Lillian became a regular member of our family, by that I mean she, Catherine and Mrs. McDonald and I became regular intimate friends. What I loved about our friendship, she opened a lot of doors for me into the upper classes of society. I may have been what a lot of people would call a slut, but I was not stupid.
I’ve always been attracted to money and nice things, Catherine was the first. We first met in the restaurant where I worked, she was a generous tipper so I’d give her special attention. She told me about her family being in the mining business, so I assumed she was wealthy. She was my first lesbian partner, and it turned out it was something I loved. Also being submissive, she loved to cater to me hand and foot.
Marlene McDonald I met with Catherine at a club for women, she took me under her wing so to speak. She was a very dominant lady who saw the hidden strength in me, and was pleased to invite me into her circle of friends. She was the head mistress of a secondary school, and had a lovely old stone home. She and Catherine were both upper middle class ladies, who fortunately saw something good in me. Marlene was of what she called, “The old school,” that enjoyed disciplining those who needed punishment, for an ‘attitude adjustment.’
Life for the upper classes was different in those days, some married for money, but mostly for social reasons. Lillian was to introduce me to a number of upper class wealthy people, mostly men of course, but a few ladies too.
Lillian was a dream comes true for me, very much upper class who took a liking to me. She was a voyeur and habitual masturbator, and in her middle sixties she still had a healthy libido. Once she realised her husband had other affairs, she began to enjoy some extramarital affairs herself. The big thing for them was discretion, they felt they could do what they wanted. It was very important to them, too been seen as loving couples in public.
I was learning fast, thanks mostly to my Catherine, my work on ‘speech and deportment’ seemed to be paying off. Lillian particularly appreciated this, and was happy to invite me to many social events. I soon realised that by playing my cards right, I could be accepted into the right circles. It might have been temporary at the time, but I didn’t care.
By now I accepted I loved money, fine clothes and of course sex. I was Beautiful even if I say so myself, and often chased after by men. I could pick and choose, with the deciding factor being two things. One was how wealthy was the man and two, how much was he willing to spend on me. Of course I was always willing to show him a ‘good time,’ as a result of his generosity.
I was definitely becoming a snob, and admit worked hard to ‘fit in’ with the gentry. I was usually quite shy in public, something the men liked. To be seen and not heard, was paying off with my dates. Lillian was helpful here, informing what she knew about the people I met at social Functions. I was quick to realise that the picture presented to the public, was often totally different from what they were like in private.
I was often invited out for dinner or to a show, I never asked about their relationships with their wives. I was only interested in me, and what I could get out of my dates. Of course I never mentioned or asked for money, but expected to be compensated for my ‘attention to details.’ Lillian was very helpful in passing on my interest in dating, as well as how ‘entertaining’ I could be.
Often their wives were aware of their husbands interests, a lot of them had married for the right social reasons. While some men had mistresses, in a lot of cases the ladies had their lovers too. Lillian as I mentioned before, had a few lovers over the years, with both men and women. I loved her attitude towards these liaisons, she didn’t see anything wrong with having a night of fun with someone you liked.
Discretion was the one thing everyone wanted, I wanted it for myself too, as well as my dates. The reason I never directly asked for money, I didn’t want people to think I was a whore. Thanks to my friends Ms. McDonald, Lillian and of course Catherine, I had honed my social skills to an acceptable level. Now I was quite comfortable mixing with the best of company in public.
My sexual skills I’d worked on so I could really please my partner, a man or a woman. Something I loved was the foreplay, to tease and titillate so they would derive the maximum pleasure. I could do a very good strip tease, something I learned from a lady from India. Also from Ms. McDonald I learned the skilful art of inflicting pain, be it with spankings and floggings.
John I’d met a few times at Lillian’s social evenings, a handsome man in his mid fifties. I liked him as he was always so gracious, seemed to single me out for conversation when we met. He travelled a lot on business, so I thought it was a question of opportunity, before he would invite me out for an evening. I was sure Lillian had passed onto him my interest, in one way or another.
His wife Nancy was also quite cultured and a very friendly lady. In the confines of Lillian’s home, she didn’t seem to mind his flirting with me or other guests. Nancy was what I would call handsome rather than pretty, very attentive to her husband in public. She would wait on him hand and foot, often when they were leaving she would put her coat on, then get his and wait patiently by the door till he was ready to leave. Often as much as half an hour later, then helping him into his coat, turn and say “Goodbye,” with no hint of anger or impatience.
