My parents got divorced when I was 8. My older sister wanted to stay with my Mum. Whilst, surprisingly for those times, I chose to live with my Dad. For a few years we muddled along together until, when I was 11, he met and moved in with his new partner, Jayne.
It was, as is almost invariably the case, a difficult transition for us all. But I grew very fond of Jayne. My Mother (and my sister) had been a little brash and forward. Whilst my Dad was calmer, serious and much more reserved. And I was, in many ways, a carbon copy of him.
Jayne was a much better fit for my Dad. And, as I came to realise, probably for me too. She was quiet, almost diffident. Dressing and acting very conservatively.
So, at the age of 18, in my final year of school, I was happy and contented (though sexually frustrated) with our current living arrangements. Certainly happier than I’d been when my parents had been constantly rowing a decade or so ago.
I went to an All Boys grammar school in our small town. It selected on academic achievement. So it probably contained more than it’s fair share of studious, socially awkward, pupils. But, even by those standards, I was an outlier.
I was in the top 10% academically. But in the top 1% for shyness and clumsiness around girls. I loved the opposite sex. But I had absolutely no idea how to talk to them. Probably because I had absolutely no confidence at all in my physical, or particularly social, prowess.
Jayne came with a “plus 1”. She had a daughter, Sally, her only child from her previous marriage.
Sally fitted in well to our rather dull quartet. She went to the equivalent All Girls grammar school. Sally was just a few months younger than me and we were in the same school year.
Probably taking a lead from her Mum, Sally did nothing at all to enhance her looks. Her dark, almost raven black, hair had a corkscrew perm. And huge, “milk bottle top” spectacles. Both of which, looking back on, even years later, she still cringes about. Her skin was pale and (unlike my acne scarred complexion) almost perfect. But, because her hair was so dark (and as I was to discover she was quite hirsute) it showed on her arms and legs. Which I came to realise she was really embarrassed about. All of that said, strip away the dodgy perm, glasses and unwanted hair and beneath it I suspected (and subsequently came to discover) she really was extremely attractive.
What she did have, though also did her best to hide, was an absolutely killer body. Partly genetics I guess. But also, in large part, down to the hours she spent swimming competitively each week.
I can clearly recall going to see Sally in a swimming gala. As she stripped off her tracksuit and took her place on the starting blocks at poolside I was astonished how shapely and womanly she looked. Everyone competing was fit. But I honestly thought Sally had the best body of them all.
Whilst we were not blood relatives, the character similarities between us were uncanny. Sally was bookish, extremely clever and hard working. She also, like me, seemed to lack any confidence about her looks. And was painfully shy with boys. So there were certainly no boyfriends on the scene. In fact, she seemed to have few close friends at all. The two of us, I’m afraid to say, were rather “grey” characters. Largely in the background, certainly in social settings.
Consequently, we became very close. Certainly Sally was the only girl I ever had any meaningful conversations with. Though even these were usually connected with schoolwork, politics and hobbies. I don’t recall in those teen years that we ever shared any confidences in each other.
But, clumsy social oaf that I was, I really enjoyed her company. And, I was pretty sure, she mine. We spent more time with each other than we did with anyone else. And there was a comfort between us. And, I felt, a warmth. Though that was entirely unsaid. And certainly not demonstrable.
I’d come to realise that her Mum and my Dad getting together, and consequently her moving in with us, was the best thing that had happened to me in my pretty featureless life so far.
Late one afternoon Sally and I were home together, before our respective parents got home from work. It was a little unusual for us to be around at the same time. As, typically, one or both of us would be in some after school activity.
I wasn’t especially coordinated, or sporty. But I was a strong runner and was often doing cross-country. For both the school and the local Harriers athletic club. Sally, meanwhile, as I commented above, was an excellent swimmer. And several mornings and some evenings, went to swim club.
But, many (in fact all) of our other activities were geeky. For example, chess club, debating society, Oxbridge application preparation etc. We really were a spectacularly nerdy pair.
That afternoon Sally had changed out of her school uniform and put on a tracksuit and a tee shirt. The tee shirt was long and baggy. But the tracksuit bottoms were tight, figure hugging in fact. Though the tee shirt, frustratingly I was almost surprised to admit, was so long that it pretty much covered her buttocks. Though, every now and again it would ride up. Providing a view of her spectacularly tight buns.
Over the last few months I’d become increasingly aware of the excellence of Sally’s figure. Not that she did anything to showcase it. Quite the opposite in fact.
We were in the kitchen, which looked out on to our small back garden. This backed on to fields and the edge of a wood. So we regularly had myriad birds flying in and out of it. Attracted by the nuts and scraps we put out for them.
As further evidence of our bookish tendencies, we took delight in identifying the multiple species that visited. And had purchased a few textbooks to help us do this. Looking back it really is hard to imagine any ways we could have been more nerdy. With trainspotting about the only “geeky” pursuit we didn’t practice!
“Look, Jack, I think there’s a pied flycatcher,” Sally exclaimed. “That’s the first of those I’ve ever seen.”
Leaning over the sink to give herself a better view out of the window, she called me over. As she did, her tee shirt rode up and I had an uninterrupted view of her arse. Albeit, fully dressed of course. But it just looked so perfect and inviting.
I stood side by side with Sally, craning to get a better view of this rare species. Our hips were touching and I put a hand on her back to steady myself, as I bent forward to get the best view of it.
To this day, I’ve no idea what prompted me – or gave me the courage – to do what I did next. Apart from, I guess, the hormones that were raging inside me.
But, as I observed this small bird, nibbling on our garden treats, I moved my hand down and started to cup Sally’s buttocks. Gently and tentatively at first. But, clearly, it was a sexual act. Particularly as I got a little bolder.
Nowadays, in the age of Me Too, I wonder if I’d have been prepared to take that risk? Though I guess with the amount of misogynistic porn that’s available, I may have been more influenced the other way. And been a little more forceful?
Either way, that point is moot. As there I was, with my hand caressing (if you were being kind) or clumsily groping (if you were being more accurate) my step-sister’s arse. And it really did seem to be a very fine arse indeed. Though, at that time, I had absolutely nothing to compare it to.
Sally froze. But said, or did, nothing to stop me. Though, and I wondered if I was imagining this, I thought I heard her gasp. Albeit almost imperceptibly. I also wondered if it were my imagination, but she seemed to lean a little closer to me.
After what seemed like several minutes, but was probably no more than 30 seconds, my nerve failed me. And I, albeit reluctantly, pulled my hand away.
I’d said nothing so far. In fact I was, initially, incapable of speech. My mouth was dry and my heart was pumping. I turned and prepared to race to my room in shock and embarrassment. But, looking back at Sally, I finally found my voice. Stuttering out, in an unbelievably gauche way.
“Thank you Sally, that was lovely,” blushing furiously as I said this. And cringing at how awful it sounded, as soon as the words left my mouth.
“That’s OK,” she replied quietly, as I turned and fled.
Closing the door firmly behind me in my room I was a maelstrom of emotions: worry that I’d completely over-stepped the mark and violated my sister; concern that she’d tell our parents and I’d be in huge trouble; embarrassment that I’d behaved so clumsily and naively; but also arousal, that I’d got to feel/grope such a gorgeous arse; and finally optimism, from Sally’s reply (and her manner), that it might just be possible, and possibly even welcomed, for me to repeat the act.
That night at dinner conversation between us was stilted. But I don’t think our parents noticed, as were often subdued. We’d have occasional debates about all manner of things. But could, just as often, be introspective and reserved.
As soon as my light was off in bed, later that evening, my hand was on my cock. And I was masturbating furiously. Fantasising that I’d pulled Sally’s tracksuit and knickers down and fucked over the sink! I was so turned on I brought myself off twice, in very quick succession, before I was able to sleep.
A day later, it seemed likely that Sally wasn’t about to report me for “sexual assault” to our parents. In fact, if anything, after some initial awkwardness, she seemed warmer towards me. In, of course, her own reserved way. So I determined to see if I had the nerve to repeat the act.
At the weekend, when our parents were out shopping, Sally came and stood beside, whilst I was sat at the dining table, doing some schoolwork.
I was doing Maths homework. And, as she leaned down to check on some of my calculations, I took the opportunity, once again, to reach back and stroke her arse.
Once again, she did nothing to stop me. After initially flinching at the contact, this time I could definitely feel her “pushing back” against my hand. As well as leaning just a little closer towards me.
Emboldened by this, I finally found the courage to break my silence.
“God Sally, you’ve got a gorgeous bum,” I managed to croak.
“Thank you,” she almost whispered in response.
Looking back (and having checked this with Sally retrospectively) I could and should have gone further. But, once again, my courage failed me.
Over the next few weeks, with my confidence increasingly bolstered by the lack of any reproach, whenever we were alone in the house together I engineered a reason to stand close to Sally. And, whenever I did, I took the opportunity to fondle her arse. Initially I’d be caressing the cheeks, over her clothing. But, becoming gradually bolder, I started to fondle the gusset of her trousers. Then, becoming bolder still, I’d reach under her trousers and caress bare skin. Though I was still not confident enough to feel her pussy directly.
