Chapter One

Most cuckold stories begin something like ‘I’ve always wanted to see my wife being fucked by another man but thought it would never happen.’

My story is a bit different. Before we were even a couple, I knew what it was like to watch Caroline being fucked by someone else. It was one of the things that made me desire her most.

One Saturday night back in 1978, at the tender age of eighteen, I watched as, only inches away from me, the love of my life lost her virginity to my best friend. I even held her hand while it happened and listened to the sweet sounds of that first, amazing penetration.

At the time her near-silent defloration was taking place, I didn’t know that the girl whose virgin blood was being spilled alongside me would go on to become first my girlfriend, then my wife, and the mother of my two children. I had even less idea that years later, I would hear those soft, sweet sounds many more times, more often brought about by the penetration of her sweet body by someone else’s cock rather than my own.

But as I listened to the soft ‘Uh-Uh-Uh’ that emerged from her throat as she was being fucked for the first time, I fell deeply and eternally in love and knew that however long it took, in the end, there could be only one girl for me.

Even if I wasn’t to be the only man for her.

***

Standing an unremarkable five foot four inches tall, Caroline has a figure that over the years has varied from curvy to full and back to curvy again. My wife has never been skinny, and I adore her for it.

Her hair, an equally unremarkable mousy brown, has varied from shoulder length when at school to boyish-short after our children were born before returning to its current youthful length and (with assistance) colour once again.

What made Caroline special then and makes her even more special now she is in her fifties, is the sparkle in her personality and the mischievous glint in her eyes that, on the right occasion and with the right man, she can still use to devastating effect.

I am still the right man on many occasions but no longer exclusively.

My wife has always emanated femininity, vulnerability and intelligence. On carefully planned occasions, she can project easy availability too; a powerful combination that demands the attention of any male that encounters her.

It demanded mine from the first time I met her when she sat at the desk next to mine on her first day at our school.

Although not the kind of girl to immediately attract all the boys’ attention, Caroline’s soft loveliness gets under your skin and grows on you. I had known her since we were both thirteen and we had been friends of a kind for years before I watched her losing her virginity when we were all still at school.

I had known Marcus, her first lover and my best friend since we were even younger.

With our parents stationed overseas in the Armed Forces, he and I had been sent to a boarding school in the East of England from the tender age of eleven. Although the school was mixed-sex, the number of girls in the first two years was small. Fortunately for us, that number increased substantially in the third year when studying in earnest for what were then ‘O’ Level exams began.

That was when Caroline and I first met. It wasn’t the best of beginnings.

The run-up to age thirteen is a difficult time for both boys and girls, what with puberty exerting its often-malign power, bringing spotty skin, body hair, greasy locks, uncontrollable erections and emotions, and of course for girls, the development of breasts and the arrival of full-on periods.

So when, on my first day in the third year, our alphabetically aligned surnames meant I was placed at a desk alongside a newly arrived frowning teenage girl, I simply did not know what to do or how to behave.

Of course, Caroline was no more pleased than I was. At the time, my skin left a lot to be desired and I was as gormless with girls as most boys of that age, so our first relationship was one of suspicious tolerance. But over the first few weeks of term, we came to appreciate each other’s abilities – mine in maths and science, hers in English, history, and everything else - and a kind of mutually beneficial alliance developed.

She would help me in class when I needed it; I would repay the compliment on the rather fewer occasions she needed my support. From there we began to chat about other things too, but more as friends in class than anything approaching a romantic relationship. There was no suggestion of a date taking place; we just liked each other.

As time passed, we became confidants to some extent as well as workmates. When I had a crush on a girl – or had been told a girl had one on me - I would seek Caroline’s advice on what to do, or on occasion enlist her help in arranging a supposedly casual meeting with the girl concerned.

She, of course, called on my help on far fewer occasions.

It was the sort of thing that happened, and no doubt still happens in every class in every school throughout the country. By the time we were both sixteen and yet more girls joined the school to study for ‘A-levels’, we knew many but by no means all of each other’s secrets but hadn’t exchanged even the lightest of kisses. 

It sounds conceited, but the truth is that Marcus and I were two of the school’s heartthrobs. Both tall and athletic, we were good-looking and played alongside each other in the First fifteen rugby team. As a result, we were never short of a certain amount of female attention, especially amongst the new arrivals who hadn’t known us in our younger, spottier days.

We would often double date too, going to parties, discos, or movies with whoever our girlfriends were at the time as a group of four.

The difference between us was that when it came to girls as well as rugby, Marcus believed in quantity over quality. Not confining himself to the prettier girls or more available, he had a predatory ‘who dares wins’ attitude that always seemed to put him one stage ahead of me in every game.

If I got to hold my girl’s hand, he would get to snog his.

If I got to snog my date, he would be fondling his girl’s breasts.

