Discreet Encounters - Beginnings

'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.

*****

'I hope they're what you wanted'. The female assistant behind the counter passed me one of the boxes of my newly printed business cards and looked at me, awaiting confirmation. The printer had indeed made a tasteful job of them.

'They're exactly what I wanted. Thank you.'

'May I keep a couple?' the girl asked as she took my credit card to settle the bill. 'You never know when they might come in handy.'

I hadn't really taken much note of her until that point. I suppose she was around 40 and apparently unattached - or at least she wore no ring to signify attachment. Her silvery-blond hair was tied back out of the way and she looked at me through gorgeous brown eyes. Beneath her t-shirt, a decent-sized pair of breasts thrust the company's name and logo in my direction while, hidden beneath the counter, she wore a pair of jeans that fitted her trim figure well. I found myself thinking that I wouldn't object if my card came in handy for her one day, though I wondered if she could afford the kind of fees I had in mind.

'Of course', I replied.

She took half a dozen and slipped them beneath the counter.

'I can always call you if I need more.'

'Please do', I assured her.

*****

I was single, I thoroughly enjoyed sex, and I'd had a stream of girlfriends who'd seemed satisfied enough to come back for more - and a few, mostly married ones, who'd even recommended me to their friends.

I'd also been made redundant and, while I was still a long way from starvation, my redundancy pay wouldn't last forever. I would eventually need an income. The trouble was that my line of work was in decline and there were a lot of people competing for a shrinking number of jobs. Changing career was the obvious thing to do but what new field was open to me?

It was Caroline who set me thinking about it in a way I hadn't expected.

'What are you really good at?' she asked as we lay in my bed enjoying a spot of post-coital relaxation - she was ostensibly out visiting clients, at least that's what her boss and her husband both thought. She ran her hand down between my legs as if to answer her own question.

We discussed the idea while she stroked me back to a full erection. I wasn't sure whether it was our discussion that encouraged my arousal or whether her actions made the idea sound so appealing.

There were, she reminded me, a lot of married women who were less than satisfied with the sexual side of their marriages. She reeled off a list of names of her female friends whose husbands regularly devoted long hours to demanding careers and were simply too tired to perform. A few of the women knew that their husbands had mistresses - they were aware that it needed the excitement of an illicit encounter to arouse their jaded husbands. They chose to turn a blind eye but some of them wondered whether what was good for the gander might not also be good for the goose. A discreet, no-strings-attached service might be just what they needed.

I wasn't sure it made for a realistic business proposition. Why couldn't they simply have an affair themselves? Over the past few years, I'd fucked quite a few less than happily married women for free. Why on earth would they want to pay me to do it?

Caroline laughed.

'Darling, you might have given them all a good fucking but how well do you think you've really got to know them and why do you think they come to you rather than anyone else?'

'I don't know. I assume they think I'm a good lover.'

'It's far more than that', she replied. My cock was now completely rigid and she indicated that I should get on top of her and enter her again. I slid easily into her cunt, still wet from our earlier fucking session.

'Mmmm, that's nice', she said. 'I thought it might help to add a spot of focus to our discussion if we fucked while we talked.'

She paused for a moment while I settled into a slow steady rhythm which her body adjusted to accommodate.

'For a start, these women aren't going to do anything that might rock their marriages. Even husbands with mistresses have been known to leave their wives because they've begun their own affairs. It's not fair, but that's the way it works. You can promise yourselves all you like at the start of an affair that it won't get serious or messy or get found out but there's no guarantee it won't go wrong and in lots of cases it does. Believe me, you only have to watch a couple of marriages founder because of a bit of indiscreet adultery to feel the risks weighing heavily on you. With you, it's different. You're totally discreet and there's no question of us getting into an involved relationship. No furtive phone calls to be overheard, no loving text messages for someone to find, none of that. You respect my situation and you won't do anything to upset it. I know that when I need a really good fucking, I can come to you and get it, and then go back to my real life. To be honest, if you weren't around, I'd willing pay someone to fill the gap, as it were.'

