My New Career - Judith

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.

'Saggy tits, a wrinkly belly and spindly legs.' She announced bluntly. 'Can't be the nicest prospect to have sex with.'

It must be said that her self-deprecating remark was pretty much on the money, but for all that she was still very feminine and strangely attractive in a shy sort of way. My cock certainly thought so.

'Judith.' I told her. 'There may be women more beautiful, but few as attractive.'

I hoped she would recognize the tribute, and it wasn't far from the truth. A woman doesn't have to be gorgeous to be desirable. I think she understood, for she visibly blushed, although of course it might have been that she thought it was all part of my sales pitch.

She shot a look at my rigid cock and went to stretch out on my bed. 'Shall we do it then?'

I nodded and smiled, climbing onto the bed alongside her, intending to indulge in a little foreplay.

She opened her legs wide and indicated for me to be between them. 'No, just do it,'

She was the boss; I moved to pick up the bottle of lube and then knelt between her legs, gazing down at her hairy pussy.

'Ready?' I'm good at silly questions when I'm nervous.

She nodded without speaking and looked meaningfully at the lubricant. I squirted a little onto my fingers and then reached forward, seeing her suddenly tense as my hand got closer.

'Relax.' I told her. 'Everything will be fine. We're both going to enjoy this.'

She nodded again and closed her eyes, waiting for me to touch her.

'You look lovely.' I told her quietly, exaggerating only a little. Her eyes remained closed but a quick smile flitted across her face.

Lube is always cold when it goes on and I like to think her quick little gasp was for that rather than from apprehension. As my lube laden fingers made contact her legs began to close automatically, but she controlled that instinctive reaction and opened them even wider than before, defying her fears. I smeared the lube all around her entrance and then pushed two fingers inside her, making her dry passage slippery. All the time she lay with her hands clenched and her face turned away, her trepidation clearly showing. I was careful not to let any lube go down her perineum and onto her anus, she was worried enough as it was and I needed to make sure she knew I wasn't going to follow in my predecessor's footsteps. I pumped a little more lube onto my palm and then smeared that all along my cock and especially around its tip, before wiping my hand dry with the towel. We were all set, but I hesitated, wondering if she was still willing.

'Let's do it.'

I still wasn't sure if the breathlessness in her voice was arousal or nervousness, but I positioned myself ready, leaning over her on one arm so that I could reach back and guide myself into her. But I didn't get the chance to do that, she immediately reached down herself and took a hold of my cock before I could, directing it towards her entrance. I guess she wanted to be sure I entered the right hole. She rubbed the tip of my cock along her slit a couple of times as if trying to find the way in, until finally locating it and holding me with the head just resting at her entrance before pulling gently so that I just entered her. She moved her hand away and looked up at me, smiling faintly before nodding.

'Do it.' It was almost a command.

I settled myself on top of her, taking my weight on my elbows, and then thrust my way in, slowly penetrating her as deep as I could. She sighed, a protracted and deeply felt sigh that I interpreted as one of long awaited pleasure. I began to thrust rhythmically, driving my cock right up inside her, hearing her gasp each time the base of my cock met her pussy. But then, suddenly, with no warning whatever, she pushed at my chest and closed her legs beneath me, forcing me off.

'No, no. Stop, get off of me!'

I rolled to the side, totally confused. For a moment we each just lay there side by side, Judith staring wide eyed at the ceiling and panting, while I gazed at her, anxious to know what had gone wrong and hoping my fee hadn't just melted away.

'I'm sorry.' She whispered finally. 'I was frightened something like that might happen.'

'What went wrong?' I asked, almost certain that I already knew the answer but needing to hear it spoken.

'It was you being on top of me.' She turned her head to look at me. 'I knew you were doing it how you should and I knew you weren't him, but I just panicked in case you forced me into it again.'

I shook my head. 'I wouldn't do that.' I assured her. 'I'd never do that.'

