The Tutor
Chapter 1

Caution: This Historical Sex Story contains strong sexual content, including Ma/Fa, Ma/ft, Teenagers, Cheating, First,

Desc: Historical Sex Story: Chapter 1 - Set in the early sixties, a tale of a young teacher and his 'adventures' in a mixed boarding school.

How many times have you seen similar headlines: ‘Teacher arrested for illicit affair with pupil’? It happens a lot these days, mostly because of social media. The pupil feels the need to boast and someone who shouldn’t know gets involved, either through the post or the fact the idiot took pictures. That I reckon is 95% of the reason, the other 5% is sheer bad luck and somebody stumbling on you in a compromising situation.

It was easier in the past; no one felt the need to tell the world and their dog. Providing you were bloody damned careful it was possible to enjoy the forbidden fruit of older teen pupils without the media mob or parents hauling you out with waving torches and pitchforks to tar and feather you (if you were lucky).

My name is Howard, it’s not my real name of course, none of the names in this account are real, there’s still a chance that one of my conquests might take it into her head to cause a stir. After all, look at the current witch-hunt in UK society over celebrity molesters.

Not that I’m a celebrity, no. I’m just an ordinary school-teacher, or school-master-cum-tutor as they were then known. I taught at St Winifred’s private Boarding School for girls and boys and the period I’m relating to you was the 1960s, a time of great social change.

I taught Mathematics up to sixth form levels and beyond. I say taught, I’m retired and about the most I can do now is move from a bed in a rest home to a chair in the lounge of the said rest home. Still, the body may be worn out, but the mind remains as sharp as a tack.

It wasn’t my first job, but the pay and perks were by far superior to the public sector teaching roles my colleagues mostly aimed for. I had free room and board, a comparable wage and the joy of working with some of the brightest and best of the academic system. Not that it was easy, the pupils were pushed hard and the staff were expected to produce results, though the grapevine amongst teachers said there were problems along that line.

The school, for all it was a mixed gender intake, was also strictly segregated. The pupils were only allowed to mix during properly organised and supervised social events, save only the mandatory dance classes that taught them the basics for the social events. Other than that, the two sexes did not mix and rarely saw one another, even the break time quads being on opposite sides of the linked wings. Everything that could be done, was done to prevent any sort of scandal. In this day and age it might look a little over the top, but, that’s the way it was in certain schools back then.

On Friday I arrived driving my pride and joy, a nearly new Triumph Herald convertible, and parked in a vacant slot, not too close to the linking wing where the school offices were, along with the assembly hall, gym and a joint cafeteria which, I later saw, was separated by a barrier, right through the middle, blocking the view across of either sex.

First impressions they say are important. If so, the impression I made on the receptionist must have been dire as her contempt for the young (25-year-old) man standing politely in front of her was almost palpable.

“And what may I do for you ... sir?” she eventually asked.

“I have an appointment with Mrs Goodfried, the headmistress, at 10 sharp,” I replied politely, handing over the letter of my appointment as Maths teacher and for a preliminary induction.

“I have nothing here,” she almost sneered, tapping an appointment book with a single digit.

“Then may I suggest you check with Mrs Goodfried?” I replied.

“It’s Miss Goodfried! And I’m not to disturb her unless it’s urgent,” she huffed.

I checked my letter and it definitely said Mrs, but decided not to push the matter.

“Then I’ll wait until she’s free,” I replied and moved to one of the vacant seats near reception, but in plain view of the office area.

I could tell the receptionist was not happy, but, short of calling the police, could not have me immediately removed from the premises. I merely sat for ten minutes until a woman of indeterminate middle age stuck her head out of one of the offices and looked me over.

“Are you Mr Howard?” she asked in precise tones.

“I am indeed,” I replied inclining my head, not wishing to get off onto the wrong foot by correcting her on my name.

“Well, come on in. You’re late,” she replied beckoning me into the office, the sign telling me that it was the office of Mrs Goodfried, Headmistress.

