My New Career

'I'm not worried about that.' I told her honestly. 'I just don't want to let you down.'

'I'm sure you won't.' She smiled. 'Shall we go upstairs?' She climbed to her feet, clearly eager to get started.

I ushered her towards the stairs, glad that I'd spent yesterday cleaning up my bedroom and changing the sheets. As she reached the bottom of the stairs suddenly she turned to me as if remembering something.

'I'm just about to go to bed with you, and I don't know your name.'

'I'm Vincent, or Vince.' I told her.

'And my name is Mary.'

What a time to introduce ourselves.

She let me lead the way upstairs and then I ushered her into the bedroom - my newly cleaned and tidied bedroom. I'd left the curtains drawn since getting up that morning so that nobody would notice them being closed just after my visitor arrived and put two and two together, so I switched the light on and let her look around. I could see her registering approval of what she saw, thanks mainly to my wife making the tasteful choices that I'd luckily not yet got around to replacing.

'If you're ready, Vincent.' She began. 'I'd like you to undress me.'

This was plainly going to be the most businesslike session that I'd ever had - but then I suppose it actually was business. I walked forward and began to unbutton her blouse while she just stood there and let me. Soon she was stripped naked with all her clothes draped over a bedroom chair, and looking a lot more inviting than I'd expected. Somehow I'd expected her to be shy and perhaps a little embarrassed, but not a bit of it. She stood there in front of me, her feet planted a little way apart, deliberately letting me look at her - and it must be said that I was pleasantly surprised by what I saw.

When I'd seen her with her gigolo partner I'd been too surprised to take much in. In any case he was covering most of her and so in reality I was seeing her for the first time. Perhaps I'd been dreading her being nothing but a sack of scrawny sags, with empty tits hanging in front of her and with wrinkles on top of wrinkles, but she was so much better than that. It must be said that her age was showing in her somewhat skinny limbs and in breasts that were lower than they once had been, but she was still more sexually attractive than I'd thought she would be. It was also true that she had a more exuberant and wayward bush than a younger woman would sport, but that wasn't a problem. Maybe earning my money would be easier and more enjoyable than I'd anticipated.

'Not too bad, am I?' She smiled, as if reading my thoughts.

I felt myself go red. 'Yes - I mean, no,' I faltered, hearing her giggle girlishly at my embarrassment. I pulled myself together. 'Actually, you're pretty damn good.'

'Well, thank you kind sir.' She laughed, and pirouetted to show me a surprisingly trim bottom. 'Maybe I was once, but I'll take all the compliments I can get these days. But now it's your turn.'

I thought I knew what she meant and so I crossed my arms and took a hold of my sweatshirt, intent on pulling it over my head.

'No.' Her voice came quite sharply, underlining who was in control. 'Perhaps I should have said it's my turn.'

She came across and took hold herself, pulling my top over my head in one practised sweep and dropping it onto the chair with her things. My jeans followed in short order and then everything else, so that I was soon standing as naked as she was, with my cock twitching into hardness before me.

'I see you don't find the prospect too repulsive.' She smiled down at my growing erection.

'Not a chance.' I assured her, wondering what to do next.

I needn't have worried, she had it all planned out. She took my hand and led me towards the bed, my own bed, and then climbed on, patting the space beside her. 'Come on, we not going to do it standing up.'

I went and lay down beside her, rolling onto my side to look at her.

'I told you I want to be made love to my way, didn't I?' She asked, reminding me of our agreement. 'Especially this first time.'

I nodded my answer without speaking, my eyes roaming up and down the length of her body and really not disliking what I saw.

'Then kiss me.'

For some reason I hadn't expected to do that and for one insane and disconcerting moment I had a vision of kissing her and dislodging a set of dentures from behind her creased lips. I drew back in surprise, thinking that I'd reached the first stumbling block quicker than I'd imagined.

'Kiss me.' She demanded again. 'It is part of making love after all.'

She was right; it is a very basic part of lovemaking and I'd signed up to making love to her. And in any case, I told myself, I could see that she didn't have dentures.

The happy thing about kissing someone is that you're expected to close your eyes and so I did, and that led me to a surprising discovery. Her body against mine felt no different to a younger woman's, her skin felt the same as anyone else's, and her kiss was just as enjoyable as any I've experienced. And most importantly, my cock agreed. If it was going to fail me then I'd figured this would be the moment, but instead it pressed rock hard against her belly. To my surprise I was actively enjoying kissing a woman so much older than myself - and that had great potential for my prospects.

That first kiss was experimental, as if we were both testing the water, but then, the test having been passed, we kissed again, this time with our tongues probing and exploring like long term lovers. It was nice, I mean it was really nice, and we carried on, our arms around each other, hands roaming, lips and tongues playing enthusiastically. I could feel Mary's body pushing against mine, her breasts on my chest and the rough curls of her bush on my belly as we held each other close. Then I began to hear little noises coming from her throat and vibrating in my mouth, noises that told me she was enjoying everything just as much as I was. When we finally pulled apart a little we were both slightly out of breath and smiling happily.