If I got to fondle breasts, he would have his hand inside his victim’s knickers, fingering her.

And if I got to finger my date, he would… well, more about that later.

Between us, we worked our way through a sizeable proportion of the female element of the sixth form, but the notches on his figurative belt were always more numerous than those on mine.

I told myself I disapproved of his attitude; that I was the gentleman of the pair of us, but the truth was, I envied him his considerable success.

It was only when he turned his attentions to my friend Caroline that I began to have serious reservations.

Caroline was by no means the most attractive girl in school but over the years she and I had connected with a level of friendship unusual between boys and girls. It was platonic, at least on my side, but when it looked likely that she and Marcus would begin going out together, the level of unease I felt surprised me.

Also eighteen and like me, unquestionably still a virgin, she had been loosely associated with no more than a couple of boys since she had arrived at the school, and even those were believed to have progressed no more than snogging and perhaps a little light fondling through her clothes.

As I knew well, Marcus took no prisoners. Caroline knew this too, so her apparent complicity was something of a puzzle.

At the time, I myself had my sights on Annabel, probably the best-looking girl in the school. Being probably the best-looking boy, it felt only right that I should have her on my arm and, if things went well, eventually in my bed. Having had a string of unsuccessful suitors, access to her knickers was known to have been denied to all but one or two sets of fingers and absolutely no erect cocks.

She was, however, known by several boys to be an enthusiastic kisser. It was a chink in her armour I believed I could open and exploit, and I still had hopes that my more subtle, patient approach might yield results.

So, as we all came of age and entered the Upper Sixth form, though by no means a dare or a bet, my closest friend and I were involved in an unspoken challenge.

With the loss of two female virginities (and my own) as objectives, could either of us reach our goal?

And if so, who would be first?

Chapter Two

The answer to that question was as predictable as the rest of our friendship had been; we both succeeded but I came a clear second place.

My best female friend Caroline lost her virginity to my best male friend Marcus at quarter to three in the early hours of a Sunday morning in June 1978. She and Marcus were lying on rather than inside their sleeping bags alongside me and my new girlfriend Annabel on the lounge floor of her family house on a large farm in North Lincolnshire.

We had spent the evening celebrating her eighteenth birthday with a party to which two dozen of her friends from home and school had been invited.

As the school we attended was a boarding school, many of us lived some distance from Caroline’s house so a sleepover had been essential. We had all been dropped off by our parents or older siblings with the necessary equipment to cope with a night on the carpet and a good deal of well-concealed booze to ease the atmosphere.

Sleepover parties were familiar events during the school holidays and had been for several years. The difference this time was that at eighteen, there would be a lot more going on in the darkness than mere midnight feasts and the tentative sipping of illicit alcohol – though that had played a significant part in enabling the sexual activities that were now taking place throughout the house.

The party had gone well. There had been plenty to eat, loads of dancing to Caroline’s parents’ impressive Bang & Olufsen hi-fi, and rather more alcohol than those parents had intended there to be, most of it coming to light after they had discreetly taken themselves off to bed.

Once dance music had been replaced by slow, seductive tones and the lights lowered, the real work of the evening could begin; that of seduction, consummation, or the reinforcement of existing sexual relationships.

Although the sleepover group comprised six girls and four boys, we were in fact five couples, four established: one brand new. Caroline and Marcus had been together for several months and wore each other’s necklaces under their shirts. I had assumed they had been fucking for a long time but, as my friend told me gleefully the following morning, this had been their first successful attempt at proper sex.

Annabel and I had been together only a few weeks. As far as I knew, we were both virgins too; at least I knew I was. The resistance I had met trying to get more than just my fingers into her knickers suggested, as per her reputation, that Annabel’s hymen was still very much intact - though the number of times those fingers had succeeded must have done it considerable damage.

Still, she was enthusiastic about those things she was prepared to do with me and for me, so until that night, I had had little to complain about.

In the dining room next door were Nicky and Duncan, the longest-standing couple in the group. They were known to have been shagging for a few months at least and would certainly be doing it again that night if the body language between them was anything to go by.

In the room with them were Annie and Colin, two friends who we all knew fancied each other like crazy but until that night hadn’t had the courage to do anything about it yet.

Getting them together had been one of the objectives of the party; they had been put next to each other during dinner and had been placed in the same room as Nik and Dunc to encourage them to finally get physical. The plan seemed to be working; they had certainly got well into snogging and groping before we had separated rather drunkenly for our various rooms, supposedly to sleep.

It looked as if they might go further still during the night so, from that point of view too, the party had been a success.

Upstairs in the bedroom farthest from Caroline’s sleeping parents were Susie and Sarah, the lesbian couple everyone knew about, but no one talked about, least of all to their parents. What they might be doing with each other I in my naivete could only guess at, but they had been inseparable almost from the first moment Sarah had joined the school three years ago.

