A Conscientious CaretakerbyEllenDean©
A mature escort who enjoys fantasy role-plays with a "schoolgirl" theme reminisces about her first erotic encounter with an older man.
This is the story of my first sexual encounter with an older man. It happened when I was eighteen, and in my last year at school. The experience had a lasting effect on my life, and on my sex life in particular. To tell the story, I'll need to give you some background information.
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 Page 3 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.
The day I first performed "oral to completion" (as it's called nowadays) was a day that changed my life. That was with a lad my own age, and it happened some time before the events in this story. It was just an amazing experience, and one which I wanted to repeat, as soon and as often as possible. Since then, I've never looked back.
Of course, there were all kinds of other things that I wanted to try, but for whatever reason, I wasn't in a hurry. I didn't have a boyfriend, for the simple reason that I didn't want one. All that could wait. All being well, I'd be at university soon, and the opportunities would be there for me, in abundance, I felt sure.
Things moved more slowly in those days, after all. There was no such thing as the internet, there were no mobile phones as we know them today, and the CD had yet to supersede the vinyl record.
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.
I chose my partners carefully, to ensure discretion, as far as possible, and I'd also worked out the times when there was the least likelihood of being seen. Unless I was directly observed by a member of staff, I was ready to deny any allegations as malicious gossip.
So far, everything had worked out well, with just a single exception. The one person whose work took him to every corner of the school premises was Len the caretaker. I should have realised that it was only a matter of time before he saw me in action. In fact, he'd already seen me more than once, to my knowledge, and possibly more often. Strangely, though, no member of staff had ever approached me, to raise the subject.
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 story begins one afternoon, at the end of an ordinary school day. I was in a rather prickly mood, having just had a run-in with one of the teachers, about a piece of work I'd handed in recently, which hadn't met her expectations.
I was glad to be on my way home, and most of my fellow pupils had already left. As I passed Len's hut, he gave me a cheerful smile, and called out to me. He said that I would have to be "a bit more careful in future". He then said that if I got into trouble, it wouldn't be because of him, as he hadn't told anyone about what I'd been up to.
I was already in a bad mood, as my day hadn't gone well, and I immediately went onto the defensive. I assumed that he was talking about my escapades with various male classmates, behind the bike sheds. I knew he'd seen us there, at least once, but so far, as I've said, no teacher had ever asked me about it. I told him that if he were to tell anyone, it would be his word against mine, and that I didn't think I had much to worry about.
"No", he said, "that wasn't what I meant ... I'm talking about the pictures."
"What do you mean?"
"You know - those pictures of you, pinned up in the darkroom. The ones you did with the Camera Club. If those were to fall into the wrong hands, you'd have some explaining to do!"
I had to think fast. The darkroom was an old store-room in an out-of-the-way corner of the main building, that was used at various times by the sixth-form Camera Club. Len had access to all areas of the school, and so there was no reason why he shouldn't have gone inside, from time to time, if only as part of a routine check of the school premises.
A few days earlier, I'd agreed to pose for a few photographs, for a couple of the lads in the Camera Club. By today's standards the pictures were, to say the least, low-key. The set had a "retro" theme, with teasing 50s-style shots featuring high heels and stocking-tops. In some of the shots, I was proudly showing off my cleavage, but I'd kept my clothes on, throughout.
Even so, the agreement had been that this would be a strictly private shoot, and the pictures would remain the exclusive property of the individuals involved. Had the pictures got into the hands of a member of staff, my carefully constructed reputation as a conscientious and compliant pupil would have been lost for good.
There would probably have been more serious consequences for the boys concerned, as their activities would have been deemed a misuse of school premises and equipment, and a culpable failure to respect the privileges accorded to them as Camera Club members.
Our agreement had been spelled out very clearly, beforehand, and I'd been fairly sure that those concerned would have the sense to stick to it. That said, the thought of my pictures being traded surreptitiously among a select group of connoisseurs had a definite appeal, and I got quite excited whenever I thought about it.
I'd started to consider the possibility of posing for some more adventurous shots, and I'd have loved to do some. The lads would have had a great time, too, and so I'd been disappointed to find that their initial response was to run scared. They simply didn't have the nerve to take any more risks.
Right now, I was heaving a sigh of relief that I hadn't been offered the opportunity to take things further, after all. The stuff that Len had seen was incriminating enough, and it was solid evidence of a misdemeanour, and not simply the kind of rumour-mongering that I'd taunted him about.
This was a most uncomfortable situation, made all the more so by Len's evident reluctance to give a clear indication as to what he was going to do next. Making a determined effort to remain as composed as possible, I tried to ascertain the seriousness of the situation.
"What pictures are you talking about exactly?"
"You'd probably better come down to the darkroom to have a look for yourself."
