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.