Discreet Encounters – Charlotte

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Another short tale in the Discreet Encounters series.

‘Discreet Encounters’ the card stated in an elegant typeface. ‘For those times when a woman needs a man for company’. My forename and a mobile telephone number completed the message and a silhouette of an embracing couple made sure there could be no misunderstanding of its meaning.

Redundancy had led me to seek a new career. It was my occasional lover Caroline who had suggested that maybe I should exploit something that she thought I was rather good at. After a trial run with Caroline’s friend Fliss, it was time for business and my first real client.

The phone rang and it was Fliss on the other end. At first, I assumed she’d called to make an appointment for herself but she quickly made it clear that not only was she calling for a friend but her request was also a rather unusual one.

Charlotte was, according to Fliss, a considerably reserved girl as far as relationships with men were concerned. Now she had been invited for a wonderful evening out with a group of friends but, with no-one to accompany her, she was proposing to decline the invitation. Fliss wondered whether I would partner her. There would be no sex involved but Fliss was prepared to pay my normal fee for the evening.

I was happy to oblige but I suggested to Fliss that it would be an idea if Charlotte and I met before we agreed on anything. It might be awkward if the first time we met was on the evening of the event and we found that we couldn’t stand each other. Fliss agreed and said that she would arrange for the three of us to get together over lunch one day.

Charlotte turned out to be a very attractive woman. She was somewhere in her late 30s or early 40s, with neck-length hair that was such a dark shade of brown as to be almost black, eyes that matched her hair in colour, an appealing full-rounded bust, and a pleasantly curvaceous figure.

The lunch went very well. We clearly had enough views and interests in common to give us at least the basis for some conversation and we hit it off well enough. We agreed that she would accept the invitation for herself and partner.

The evening started with a concert at the Royal Albert Hall. The host obviously had contacts because not only was the concert an immediate sell-out but he had managed to arrange a box for the party. The concert was followed by a late supper at a very pleasant bistro nearby. Charlotte’s shyness with men was obviously widely known and there were a few surprised looks when I arrived with her. Needless to say, I faced quite a few questions and, to avoid any embarrassment to Charlotte, I had to be careful not to reveal my true role in answering them. I simply introduced myself as having met Charlotte through a mutual friend just around the time she had received the invitation for the evening. I left it unsaid – but in a way that let it be understood – that our mutual friend had paired us up for the occasion and that not too much should be made of it in the sense of long-term prospects. Fortunately, all those present knew Charlotte well enough to realise that matchmaking would be a waste of time but there did seem to be some pleased and hopeful looks on a couple of faces.

The evening was wonderfully relaxed and convivial. I’m sure that Charlotte was a little tense at the start of it but by the end, the mood had embraced her and she seemed to be thoroughly enjoying herself. She had even become quite tactile, at least to the extent of resting her hand on my arm from time to time and, on one occasion, even on my knee. I couldn’t help notice, too, that her bright, dark eyes lingered on mine to an unexpected extent.

When the meal and the evening finally came to an end, we grabbed a taxi and I gave the driver Charlotte’s address. As the cab turned the corner into her road, Charlotte turned to me.

‘The very least I can do is to invite you in for coffee or a drink.’

The house was cosy without being cluttered. Charlotte made the coffee and brought it through to the lounge but then she excused herself and left the room. I picked up a magazine from the coffee table sınırsız escort and began to flick through it. A couple of minutes later a movement in the doorway caught my attention. I looked across and Charlotte was standing there, wearing just a nightdress. The top part was made of lace, through which her firm breasts, surmounted by dark nipples, were clearly visible. The rest of the nightdress was of purple satin that clung to her in such a way that suggested she had nothing on beneath it.

I didn’t know what to think. Was she aware of the arrangement between Fliss and me – that I had been paid to escort her to the concert? I was sure that Fliss would have explained things, but maybe she hadn’t made it clear. Did Charlotte think I hoped for a relationship with her?

‘Charlotte’, I started tentatively, not wanting to upset her, ‘didn’t Fliss explain…?’

‘Oh yes, you’re a professional escort and Fliss paid for your services this evening. I know.’

She walked across the room and perched on the edge of the sofa next to me. She reached out with her hand and placed it on top of mine.

‘I’m a virgin’, she said, looking me straight in the eye, ‘and I don’t want to be any more.’ I must have looked quizzical because, after pausing briefly, she went on. ‘My parents had a dreadful relationship and that put me off any thought of getting involved with someone. I had a few boyfriends when I was younger but I found I was constantly watching for the slightest sign that things were going wrong. It always put a damper on anything further developing. One boyfriend actually told me he felt he was on trial the whole time he was with me and he couldn’t take it. It’s not that I don’t want sex – I really do – but I’ve always assumed that sex might lead on into a relationship that I wouldn’t be able to cope with.’