"Is that a good idea? Going in there with you I mean. I don't want to get into even more trouble."
"Well it's up to you. You won't get into more trouble than you could already be in. And I'm sure you'd want to see what's there."
Len was right. I had to know what he was talking about. Somewhat reluctantly, I followed him along the dark narrow passage to the out-of-the-way bolt-hole. The room was on the ground floor, but the route through the dark alley-way gave the unsettling impression of leading underground.
I recall clearly the mix of feelings that fed my bewildered state of mind, as we made our way there, but I can't easily describe it. I was genuinely worried about where this was leading, I was desperately curious to know what was on show in the darkroom, and I was excited by the thought of my photos being on display, for the rest of the club members, and some of their mates.
I was even more excited at the thought of Len discovering the pictures, completely by accident, during a routine walk-about. And the anxiety, curiosity and excitement were heightened yet further, when I allowed myself to wonder what Len might have in mind, for when we were in the bolt-hole.
The darkroom was an eerie place. Even when lit, it was difficult to make out much of the detail of the interior. The Camera Club was open to boys and girls, but this felt like an environment in which only the male group members would feel comfortable. As we entered, we found various items of dark leather furniture, a sofa, a couple of armchairs and a couple of padded stools, in various states of dereliction.
Beyond those, I could make out what appeared to be the work area, with two large stone sinks, a draining board, and some shiny metal equipment, including something that looked like an oversized microscope. In the days before digital photography, if you wanted to process your own pictures - in black and white, of course - this is what the hobby required. It was like a laboratory scene from Fritz Lang's Metropolis, though not quite as elaborate, and on a somewhat smaller scale.
As I took all this in, I also saw what Len had seen, when he'd called in here, to do his routine security check. Taped to the walls were a number of striking large-format monochrome prints, featuring a young woman's legs in black nylons, with views of stocking-tops, seamed stockings, white knickers and shiny black stilettos. Some of them had been tastefully edited for presentation as pages of a calendar.
I was very relieved to see that none of the large photos showed any part of my face. Looking more closely, however, I realised that the shape of a shadowy mark that could just be made out on some of the shots was a clear representation of an ugly bruise on my right inner thigh, sustained during a particularly vicious hockey match, a day or two before the shoot, and still clearly visible on my skin, even now.
So, yes, Len was right: he had his evidence. Some of the club members would have some explaining to do, and so would I. So much for treating the material with "the utmost discretion", though! Maybe the calendar designers had been interrupted before they could complete their task. Even so, I found myself thinking that they'd deserve what they got, if there was any punishment to be dished out.
Len moved across to the tables at the darker end of the room, and picked up a handful of strips of film negatives. He handed them to me, saying, "You probably won't want these left lying around".
I would have expected him to want to keep them for himself, so that he could dangle them in front of me, to elicit some kind of reward for himself, for sparing me some serious trouble. Now, I had them in my hand. With the calendar pages taken down as well, it seemed reasonable to suppose that there would be nothing left that could be traced back to me.
What's more, apart from Len, no-one knew that any of this material was in my possession. Any group members would have assumed that a member of staff had confiscated it, and they would be anxiously awaiting the repercussions of that. Serve them right!
I fully realised that Len's unexpected act of generosity had solved a massive problem for me, at a stroke. At that point, however, it had simply added to my confusion. Feeling an overpowering sense of obligation, I blurted an anxiously awkward response.
"That's a massive favour you're doing me here, Len. You're going to say that I owe you a favour now, aren't you?"
Len's eyes twinkled brightly, and he smiled broadly. Another surprise, there: it wasn't the sly, lecherous grin that I'd been waiting to see, but instead, a warm, friendly appreciative smile. His expression had an oddly boyish quality, as if he'd done something to gain my approval, when he was half expecting a reprimand.
"We can't stay in here long, Ellen, or there'll be very big trouble for both of us. But you look so lovely in those pictures. If I could just touch you a bit ... would you have any objection to that?"
Before I could say anything, he'd moved in very close, still smiling his sweet, friendly, seductive smile, and then, stooping forward a little, he'd slid a hand under my skirt. This was something new for me, a wide expanse of unknown experience that had opened up with alarming suddenness. Fooling around impatiently with nervous, ham-fisted sixth-formers was one thing, this was quite another.
After all, this man was almost four times as old as me, and some years older than my grandad. He'd been married, and for all I knew he could have spent years with a fit, horny, sexually demanding wife. Whether that was the case or not, though, unlike my sixth-form guinea-pigs, close contact with a woman didn't seem to make him nervous, and he certainly knew what to do with those fingers.
The sensation of Len's leathery, work-toughened hide brushing against my baby-soft schoolgirl thighs was utterly exquisite. I smiled back, and all I could think of to say was, "Be careful just there, that's my bruise, it's very tender".
