One Step Behind

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A boy's best friend always seems to be one step ahead...
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JennyGently
JennyGently
3,299 Followers

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 of 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 in 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 sleep-over 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 Carline'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, and 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 on her virginity during her own eighteenth birthday party only two weeks before but had high hopes of 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 was 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 the came from my right-hand side.

"OooowwwWWW!"

I turned my head sharply so 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 heart strings.

"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 reach 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 friends' 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 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.

JennyGently
JennyGently
3,299 Followers
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