So, with every aspect set for maximum seduction and teenage libidos set to overload, it wasn’t surprising that progress was being made and made rapidly all around me, especially by my friend Marcus with Caroline on the long sofa alongside that on which Annabel and I lay.

At the time, my understanding of that progress was complicated by the fact that the middle fingers of my own left hand were deep inside Annabel’s wet, strong-smelling vagina, and her tongue was deep inside my mouth. I had completely failed in my attempts at her virginity during her own eighteenth birthday party only two weeks before but had high hopes for this second opportunity.

On the face of it, I had got the better deal. Annabel was simply stunning; tall, slender, blonde, blue-eyed with simply massive tits and who wore the shortest school-uniform kilt in the year. Any red-blooded schoolboy might have given his left testicle to have his fingers and tongue where mine were at that moment, with the promise of one day having his cock take the place of his fingers deep in the most desired vagina in school.

Indeed, that event might have already taken place had it not been for Annabel’s natural hesitance to lose her cherry and my own lack of self-confidence in persuading her to take that last, crucial, persuasive step – one which would relieve me of my own virginity in the process.

The progression of our sex life had therefore halted at oral sex and mutual masturbation. I sincerely hoped it was only a temporary pause on the road to full-on sex, but I didn’t have the confidence to force the issue, and besides, we were both very good at bringing each other pleasure where we were.

As we lay on the floor in the candlelight, I was trying hard to ignore the sounds of pussy-fingering and cock-pumping taking place alongside me and concentrate on giving Annabel the orgasm she had come to expect from my own increasingly confident fingers.

I was making good progress; the noises she was making as I fingered her were a great deal less sweet and innocent than Caroline’s soft purring. Indeed she soon abandoned any attempt at kissing and twice buried her teeth in my lower neck in increasing passion.

From the trembling in her body I knew that, if I kept on going, a messy, smelly, sticky, teenage climax would soon burst onto my hand, leaving me with a temporarily satisfied girlfriend and the dubious trophy of fishy fingers for the next two days.

“Ah! Ah! Ah! MmmMMM!”

I persevered, working my fingers deeper into her vagina, my palm on the tip of her engorged clitoris almost by accident.

“MmmmmMMMM!”

Her body flexed; her jaws closed.

“Ouch!”

I exclaimed aloud as Annabel’s teeth closed hard on the nape of my neck once again, but she was beyond hearing or caring. The croaking gasps that escaped her throat and the sharp pain of her teeth breaking the skin of my neck were accompanied by a gush of strong-smelling juice from her blonde down-covered vulva onto my active fingers.

“OoooowwwWWWYESSS!’

Annabel came helplessly in my arms and on my hand. Her body flexed, her heels kicked out and her thighs tightened hard on my forearm as her orgasm took control. From our previous encounters, I knew better than to stop, plunging my fingers deeper into her already-wet passage, twisting them from right to left, and sucking hard on her one exposed nipple.

“OhGod! OhGod!”

The result was pleasing; a second wave of climax overcame her, making her slim body writhe and squirm as yet more pungent fluids flooded from her.

‘Plap-plap-plap-plap’

The sounds emanating from between her legs as my fingers collided over and over again with the soaking wet folds of flesh between her upper thighs was so arousing that I almost came on the spot too. Indeed I might have done so had I not been distracted by the loud gasp of shock and surprise that came from my right-hand side.

“OooowwwWWW!”

I turned my head sharply to see Caroline on her back, her short skirt around her waist, her panties around her left ankle, and her legs wide apart. Marcus was above her, his jeans and pants were around his knees, his bare hips partly hidden by her raised thighs.

From the look on her face, her wide-open eyes, and the expression of triumph on my best friend’s face, there could be only one conclusion; Marcus had just thrust his erect cock into Caroline’s virgin vagina.

He had taken my friend’s cherry right alongside me.

Caroline was staring wide-eyed up at him, her sweet face a picture of pain and shock while Marcus, biting his lower lip, wriggled his hips as he struggled to find a comfortable lie for his cock in her freshly violated vagina.

Chapter Three

“Oh, that was so good! Do you love me?”

Annabel’s dreamy, post-orgasmic voice brought me back to the matter quite literally in hand. My fingers slipped slowly from her dripping vulva and I took her in my arms, kissing her full on the lips as her trembling began to subside.

“You know I love you,” I lied between clumsy, wet kisses.

But my mind was fixed on the noises that were beginning to come from the couple on my right.

‘Slap!’

“Ohhh!”

‘Slap-slap! Slap!’

“Ohhhhhowwww!”

‘Slap! Slap! Slap!’

“Mmmm!”

Hesitatingly and without discernible rhythm, Marcus had started to thrust in and out of Caroline’s vagina. That’s when I first heard the softest, sweetest noises that were to drive me crazy throughout the rest of my life.