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One of my prized possessions at the time was a porn mag that a friend in school had gifted me. He’d pinched it from his Dad’s collection. It was soft core and, compared to what’s now available online, really tame. But the tits and pussies on display (as well as the stories) kept me in “wanking fodder” for months on end.
One afternoon, prior to settling down to do some schoolwork, I’d retired to my room to masturbate as I poured over the centrefolds. Our parents were in work. And I knew Sally had a late revision session. So I’d have the house to myself.
I was laying there, masturbating vigorously, when I noticed, out of the corner of my eye that the door (which has been ajar) was now wide open. And Sally was standing there, open mouthed with horror, at the scene before her.
“Oh my God Jack, I’m so sorry,” Sally stammered in apology. “I saw the door open and heard you in here. But I should have knocked. I just came to see if you wanted a cup of tea…I can see you probably don’t,” she concluded with a shy smile.
I’d pulled a pillow onto my lap. But I was still laying there, completely naked. With Sally, seemingly, not in any rush to leave the room.
“Oh my God, I’m mortified,” I reported, beet red with shame. “You won’t tell Mum and Dad will you?” I pleaded.
“Of course not,” she responded. “I’d be too embarrassed to bring it up. And I’m sure they’d be too embarrassed to hear of it.”
“But anyway,” she continued, “it’s none of their business. And it’s not like you’re doing anything wrong, or out of the ordinary.”
My shoulders, in fact my whole body, relaxed as she said this. I really had been concerned about the potential repercussions. And I realised I’d been tensing up, almost rigid with fear and self-consciousness. Though my erection had certainly shriveled away to nothing!
So though I’d stopped worrying, I was still mortally embarrassed. But I began to process a little of what Sally had said. Particularly about this not being, “out of the ordinary.” Did she just mean that she knew all boys did this? Or was she suggesting this was something she did herself? An idea that really intrigued me.
“Anyway,” Sally continued. “I really am sorry I’ve disturbed you. I’ll let you carry on,” she suggested. Blushing again as she said this, as she shuffled towards the door.
As she reached the door, she paused, with one hand on the handle. Taking a deep breath, she looked back at me and asked, so quietly that I could barely hear her, “actually Jack, would it be OK if I stayed and watched?”
“What?” I spluttered, “did I hear you right? You want to watch me play with myself?”
She wouldn’t look me in the eye. But, staring at the floor, she confirmed that I’d heard her correctly.
“Yes, that’s right.” Sally agreed. “I know it’s a strange request. But I’d love to watch you masturbating…And then see you make yourself come.” she concluded timidly.
My dick, which had shrunk to a fraction of it’s previous size now began to swell up again. Obviously over the last few weeks our relationship had started to become “sexualised”. In that I’d been groping Sally and telling her how sexy she was. But this, clearly, was taking it up several notches.
I was so taken aback, I really didn’t know how to answer. My first instinct was to deny her request and tell her how daft an idea it was. Looking back, if I’d have done that we may never have gone on to do what we subsequently did.
But I was genuinely aroused at the idea of Sally watching me. And cognisant that it signaled a significant step forward in our relationship. Or certainly significant to me, considering how little interaction I’d ever had with any other woman.
My dick, as is so often the way, overcome my brain.
“Ok…” I answered slowly, “if you’re sure you’d really like to do that. I don’t want to do anything to offend you.”
So, taking a deep breath, I removed the pillow from my lap and lay there, completely naked. With my dick now more than half hard.
“Oh my God, that’s bigger than I imagined,” Sally remarked.
Which was kind of her. But, having been in enough changing room showers, I knew I was no more than average sized. But it certainly did my confidence a lot of good.
Emboldened by her apparent approval, I started gently tugging on my cock. Which, after just a few strokes, reached full erection.
“Wow,” Sally exclaimed, with a giggle, “that didn’t take long. That looks really hard now. Almost painful.”
“No, it’s not too painful. Though it can be when I’m really desperate. But, right now, it feels really good,” I grunted in response.
I gave myself another few gentle gentle stokes, then shocked myself, by how forward I was, with my next suggestion.
“This isn’t fair,” I opined. “I’m lying here completely nude, with my genitals on full display. And you’re fully clothed.”
“Genitals,” Sally laughed, “I’m sure that’s not how you normally refer to them.”
“Ok,” I agreed, with a grin. Amazed at how open we were being with each other. And how comfortable we appeared to be.
“What I meant to say is, I’m playing with my cock. But, whatever I call it, it doesn’t address the clothing imbalance.”
“So are you suggesting I get undressed too?” Sally asked shyly.
Chickening out a little, I back tracked slightly.
“Well, not necessarily undressed.” I fed back, “but you should at least take your top off.”
“Oh, so you want to see my boobs? Or my tits, if we’re using “industrial” language.” Sally responded, with a grin.
Without giving me any time to reply, she pulled her jumper over her head and swiftly unbuttoned her school blouse. Pausing briefly, but still giving me no time to respond, she flung off her blouse before reaching behind her to unclip her bra.
My heart stood still as she held the cups of her bra in her hands. I realised that I was about to see my first ever, real-life, tits. And they belonged, quite remarkably, to my step-sister.
Dropping her hands, she let those tits swing free. And what tits they were! In fact, “swinging” is unfair. They were, despite their size, so firm they barely moved at all. Large (I subsequently discovered she was a D cup), but not out of proportion to her body. And completed with stubby, dark brown nipples, surrounded by large, equally dark, areola.
I thought then that they were close to perfect. But, clearly, I had none, outside of a porn mag, to compare them to. But, in my gauche, clumsy, way, I told her what I thought of them.
“Oh my God, Sally, I’ve never seen boobs that nice. Not even in a magazine.”
“Thank you very much,” she replied, quietly. “I’m really glad you like them.”
Then, aware that I’d already exhausted my sexual conversational skills, I concentrated on my cock. Or, to be more accurate, I concentrated on wanking my cock, whilst staring hard at Sally’s tits. In fact I was determined to imprint the vision on my brain. Jut in case I never saw them again.
Realising where my gaze lay, Sally queried this.
“Don’t you normally look at the girls in that magazine?”
“I do,” I grunted in reply, as I continued rubbing my hard cock. “But, if you don’t mind, I’d much rather look at you. Is that OK?”
“I don’t mind,” Sally assured me, so quietly now she was almost inaudible. “But I’m feeling really shy and I’ve got a funny feeling in my stomach. It’s probably just nerves.”
“Ok, thank you. As long as you’re OK with that. I’ve never seen anyone’s boobs before in real life,” I confessed. “But yours really are wonderful,” I managed to stutter.
“Thank you again,” Sally replied. “It makes me feel really funny when you compliment me like that.” Then, after a long pause, “are they really that good?” she queried, hesitantly.
“Oh God yes,” I confirmed, through gritted teeth now, as I tried to delay my impending orgasm. “I can’t imagine how they could be any better.”
Despite her inexperience, Sally could see, from the way I was tensing and the increase in my breathing, that I was now close to orgasm. In the same way that my eyes never left her tits, hers were fixed on my cock.
“Come on Jack,” she encouraged me softly. “It looks like you are ready to come. Let me see your semen shoot out.”
This gentle suggestion was all I needed to trigger my orgasm.
“Nnngh, nnnghh, here it comes, YESSSSSSSSSSSS…” I hissed.
With my eyes still transfixed on Sally’s heaving hits, my buttocks clenched, my back arched and several ropes of spunk fired from my cock. The first few of these were so powerful that they reached high up on to my chest.
“Oh my God,” Sally shrieked, “I wasn’t expecting there to be so much, or for it to shoot out so far.”
Laying back on the bed, quite literally spent, I looked up with, what I suspected, was a huge grin on my face.
“Actually,” I confessed, that was more than usual. In fact that was almost certainly the most powerful climax I’ve ever experienced.”
“Do you think that was because of me?” she wondered, blushing as she asked.
“God yes, of course,” I spluttered in reply, “that’s the most exciting thing, sexually, that’s ever happened to me… so far at least,” I concluded, with a shy smile.
“Well, I’m very pleased to hear that,” she responded, with her chest (still wonderfully on display) almost visibly puffing at the complement. “It was pretty exciting to watch too,” she confessed. “I’m so glad you let me.”
Bu then I think the enormity of what we’d just experienced started to sink in. So we rushed to get dressed, in an awkward silence.
But, as she was in the doorway, about to leave, Sally looked back. “Do you mind if I ask, but how often do you that?” she inquired shyly.
“Well, most days, I would imagine.” Then, determined to be honest, after what we’d just shared, I continued. “Actually everyday, sometimes more than once a day.”
“Crikey, I thought that might be the case. I’d heard boys liked playing with themselves. But I wasn’t sure.”
After a brief pause, Sally shocked me further. “Would it be OK if I watched you when you do this again?” Once more, blushing furiously. But, this time, she was at least able to maintain eye contact.
