The Caretaker Gets Careless

Synopsis

A mature escort who enjoys fantasy role-plays with a "schoolgirl" theme reminisces about her second erotic encounter with an older man, which took place when she was 18. This is the sequel to "A conscientious caretaker".

Introduction

Thank you to all the readers who took the trouble to post comments or send feedback about my first story. I hope you find this one equally satisfying.

If you read my first story, you can skip the sections about me, my schooldays, and Len, as this material will be familiar. Please read the description of Len's hut, which is the setting for this story.

About me (for those who don't know me)

My name is Ellen. I'm a 45-year-old full-time escort based in Lancashire. One of my favourite fantasy scenarios is to play the role of a schoolgirl in uniform. Since I have been advertising this kind of session as an option, it has proved very popular with my clients, and it always works out well.

At the request of one of my clients, who found our classroom-based role-play especially gratifying, I wrote a story about myself as a schoolgirl. The events in the story took place when I was just 18. That story is called "A Conscientious Caretaker". In this story, I meet my school caretaker, Len, for a second time.

About my schooldays

I attended a local mixed school, with fairly high academic standards. I'd done well there, without having to make too much of an effort, and I'd shown a certain talent for sports as well. The school's uniform policy was strict, and for girls, a crisp white blouse and sharply-pleated charcoal skirt were mandatory, even in the sixth form.

I had no ambition to become a professional glamour model, but I knew I looked good, and I had plenty of self-confidence. I was physically fit, a little on the stocky side, with a curvy figure and lovely firm breasts.

By the time I'd entered my final year at school, I was already leading a double life. I was a popular and generally well-behaved pupil, and a strong asset to the hockey team. For some time, however, I'd nurtured a fantasy ambition, which was to become the school's most outrageously wanton filthy cock-sucking spunk-guzzling slut. At first, that was all in my imagination, but lately I'd taken a few discreet steps towards turning it into reality.

For the time being, I was happy to have my fun on a no-commitment basis with pretty much anyone who was willing and able. I'd identified a few of the older lads who were ready to appreciate some attention from an attractive young woman with a horny appetite.

I'd also found a suitably out-of-the-way location - behind a bike shed, believe it or not - and in a few short months I'd developed considerable proficiency in sucking cock. I loved the taste of spunk, I loved to swallow it, and even at that early age I was well on my way to becoming addicted to the stuff.

Len the caretaker

Len had been at the school forever. He was an active and conscientious worker, and rarely had any direct contact with pupils. He was a widower, now well past normal retirement age. To me, he looked at least a century old. He was fit-looking, lean and bony, with tanned, leathery skin that had the look of soft, supple animal hide.

He was known among the pupils as "lecherous Len". That seemed to me to be grossly unfair. It was quite obvious that he liked to look at the prettier girls, when he had the opportunity, but as far as I was concerned, that was normal, and in any case, I got a thrill out of being appreciated in that way.

It was widely rumoured that he often had a raging hard-on, even though it was difficult to be sure what was going on underneath the heavy fabric of his overalls. This was a frequent topic of discussion among the girls, but again, my attitude was that it was an entirely normal state of affairs, and if he was still hard and horny at his age, well, good for him!

The caretaker's hut (the location for this story)

Len's hut was a small, squat rectangular brick building with a flat concrete roof, tucked away, inconspicuously, at the back of the school. It was strictly off-limits to pupils. As well as providing storage space and workshop facilities, it was Len's place of refuge, where his privacy was guaranteed.

The school was built on the side of a low hill, and Len's hut was situated on rising ground behind the main building, at one end of it, with a clear view of the path that led down the side of the school, past the bike shed, providing one route to the main drive, and from there to the main gate. It was near that bike shed that I held my cock-sucking sessions, at certain carefully selected times. As far as possible, I tried to stay out of view of the hut, to minimise any risk of being seen from there.

Immediately behind the school was a large public park, separated from it by a high, thick, untidy hedge. Most people would have been aware that, by walking up the path to Len's hut, passing the door and turning the corner at the end, you would find, hidden just behind the hut, a narrow gap in the hedge that led straight into the park. Taking this route to enter or leave the school premises was not approved of, officially, but occasional use of it was unlikely to be taken very seriously.