“Uh-uh-uh-uh!” 

No wailing, no moaning, no protestations. A mix of pleasure and pain which twisted my heartstrings.

“Uh-uh-uh-uh!”

Marcus was beginning to establish some kind of rhythm.

“Uh-uh-uh-uh!”

Slap! Slap! Slap! Slap!

“Uh-uh-uh-uh!”

Slap-slap! Slap-slap!

His thrusts increased in both speed and power, as did the soft sweet sounds.

“Uh-uh-uh-uh-uh-uh-uh-uh!”

“Mmmm! Caroline you’re so fucking tiiight!”

I was to hear those soft, distinctive sounds many times over the next decades, coming both from below and alongside me but at the time, I did not know this.

Nor did I understand that the pleasure I was deriving from watching and hearing the girl I adored being fucked by another boy right in front of me, was not at all normal, even for a confused eighteen-year-old boy whose hormones were hurtling around his body like wildfire. 

As I listened, Anabel’s head fell to my groin and I felt the head of my very erect cock being engulfed by her hot wet mouth with its active tongue. It felt amazing but, still fascinated by the defloration that was taking place so close by, I couldn’t completely tear my eyes away from the mating couple alongside us.

Caroline lay on her back, her legs spread, Marcus thrusting away into her body using all the energy he could summon, but with no idea of technique.

Caroline’s eyes were fixed on his, but as I turned my head towards her, she turned hers too until our eyes were locked onto each other. There they remained as Marcus’ thrusts grew faster and wilder, driving her bodily across the floor.

Then, our eyes still locked together, and with my erect cock in her friend’s mouth and my best friend’s cock deep in her vagina, the girl I finally realised I adored, reached out towards me with her left hand.

Instinctively, I extended my arm to meet hers. Our fingers touched and then quickly meshed together into a fist. Caroline’s grip on my hand was almost painfully strong. She looked into my eyes with a pleading intensity I had never seen before as her freshly deflowered body was battered and the soft sounds of an inexperienced copulation filled my ears and twisted my heart.

“Uh-uh-uh-uh-uh-uh-uh-uh!”

Slap-slap-slap-slap-slap-slap-slap-slap!

The lounge in which Caroline’s virgin blood was being spilled – literally as the pink stain on her parents’ new, shag-pile rug showed the next morning – was large and lit by only a handful of candles. In the half-light, her eyes glowed with an intensity of passion and desire that I had never seen before, her huge, deep black pupils fixed on mine, her hand gripping my fingers like a vice, as her body was pummelled by my closest friend.

Meanwhile, at my own groin, Annabel was working overtime on my erection, her hand pumping my shaft hard as her lips and tongue played with my swollen head. It would not be long before I came and, as had happened only once before, my entire load of semen would be taken into Annabel’s eager mouth before being swallowed wholesale.

From the noises coming from his mouth and the heat growing at the base of my cock, it sounded as if both Marcus and I would be finishing at about the same time – and that time was approaching at lightspeed.

A strange kind of simultaneous orgasm indeed.

“Oh God! Oh fucking Hell, Caroline, you’re amaaazingggg!”

As Marcus began to ejaculate deep inside Caroline’s completely unprotected vagina, Annabel’s free hand grasped my tight sack. Her tongue licked around the ridge under the head of my cock as the fingers around my shaft tightened and pumped as hard and fast as they could.

“Fuck! Oh yes! Oh fuck!”

My own climax rushed upon me, sending a fountain of teenage semen upwards and into the welcoming mouth of the hottest girl in the school. Annabel sucked it up without hesitation, drawing every last drop between the lips I had kissed so hard and so often.

As I came in her friend’s mouth and Marcus came in her vagina for the first time, my fingers were still clasped around Caroline’s and our eyes were still locked tightly together.

Chapter Four

So that’s how my sex life began, like so many aspects of my life, a few steps behind Marcus.

He had taken Caroline’s cherry with witnesses and had thereby immediately become a boy to be respected within the school. With the lack of fairness between the sexes prevalent at the time, Caroline had equally promptly, acquired a reputation as a slut.

Given what was to happen later, this title was perhaps a little prescient but at the time it felt grossly unfair to me, her friend and increasingly devoted admirer.

Of course, never one to be beaten, I redoubled the attention I paid and the pressure I put on Annabel. She resisted nobly but I persevered, arousing her with my fingers more effectively than ever before, whenever we got the chance. She resisted still, but I could feel that resistance beginning to crumble.

The final breach came during another sleepover party at another friend’s house. There, in the small hours of the morning on a mattress on the spare bedroom floor - after my fingers had done their preliminary work more thoroughly than ever before - I dared to use my mouth between her thighs for the first time.

