The following events are based on fact and relate to an old crush I had on a school teacher that was to have an unlikely but surprising outcome years later. I was sixteen at the time of the crush and in my mid-fifties for the events I am about to relate.
Miss Croft was the music teacher at my old comprehensive school in the grimy northern city where I was born and raised. I enjoyed her lessons and often made her the subject of my masturbatory fantasies. She wasn't what you would call 'hot'. Indeed, not as hot as Miss White, our PE teacher. Now she was scorching hot, and every lad in the school fantasised about how it must be to stick their teenage cocks deep into her no-doubt juicy fanny. But she was pure wank fantasy, totally unobtainable, whereas Miss Croft was more in our league, and I knew for a fact that I was not the only kid in the school who lusted after her body.
Miss Croft was probably in her mid-twenties, slightly dumpy, not really fat, just pleasantly plump, and even at that time, with an 'everybody's favourite MILF' look about her (but, of course, back then, the acronym 'MILF' hadn't been coined yet). But really, what did it for me every time was her posh, southern accent. Most of the teachers at the school were locals, or at least from the generic 'north." Miss Croft was from Tunbridge Wells or someplace just as unimaginably suburban, and she spoke refined English as the Queen spoke in her Christmas Day broadcasts. I think that is called received English.
In the frequent wank fantasies of my burgeoning, overactive libido, I often dreamt of her speaking dirty to me and my trash-talking to her in return as I fucked her mouth, filling it full of teenage boy juice, followed by similar copious deposits in her fat ass and cunt. as she implored me to give it to her harder, faster, and deeper in that distinctive upper-class-voice. I must have gone through several boxes of Kleenex masturbating over Miss Croft.
Little was I to know how I would achieve my fantasy forty years later! In spades!
I had not remained in my hometown. After a spell in the military, I gained my HGV license and became a driver for a well-known freight company. I travelled all over the country and occasionally to the continent, too. I had married, had two teenage kids, and lived an everyday, suburban life in a semi on a small estate in a town no more than a hundred miles from my childhood home.
I still kept in touch with some of my old school pals and heard of the upcoming school reunion through one of them. This was something that I had to attend if only to check out how the intervening time had been kind (or not) to my old schoolmates and teachers. I asked my friend to put my name down for it.
The reunion was to take place in the early evening and was held in the assembly hall of my old school with the understanding that the party would continue, for those who were interested, at the local pub down the road.
As is usually the case with such reunions, the event started slowly with much-forced jollity and bad jokes, but things gradually relaxed as we drank the cheap plonk that had been thoughtfully provided. Many of our former teachers were present, all now in their sixties, seventies and older.
Time, she had not been universally kind. Miss White was there, and she had, from her look, had a hard life in the forty years since I last clapped eyes on her. She was at least double her weight in her pomp and age; childbirth and gravity had taken their inevitable toll on her formerly magnificent figure. She looked a mess.
Miss Croft, however, still did it for me. She had aged gracefully and looked in good shape for a woman in her mid-sixties. She appeared comfortable in her skin and looked like everyone's favourite granny, and despite being over ten years my senior, I still fancied her like mad.
She was still single (despite sporting a large gold wedding ring, perhaps to deter unwanted suitors) and had been retired for almost ten years, living locally. She was the chairperson of the local Women's Institute and was active in many other charitable events. She had a small apartment in town, and to supplement her pension, she taught music to kids.
How did I know this? Because I stalked her that evening, mooching around her like a faithful old dog. However, she didn't seem to mind, and I was amused to find that I had a semi-hard-on throughout, just as my sixteen-year-old self would have done. I am sure she must have noted this, particularly when we were jolted in the crowded pub to which we had moved later in the evening.
We had all had a little too much to drink by this stage, and after a while, we found a seat, and I plopped myself down next to Miss Croft.
As the alcohol and general bonhomie took effect and the group became more animated, I leaned over and whispered in Miss Croft's ear.
'Did you know, Miss Croft, that I had a schoolboy crush on you?'
She chuckled in that sexy, posh voice of hers. 'Yes, I did. I think you were the boy who was forever dropping his pencil so that he could check out my legs and hoping that I'd have them open.'
I blushed crimson, which I had not done in years. 'I didn't think you had noticed. Did you also know that I must have masturbated, with you as my imaginary wank partner, a hundred times?'