“I’m afraid your receptionist decided that as I wasn’t in the book I was persona non grata,” I apologised.

Mrs Goodfried frowned, looked in the direction of the receptionist and clearly decided that that issue was something for later.

“Well, Mr Howard. You come highly recommended by the appointments committee, though I’m afraid I missed that interview due to ill health. Hence I decided in lieu of that to see for myself what they had foisted upon me,” she started, looking very closely at me.

“I can assure you that my qualifications and references are all in order,” I replied.

“Yes, my issue is that you are rather young to be working here, not your somewhat admirable qualifications,” she stated.

“You’ll forgive me if I fail to see how this would affect my teaching methods and standards,” I replied, frowning slightly.

“The problem is the girls. I would by far prefer an older teacher to prevent them from being attracted by your youth and distracted from their studies,” she finally added with a frown of her own.

“I believe I can cope and would be willing to accept a provisional appointment subject to review say after the first term. At that point it should be obvious to scrutiny if I am succeeding,” I replied, my heart sinking slightly.

“I believe I can find that acceptable,” she said after a moment’s thought. “Finding a replacement at this late stage would be difficult anyway.”

At this point I realised I was going to have to come across as God’s gift to maths to get my appointment approved beyond the first term, but still felt grateful to at least have a roof over my head, rather than have to move back in with my parents and the inevitable questions and squabbles over my ex-fiancée.

Mrs Goodfried pressed a button on her desk and a second door to the office opened and a young(ish) woman stuck her head into the office.

“Jennifer, could you assist Mr Howard to move into the vacant rooms in the Lumley wing and provide him with the information necessary to find his way to his classrooms, offices and the staffroom?” the headmistress requested.

“Of course, Mrs Goodfried,” Jennifer replied in pleasant tones. “Please follow me, Mr Howard. Do you have a car?”

“Yes ... er,” I began.

“Please, you can call me Jennifer, everyone else on the staff does,” she replied with a smile.

“It’s Howard, Howard Smith, not Mr Howard,” I chuckled. “But I wasn’t going to correct Mrs Goodfried on that, not when she was looking for an excuse to dismiss me before I’d even started.”

“It’ll remain our secret. I’m afraid you’re Mr Howard whether you like it or not now,” she replied with a smile.

We reached the car and I picked up my two cases before locking it again.

“All right to remain parked there?” I asked.

“Oh yes, just don’t park in front of the main doors to the offices and you should be fine,” she replied as I followed her shapely rear, which was encased in an almost ankle-length skirt, into a secondary door and up a flight of stairs, cautiously noting that she wore a wedding band.

“This is the Lumley block. Only staff are allowed on these stairs, the girls use the central stairwell,” she informed me.

“Girls?” I queried.

“Yes, Lumley block is the girls’ wing,” she added. “I suspect that’s why old prune face wasn’t too happy with you.”

“Ye Gods, I’m never going to be retained at the end of term,” I sighed.

“I shouldn’t worry, just avoid a scandal and I suspect she’ll forget all about you within a few days,” Jennifer replied with a sunny grin.


“Yes, really. She ties herself up in knots in a stupid boundary dispute between the school governors and the farm next door which takes all her time. Neither side wants to go to court, but neither side will cede in the dispute, so there’s constant letter writing to each other, the local MP and the local paper,” Jennifer explained.

“Oh, right,” I nodded.

“This is your room. It’s got a nice view, but it’s a bit small. A cleaner will change the bed linen once a week and dust, but any mess you make over and beyond what she considers normal will be reported ... so don’t. You have a kettle, but if you bring food here, make sure it’s cleared away. Meals are served for breakfast, lunch and dinner in the canteen,” she explained.

“Right,” I acknowledged as I dropped my cases and she then led me to what she indicated would be one of my classrooms.

Fortunately it was only one level down and had an office attached where presumably I could store stationary and mark papers. The classroom was typical of its type, rows of desks with attached chairs and an inkwell on the desk; though Jennifer commented that the pupils used fountain pens now.

