Hired

Constance Sutton is a near neighbour of mine, living a just few doors away and around a corner, but up until my wife left me, running off with great originality with a pizza delivery guy, I'd hardly been aware of her existence and I don't think I'd ever spoken to her once. But then as she was a widow who was knocking on a bit and I was a married man in his twenties that's not really surprising, because we certainly didn't move in the same circles. Not only that, but she was wealthy and I was broke, very broke. I'd taken so much time off work since my wife had gone that my employer had decided to make my absence official and permanent.

But then one afternoon when I was mooching around, wandering past her house with nothing to do except feel sorry for myself, she called me over and asked if I would give her a hand put some boxes into the loft. For a moment I hesitated, wondering if I could actually be bothered to do anything at all, let alone help some old dear tidy her house up.

'I've got some beer if you'd like one afterwards.' She tempted. 'You see, I'm not quite as nimble as I used to be.'

I could well believe she wasn't, looking at her, but it was the prospect of a free cold drink in the heat of summer swung it for me and I did a smart right wheel and set about my good deed of that day, that week even. It wasn't a big job, just half a dozen grocery boxes full of assorted junk that needed stacking in the loft, but the temperature in the roof space was close to cooking and I came down with a hefty shine of sweat on my skin, and that didn't happen very often.

'Good gracious me.' She said, looking astonished at my red face. 'You've really earned that beer, haven't you?'

I smiled to myself at her turn of phrase and followed her into the kitchen, sitting at the big old pine kitchen table and waiting respectfully for my reward. She passed me a towel to wipe the sweat off of my face and disappeared through another door to return a moment or two later with a bottle of beer and a glass.

'I won't join you, if you don't mind. I'm afraid I'm not much of a beer drinker, I only keep it for guests, and in any case I had tea a short while ago.'

I didn't mind, in fact the thought of her drinking beer seemed quietly absurd anyway. I levered the cap from the bottle with my teeth and poured the lovely amber liquid into the glass.

'Oh, I'm so sorry.' Her hand flew to her mouth. 'I completely forgot to bring the bottle opener.'

'It's no problem.' I assured her, taking a long swallow of beer. 'I'm used to doing it like that.'

'Oh, you young people.' She waved a dismissive hand in my direction and then, perhaps realising just how clichéd that must have sounded, she burst out laughing at herself, a full blooded, unrestrained laugh that soon had me joining in. When the laughter died away we sat at opposite sides of the kitchen table, she watching me closely as I drank her beer and me studying her in return. It was the first time I'd really taken a look at her as a person, rather than as the elderly lady who lived in the big house around the corner.

The first thing I realised was that she wasn't quite as old as I'd first thought. Because of the old-fashioned and very conservative way she dressed and acted I'd mentally tagged her as somewhere in her seventies or even older, but now I was seeing her close up I could see that she was only mid, maybe late, sixties. She was around five six or so tall, but quite skinny with it, with a shrunken bust and the beginnings of a pot belly, both of which added to the impression of age, although for all that her face carried the remnants of great beauty. She must have been quite a looker in her day, but her day was well in the past now and drooping eyelids and deep lines around her mouth had wiped most of her good looks away. I suddenly realised that she'd had her heyday long before I was even born and before my folks had done more than begin to explore the possibilities. It seemed a shame really, but I suppose it comes to us all. She'd had her hair died blonde and permed within an inch of its life, or otherwise I guess it would have been grey. Slightly darker eyebrows over her clear hazel eyes suggested that it would once have been a kind of mid brown.

'Do you know?' She said suddenly. 'Talking with you makes a very pleasant change from always talking to other old women. This is the first time I've been alone in the company of a man since my husband died, and that's eleven years ago'

'Really?' I said, unsure how to reply to that and wondering if the fact that she obviously felt safe in my company was a compliment or an insult. 'I'm glad.'

I suddenly realised that my reply could have been interpreted as being glad her husband was dead. 'I mean I'm glad you like me being here.'

She laughed again, amused by my embarrassment. 'No need to explain, and I do like you being here.'