It seemed almost unreal to be talking in such a matter of fact way as my cock explored the depths of her cunt, though it was highly erotic too. Caroline knew full well that at least half my thoughts were on those other women I might fuck as on the gap I was filling at that very moment.

Of course, Caroline went on, not all of those women would be up for full sex but I could always offer massages with the optional extra of a happy ending. A relaxing massage was hardly the same as taking a lover or having an affair, was it?

Other women - she reeled off another list of names - had chosen to focus on their own careers. Demanding husbands - even boyfriends - didn't always fit comfortably with their ambitions and lifestyle but that didn't mean they'd lost all desire for male company, provided that it came without commitments.

All of these women had money - or their husbands did. That wasn't a problem but absolute discretion had to be assured and a cast-iron guarantee given that no strings would be attached. A quiet, personal recommendation would be eminently helpful too. Fortunately, I was at an age at which I could just as comfortably entertain a woman ten or fifteen years my junior as I could one ten or fifteen years older. It was a case of appropriate dressing and grooming to look the part. Caroline was sure she could find me half a dozen clients and if each of them could do the same...

She had me convinced.

She looked me straight in the eye as I continued to penetrate her. 'I wonder which of them you're thinking about while you're fucking me', she murmured in my ear. 'I think you're really enjoying the prospect of this, aren't you? And I wonder what naughty things some of them might want you to do to them? Or vice-versa?'

That became too much for me as my imagination began to consider the possibilities. I pushed faster, harder, and deeper into Caroline's cunt and she began to gasp and moan with the shared excitement. 'Oh yes, think of all those women you're going to be fucking, all the nipples and clits you're going to play with, all the wet cunts you're going to open up. Fuck me like you're going to fuck all of them.'

If anything, the thought of all this was exciting her even more than it was exciting me. I could tell by the wetness that was pouring out of her and covering my cock what it was doing to her. I had absolutely no objection to this; not only was it making for a very good fuck then and there but it would also encourage Caroline to line me up with a steady supply of clients who she could imagine giving up their bodies to me.

I felt her hand slip between up and she began to rub her clit with a fury I'd never seen in her before.

'Fuck her, oh fuck her, fuck her harder than she's ever been fucked before. Make her cum all over your cock.'

I had no idea who Caroline imagined I was fucking but the thought of it was driving her to a massive climax. She started letting out deep grunts and, with the muscles of her cunt gripping my cock like a vice, I knew it could only be a matter of seconds before we both erupted. Then her whole body tensed and arched, lifting me as if I was a feather.

'Oh fuckkkkk!', she yelled, as I forced my cock as deeply inside her as I could, and poured my cum into her.

*****

Later that afternoon, after we'd both recovered, we worked out the figures - how much would I have to charge for an afternoon, an evening, a weekend away. It felt strange to be sitting down and working out a business plan for fucking women but it was clear from the start that I had to think of this as a business, even if it would turn out to be a most enjoyable one.

My flat would be fine for some encounters but the second bedroom needed to be redecorated and furnished to be suitable for trysts. A decent hotel would be an added extra for those who preferred that alternative - if I concentrated my patronage on just a couple I would become a known guest and, if I kept them generously tipped, the staff might even pass on recommendations to potential clients.

We eventually chose three hotels that would suit my needs. One was in Central London and was mostly frequented by foreign tourists. It was small, discreet, and well away from the business heart of the City where many of my likely clients' husbands worked. The other two were in anonymous but handily-located towns beyond the outskirts of London; no matter where my clients lived, at least one of the two would be far enough away from her home for the risk of bumping into a friend or neighbour to be minimal.

I would need to set up an arrangement to take credit cards using a business name that could appear on statements without arousing suspicion.

We made out a shopping list of the clothes I would need and the establishments from which I should buy them. It was as well I'd just banked a large redundancy cheque - tailored clothes and handmade shoes don't come cheap.