‘And, presumably, it would be different with me because there’s no question of a relationship?’

She nodded. ‘That’s what I understood from Fliss. Please don’t be annoyed with her but she told me a bit about you and her and your arrangement. I promise I won’t tell anyone.’

She paused, a look of slight awkwardness coming over her face.

‘I’d better mention it, in case you wonder’, she added. ‘I’m not really a virgin, not in the physical sense, anyway. I have a few toys. As I say, it’s not that I don’t like sex. And, just to add to my embarrassment, I’ve been getting very wet all evening in your presence so would you mind very much if we abandoned the coffee and went straight to bed? I’m not sure that a toy will give me what I need at this moment.’

I stood up, took her by the hand and drew her close to me.

‘I hope you’ve no objection to kissing’, I asked her softly.

‘None at all’, she replied with a deep smile.

Our lips met and our tongues began to explore each other’s mouths. She was surprisingly adept at it considering that it can’t have been something she regularly practised.

She must have realised what I was thinking because she felt the need to explain.

‘It just seemed to come naturally – you’ve made me so relaxed. But now I have a problem’, she added. ‘I’m getting so wet it’s starting to run down the inside of my legs. Please, can we go to the bedroom? Right now?’

I let her lead me by the hand up the stairs and into her room. The lights were set low and it looked very inviting – she had already turned down the corner of the duvet. I turned her to face me and then began to remove my clothes, purposefully but not too hurriedly, remembering all the tutoring I’d been given by my mentor Caroline. By the time I was down to my underpants my cock was decidedly erect and I had some difficulty extracting it before I could stand naked in front of Charlotte.

‘I’m glad I’ve practised with my toys’, she said, her gaze fixed down below my waist.

I moved towards her and slipped the nightdress off her shoulders. It fell to the floor and she stepped away from it. As I had surmised, she had nothing on beneath it. A naturally small patch of dark pubic hair covered her prominent mound but did nothing taksim escort to hide the slit that ran up its centre. I imagined that it would normally have been tightly closed but her passion had caused the outer lips to part and, as she had revealed, the gap between was extremely wet.

I moved very close to her, taking her into my arms and allowing my hard cock to press against her sex. She gasped as she felt it touch her. It was hardly penetrating her – though it wouldn’t have taken much for me to enter her – but the feel of the tip of it resting there took her by surprise. We kissed again and I took one of her breasts in my hand, caressing her nipple.

Suddenly, she pushed me back onto the bed and, without more ado, swung her leg over my thighs, took hold of my cock, and lined it up with her now open and waiting hole. She sank down on me and I found myself surrounded to the full length of my cock. She let out a long loud groan as our pubic mounds collided and her head fell forward so that her hair virtually masked her face.

‘At last!’ she gasped. ‘Oh god, why did I wait so long for this?’

All of this was rather unexpected. I had fondly imagined that her first experience would begin with my tongue exploring her slit and clit to arouse her, followed by sucking up some of her copious juices, and concluding with me entering her for the first time in the more conventional missionary position.

Once again, she seemed to be aware of what I must be thinking.

‘I’ve watched porn’, she explained. ‘Women seem to love being in this position and I couldn’t wait to try it.’

I had absolutely no objection, especially as she seemed to be riding me very expertly. I reached out with one hand to take her breast and slipped the other between her legs, feeling for her clit. She clamped her hand on top of mine and demonstrated how I should produce the effect for which she craved. She was very soon pounding herself on my cock and groaning with pleasure as my fingers, under her firm direction, teased her clit. Within moments, a climax overwhelmed her. She threw her head backwards and let out one very long moan as it took her over.

‘Oh my god,’ she gasped, ‘I can’t believe it.’

I was nowhere near ready to cum – I always seem to take much longer in the woman on top position – but fortunately, she was far from finished. After a few moments she flopped forwards, propped up on her arms, but then she clambered off me, letting my still-erect cock slip out of her, and turned onto all fours.

‘Do me from behind’, she demanded.

I hastily got up and knelt behind her. Her cunt was still gaping open and I fed myself straight into her. She pressed back, forcing me into the depths of her. I was afraid that penetrating her that deeply might be uncomfortable for her, but she showed no signs of it.

‘Fuck me hard, make me cum again.’

