Housemaster’s Perks - Anne
Ships in Convoy     Jan 2020

A couple more meetings then off up North on Thursday. Samantha had headed off to see her husband and to show off the stripes across her bottom but presumably not report on the aftermath. There was a gentle knock on the door. “Come in,” I called out. Anne Cory peered around the door then came in. The headmaster's assistant secretary was an attractive girl or so it seemed. As the headmaster liked it, she was dressed very demurely. She wore a dark brown midi-length dress, with black boots hiding the rest of her legs. Her pale brown blouse had full length sleeves and was drawn up tight around her neck. Only the cheeky round face and long black hair, which almost went down to her waist, hinted at anything sensual inside.

“May I have the Bernard Darnley file back please?” she asked timidly.
 “Oh, sorry,” I apologised and handed her the file.
 “Thanks,” she said, then hesitated. I studied her demure outfit and the rest. After a few moments, she blurted out, “The Headmaster says you live up Cheshire way.”
 “True,” I said puzzled.
 “The rail strike doesn't seem to be ending. My parents live on the Wirral. He said you might be able to give me a lift.”
I smiled. “My pleasure.”
 “Oh, thank you. It would be a great help. I promised them I'd be home this weekend.” She suddenly looked much more relaxed.
 “There's only one snag. It's a long journey. I usually break the journey and stay over in a hotel for the night.” To my surprise, she gave me a knowing smile.
 “I’m sure you will make it an exciting evening.”
 “That sounds very broadminded.”
 “This is the swinging sixties, isn't it? Well, I seem to missing out on it.”
Rather taken aback, I said, “I'll do my best to rectify that.”
 “You may also have to rectify my behaviour,” She looked at me with a quizzical look.
 “From what,” I asked.
 “Oh, you know. Repressed country girl escapes her environment, sort of thing.”
 “I'll do my best. Why don't you let me organise some dinner tomorrow evening then we can make an early start on Friday? “
She gave me a broad relaxed smile and sighed,  “There's life in this college after all.”
 “What time should I pick you up? And what’s your address?”
 “Uh, uh. I don't live in the type of place a smart young lady likes to be picked up from. I'll grab a taxi back here.”
 “Uh, uh. You come to my house.
She looked surprised. “You don't live here? You must be paid a lot more than the pittance they pay me.”
 “I'll tell you tomorrow.” I gave her my address.
 “Okey, Dokey. You got a cane there?” I nodded. “Right, see you at six.” She tucked the Darnley file under her arm and sauntered out, a much happier girl than when she arrived. Moments later her head appeared around the door, “What car do you drive?”
 “Aston Martin DB5 Shooting brake.  Why?”
 “I guess that I can bring two suitcases then.” She smiled and closed the door behind her, not waiting for my answer.

What a contrast next day! She was wearing a slinky black micro-skirt that just covered her bottom, and what a great bottom it was. Her legs were covered by black stockings which led down to shiny black high heeled shoes. The only possible criticism was the rather small contours of her breasts, but the smiling round face and long black hair were exquisite.

The taxi driver huffed and puffed as he brought the cases in. I gave him a pound to cover the nineteen-shilling fare and told him to keep the extra shilling as a tip. Once he had gone and the door was shut, I looked at my watch and said, “What time do you call this?”
  She gave me broad smile. “Loads of packing to do and any way you need an excuse to thrash my bottom. “
  “Ok, if you want a hot bottom during dinner, I'm happy to oblige.” I frogmarched her upstairs to my bedroom and made her kneel on the linen chest at the end of the bed. Then I bent her over the foot cross bar, so her face was touching the bed cover. I pulled her arms out so she held the two ends of the cross bar. Her bottom was now her highest point. I raised her dress to reveal that she had no panties on. Instead her garter belt and two garter straps neatly framed her bottom. “Stay there.”