She was a remarkable lady and always immaculately dressed, with the most fashionable clothes and jewellery. One couldn’t help but admire her composure, even though her husband obviously took her for granted.
One night I commented to Lillian on this, asked her why did she put up with his behaviour? As I said I liked the man and hoped for us to get together, still there was a concern as to how he might treat me. “What’s he like in private,” I asked her.
At this Lillian said with a smile, “You have so much to learn my dear.”
She did not elaborate on that, just left me wondering what she meant by that. However she did go on to say that given the chance, I might be pleased with the outcome.
One night we were in our club and Nancy dropped in, she was not a regular but of course was always welcome. She came in to tell us that John would like us to ‘join them’ for supper in a week’s time, when he would be back home from a business trip.
Lillian asked me, “Well what do you think?”
Of course I was sure of his interest in me was more that platonic, and had been expecting an invite for a date. Still what surprised me, was that it was his wife who was doing the inviting. I mean being opened minded and turning a blind eye was one thing, but to actually invite someone who, as I said knew he was interested in? This was puzzling to me at the time, but agreed to go along with the invite.
My instincts told me that something wasn’t right about this, and said I wanted Lillian to also be included.
“Of course,” she replied with a smile, “If you’d like to join us too Lillian.”
“Why yes” Lillian replied a little too eagerly, “I’d love to.”
A few days before the Saturday in question, I received a package in the mail from John. It was a rather kinky and expensive silk lingerie outfit, attached was a note asking me to wear it to him dinner. It was lovely rose coloured ensemble with pretty French knickers, embroidered with lace around the bum and leg openings. Included was also a lovely pair of silk stockings.
As they lived quite a bit outside the city, Lillian said she would pick me up and we would go in her car.
I admit to being more than a little excited, and bathed and got dressed in lots of time. I selected a rather formal, pale red dress to wear over it. I was nervous waiting for Lillian to arrive. Once she did she suggested I could drive, she knew how much I enjoyed driving her Jaguar.
The house or rather the estate I should say, was about an hour’s drive up into the hills above the city. It was a very large impressive looking house, sitting in amongst a lot of well manicured acres. Screened from the road by trees, we drove up a curved driveway and parked outside this stately home.
The scenery took my breath away, obviously this man was extremely rich. Later I would learn he was an international lawyer, who dealt a lot with large businesses as well as governments.
The door opened and a voice called out, “Come on in and glad you could make it.” Lillian took hold of my arm and led me up the few steps to the entrance. Nancy was there to greet us, she was dressed more like the maid than his wife.
Her outfit was a short black dress with a bib front, cut quite low that showed the top of her boobs. There was lace trim round the back of her neck, that matched a lace hat on her head. The dress was very short, so much that when she sat down her stocking tops showed
I didn’t know what to say or do just followed Lillian in taking our coats off, and handed them to Nancy to hang up. As she was doing this she made small talk about how our trip up had been, just matter of fact as if she always greeted guests in this uniform.
We were shown into the living room, there John came to greet us with a hug.
“Please take a seat,” he said and gestured towards a very plush looking sofa.
He was a handsome man and looked very clean, close to him there was just a slight with a whiff of aftershave. He was dressed casually in a white shirt opened to his breast bone, and wearing a pair of immaculate cream coloured slacks.
Candles were burning in holders round the room, giving off a nice glow. A log was crackling in the fireplace, and an odour of incense permeated the room. He had me sit on one side of him, and Lillian on the other side of him. A few moments later, Nancy served us drinks on a silver tray. It was for me a very posh experience, but Lillian was obviously quite comfortable.
As was usual for me when meeting like this, I wasn’t sure what to say. So I sat there on the edge of my seat, feeling a little intimidated. Lilly and he chatted away for a time, and about all I did was answering some questions. The wine was very good, and I tended to drink a little too quickly. I took my cue from them, and tried to slow down to match their pace.
Nancy would pop in every so often to offer us more wine, Johns encouraged us to drink up. It was a relief when Nancy announced dinner was ready, and we walked with John to his dining room. There we had a splendid roast beef dinner, followed by some black forest cake, all washed down with lots of wine.
After the meal he led us into his ‘den,’ where we enjoyed a glass of port. The den had also been prepared with candles round the room, and again there was the sweet smell in incense in the air. It was a very heady atmosphere, and I was by now relaxing and enjoying myself.
Nancy stayed to clear away the dishes, taking them into the kitchen to wash up. She had been kept quite busy with the meal, serving drinks, stoking the fire and changing records on the stereo.
