My 'phone rang and it was Mary Shaw, a much older neighbour who has recently become my first client as a gigolo. (I'm saying gigolo deliberately because the term 'male prostitute' has gay connotations and I'm absolutely straight.) That came about when I accidentally caught her being serviced professionally by another man and I was asked to replace him when he proved to be less than satisfactory. It just so happens that I'm going through a financial rough patch right now and so I was fairly easily persuaded, even though my initial instinct was to say not bloody likely. But as it turned out because both Mary and I found the session so surprisingly enjoyable we decided to make it a regular thing, and that was a very agreeable arrangement as far as my greatly depleted finances were concerned - and my cock wasn't arguing too much either. I'd found myself embarking on a new and unexpected career.
To help me get established she also agreed to recommend me to a couple of her friends, one of whom she was due to introduce to me later that same day, and so when I heard her voice on the 'phone I promptly assumed that was what she was ringing about. I was right, but not in the way I'd hoped.
'Good morning Vincent.' She began, and then promptly made the morning not so good. 'I'm ringing because Diane can't make it today.' My heart promptly sank, I was still broke and I'd been sort of relying on her. 'However she promises she will visit you soon. But I've told my friend Judith about you and she wants to come along instead. Will that be all right?'
'Yes, of course.' I answered, imagining my wallet heaving a big sigh of relief.
'Just to fill you in, Judith is the same age as me, in fact we went to school together, and she's been living on her own ever since her husband died nearly fifteen years ago.' That didn't sound so good, and it got worse. 'She's also very wary of men after a bad time she had with someone not long after being widowed, so she might need a bit of gentle encouragement. Can you handle that?'
'I expect so.' I answered a little uncertainly. 'I'll definitely do my best, thanks for the warning'
I would do my best, although that didn't mean I'd look forward to it. But, I told myself, if my new career meant pleasing difficult older women, then I'd just have to cope with it.
'That's good.' I could almost hear her nodding over the phone. 'I've told her that you're very considerate and understanding, so don't let me down.' She paused, but before I could assure her that I wouldn't she continued. 'I just want Judith to enjoy herself at long last, she deserves it.'
'Okay Mary. I understand.' I didn't, but I'd go along with whatever put cash in my pocket.
'Thank you. We'll be round later then. Goodbye Vincent.'
Mary is something of a contradiction, she can be old-fashioned and rather imperious and yet she can also be open-minded and generous, and very modern in her attitude to sex - and I'm getting to like her as a person. When my doorbell eventually rang I'll admit that I answered it with a certain trepidation. Standing there were Mary and her friend.
'Hello Vincent.' She greeted me. 'I'd like you to meet Judith, can we come in?'
'Of course.' I backed to one side to let them past, taking a look at Judith as they did. She actually looked older than Mary, but then Mary looks comparatively young for her sixty-six years. Judith was tall and slim, almost skinny, with short grey hair that had once been dark, and scared brown eyes under bushy dark brows. Her face was lined with age, her nose was long and thin and she had the beginnings of a wattle. On the plus side though, she stood with poise and walked like a younger woman, and she was extremely well and expensively dressed. I couldn't help but wonder what she would make of my rather humble abode. She gave me a quick nervous little smile and hurried past in Mary's wake. I gave her a warm reassuring grin but I'm not sure she saw it before she looked away. I couldn't help feeling a little worried about how things would go.
'Would you like a coffee?' I asked the two ladies who had sat themselves side by side on my sofa.
'Not for me thanks.' Mary replied. 'I can't stop, but I'm sure Judith would appreciate one.'
I looked at Judith, who nodded quickly. 'Black, please.'
I came back with two coffees, one for me and one for Judith, which I placed on a little table beside her.
'Are you sure you wouldn't like one?' I asked Mary, more out of politeness than expectation.
'Thank you Vincent, but no. I just want to introduce you and Judith to each other as she may want to avail herself of your services, and I can't stay anyway - it wouldn't be appropriate.'
I do like the way Mary speaks, so prim and proper, and exactly the opposite to how she is in the bedroom.
'I'll leave you two to discuss things; Judith wants to be sure you are suitable.' She got up to leave and I escorted her to the door where she added quietly. 'And take good care of her because she's an extremely good friend of mine.'
'Don't worry, I will.' I assured her, and then closed the door wondering what I'd let myself in for.
I returned to the living room and sat down. 'Hello Judith.' I said with a grin. 'I know Mary always calls me Vincent, but I'd prefer Vince if you're comfortable with that?' I don't really care, but it was my way of starting a conversation.
She nodded, a quick jerk of the head. 'Vince it will be.'