  I went to the cupboard and took out the cane, then I caressed her firm, full, round bottom with it. For the first time, I noticed her beautiful olive coloured skin, currently completely unblemished but not for long. I raised the cane and laid it on hard. She yelped, hissed and wriggled her bottom uncontrollably.  I took my time and watched the tram lines appear across the attractive bottom. I laid on the second stroke and saw her grip so tight on the cross bar her hands looked almost white. She yelped again and shook her head, the black hair flying in all directions.  Time and again the cane fell until the sixth stroke landed. The lines across her bottom looked impressive as she sobbed quietly on the bed cover.

  I pulled her up and she turned to face me, tears rolling down her face. Then she put are arms around my chest and hugged me tightly. In turn, I put my hands around her and let her sob onto my shoulder. A couple of minutes later she looked at me and said, through her tears, “God, you are good with that cane.” Then gave me a deep passionate kiss. My hands moved to her bottom and I ran my fingers over her stripes. She flinched but did not object. Just then, the chimes of the doorbell rang. She looked up at me, panic in her eyes, “Who’s that?”
  “Dinner arriving,” I said rather amused.
  “They deliver just for two people?”
  “During the week. At week ends they only do big parties. I’ll let them in.” I gently disentangled myself from her and sat her on the bed. “I ordered steak. I hope you like it.”
  “After that experience, I could eat a horse.” she replied with a broad smile.

I let the caterer in. She already knew my kitchen, so I left her to it. The steaks would take fifteen minutes, and she would lay the table. I told her to ring the front doorbell on her way out to say everything was ready. Back in the bedroom, Anne was now lying on the bed, feet apart playing with herself. “Aren’t you ready to poke me?” she said breathlessly, “because I’m ready for you.” She reached out to undo my fly buttons and pulled out my member. She was so desperate for it I plunged in, still wearing my shirt and trousers, and she in her sexy micro-skirt now around her waist. The doorbell rang in the middle of one of her orgasms, but it was ignored.

When we eventually arrived in the dining room, the steaks, in the warmer, were virtually dried out. The caterer had laid the two places at opposite ends of the dining table. While I moved the two places together, Anne served the meal, over cooked or not. As she started to eat, she announced, “Hell, I’m starving,” then proceeded to devour her meal. Finished, she looked at the Pavlova.
  “Want some Pavlova now,” I asked with a half-smile. “It looks delicious.”
  She breathed out heavily. “I think a short break would be welcome.” She turned to look at me with an intense look. “I never thought I’d get my first caning from you. I was trying to work out how to get the headmaster to cane me.”
  “What on earth for? Any way I think he’s scared of women.”
  She laughed.  “I think that’s right.” She thought for a moment. “No, every week several boys would be sent to the Head. Mrs Bennett would usher them into the Head’s office when he called her over the intercom. She came out and firmly shut the door. We would hear a couple of minutes of very indistinct conversation, then there would be the distinct thwack of the cane, six times in every case. Then the boys would come out flushed, a bit dishevelled, tears welling in their eyes. Hell, I so wished that it was me coming out; I don’t know why.” She paused for thought.
  “Then you come along and whip my bottom so hard that it is now deliciously warm. Its’s a great sensation sitting on a caned bottom. Hell, nothing else has ever turned me on like that.” She paused for thought again. “You know, I was excited from the moment you said you had a cane here. I could feel the damp between my legs and had to go lie down and play with myself as soon as I got home yesterday.
  “Then after the caning I was desperate to be poked. Nothing has ever turned me on like that. Mind you, not too sure that I enjoyed those three minutes, when you actually thrashed me, too much.
  Another pause for thought. “Not sure how I can avoid those minutes.” A further pause.
  “Hey, I’m ready for that Pav now.”

I stood up. She thought that I was going for the dessert, but instead I stood behind her. “Stand up.” As she did, I pulled her mini-dress over her head. Then I undid her bra. Naked from her panties upward, I made her sit again. I put my hands around her and pinched her nipples, which instantly grew in my hands. Then I whispered in her ear. “Perhaps another six strokes would help.”
  “Perhaps some of that delicious looking Pavlova first, then you have your wicked way with me.”