John asked how I liked his gift, and I said it was beautiful. He smiled at me and said, “I heard you like beautiful things.”
As he said this he put his hand on my knee, just at the hem of my dress. I didn’t move it just I straightened my legs and in reply said, “I particularly love the silk stockings.”
He muttered, “Yes they’re so sensual I love the feel of them too.”
At this his hand started to move up and under the hem of my dress. Of course I knew where he was going with this, and wondered about how fast I should let him proceed. At this I closed my knees on his fingers, and reached down and held his hand. I didn’t move it, just held on to it.
Over his shoulder I say Lilly watching this, her expression one of amusement. She was enjoying my embarrassment in a way, although she had a lot to do with my being in this situation. Of course by now I loved it, aware of the sensations being produced within me.
“I hear you’re a very good dancer,” he said suddenly.
“Oh I don’t know,” I said modestly.
He got up and went to the stereo, and changed the record for a very slow waltz. Now turning to me smiled holding out his hand and said, “Come.”
I got up and he held me close, placing his cheek against mine. I smelled his after shave, we just swooned to the music. It was an excuse to hold each other close his hand at my waist and moving over my hip. He pressed a leg between mine, his mouth nibbling at my ear. I felt his manhood get erect, it was a feeling I loved when dancing close. I pressed my torso against it to indicate my desire, he responded with his hand gripping the cheek of my arse.
I was feeling quite randy by this time, and next the music stopped and a fast tune blasted out. I took the opportunity to break off the closeness, and began to jive to the music. John laughed and started jiving with me, he was surprisingly good at it. Twirling me around up and over his arms, my bum flying from side to side had my dress flying up to my waist.
Lillian applauded this and her calling out, attracted Nancy who also came in to watch our performance.
Once the music ended we took a break, to catch our breath and enjoy a drink. Nancy commented on how we were jiving together, and Lilly said, “You should see the strip tease she can do.”
That started a chorus of them urging me to do the dance of seven veils, I was pleased and a little embarrassed in a way. But I’d had quite a few drinks and was having a great time, so I thought, “Why Not.”
Nancy found the right music and played it on the stereo, now to their calls of encouragement I began my dance. I began by twirling around the room, arms up and curved over my head. Of course I didn’t have the veils or the right clothes on, but would have to improvise.
What is difficult here is to describe the atmosphere in the room, the candles produced a very mellow and dim light. The fire had burned down quite low, the room was already very warm from the heat of the fire. I hadn’t noticed how, but Nancy had kept the incense burning. It produced a very warm and exotic feeling in me, as I’m certain it did to the others.
As I turned and twisted to the sound of the music, the ladies started with a chorus of suggestions. It was a definite turn on for me, as they also encouraged me to ‘take it off.’ I paced myself so as not to disrobe too quickly, making suggestive moves in front of the host. Slowly I unzipped my dress down the back, pushed it off my shoulders and holding it over my breasts. Now I cupped a tit in each hand and bowed low in front of John, giving him a good view of my upper boobs. Slowly I lifted the dress away and let it fall to my waist, to reveal them in the pretty lacy bra he’d bought me.
I was pleased to see him shift positions, and place a hand at his crotch to adjust his privates. I smiled and winked at him knowingly, then turned my back to him. I was continually moving as I did this, and swivelling my hips in a teasing manner. Backing up to him bent over, I pulled my dress over my buttocks. His hands came up to touch me, I wiggled my bum squealing with pleasure, and danced away from him.
The two ladies were obviously enjoying the show as well, Lillian was the more vocal of the two. I was not surprised by this, as I knew she loved to watch any kind of sex act. Taking my boobs one in each hand I danced over to the ladies, and bent over to give them a good view of my tits. I unsnapped my bra and took it off, wiggling my shoulders to make my tits fly in front of them. Now as they reached out to me, I danced away smiling. Standing upright I twirled around the room, swinging my bra over my head. As I did this I also pushed my dress over my hips and down to my feet.
I let my bra go and covered my tits and crotch in mock modesty, my bra landed on John’s head. I noticed John had undone his trousers, his cock in his hand was a solid as a pole. This was a definite distraction, and it took a great deal of will power to pretend to ignore it. Kicking my dress away from round my feet, I took a tit in each hand and leaned over to present them to him. He stared in amazement, I kissed my own nipples. I loved the feel of my tits when aroused, I was so randy by now, and it was difficult to keep up the pretense of dancing.