That seemed to open the flood gates and all of a sudden she was telling me about her life. At one point she stopped to fetch me another beer, but I think that was only to make sure I didn't run off before she'd finished, otherwise she just carried on, never really giving me the chance to even comment.

It seemed that she had been married to a wealthy and much older businessman who had been the head of his own company. That had meant that, although her life was materially very comfortable, his circle of friends had tended to be of his social standing rather than hers and mainly of his age group too, and so she had lost touch with her childhood friends. It also probably accounted for her very old-fashioned outlook. Now, because he was dead and most of her acquaintances had also either followed suit or become so aged as to be gaga, she had found herself very much on her own. There were maybe half a dozen people that she could count as friends, and they were all around her own age, give or take half a dozen years, and they tended to talk only about who'd died this week and who was likely to go next. She admitted that she had reached the point when the time for starting again and developing a new social circle was passed, but she felt that she was too young yet to just - in her words - curl up and wait for the reaper. She didn't say it, but she was clearly desperately lonely.

I felt sorry for her, but more than that I found myself actually liking the old bat, especially as she displayed a wry sense of humour. I found myself looking on her as a person and not just as a member of the alien species that anyone that much older than me had always seemed to be before. To my own surprise I found myself asking if she would mind if I called again another day for a chat.

'Of course not, I've already said I enjoy your company. But don't expect a beer every time.'

After that admonishment I hardly dare not call again, and so I found myself ringing her bell two or three times as week. And don't get me wrong, I did it willingly because I found I enjoyed her company too. She might have dressed and spoken as if she'd just escaped from the nineteen fifties, but she was actually quite modern in her outlook. To my surprise I found that she was more than comfortable with her computer and she knew her way around her smartphone better than I did mine. I had to do a rapid reappraisal of my assumptions about the older generation. Even so, I still wasn't ready for what she asked me one day about a month after I had first heaved her boxes into the loft. We were in her lounge drinking coffee when she shook off the preoccupied look she had been wearing and looked across as if having made a sudden decision.

'Scott.' She began. 'What do you know about Craigslist personals?'

The genuine answer was not a lot. I'd looked at them a couple of times out of curiosity, but I'd never used them and I hadn't had very good reports from the couple of people I knew who had. They seemed to be a kind of sexual shopping mall for the desperate.

'Why do you ask?' I countered, not quite sure if she knew just what it was.

'If I tell you, can you promise me that this conversation will stay between the two of us?' She asked.

'Of course.' I promised her, puzzled.

'It must, because I'd be so embarrassed if anybody ever knew.' She looked at me hard, and then continued. 'You know that I don't get out much, and so I don't have very many friends?'

It was mainly a rhetorical question, and so I just nodded.

She paused for what seemed like ages. 'The point is that I don't get the chance to meet many men who are... how can I put it... still in working order.'

It took a few seconds, but when I got what she meant my mouth dropped open and my eyes shot wide. Most of my shock was finding out that she was in working - and wanting - order herself.

'I can see you understand.' She smiled dryly. 'Now you know why what we say must stay confidential. I'm sixty-six and women of my age aren't supposed to think about that sort of thing.'

I nodded again.

'But I do think about that sort of thing, and more and more often.' She told me. 'My fires haven't quite gone out yet and to put it bluntly, I need a man. I'm sick of having to induce my own orgasms.'

I almost laughed at her admission of masturbation, only my complete surprise prevented me. I was beginning to see where she was heading though, or so I thought. 'But why Craigslist?'

'Look at me.' She instructed.

I looked. She wasn't that bad. I mean, she was old to me, but for her age she was actually quite well preserved.

'I'm a good bit past my sell-by date and there's no point in denying it.' She shrugged. 'So I'm not going to be able to attract a virile young man into my bed with my looks alone, and I know that too.'

She paused again.

'So if I'm going to get what I'm missing out on, I've decided I'm going to have to pay for it. I've done a little research and Craigslist seems to be the best bet. What do you think?'

I didn't know what to think. It's not the sort of thing you get asked every day.

'You're looking to find a gigolo?' I asked finally, astounded.