'I think that was a good start.' She told me, holding me away enough to look directly at me. Close up she still looked attractive and I came to the instant conclusion that grey hair and blue eyes look fabulous together.

'So do I.' I told her, leaning forward hesitantly to kiss her a third time, half expecting her to remind me who called the shots. But she didn't and our mouths locked together again. This time as we kissed I felt her hand slide down my arm and onto my hip, pausing there before working its way between us and wrapping itself around my cock. I eased away slightly to give her more room, maintaining the kiss even as she began to stroke my shaft, running a cool hand up and down its length.

She took her lips from mine and whispered in my ear. 'I was just checking if I liked what you've got for me, and I do.'

I smiled. 'Thank you.'

'And you might like to check me out as well, seeing as I'm likely to be more dilapidated.' My cheek felt a mischievous smile spread across her face.

'Surely not?' I whispered back, my own hand working its way between us to find her breast.

'Find out for yourself, and then you tell me.'

I sensed that she wouldn't want me just to flatter her, and then I found telling the truth was easy anyway. I squeezed her breast in my hand, feeling her hard nipple press into my palm, and that also felt far nicer than I'd imagined for someone so much older. She wasn't as firm as a twenty-something girl, but she couldn't expect to be.

'You feel nice' I told her. 'And you've got lovely nipples.'

She chuckled in my ear. 'I admire your diplomacy.' She teased. 'Nothing good to say about my breasts, so just lovely nipples.'

'But they're both nice, but your nipples especially.' I protested, gently squeezing the one in my hand. 'They're long and hard and they feel lovely.'

'Suck them then.' She let go of my cock expectantly. 'See if they taste as good.'

That was no hardship at all. I disentangled myself from her embrace and wriggled a little lower on the bed, leaning over as she settled on her back and fastening my mouth around one nipple and my hand over the other.

Remembering what my ex used to like I started by using just my tongue, running it softly around her areole and then across the tip of the nipple itself, round and round, making it just a little firmer each time, until I was licking her hard, flicking my tongue across her nubbin to make it rebound harder and longer than ever. At the same time I was lightly pinching her other breast, drawing it into a peak between my fingers by tugging at her nipple. I could hear hissing intakes of breath and her one of her hands laid itself lightly over my head, holding me gently in place. Then I drew my lips over my teeth and nibbled at her, pulling at that nipple too, stretching it until it slipped from my mouth and bounced back, only to be taken between my lip-shielded teeth once more.

'Play with me down below.' She demanded suddenly, pushing my hand away from her breast in case I hadn't understood.

I let my hand be pushed lower until it reached her pubic mound, and then I reached between her widespread legs, running my fingers through her wiry hair and cupping her pussy neatly in my hand, feeling warm dampness on my palm.

'Play with me.' She insisted huskily. 'Rub my clitoris.'

It seemed weird to hear a sophisticated older woman talking like that, but I knew what she wanted and I obeyed willingly enough, seeking out her clit and stroking two fingers across its tip. Just like her nipples it was long and hard - and sensitive. I quickly felt her body give little jerks in response to my movements, twitching as my fingers rubbed her button. All the time I played with her I still kept licking and sucking at her nipple until soon she was gripping me tightly and gasping from the sensations.

'Oh my!' She murmured, almost to herself. 'It's going to happen.'

And happen it did. Hardly had the words left her lips than she groaned loudly, her pelvis lifted from the bed and her entire body went stiff. She held that position for what seemed like ages, making a series of harsh little sounds in her throat before, as quickly as it had arrived, her orgasm passed and she collapsed back onto the bed, panting for breath. I stopped playing and just rested my hand on her pussy, feeling surprised but very pleased with myself. I hadn't imagined she would come so easily.

'Heavens.' She gasped. 'That was wonderful. I can't ever remember coming that quickly. I guess I must have needed it.'

'I guess you did.' I agreed, laying my cheek on her breast and trying hard not to sound smug.

I made to take my hand away, intent really on moving back up the bed and giving her a kind of congratulatory kiss, but she quickly reached down and grabbed my wrist, holding me in place.

'No, don't stop, I want to come again yet.' She commanded urgently.

'Good, I want you to.' I told her, meaning it. I was starting to find my time with Mary pretty exciting, a whole lot more so than I'd expected. It was a revelation to me that a woman of her age could be so easily aroused and so sexy, and I wanted to see how far that went. Of course, I also wanted to make sure I got paid. She said she would pay me and make it regular if it worked out, so this was like a kind of audition and if I passed I would get the job. And what a job, servicing an attractive older woman and getting well paid for it. So yes, I did want her to come for a second time.

I began to play with her again, letting my fingertips flick the head of her clit where I could feel it peeping from under its hood, doing it gently at first but then as she began to react, more firmly and more rapidly. She soon started to make little noises again and her hand gripped my shoulder, revealing her renewed arousal. I smiled to myself, as if feeling her pleasure myself. I wasn't sucking at her nipple this time, but resting my cheek on her breast and looking down her belly, so my smile went unnoticed. It was nice to watch even if I could see very little, although I could see the quick movements of my hand as I rubbed her clit, and I could see the muscles of her thighs and belly tighten irregularly as the pleasure of it got through to her.