Expanding on her thoughts she explained, “I want to get a good sense of what boys like to do to themselves. So that, when I get a chance to do it myself, I’ll have some idea.”
“OK,” I laughed, “so you’d be viewing this as some form of tutorial?”
My confidence had been bolstered enormously by the clear delight Sally had taken in watching me masturbate. And, unless I was mistaken, the appreciation she had for my cock. Plus the interest she had in learning more about the functionality of male genitals (or cock as we were now calling it). And, seemingly, mine in particular. Even if, I guess, a large part of the appeal was the fact I was “on site”, available and as desperately inexperienced as she was.
Over the last few weeks I’d been viewing Sally, very much, as a sexually desirable young woman. In the last half hour or so, it struck me that she was probably viewing me in a similar light.
In a demonstration of this growing confidence and comfort with the situation I made another suggestion.
“Actually, if you want to get some practice in, on a real life male, you’ve only got to ask.”
Sally coloured up again, before answering, “that’s a kind offer. But I think, for now, I’ll just sit and watch.”
I liked the sound of the “for now” part. But I didn’t push my luck. Instead, I made a suggestion to repeat this the following day.
“I often have a wank after school,” I informed Sally. “If we are both back early tomorrow, before our parents get back from work, why don’t we do this again then?”
“Ok,” she agreed readily, “it’s a date.” Then, continuing sadly, “actually, that’s as close to a date as I’ve ever got.”
“Hey,” I responded, “don’t feel bad. That would be exactly the same for me too. But, look on the bright side – for me anyway – that’s a date where at least one of us is guaranteed to get off.”
Punching me on the arm, an act that I found strangely intimate, Sally grimaced, “fine for you, I guess.”
“Look,” I insisted, “there’s nothing to stop you joining me in playing with yourself.” A suggestion that, as soon as I’d said it, made me cringe with embarrassment. But was another illustration of my rapidly burgeoning confidence.
Sally’s reply once again took me a little by surprise.
“Actually, perhaps I will do that one day,” before it was her turn to lose confidence and rush out of the room in embarrassment.
That evening at dinner we were both, once again, uncomfortably quiet. But, as before, this either passed unnoticed, or certainly not commented upon, by our parents.
That evening in bed I reflected, with astonishment, on the seismic change in our relationship. But also looked forward to what I hoped would be further sexual developments between us. As difficult as it was, I refrained from masturbating again. I’d seen the pleasure Sally seemed to take in the amount I ejaculated. And I knew that an evening of abstinence would make tomorrow’s climax that little more powerful.
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I raced home from school the next day and was delighted to see that Sally was already home. As excited as I’d been all day I was now, once more, struck with nerves and crippled with shyness. But the thought of seeing her tits again gave me a considerable incentive to overcome this.
Seeing Sally in the kitchen, as I dropped my school bag, I sensed that she was similarly afflicted. But I summoned up my courage and made a quiet suggestion.
“Do you fancy going upstairs again?” I managed to croak.
“Oh, yes please, I’d like that,” she responded encouragingly.
So off we trooped, back to my bedroom. Closing the door behind us I looked Sally in the eye and swiftly, before I lost my nerve, stripped off. Nervous as I was I was still flaccid. But that changed as, following my lead, Sally quickly peeled her jumper off, unbuttoned her blouse and unleashed her tits. As soon as I saw them again my dick reared in front of me, going from limp to fully erect in seconds.
“Oh my goodness,” Sally laughed, “that thing has a life of its own. was that because you saw my boobs again?” she asked shyly.
“It certainly was,” I agreed, “as I told you yesterday, they are just perfect.”
With this compliment, entirely justified as it was, causing Sally to blush furiously.
“That means a lot to me,” she answered in a whisper. “No-one has ever said nice things about the way I look. It makes me feel really funny when you say things like that.
“Mind you,” she smiled, “its only my tits you like. And by the way, I’m going to call them tits, not boobs. Even using language like that makes me feel funny. Anyway, as I said, you’re only focusing on my tits, not the rest of me,” she concluded, with a mock pout.
“Ok, that’s a fair point,” I conceded. “I would agree that I really love your tits. Partly because I’ve never seen any real life ones before. But, as I just said, they are perfect. But I also think, especially when you smile, as you just did, you are really, really, pretty. Your skin is flawless, you’ve got fine delicate features and a bone structure that any woman would die for.”
To this day, I’ve got no idea where this eloquence came from. Possibly the comfort I felt with Sally? I’d certainly never paid any woman compliments like that before. I’d have been too embarrassed, plus fearful of rebuttal or disdain. But with Sally I felt able to express my feelings. And confident they would be well received. In that regard, I was right!
In a display of emotion and physicality I was not expecting (but was hugely welcome) she flung herself at me and held me very very tightly.
“Oh Jack,” she almost sobbed, “that is so sweet. As I just said, no-one has ever said anything as remotely as nice as that to me.”
This embrace was taking place with me stark naked, Sally topless and my erection pressed, almost painfully, between us.
As realisation of this hit, both of us coloured up with embarrassment. But, tellingly, neither of us made any effort to pull apart. Though, sadly, at that stage, neither of us made a move to move things up a level either. Much as we probably both wanted to. But I did have enough confidence to make another suggestion.
“Anyway,” I countered, still holding Sally close, “your original comment is not fair. You’ve seen my cock. But I haven’t seen the rest of you. I think you should strip fully today whilst you watch me wanking.” I smirked.
“Ok,” she answered, after a brief pause and with a nervous croak in her voice. “I think that seems reasonable. If I’m going to see you in all your glory then you should see me. Would you like that?”
“Oh my God yes,” I assured her, letting go of her and lying back on the bed so I could watch her disrobe.
“Actually, before I start,” Sally disclosed, “let me be honest with you. I was being coy, if not childish, when I said I feel “funny”. I can see your arousal,” she laughed, looking at my twitching dick, “but that’s what I feel too. I’m turned on by what we are doing.”
The eloquence of a few moments ago had deserted me. Not trusting myself to speak, but hugely excited by this disclosure, I just nodded, but with a huge grin on my face.
Watching intently I saw Sally, just feet away from me, shrug off her school trousers, followed, after a slight pause, by her knickers. This wasn’t a provocative striptease. But that vision remains indelibly printed on my mind. The first ever completely nude woman that I saw.
And what a woman. I’d admired her body in a swimming costume at a gala. I’d felt it over her clothes over the last few weeks. And, as of yesterday, I’d seen her tits. But now I could admire her, in all her splendour.
I said above that I thought her tits were prefect. But actually, all of her was perfect. She had toned, muscular legs, a flat stomach, with the hint of a 6 pack. And, as she turned round to drop her clothes in the corner, a tight, symmetrical, bum. For the last several weeks I’d been groping her bum. But I could see now that it looked as good as it felt.
“Oh my God Sally,” I managed to croak. “You look absolutely sensational. I can’t believe how good a figure you have.”
“Thank you,” she answered quietly, “you’re in pretty good shape yourself too.”
Bolstered by this compliment, my cock twitched and, laying back on the bed, I very gently started stroking it. Sally took up position opposite me, at the foot of bed. In a display of confidence herself, she sat upright, but with her legs apart. So I had a decent view of her pussy.
This pussy, unsurprisingly given her generally hirsute nature, was very hairy. But so, at that time, were almost all of those women that I’d seen in the porn mags that I’d got my hands on.
My eyes never left her. But I was torn between focusing on her tits or her pussy. But also looking up at, what I was increasingly realising, was her extremely pretty face. Though her delicate features were now contorted in rapt concentration herself.
“I really like watching you wanking,” Sally informed me. “Seeing how turned on you are makes me turned on to. I loved it when you spurted everywhere yesterday. And I’m really looking forward to seeing you shoot again.”
“Oh shit,” I gasped, “hearing you say that is likely to make that happen sooner, not later. But I’ll try to hang on. I don’t want to come just yet.”
So, without shifting my gaze from Sally I tried to think of calculus and algebra to distract me, grimacing in concentration. But Sally, with a mischievous smile, was teasing me, albeit verbally, not physically.
“Oh my God Jack, those balls look fit to burst. And the head of your cock is purple and bulging. I reckon you’re going to go off like a rocket.”
I’d stopped my wanking to a snail’s pace, fearful of exploding too soon. So turned on was I that I knew the slightest touch could see me orgasm. But, taking a deep breath and contracting my pelvic muscles I was able to delay it, at least momentarily. And I was able to continue wanking, albeit quite gingerly.
“Tell me how it feels,” Sally directed.
“It feel absolutely wonderful,” I croaked. “I’ve always enjoyed the pleasure I can give myself. But to do it in front of you, whilst feasting, visually, on your magnificent body is making me more excited than I’ve ever been (clearly my sexual eloquence had returned). But I can feel my orgasm building already, my balls are fit to burst.”
“Come on then Jack, give in to it again,” she encouraged, “let me see that spunk fly like it did yesterday.”