The location of this concealed short-cut was important for me, though, and for this story. If I were to be seen going up the path, it would simply be assumed that I was making for the park. If I were seen entering the hut, however, then I'd need to have a very good explanation ready, as it was forbidden territory to pupils. Such as: I was returning a pair of gardening gloves that I'd found lying around somewhere. Or something along those lines. And if it ever became necessary for me to make a discreet exit, Len could act as lookout, and I'd be out of sight almost as soon as I was out of the door, as I'd be round the corner, through the hedge and gone.

Since my last story

... nothing had happened! My first encounter with Len took place quite unexpectedly, late on a Friday afternoon. The following Monday, I felt an urgent need to talk with him again, only to discover that he'd gone on holiday for a fortnight. Those two weeks passed more slowly than any I'd ever known.

I meet Len for the second time

At last the day arrived when Len was back on duty. He was already busy when I got to school. On arriving back, he would have seen any number of things that needed his attention, after his fortnight away, and he'd got started immediately.

That was a problem for me, as I couldn't approach him when anyone else was around, and we'd always have been in view from somewhere, at any time of day. I'd simply have to wait, and try my luck later on, at the end of the school day.

I'd never known a day to pass so slowly. There were so many things I wanted to say to Len, but with each hour that passed, I changed my mind about where to start, and when I packed up my books for the last time that afternoon, I was none the wiser.

I felt compelled to go straight to Len's hut, hoping that, by now, he'd be taking his usual tea-break. I slipped furtively into the short, narrow alleyway leading to his door. He opened the door before I could knock, and beckoned me straight inside.

He didn't seem very pleased to see me. I made a half-hearted stab at conversation, using one of my over-rehearsed opening lines, asking him about his holiday. He didn't seem to want to talk about that, though, and if I'm honest, neither did I.

"You know the consequences, don't you lass", he said, rather gruffly, "if anyone were to find out that you'd been here."

Of course I did. I fully understood the potential seriousness of the situation, and I could see why Len was concerned. During his time away, he'd had time to reflect on the worst-case scenario, if he and I were to be discovered together, and he had no wish to live through it.

I launched into a speech about why he had no need to worry, explaining all the care I'd taken to avoid being observed. I also took the opportunity to tell him how much I cared about him, and how far I'd go to make sure that nothing bad would ever happen to him, as a consequence of anything I'd done. The speech could have been better rehearsed, to be sure, but it was plainly spelled out and totally honest. It seemed to settle him.

"Sorry to sound so grumpy, Ellen, lass. I enjoyed the holiday, thanks, but the work has piled up, you know, while I've been away. It's lovely to see you, of course. We've got some talking to do, between us, haven't we? But there'll be time for that."

And then:

"Meanwhile ... I suppose I ought to tell you that you're interrupting something."

He smiled his familiar mischievous smile, but I didn't feel at all reassured. I had no idea what he meant. It was quite dark inside the hut, but I felt sure that we were the only two people there.

Len handed me a pair of field glasses, and I noticed straight away that they were stamped with some words in German, and a faded emblem, an impressively proud eagle, perched above a swastika. "War trophy" he said. "I'll tell you the story one day". That was an aspect of Len's life history that I'd never thought about before, but this wasn't the time to ask about it.

The field glasses were heavy, and felt solidly constructed. We'd studied the Second World War in our history lessons, but it had always seemed like something that happened a very long time ago. Now I had a piece of it in my hands.

Len indicated that I should go to the window on the far side of the room, and take my place on the padded stool next to it. The window had been blacked out, with the exception of a small rectangle, just wide enough to give a view of the outside. I'd seen the window many times, from the other side, and from a distance, and it had never occurred to me that anyone could see out of it.

The window overlooked the bike shed, and as I took up my position, somewhat hesitantly, on the stool, I began to understand what was going on. The viewpoint, the gap in the window-covering, the stool, the field glasses ... it all added up!