“This is the girls’ math room,” she explained. “The boys’ one is in the Raby wing in exactly the same position.”

“I take it I have to go to the ground floor and climb the opposite stairwell?” I asked.

“Yes, it’s the only connection,” she replied with a knowing smile. “If you need supplies, you can ring me on extension 02,” she added pointing to the phone in the corner of the room. “It’s 9 to get the operator, but don’t, the harpy on the front desk will report you, unless it’s a medical emergency.”

“Right,” I chuckled.

Jennifer took me over to the other wing and showed me the classroom and office there as well as handing me a schedule for the classes I would take, which, other than Friday, meant I was in one wing or the other. Fridays, she explained, were set aside for individual tuition. I had to make my own schedule for that, just make sure if it was with one of the girls I had another as chaperone.

After that we went back to the central section where she pointed out the way to the cafeteria and on to the staff common room on the ground floor where I was introduced to the rest of the staff.

The room was full and I was obviously the youngest. Jennifer, whom I put at ten years my senior, being the next youngest by quite a margin. I had a knack for faces and names which helped, but most were eminently forgettable and the entire room with one notable exception other than Jennifer felt like God’s waiting room. The exception was Rupert, whom Jennifer introduced as her husband and the English Literature teacher. He was a tall dapper man in his mid-forties, balding with a ludicrous comb-over and a thin pencil moustache; he was also, as a colloquial saying goes, ‘so camp you could set up tents on him’.

He greeted me with a ‘hello’ in a pronounced lisp and a very limp-wristed handshake, completely blanking his wife. He did invite me for tea in his cottage on the grounds, but I politely declined as I was fairly sure that Jennifer would not be in attendance. I may have been wrong of course, but I believed at the time, and later had it confirmed, that Jennifer was his ‘beard’ as a later description put it.

I decided then and there, that unless I had a very real need to be in the common room, I would avoid it like the plague, not because of Rupert, but because it simply sucked the life out of anyone who spent any time there.

After that, Jennifer bade me a cheery farewell and went back to her duties whilst I returned to my room to unpack before heading down to the cafeteria for lunch.

It was here that I found I’d been designated a table with other tutors and teachers on the girls’ side, presumably to ensure that the correct decorum was maintained. Not knowing the etiquette, I simply followed the lead of one of the other teachers, a Susan Hatchett who clearly didn’t like my presence anywhere near her, yet looked at a few of the older girls with longing eyes. I went to my seat at the head of my assigned table and stood there as a whistle blew and the girls (and boys presumably) were marched in, form room by form room, to the tables set aside for them, or rather some of them, I’d gathered from Jennifer that not all the pupils had arrived as yet, there were several day-stay as well as week-day-stay pupils. Term would begin on the Monday, so I had Saturday and Sunday to try and entertain myself in and prepare an initial lesson plan.

The girls, all aged about eleven or twelve, stood at their chairs at my table and were joined by an older girl wearing a prefect’s badge. Grace was said by Frank Parsons to the muted hubbub of a grace from the other side of the partition. Once done, there was a soft chime from near a serving hatch and all sat save the prefects who went off to the hatch to begin serving the food. Despite the clear regimentation, the food itself was reasonably good (for its time) and was served up quickly as the girls on my table all looked surreptitiously at me.

“You can call me Mr Howard,” I introduced myself. “And I don’t bite,” I finished with a chuckle as a low buzz of conversation began.

“Teresa,” the prefect introduced herself. “Um, what are you here to teach?”

“Oh sorry, should have said. I’m the maths tutor,” I replied.

“Oh...” came a buzz of conversation from the table as the girls then cautiously introduced themselves and I placed their names into memory.

“Are you sixth form, Teresa?” I asked, looking her over and seeing a pretty blonde blue-eyed young lady.

“Yes, rank has its responsibilities,” she replied with a slight smile.

“Like serving lunch,” I chuckled.