That encouragement was all it took for me to do exactly that.
“Oooh, ooohhhh, OoooHHHHHHHHHHH…” I shuddered and gasped as a torrent of spunk spewed from my pulsing cock. The first shot, this time, going even further than yesterday and almost reaching my throat.
“Oh my goodness,” Sally shrieked, that seemed like an even bigger load than yesterday. And it flew even further.”
“I think it was,” I agreed, with a sigh, “I didn’t think I would be more excited than I was when I first saw your tits. But to see your pussy and to hear your urging me on – as well as verbalising my own arousal to you – really got me worked up.”
Looking up I could see, even with my inexperience, that Sally seemed flushed and excited herself. Her large nipples were erect, her chest was heaving and she seemed more than a little flustered.
“I’m clearly not an expert in these matters,” I joked, “but it looks like I’m not the only one who is worked up?” Amazing myself at how comfortable I felt in discussing our arousal so openly like this.
“Guilty as charged,” Sally agreed with a blush. “I told you a little earlier how much this was turning me on. And watching you orgasm like that, especially knowing that I’ve been a part of your excitement, is a huge thrill.”
Once again, surprising myself with how forward I was being, I made a suggestion.
“Why don’t you do something about that?” I proposed. “You’ve seen me play with myself. I’d love to watch you do the same… But only if you’re OK with that,” I concluded a little lamely, finally losing my nerve and not wanting to appear too emphatic.
Fortunately, despite my lack of conviction, Sally was clearly turned on enough to agree to my suggestion. Though not without a degree of reticence.
“Oh God Jack, I’d love that, on two grounds. Firstly, I really am worked up. In fact, I’m desperate for relief myself. And secondly, I think it would be a huge turn on for you to watch me, as I’ve watched you. But all of that said, I’m really shy. I’m not sure if I’ll be able to relax enough to get off.”
“Look,” I suggested, “why don’t you just start off by gently playing with yourself. And see how you feel after a few minutes?”
Then, in another display of my new found comfort and confidence I looked her in the eye and made a follow-up proposal. “Though, of course, I’m happy to help if you’d like.”
“Mmm, I’m sure you would,” Sally chuckled, “but I think I probably will be fine on my own. But maybe in the future…” she suggested, with a glint in her eye, causing my cock to twitch back into life at the idea.
Still at the foot of my bed, Sally laid on her back, facing me, as I remained in position propped up against the back wall, just feet away from her pussy. Despite the foliage that Sally had around her pussy I could see a degree of moisture. In fact, as she spread her legs provocatively, it was more than a degree. She appeared to be soaking wet!
Confirmation of this was given as following my suggestion she began, very tentatively, to play with herself. I could see immediately and even with my inexperience, that she was extremely well lubricated. In fact, I couldn’t just see it, I could almost hear it!
I realised I had no clear idea how women masturbated. And in later years I discovered that, unlike men, there are more variations to this particular theme.
Sally’s technique was to initially play with her pussy lips with one hand, whilst inserting a single digit into her pussy.
“Oh shit yes,” she gasped, as she inserted that digit, with her eyes hooded, but still never leaving my gaze.
Despite having come just 10 minutes earlier this masturbatory vision, directly in front of me, had my cock at full mast once more. I was gently rubbing it. But didn’t say anything for fear of breaking the spell and causing Sally to stop. I probably needn’t have worried.
“Jesus Jack, this is so horny to masturbate in front of you,” Sally whispered. “Especially as I can see it’s turned you again. Keep wanking yourself,” she directed. “And come nearer, I want you to experience it really close up.”
So, I shuffled down the bed and lay next to Sally, on my side, with my dick almost touching her hip. If I’d had the confidence I could have reached out and fondled Sally (and much later she confessed that’s what she’d been hoping I would have done). A large part of me was aching to do just that: feel those wonderful breasts; suckle on a stubby, prominent, nipple; or establish how wet and velvety her aroused pussy felt. But I was much too diffident to push my luck any further than I already had. So I contented myself with watching Sally as I, for the second time that afternoon, started to bring myself closer to orgasm.
As she upped her pace, I did exactly the same. But our eyes were always focused entirely on the other. Or, to be accurate, on each others body’s, not faces. I was transfixed at the scene in front of me, which was not something, just a few weeks ago, I’d ever have envisioned seeing.
Sally continued to finger her pussy, quite gently, but was now frigging her clit more rapidly. Her breathing was coming in short gasps and, painfully inexperienced as I was, I could sense from knowledge of my own arousal, that her own orgasm may be approaching.
Moments later that sense was confirmed. Grasping a full breast, Sally’s fingering of her clit became even more insistent and her climax hit.
“Nnngh, nnngh, ,nggghh, YESSSSSSSSSSS…” she cried, throwing her head back and shaking with the power of it.
The sight (and sound) of which triggered my own orgasm, which, to my mortal embarrassment, I fired over Sally’s lower abdomen!
“Oh my God Sally, I’m so, so, sorry, I didn’t mean to do that,” I spluttered, in profuse apology. “That’s inexcusable, let me get a tissue.”
“Wow,” she squealed, but in something much more closely resembling pleasure than revulsion.
“Don’t worry,” she laughed, easing my embarrassment somewhat, “that’s fine. I just had no idea it would be almost hot like that. Actually both in temperature and emotionally,” she giggled. “Or that there would still be that much second time around.” She then shocked me further by playing tentatively with it as it pooled near her navel.
“I really am sorry,” I proffered once more. “It’s just that it was so horny. I couldn’t contain myself. I’m so glad you let me watch you.” I enthused.
“Are you kidding,” she responded. “that was such a rush to have you watching me. It made my orgasm bigger than ever. And I really don’t mind that you showered me in your spunk,” she grinned again. “It was really sexy in fact.”
Rousing ourselves we started to clean up and get dressed, much less sheepish and embarrassed than we’d been the previous evening. As Sally was about to leave my room she looked back with a questioning glance.
“Can we do this again? Quite soon?” she asked hesitantly.
“God yes, of course.” I agreed immediately. Then, playing back to Sally a question that she’d previously asked me, “how often do you masturbate?”
“Similar to you” she smiled, shyly, “I do it pretty much every day. I get a bit cranky if I don’t,” she disclosed. “I hope that doesn’t make me sound like a sex fiend?”
“Wow,” I laughed, “I don’t think it makes you any more of a sex fiend than I am. Though I’m not sure I was expecting that reply. I was pretty sure girls did it. And I guessed you’d be no different. But, I’m not really sure why, I just didn’t think it would be with the same frequency as us guys. So would it make sense that we should try and do this every day?” I queried.
“I think that’s an excellent idea,” Sally agreed, with a shy smile.
So, for the next few days, whenever we could find an opportunity, we followed a similar pattern. Masturbating together as we admired each others bodies. With Sally increasingly keen for me to spunk over her. Not that this drew any complaints from me.
Somewhat irrationally, now that we were spending time alone and nude together I wasn’t “feeling Sally up”, as I had been previously, albeit over (and occasionally under) her clothing. Both of us, I’m sure, felt wary of pushing too far, too soon and breaking the spell. But that changed at the weekend, about a week after we’d starting masturbating together.
Our parents, somewhat unusually, had gone out for dinner with friends. Leaving the two of us alone for several hours. Sadly, but unsurprisingly, neither of us had any plans with friends of our own. But, at this stage, we were both delighted to have at least some uninterrupted time with each other.
They’d made us dinner just before they left which we hastily bolted down. As we cleared the dishes away Sally, in an act similar to the one that had first started our sexual journey, was leaning over the kitchen sink. I moved behind her, as I had on that first evening, and began fondling her fantastically athletic buttocks. This time I was not fearful of an adverse reaction. But neither was I expecting Sally to respond as she did.
After initially leaning back into me to allow me to grope her more freely, she reached behind me, grasped my hands and pulled them in front of her. She placed both of them onto her breasts. For a few seconds I froze as I realised that this, clearly, was the green light for me to take things further. So taking advantage of this I began, in my customarily clumsy fashion, to fondle Sally. As I did this I was pressed very firmly against her, with my rock hard cock grinding against her tight arse.
Reaching under her tee shirt I ran my hand up her well defined abs and reached up to feel her breasts for the first time (indeed the first time of course that I’d felt any breasts). She had on a flimsy bra, so I could already feel her nipples through it. Taking my courage in both hands, I reached in and lowered the cups so that I could access her tits fully.
“Oh shit, yes,” Sally hissed, as I manipulated her nipples.
Emboldened by her response and the obvious approval of my actions I took another more daring step and dropped one hand into the waistband of her leggings. Then, before I lost my nerve, I moved lower and reached into her knickers.
My mouth was dry and my heart was beating so hard I honestly wondered if Sally would be able to hear it. But she certainly did nothing to stop me. In fact, far from it, as she was now pushing firmly back against me and breathing heavily herself.
I took the final step and lowered my hand just an inch further until, for the first time in my life, I had my hand on – and then fingers in – a pussy.
