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June was shorter than most people, but she was blessed with long, wavy brown hair, and she had the most bewitching green eyes set in generous black eyelashes and dark eyebrows. She first crossed my path as an actress on the wooden stage during the first rehearsal for the annual Xmas show. June was very experienced in the ways of the world of theatre... and much more than only theatre, as I would discover within her arms. June was eight years older than I was - and she had been married for about thirteen years when we met. We soon built up a mild, mutual admiration during the many weeks of intensive rehearsals, plus the following twelve nights of live performances on the stage of the local theatre, and I became the first paying lodger in the rambling old family home, which was occupied by June - plus her husband and her two young daughters.
At the "end of show" party the whole cast really let their hair down by doing some wild dancing, excessive drinking and extreme vocalizing on every subject under the sun. In the midst of all the party festivities June shocked her best friend... June leant across in front of me and whispered in her friend's ear that June's husband was going to be out of the city for the following week. And that while he was away she was going to have lots of naughty fun with her new lodger...and that person was me, pure and innocent me! Naturally I was surprised by her outspokenness and I was certain that she had been drinking far too much wine, that her alcohol intake had loosened her tongue during the noisy party...
Just a couple of days later June's husband left the city to investigate a new business proposition along the east coast. This trip left June, plus her daughters, with me in the family house for six nights... The scene was set for the loss of my sexual innocence. (At the time I was just over 22 years old and my two previous girl friends would only allow heavy petting – so that full blown sex with penetration was definitely not allowed! So I was still in the novice class! But, my male ego would never admit that to June.)
After dinner June settled her two daughters and put them to sleep in their bedrooms, while I was occupied for an hour or more in the workshop at the back of the main house. She had instructed me to come and say goodnight when I was finished in the workshop. So, I dutifully knocked on the open door of the main bedroom and June called me in to chat for a few minutes. Then she wanted a goodnight kiss - and this became a hug as she reached up with both arms to enfold me. The brief kiss became more passionate as she opened her lips and her tongue started to play games with mine. So, I knelt down at her bedside and we really enjoyed the French kissing. June sat up and she moved closer so that her breasts and nipples made contact with my chest, as she gently moved her torso from side to side. Initially, I rubbed the back of my hands across the swell of her full breasts and the stiffened nipples. She became more aroused as I continued caressing her firm breasts with my open palms through the thin fabric.
Suddenly June stopped and firmly commanded me, "Get into bed, but get out of your shirt and jeans quickly! And shut that open door!" Within seconds I had undressed to my bikini underpants and I slipped under the bedclothes to cuddle up close to her warm body. She was wearing a short, silky nightdress, but with nothing underneath that. As we carried on with our French kissing my hands wandered up and down her body, found the large opening at the front of her nightdress and so there was lots of skin to skin contact. Softly I caressed the ridges and valleys of her spine. Then my hands moved around her waist, gently trailed down her soft belly, but as soon as my finger tips made contact with her triangle of crisp pubic hair... June gasped and she pulled off my underpants to release my rigid cock, and then she rolled me on top of her. She took a firm grip of my stiff penis to make sure that it was nestled in between her pubic lips. And she gently stroked it up and down her moist slit, and then she cupped both her hands under my buttocks to firmly pull me into the wet, wonderful, warmth of her tunnel of love. The pleasure was extremely intense, so I penetrated her very slowly and then withdrew just as slowly, lingering to enjoy the feeling of her slippery pubic lips on the swollen head of my cock. And then I plunged back in again and again and again, until I set up a steady rhythm. She began to breathe very deeply and she started panting with excitement. Soon a rapid quiver took control of all her muscles and she had an orgasm with some low moans. Her internal muscles gripped and relaxed steadily as my sexual excitement peaked with a groan. As my cock became limp it slipped out of her pussy, so I rolled beside her on the wide double bed and stroked her moist skin - as I cooled down and my rapid heartbeat subsided. My hand stroked her curly intimate hair and then slid into her wet pubic lips, but I did not give much stimulating attention to her clitoris that was like a hard, little button. That long night was filled with new discoveries about female anatomy and sexual reactions, as I was very carefully guided by June with her subtle control of my sexual body. Sometime in the early hours of the morning I returned to my empty bed alone. Now I was no longer in the novice class!