Len continued his gentle but purposeful exploration, running his fingers between my legs, and using both hands to lift my skirt and run slow, smooth, delicate strokes across my bottom. His eyes were closed, his smile broader than ever, and there was a distinct protrusion under the fabric of his trousers that hadn't been there a minute or two earlier.
This was my first contact with a man of mature years, who was comfortable with women, on the basis of - possibly - many years of experience. It was thrilling in the extreme. I knew full well that we couldn't possibly stay where we were for more than a few minutes longer, but I had to take this to another level.
With a swift, sudden movement, I grabbed at my knickers, and dragged them down. Stepping out of them, I dropped back onto the battered leather sofa, rolled back my skirt and spread my legs wide.
"Just for you, Len," I said, "a special treat. Do you like it?"
"That's enough, Ellen, you've gone too far already, I only wanted to touch you, that was it, that was all ... "
"It's all right Len, don't worry, I just wanted you to see me. You can't touch, you can't taste, just look. I'm a naughty girl, aren't I, showing off like this?"
"Yes, Ellen, you're a very naughty girl, but that's enough. We have to go now."
"No, Len, that's not fair! I've shown you my pussy, you've had a good look. Now you've got to show me your cock."
"Not now, that's far enough, get dressed, we have to go."
"No, come on Len, fair's fair, now it's my turn. You've got a massive hard-on, I can see it from here. Get it out and show me."
I couldn't believe that I was talking to this man in this way, a mature adult, a member of the school staff, and the one person who held my entire fate in his hands, at this point in time. But it got worse:
"Come on Len, you lovely, horny man, come on, you've got to come for me. Come for me. Then we'll get out of here."
I had no idea what I was doing. Like I said, I'd played around with lads my own age, I knew just how to get them turned on, and I could bring them off in no time at all. This was different. I knew Len was very aroused, but I had no sense of what it would need to bring him to climax, or how long it would take.
I was totally out of my depth. All I knew was that I wanted to see a real man's cock, fully erect, and I wanted to bring him to orgasm, there and then.
It only occurred to me later that Len had got out of his depth as well. Looking back, I felt pretty sure that, when he'd taken me into the darkroom, his main interest was in showing me the pictures he'd found, and seeing how I'd react.
Perhaps he might have hoped to get a view of my pristine white knickers, or to slip a hand between my thighs. I'll never know for sure, but I'd be surprised if he'd been expecting more than that. He'd seen me with the lads behind the bike sheds, to be sure, but my response to him, as a much older man, could still have been quite a shock.
Reaching forward, I grabbed his leather belt, and unbuckled it with a single movement. I took hold of his trouser zip, and a second later, his erection was in full view. This was my very first glimpse of what a mature man might be able to offer me, and I was spellbound.
Len's cock was magnificent. What impressed me most about it was its rock-hard solidity. Closing my fingers around it, it felt as straight and firm as the handle of my hockey stick. Strangely enough, that's very much what it felt like: weighty and rigid, yet with a soft, smooth texture to the surface, that felt reassuringly comfortable in the hand.
In the dimly-lit room, the skin of the shaft seemed to have a dark, leathery look, and the mushroom-like tip was a rich, deep bluish-purple, with a lustrous velvety sheen. His scrotal sac seemed inordinately large and heavy, his balls hanging like ripe plums in the pouch of dark, wrinkled skin.
As to size, I was far too inexperienced, in those days, to reach any kind of judgement. At the time, I made a wild guess that it was roughly the size of the six-inch rule that I carried in my satchel, and the shaft was not much more than an inch wide.
Looking back, from a position of wide and varied experience, I'd say I got that about right. As I said, though, for a man of Len's years, it was the strength and responsiveness of his erection that were remarkable, and I had good reason to be favourably impressed.
There were so many things I wanted to do with that gorgeous cock, but I fully realised that this was not the time. I caressed it gently, running my fingers lightly up and down the shaft, and rolling my thumb playfully across the head.
Then, most reluctantly, I withdrew my hand, and sat back in the sofa. Len took hold of that impressive piece of equipment, and began to stroke it, slowly and steadily, along its full length.
"Come on then Len, wank that gorgeous cock for me, let me watch while you wank yourself off, come on, wank it as hard as you can, show me how you do it, come on, I can't wait!"
Gradually he increased the speed of his rhythmical movements, using his thumb to create a steady friction across the tip. The swollen, bluish-purple head seemed to grow larger still, as he worked away. He closed his eyes, and seemed to drift into an elated, trance-like state as he hammered up and down with his tightly-clenched fist.
I stretched out my hand again, and with the tips of my fingernails, I traced delicate circular movements over the base of his scrotal sac. That was a technique that I'd already practised with my bike-shed buddies, with reliably positive results, and I was fascinated to see that it was having the desired effect for Len as well.