Still bent over I turned my back to him, this time I felt his hands run up my thigh. The pressure was intense, I wanted to feel that magnificent cock inside me. The ladies were still shouting encouragement, singing “Sing sing or show your ring etc.” Calling out, “Knickers off, give it to her Johnny,” etc...
The ladies by now had ‘exposed themselves,’ and Lillian was quite gleefully fondling her pussy. I was so high I couldn’t have stopped him, I was only too happy to feel him pull my knickers down. I was bent so low I put my hands on the floor, I felt more than ready for his entry. My pussy was dripping wet, he leaned his face into my arse and kissed my vulva. With my knickers at my feet I lifted one foot out of them, and opened my legs in anticipation.
Most men would have been shagging the arse off me by this time, but not John, he was giving me as good as I gave him. He turned me around and gripped my hair, in a way that made me fall to my knees. Holding my hair he lifted my head up, I was smiling up at him. There just an inch or two in front of my face, was that magnificent cock, still as solid looking as a rock.
It was big, the ‘bobby’s helmet’ shining with precum. I wanted to feel it inside me so bad, I knew I’d have to wait. Still holding my head he sat back down, he was in charge. At least my hands were free, with one I took hold of his magnificent shaft, and with my other felt the softness of his balls. I concentrated on performing fellatio on him, something I was skilled at. I licked that shaft, sucked on the tip running my tongue around it. I kept my eyes on his, he was smiling in return. He had excellent stamina as I sucked him, taking it all the way in my mouth then out to savor the tip.
I felt him tense moments before his cum, it gave me time to take it in my mouth. I held it in my mouth till he’d finished ejaculating, and then feeling it softening I slowly let it out. I kept licking to get the last drop of cum from the tip, and could tell from his eyes he appreciated that.
Disappointed I didn’t get to feel that shaft in my pussy, I hoped I get to feel it later. Then there were men who would save that part for their wives, I hoped he wasn’t one of them.
I’m certain he knew what he was doing, deliberately making me wait to be fucked. It was important for him to establish himself as the master, to be in control yet he had given up some control to me in a way. Yes it was him who asked me to dance at first, but then it was Lillian that suggested I should do a strip tease for him.
I did the only thing I could think of, to show I had good control too. I went over to Lillian and taking her hand and pulled her up to dance. I was certain John knew we were queer, if not then he was in for a surprise. Not only that, but I too needed some release.
Her dress was a black sheath type dress, buttoned up and down the front. She herself had undone the buttons from the waist down, in order to ‘entertain herself’ from the exposure of me entertaining John. Also, I was confident she would be happy to accommodate me.
There was no resistance as I finished unbuttoning it, and pushed it off her shoulders letting it fall to the floor. As I’ve said before, she was in remarkable shape for a lady in her mid sixties. I felt no doubt John had previously enjoyed her charms.
She didn’t let me down, she responded to my embraces willingly. Swaying to the music, I got rid of her bra and pressed out tits together. Her fingers also embraced me, dancing all over my back and hips. My hands were not idle either, caressing her and cupping her nether cheeks. My hands pulling her body into mine, our legs pressed into each other’s cunts.
Suddenly she pulled back from me for a moment, and I felt another hand come around my shoulders. It was Nancy, she didn’t want to be left out of the fun. Lillian knew a great deal about the intimate tastes of our hosts, something I was to find out later.
Now there were two pairs of hands to please me, and two bodies for me to play with. It was more like maintain an arousal, I wanted more and let them know it. My legs were getting weak, and I wanted to lie down and get my pussy explored.
Lillian, bless her heart knew me well enough, she whispered something to Nancy. At this she lay flat on her tummy and buried her face into my cunt. Lillian knelt behind me, and lifted my head onto her thighs. She leaned over me to stroke my tits, I just relaxed and enjoyed their attentions.
I got quite vocal as my adrenaline mounted, and soon had the most powerful climax. I rested for a moment and Nancy got up, now John was in front of me. His most beautiful cock was hard again, standing up as stiff as a poker. My legs were already wide apart to receive him, it was the most delicious feeling as he slid it into me.
His face inches from mine as he began his thrusts, I wanted to feel it right at the back. I groaned from the pleasure, maddening as it was he took his sweet time. Just a little at a time, each time going a little deeper. I lifted my legs straight up, one on either side of him and pleaded, “Fuck me.”