'In a nutshell, yes.' She told me, her cheeks turning a light shade of pink. 'I want some enjoyment before it's too late, and I want someone who will give me pleasure without worrying too much about his own, because I'm not in a physical condition to give much in return, and so the best option seems to me to pay someone for it.'

I was still trying to come to terms with the conversation I was having with her. If anyone had told me I would be discussing where such a mature lady could find a cock for hire, I would have laughed them out of town.

'Yes Connie, I can see where you're coming from.' I told her, still attempting to take things seriously. 'But I would have thought that hiring a stranger would be a bit risky. I mean, you could get robbed, or hurt, or pick up something nasty.'

'Or I could carry on wearing batteries out.' She countered. 'It's either take the risk or go without, it seems to me.'

Another pause. I could tell she was not finding this easy. 'So is Craigslist a viable option? Or can you think of anything else?'

'Oh, it'll work.' I replied. 'I mean, people use it for just that purpose. But that doesn't make it entirely safe. As for any alternative, don't you know anyone who might help you out?' Even as I was saying that I realised how stupid it would sound, and how unlikely.

'Well, let me see. Who do I know' She replied sardonically. 'There's the gardener, but he's got a bad back and he's nearly my age anyway. There's the window cleaner, but he's got teenage spots and probably wouldn't know an orgasm from an organ. And there's you. And that's all the men I know.'

There was an absolutely deafening silence while what she had said percolated through our separate brains, and then she looked at me from under her eyebrows as if silently weighing the chances of surviving after saying what she was thinking.

Right up until that point I had not even thought about myself as a candidate, I really hadn't. I mean, how different from my usual preference could any woman be? And in any case, I've always thought that if you took the bra off of any woman over sixty her nipples would be banging on her kneecaps, and that's not an attractive picture. The trouble was that an unexpected twitch in my pants informed me that a certain part of my anatomy was not entirely ruling itself out.

'I'd pay you.' She finally ended the silence. 'I know that you wouldn't want to do it by choice, so I would pay you.'

I shook my head, commonsense trying to persuade my cock to lie down. 'I couldn't. I mean it would spoil our friendship, wouldn't it.'

'I think it's a little too late to worry about that.' She said sorrowfully. 'Just knowing we spoke about it would get in the way now anyway.'

There was another silence. Now I was actually thinking about it, egged on by my rebellious libido. Then she told me what she had in mind, naming quite a generous figure.

'I'd pay you that for just doing it with me, and then a bit more for each time you make me climax.' She could see me wavering. 'If that doesn't sound all that much I must tell you that I'm still multi-orgasmic. I badly need to be brought to a climax, you have no idea how much I miss it.'

Into my mind there immediately jumped a rather disturbing picture of her masturbating with a vibrator. My cock reacted to the image and my brain responded to the prospect of earning much needed money for doing what comes naturally.

'When?' I asked, capitulating. 'Are you thinking of just one time, or more than once?'

I listened to myself in wonder. There I was negotiating terms for going to bed with a much older woman as if it was the most normal thing in the world. It wasn't.

'Let's try it once and see how we get on.' She said, actually smiling with relief. 'But it would be very nice if it could become a regular arrangement.'

'When?' I asked again.

'Not today I'm afraid.' She sounded as though she really meant that. 'I've got Rita calling round soon and it wouldn't due for her to catch us, and I don't want us to have to rush things.'

She stopped and consulted a mental diary, whilst I wondered who Rita was.

'How about Thursday evening? That will give us both the time to prepare ourselves.'

I would certainly need to prepare myself. Thursday was the day after tomorrow, and I would need all of that time to get my head around what I had just committed myself to.

'That would be nice.' I mumbled, still trying to deal with it. 'About seven-thirty.'

'That sounds fine. I'll look forward to seeing you then.'

That was both a statement of fact and my dismissal for that day. I went home with my head in such a whirl that I almost completely ignored a friend who called to me across the street, only vaguely acknowledging his presence when he hollered his complaint at my ignorance. I wasn't much better when I found myself knocking on her door again a couple of days later. By then my libido had calmed down and I had begun to question my decision. Why had I agreed to go to bed with an old woman?