'I know.' She agreed. 'I just couldn't help it; I just felt this sudden terror, and I was really enjoying it up until that moment. I'm sorry, you must think I'm very silly.'

'No way.' I smiled, hooking my arm gently over her shoulders and drawing her closer. 'I understand totally.'

She nodded and rested her head on my shoulder, her body alongside mine. 'So what do we do now? Do you want me to leave?'

'I most certainly don't.' I told her, and then switched to a fake salesman's voice. 'My aim is my client's complete satisfaction in every way.'

She smiled wanly. 'I'm not sure you're going to be able to do that this time. Especially if your client can't let you try.'

'There is a way.' I told her quietly.

She looked up at me and I'm sure I could see hope in her dark eyes.

'Why don't you climb on top of me and just straddle me? What they call cowgirl position. You'll be in full control then.'

'I'm not sure...' She prevaricated. 'What if it happens again?'

'Then you can just get off.'

She paused and looked up at me again, clearly considering the idea. 'Cowgirl, eh? But then I suppose every way of doing it has a name, doesn't it.'

The question was clearly rhetorical and so I just lay there and gazed down her body, appreciating the remnants of her former beauty.

There was another thoughtful pause, and then. 'Yes.' She said abruptly. 'Let's try that.'

'I'm glad.' I smiled broadly, and not only for commercial reasons. I didn't like the idea of failing her, even though I knew it wouldn't be my fault. I closed my legs together and withdrew my arm from around her. 'Ok, let's.'

She sat up and looked down at me, her eyes going from my face to my erection and back again before she nodded to herself and clambered over to straddle me. Once again she reached to steer me towards her pussy, lowering herself rather tentatively with her eyes locking onto mine. As soon as she touched the tip of my cock she stopped, licked her lips and gave a shy little smile.

'Try again.' She said softly to herself, sliding all the way onto my cock.

She settled herself on me with a little wriggle and looked down, her face serious but happy all at the same time.

'I think I can cope with it like this, Vince.' She announced. 'Let me just get used to it for a minute.'

'Good.' I replied, resting my hands lightly on her thighs. 'Take all the time you need.'

I know it might sound odd, but the feel of her mature pussy enveloping my cock felt really nice. She felt tight and warm and, because of the lube, slippery without being wet and sloppy. Somehow the fact that I was gazing up at someone whose body showed her years didn't seem to matter anymore. She had my cock inside her and it felt good. I must be getting a thing for older women I told myself with a secret smile, and that was no bad thing in my new line of work.

She knelt there over me for a good minute, looking down with a little smile of contentment on her face, just getting accustomed to the feel of a man inside her again after so long. Then she eventually began to move, slowly lifting herself until only the head of my cock was inside her and then lowering herself until she was sitting on me again. At first her movements were slow and careful, raising and lowering herself cautiously as if to make sure I did not slip out, but then as she became more confident she moved more quickly, pulling herself up and then pushing down herself hard onto me, her eyes closing and a more satisfied smile spreading over her face.

'I like doing this.' She announced breathlessly and suddenly.

'Good.' I replied. 'So do I.'

She giggled unexpectedly. 'Does it get me a discount, if you're enjoying it too?'

Her humour wasn't something I'd expected, she really was coming into her own. 'Only if I can charge you extra if you enjoy it more than once.'

More than once seemed a bit unlikely, I'd be happy if she orgasmed just the one time, but I was deliberately being optimistic for her sake. It seemed to work because her answer was to double her tempo, ramming herself down onto my cock and then rebounding back with a little gasp each time. I couldn't help but think that I must have stumbled upon the world's best way to earn a living, just laying there and watching a woman use my cock, her rather loose breasts were bouncing and jiggling, mesmerizing me as she did it. But they must have irritated Judith almost as much as they fascinated me, because she quickly covered them with her hands, pressing them against her chest to keep them still. I couldn't help but smile at her action.