“Yes,” she said with a broader smile. “But only lunch, Trinny and Angela do breakfast and dinner respectively.”

“And the reward?” I asked.

“We get to stay up late and can play music in our form room,” she replied.

“A generous deal indeed,” I said with a smile.

“Can get boring. No boys to dance with,” she giggled, then blushed as she glanced at me as the other girls all twittered and giggled as well.

“Oh, I’m sure the practice will come in handy later,” I replied as we steadily ate the light lunch in front of us.

I had to admit it was a pleasant time; the girls were obviously shy, but nice to talk to. They soon extricated the fact that the Triumph Herald was mine and asked what it was like to ride in with the top down. I told them if the weather was fine that it was one of the nicest things you could do and I could tell a few at least wanted a go, particularly Teresa, if her body language was to be believed.

Afterwards it was plain that I was the topic of conversation amongst the sixth form girls at least, judging by the number of glances I was getting as well as the crowd around Teresa.

As it was Friday, I decided to nip into the nearest town to a Lloyds bank, a quick five-minute journey and arrange for the transfer of my current account from my existing branch in Gateshead to be available at the local one, something I was told would take a couple of weeks. Once done, I wandered through the small town centre, identifying a tea shop, pub and the local park. I then popped into a small department store to purchase a record player before calling at the music store next door to get some records of what I knew were popular artists. I then headed back to the school with my purchases to drop them off in my room. It was obvious I was being observed from the windows on both sides. I did have the top down on the Herald to enjoy the early September sunshine and suspected I was making quite an impression.

Still, I had work to do and a lesson plan to make so I headed down to my office in the girls’ wing to have a look at the books they were using. With a sigh I realised that they were still using the original Loney and Grenville’s ‘Arithmetic’ book and not anything that might assist them in algebra or calculus, which was almost sure to crop up in their exam papers, particularly at A-level standards. Indeed a lot of the coursework for the girls (as opposed to the boys) reflected an expectation that women would have to become familiar with arithmetical requirements associated with cooking, with earning a wage, with computing electricity and gas bills, with planning a budget and with the functions of the Post Office, not something the higher Universities wanted. Fortunately there was enough leeway to bring the girls and boys standards together and hopefully garner a fresh approach leading to much higher standards and pass rates.

As my tale mostly regards my activities with some of the girls, I’ll concentrate on them, however my methodology, which included a lot of what were then new-fangled ideas, but are now tried and trusted ways of teaching, produced some very astounding results which brought the school to the attention of a much broader (and richer) vein of parents.

Still it took several hours to put a plan into place and I was really ready for dinner once the warning bell went off.

It was exactly the same routine as lunch-time, exactly the same place and people, save for the prefect now being Angela, a shy ginger haired lass with a mass of freckles over her face, though as I found out later, a figure that would have been the envy of a Miss World. Not that the school uniform flattered any of the young ladies: an ankle-length baggy skirt, white blouse and thick cardigan, which was optional in the summer, hair was worn long, or in a ponytail, no braids and definitely no make-up. It did change after a few years to a knee-length skirt, but I believe it was the first change in over fifty years. The boys uniform didn’t change at all. The materials became lighter and the styles more modern, but a white shirt and dark trousers was simply a white shirt and dark trousers.

“So, what are you hoping to do once you’ve taken your exams?” I asked Angela, hoping to draw her out as I had now achieved with the eleven-year-olds who were quite happy chattering away.

“I’d like to become a doctor, but I’m not sure if my grades will be high enough,” she replied quietly, eyes downcast.

“Which grades need to be higher?” I asked as I had a couple of other arrows in my quiver that I could teach at a certain level.

“Biology and any one other,” she almost whispered.

“I’m setting up a study group to assist those who need help. I can certainly assist you in biology and maths, if you’re willing to work hard,” I replied with a tentative offer.

“You could?”

“I can, yes, but you’d need a study partner,” I added.

“Trinny and Teresa would do it I’m sure,” she replied, her whole countenance brightening. “They both need maths and one of the sciences to make their grades good enough for a university place.”