The following nights were planned by June with some foresight. Instructions were given to come to her bedroom with only my sleeping shorts and an alarm clock, so that we could wake up early enough in the following morning for me to put my sleeping shorts back on and leave quietly... before there was any chance of her daughters waking and finding me in the main bedroom - instead of their own father. Each night June would greet me by waiting in her double bed in a variety of brief satin and lace undergarments, so that I had the grand pleasure of slowly undressing her, without dimming the bedside lights - before her naked body was fully revealed to me - to be admired with my eyes, my hands, my fingers and my tongue. On the final night before June's husband returned home from his trip we both agreed that we needed a full night of sleep, as we were both feeling shagged out! We retired to our beds at opposite end of the house.
For almost a year I continued to have sex with June at some unusual times and in some fairly unusual places...
Usually June and her husband would retire to bed fairly early most nights. As they departed down the passage towards the main bedroom she would turn back and whisper to me, "Do not you dare fall off to sleep! Just wait and I will come to you soon!" She told me, much later, that she would make the excuse to her husband that it was her monthly period, so she would masturbate him, or give him a blowjob. Then she would roll over, pretend to sleep and wait until she was certain that he was deeply asleep - and maybe even was snoring. Only then would she very quietly walk down the long passage to my room and we would start our real midnight fun... My single bed was rather narrow, so we had sex on two blankets thrown to the carpet beside the bed, and often her legs would be draped over my shoulders for maximum penetration. Making love on the floor was essential because the old metal bed frame, with metal springs, made lots of noise and this noise might have alerted her daughters, or even worse, her husband, who was right down the passage in the main bedroom.
We would make love on either of the lounge sofas, and we used a small orange towel to mop up our mixed juices that had stained the fabric of a valuable antique sofa on one careless night of passion. In another location, we used cushions to soften the hardness of the table on the verandah, or we just stood against the cool wall and ground our genitals together until usually I whispered, "Enough! Please stop now!"
Very early one cool morning June silently slipped into my bed while it was still pitch dark and I was deep in sleep. Her warm hands burrowed under the blanket until she located my limp cock, but she stroked it into being hot and hard, then she quietly masturbated me while I slipped my fingers into her wet pussy lips. In minutes I had shot sticky white sperm over her breasts, which she called the best massage cream! We both enjoyed it when she held my cock firmly and rubbed the tip on her stiff pink nipples. Soon I was left breathless and, just as silently as she had arrived, she left my bedroom. Later that same morning I just thought that I had been having a post-teenage wet dream! Early morning wake-up sex was an irregular feature as we could not plan it ahead of time.
One evening I arrived back at the house after dark and found just the front door lights switched on, with the rest of the house appearing to be in total darkness. But, when I stepped into the entrance hall I found that some weak light was coming out of the dining room. So I stepped through the doorway and I saw that the big room was illuminated by many burning candles... and June was sitting on the wide, recessed shelf that was part of the bay window. She was wearing one of my shirts buttoned at the navel and this shirt barely covered the lace G-string underneath it! We shared a warm welcoming kiss and she said, "I am sure that you would like some of your favorite sweet rose wine." Then she leaned backwards and poured a little chilled wine from her glass over her breasts and into her navel, so that I had to lick it off her warm body. She shivered with pleasure as my tongue softly touched her very sensitive areas and June promptly reached forward to remove my jeans and my underwear quickly, so that she had control of my rigid penis. We had a couple of hours of sweaty bliss rolling around on the dining room carpet playing "Hide the Sausage" (you do know what I mean!!). June told me that her husband had gone out to a lengthy business meeting followed by a dinner, with his promises not to return before midnight! June promptly organized things so that both her daughters would sleep over with their grandmother as a special treat. Thus the coast was clear for the two of us to enjoy some recreational sex!