I felt her hand move down between her legs, so that she could feel her lips spread around my cock where it entered her, while simultaneously working her fingers on her clit.

‘Take my tits in your hands.’

This woman may not have been experienced but she knew exactly what she wanted. I reached under her and took her two good rounded handfuls in my palms.

‘Stretch my nipples’, she insisted. ‘Pull them hard.’

I obliged, while slamming into her from behind, each of my thrusts being matched by a forceful push back of her buttocks. If she kept this up I was unlikely to last very long and I found myself hoping that she wasn’t far off cumming. Fortunately, my prayers were answered and she started to let out a series of grunts that heralded the onset of her climax. The hand between her legs was going at a furious pace and I added to the effect by squeezing and pulling hard on her nipples. It was more than enough. As I began pouring my sperm out into her, she collapsed forward onto the bed, spent.

I released her breasts and took hold of her hips, drawing her back onto me until every last drop of my cum had spurted out into her womb. A virgin she might have been, but I had just experienced tesettürlü escort one of the most vigorous bouts of sex I’d had in a long while. She reached back and I felt her fingers surround my cock. She ran them all around it and down to my balls before moving up to the point where we were still very wetly joined. I could feel her juices, mixed with my cum, oozing out around my cock.

When we finally separated, I thought she might suggest that we have a shower – we were both very hot and sticky – but she made it plain that she wanted to stay as we were. No toy made her feel like that, she explained, and she wanted to savour it. And, in any case, there was no point in cleaning ourselves up when we were going to get hot and sticky again in the morning.

It was only as I drifted off to sleep that I realised I was only being paid for an evening but, what the hell.

I woke the next morning to the sensation of a warm, wet mouth engulfing my cock, bringing it to full erection. She smiled at me as I opened my eyes, seeking signs of my approval.

‘My dildo never tells me if I’m doing this right.’

‘It must be enjoying it too much to speak’, I assured her.

I couldn’t imagine that she was going to let me cum in her mouth. I knew exactly where she wanted my cock to be and I was right. She turned to face my feet and got on top of me again, slipping down onto me very readily. As she leant forward, I could see myself vanishing up inside her, a view I can never get enough of, and as she rose up and down, my cock steadily became coated with her wetness.

‘Feel me opening around you’, she instructed me.

I felt around the place where we met, exploring her stretched little lips. My fingers were soon soaked and thoroughly lubricated for what she had in mind next..

‘Put one of them in my behind.’

Her buttocks were spread wide as she straddled me and her anal rosebud was there, revealed, for the taking. I eased a finger in. She seemed well practised at handling the intrusion – no doubt one of her toys had passed this way before – and the full length of my finger was soon inside her. I began to do what no toy could really do and began to flex my finger around inside her, exploring the walls of her anus, feeling my cock moving in and out of her on the other side of the thin membrane in between. Once more, her hand had moved down between her legs and was furiously stimulating her clit. Gasps, grunts, moans and groans were spilling out of her in seemingly endless variation and combination. I slid my finger out of her behind, which seemed to cause her consternation, but then I replaced it with two. She let out a little squeal as I stretched the opening wider but then she pushed backwards, forcing my fingers into her.

I could hardly believe what was happening. I thought back to the call I’d had from Fliss, introducing me to this woman, and wondered if she really knew very much about her.

‘Fuck me, fucking make me cum’, she yelled out. ‘I need to cum again.’

I forced my cock up into her as she bounced up and down on me. Her hand continued its frenzied attack on her clit and my fingers probed deeply into her anus. There wasn’t a lot more I could do to bring on her orgasm but no more was needed. It came quickly, bursting over her, causing her whole body to tense and shudder. Her cunt muscles tightened around me, gripping my cock, forcing a sudden, unexpected, and ferocious climax out of me.

The result was that the two of us were shattered. She propped herself up on her arms as best she good and sat there on top of me, heaving and gasping for breath. Not a word passed between us for several minutes but then, eventually, she got up off me, turned round, and kissed me.

‘Not bad for a first time,’ she said, ‘but I think I’d better have your phone number. I might be needing you again.’


Later that afternoon, the phone rang. It was Fliss.

‘How did the evening go?’ she asked. ‘I was really worried for you. I hope that you and Charlotte got on alright. She can be so terribly reserved sometimes, it can be very awkward.’

‘Oh no,’ I reassured her, ‘reserved was the very last thing she was.’

There was a pause.

‘You’re not telling me that you…’

‘You can take it that I am and, what’s more, you owe me quite a lot of overtime pay.’

All I heard was a peal of laughter as she put the phone down.

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