By eight-thirty we were back in the bedroom doing what is best done there. Suddenly during a lull in the adrenalin rush, she turned to me and asked, “Still want to beat me again?”
  “What red bloodied male wouldn’t want to thrash that fabulous bottom of yours?”
  “Let’s go to your office in college. We can pretend that I am one of your badly-behaved pupils. You can show me how you would deal with them.”
  “It’s getting a bit late.”
  “Rubbish, and we don’t have to get up early.”

So, forty minutes later, I was at the barrier to the service road, holding the intercom button, calling the porter at the front gate. “Richard Thurston here. I left some papers in my office,” I lied. “Just going to collect them.”
  “Ok, sir, no problem.” I put the key in the gate and the barrier lifted. I didn’t want a porter sniffing around to see who was in College.
  We entered the House by the back door and soon was in my study. I drew the curtains and turned to Anne. She now wore an extremely short bright red micro skirt and matching blouse. I sat at the desk and she stood the other side, hands tight together looking at the floor.
  “What’s the matter with you, girl. You know curfew is ten pm and you are certainly not allowed out in such a revealing outfit.”
  “Sorry, sir,” she muttered. “I won’t do it again,” she added, swinging her body gently around in a guilty pose. She played an excellent miscreant.
  “I know you won’t. Wait there.”  I stood up and pulled a large stool into the middle of the room, then went to the coat cupboard to fetch the cane. I tapped the stool, and said, “Kneel on there and put your elbows on the floor.” Doing as she was told, her bottom was high and a perfect target. I raised her mini skirt to reveal her superb bottom, this time not even framed by stocking paraphernalia. The stripes from the earlier beating were still clear but showing some bruising. I brushed my fingers between her legs, to discover a very wet recess.

I beat her very hard, but this time she was more prepared. Each stroke elicited a sharp intake of breath. Her bottom trembled violently in what seemed to be a cross between agony and an orgasm. The swishes and the thwacks seemed

very loud in the silent College. I tried to spread the strokes across her bottom with mixed success. By the end, she was sobbing loudly. But this was her idea. The beating complete, I mounted her in the same position that she had been caned, my feet each side of the stool. Her orgasm was fast and very violent. She shot forward onto the floor in front of her, her body thrashing around before she slowly calmed down. picked her up and she hugged me with all her strength yet again. Minutes later, I whispered in her ear, “Time we moved. The porter will be wondering how long it takes to collect a few papers.” She reluctantly agreed, tidied herself, and we headed back to the car. Unsurprisingly, we spent the rest of the evening in bed.

“Will you take a cane to beat me tomorrow night”
  “No, difficult to smuggle into a hotel. Might disturb the next room.”
  “Oh,” she looked visibly disappointed.
  “I’ll bring a heavy wooden ruler. Try some across the knee punishment.”
  “Sounds interesting.” Then suddenly she was asleep.

We woke about seven and had a couple of hours of sex. I dosed off again, when suddenly there was a loud yelp.  I woke startled and saw the naked girl standing by the window with half drawn curtains.
  “Is this all yours?” she asked incredulously. “A riverside pad?”
  “Yes and no.”
  “What does that mean?”
  “The house belongs to my family trust. We buy as much property as possible. No point in going for income nowadays with 90% income tax.” She went on looking out of the window while I admired her bottom, criss-crossed with lines and bruises. “Some people have all the luck.”