We lapsed into silence again as we each drank from our coffees to fill the void, then suddenly she turned to me as if having made up her mind.
'You must understand that I'm way out of my comfort zone with this, but don't worry, I'm not going to back out.' Her voice was unexpectedly firm and melodious now that she'd started. 'However, there are a couple of things you need to know and they might make everything impossible, and so I'm going to tell you now before we get too involved and while I've still got the nerve. '
'Go on?' I encouraged her, guessing that one of the things might be her off-putting earlier experience. 'Very little would make everything impossible.'
Through my mind flitted the thought that her scrawny body might just be one, but obviously I couldn't say so. I just hoped my cock could rise to the occasion.
She paused, fidgeting with embarrassment. 'Firstly, let me explain that when I went through the menopause it had the effect of making me dry down there.' She pointed a finger in a vague downwards direction before digging into her bag. 'And so we're going to need this.'
'This' turned out to be small bottle of sex lubricant which she placed on the table alongside her coffee cup. That was something I hadn't expected and I think my eyebrows shot upwards in surprise. I'd never even thought of the possible effects of menopause, it wasn't on the radar for women of my generation yet. But I didn't see it as a barrier.
'Well that's not going to be a problem then.' I told her with a smile.
'Yes, well that has a direct connection to the second thing.' Now she sat and almost visibly squirmed.
'And that is?' I prompted, adding quickly. 'And don't worry; I shan't ever say anything to anyone, including Mary.'
'Mary knows.'
I guessed this was going to be the bad experience she was talking about.
'Okay.' She drew a deep breath and plunged on. 'When I began to need extra lubrication it put my husband off sex, even though we'd had a very active love life up until then, and so I went without it for several years before he died, and I missed it badly. Don't misunderstand me, I don't mean you to think that I was glad he was gone, I really wasn't, I missed him awfully. But after a while I thought to begin a physical relationship with someone else.'
Again a pause.
'Well to cut a long story short, I made a date with a man and then took him home with me at the end of the evening. We went to bed and he positioned himself behind me because he told me he liked to do it that way, as I frequently did too. He seemed to understand my need for lubrication and so before we started he applied the lubricant to us both, but then he pushed himself into the wrong place - and it hurt. He wouldn't stop either, even when I wanted him to. He just pinned me face down to the bed and carried on until he'd finished.'
I wanted to say some words of sympathy, genuine words of sympathy because forced anal sex must be dreadful, but I figured it would be better to just let her continue.
She took another deep breath. 'Obviously, that was it between us as far as I was concerned, but he wouldn't let it go. He kept phoning me and saying dirty things down the phone, or writing suggestive notes and putting them through my door, or even sitting outside my house in his car for hours on end. Eventually I called the police and they cautioned him, but he still kept on harassing me and it then took a male friend to warn him that things could become violent before he finally got the message. You must understand that the experience has left me frightened of getting too close to another man, and so that's why I've come to you. You see, we'll never be romantically involved, you'll never know anything about me, not my second name, not my address, not my phone number or anything else, and that way I know when I walk out of your door you can't trouble me. And if that sounds unkind then I'm sorry, but it's the only way I can have a sex life before I'm too old.'
'I understand and I'm truly sorry a man put you through that, but why should that make things impossible today?'
'Because I don't know how I'll react when we get down to it.'
'I understand.' I did, sort of. 'We'll have to wait and see then.'
'Can it be today? Now?' She asked suddenly. 'I mean, do I need to make another appointment?'
'No, as it happens I'm free.' The question caught me by surprise, I'd kind of assumed she'd meant there and then anyway.
'Good, I'm not sure my nerves would cope with having to call back.'
I nodded. 'I can see that. So shall we go upstairs?'
I know that's not the most seductive way to get a lady into my bed, but I am supposed to be running a business after all. In any case Judith didn't seem to mind for she meekly followed me up the stairs without another word, picking up her bottle of lube as she came. I called in at the bathroom on the way past to pick up a towel and then ushered her through to my bedroom.
She put the lube on my bedside table and then immediately began undress with her back to me, neatly laying her clothes on an old easy chair I keep in the bedroom for when I can't sleep. As she undressed I stripped off behind her, watching her as her clothes came off. She was very thin, her legs were skinny and her buttocks bony, and her body was showing its years even from the back view. Nevertheless some of the beauty that she had once been was still in evidence, and my cock was responding as if an eighteen year old was standing there. But then it knew the state of my finances.
As soon as she was naked she stood there very stiffly for a minute, still facing away, and then hiding her breasts and pubes with her hands she turned around. For a few moments she stood like that, covering her vital bits and staring at my erect cock, and then very deliberately she let her hands drop to her sides, consciously revealing herself to me.