As exciting as this was for me, it seemed to be having the same effect on Sally. As my trembling fingers made their way through the mass of hair I’d encountered she was gasping and writhing against me.
I really did have very little idea what I was doing, particularly as I was behind Sally and was working purely on touch. Fortunately, Sally was so aroused and therefore so wet that my fingers were running smoothly over her pussy lips and then into her pussy itself, causing her to groan and finally turn towards me.
“Oh God, Jack, you’re driving me wild… plus,” she then confessed, “I’ve been playing with myself a little earlier, in anticipation of having this time together. So I’m absolutely on fire. Shall we go up to my room so we can be more comfortable and take this further.”
“God, yes please,” I concurred.
So we raced up the stairs and, in record time, shed our clothing. After a brief pause, we collapsed onto the bed, as I pulled Sally to me. As we did this, in the latest in a series of “firsts” she grabbed my cock. I was so worked up I almost came at that very first touch. And I certainly twitched and winced involuntarily.
“Is that OK,” she asked, with some concern.
“Oh my God yes,” I assured her. “it’s much better than OK. I was just worried I was going to “pop” before we even started. You’re not the only one that’s one fire.”
But, with the shock of this initial contact over, I was more able to relax and enjoy the experience. Laying on the bed, both of us stark naked, we continued to explore each others bodies. Sally had her hand wrapped around my cock, with my fingers buried in her pussy.
As we were lying there side by side, just inches apart, masturbating each other I looked over at Sally. Her lips were parted and we looked deep into each others eyes. We were so close I could feel her breathing and, in an act that felt both entirely natural and utterly terrifying, I leaned over and kissed her.
Oh my God, it was electric! But after a few seconds I paused, worried that I’d perhaps overstepped the mark.
“Are you sure this is OK,” I queried. I really was a respectful (perhaps overly so) lover.
Seemingly not trusting herself to speak, Sally just nodded assent and pulled me back to her.
I discovered, almost immediately, that I enjoyed kissing almost as much as I was enjoying being wanked off. So, it appeared, did Sally.
So much so that we let go of our genitals, wrapped our arms around each other and buried our tongues in each others throats.
Remarkably, at the age of 18, until then I’d never kissed a girl. Nor, I discovered later, had Sally kissed a boy. There can’t be many people who’ve been wanking with another person before they’ve been kissed! So, from the off, we made up for lost time.
As gratifying as this was, of all the things we’d done (and were to do in the future) this felt, initially at least, the most awkward. Watching ourselves wanking, and even wanking each other, felt somehow “functional”. Whilst kissing, on the other hand, had much more of an intimacy about it. That, of course, is part of its huge appeal. But kissing your sister, or to be accurate step-sister, felt much more taboo.
But that awkwardness very rapidly passed. And the taboo element, I’m sure, added further to the excitement. As with everything we were doing we were unskilled in the art of kissing. But, what we lacked in skill, we more than made up for in enthusiasm.
So we lay there on the bed, swirling our tongues against each other and into each others mouths. Initially with an urgency and force that, whilst understandable, was probably a little much. But we both, almost instinctively, found we derived more pleasure as our kissing became more sensual and less forceful.
So in that first frenzied 10-15 minutes we were like kids in a sweet shop. I wanted to devour Sally with kisses, but also suck on her tits, whilst simultaneously frigging her. And she was doing the same to me (minus the tit sucking). We really didn’t know what to do to each other and for each other.
But our hunger for each other soon manifested itself in a need to seek relief. And I was a little embarrassed that I was the first to “crack.” Or, to be more accurate, spurt! With Sally’s tongue buried deep in my throat, my fingers in her pussy and her hand wanking me, inexpertly but furiously, I felt my orgasm building.
“Oh God, I’m really close now, I don’t think I can hold off,” I panted, as I paused from our kissing to warn her.
“Come on then Jack, come for me,” Sally encouraged, pushing me onto my back and hovering above me. The sight of her stupendous tits swaying above me as she pumped my cock was all that it took to trigger my orgasm.
“Oh, oh, oh, oh, oooohhhh, shit, YESSSSSSSSSSSS!!” I grunted, as several ropes of spunk shot from my cock. The first of which was, once again, so powerful it shot upwards and landed on Sally’s tits. It was, up to that point, the most powerful orgasm I’d ever experienced.
“Oh wow,” Sally exclaimed with a deep, throaty, chuckle. “You often seen to produce a lot of spunk. But that was huge. How is there so much?”
And she then shocked me further. After rubbing it into her tits she put a little on the tip of her finger and lifted it to her lips.
“Well, I laughed,” collapsing back onto the bed. “that’s the first orgasm that some one or thing, other than my own hand, has caused. Add in how gorgeous you looked, plus the time we’ve just spent exploring each others bodies and I’ve never been so excited. Though seeing you taste my spunk like that runs it a very close second,” I joked.
“Oh my God,” Sally exclaimed, as she came down and gave me a huge hug and kiss. “That’s such a turn on for me to know that I’ve been able to arouse you like that. I was a little concerned I wouldn’t be any good at wanking.” she smiled.
“Good?” I laughed, “you were fantastic. I hope you’ll do that to me loads more.”
“Too right I will,” she agreed readily. But then made me aware that I was not the only one who’d been close to orgasm.
“I’m sorry, Jack,” Sally exclaimed. “That’s got me so excited. I’m absolutely desperate too. Do you reckon you’ll be able to bring me off?”
“I’ll do my best,” I nodded in response. “But I’m not really sure what to do.”
“Don’t worry, what you’ve been doing so far is perfect,” she assured me, “just copy what you’ve seen me do to myself,” she directed, “keep on gently fingering my pussy and rub my clit. But not too hard. I’m so close it won’t take you long.”
So, letting go of my cock, Sally laid back on the bed and I concentrated all my efforts on doing just that. Initially I nibbled gently on her tits (partly, if I’m honest, for my benefit as much as hers) whilst I fingered her pussy trying to recall, as she’d suggested, what I’d seen her do herself.
I knew that she was generally quite considered and gentle in how she frigged herself. Only moving rapidly right at the end, as her climax was imminent. So that’s the approach I determined to replicate. And it seemed to work.
“Oh God, Jack, that’s so good. Just keep doing what you’re doing,” she encouraged, with a throaty growl. “But hook your fingers up slightly so they are against the front wall of my pussy.”
This latest directive certainly seemed to have the desired effect. I could see goosebumps all over her, her breathing was shortening and she was writhing against the bed. By monitoring her reactions I was already working out the right places to apply pressure and the correct amount of pressure to exert.
“Kiss me again Jack,” she exhorted, pulling me down towards her.
So, whilst continuing to finger her we indulged in some further passionate kissing. With, of course, the faint taste of my own jizz still on her lips. The combination of all this was now definitely taking her arousal to another level.
Breaking from the kiss, Sally confirmed this.
“So close, Jack…” she panted, “just a little harder and a little faster…”
Seconds later, as I followed her instruction, I was rewarded by witnessing her juddering climax.
“Nnnghhhh, nggggh, nnnghhhh, YESSSSSSSS…” she cried out, thrashing around on the bed, grasping the sheets whilst clenching her fists, until eventually pushing me away from her.
As she lay back, catching her breath, Sally looked up with a huge grin.
“Wow, just wow,” was all she said.
“Bloody hell,” I laughed, “I never thought it would be so erotic to give someone else pleasure like that. It was such a turn on.”
“I know,” Sally agreed. “I loved what you’ve just done for me. But I also derived great pleasure myself from giving you pleasure too.”
Plonking myself down on the bed beside her I pulled Sally to me for an all embracing cuddle. A little like the kiss earlier it was an act that was both extremely satisfying, but initially uncomfortable. Signalling, as it did, an intimacy and affection that we’d not previously demonstrated.
We lay there cuddling for several minutes in companionable silence, basking in the afterglow of our first ever orgasms at the hands of another.
Sally was the first to stir, as she lazily began to play again with my flaccid cock. Which, unsurprisingly, began to harden again.
“I’m sure we’ve got at least another hour before our parents come back. And, now that we’ve started, I’d like to carry on our tutorial,” she laughed. “Is that OK?” she inquired shyly, as she continued slowly playing with me.
“Good God, of course it is,” I responded eagerly. “You never ever need to ask me if it’s OK to wank me,” I smiled. “Providing I can do the same to you?”
“To right,” she concurred, with a huge grin.
But then, becoming suddenly serious, Sally propped herself up on an elbow and looked down at me.
“Do you know what Jack, I never imagined we’d doing this. But I’m so glad we are,” she disclosed. “Recently I’ve found my body has been on fire. And I was desperate for someone to interact with. And, as part of that, I was also desperate to explore a man’s body. In fact, let’s be honest,” she chuckled, “I’ve just been desperate.”
But then, turning serious again, she asked, “but are you sure you’re OK with this?”
“I’m absolutely, irrefutably, 100% OK with it,” I assured her. “Even though it seems you’re only doing this with me because of my availability, proximity and most of all your own desperation.” I teased.