We loaded the car and headed North. “Where are we staying over?” she asked some way into the journey.
  “Warwick Arms Hotel in the town centre. About halfway, and very civilised.”
  “In Warwick?”   I nodded. The hotel had just celebrated its 250th year. I rather liked the old- fashioned feel to the place, a sense of strength and solidity. It was just after five when we booked in. I opened the sash window and the noise of the town invaded; I closed the window and it became rather airless.  Anne lay down, sprawled across the large double bed on the fancy embroidered bed cover. “You hungry yet?” I asked her.
  “Only for you.” She raised her hips and pushed her panties down to her ankles. “Did you bring the cane?
  “No, I think your bottom has suffered enough.” I made her sit up and stripped her naked. Then I made her roll over and put a pillow under her tummy, raising her bottom. It was time for some mind games; they seemed to be what she liked. I took off my tie and used it to tie her wrists together then tethered them to the bar of the bed’s headboard.
  “Hey, what are you doing?” she complained but did nothing to resist. Next, I fetched a silk scarf from my suitcase and blindfolded her. My right hand caressed her body and she started to writhe in response. Suddenly, I slapped her beleaguered bottom hard. “Ow, that hurt.”
  “Quiet. We are going to play a little game now.” I moved my mouth to a few inches from her ear, so she could hear me whisper. “I want you to imagine that you have been called into the Headmaster’s study. You have just spent a night in the police cell. You are still wearing your sexy miniskirt.  The Head is furious with you. He has offered you a choice; your cards or a beating. You have chosen the beating.” My hand continued to rub her bottom, which in turn now writhed my intently. My hand slipped between her legs, my thumb inside her stroking her G-spot, my fore finger rubbing her clitoris. “The Head has put two chairs back to back. You kneel on one and put your elbows on the other. He is standing there, cane in hand. You know he is wicked with a cane. But you feel terribly wet between your legs. He raises the cane and brings it down hard on your bottom.” I pulled my hand from between her legs and smacked her bottom hard. “Whack!” the agony floods through you. ““Count the strokes, Girl,” the head orders.” She says nothing but her bottom is clenching and unclenching rapidly. “I said Count the Strokes.”
  “One, Sir, Sorry, Sir,” she muttered into the sheets.
  “And I want you to hold back your orgasm until the sixth stroke then I want you to have massive one. Do you understand?” She nodded almost imperceptivity. “The Head raises the cane again.” I slapped her bottom hard. Her bottom trembled and clenched, almost as if a cane had landed, not just my hand. After a few moments, she muttered, “Two, Sir.”

And so it continued, my hand deputising for the cane. The result of the sixth smack was spectacular. Her whole body spasmed and her legs thrashed around. I put my hand back between her legs; all I had to do was keep it still. Her violent movements kept her G-spot and clitoris against my fingers and prolonged the orgasm significantly, my hand getting very wet in the process. “My God, what are you doing to me,” she blurted out breathlessly.
  “Just getting started,” I observed. “Don’t move.” I went into the bathroom, washed my hands and brought a bath towel back with me. I told her to roll over towards me, onto the towel. Facing upwards now, still blindfolded, I admired her body. Other than the smallish breasts, she was very well proportioned. “This time the strokes of the cane are only in your mind. I want you to count the strokes out loud, then have a massive orgasm on the sixth stroke. Do you understand me?” Again, a slight nod was all I had to go on.

I put my hands between her legs and pushed my thumb inside her. I could feel her cervix while the back of my thumb rubbed her clitoris. “Ok, girl, carry on.” There was a pause and I began to think the fantasy was not working. “Ouch………..One, Sir, please Sir, I won’t do it again.” Another elongated pause.  “Oh, shit, sorry Sir……. Two.” The next pause was even longer, when there was a sudden intake of breath, followed by a sob. “Three, Sir.” Then a shorter pause.  “Sir, please Sir, I cannot take any more……….Four.”  Then another long pause.  “Please Sir, I can’t take any more……..” A sob came out. “Five, Sir.”    Then quite quickly, Six” she yelled and her whole body shuddered. Her cervix dilated and I could feel it sucking, looking for sperm.