At first, the strong aromas and even stronger flavours that filled my mouth and nose as Annabel’s vaginal juices flowed, took me by surprise. But the extraordinary strength of her reaction to the touch of my tongue on her slit overcame any initial revulsion I might have experienced and drove me to concentrate harder on the job at hand.

Working my mouth inexpertly for all I was worth, I felt the new and mind-bending sensations of a girl’s vulva on my tongue. The metallic taste of her secretions; the soft folds of the inner lips that guarded her entrance, the seemingly endless depth of her vagina as I thrust my tongue deep into it; the strange, fleshy collection at the apex of her slit.

I had almost no idea where her clitoris was but with completely undeserved luck, a long upward stroke of my tongue raised its meaty hood and revealed the hard nub beneath.

The loud gasp that came from Annabel’s mouth and the way her thighs closed hard on the sides of my head told me what I needed to know: I had found it by accident.

Once I realised I had hit the sweetest of sweet spots, I worked at it with my tongue for all I was worth.

The climax that followed took us both by surprise. Annabel yelped, bucked, and grabbed my hair so hard I was sure handfuls would come out. I attacked her slit again with similar results, her cries growing even louder.

For the first time, over the pungent taste of her initial arousal, I tasted the unforgettable nectar of a girl’s bitter orgasmic vaginal juices flowing directly in my mouth, her flailing thighs spreading the strong-smelling goo all over my cheeks and jaw as she came and came helplessly.

After this, Annabel was completely unable to resist my clumsy attempts on her virginity. While she was still stunned, I mounted her as Marcus had mounted Caroline and, with her dazed but clear acceptance, thrust my unprotected cock into her weeping vagina.

I can still remember the incredible, almost unbelievable feeling the first time my erect cock entered a girl’s warm, smooth, tight vagina and the way that girl responded to being penetrated for the first time.

Over the past months, I had fingered her so hard, so often and so deeply that there could have been little of Annabel’s hymen left. All the same, the sensation of having a real, full-sized penis in her vagina for the first time was an even greater shock than her first oral orgasm.

Annabel’s whole body went stiff, her legs straightened sharply, her eyes fixed on mine, but she made no attempt to stop me. I stared back, for a moment frozen in shock.

After so long trying, my erect cock was finally inside a girl’s vagina. What on earth did I do next?

I had been so fixated on losing my own cherry, I hadn’t thought about what fucking a girl might actually entail.

Fortunately, Annabel had no idea either, so was in no position to judge my lamentably weak and short-lived performance. As she became more accustomed to the unfamiliar presence in her body, her legs began to bend and her body became if not actually relaxed, then at least a little less rigid. Her knees parted further under pressure from my thighs, giving me enough freedom to draw back and make my first clumsy thrust.

Annabel gasped as I forced myself into her, her legs closing as if to prevent my progress. I pulled back and thrust again, a little more controlled this time. She gasped again, her knees becoming a little less of a barrier.

I tried again and again. By the time my fifth and sixth thrusts had made their way into her formerly virgin vagina, her resistance had all but evaporated and, though not playing an active part in her defloration, Annabel’s eyes told me that she no longer wanted to resist.

After that, the way was clear for me to get as close as I was able to my first proper fuck. Annabel bit her lip hard as I thrust in and out of her body maybe a dozen times before she began to moan and wail, much as she had when I fingered her but louder and with a sharp, aroused edge that I had not heard before.

It turned out that in the throes of defloration, Annabel made even more noise than when she reached orgasm on my fingers. Her wails became screams of arousal, then grunts of encouragement.

I fucked her harder, the noises emanating from our conjoined groins and from her open mouth growing louder and louder until the familiar burning feeling between my thighs descended with an intensity I hadn’t known before.

As my body was wracked by approaching climax, what passed for rhythm broke completely, and less than a dozen strokes later, my teenage stamina gave up completely and I came copiously, deep inside her body.

Her tears afterwards were so loud that not only must every one of our schoolfriends realised what was happening, the parents of the girl in whose house the sleepover was taking place must also have been woken.

It can only have taken seconds for them to understand who was wailing and why but thank God, they stayed upstairs and, apart from making sure Annabel was okay the next morning, said and did nothing.

As it was, Annabel was more than okay psychologically and had willingly accepted a repeat performance in the small hours of the morning, which I had been very pleased to provide. This time her wails were more in pleasure than in fear or in pain.

After the sleepover, my reputation was made too. From that moment on I was the boy who had popped the most desired cherry in the school; a badge to be worn with pride.

I did not let on that in relieving Annabel of her virginity I had also relieved myself of my own. Only I needed to know that little fact. Let the rest of the school believe me to be Number One Stud for a while.

Only Caroline gave me a knowing smile that suggested she and I now shared another secret. I blushed and my heart ached.