'Oh, you dear boy.' she chuckled again. 'How I wish that I had known. I would have opened my legs when you dropped your pencil and maybe would not have worn my knickers that day.'
Then she did something that astonished me and, as we say, where I come from, left me gobsmacked. She reached under the table where it couldn't be seen by others and grabbed my penis through my trousers, and squeezed it, none too gently.
I quickly recovered my poise and leaned over and whispered in her ear, 'I would like to fuck you, Miss Croft. It would be a fantasy come true for me.'
She laughed and said, 'I'm not that young anymore. Why would you want an old biddy like me? I'm fat, and everything is droopy.'
I said that I didn't care and still wanted her.
At this point, she deflated me by saying that she had to leave. As I mentioned, she was chairlady of her local branch of the Women's Institute and had a meeting or something to attend that evening. I was devastated, but then all my hopes came gushing back when she promised to get in touch to arrange a one-on-one meeting.
She whispered to me that she had not been fucked for over five years since a long-time partner had passed away (which might account for the wedding band) but still had sexual urges, which she satisfied occasionally using a vibrator. Naughty Miss Croft. She must be gagging for it!
The next few days were spent in a daze as I awaited her call or text. I masturbated daily, something that I hadn't done since I was a teenager. I was so horny, and in my fevered mind, I was forming a fantasy of what I would do with her if and when she got in touch and met.
It was torture waiting for her to get in touch, but after what seemed to be an eternity, I received a text from her asking if I was free to visit her in her apartment the following Friday. Just try and stop me, I thought. I was due to work that day but only had a short run, so I could text her back to say that I could come round to see her at 2 pm and was free until 5 pm. She immediately texted me back, saying that would be great and that she was looking forward to our meeting. As if it was a job interview or something instead of my fucking a teacher that I had fantasised about having so many years before. A dream comes to fruition.
The next few days passed so slowly that every second seemed to drag out for a minute and every minute an hour, but finally, Friday afternoon arrived, and I found myself outside her apartment block. She buzzed me up, and I entered her modern spick and span one-bedroom apartment. We had tea, made small talk as if I were one of her music students, and chatted more about old times. I was beginning to think that maybe I had misread the signs and perhaps this was just to be a platonic meeting, but then I recalled her hand on my hard cock and thought perhaps she was a little nervous and waiting for me to make the first move, so I did.
I reached out and slid my trembling hand up her skirt and rubbed her pussy through the fabric of her knickers. She immediately opened her legs and pulled her gusset to one side, allowing me full access to her cunt lips. I stroked her wrinkly but tidy pussy and then tried to insert a finger up her. I had forgotten that she was a spinster with no kids who hadn't been fucked for several years, so she was bound to be a little dry and tight. I asked if she had lubricant, which immediately appeared along with her little vibrator. I took this as leave to get properly stuck in.
I switched on the vibrator and pleasured her with it for several minutes while still having two fingers inserted deep into her clunge. She slipped off her top and pulled down her bra, exposing a small but useable set of tits. Of course, everything was well past its best-before date, but she was in generally good order for an old bird. I wondered briefly what her fellow members of the WI would think if they could see what I was doing with their chairwomen and what I intended to do with her. They would be utterly scandalised, and she would have been drummed out of that estimable organisation.
I had decided that I would have enough backed-up jizz to come three times at best and so decided it would be mouth, ass, and cunt in that order, just as in those wank fantasies of long ago. Of course, things didn't quite pan out this way (they never do… best-laid plans, etc.), but I wasn't too far off schedule.
First, I got her laid out on the bed. I knew that I wouldn't last too long on the first go, so I politely asked her if I might come on her face,
'Please, Miss Croft. Can I come on your face?' I inquired in a little boy's voice.
'Please do', she replied. I'd always dreamed of saying and doing this, so the reality sent goosebumps up my spine. I came quickly, a bit in her mouth but mostly on her face, which she rubbed in using my cock as we joked about sperm being an excellent moisturiser and good for the skin. She also bolstered my ego a little with some flattery and cock worship which also served to yet further inflame my passion for the fucking to come.
I was also a little shocked and amused to hear that this elderly, well-spoken retired music teacher had a bit of a potty mouth on her! You might think that listening to 'The Archers' on the radio would constitute her daily measure of excitement, and you would be wrong. To hear her describing my dropping a fair dollop of cum in her mouth and over her face as 'bloody great, fucking great' as she diligently cleaned my still throbbing cock with her tongue was one of the most erotic things that I had ever heard, and my cock stiffened again.
