Learning the Hard Way

Author's note: This story is an updated (and elaborated) version of a near miss I experienced as a youth. Enjoy.

I suppose you could describe me as a callow lad. I hadn't very long left college, was earning a mere pittance as a trainee – couldn't afford a car, and couldn't even have driven one anyway. But the juices rose, with some frequency, whenever the opposite sex hove into view, and I wasn't bad looking, I thought, tall and blond, with long legs and a good smile.

I'd had a couple of girlfriends, but nothing much had come of it, we hadn't got past 'heavy petting' – whatever that means.

Then I went to a college dance, my old college, I had only been left about six months, and there she was. Sitting alone, hands in her lap. Wow. I had always liked long hair – be honest, men, nearly everybody does – but her hair was short. Short and very black. She had high cheek-bones, and was slim, but it was something about the way she wore that white dress that did it. There wasn't anything special about it. It was a simple, white, cotton dress, with a flared skirt. But she was just perfect in it, and I just had to take it off her – and I knew, there and then, that I would – or, at least, something evry like it, and quite soon.

I asked Wendy to dance, took her home in a taxi I could ill afford, and dated her for the following Saturday night. At the cinema, I fondled her firm young tits and kissed her eager lips, then repeated the process beside the telephone kiosk near her home, walking back to my parents' home with severely aching balls.

'Andy,' she had said, as we parted, 'I want more. I want you to.......touch me down there.' You and me both, girl – and how!

It had been a cold spring, as was the way in these parts, but it was warming up a bit now, and we had arranged to go for a stroll to evenings later, on the quiet racecourse close to her home. I chucked my jacket down behind some bushes, first checking there was nobody within miles of us, and pulled her down with me. She was wearing a light blue pleated skirt and a knit jumper.

Our lips met almost before we reached the ground, and her tongue snaked its rapacious way into my mouth at once, tracing the tips of my teeth, and driving me into a frenzy.

I then discovered that she was wearing nothing under the thin jumper – she needed no bra to support her jutting young breasts, with their hard, prominent nipples, just asking to be sucked. I obliged, pushing her jumper up to her neck. She made no protest, but her hand was exploring my hardness, stroking my rampant length outside my trousers, until its need for release was a painful urgency.

Then she was struggling with my zipper and laughed lightly as I helped by unbuckling my belt, then fought to pull down my underpants, over the awkward obstruction of my massive erection.

Then, suddenly, I was free, and she took me, tenderly, in both hands, caressing my whole length, then cupping my balls with one hand while she stroked me lovingly with the other. I gently encouraged her mouth down towards the tip of my glans, and she licked it tentatively with her tongue, looking up at me, her dark eyes large and liquid.

'I've never............' she started.

'I know,' I said, and pushed myself slowly into her waiting lips, until their lusciousness encircled first the tip, then further down my shaft, then deeply, as far as she could go.

She sucked hard, and came up for air, gasping, then down again, and back, to lick the pre-cum from my tip, with all the skill of a practised whore.

I made her stop, saying, 'If you don't stop, you know what's going to happen.'

'If that's what you want to happen, Andy...........'

'I want you to have pleasure, too, Wendy,' I replied, stroking her bare legs under her skirt, feeling the warm flesh of her thighs.

'But I'm a virgin,' she said, 'and I'm scared.'

'You don't have to be scared,' I said, feeling a thrill run through me at the idea that I might be the one to take her virginity, 'I'll be gentle.'

'Wait a moment,' she said, and standing up, she reached under her skirt and hooked her fingers under the waistband of her thin cotton panties, pulled them down and kicked them off. As she did so, I had a glimpse of her dark bush of pubic hair.

When she settled back down beside me, I resumed running my hands up her thighs, taking care not to rush things too much, gradually working around to the insides of her legs, and easing them slowly apart.

I found her slit, and her labia were warm and damp – she was obviously excited. I ran my fingers slowly from front to rear, all the way, first flicking at her erect clitoris, bringing a soft 'Oh' from her lips, then right along her cunt, and all the way to the tiny puckered hole of her anus, where I inserted my finger up to the first knuckle, something I could tell from her expression she had not expected, but which clearly excited her a lot.

'Oh, Andy,' she said, 'you excite me more than I would have believed. Do I excite you too?' She had a hand on my cock still, so the question was superfluous.

I had her open her legs as wide as she was comfortably able, and then moistened her still further with my saliva, before I very slowly started to push my eager erection into the waiting portals of her vagina. There was no more than a gasp of pain from her as her hymen was broken, and I was into her honeyed depths, where she held me with cunt-muscles that would have done justice to a well-practised adulteress. Her slender legs gripped my thighs. When she moaned with my deep thrusts, as my balls hit against her buttocks, it was in ecstasy, and the pain she had experienced in losing her cherry had been engulfed by the pleasure we had both found. We had lost ourselves in the act, and it wasn't until afterwards that we concerned ourselves that we may have been observed in such a public place.