“Oi, smart ass,” she responded with a smile, punching me in the arm. “We can draw this to a close any time you choose. Though I’ve yet to see any complaints from you about my availability, proximity or desperation”
“None at all,” I agreed. “In fact,” I continued, also turning serious myself, “this is a situation that suits us both. I’m also desperate to interact with a girl. But I’ve got no confidence at all in how I’d go about achieving that. So, joking aside, our proximity and mutual desperation, is suiting us both.”
“Wonderful, so that’s settled then,” Sally confirmed with a big smile. “We are both getting exactly what we want from this arrangement. Though, of course, no-one needs know about it. So let’s continue where we just left off,” she suggested, drawing me back to her for more kissing and caressing.
So for the next hour we gave full vent to our feelings. We each of us had two more orgasms and took great delight in both giving and receiving pleasure. A theme that was to continue throughout our time together.
And on a similar note, from then on passionate kissing formed a huge part of our sexual repertoire. It was something we did when we were having a full “session”, when we were able to give each other orgasms. But, it was also something we could do in stolen 5 minute segments, as a precursor to more prolonged time together.
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
We continued like this for a few weeks longer. Masturbating each other whilst indulging in hours of passionate french kissing.
We were both really keen to establish what worked for – and turned on – the other. Neither of us had any real egos. So we were as happy to give pleasure as we were to receive it. So, as Sally had suggested at the start of our journey into sexual exploration, we really were treating this as a tutorial, or experiment.
Then, after a few weeks of mutual masturbation, we moved on to another significant milestone.
Sally, as I remarked above, was increasingly keen for me to spunk on her. And appeared fascinated with the texture and consistency of my semen. For my part, I was also intrigued by the viscosity of Sally’s pussy. Plus, I knew how much she enjoyed having her pussy fingered. As well as how much she loved kissing. So it seemed obvious for me to wonder how much she might enjoy having her pussy licked. With, of course, the hope that she might reciprocate and perform oral on me.
So, on one of our more prolonged sessions one weekend, after we’d spent time in general foreplay, I began to kiss my way from her breasts down Sally’s body.
I reigned kisses on her abdomen and navel then, as I continued moving lower, I felt her tense slightly. But I could also sense her breathing shortening. So I felt/hoped it was in arousal and anticipation, not in discomfort.
That was confirmed moments later as she gently grasped my head and moved it lower again, so that I was now level with her pussy. No words were exchanged, but this obviously signified approval for me to perform oral. In fact, as soon as my mouth, hesitantly at first, made contact with her pussy, I could tell how keen she was for me to do this.
“Ooooh yes, oh God jack, that’s so good,” she exclaimed in a husky growl.
As with most of what we’d done together I really had no idea how to proceed. Nowadays, as false as its portrayal of sex is, I would at least have seen cunnilingus performed in online porn. But I had no access to anything like that back then. So, all I really knew was that men “licked pussy.” So that, initially, was what I began doing. Licking Sally’s pussy as though it was an ice cream.
Whilst hopelessly naive, it was I guess, not the worst strategy I could have chosen to follow. Plus, as I’d done with everything else, I was guided by Sally’s responses to my actions. And attuned and interested enough in her arousal to do this.
“Oh, that’s so gorgeous…” she purred, as I gently caressed her prominent outer lips with my tongue. And she gasped again as I took these, oh so gingerly, into my mouth.
I knew from masturbating Sally that she enjoyed the insertion of my fingers into her pussy, alongside frigging of her clitoris. So, as much as I was able to, I replicated that. The difference being that I was using my tongue instead of a finger on her clit. But still using my fingers to fuck her pussy. As inexperienced and untutored as I was, it was working for Sally.
“Oh shit, I love this,” she hissed. “Your tongue feels so good.”
Bolstered by this endorsement of my actions I continued in a very similar vein. Though taking care not to get carried away and be too aggressive in my licking. In fact this reticence was beneficial in two ways. It meant I was not treating Sally’s pussy too roughly. But was also building up her anticipation as she moved towards climax. As I was beginning to realise that a more prolonged build up almost invariably led to bigger and better orgasms.
I was discovering that, as much as Sally enjoyed having her pussy licked, I enjoyed licking pussy. I loved the fact that I was able to experience her arousal (and ultimately orgasm) as close as it was possible to be.
Much as I did when I’d been masturbating Sally I kept on fingering her pussy, whilst attending to her clit with my tongue. I was used now to Sally’s vocal and physical signs of arousal. But it seemed that cunnilingus was taking this to another level.
“Nnnghhhh, nnnghhhhh, oh god, oh god,” she exclaimed, squirming on the bed and grasping my head to pull me tighter against her. Looking up briefly I could see the sinews on the side of her neck were prominent as she tensed in excitement.
Realising that she was close and sensing that she needed me to be more forceful I held her hips tightly and was now lapping a little harder at her clit with the flat of my tongue. After just a minute or two of this I was sure her climax was almost upon her. She was grasping my head so tightly she was pulling my hair and grinding against my tongue with her pussy.
“Oooh, ooooh, oooh, FUCKKKKKKKKK…” she cried, as a huge orgasm ripped through her, causing her to shake and thrash around on the bed.
I held on tightly and did my best to prolong it for as long as I was able to, until she pushed me away.
“Enough…stop!.” was all she was able to say.
Pulling me up Sally was still quivering from the after effects of her orgasm. In fact in later years I seldom, if ever, encountered anyone for whom oral sex drove them quite as wild as it did Sally.
“Oh my God, that was wonderful,” she proclaimed. “I’ve wanted to ask you to do that, but I was worried you’d think it was too dirty. Or that my pussy wasn’t fragrant enough.”
“Well, it probably was a dirty thing to do,” I concurred, with a grin. “But in a really, really, good way. I’ve thought about doing it too, for quite a while. But I wasn’t sure myself how you’d react. And whether you thought it was depraved?”
“And do you think me tasting my own pussy juice on your mouth is also depraved,” Sally asked, as she dragged me to her for a passionate kiss.
“Well,” Sally laughed, as we finally pulled apart. “I actually think my pussy tastes pretty good. And maybe what we’ve done is a little depraved. And certainly my reaction to it was,” she smiled. “But dirty or depraved, it was fucking fantastic. That’s the biggest orgasm I’ve ever had. Can we do that lots more?” she begged, reprising a question I’d asked of her when she’d first masturbated me.
“God yes,” I agreed immediately, “I loved doing it. And yes, your pussy is fragrant. In fact, it tastes divine, to me anyway. It was such a rush to know I could bring you to orgasm like that.”
“Do you know what,” Sally suggested shyly, “I think you’re turning into a pretty good lover.”
Blushing at the compliment, it also caused my dick to rear in front of me. Seeing that, Sally laughed and made a suggestion that I was very much hoping to hear.
“I can see you are still very excited. So I suppose it’s only fair I return the favour. Would you like that?”
“Does that mean you’d like to suck my cock?” I asked, hesitantly. “And if that is what you mean, then oh my God, yes,” I assured her. “But only if you really want to,” I continued with my customary deference.
Looking back this deference and respect was clearly appealing, in some ways. But years later when discussing it with Sally she confirmed that, on occasions, it was too much. And she – and in her opinion most women – would have preferred me to have been more confident and assertive.
“Yes, I am offering to suck your cock. And yes, I do really want to.” Sally confirmed with a shy grin. “Partly because it seems like the charitable thing to do after what you’ve just done for me. But largely because I’ve always wanted to do it. But didn’t want you think I was too brazen by offering it. Though, a little like you, I’m worried that I don’t know what I should do and you won’t really enjoy it.”
“Oh my God,” I assured her, “I’m sure I’ll enjoy it, whatever you do. And if you find your not as good as you’d hoped, I’m quite prepared to be your guinea pig if you feel the need to get lots of practice in.” I concluded cheekily.
“Don’t push your luck, smart ass,” Sally advised with a grin. “Just in case I change my mind. Just lay back and let me get to work.”
Looking up at Sally, with her tits swaying in front of her as she prepared to go down on me I was so aroused that my cock was twitching and I was already leaking pre-cum. That leakage accelerated as Sally, tentatively at first, dipped down and took my cock into her mouth.
Initially, whilst my cock continued to tremor, the rest of me was almost paralyzed with excitement. I lost the power of speech and lay there immobile. Partly incredulous and partly for fear of breaking the spell. I was so rigid – in every sense – that after a few seconds Sally paused and looked up at me.
“Is this OK”, she asked “Are you enjoying it. It seems like you’re barely breathing.”
“God yes,” I reassured her, “it’s wonderful. I’m just so excited I’m frightened to move. Not least in case I come too quickly. But I can’t tell you how good this feels. Even better, much better in fact, than the handjobs you’ve been giving me.”
At this stage Sally had just, hesitantly, taken the head of my cock into her mouth. But, in the same way as we both approached most things sexual, what she lacked in experience or finesse she made up for in enthusiasm. As well as obvious enjoyment in what she was doing.
