In a few months time I will have lived my allotted Biblical span of three score years and ten, and whilst I am still in good health and hope for many more years of active life, the years of my sexual prime now lie well in the past. Looking back to my teens, it would be easy to exaggerate my youthful sexual experiences, but I’m afraid that most of those who describe adventures of which Casanova would have been envious are looking through the distorting lens of history.
The so-called Swinging Sixties might have been the decade when the sexual liberation of the modern era began, but in the U.K. most young people from the middle classes reached the altar as virgins. Young women were still taught that nice girls ‘don’t’ and the fear of pregnancy was all too real. Family Planning Clinics would only see women who were married, or soon to be married, and the contraceptive pill was very rarely prescribed for unmarried women except for good medical reasons.
So, in common with the majority of my contemporaries — despite their boasts of sexual conquests, I was still a virgin when I reached my eighteenth birthday. To be fair I was not unacquainted with female anatomy, and had groped my fair share of delicious young boobs and had managed to get my hands into the panties of one or two more pliable girls. I also masturbated regularly over the pictures in girlie magazines, although vaginas were still airbrushed out, so I had never seen a pussy in all its glorious detail.
ooOoo
Just before my eighteenth birthday, new people moved into the house next door. He was in his mid-forties, but she was much younger, probably in her early thirties, and unusually for the time, were still childless. I didn’t take much notice of the husband, although I learned from my parents that his name was Roy, and that he worked in the City. On the other hand, teenage hormones meant that I took a more than innocent interest in all attractive women under the age of forty, and I made the most of every opportunity to ogle Jill from the safety of my bedroom when she was working in the garden.
Roy took the train to London early every morning and didn’t get back home until seven in the evening, and was often away on business for several days. Jill didn’t work and her only company during the day was an Airedale terrier which she took for long walks every day in the nearby woods. During the school holidays one of my household duties was to take our dog for its walks and to be totally honest I deliberately chose a time when I knew that there was a possibility I would bump into her. The first two or three times we did no more than politely pass the time of day but one day Jill struck up a conversation. I may have lusted after women of Jill’s age, but when it actually came to talking to one I became rather tongue-tied, which people who know me now might find slightly unbelievable. Jill broke the ice by asking about what I was doing at school and what I intended to study at university. She went on to ask about my hobbies which promised to be a more fruitful line of conversation. I replied that I enjoyed reading and that I did a little bit of painting. It turned out that we had similar interests in music and the arts but most of all the kind of fiction we liked, and started comparing notes on the various authors we had read, which progressed to recommending books that the other might like.
When Jill suggested that we might like to walk together I jumped at the chance to spend more time with an attractive older woman, who seemed to be so much more sophisticated than the girls of my age. Over the weeks our friendship grew and once I had started to revise for my A levels and was at home all day on my own, she suggested I might like to join her for coffee at around eleven thirty every day, before returning to my studies.
Jill was around five foot seven, with a slim boyish figure, pretty face, and short curly sandy coloured hair, not unlike her dog. She had a good complexion, but used very little makeup, preferring the natural look, and always smelled fresh and clean. Most of the time she wore a shirt and slacks, often with a pullover. As the weather got warmer, however, she started wearing mid-thigh length skirts, but without stockings or tights. I tried not to show it but I was finding her increasingly attractive, and used to fantasise about seeing her naked when I was masturbating, although I did not expect anything would ever happen between us.
However, our innocent relationship changed dramatically one morning in late May, a week or so before my exams were due to start. I had gone round as usual to find Jill looking particularly attractive, and wearing a white cotton blouse and blue gingham skirt. After she had prepared coffee and I was sitting at the kitchen table, she hitched herself up onto the work surface with one foot on the table in front of me, causing her skirt to slide up her thighs, giving me a view of her white cotton panties. I tried not to stare but as we talked, she parted her legs wider so that now I was looking straight at the gusset of her panties.
You can imagine the effect this had on me; I was forced to readjust my shorts to accommodate my growing erection, which I thought was hidden from her sight by the table. However, Jill looked me straight in the eye smiled, and said, “Seems like someone has seen something rather exciting, I wonder what it could be?”
I must have blushed, because she laughed and said, “Why don't you go and sit on the settee where we can get to know each other better? Don't be shy, I won't eat you — not yet anyway.”
She jumped down from where she was sitting and taking my hand led me through to the living room. When I sat down my arousal was embarrassingly clear and as she was sitting down beside me, as if by accident Jill put her hand on the prominent bulge in my shorts. “Mmm, you are a big boy, and those shorts are rather tight. Why don’t you let me make you more comfortable.”