Chapter Five

For the next few months school occupied almost all our attention. As Annabel’s official lover instead of just her boyfriend, I had a level of respect among my peers that I was not used to, and access to Annabel’s wonderful body whenever the two of us could sneak off in secret.

This we did frequently, in the cricket pavilion, in the long grass beside the canal, in both her bed and mine, once even in the gym over a vaulting horse.

We were young and stupid, fucking carelessly and without any thought of protection, almost every encounter ending with my shooting my entire load into her completely exposed and vulnerable body.

It should have been the happiest time of my life, but it wasn’t.

Although the male half of the school saw me as the lucky bastard who was fucking the hottest girl in town, for some reason it wasn’t enough. Yes, the sex was good and getting better. Yes, I was the envy of every red-blooded male in the school but there was something missing. Something big.

Far from being the luckiest boy in the school, I couldn’t help seeing myself as the boy who had watched the love of his life being deflowered by his best friend. And who had enjoyed watching it.

No, that’s not strong enough. Who had loved watching it!

What made it worse was that Caroline kept giving me those knowing looks throughout the whole period; as if she could see through all the bullshit and straight into my soul.

As it turned out, she could and still can!

Meanwhile, the love of my life and her boyfriend were being at least as active as Annabel and me.  On many occasions we double-dated, drinking illicitly at the far edge of the sports fields then all four of us ending up in the Cricket pavilion where, in the same room and on the same randomly placed gym mats, we fucked our respective partners with far more enthusiasm than technique.

Marcus and my grunts at ejaculation were all but drowned out by Annabel’s wailing as I fucked her for all I was worth, but as I emptied my balls into her skinny body once again and heard my best friend reaching climax alongside me, all I wanted was to hear Caroline’s soft panting sighs, to look at her wide-open thighs and deep into her soft brown eyes as my best friend fucked the living daylights out of her.

This, according to Marcus, was a revelation. Once her virginity had gone, Caroline had apparently changed dramatically from a hesitant virgin into a girl whose enthusiasm for sex was passionate, demanding, and exhausting.

From the things he told me in private, and from what I saw and heard in the pavilion, sweet, quiet Caroline threw herself into their copulations with energy, daring, and imagination, becoming if not the slut her reputation suggested, at the very least a girl driven hard by the collection of organs between her thighs.

Having heard them together with my own ears, I had no reason to doubt my best friend, but his words brought me more pain than either he knew, or I had expected.

***

So, our last term at school ended with four fewer virgins, and the summer holidays began with Marcus and Caroline as one item and me and Annabel as another.

It was to be a summer of love in every sense. Being a boarding school, our homes were all some distance away from each other – in my case in another country so we couldn’t be with our other halves as often as we would have liked.

Nevertheless, we had visits and sleepovers aplenty; I would stay with Marcus or at Annabel’s and we all got together often enough to keep the relationships going, at least physically. And of course, as we became more sexually experienced, that side of our lives grew more satisfying.

It sounds strange now but, probably because of the way our sexual awakenings had happened, we seemed most relaxed sexually when in a group of four rather than as separate couples. It did not feel in any way wrong for me to fuck Annabel in the same room in which Marcus was fucking Caroline as if each couple was learning from the other, or perhaps each one of us was learning from the other three.

If it was a learning process, it worked well. The first time I made Annabel cum with my cock is something I shall never forget. The first time I heard Caroline reach one of her breathless, choking climaxes under Marcus is an even more profound memory. 

But all good things must come to an end. Come September, it was time to go to University and for the gang of four to separate; Marcus to study Chemistry in Edinburgh, Annabel to read French in Exeter. Both of these were a long way from London where Caroline and were both bound; to the same city but to different Universities, me to study Engineering, Caroline to study History.

There was a last night, farewell sleepover in Caroline’s parents’ house during which I tried to make up for the coming weeks of abstinence by fucking and cumming in Annabel no less than four times in a single night, setting a pace which Marcus and Caroline struggled to match.

Oh, the joys of youth and short recovery times!

Then, swearing eternal friendship to each other and fidelity to our respective partners, promising to keep in touch and see each other often, we went off to our respective Universities.

Chapter Six

First year University life back then was not the sex-charged, alcohol-fuelled binge it seems to have become now, but there was no shortage of things to do and parties to go to. All four of us seemed to take full advantage of this so our well-intended plans to keep in touch became less and less well-kept.

These were the days before mobile phones had even been invented, let alone become the universal accessories they are now. Email didn’t exist, there was no Facebook, Instagram, or Twitter; communications had to be by post or by pre-arranged phone calls from public call boxes. Cars were expensive too; only a handful of students had one and almost none of these were in London.

Keeping long-distance relationships alive in these circumstances was a huge challenge and surprisingly quickly, the closeness of the gang of four began to crumble.