I decided to buy both a massage table and a portable massage chair, the type in which the client normally sits reversed, with the chest against the seat's back, the knees and arms resting on side supports, and the face resting on a cradle. Such a chair offered a lot of advantages. Being portable, I would be able to take it to clients' homes or hotels. In addition, a shy client could be completely naked and I could massage her shoulders, back and behind without her breasts and sex being on display. Of course, once she relaxed and felt more at ease with the situation, she could turn around and her body would be completely accessible to my attentions.

*****

I needed a dummy run. I was going to be having sex with women who would be paying good money for my services. That meant being totally professional whereas, up till then I'd only been an amateur, albeit an enthusiastic and fairly competent one. Needless to say, I couldn't practice on anyone I knew - it wouldn't be realistic - but Caroline thought she knew just the right person.

Felicity was married but her husband was continually away on business from Sunday night to the following Friday. He was usually too tired for sex at the weekend, though he seemed to have enough time for socialising and drinking. She was screamingly frustrated but she was terrified that an affair with anyone she knew would come to light sooner rather than later and end in a disastrous divorce. And, after the Ashley Madison fiasco, she had no intention of adding her details to any easily-hacked database. Besides which, as she'd confided to Caroline, she'd never been unfaithful to her husband.

She would be an excellent test of my ability to manage things with total discretion and to perform where it mattered with a previously unknown partner. Caroline promised to get in touch with her.

In the meantime, Caroline put me through my paces herself - to 'get rid of the rough edges', as she put it. My confidence began to take a bit of a battering when she pointed out just how many rough edges there were.

We discussed the possibility of my using Viagra. A lot of clients would expect me to take them more than once - possibly a lot more than once - and, as Caroline pointed out, I would be remarkably lucky if every single client aroused me sexually. In some cases, it would have to be a matter of 'lie back and think of England'. On the other hand, most women would probably rather imagine it was their allure that produced my erection, not a little blue tablet and the spell might be broken if I remained permanently erect.

In the end, we decided I should keep some Cialis handy - they were fairly quick acting and weren't affected by food, so I could easily pop one if the need arose.

Caroline's next stricture was to 'watch the drinking'. The last thing I would need would be a spot of brewer's droop just as I needed to perform. And, of course, some women might be put off by the smell or taste of alcohol when we kissed.

No drinking wasn't really feasible but there were things I could do. If I took a woman out to dinner before heading to bed, I was to let her drink most of the wine. When she disappeared to the toilet, I should take the opportunity to top my glass up with a dash or two of water. When we got back to my flat, I should offer her a drink and, if she accepted, rather than leave her to drink alone, I was to pour myself a gin and tonic that was almost entirely tonic.

Undressing was the next lesson - both the client and myself. Caroline turned up at my flat one day with a bulging suitcase. Fortunately, her husband was away or he'd have wondered if she was moving out; her wardrobe must have been half empty. She spent the whole day changing from outfit into outfit so that I could practice removing them until I had the moves perfect and the clothes fell off her, seemingly without effort.

Undressing myself would be far easier because I could control what I was wearing - or so I thought. It didn't take Caroline long to disabuse me of that notion. She had me undress in front of her and, unkindly, videoed the performance. When it was over, she let me watch myself looking ridiculous. The worst bit was of me hopping about on one foot, trying to get my trousers off.

The Chippendales, of course, use Velcro-fastened clothes but that wasn't an option for me so Caroline taught me how to get out of my clothes in an elegant way without resorting to such dodges.

Next, we turned to grooming. Some women adore the rugged style - calloused hands, bristles, the undisguised smell of sweat, even oily fingernails - but many of my prospective clients were likely to be turned off by such things. It became a matter of balance - manly but not cavemanly. We debated long and hard about whether I should shave down below or even be waxed. In the end, we decided that, since many of my clients were likely to be approaching middle age - at the very least - a totally bald cock and balls wouldn't be appropriate and a few might even think it pervy. We therefore decided that a tidy trim fitted the bill.