Without waiting for an answer, she undid my belt and the top few buttons of my flies, and then slipped her hand inside the waistband of my underpants to fondle my erection. Nobody had ever done that before to me, and it felt absolutely wonderful.
“Naughty boy,” she said, “I’ve seen the way you look at me. I hope you think about me when you are masturbating, or do you prefer the girls in the magazines?”
I blushed an even deeper shade of red, and managed to stammer, “But you are a married woman.”
“Poor boy, I’ve embarrassed you,” she said, laughing, “don’t be ashamed, I find it rather flattering that a handsome young man like you finds me sexually desirable. I think you are rather gorgeous yourself, and I’ve often wondered what you look like naked. Why don’t you take your clothes off so I can see you properly? Maybe you need a little encouragement.”
Without waiting for an answer she leaned towards me and putting one hand around my neck, kissed me passionately on the lips, while undoing the buttons on my shirt. After a few very enjoyable minutes Jill pulled away and got up and stood in front of me.
“Now be a good boy and do as you’re told. I want to watch you stroking that lovely cock like you do when you’re thinking about me, and I’ll give you something much nicer to look at than the girls in your magazines — I don’t suppose you’ve ever seen a real live naked woman.”
While she was talking, Jill slipped her skirt down and unbuttoned her blouse to reveal a lacy bra enfolding smallish but well-shaped breasts. After removing her blouse and undoing her bra straps she kissed me again, allowing her bra to fall off so that her breasts were rubbing against my chest. Coming up for air after a few more delicious minutes she stood up again and said, “Would you like me to take my panties off so that you can see my pussy.”
“What, are you sure?” I stuttered, almost speechless with desire. This was so naughty.
“Of course,” she replied, “It will be really exciting to watch you cumming for me while you’re enjoying your first sight of a pussy. And then I’m going to let you fuck me.”
This was far more than I had ever dreamed of and I rapidly took off my shirt, shorts and underpants and sat down again, my cock standing up hard and throbbing with excitement. Jill turned around so that she had her back to me and hooking her fingers into the top of her black lacy panties, slid them over the cheeks of her shapely bottom and down her legs. She then parted her legs and leaned forward to give me a fantastic view of her wet pussy, beautifully framed by soft curly hair. Her labia were swollen and pink, and the entrance to her vagina was slowly opening and closing.
Turning to face me again she parted the folds of her pussy and pulled back the hood of her clitoris and began to rub herself with one hand whilst plunging two fingers of the other hand into her vagina. The eroticism of this show of explicit female sexual beauty just a few feet in front of me was so arousing that after a few strokes of my cock I knew I was going to cum.
“Go on lover,” Jill moaned, “Cum for me. Let me see you spurting your delicious cream for me.”
That took me beyond the point of no return and I erupted in streams of hot cum. When I had finished Jill went down on her knees and leaned forward to lick the sticky cum off my chest and tummy before taking the head of my cock in her mouth, whilst stroking the shaft in one hand and fondling my balls with the other.
“Mmm, that was good wasn’t it?” she murmured, “Now it’s my turn, but before I let you fuck me I think you should get to know my pussy better.”
Straddling my thighs, Jill took my hand and pressed my palm very softly against her pussy, my fingers on her mound pointing towards her heart. “Feel how plump my outer lips and mound are, doesn't that feel nice?”
I just nodded again – I had completely lost my voice. “Now explore the folds of my inner lips, spread them out and gently squeeze and stroke them, enjoy their silky softness. Oh, that's good, it feels really nice.”
Jill started to buck her hips as I continued my exploration, moaning quietly, her mouth slightly open, and a look of utter concentration on her face. “Run your fingers up to my clitoris, feel how the head is just poking out of its hood. Touch it very gently, it is very sensitive,” she said. “Ooooh, you are a very good boy, I am getting so aroused. Put two fingers inside me. Now curl them up so they are touching the front wall, and thrust them in and out.”
Jill was by now on the verge of ecstasy, and a flush of pink had spread up her chest and across her face. Her body was writhing and her back arched as her climax grew close. She pushed me back so I was lying on the settee and moved up my body until she was straddling my head with her pussy over my face.
“Now suck my clitoris and make me cum,” she said, between her moans.
