I suppose I have always been fascinated by the more mature woman, from the very earliest stages of my sexual awareness. My high school days were filled with a whole host of detailed fantasies surrounding several of my teachers, passionate dreams that although I knew would almost certainly never be realised, helped while away many an otherwise dull English, Maths or Geography lesson. In a similar fashion, I recall one particularly appealing bus conductress on my regular route, an extremely busty lady who worked in the local newsagent's, as well as a whole host of anonymous women, fleetingly glimpsed in the course of daily life only to be furtively recalled at a later time in the shape of discreet and colourful night-time imaginings.
My preference in no way hindered my sexual experimentation within the confines of my own age group, however, and throughout my latter teenaged years, I had a few one-time sexual partners. I heartily embarked - as, I suppose, do most young men - on a learning-curve that guided me through the various stages of experimental fumbling, premature ejaculation, tentative and awkward penetration and beyond, and had a thoroughly enjoyable time in the process; but still I retained, as much as ever before, my affinity with the more mature and experienced ladies of the world and my detailed fantasies thereof.
It was the day before my twenty-first birthday when I had my accident on the five-a-side pitch, breaking both my fibula and my tibia rather badly. The weeks of recuperation became months, my plaster cast was swapped for a pressure bandage, which in turn made way for endless physiotherapy sessions and slow and gentle exercise. It was during one of my daily walks, designed to rebuild and strengthen my musculature, that I encountered a lady I had not seen in a number of years.
Mrs. Jackson and I had lived on the same estate for, I suppose, as long as I could recall. She had always been a very friendly lady, imparting kind words and distributing treats to the local children, perhaps partly due to the fact that she had none of her own. I knew she had been widowed at a young age, though could not recall the circumstances, and to the best of my knowledge had never remarried - though I do remember overhearing a number of "neighbourly" comments regarding what I'm sure were her perfectly respectable "gentlemen friends." She had been one extremely attractive lady, and as I was passing her house that otherwise anonymous Tuesday afternoon, just as she happened to be making for her parked car, I immediately noticed this was still very much the case.
"Hello, Mrs. Jackson," I cheerfully greeted her, stopping by her garden gate as she approached me along the path. "How are you?"
I saw a flash of uncertainty cross her face, perhaps as she struggled to reconcile my vaguely familiar features with a name. I suppose the likelihood was that I had changed considerably more than she in the interceding ten years or so since we had last seen one another. I watched her trying to place me and silently admired her as I did so. Her shoulder-length, curly brown hair surrounded a facial beauty perhaps only slightly more enhanced by a careful application of make-up than had once been necessary. She had on a tight red sweater, beneath which her ample breasts strained provocatively and her above the knee, tight black skirt afforded me an excellent view of a pair of very shapely legs encased in black nylon. I realised Mrs. Jackson must easily be in her late fifties - possibly older- but in my humble opinion, she remained gorgeous.
"Stuart!" she exclaimed, recognition finally dawning, and smiled warmly at me. "My, how you've grown!" Then she frowned in concern. "Did I see you limping there?"
"Yes. Had a bit of an accident playing football," I admitted. "I'm on the mend, though. I'm out on my daily walk, building up my muscles again."
"Oh, I'm sorry to hear that!" she commiserated.
I shrugged. "One of those things. What about you? How are you getting on?"
Mrs. Jackson looked at her watch. "Stuart, I'm really sorry, but I'm already running terribly late for an appointment. Will you be out for a walk tomorrow about this time?"
"I'm out every day," I told her.
"Well, why don't you stop in for a coffee tomorrow and we can catch up. How would that be?"
"Great. Just about this time?"
"That'll be fine." She smiled, apologetically. "Now, I'm afraid you really will have to excuse me." With that, she hurried past me, the scent of her perfume trailing deliciously in her wake, and with a final little wave, got into her car and drove off.