As the spasms left her body, I noticed that she was sweating all over. She sobbed, “Please release me. I cannot take any more.” Freed from her bonds, she clung to me hard, and we kissed passionately. “How do you do that?” she asked as she surfaced. She looked at me. “No, don’t tell me. I don’t think I want to know.”  Slowly her body returned to normality. “I’m starving,” she announced. She picked up the house phone and ordered a substantial meal from room service. The waiter wheeled the trolley in with a knowing smile. Anne had slipped under the covers, but, to put it mildly, was not very hidden.
 A couple of hours later, we were sated from food and sated from sex. “Want to start all over again.”
  “You must be joking. It’ll be a year before I am fit for sex again. That year turned out to be an hour before I entered her again, after which exhaustion overtook us both.

We had a hearty breakfast in the dining room, a stroll around the town, before returning to the hotel to book out.  The drive up the A34 was leisurely; Anne seemed in no hurry to get home. Lunch in Stafford was extended and a bit “boozy”.  Eventually we made Lancashire, and neared Anne’s hometown, just as it was beginning to go dark. “Let’s go up the hill and watch the sunset,” she suddenly asked enthusiastically.
  “Sure, if you want. Where do we go?”
  “Half a mile ahead, there is a turning to the left. It is not the best of roads.” That was something of an understatement. After a couple of miles of narrow, pot holed road, it suddenly opened out into a viewing platform with a couple of cars already parked there. “Keep straight on,” She said. “More private up there.”
   I pointed at the large sign saying “Private” just further up the road. “Should we be trespassing?”
  “We’re not. The owner is a friend of my Dad. He said we could go up anytime we wanted. Mum said they are away on holiday, so it will be nice and private.” I shot her a glance but said nothing.”

Another half mile of even worse road, mainly dirt track, brought us to another viewing platform, decidedly more make-shift. In fact, the only thing on the platform was a park-type bench, with wooden bars and cast-iron ends. “Let’s park here. Did you bring a cane?”
  “No, but I’ve got a sturdy wooden ruler. Should be just as effective.”
  She smiled. “I want a nice, hot, glowing bottom, when I get in. Sort of a constant reminder of you and the incredible things you did to me last night.” She got out of the car and wondered towards the edge. Her outfit was halfway between the demure attire that the Head approved of at college and the killer outfit of yesterday. But the blue skirt did little to hide the firm curves of her rear end. We sat down on the bench, Anne’s head on my shoulder, my arm around her shoulders. We watched the sun sink down, pink clouds stretching along the horizon and the skylines of Port Sunlight and Liverpool in the distance. But Anne was impatient.
  “Where’s the ruler.” I headed back to the car to collect it. When I turned back, Anne was bent over the back of the bench, arms stretched along it. Her bottom was offering a perfect target. I lifted her skirt to reveal powder blue knickers tightly outlining the shape of her bottom; the garter belt was gone. Given the thrashings her had received over the last two days, I left her knickers up.
  “Are you sure about this? Your bottom cannot go on taking for ever.”
  “Yes,” the muffed reply came. He solid wooden rule landed with a crack across her bottom. She yelped and her bottom trembled. She was having trouble staying in place. I laid on five further strokes in quick succession. I was glad no one could hear us. She yelped and sobbed but did not move. I pulled her up and she threw her arms around my waist yet again. I hugged her as the tears receded and the shaking subsided. We probably had gone too far, but she had found a new aspect of herself that she had yet to manage properly.

Back in the car, we held hands as the last vestiges of the sun disappeared. She moved towards me for a kiss, and my hand moved between her legs. Her inner recess was very wet, and the engorged clitoris sought my fingers. It was only a couple of minutes before her body exploded and exploded. Then suddenly, we both felt it was time to move on.

The road was a nightmare in the dark. It was twenty minutes before we were back on the main road. “Want to come over any see my place sometime?"
  She hesitated. “I’m not sure. My boyfriend wants to go to Greece for a few weeks. Do the Bohemian thing, island hopping. Not sure when I can.” I was stunned. She had never mentioned a boyfriend before. I suddenly felt used. I dropped her at the end of her road at her request, in case the boyfriend was at her house waiting to welcome her.

I never saw her again. It turned out that she had resigned her post with the Headmaster before she left. Despite giving her my phone number, she never tried to contact me. C’est la vie.