The excitement of living and studying in London was for me, almost overwhelming. My student accommodation was right in the centre, placing my spinning provincial head in the heart of all the Big City had to offer. There were so many people, so many places to go, so many things to do – and so much money needed to do them all.

The Hall of Residence was full of interesting fellow students too, from all over the country. I made new friends easily, staying up late at night talking, drinking, and eating endless quantities of that student staple diet: toast.

And there were so many girls!

Coming from a boarding school where female students were in such short supply, the number, variety and apparent accessibility of University girls was simply astonishing. Though floors and corridors in the Halls of Residence were separated by gender, all meals and ‘freshers’ events were fully mixed. Even on my male-dominated Engineering course, there were half a dozen reasonably attractive girls.

With so many distractions, undertaking any form of study was enough of a challenge, so to my shame, keeping in touch with all my old school friends took second place. In my defence, they seemed to find it equally difficult to keep in touch with me, but wherever the blame lay, a certain distance began to develop.

Unexpectedly, Marcus and I lost touch very quickly. The pressures of our courses added to the huge distance between us made communication difficult and expensive. After only one visit to London from his student flat in Edinburgh, it was clear that this long-distance friendship was going to be very tough to maintain.

Caroline was also studying in London, but in big cities, people tend to run on rails, and apart from a couple of coffees in our first two weeks, our paths didn’t cross. To be fair, she tried the hardest of us all to keep the gang together, but after a few months and a poor response from the rest of us, she lost the will to continue.

Even my relationship with Annabel was put under strain.

Whatever the distractions, no teenage boy is going to completely neglect the girl he last had sex with, or the girl most likely to be his next fuck, so I did make what for me, was a significant effort to keep in touch with Annabel, phoning once a week and writing whenever I remembered to do so.

Annabel was much better, at first sending me two or three letters a week, covered with pink love hearts and full of promises of exciting meetings to come. But after a month, even these had dwindled to at best one rather less emotional page for me to masturbate to at the weekend.

The problem was that her Exeter student hall was several hours of expensive rail journey from my London bedroom. We spoke on the phone once a week and sent each other the occasional letter which kept things going, albeit at a much lower intensity than before.

Then, six weeks into our first term away, I paid British Rail a small fortune and visited her for a weekend in her new environment.

On the face of it, the weekend was great. When she met me at the station, Annabel looked every bit as drop-dead gorgeous as I remembered her, and seemed pleased to see me too, though from the beginning it was obvious that time apart had introduced a bit of reserve to our first embrace.

The weekend flew by; I met lots of her new friends and with them, discovered an amazing city I had really only heard of before. Her group of closest friends was great fun, clever and good company. They welcomed me warmly, but I didn’t get most of the private jokes, and couldn’t help feeling that I was very much an outsider.

As you would expect with a girl as intimidatingly good-looking as Annabel, she had surrounded herself with a clique of equally attractive people, both female, and male. As an outsider, I could see the complicated interactions going on between them - perhaps even better than they could themselves.

By the Sunday morning, I had formed clear views about who fancied who and how badly, who had already been inside whose knickers and was trying to keep it secret, and even whose adoration was unrequited.

Unsurprisingly, a lot of that adoration was directed towards my girlfriend, and more than a little envy was directed at me as a result.

There was more than a little hero worship going on too, something even Annabel was not immune to. Indeed on Saturday afternoon, she insisted we joined the gang gathered on the touchline to watch Simon and Hugh, two ludicrously well-built and good-looking friends, play rugby for the University’s second fifteen before heading into town for an evening in the pubs to celebrate their victory.

We all got drunk together and I really enjoyed the experience. Hugh was a hard beer drinker, something he blamed on his Welsh heritage. He and I got on well and sank several pints together, but Simon seemed to be avoiding me, choosing to spend most of the evening with the girls.

And who could blame him? Annabel looked simply stunning all weekend, as did the other girls – some of whose attention came my way too - but despite the two of us fucking three times in her narrow student bed, I could tell something had changed between us.

It wasn’t anything physical; her legs were as long and slender as I remembered, she spread them as wide as I remembered, her nipples were as dark and hard and her vagina as deep and tight as I remembered.

The energy of our copulations was as raw and powerful as before too, but not even the loud, familiar wailing that filled her bedroom as I hammered my cock into her over and over again, could prevent me from feeling that some of the original passion had gone.

When Sunday afternoon came, even though her body reeked of the sex we had enjoyed barely an hour before, the goodbye kiss she gave me on the station platform was definitely not as passionate as the embrace we had enjoyed before departing for our respective colleges.

I returned to London feeling a little hungover, very satisfied sexually, but with a nagging doubt inside me.

Chapter Seven

It was around this time that my Engineering course began to be seriously demanding. Having given us half a term to get used to University life and study, and for those who weren’t going to make it to drop out, the screws were really put on us in terms of work.