Wendy was still at college, and finished long after my working hours were at an end. Once we started 'going steady,' I suppose I obsessed about her a bit, and, not having much else to do, asked her if it was OK if I were to go to her house and wait for her when I finished work one evening. I had never met her parents, but knew that her father was rather strict, and against her having a boyfriend.

'Yes, she said, 'that'll be OK, my Dad's away on a course, and Mum says you can come around any time.'

Although I knew that Wendy wouldn't be home for a couple of hours, I was at a loose end, so cycled round to her house, and knocked on the door, to be met by her mother.

Used to my own matronly mother, it was a surprise to meet Wendy's version, a slim, very attractive, probably bleached blonde, with long, slightly wavy hair, wearing a pair of form-fitting jeans and a sloppy tee-shirt, and carrying a mop.

'Oh, dear, you've caught me cleaning,' she said, ushering me into the lounge. 'Andy, isn't it? I've heard a lot about you. Call me Sarah, by the way.' I wasn't sure I liked the sound of all that, but she put me at my ease, and sat me down on the sofa, putting on a compact disc, which, slightly surprisingly, turned out to be rather cool modern jazz.

'I'll just go and change,' she called from outside the room, and was gone for perhaps ten minutes.

When she came back, I was looking at a magazine I had found on the coffee table, idly leafing through, and at first I didn't take any notice, but then I had a shock. I half looked around, and there was Sarah, stood behind the sofa, in a sheer black negligee, through which could be seen every detail of a pair of magnificent breasts, with large, protuberant aureolas. She smiled slyly, and stroked my hair gently, then rubbed her tits around the back of my neck. My cock sprang to attention unbidden.

She walked slowly around the sofa, and I saw that she wore not a stitch under the negligee.

'Like what you see, Andy?' she asked.

I gulped.

She sat beside me and I caught her heady perfume –Rive gauche, I thought – then she slowly, ever so slowly, pulled open the cord of her negligee, letting it fall open to reveal a perfectly bare, shaven mound. She turned half towards me and, raising the opposite leg slightly, she ran the fingers of one hand very deliberately between the luscious lips of her moist cunt. She was presenting it to me, as if for inspection, and opened her labia with two fingers, then inserted the forefinger of the other hand, straight up her fuckhole, as far as it would go.

She moaned as she did this, and threw her head back with abandon. I took over the position of her hands with mine, pushing her legs further apart, and swivelling down into a kneeling position in front of the sofa. Then I buried my face deep in between her thighs and tongued her dripping cunt until she moaned loudly. As I did this, I found her arsehole with my fingers and was somehow unsurprised when two fingers readily slipped into the hospitable depths. She gave an animalistic groan, and seized me by the hair, pushing me deeper into her eager pussy.

'Fuck me, Andy,' she said, 'now.' It was an order, and I was nineteen. Was I to disobey?

Without further ado, I plunged my ramrod straight into her, and her cunt-muscles took control in a way she couldn't know that her daughters' had done so recently. But I had no time to muse on genetics, and half-a-dozen thrusts were all I could manage before I shot my urgent load, and collapsed exhausted across her. She assured me that she too had climaxed, but whether she was just being nice, I couldn't be sure.

In any event, she wasn't finished with me, and, giving me a few minutes to recover, she eased me gently out of her, then started to play with me, at first gently running her fingers around my flaccid prick, then bending down and licking, sucking and generally playing with me until I felt myself slowly growing hard once more.

She came up for air, with a mischievous grin, just like that of her daughter, and then reached around behind me with one hand. I suddenly felt the electric shock of her long forefinger going straight up my rectum! That did it. I was suddenly as hard as a rock.

'Now,' said Sarah, 'Fuck me in the arse, Andy – that's what I really like.'

With that, she spun around and presented her perfect, rounded buttocks to me. She put her hands one on either cheek, and pulled them wide apart, showing me the gaping dark chasm of her well-used anus. I had never fucked arse before, and was intrigued to feel my cock encased in its sheath. I hadn't long to wait, as she was impatient to receive me, reaching behind for me to pull me home. I delayed a moment as I entered her, my knob thrusting at her entrance, then I was through to her sphincter, and grasped by her hot centre. She shouted with delight when I felt for her clitoris and found it wet and erect, and I then plunged three fingers deep into her cunt, moving them in rhythm with my fucking of her arse. Having come so recently, I was able to resist longer now, and she must have had at least three orgasms before I could hold off no longer, and came in creamy spurts, deep into her bowels.

When we had cleaned up, and Sarah had changed into a track-suit, there was almost half-an-hour left before Wendy was due home. We sat comfortably and chatted.

That evening I took Wendy out for a drink, and she seemed surprised when I didn't seem very interested in the passionate kiss she gave me when we parted.

A couple of days later, I had a note from her at work. She had been offered a place at University, and was going to be very busy studying. Would I mind not seeing her until further notice?

I haven't seen either her or her mother since.