She was, as I had done moments earlier, trying a variety of tactics to see what worked. It’s fair to say they all did. This included: licking my shaft, both front and back; gently taking my balls into her mouth; and taking as much of my cock into her mouth as she was able to.
I’m making it sound as though this was a prolonged blowjob in which I luxuriated in a variety of carnal delights. The reality was I was unable to enjoy any of these moves for more than a few seconds. Everything new that Sally tried merely resulted in me gasping and groaning. And it was clear to Sally, who now knew my triggers, that I was moving inexorably (and pretty quickly) towards orgasm.
Pausing for a second she looked me square in the eye, with her lips inches from the head of my cock.
“Come on Jack, let it go,” she implored. “I want to taste your spunk,” as she bowed her head back down and took me as deep into her throat as she was able to.
Despite my deference and respectfulness, I needed no second bidding. In fact, I was unable to contain myself. That approval from Sally was all that it took to trigger my orgasm. No sooner had she wrapped her lips back around my cock than I was exploding deep into her throat.
I couldn’t see how much spunk I produced. But I could feel that it was a lot! Evidence of that was that despite swallowing a little of it, an amount – quite a large amount – seeped out of the corner of Sally’s mouth, dribbling back down towards the base of my cock.
Coming up for air and spluttering a little, causing yet more spunk to spill out, I was pleased to see that Sally had a big grin on her face.
“Oh my goodness,” she chuckled, “I shouldn’t have been surprised by the volume and ferocity as I’ve seen you come enough times, but that was pretty powerful. I thought you were going to drown me! Was I any good?” she asked, demurely.
“Good,” I laughed, “well I clearly have no frame of reference, but I can’t imagine how that could be bettered. I think that’s the greatest thing that’s ever happened to me,” I opined. “But I really am sorry there was so much spunk. I hope it wasn’t too unpleasant?”
“Not at all, I was happy to get a mouthful,” she grinned. “And actually, it didn’t taste too bad at all. So come here and get a little flavour of it yourself.” she demanded, pulling me to her for a passionate, open mouthed, kiss.
Considering she’d been happy to taste her own pussy juice a little earlier I didn’t feel I could refuse. Plus I really wasn’t too grossed out at the idea. And, as Sally had suggested, whilst not nectar-like, I certainly didn’t find my own spunk particularly unpalatable.
Sadly, time was against us on this occasion for a second round. But, from then on, oral sex was a firm favourite of ours, which we indulged in at every opportunity.
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Outside of the bedroom, whilst frustrating that we could not publicly express our feelings for each other it was, in some ways, an ideal scenario. We both remained committed to our studies and intent on attending very good Universities. So, when we weren’t actually having sex (or the close approximation to it that were currently enjoying) we were working hard on our schoolwork. And not spending dreamy hours together, whilst neglecting our studies.
In fact I’d struggle, looking back, to explain exactly what our feelings were. Not least because, as an emotionally repressed family, the expressions of any feelings were not something that came naturally to us.
I was certainly fond of Sally. We felt very comfortable in each others company. And I was, of course, enormously grateful for the opportunities we were having to “research” our burgeoning sexuality together. But I don’t think either of us felt we were in love with each other. Or even infatuated. If anything, long before the term became popular, I would say we were fuck buddies. Whatever our status, it was a situation that suited us both.
In fact, one weekend, in a conversation that was as close to opening up to each as we ever got, Sally articulated that.
“Jack, are you OK with what we’re doing together?” she asked with a pensive, almost pained, look.
It was a question we’d asked of each other before. But I was surprised she’d brought it up again, as I thought we’d established we were both now entirely comfortable with our actions.
“I certainly am,” I assured her swiftly. “I’m delighted with what we are doing. What’s not too like?” I suggested with a smile. “But what about you?” I queried. “I’m just wondering why you asked that, as I thought we were both feeling OK about this.”
“No, I really am OK with it,” Sally confirmed. “I’ve got no misgivings at all about the pleasure we are both giving each other. But, clearly, no-one can find out about us. Which is maybe sad. But there is little we can do to change societal norms. But I guess, at the back of mind, I worry you may start blabbing to people about us. My reputation would be in tatters.”
“I don’t know,” I suggested, “it may enhance your reputation for people to see you’ve ensnared the coolest kid in town,” I said with an ironic laugh. ” But who am I going to brag to about my conquest? I’m hardly likely to tell the boys in school, “hey you know my sister, Sally, she’s a really easy lay.” They think I’m weird enough as it is.”
“Oh, so having sex with me makes you weird,” she teased.
“No,” I laughed in return, “if they knew how gorgeous you were they really might think I was the coolest boy in the school. But having sex with my sister, or even step-sister, certainly qualifies as weird in most people’s books.”
“Of course, I understand that,” Sally agreed immediately. “And that’s the point I was making, or was worried about. Rightly or wrongly, our relationship will always have to remain a secret we keep between ourselves.”
“No, I appreciate that,” I replied, seriously. “In fact, I completely agree. It is sad, but I’m happy just focusing on the fun we’re having together. Plus – and I know we joked about this – but I really do think that by treating this like a tutorial we’ve become much better lovers than we would have if we’d been fumbling about with random people from the town. I really am confident that when we do have these experiences with others we’ll be so much better prepared than we would otherwise have been.”
And it transpired that was exactly the case. Though it was some time, when we were both away at University, that we were able to confirm this.
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As much as we were enjoying the mutual masturbation, passionate kissing and now oral sex it was, of course, inevitable that we would want to progress things further. The fact that this took longer than it might have was due to the continued reluctance of either of us to take the initiative. Clearly we both lacked sexual confidence. But were also fearful, I’m sure, of offending the other. Which was, with hindsight, ludicrous given how much we were both enjoying everything we’d done.
But, one Sunday afternoon, when our parents were away visiting relatives (as they did most Sundays) I steeled myself to suggest that we took the next step in our intimacy.
We were naked, laying in Sally’s bed, kissing passionately whilst playing with each other. I’d been thinking, for several weeks, about broaching the subject. And I finally plucked up the courage to suggest it, though with my customary lack of panache.
“Do you think now is the time for us to have a fuck?” I blurted out.
“What, right now? Are you serious?” Sally asked, somewhat incredulously. “I mean that’s not completely unexpected, give what we’ve been doing. But you’ve taken me a little by surprise.”
“Oh God, I’m so sorry” I stammered, blushing profusely, “please forget I ever suggested it,” backtracking furiously, as I was far too prone to doing.
“No, not at all, let’s not dismiss this.” Sally suggested. “I’ll admit it’s something I’ve been thinking about too. So let’s talk about it,” Sally reassured me, with a kindly smile on her face. Plus, I fancied, a degree of excitement in her demeanour.
“Oh, thank you,” I retorted, “I’m sorry I blurted it out like that. I’ve been wanting to bring the subject up for ages. But, and this won’t come as a surprise to you,” I smiled, “but I always lose my nerve. So once I found an ounce of the necessary courage I just fired the question out there.”
“I know, we are as bad as each other,” Sally concurred, “I suspect it’s a combination of our inexperience with the opposite sex. Coupled with the highly unusual situation we find ourselves in. I’m sure you’d be nervous about asking any girl to have sex. But asking your sister to fuck you really is a big deal,” she grinned.
This insightful comment was exactly what we both needed. In fact, looking back, it signalled a watershed in our relationship. Allowing us finally, to confront the bizarre situation we found ourselves in.
“You are so right,” I agreed, bursting out laughing, “those are big issues for anyone to face. Let alone two misfits like us.”
“All of that said,” Sally continued, “I’ve been thinking about it for a while. Clearly, it’s the next logical step. And even nerdy misfits like us can see that. I think I’m very close to taking that step. Even with someone as hopelessly needy as you,” she smiled.
This gentle piss taking, albeit with a very large degree of truth, signified the breaking down of the last emotional barriers between us. Laughing, with no self-consciousness at all, we held each other tightly as we recognised these very apt descriptions of ourselves. That embrace soon morphed into another of our extremely passionate kisses.
We were, of course, completely naked, laying side by side. As our tongues intertwined we were also grinding against each other. My cock, rock hard as ever, was pressed against Sally’s abdomen. And I was grasping her taut butt cheeks to pull her closer towards me.
Changing it up slightly Sally pushed me onto my back and crawled on top of me. Continuing to gyrate against me she was now using her pussy to rub up and down my shaft.
Given how well lubricated she was I knew – in fact we both did – that with just a simple push I could have entered her in an instant. Pausing in her actions, Sally looked deep into my eyes.
“Would you like to be inside me Jack?” she asked softly. “I really think I’m ready to feel your cock in my pussy.”
“Oh my God yes,” I assured her, as my dick twitched between us. “I really, really, want to. But only if you’re sure you’re ready, I’ve got some condoms in my wardrobe.”
“We don’t need them,” Sally responded shyly, “I’m on the pill.”