For some unknown reason, Mrs. Jackson - stunning as she was - had never figured in any of my fantasies. It was an unexplained omission I certainly remedied that night. All through the hours of darkness and well into the dawn light, my thoughts were of this incredible lady and the host of erotic adventures I was sure we could enjoy together. As a result, I was tired and gritty-eyed the next morning when I finally coaxed myself out of bed and into a long, hot shower. I lathered myself again and again with the reputedly revitalising shower-gel, shaved, then splashed on some of the expensive cologne I had received the previous year as a Christmas present and reserved for special occasions. I took my time selecting what I should wear, carefully deciding upon what I believed were my very best clothes, but still found myself ready to leave the house by eleven o'clock. As it had been after two the previous afternoon when I had met Mrs. Jackson and we had agreed on a similar time for today's visit, I was left with some not inconsiderable time to kill.
I watched some anonymous daytime television; I tried to lose myself in what was the excellent novel I was half-way through reading; I devoured the sports' pages in the morning newspaper and much of what I found to be the intensely boring additional content; I even managed to prepare and consume a light lunch: but all the time I was watching the clock, counting down the minutes.. By the time two o'clock rolled around, I was so hyped up, I felt capable of sprinting the distance to Mrs. Jackson's house, some three streets away.
I managed to restrain myself from attempting this dangerous under the circumstances latter impulse, however, and set off at my slow, steady pace shortly thereafter, turning in at Mrs. Jackson's gate about ten minutes later. I couldn't believe how nervous I felt! After all, my night-time imaginings notwithstanding, the reality here was that this was likely to be a cup of coffee with an old acquaintance and a nice chat - nothing more. Telling myself to get a grip, I climbed the three front steps of what was a very well maintained semi-detached and rang the bell.
Mrs. Jackson answered the door almost immediately, dressed today in a pale blue dress - the hem of which also rode above the knee, I was pleased to note - black nylons and black, high-heeled shoes. She smiled warmly at me.
"Stuart: lovely to see you. Come in." She ushered me into the tiny hallway and through a door to my right which led in to her spacious living-room. "I'm so sorry about yesterday, but I was running dreadfully late and just couldn't stop to chat, I'm afraid."
"That's all right," I hastened to reassure her. "I understand."
"Good. Have a seat and make yourself comfortable." She waved me towards one of the black leather armchairs positioned either side of the fireplace, taking her own place opposite me. I very discreetly watched her dress ride ever so slightly up her thighs as she sat but she quickly positioned her feet discreetly together and her legs off to one side, as though deliberately minimising my pleasure. I fervently hoped she hadn't noticed me looking.
"So, Stuart, tell me about this accident." It was the start of a half-hour or so of small-talk, me describing my accident, my treatments and recovery process, her telling me some of what had been going on in her life over the past decade. I learned she had taken early retirement three years previously from her job as a laboratory technician, to spend more time in her beloved garden, travelling to favourite European cities and resorts and generally taking control of her own destiny and life of leisure. I was happy to listen to her, nodding, agreeing and making the odd short comment where it seemed appropriate to do so, all the time dreaming of how I would much rather we spent the afternoon.
"Well, I think I'll put the kettle on," Mrs. Jackson decided during a convenient lull in our conversation. "Coffee or tea?"
"Coffee for me, please - milk, one sugar."
"Coffee for two it is," she said, getting daintily to her feet. "I shan't be long." I watched her leave the room, unable to stop myself from staring at her naturally swinging hips, her shapely calves, my imagination going in to overload. It seemed strange to be having these thoughts about this lady I had known virtually all my life and who, I should perhaps mention, was considerably older than my mother. I couldn't help myself, however, and I was uncomfortably aware of my cock straining powerfully against the front of my trousers.
True to her word, she soon returned with the coffees and a large plate of assorted biscuits. I declined the offer of a biscuit and merely settled back in my chair with my coffee.
"So, Stuart, you haven't mentioned a girlfriend so far," Mrs. Jackson said, stirring her coffee. "I'm sure a handsome young man like you must be fighting them off!"
This was a twist I hadn't been expecting the conversation to take and my cup rattled slightly on its saucer. I sincerely hoped her choice of topic hadn't been inspired by her noticing the bulge in my trousers as she had handed me my coffee! But no, that was ridiculous - it was simply a natural question to ask any young man. I couldn't help but fleetingly wonder, however, if this could be the opening I required. Dare I somehow, very carefully, steer the subject towards my penchant for the more mature woman and see what, if anything, developed? I knew I would have to be extremely tactful and discreet, but decided to give it a go.