Sometimes I fetched June from the rehearsal session for her next show in the local theatre - but while driving back home June would lean across to stroke my crotch to arouse me, then put my hand high up on her smooth thighs, and suddenly quickie sex would became our prime target! We would park in the cold, dark pine forests nearby and climb into the wide back seat of my trusty, white car and we would bounce away happily until the car's suspension springs were rattling and the car windows were totally misted up. Nearly an hour later we would tiptoe into the family home...both feeling warm and well satisfied!
June worked as the personal secretary in a quiet office in the city and when her boss was out on the road, or had flown to another city, she would invite me in to visit her at her workplace. Once I had arrived she would lock the outer door, switch off the neon lights and then she took me into the boss's office, where she was always cautious to close all the venetian blinds, as other office blocks might see our fun activities. She would sit on the wooden desk while we kissed and caressed, then she slipped off her blue lace trimmed bikini underwear and she helped me out of my jeans and underpants. Her hand stroked my stiff cock once or twice, she used her thumb to spread some drops of lubrication on my dark purple cock head, and then she pulled me firmly into position right between her silky thighs, so that we started up the basic rhythm of creation. Just moments before I ejaculated I picked June up off the desk and lowered her gently onto the carpet without losing my penetration. And with a couple of quick, deep strokes I was done! Her legs were wrapped around my thighs and buttocks to aid my deeper penetration. The reclining leather chair in the inner office proved to be just too much of an athletic feat for June to use for our sexual contacts. But, her boss never knew just what sexual feats we had performed on top of his desk!
Another place for our sexual meetings was the dark workshop at the back of the main house. We started kissing while standing upright, but once June had slipped off her cotton panties and had assisted me out of my jeans she would lead me to a small, but padded bench. There I would sit comfortably while she settled herself on my hard cock and then she proceeded to ride me bouncing like a bareback horse rider at a brisk trot. The delightful up and down motion soon had us over the top and I shot long squirts of warm sperm high up into her vagina as June moaned into my ears of her pleasures.
On most Saturday afternoons June's husband played golf, so June would leave her two daughters with the grandmother for at least three hours and she could return home alone to enjoy some frisky, recreational sex with me... in her double bed, on the lounge floor with a soft blanket, or crushed into my narrow single bed. When I walked into the main bedroom to find June wearing her see through night dress, and with nothing underneath it, it meant an instant arousal for me and the very rapid penetration of her sweet pussy. Two or three times June wanted us to try sex "doggie style", but for some reason she would collapse flat on her stomach and I would lose my deep penetration of her slippery tunnel, so that my cock came out of her pussy with a pop like a champagne cork! This resulted in some giggles from June.
One sunny afternoon we drove into the pine tree forest nearby, once I had scouted out a secluded area. We had carried my sleeping bag which was unrolled over the pine needles. June kissed me deeply before she slipped off her red panties, but she refused to undress any further out in the open, in case a cross country hiker might discover us. All I wanted was to caress her conical breasts and get my lips on her hard, pink nipples. In a flash I had undressed, so we got busy in the traditional missionary position and very soon my cock felt her strong vaginal muscles grip and relax regularly, so my sperm was "milked" out of me very quickly. We cuddled and kissed while June continued stroking my penis gently and cupped my ball sac with her other hand. Minutes later I rolled back on top of her, slipped back into her fur framed pussy and we pumped away furiously, which really gave both of us some fresh satisfaction and new grins! The outdoor setting was a strong stimulus for us, as all our senses were heightened by the chance of being discovered, but we did not return to that forest when cold winter winds intensified.