As I did so, tasting the distinctive flavour of pussy for the first time she pulled my mouth hard into her pussy and after a few moments her body went rigid and she screamed out in delight, “Yes, yes, yes, oh yes.”
When she had recovered from her orgasm Jill slid off me and lay on the floor with her legs apart. “Come and fuck me now, you lovely boy,” she murmured, “Fuck me hard, I want to feel you inside me, plundering my cunt.”
By now my cock was rock hard again, and moving until I was lying on top of her, I put the head in the entrance of her vagina and slowly pushed the length of my shaft into her slick heat until my balls were resting against the cheeks of her bottom.
“That’s right,” she said, “Thrust your lovely young cock deep into me. That's right, go on, harder, harder, ooooh...”
The feeling of my cock sliding between her swollen lips as I thrust deep into Jill's velvet hole was amazing, and being young it only took a few minutes of fucking until I was ready to cum again. The feeling of my climax was far sweeter than I had known through masturbation and exquisite waves of pleasure radiated throughout my body, my legs rigid and shaking with the power of my orgasm.
When we were done, we lay on the settee face to face for the next half an hour or so, kissing passionately. The feel of Jill's naked body next to mine was so wonderful, her soft breasts pressed against my chest, and her wet pussy against my upper thigh. As I recovered from my climax, my cock started to stiffen again, and when I was really hard, Jill rolled me onto my back, and straddling me, proceeded to fuck me. I lasted much longer this time, and we came in mutual orgasms of overwhelming intensity.
For the rest of the summer, we found opportunities to make love as often as possible. It was through Jill that I grew to love having sex in the open air. When we went for our daily walk in the beech woods near our homes, Jill would often leave her panties off, and encourage me to slip my hand under her skirt to have a good feel of her bottom and pussy. Once we had found a secluded glen she would then lean against a tree and lift her skirt to give me a delicious view of her pussy, which was usually very wet by then, and tell me to get my cock out and fuck her silly. At other times she would undo her blouse and kneel in front of me and then pull my shirts and underpants off and beg me to wank all over her breasts, or for a very special treat give me a blow job. The feeling of the sun and breeze on my naked body when I was cumming was fantastic, and there was always the added thrill that someone might see us. Ever since I have found that a little danger has a very stimulating effect on my libido.
My parents habitually took a fortnight's holiday on their own every summer, leaving me in charge of the house. They would leave me a list of jobs to do — my father was a very good gardener but he was no handyman and encouraged me to take on practical tasks such as decorating or minor structural repairs. There was plenty of time however, to continue my sexual liaison with Jill, and I was in seventh heaven when she told me that Roy would be away for a few days and suggested that I should join her in the marital bed. An additional benefit of this arrangement was that I would be fed as well as fucked which suited me down to the ground — a rather male chauvinist attitude I’m ashamed to say, but maturity has made me more egalitarian and I do my share of cooking and housework these days.
The first time I went into Jill’s bedroom I had a bit of a shock. On the wall above the bed was a lifesize black and white photograph of Jill totally naked and riding a very realistic phallus. I knew nothing about sex toys at that time, but Jill explained that women could have multiple orgasms over a sustained period of time. She went on to say that in addition to pleasuring her orally before and after fucking her, Roy would use the dildo to prolong her pleasure until he was ready to cum again. When I asked about the photograph, Jill told me that photography was Roy’s hobby and that he had a very well-equipped dark room, and enjoyed taking erotic and very explicit photos of her.
I could fill a book with descriptions of our passionate lovemaking that summer which went far beyond the norm of face-to-face fucking in the missionary position. Jill turned out to be sexually voracious and inventive and together we ventured into some more exotic sexual practices such as rimming and anal sex, which was not on my sexual horizon until then. I will always be grateful to Jill for everything she taught me about female sexuality that summer — practical knowledge I could never have found in books but which I have put to good use ever since.
ooOoo
At the beginning of October when the time came for me to go up to university, Jill gave me a small photograph album to take away with me. “Don’t open this until you are alone in your room. I know that you will find a young woman of your own age very soon, but until you do I think you will find these photos of me much more exciting than your girlie magazines, and it will give me great pleasure to know you are masturbating thinking about me.”
When I came home at Christmas, the house next door was up for sale. My mother told me that Roy's job was taking them back north, and they were looking for a house near to her parents, which was nice because she was expecting a baby in February — apparently they had been trying for some time, and were overjoyed at her pregnancy. We never met again, but I will always remember with great pleasure that summer when Jill took my virginity and taught me how to please a woman.