“Well, I’ll be willing to help if that’s what you want. Think of it as payment for your charming company during dinner,” I jokingly chuckled.

Dinner ended shortly after that and the girls were marched off to their dorms and study rooms and I noticed Angela and Teresa in conversation with a dark haired young lady I presumed to be Trinny as they left to be locked up for the night.

Unlike the students, staff weren’t confined to quarters, so I decided to pop into town and have a drink at the local and see if I could get more info on the area. I rather doubted I’d find a woman, but you never know what life might bring.

I parked at the pub and was pulling over the cover for the convertible when a Morris Minor pulled in behind me and Jennifer stepped out.

“I thought it was you,” she greeted me.

“And you were right,” I chuckled.

“Just dropped Rupert off. He’s visiting his friends in London, won’t be back until tomorrow,” she explained.

“Not go with him?” I asked, though I suspected I knew the answer.

“We ... er, don’t see eye to eye ... on his friends, that is,” she prevaricated, slightly in my eyes.

“Well, would you care to join me in a drink?” I asked.

“Oh ... I never ... oh, thank you, yes,” she replied with a lovely smile.

“This won’t hurt your reputation, will it?” I asked.

“It would if anyone knew me,” she replied with a slight giggle. “Any staff here ... would probably understand.”

We went into the snug, not the bar where a woman’s presence was frowned upon, and I got her a port and lemon and myself a pint.

“Anything I really ought to be aware of at the school on a personal level?” I asked.

“Well, despite running on an annuity its going slowly broke unless we can increase the intake somehow to make up the funding deficit,” she confessed.

“Yes, I can see why, judging from the text books for maths for the girls,” I nodded. “The rest of the staff are just marking their days until retirement and don’t care about the future.”

“Yes, that pretty much sums it up,” she sighed and sipped her drink.

“Well, I’m forming a study group and believe I can turn things around ... on the girls’ side at least. That’s where a lot of the problems lie,” I explained.

“Well, if you can get our exam pass rate higher than 30% with the girls, I can use that when I send out the mailing shot to interested parents,” Jennifer replied, looking interested. “Other schools have a much higher pass rate.”

“I believe I can help there. Though I might need to ensure I’m not interfered with in the methodology,” I replied cautiously.

“To be honest I rather doubt the rest of the tutors will bother, they certainly haven’t in the past. Plus I’m sure I can keep you under the radar with those in charge,” she giggled and I became aware she was tentatively flirting with me.

“Yes, the last thing you want is for someone to interfere when you try something new. They often don’t approve,” I replied carefully, permitting her to further the flirtation should she choose.

“Story of my life,” she sighed; though I had the feeling it wasn’t me she was talking to.

“Oh, I’m sure you can manage to get your own way if you choose to,” I chuckled.

“Yes ... I’m sure I could,” she said pensively with a sideways glance at me.

“Or keep it under the radar of those who really don’t need to know,” I replied looking directly at her.

“That would depend. I may need a co-conspirator to assist,” she stated, looking at me and running her tongue slowly over her upper lip.

“I’d be prepared to assist in any way possible,” I replied.

“Would you now?” she answered with a sly smile. “Oh, look at the time. I need to get home. Would you care to accompany me for a bedtime drink?” she finished with an offer I wasn’t going to refuse.

“I’d be delighted,” I replied with a smile of my own.

It was a short drive just past the entrance to the school and into a driveway that led up to what I can only describe as a cosy country cottage, classic roses around the door, spic and span and utterly secluded type, usually only seen in movies. There was a single light burning above the door which enabled Jennifer to unlock the door and let us in to a beautifully decorated living room.

“Lovely,” I murmured.

“Yes, Rupert’s work,” she replied in wry tones.

Other than that she looked slightly at a loss and so I stepped up to hold her in my arms and kiss her softly.

“Is this what you want, Jennifer?” I asked when our lips parted.

“Oh yes, only I’ve never done this with anyone else,” she whispered in my ear as my lips descended to kiss her neck and shoulders.