The location that I was about to focus on was the very one that I used for my cock-sucking escapades, though my own preference had always been to stay closer to the nearby boundary hedge, which would have meant that I wasn't quite in full view, seen from here.

Just lately, I hadn't been down to that area very often, so I was out of touch with whatever was going on there. If anyone else was using it, this might have been a good time to catch them, but I thought it most unlikely that Len would have seen anything of interest this afternoon.

I could not have been more wrong! As I found the right focusing adjustment for the field glasses, I almost fell backwards in sheer amazement. There was a session under way, the like of which I'd never seen before, and the power of the optics was such that I could have been standing right in the middle of it. I was staring into the face of a girl I hardly knew, and she seemed to be staring straight back at me, as if she could see straight into my eyes. I lowered the glasses, and blinked. It took me a moment to take in what I'd seen.

The girl was called Amy. I knew hardly anything about her, except that she was good at maths, and hung around with guys from the "science side", whom I didn't mix with. She was down there with two of those lads, one standing on either side of her. Nearer to us was a third lad, presumably on lookout duty. He didn't seem to be much use, though, as he just kept looking at Amy, and stroking an all-too-obvious protrusion in his trousers.

I had to take another close look. This was incredible. I considered myself the school's only true hardcore slut, but I'd never dared to take on two lads at the same time. And yet, here was Amy, with a hard cock in each hand, as blatant as anything, looking as though she was loving every minute. She was kneeling on the ground, on a folded towel, her blouse fully open, with nothing underneath. She had impressively large breasts with prominent, pale nipples.

The two lads were standing on either side of her, stroking her hair and caressing her breasts as she worked on each of them in turn. Her technique was surprisingly accomplished. She was pacing things slowly, and taking each cock very deep. And all the while, as I said, it was as if I was standing right in front of her, gazing into her eyes, as she gazed into mine.

I was fascinated, and yet, after a few seconds, I couldn't bear to watch any more. I handed the field glasses back to Len, who seemed only too happy to have them back. Something was bothering me about what Amy was doing there. It was just so incredibly blatant. It was as if she was putting on a show for Len's benefit - at his bidding, even - but how could that be?

"Len, I'm so sorry ... I can't watch any more of that. I'd like to go now."

"No, Ellen, stay on a bit. I just happened to see that lass down there, and I had to take a look. They'll be finished in a moment. Those young lads won't last long, the way she's carrying on."

He took back the field glasses, and sat up on the stool. "There, what did I tell you? There goes the first one - she's caught most of that - aye! - and there goes the other one. Oh, well done, lass, that was a couple of nice loads you took there, well done, well done!"

By now, I was feeling seriously uncomfortable. What on earth was I doing here, watching this hopelessly over-sexed old bloke - who by rights should have been pensioned off years ago - getting all fired up while observing a group of eighteen-year-olds engaged in frantic, surreptitious experiments with oral sex? Not only that, the experiments were being conducted by a fellow female exam finalist, one whom I'd never have expected to see doing anything of the kind.

Bizarrely, the girl was being outrageously blatant about what she was doing, as if she was getting off on the idea of being watched. And worst of all, from what I'd seen, and judging by Len's approving remarks, she was bloody good at sucking cock! Meanwhile, here was I, standing speechless in the gloomy darkness, being treated as if I wasn't there at all.

I was about to make my exit - properly this time - when Len slid off the stool and headed swiftly for the door. A moment later, I heard him speaking to the boy who was supposed to be on look-out duty.

"Is everything all right, lad?"

The boy's face would have been a picture, I'm sure. Len's approach would have shocked him out of his reverie, his role as long-range lookout having long been forgotten. Glancing through Len's peep-hole, I saw the boy scampering down the slope, waving franticly. I couldn't help feeling some embarrassment for Amy, as she struggled to do up her blouse as fast as she could. She gave her face a quick, rough wipe with the towel, which she then rolled up into a tight bundle. As I watched her run a hand through her hair, trying to regain some kind of composure, I saw myself, in just that situation, and I suddenly warmed to her.