Lecture followed lecture, worksheet followed worksheet and the time spent in laboratories grew longer and longer. Parties grew fewer too, and the need for weekend work meant the opportunities to travel all but disappeared.

It was just before Christmas when I learned - via a friend, not from her directly - that Annabel in Exeter had not only cheated on me with Simon, she had been doing so both before and after my visit, and they were now in a steady relationship.

I had been dumped without even knowing it.

I tried to phone her but she wouldn’t take my call. I wrote a short letter; the brief, terse note from her that arrived a few days after that, confirmed that she and I were no longer an item.

The shock and emotional pain were horrible, but as a proud young man, I could not let it show.

What I could also not do was forget it and move on. Try as hard as I might, I could not stop thinking of her and what was now happening all those miles away.

Another lucky boy now knew what it felt like to be between those long slender thighs and feel that deep, tight vagina around his cock. Another boy now knew the extraordinary, animal noises she made when being fucked.

Had he fucked her just before I arrived in Exeter? Did they fuck as soon as I had left?

Oh, Christ! Had she fucked us both on the same day? Within the hour?

Night after night my mind was filled with images of the girl I had known; on her back with Simon’s strong, powerful body between her thighs; on all fours with him kneeling behind her, thrusting into her doggy-style as I had done; of her straddling him, her slender body fully impaled on the monster cock that my twisted imagination had endowed him with.

Worse than this, my own body was responding in kind.

Every night, as surely as these terrible images tormented my mind, my cock would join in the cruelty by becoming painfully hard. The more I imagined her being fucked by Simon, the more persistent my erection became.

There was no denying the massive arousal that Annabel’s infidelity was producing in me. The agony of picturing her infidelity was perversely but inextricably mixed with almost unbearable arousal in a way that was both physically and emotionally painful.

No amount of masturbation and ejaculation could free me from this torment, and believe me, I did it a lot.

I tried to console myself with the knowledge that, however many boys she fucked from now on, Annabel’s cherry belonged to me and that could never be changed. The memories of that first fuck went some way towards reinforcing my battered male ego, but at the same time, reminded me of what I would no longer be able to enjoy so instead, I tried to distract myself.

For a short time, I tried the time-honoured route of excessive alcohol with my friends. Then when this didn’t work, I tried excessive exercise, running alone through the city streets. All this did was give me more time to think about my grievance, so finally, I embarked on a quest for excessive sex.

This finally brought me to one of the darkest parts of my past, and to a naive girl called Rachel.

Rachel was sweet rather than pretty but had a nice, rounded body. Living in the same Hall of Residence as me, I had met her via friends during the first week of term. She was shy, ridiculously innocent, and credulous, but above all, the poor girl had had a major crush on me since term started.

That crush gave me the chance I needed and proved to be her undoing.

I have to admit that I behaved shamefully. Taking no prisoners, I romanced, seduced, and deflowered her, all on the night of the Hall Ball. Then, having taken her cherry in her Hall bedroom so noisily that her friends couldn’t possibly fail to know what was happening, I fucked her hard and frequently almost every day for three weeks, with no protection and no attempt to conceal the fact.

Why did she let me do it? It was the old, old story. Having surrendered her virginity, she was madly in love with me, wanted me to love her forever in return, and was prepared to let me do anything I wanted to her achieve this.

What I wanted was good, frequent, adventurous sex to stop me thinking about Annabel being fucked by Simon. Despite having Rachel in every way I could imagine – yes, even including anally - neither of us got what we wanted.

Okay, for a short time, I got plenty of sex, but the wound opened up by my dumping was too fresh and too deep to be healed by sex alone. My head was still stubbornly full of Annabel, and I was incapable of loving anyone – not even a girl as lovely as Rachel undoubtedly was.

Even with my cock balls-deep inside her tight, inexperienced cunt, every time I closed my eyes, all I could see was Annabel - usually lying on her back, Simon’s fit, athletic body rising and falling between her pale, slender thighs, her blonde head thrashing from side to side in the throes of sexual ecstasy.

Several times, the anger and passion this vivid image produced, drove me to fuck Rachel almost brutally. It must have been painful for her, but having only had sex with me, she probably assumed this was what all sex was like.

In the end, my conscience finally won. I couldn’t maintain the lie any longer and told Rachel the truth; that I was damaged goods and would never be able to give her the love she needed.

Her tears were real and heartbreaking, and we broke up just before Christmas.

My behaviour was appalling; even now I am ashamed of myself. Rachel, if by some million-to-one chance you are reading this, I am truly sorry. You deserved a lot better than me.

At Christmas, feeling disgusted with myself, shunned by Rachels’ friends, with an uncommunicative best friend of my own and no girlfriend on the scene, I went abroad to spend the festive period with my parents.