He did just that, with Lillian holding my head on her lap as he pounded me. My orgasm was the most powerful, and he didn’t stop. He had the most amazing endurance, till at last I felt him stiffen. He flooded my cunt with his cream, the feeling against my cervix was awesome.
After he got up the girls helped me to my feet, my legs were so weak. As my strength returned, his cum started to drip out of me. It felt so good, and I went and sat next to him on the sofa. I took his now slack cock in my hand, feeling the slime from my pussy.
He placed an arm around me and gave me a hug. “That was an amazing fuck,” I told him.
“Lillian was right about you,” he said, “You’re an amazing woman.”
After another drink he took me to his bed to sleep with him for the night. Lillian and Nancy disappeared into another room, and I fell into a deep sleep.
In the morning, Nancy brought John and I some tea in bed, “You have a good night,” she asked? Then smiling left us alone.
It had been the most awesome night I’d ever had to date. John was in no hurry to get up, and seemed to be happy to have me with him. As Nancy had been in on it as well, I had no problem accepting what had happened. Once we had our tea, we settled back down. I placed a hand on his thigh, stroking it till I felt his manhood start to stiffen.
He had an arm around me, and I could smell his manliness. I leaned up one elbow and looked at him, directly in his eyes. Smiling I placed my hand on his cock, he smiled back at me and just let me play with it. I stroked it for a while, enjoying the feel of its stiffness. I saw the pleasure in his eyes, as he waited to see what I would do with it.
I kissed the head, tasting the mustiness from the night before. I didn’t mind, I knew how this pleased a man. I took the head of it in my mouth, let him feel my tongue on it as I slowly sucked it. This also excited me, so I got up and straddled his legs took the whole thing in my mouth. I loved to deep throat a man, I knew how much they enjoyed it.
I didn’t go all the way, when I felt ready I turned round and straddled his chest. Now I had my back to him, as I faced his feet. I brought his cock to the lips of my pussy, rubbing the head against my labia’s and clit. It was awesome until I felt more than ready, and then slowly entered it into my now juicy pussy.
Leaning forward I placed my head between his ankles, feeling that delicious pressure against his prick. He placed his hands on my arse, pressing my butt cheeks apart. I knew he wanted to watch his cock, as I moved my arse up and down slowly to please him. This movement for me was very intense, I closed my eyes and concentrated on the pleasure. After my orgasm I felt him cum, and then collapsed on his legs to enjoy it.
He paid me a surprising complement on my performance, telling me he had never had sex in that position before.
After I took my time in his bathroom, it was huge with a sunken tub and something called a ‘bidet.’ There was a nice selection of fragrant bath salts, so I relaxed in the tub and enjoyed some time for myself. By now it was late in the morning, and the girls had made a nice brunch for all of us.
Sitting around the table, John asked me how I enjoyed myself. I was honest with him, and told him I had the time of my life. He asked me if I’d be interested in joining them again.
By now of course I’d realised she was very open minded, actually I should have said both she and John were.
The idea was very intriguing, and then John continued: “We have others who enjoy some special ‘get togethers,’ “You would also be most welcome to join us, when we attend functions hosted by other people.”
Before I had a chance to answer, he went on to say, “It will give you an opportunity to meet other influential people.”
Now that intrigued me as I said before, I loved hob knobbing with the upper classes. I decided to keep my mouth shut and find out more from Lillian, as she was obviously aware about what he was referring to.
As soon as we left and got in her car, I began quizzing Lilly about what John and Nancy were referring to.
She explained that they had orgies on occasion, which involved some very rich and influential people. They knew about my association with Catherine, and of course Mrs. McDonald and now Lillian had some other friends.
She smiled at me and said, “There’s not much they don’t know about you and a few others, they do their homework well before inviting you into their confidence.” And she went on, “You will be meeting some very prominent people.”
We were silent for some time, there were lots of thoughts going through my head. It sounded exciting and alluring, but also very scary.
According to them I was considered to be not only beautiful, but intelligent and could be very discrete.
I arranged to meet with John and Nancy again, at the bar where we’d first met. This time I took Catherine with me, as I wanted them to meet her too. I told him I was interested in his proposition, and that it would have to involve Catherine as well.
“That’s not a problem,” he said, as long as she’s aware of the nature of our get togethers.” He looked at his wife and smiled, “You do realise how important discretion is not just for us, but to the others as well.”
I realised by now they had done their homework on us, but if I was to include others, they would want to find out about them before agreeing to their involvement. I was to learn later how my answers and questioning, reassured them as well.
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