I started with what I thought was a nonchalant shrug. "There's no-one special at the moment. There have been a few short-term relationships, but nothing serious." I hoped I was sounding like a man of the world here and not some childish braggart, but Mrs. Jackson seemed fully attentive - genuinely interested, even - and I found myself thus encouraged. "I think I basically find women my own age still that little bit childish; immature, even. Most of them are still too obsessed with fantasies about pop stars to be interested in real men."
"Ahh..." Mrs. Jackson nodded, wisely. "So you're one of those young men who are attracted to the more mature, refined woman."
"Absolutely!" I tried to look pensive, scarcely able to believe my luck at where the conversation seemed to be headed. "I see age simply as a number, not a barrier. I think it's what two people are inside that matters. Judgements made by third parties about a younger man and an older woman, for example, are generally cynical comments made by those vain individuals jealous of their happiness."
Mrs. Jackson sat her cup and saucer on a small occasional table by the side of her chair and smiled. To my immense delight, she then casually crossed one leg over the other, affording me a tasty glimpse of middle thigh.
"I can see you've given it a lot of thought," she said. "You seem to have a very wise head on those young shoulders. And I agree with you absolutely." She shifted very slightly on her chair and, incredibly, her dress rode that little bit further up her legs. She gave no indication, however, of having noticed. "I suppose it must be a problem for you, though, actually meeting women of the age-group you desire who understand your feelings. Frustrating, I should imagine."
I couldn't believe how well this was going - it surpassed my wildest expectations! Was Mrs. Jackson actually flirting with me? I was acutely aware, however, of a small wet patch in my boxer-shorts where a dribble of precum had escaped my positively throbbing cock. I hoped it wasn't going to seep through and stain my trousers.
"Absolutely," I said, swallowing hard. "I guess it's all about trying to find the right words. How does a younger man approach such a lady without running the risk of making a fool of himself?"
Mrs. Jackson's smile widened. "I think, Stuart, that sometimes you simply have to 'bite the bullet' and express yourself the best you can. After all, what's the worst that can happen? She may turn you down, but she would have to be particularly cold-hearted to ridicule you in any way."
I was in little doubt that the opportunity I had so desired had just been presented to me on a plate. Did I have the confidence to reach out and grab it with both hands? I took a deep breath.
"Mrs. Jackson..." I faltered. The necessary words just wouldn't come.
"Yes, Stuart?" She was smiling in a different way now, almost mischievously. "What do you want to say?"
I took another deep breath. "I guess that what I'm trying to say is that I find you very attractive..."
As I again faltered, Mrs. Jackson continued to smile at me for what had to be the most interminably long ten seconds or so of my entire life. Then, as though making a decision, she got to her feet and came slowly towards me. She perched on the arm of my chair, making no effort now to stop her dress from riding up her thighs, and reached out a hand to gently stroke my brow.
"I knew that yesterday," she almost whispered. "I saw you checking out my breasts, my legs - all of me, in fact. Though let's face it, when you tell me that you find me 'very attractive,' what you are in fact saying is that you want to have sex with me. Am I right?"
I didn't know how to answer that one. I didn't want to blow any chance I had here by professing undying love or any of that nonsense; but at the same time, I didn't want her to think I saw her purely as a vent for my sexual frustrations.
She smiled. "It's all right, Stuart. I feel the same way." Her hand left my forehead and traced a gentle pattern down my cheek and chin, onto my chest, where she gently rubbed me through my shirt. With her other hand, she took my cup and saucer and sat them to one side, then she was kneeling before me, slowly unbuckling my belt. I was like the rabbit caught in the headlights, powerless to intervene or in any way prevent her from progressing matters as she so chose.
"The way your penis has been straining at its bonds this past while, I think we better take care of something in the shorter term, or we're going to have you making an unsightly mess in your trousers." She was speaking in such a matter-of-fact tone, almost as though we were still discussing my accident, yet she was now reaching inside my underwear and pulling my cock free. I couldn't believe she'd noticed my hard-on earlier and not let on; we could have saved ourselves a lot of time and meaningless small-talk. But now she had me in her hand and as she gently stroked my engorged manhood, she leaned forward to ever so delicately begin licking the precum from my swollen glans.
