternate cheeks, and he kicked his legs against this unfair assault.
“This will teach you,” she said, as she kept spanking. “Only naughty boys touch themselves when they’re in bed.” She smacked on and on. “Naughty boys need their bottoms spanking, don’t they?” and she kept on spanking. “Only a good long spanking will teach you a lesson!” Tim was breathing loudly as he focused on holding it together. Each smack hurt more on tender skin and each smack echoed. Tim listened to the echo to distract himself, as his head got lighter and his bottom got numb. With a final flurry of stinging smacks, Tim let out an angry yell and finally it stopped.
“Get back into bed and keep your hands above the covers!” ordered Matron and she swept out of the room.
Tim stood in shock by the side of the bed, clutching his bottom. He craned round to try and see if it was red. The skin burned and felt hot to the touch and now he was alone he let his tears come. He didn’t once question if this was okay, if Matrons in charge of sick boys at school should be allowed to spank them, but he felt mortified at being caught by her and would have to make sure his friends did not guess. He pulled up his pyjamas carefully and lay down in bed.
A little time went past and he must have been dozing, before the click of the door woke him up. He held his breath and shut his eyes, determined Matron would think he was asleep. But something in the way the person came in told him it was not Matron. Whoever it was didn’t enter like a bull, snorting and puffing. There was a softness, a scent of flowers, someone… someone nice. He opened his eyes. Standing next to his bed, head bent lower to see his face, was the beautiful Miss Cartwright.
“Shhh, go back to sleep,” she cooed. “It’s okay.” She put a soft white hand on his forehead, and brushed the blond hair out of his eyes. With that one gesture of compassion, Tim burst into tears and the pain and frustration of the spanking overflowed. Miss Cartwright was alarmed.
“There now, whatever’s wrong?” she asked with concern, sitting down now next to him on the bed, her firm thighs alongside his own leg. He could barely speak.
“Tim, darling, what’s the matter?” He sat up and Miss Cartwright put her arms round him and held him tight in a hug. Tim found his face pressed into her breasts and breathed in a wonderful smell, of freshly baked biscuits and flowers. His sobbing stopped and he felt calm. She patted his back and made soothing noises, stroking his hair. Tim felt much better.
“What happened?” she asked, but Tim was too embarrassed to mention his spanking. She knew anyway. Matron had told her, he presumed. “Is it sore, after your spanking?” she asked softly. He nodded, going red. “May I see?”
Tim went the colour of beetroot. But Miss Cartwright was so gentle, he couldn’t resist and she turned him over carefully onto his front, and lifted the pyjamas away from his bottom.
“Ooh,” she cooed sadly, “Poor you. Would you like some cream?” Tim felt his cock move. He nodded. Miss Cartwright came back to the bed with a big pot of white cream. She sat down and started to rub it in to Tim’s sore cheeks. He had to suppress a groan of delight as the cool, cool cream made contact with his sore flesh. And not just that but Miss Cartwright’s hands, they were rubbing his bum, stroking, smoothing, touching his skin. His cock hardened and pushed into the bed, and he prayed she would not notice.
“Tim,” she said softly, “come and lean over me,” indicating her lap. It was like the spanking position but it was so unlike the spanking his head whirled. Tim lowered himself over her neat lap, across the stretched blue cotton, and one hand hung beside him and brushed her stocking clad legs. Silky black stockings. His cock grew harder. The assistant matron took his pyjama bottoms right down to his ankles to begin her task and his cock stuck out into her lap as hard as it had ever been. Tim flushed purple as he knew she must feel it against her legs. But Miss Cartwright didn’t say a word. She massaged the cream into his sore skin as he lay there, peaceful at last, as the heat went away.
“Poor thing,” she whispered, as she rubbed, “does that feel better? I’m sorry for what happened,” she said, “Matron doesn’t really understand boys, does she?” He didn’t know what to say. “I do though,” she said as she made slow circular movements on his bottom with her palm, “I understand. It’s just natural, Tim,” she whispered, as his cock dug into her lap, “It’s perfectly natural,” and with those words, Tim, to his great surprise, felt her other hand slip slowly beneath his waist, under his body, and she took his cock gently in her hand. He let out a gasp. Her right hand continued swirling in a circle on his bottom. Her left hand grasped hold of his cock. A noise escaped his lips. “It’s natural, Tim,” she repeated, “Completely natural.” She started moving her left hand up and down his cock, along the shaft, down to his balls, and back up over the head, then down for a quick stroke of his balls and back up. Up to the head, then down, back up, down, up, down… all the time stroking his buttocks with her other hand. Tim gasped and his head spun as the beautiful Miss Cartwright masturbated him like one of his most erotic fantasies. Her hand moved faster, and focused on the head, tugging it firmly as Tim moaned and squirmed with pleasure. Miss Cartwright began teasing him in her honeyed voice, whispering the words into his ears and making his cock harder and harder,
“You were a very naughty boy, Tim,” she said, playfully, “a very naughty boy indeed,” he nodded yes, breathlessly “and naughty boys need teaching a lesson, don’t they Tim,” he panted out yes, yes, “naughty boys need their bottoms smacking don’t they…. bad boys need a good spanking, don’t they Tim?” As Tim gasped “Yes!” Miss Cartwright’s hand met his bottom in a light smack, a loving smack, and he moaned in delight, so she smacked him again, a little harder, at the same time pulling his beautifully hard cock. Loving playful spanks with one hand, long hard tugs on his cock with her other. Tim moaned in pleasure, the spanks making his bottom sting and his cock near to bursting. “Oh what a naughty boy you’ve been,” she sang, as he neared his orgasm, “what a very naughty boy, I want you to come here every day and take your spanking from me!” and with that lovely thought and a rather loud slap, Tim came over Miss Cartwright’s fingers. He sank in relief over her lap, smiling.
Miss Cartwright helped him into a sitting position.
“There, you needed something to cheer you up,” she said, smiling at him. He looked at her. She wasn’t old, perhaps not that much older than his oldest cousin Sheila who was 23.
He smiled, “Thank you,” he said, not sure what else he could say.
“There,” she laughed, and tousled his hair. “I think you can probably go back to class now, if you’re feeling better?”
He smiled at her, “I’m feeling much better, thank you.” She went over to a cupboard, and came back with a KitKat for him. Tim realised he was starving and ripped off the foil. She smiled at him.
“But you be careful with those stomach aches, Tim. Perhaps the stomach aches might only come back when I’m here, do you think?”
She winked at him and went out of the room to leave him to get changed. Tim grinned. He had a feeling he might be ill more often.