“What?” I spluttered, “when and why did that happen? Surely you’ve not told your Mum that you were considering becoming sexually active. And certainly not with me,” I continued, in a mild panic.
“Good god no,” Sally hooted with laughter. “She’d have a seizure. Though she does know about me being on the pill. My swimming coach suggested it to her a few years back. I used to to suffer from heavy periods which, with all the training I do, wasn’t ideal. So the GP put me on a particular type of contraceptive pill that helps regulate that. But, of course, it also means I can’t get pregnant!
This discussion had seen my erection subside considerably. But it soon returned with Sally’s next actions and statement.
“The upshot of this is that, if we want to, we can fuck with impunity. And right now, I want to,” she suggested, as she recommenced squirming and gyrating against my cock, still pressed between us and now as hard as it was possible to be.
“I’ll take that as a yes,” she grinned, as I matched her gyrations with my own and was now grinding hard up against her pussy. As she’d done moments earlier, Sally was rubbing her pussy along the shaft of my cock. Pausing on an upstroke she hovered above, looking me directly in the eye, with a searching gaze. The entrance to her pussy was just millimeters from the tip of my cock.
“Are you sure you want to do this Jack?” she asked, so quietly I could barely hear her.
For my part, I was so nervous, I couldn’t speak at all. So I just nodded, holding her hips and easing her, oh so slowly, downwards onto my throbbing cock.
At first, almost exactly as I had been with my first blow job , I lay there rigid and immobile. For largely similar reasons, i.e. because I was fearful that, with the slightest movement, I could come in an instant.
The warmth and tightness of Sally’s pussy was exquisite. Gingerly I started to thrust upwards to meet her downward movements. Actually, thrusting would have been significant overstating my initial movements. Slight tremors might have been a more accurate description.
“Oh my God, this is wonderful,” I managed to stutter, “I can’t tell you how gorgeous it is to be inside you.”
Looking me squarely in the eye, Sally looked down and agreed, “I know,” she grunted, “I feel so full and complete. Now, come on, fuck me properly.”
I attempted to do just that. But, as my first proper thrust brought a gasp from Sally, the whole experience just became too much for me.
“Oh shit, oh shit. NNNNNNNGGHH,” I exclaimed, as I exploded into orgasm, flooding Sally’s pussy with my spunk. So much so that it started to dribble out, down my shaft and pooling on to my lower abdomen.
“Oh my God,” Sally chuckled, though clearly disappointed. “That was quick. You obviously were really excited.”
“I’m so sorry. I was trying so hard to hold back, but that was just too much for me to bear.” I spluttered in apology, with a sheepish look on my face.
“Don’t worry,” she comforted me, still impaled on my dick, which hadn’t shown any real sign of softening. “I’m sure you’ll be good to go again soon. And then you can give me some pleasure.”
“God yes, of course,” I assured her. “In fact, that might be sooner than you think. I’m so worked up I’m still hard.”
“Oh my goodness,” she giggled, “I didn’t imagine it would be that quick. But you’re right, I can still feel your erection,” as she started, once again, to grind her pussy on my cock and against my pubic bone.
In a matter of moments I was rock hard again. But this time I felt in no danger of exploding too quickly. So I was able to lay back and luxuriate in the feeling of Sally’s tight, velvety, pussy contracting around my cock. And, just as importantly, Sally could enjoy it herself, without either of us fearing that proceedings would draw to a close prematurely.
Clearly, neither of us had any experience and I guess we were a little clumsy in our manouvering at first. But the actions came naturally to us. With Sally bouncing around on my cock, as I flexed upwards to meet her downwards pressure with upward thrusts.
“Jesus Jack, this is sooooo good,” Sally purred as she gyrated above me. “I love how my pussy is stretched around your hard cock.”
“And I love how tight it is,” I replied. And she really was tight. Sally had a fantastically athletic physique, with her body honed from years of very competitive swimming. Her muscle tone was particularly impressive including, it seemed, in her vaginal walls.
The beauty of this position was that I could look up and feast – visually and physically – on her stupendous tits. Those tits, firm as they were, were jiggling up and down as Sally was bouncing away above me.
“Come on Jack, fuck me hard,” she implored, “you’ve got me so turned on. I really need to come.”
So I determined to focus all my efforts on making that happen. As Sally bore down on me, I thrust upwards. And reached round to grasp her wonderfully tight butt cheeks, to ensure more traction and greater friction of her pussy against my cock. Plus, when they were “in range”, I leant forward and nibbled on her sensitive nipples.
“Oh Jesus, yes, getting close…” she let me know, as she continued bucking on top of me. “Keep going…nearly there…”
Reaching between us, just a little awkwardly, I managed to use a finger to gently frig Sally’s clitoris. With this proving the final act that triggered her climax.
“Oooh oooh, oooh, NGGGHHHHHH, Yessssssss!!” Sally screamed, as she came to a prolonged, shuddering, orgasm.
Pausing, eventually, she looked down, with a huge, satisfied, grin on her face.
“Oh my God,” she reported, gasping for breath, “that was fantastic. Have you come again?”
“I haven’t,” I was able to assure her. “Though I’m not sure how, that was so fucking horny. So how about I put a little more work in?” I suggested, flipping Sally off me and onto her back, then easing my way into her in missionary.
“Oooh YESSS,” she hissed. “God, I love sex, why have we waited until now?” she laughed. Before silencing any potential reply by pulling me down to her for a passionate kiss.
As Sally had done with me I soon found my stride and was quickly hammering away at her. Probably, as I’ve said before, with more enthusiasm than finesse. But it was working for Sally.
“Oh God, this is fantastic,” she grunted, “come on, fuck me, fuck me, fuck me,” she demanded.
The harder I fucked her, the more enthusiastically she ground back against me, wrapping her arms around my shoulders and clenching her pussy muscles around my dick.
The bed was creaking as I was now pumping away. My second orgasm was building but I got the sense that so was Sally’s first. I could see her chest mottling, her breathing was becoming more and more ragged and I could feel her pussy contracting. Moments later I was proven right as she gripping me even tighter.
“Nnnnnnngh, nnnngh, nnnggggg, YESSSS…” she shrieked, convulsing beneath me.
This reaction, both physical, but also verbal, was the catalyst for my own orgasm.
“Oooh, oooohhhh, FUCKKKKK!!” I cried out, arching my back as I spewed a second load of spunk into her in less than an hour.
Collapsing onto the bed in a sweaty heap we lay there, in exhausted silence, for several minutes as we captured our breath and reflected on the enormity of what we’d just experienced.
In later years, as I became more sexually experienced I came to realise that it was not particularly common for women to climax through penetrative sex. And, I imagine, most certainly not the first time that they have sex. So Sally’s arousal and orgasms was another illustration of how sexual a being she was was. Though her bookish, almost dull, exterior certainly didn’t hint at those hidden carnal depths. I was just hugely grateful that, somehow or other, I had discovered them.
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For the next several months, whenever we were able to find sufficient time alone, we continued our sexual exploration together. With fucking, in an increasing variety of positions, now added to our repertoire. As I’ve related above, I really do think that this was, primarily, a physical connection. Neither of us, fortunately, got “hung up” on the other. And we clearly agreed that our relationship would never be formalsied or become public. All of that said, I look back on that period as one of the happier times of my life. With that summer particularly enjoyable.
After we’d sat our exams in June we had 3 months before going off to further education. Both of us had secured menial, part-time, work. But it still allowed us a great deal of time together during the day, without parents around. During which we did our best to fuck each other almost to a standstill!
The natural break came in late September when we both departed to University. We’d studied hard, our exams had gone well and we’d both secured places at our first choices. We were off to do different courses in different cites, but the two of us were off to amongst the more prestigious seats of learning in the country.
University is, clearly, a good place to meet new people. And in many ways reinvent yourself. I built on my increased confidence with women and, for the first time in my life started dating. Whilst by no means a Lothario I took the opportunity to sleep with a number of my fellow undergraduates. And delighted myself – and them – with my expertise between the sheets. With these sexual skills all developed, of course, with Sally.
We returned home for a weekend, mid-term, but at separate times. So we did not reconvene until the Christmas break. Neither of us were letter writers and this was several years before the advent of mobile phones. So when we did meet again we had a lot of catching up to do.
In the presence of our parents, at our first dinner together, we regaled them and each other with stories of our courses, eccentric lecturers and equally eccentric fellow students (both of us had a large proportion of “posh” public school kids at our universities).
The following day, after our parents had gone to work, we had a frenzied lovemaking session. With this setting a pattern for the next several years. We both went on to meet, date and eventually marry partners whom we both adored. But, whenever the opportunity presented itself, we continued to have some (pretty earth shattering) sex together.
Of course, as we went on to have partners this constituted infidelity (setting aside the incestuous element of it). But, for whatsoever reason, we never saw it like that. Twisted I know, as many of course, will think our whole relationship was. But, decades later, I remain hugely grateful that we found each other and set-out, very successfully, on our sexual journeys. A journey that continues, albeit very sporadically, to this day.
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