A Housemaster by Proxy


corner timeCary had heard about Tom from a friend. Only her friend had thought it was funny; openly mocking people who would visit this unusual man. But the details had been intriguing, more than intriguing even and secretly Cary had been excited by the whole idea.

“He doesn’t even charge money,” her friend had cackled, “You just have to fill out a form on his silly website and wait for an appointment.”

It had been excruciating to have to joining in the mockery while all the while being desperate to know the web address, but her patience had paid off.

The form had been a few tick boxes and a request for 100 words or less about herself and why she was interested.

Now she here she was on her day off from work having an adventure.

The building was down an alley in a courtyard off an Islington side street. It looked like an old Victorian school house and as far as discretion went it was perfect. There was no one about but the main doors were opened and they lead to a dark wood-panelled hallway with an old winding staircase.

At 28 Cary had never done anything like this, but had dreamed of it all her life. But such things never happened to her. She took a breath.

“Upstairs, knock and wait,” she repeated the mantra.

There was a hall mirror at the foot of the stairs and she sneaked a peek at the dumpy blonde meekly peeking back at her. She straightened up and steeled herself.

“You can do this,” she whispered.

Just then a creak on the stairs caught her attention and she looked up to see a tall man in a dark grey suit smiling pleasantly down at her. He was perhaps 40-something with pepper-salt hair and heavy eyebrows. In a way he reminded her of her old housemaster.

“You must be Cary,” he said casually, “You’re late.”

“I… missed the bus and then I couldn’t find the right street…” she babbled.

“Sorry Sir would have been sufficient,” he replied firmly.

“Oh… I thought…”

The smile left his face.

“Sorry Sir,” she said quickly.

“Come on then,” he sighed.

Cary gulped and mounted the stairs.

“I gather tardiness is an issue for you, as well as making excuses it seems,” he chided her even as he opened the door to his study.

“Yes Sir,” she swallowed, “I…”

She caught herself and decided not speak. Instead she looked over the book-lined room with the heavy dark oak desk and padded leather chairs. God, it was just like her housemaster’s study.

“You know why you are here?” he said in a business-like tone.

She did and she didn’t as such, she thought, but from what she did understand she knew it was better to play along.

“Yes Sir,” she said, the words coming easier now.

“Persistently late, always making excuses… you are a bit of a plodder aren’t you Cary?” he scolded her.

Game or not, it was true.

“Yes Sir,” she managed to reply.

“This is the first time you have been taken to task isn’t it?” Tom said thoughtfully.

Cary nodded until he glared at her again and she gasped out a “yes Sir.”

“Well, I will go easy on you this time,” he suggested almost grudgingly.

“Thank you Sir,” she replied with a blush, but strangely she felt disappointed.

“We will begin by giving you a good sound spanking and finish with six of the best with the cane,” he concluded matter-of-factly.

Cary took in a long slow breath through her open mouth and felt her heart race.

“Under the circumstances you will remove your own skirt and then come here across my knee,” Tom said as he sat down in the nearest armless chair.

Cary nodded. It was going fast but she was glad in case her nerve gave out. She asked tentatively if she could remove her jacket, waiting meekly for permission before she did so. Then with her back turned she stripped down to her blouse, knickers and charcoal hold-up stockings.

Despite the warmth he appreciated her efforts and nodded approvingly. On her form she had ticked almost every implement and augmentation as permissible within her requested scenarios, but she had also admitted that she had never been punished before. This time he would just use his hand as a prelude to the cane.

“Come here,” he reaffirmed.

She fluttered like a caged bird being taken in hand but then found some courage and stepped towards him.

He tipped her easily over his lap and was pleased to see that she naturally snuggled down.

Tom waited for a while before addressing himself to her underwear which he efficiently and slowly pulled down to her mid-thigh.

She gasped at the sudden breeze around her bottom.

“You were late, you are always late I gather,” he scolded her, “And do you always babble out weak excuses like that?”

“I know but…” she began wild with the idea that she was bare-bottomed over the lap of a man she hardly knew.

“What are you saying now?” he barked.

She swallowed and realised that she was doing it again.

“Sorry Sir.” And then remembering what her housemaster used to say added quickly, “No excuse Sir.”

“Better,” he growled, “It is a wonder that you were never spanked at school.”

“No Sir, I mean… yes Sir.” Cary was mortified now, it was just like she had imagined.

His hand landed with a crisp smack that robbed her of breath and set her eyes a goggle. The sting was worse than she had thought, but not too bad though, she assessed.

The second spank was no worse, but the way he followed it up with several more without pause made her squirm and rapidly struggle for an even breath.

“You naughty feckless girl, you really deserve this spanking don’t you?” he said sharply.

“Yes Sir,” she wailed.

“Gosh what a red bottom you have, does it sting?”

“Yes Sir, its burnie,” she said childishly.

“It is supposed to be,” he sighed showing no sign of slowing.