I knew that recovery time would be short, so I then went down on her. I was pleasantly surprised at how clean and fresh smelling her cunt was. I did not anticipate an old lady growler to taste and smell so good. I hadn't fucked a woman this old since I visited a whore in a Soho walk-up long ago during my misspent youth. She had smelled like she had used her cunt as an ashtray!
But Miss Croft had a cooch that smelled faintly of lavender. So I got stuck in teasing and licking at the relatively small opening until I could feel that she was close to coming; after that, I applied her vibrator until I felt her shudder, and she gently pushed my hand away. She told me later that although she had orgasmed before when using her toy, I was the first man in her life who had seen and been instrumental in her coming. A privilege indeed.
She was happy, relaxed, and hence compliant now, and it was time to get me some hardcore fucking going with Miss Croft. I put on a rubber and lubed up. I got her in the missionary position and tried to enter her, but she was an old lady and wasn't flexible enough. It felt uncomfortable this way, so I flipped her over and entered her cunt without a hitch, and as she was in no discomfort and seemed to be enjoying it, I upped the speed until I was ramming her quite deep and hard. I was really into it now and whupped her arse a bit which I think surprised her a little, but she just let out little cries, which was even more of a turn-on for me.
'This is my dream come true, Miss Croft, to fuck you hard like this. Do you like it up your bum, dear?'
'Yes, yes, it's fucking good. I like it, but please go slowly,' Miss Croft gasped. 'I haven't done that in years.'
'Okay, Miss Croft. I'll be careful; I replied as I slid my cock from her pussy and inserted the tip of my penis just inside her anus; I gently pushed and was delighted to feel my entire length disappearing deep up her bum. I was in seventh heaven.
I then stuck two fingers in her now wet and gaping cunt as I was gradually upping the pace until I was thrusting as hard as I could. Miss Croft groaned as I withdrew my old lady cunt juiced fingers and placed them into her mouth. Where she obediently licked them clean. Has this naughty old biddy been secretly watching porn, I wondered?
'Oh, you are my dirty old cunt, Miss Croft, aren't you?' I dared to whisper in her ear. She moaned and nodded as I grabbed her by the shoulders and gave an extra hard thrust. She squealed in what might have been pleasure or might have been pain.
'You've never been fucked quite like this, have you, Miss Croft.'
'No, never,' came her strangled reply.
'Well, now that I've given your teacher's ass a good fucking, now I'm going to fuck your cunt again.'
She moaned some more as I helped her over onto her back, spread her knees wide, whipped off the rubber, and plunged my rock-hard knob deep into her cunt. I think it was at this point that she maybe regretted this meeting, but she gamely gritted her teeth as I fucked her as hard as I could manage for several minutes until I came like an express train deep within her cunny. I heaved myself off her and dropped down beside her, feeling as knackered as I'd felt in a long time. But if I felt rough, it was nothing to Miss Croft, who looked like she had been buggered and fucked for a week by a marching army!
She expected me to leave at this point, but I had not finished with Miss Croft yet. I was determined to see yet more of those posh lips around my bellend, sucking me dry, and this time it was her mouth that I intended to fill with baby batter. I was surprised that she didn't tell me to 'fuck off', but no doubt she was too lovely and sophisticated to be so rude to her guest. I coaxed her back onto the bed and got her sucking me hard again and then to continue blowing me until I had filled her mouth full of my love juice. No doubt she was as shocked as I was at my virility and copiousness as she allowed my cum to drip down her chin onto her chest. Maybe she had been expecting a sophisticated spot of love-making WI style, but what she got instead was a good old-fashioned hard fucking. I sensed that we both would be walking like John Wayne on the. Morrow, but I think that she had enjoyed our little session. I certainly had!
'Darling boy, you're delicious,' she purred as spunk dripped down her face!
I would have gladly tried for a fourth round, but that would have been one pop too many for me and definitely for Miss Croft. So I quickly dressed, and with air kisses and promises that we must do it again, I left.
I knew I wouldn't hear from Miss Croft again, and I was right, but I didn't mind as it was a never-to-be-repeated one-off fantasy come true, and I didn't expect or want to repeat it. I'm not really into old ladies. Give me an eighteen-year-old Filipina lass with a tight body and an even tighter pussy any day.