If I'd had the vague idea that she might try and at least look the slightest bit seductive, I was wrong. She answered the door wearing her usual fifties style floral dress and cardigan and hair that looked to have spent the intervening time in curlers. I began to wonder if a difficult job was in fact possible at all, or if my optimistic cock had bitten off more than it could chew. But, in the words of the sage, I needed the money.

'Come in, Scott.' She stood back for me to go past, probably intending to lock the door behind me and prevent my escape. 'Let's have a drink first. Beer or coffee?'

'Coffee please, Connie.' The stimulant effect of caffeine might yet be needed.

We sat facing each other across the kitchen table once more, silently drinking coffee and trying to decipher each others thoughts. I was looking her over, mostly wondering what I was going to find under those outdated clothes, although what she was thinking I had no idea.

'I shan't pay you until afterwards.' She said suddenly. 'Because we don't know how much it will be. But I promise I won't cheat you.'

'That's okay.' I told her, thinking that I couldn't guarantee that I'd actually be able to earn it.' I never thought you would.'

'But I must remind you of the old saying. She who pays the piper calls the tune.' She informed me. 'So I will expect you to do what I want.'

Please God, I thought, don't let her be a closet Dominatrix.

But all I actually said was. 'Of course.'

'Let's go to my bedroom then, if you're ready.'

'As I'll ever be.' I told her, meaning something different to what she probably thought. There was no sign of activity inside my jeans yet. I was just hoping that something living down there hadn't misled me as to its intentions.

Her bedroom was just as I might have expected. It showed a man's influence in the solid dark oak furniture, but it had been softened and feminised by the over use of pink and white in the soft furnishings, and by a collection of teddy bears that sat on the top of a cupboard and gazed out of the window.

'I'm glad they're not watching the bed.' I commented, trying to lighten the moment.

'Yes, but I'm afraid you're not going to be watching anything, are you my little ones.' She addressed them as she went across to close the blinds, keeping the fact that she had a man in her room for once from any neighbours who might possibly care. Mind you, I didn't really want anyone to see who I was with either, but for reasons of pride rather than privacy.

'Shall we undress?' She asked, meaning it as an instruction.

I nodded and turned my back, though why I'm not sure. Maybe it was because I thought she'd prefer it, or maybe it was because I just didn't want to see someone of her age taking their clothes off, or maybe because I was scared I was going to flunk it.

'Turn around, let me have a look at you.' That also meant that I would have to have a look at her.

It must be said that what I saw wasn't as bad as what I had imagined. I suppose everyone my age thinks of everyone her age as being on their last legs, with every inch of skin covered in wrinkles and everything a good fifty percent further south than it ought to be. Yes, of course she showed her years, but even that seemed mostly in the bits that showed, such as her hands or around her neck. Otherwise most of her skin was fairly smooth, just showing a few creases as she moved, and her breasts were far better than the two empty pouches that I'd pictured. They'd sagged a bit, but they were relatively full and firm and her nipples still faced forward. As for the rest of her, well her legs were a bit thin, her stomach was far from flat and with a few assorted lines, but I've enjoyed worse. One thing I did notice was that her bush was a mousy brown, so at least that hadn't gone grey. My cock finally twitched once to say that all was forgiven. It was going to be possible if not easy.

'I must say you look rather good, but I suppose it must be difficult to make love to order.' She added charitably as she surveyed my pitiable erection. 'Never mind, we won't need that at first.' She climbed onto the bed and patted the space beside her. The command was clear.

I climbed on and lay beside her staring at the ceiling, waiting for her to speak and wondering quietly what exactly she wanted me to do first. She said nothing, and then some more nothing, and I eventually turned on my side to look at her to find out why. She heard me move and turned on her side to face me too, still without saying a word. The silence was becoming awkward.

'This is more difficult than I thought.' She said finally.

'There's no rush.' I assured her; certainly I was in no hurry. Normally I would have been reaching out and pulling my partner to me, hands and lips exploring, but two things stopped me. Firstly, she'd already said I had to do as she wanted, which meant not taking the lead, and secondly, I didn't want to take the lead in the first place. I was beginning to wonder again why I'd agreed to do it, although the answer to that was still obvious - an empty wallet.