Caroline set up appointments with manicurists, pedicurists, and barbers and gave them all very precise instructions.

*****

It took Caroline longer than we hoped to get hold of Felicity - Fliss as she was known to her friends - and then she took some convincing. Exactly how Caroline broached the idea with her I cannot imagine; fortunately, it intrigued and excited her but she was full of 'what-ifs'. What if she went to a hotel and someone recognised her? What if her husband came back at the wrong moment? She had clearly been thinking about the possibility of an affair in quite some detail and had considered all the potential problems.

It took Caroline a while to sort out the arrangements in a way that would minimise Fliss's fears. The cover story was to be that Fliss and Caroline were spending a couple of nights in London, taking in a show or two. On the second night, all three of us would have a meal together; if anyone saw us I could be explained away as Caroline's friend. Then, with the meal over, Fliss was to come back to my flat while Caroline would return to the hotel alone. Fliss's mobile phone would be turned off overnight - her excuse would be that she'd turned it off during one of the shows and had simply forgotten to turn it back on again.

*****

When everything was finally arranged and the day arrived, I met Caroline and Fliss at their hotel in London. From there we went to an excellent restaurant not far from my flat. It was relatively unknown, it offered good, unpretentious food, and it was possible to get a table at short notice without being an A-list celebrity.

Fliss is an incredibly attractive lady; there is no doubt about that. If she'd not been so terrified of wrecking her marriage she could easily have had a whole string of attentive lovers. From the moment I saw her, I wanted her - to the point at which I might have felt guilty if she'd been a paying customer. She had lustrous, shoulder-length auburn hair, which set off her hazel eyes to perfection. Her breasts were full and I could imagine them weighing heavily in my hands. For her age - she'd apparently not long passed 45 - she had a very good body with an hour-glass figure. Caroline said that she spent a fair bit of time at the gym.

The meal went well. Fliss seemed quite shy - or perhaps she was subdued by the thought of what was to happen later that evening - but we hit it off very well and there was more than a spark between us. I could tell that Caroline was relieved, which was a good sign. Having brought us together, she must have felt anxious that the evening should have the best possible outcome.

Standing outside the restaurant after the meal, Caroline put her arms round me and kissed me on the lips. 'Take care of her', she whispered in my ear. 'I'm sure you're both going to have a good time.' Then she turned to Fliss and kissed her on both cheeks. 'Have fun', she said to her. 'I'm sure he'll be very good for you.'

While Caroline took a taxi back to her hotel, Fliss and I walked the short distance to my flat. I opened the front door and ushered her in and guided her to the lounge. I'd left the lights on low with music playing softly in the background to set the right atmosphere and now I offered her a drink; she decided on a white wine. I went through into the kitchen to pour our drinks and returned with her wine and my 'gin and tonic'.

Fliss and I chatted for a while but then she needed to go to the bathroom. I was standing in the middle of the room when she returned and I took her in my arms.

'Are you ok?' I asked.

'I'm nervous', she said. 'I know that a lot of your girlfriends are very attractive and sexy - like Caroline. I feel like a middle-aged frump and I'm worried you're going to be disappointed. I'm probably not very good in bed and maybe that's why my husband - she didn't seem to want to refer to him by name - never wants to make love to me.'

I kissed her. 'You are most definitely not a frump - you're a fantastically attractive woman and I'm very lucky to have you here. It's up to me to make you feel good in bed - and talking of bed, I think it's time...'

I took her hand and led her gently out of the lounge and into the bedroom.

'It's lovely of you to say nice things about me', she said, 'but I really am nothing special to look at. Couldn't you just pop outside so that I can get undressed and get into bed first?'

'Absolutely not! Are you really going to deprive me of the delight of slipping your clothes off and slowly revealing your beautiful body? All evening I've been looking forward to seeing you naked.' She cast her eyes downwards. I put a finger under her chin and raised her face towards me, forcing our eyes to meet. 'I want you, I want you so much.'