The parking garage for June's car was an old building, behind the family house, that had been converted from a stable and had housed horses maybe twenty years earlier. The loft above the garage had a shallow scattering of fine straw on a hard wooden floor. June enjoyed taking a blanket up into the loft with some scented massage oils, once she had gathered the straw into the corner that was warmed by the sunshine coming through a high double window. June would wear a soft raincoat and often just a red lace bikini. This setting enabled us to start with a sensual massage of each other, while getting the benefit of the sun's rays, but any sexual stimulation sooner or later led to our clothing being flung into corners of the loft as I climbed on top of her and we rolled around in a bed of straw.
Often we would finish our Saturday afternoon trysts together by climbing into a shallow, but warm bath and soap each other down. Then we would dry each other using the same towel and share some gentle laughter before we had to assume our usual roles.
As three adults sharing the large house we had some good social times that cool winter, which was helped along by regular bottles of fine Cape wine. We often sat around the wood burning fireplace and we played strip poker, which was settled by the roll of four dice. A few times we were joined by another couple, or one or two single ladies, so that there was always lots of things to talk about - or some interesting new things to view! Of course, the subject of first time sex was bandied about with everyone sharing their stories! I guess that I must have downplayed my first time sexual experience. One long holiday weekend June and her husband hired a holiday home, near miles of white sandy beaches and about four hours by road from the city. So they insisted that I join the family and, of course, I had to bring a friend. At this time I had been developing a friendship with Lynnette who was a British, honey-blonde bombshell with deep blue eyes (and who incidentally had a pair of breasts that were an outstanding asset above her slim waist). Lynnette was delighted to have a holiday with the family group.
The first night at the seaside home we enjoyed a leisurely meal, with wine flowing, at the fireside. We played strip poker for a couple of hours until after midnight when everyone started to yawn and we all headed for our bedrooms. Lynnette shared a smallish bedroom with me that had two single beds (while June's two young girls shared another bedroom). In the darkness she changed into her night wear and slipped into her bed while I undressed. Then Lynnette asked for a good night kiss, so I sat on her bed and we chatted. The chaste goodnight kiss turned passionate and she enjoyed the attention of my lips and tongue that brushed over her lips and ears. My hands soon wandered down her arms, across her ribs and finally I could cup her firm, full breasts tipped with stone hard nipples. Her wandering hands caressed my chest, rib cage and thighs. When her hand found the rigid cock that was dying for some attention, she freed it from its cotton prison, her soft, warm hand gripped it firmly and she began a slow sensual up and down motion. Within a few minutes of her skillful manipulations my cock had spurted long jets across the floor. She enjoyed the slow brush of my hand down her flat stomach, a gentle tickle in her belly button, some light touches on her pubic curls and, at last, the tiny button of her clit that was slippery and moist to my light touches. Then suddenly Lynnette whispered, "Sorry, but no further tonight. It is my bad time of the month."
Just at that moment we both heard June and her husband were making love in the main bedroom nearby. Lynnette and I both paused in the mutual pleasuring of our bodies as the sounds made by the other couple echoed through the silent, dark house. And their sex was so noisy that we easily heard June's husband made deep grunts as he came - and then moments later June had her prolonged orgasm with loud moans, groans and panting. Lynnette chuckled with me at the sounds of their sex as silence soon returned to the house, but within minutes we were asleep in our separate beds.
Walking on the sandy beach the next morning with June, she laughed with me that my holiday weekend had been spoilt by the "poor timing" of the arrival of Lynnette's monthly period at the start of the weekend. Apparently Lynnette had asked June if she had any tampons or sanitary towels while we unpacked the cars soon after we had arrived at the beachside destination. Also, June admitted to me that she had been very vocal during sex with her husband during the night - knowing that we could hear them in action and fully aware that I would be sexually frustrated!
The next couple of nights were repeated in a very similar pattern during that short holiday weekend. And most unfortunately, Lynnette admitted to being homesick and she returned to England within three weeks of our holiday together.
June never had the pleasure of being told by me that she had been an excellent teacher without the excessive use of words, just lots of action...Read more stories from our First time sex story category
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