The spanking lasted beyond her ability to judge and although she didn’t cry she was bucking on his lap and struggling with the impact of his hand long before it was over.

“Alright, you can get up now and you may rub,” he said at last.

Cary leapt to her feet and clamping her hands to her bottom did a shameless dance, hopping from one foot to the other.

“No drama now, we haven’t finished,” he said sharply. “I want you to bend over the back of this chair for your six.”

As he spoke he pulled one of the over-stuffed armchairs away from the wall and patted the upper scroll curves of it.

It was a hard muddy green with quilted leather that was worn a little on the scroll back. And as she bent over Cary wondered how many other women had been bet across it. The leather was cool and firm under her and the pressure on her pelvis, contrasting as it did with the sting in her bottom gave her shameless thoughts.

Tom removed his jacket for the next part, swishing the cane menacingly through the air.

“This will hurt my girl,” he warned.

“Yes Sir,” she said thickly.

Wasting no time the cane cut the air and then her bottom with a bite.

“Ahh,” she yelled.

The pain was like nothing she had ever felt, she immediately bucked and then clawed at the leather. Her breath was ragged like she was drowning.

“Are you okay?” he asked in concern.

She dare not speak, but nodded vigorously.

The next stroke felt like a sword cut and went on sawing her for long moments.

“Ooh,” she held her breath and clamped her knuckles white on the seat.

“It gets worse,” he murmured.

But he waited for a bit before caning in again.

She couldn’t cope now and made parodies of chuckling in her throat as she twisted and moaned over the back of the chair. Her breathing was completely lost in effort and if she could look she would have seen three hard lines on red across her bottom.

The final three were each worse than the last and at the sixth stroke she collapsed into tears.

“Is that what you needed?” he asked.

She hated the suggestion of a break from character, but at the same time she appreciated it.

“Yes Sir,” she sniffed, reaffirming her submissive role.

“I have to see another girl and she will benefit from a witness, as will you I think. This is our first time together, so you can decide.” His voice was still beautifully stern.

“I’ll stay until you dismiss me Sir,” she agreed.

“Good,” he nodded, “I am done with you for today but go and face that wall. Keep you face pressed against it and don’t turn around.”

Before obeying Cary could not help twisting to look down her back at the prominence of her bottom and the top part of the cane ridges painted there. She could feel where they stood out and were harshly tender to the touch.

“Cary, go and face the wall,” he scolded her.

“Yes Sir,” she said eagerly and scurried to obey.

Her first time in the corner was an eternity and the other girl did not arrive for the longest time. When she did finally get there Cary blushed furiously, but dared not turn around. So she never knew who the girl was.

It was fun to listen while the woman (perhaps her own age Cary guessed) was put through much harsher paces than she had been. The spanking was longer and harder and the girl was sobbing long before it was over.

Then she had to take about 24 strokes of the cane, which she took rather better.

The unnamed woman was dismissed before Cary, but she was glad she had been included.

“Thank you Sir,” Cary blushed once she had got dressed.

“That’s my pleasure,” Tom said. “Do you think you will come again?”

Cary nodded enthusiastically.

“Do you want real help?” he asked.

“You mean like… mentoring?”

“Something like that,” he smiled.

“Yes Sir, she said brightly.

“Then I will be in touch.”


As Cary reached the bottom of the stairs a sophisticated woman in an expensive business suit was coming in. She had thick black hair and looked around 10 years older than Cary.

“Good morning,” she said as she went up the stairs.

“Morning,” Cary called after her.

The throbbing lines of pain still burned across Cary’s bottom under her skirt and it gave her a secret thrill that the rest of the world looked normal. She thought about the other girl and the woman on the stairs. How many more will be sitting gently that day?

She found herself smiling until people began to stare.

What would her friends say if they knew?


8 Responses to “A Housemaster by Proxy”

  1. 1 paul1510

    I’m not sure that I could do this, but it is certainly intriguing. 🙂

  2. 2 Laura

    Ummm (blush), I was wondering if (hoping) I might get that web address?

  3. 3 DJ

    Fantasy is often hard to fulfil 🙂

    Laura – no but I was thinking of setting one up 😉

  4. 4 Kia

    Definitely an intriguing scenario. Great twist at the end- having her serve as a witness.

  5. 5 cindy2

    I wonder if Cary heard the second girl speak while taking her discipline. If she did not, and since Cary’s head was facing the wall, could the second girl have been Cary’s friend, the one who appeared to have mocked Tom, but may in fact have been trying to entice Cary into conctacing Tom? And if the plan was for both girls to be present together with Tom, Cary’s friend would have made sure that Cary would not have been able to make out her voice.

  6. 6 DJ

    Cindy – I like the way your mind works 😉

    Thanks Kia 🙂

  7. 7 cindy2

    Thank you, Damian. cindy

  1. 1 chross.blogt.ch

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