I couldn't resist the urge to pick up the binoculars again, to examine the scene more closely. Amy seemed shaken. Strangely, she kept looking this way, and at one point she began to walk towards the hut, then appeared to change her mind.

The two lads who'd been with her sidled away rapidly, and were making their way as fast as they could towards the main gate. One had grabbed up Amy's sports bag, presumably expecting her to follow, but at a discreet distance. Meanwhile, the so-called look-out had disappeared completely, in some other direction. Amy smoothed down her blouse, straightened her skirt, and strolled slowly away.

Before I could get too lost in my thoughts, Len came back into the hut. He seemed pleased with himself. "I think I warned them just in time." Before I could make any further attempt to extricate myself from the situation, he altered his manner towards me, all of a sudden charmingly attentive.

That was a side of Len's character that I'd thought I was familiar with. I'd taken him at face value, as an honest chap who genuinely cared about me. Now, though, it dawned on me that perhaps I'd been deceived. I had to consider the possibility that I was dealing with a clever, devious and thoroughly manipulative character, with more complex motives than I could imagine. In any event, this man had a certain advantage over me, in terms of adult life experience: more than 50 years to my zero.

In a strange kind of way, though, for all my eighteen years of relatively sheltered existence, I didn't feel wrong-footed by him. In fact I started to find him even more attractive. I felt as though I could see through his tactics, and I wasn't about to be taken in. At the same time, I also realised that he didn't need to know that! If it suited me, on occasion, to let him think that I'd been fooled, then: so be it!

In the quarter-century or so since these events took place, I've come to the conclusion that there's a psychopath inside every one of us. I've also realised that, where psychopathic tendencies are concerned, I've got rather more than my share.

So I reckoned that I had a pretty good idea what was on Len's mind, and I felt reasonably sure that it had something to do with the impressive bulge in his trousers. For the moment, though, it suited me to play my part as the naïve and suggestible admirer, while he proceeded to treat me to a series of highly flattering compliments.

"Well, that was quite something, wasn't it? Two lads at once. And she swallowed the lot. That was a surprise, I must say. Quite a surprise."

Then, edging closer, he lowered his voice just a little.

"I have to say, though, Ellen, that she's not in your league. Given the choice, I'd much rather have been watching you. Aye, much rather."

"Len, for goodness' sake, what's going on? Watching with that thing, it's like you're just inches away from what's happening. And to think that you could see me that close, as well. It doesn't feel right at all ... "

"That's just it, though, Ellen, I've never seen you that way. You've always been much more discreet, tucking yourself away, behind the hedge, out of view. You've no idea how tantalising that's been at times."

I could very easily have tried to pick a fight with Len at that point. The whole set-up bothered me: the darkness in the hut, the narrow opening in the window-covering, the binoculars with their precision lenses, it all added up to something I didn't like.

Instead, I chose to let those thoughts follow their own course, and I allowed my attention to drift slowly back to the bulge in Len's groin. I decided to let him flatter me a little more, even if it meant that I had to fish for the compliments. And in any case, I was curious.

"Well, as you said, Len, Amy was pretty good. So why would you rather see me?"

"It's hard to explain, Ellen. Amy's technique is good, she knows what she's doing, and the lads love it. But she can take it or leave it. With you it's different. When you've got a cock in your hands it's as if you catch fire, you move to a different level, a different place, there's not many can do that. And for a man, that's a fantastic thing to see".

"Well, Len, here I am again! What's it to be? Same as before?"

As I spoke, I reached out to touch that bulge. It felt great to be able to sense the strength of his erection, under the coarse fabric of his overalls. It was his decision now: usher me out, or let me have my way.

For once, he seemed to have nothing to say. I carried on stroking, then reached for his zip. It was the heavy-duty type, and he had to assist me.

This was the second time I'd had the pleasure of seeing Len's truly gorgeous cock. As on the previous occasion, the generously proportioned piece of equipment was already fully primed. I closed my fingers around it, and paused for a moment, to let myself appreciate its size and solidity.