Step-Siblings Sexual Tutorials

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This is another slow burn. It takes time to develop characters. With the sex also progressing slowly, at least at first. If that’s not for you, I suggest you click away now

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 Küçükçekmece Escort 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 lookedso 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, Maltepe Escort 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.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

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 Mecidiyeköy Escort 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.”

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