“Then let me lead the way,” I answered as I kissed her again and allowed my hands to wander over her body.

Jennifer’s own arms were soon wrapped around me as she held me tight, our lips locked together, our tongues gently boxing with each other.

“Follow me,” she finally said with a gasp and led me by the hand to what I was later told was her room.

We fell arm in arm on the bed, she giggling a little as my hands now slipped under her clothing to caress warm soft skin, pausing briefly to kiss any exposed to me. It was becoming obvious there was a lot of pent up passion and frustration in Jennifer as I now started to disrobe her, one article at a time. First her blouse, then her skirt, all the time kissing and murmuring compliments and words of desire. I took time to feast upon her small perfectly formed breasts, raising the nub of each nipple to a solid mass that made her moan in desire at my ministrations. The biggest surprise was sliding her panties off over her stocking clad legs to find she was fully shaven. I was kind of dumbstruck as I’d neither seen, nor heard of the like.

“Rupert insists,” she said into the silence. “It’s the only thing that attracts him at times, plus me on my knees and looking like a boy with my hair covered,” she finished in an almost sob as I suspected there was a little more to his depredations than she was admitting.

“Unusual but lovely,” I replied and kissed her down there, sliding my tongue into the wet softness and making her twitch and quiver at the swirling of my tongue over her centre of pleasure.

“Oh, oh, Howard!” she moaned in evident delight as I brought her pleasure to a crescendo.

Her back arched and her hands gripped my hair to force my lips and tongue down on her pussy whilst she gave out a heartfelt moan of pleasure.

“Good?” I asked when the trembling and moans stopped and the grip on my hair lessened.

“Oh yes!” she sighed as I moved up her body to kiss her and place myself at the entrance to delight.

“Ready?” I asked, seeing an eager nod.

I slid into her, feeling her gasp in delight as her stocking clad legs swung over mine to claim me.

“Please don’t spend in me. I couldn’t explain a baby,” she moaned as I began long languorous strokes into her.

“I’m sterile,” I admitted with a slight blush. “Glandular fever when I became a man. Caused my fiancée to break off our relationship when I had to admit the test results as she wanted babies.”

“Then do as you will, my lovely Howard,” she gasped and locked lips with me.

I picked up the pace as I pounded her hard and long, causing her to squeal deafeningly at times when an orgasm overwhelmed her. Finally, my own release came in a devastatingly powerful orgasm as I blasted my essence deep within her, pushing myself as deep as I could go.

We fell apart, our chests heaving and our bodies covered in sweat from our pleasure.

“Oh my, that was so good!” she gasped out between deep breaths.

“That it was,” I replied and kissed her, noticing a small smear of blood leaking from her pussy. “I didn’t hurt you did I?”

“No, Howard. You just were the first man ever in there,” she sighed as tears began to flow.

“But how did you? ... oh,” I tailed off as I finally realised the depths of Rupert’s abuse.

“Please don’t tell anyone,” she begged.

“I won’t, but I would enjoy doing this again,” I replied.

“You would?”

“Only if you want me too,” I replied and kissed her again.

“Oh yes, please!”

“A pleasure, truly a pleasure,” I replied as we kissed again for a while.


“Yes Jennifer?”

“Um, who taught you to ... um, you know, kiss me down there?”

“Promise not to tell?” I asked with a wry smile.

“Of course not,” she giggled.

“One of my Aunts,” I replied.

“No!” she exclaimed with a wide smile.

“Yes, you’ve discovered my dirty little secret,” I chuckled, seeing she wasn’t horrified.

“Well, good for her and damned good for me,” she replied and flowed into my arms as my erection was now almost fully restored.

“She taught me a lot,” I admitted.

“Then teach me!” Jennifer demanded as I pulled her on top of me and positioned myself to allow her to lower herself onto my throbbing erection.

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Story tagged with:
Ma/Fa / Ma/ft / Teenagers / Cheating / First /