I was beyond speechless! This was my fantasy come true - the greatest experience of my life thus far. I had a woman probably not far off three times my age knelt before me, giving me a blow-job, and she certainly knew what she was doing. When she appeared to have cleaned me off to her satisfaction, she slipped her lips over me and began to slowly suck me deeper and deeper into her mouth. I watched as eventually my whole cock disappeared, then reappeared, knowing I could not hold off much longer. I think Mrs. Jackson sensed that too, because her attentions intensified, only the tip of me now inside her as her hand began masturbating me, as though to hurry me along.
I slid down in the chair as I came, thrusting my groin upwards, trying to force as much of my cock into her willing mouth as I could. I couldn't believe how much cum I seemed to be spraying into her, but she seemed more than game, continuing to work me until eventually - inevitably, I thought! - an overspill began dribbling out of her mouth and running down the length of my shaft. Swallowing hard, Mrs. Jackson chased the offending rivulets, scooping them up with her hungry tongue, finally leaving me completely drained. When it appeared she was satisfied with the job she had done, she gently put my cock back into my underwear, re-fastened my trousers and got to her feet.
"Come with me, Stuart." She was smiling, holding out her hand to me, and gingerly, I got up to take it. There wasn't another word spoken as she led me through a dining-room and up the open wooden staircase it contained to a small upper hallway. As we stepped through another doorway into her bedroom, she turned slowly towards me, and taking my face gently in both her hands, she kissed me, tenderly and deliciously on the lips.
No fantasy had prepared me for the sensations coursing through my body as I hesitantly wrapped my arms around this beautiful woman and savoured that first kiss. I couldn't begin to find words to describe what I felt in those initial moments when her soft lips touched mine. When she gently eased herself free of my embrace and took a small step backwards to reach behind herself and unzip her dress, letting it fall unhindered to the floor, I swear I felt myself already growing hard again. She was now stood before me in a black lace bra and panties and a pair of black hold-ups. As I continued to stare at her in wonder, she unclipped her bra and threw it onto a chair, then quickly slipped out of her panties.
"Well, Stuart, you wanted to see my body - what do you think of it?" She placed her hands on her hips and offered herself for inspection. My eyes travelled slowly downwards in silent wonder, over her full breasts - which did admittedly sag more than any I had previously seen in the flesh, but that surely had to be expected - onwards over her flat if ever so slightly wrinkled stomach, to her forestation of pubes and the incredibly protrusive outer lips of her pussy.
"Mrs. Jackson, you are amazing," I breathed.
She giggled. "I think we've gone beyond the 'Mrs. Jackson' stage, Stuart. Carol will do fine from now on."
"Carol..." It were as though something suddenly snapped within me and, emerging from my trance-like worship of her physical form, I began hurriedly discarding my own clothes. Then we were falling on to the bed, me naked on top of her, kissing her again, my hands roving over her warm, smooth, mature flesh.
It was immediately clear to me that this was to be as much an educational experience as a pleasurable one. Carol was not going to settle for my clumsy fumbling followed by a push and grind session. Already, she was guiding my exploring hands, first gently over her breasts, encouraging me to tease her hard and swollen nipples between my thumb and forefinger. As our deep, tongue-probing kiss continued, she then led one of my hands to her pussy, my natural inclination to simply poke and prod gently discouraged, her clitoris tenderly introduced to me before I got near her warm and wet inner folds. I grew in confidence, feeling more at ease all the time as she patiently instructed me with her own light but insistent touch.
I began to work my way down her body as my boldness increased, gently kissing her neck and throat, her upper chest, onto the swell of her breasts, where I lingered, taking each of her nipples in turn into my mouth - licking, sucking, nibbling. Carol was moaning softly now as both our hands continued their ministrations of her pussy, her face and neck flushing slightly as her arousal grew. I wanted to taste her down there, breathe in her heady scent, but at the same time I didn't want to interrupt or spoil in any way the process she had started.