I think she must have realised what I was doing, because suddenly she asked 'Are you looking at me?'

'Yes.' I answered simply, expecting her to disapprove.

'What can you see?'

'Not very much.' I told her, uncertain if she wanted me to see her pussy or not. The uncertainty didn't last long.

'Move then.' She told me, her voice thick with arousal. 'Move down so that you can see what you're doing.'

I glanced up at her in surprise at her instruction.

'Move down.' She repeated, frowning slightly. 'Move to where you can look at my pussy, I know it sounds strange, but I want you to watch what you are doing to me.'

That was another surprise; she hadn't seemed the type to be crude. But whether it was crude or not, I was hers to command. Taking my hand away for the moment I wriggled down the bed so that I was propping myself on one elbow just about level with her knee, and then I reached back towards her pussy.

'Just a moment.' She instructed.

I stopped and waited, not sure what she intended until I saw her pull her nearest leg right back and swing it over me so that I was crouching between her wide open legs. Then she reached down with both hands and pulled open her labia, holding them back with her thumbs.

'Now.' She asked. 'What can you see?'

I felt my eyes widen in astonishment at her directness. 'I can see everything.' I told her, not sure what she wanted to hear.

'Can you see my little soldier?' She asked girlishly. 'Is it on parade?'

'Yes,' I told her. 'It's all swollen and red, and lovely.'

'What about my hole? Can you see inside me?'

I could see both holes, but I knew which one she meant, and yes, I could see inside her, she was wet and gaping, slippery with juices. 'Yes, I can. You're wide open and shiny, waiting for me whenever you want me.'

It was a strange conversation and it both shocked and aroused me in equal measure. From a young sexy woman it might be expected, but from a woman of her age and class it was an eye opener, but then Mary Shaw was obviously far from being as reserved as one might expect. In fact she seemed very uninhibited and more than a little exhibitionistic. I was getting an express lesson in the sexual nature of mature women, and it was coming as a welcome surprise.

'Do you like what you see?' She asked.

'Oh yes, definitely.' I answered without hesitation. What's not to like about gazing at a woman's wet pussy?

'Play with me then. Make me come again.'

My hand went to her pussy as if of its own accord and began to play with her clit, my two fingers straddling her button and rubbing from side to side. At first they worked slowly and gently but then I rubbed harder and quicker as I felt her begin to twitch and writhe under my touch. It was working, but I wanted to do more, I wanted to push my fingers inside her, to finger her as well so that she would come harder than before. I was still looking to make sure this became a regular source of income, and so I took the risk and moved my fingers away for a moment.

'Don't stop.' She instructed me at once. 'I want you to make me come again.'

I didn't answer, I simply made a gun from my first two fingers and thrust them hard into her gaping vagina, with my thumb, like a revolver's hammer, banging up against her clit. She jerked and gasped in surprise before relaxing back.

'You devil.' She gasped. 'I didn't say you could do that.' She paused. 'But thank you.'

I smiled to myself and carried on finger-fucking her. My two fingers plunging into her slippery passage and my thumb ramming onto her button. She was still holding herself wide open, giving me a fantastic view of her shining and soaking wet pussy. I could even hear little squelching noises as my fingers moved in and out of her. Soon she was shuddering with arousal once again, her hips pushing at me each time I thrust into her.

And then she was there, her second orgasm arriving just as suddenly as her first, and causing the same fabulous reactions. She didn't warn me this time, she just came, groaning noisily deep in her throat and lifting her pelvis high from the bed before collapsing back to slump panting and trembling, her hands falling away from her pussy and her legs dropping onto the bed to either side of me.

For a moment or two she just lay there and I simply waited, my motionless fingers still buried deep inside her pussy, but then she licked her dry lips and pushed my hand away.

'Suck your fingers.' She commanded, still breathless.

I looked at her without moving, shocked by what she had asked.

'Go on, do it.' She repeated. 'Suck my juice off of your fingers.'

It was not something I'd ever done before, or been asked to, but I found my hand moving towards my lips almost of its own free will. Without taking my eyes from hers I opened my mouth and pushed my fingers in, licking her moisture from them and then showing her that they were clean. She tasted lovely, a lovely turned-on woman taste.

'Good. Now lick me.' She was smiling at me, clearly pleased with the way things were going.

Just for a moment my mind baulked at the idea. She was so much older than me and I had just been staring at her relatively slack and hirsute pussy held wide open by slightly arthritic knuckles, and it abruptly seemed a less than attractive sight. But then I remembered I'd already tasted her and I recalled how I'd felt about kissing her on the mouth, and how wrong I'd been about that too, and so all of a sudden the idea didn't seem anything like so repellent.

So I moved to be sprawled between her legs, my hands at the top of her thighs to push them back and my thumbs holding her labia apart, and my face only a few inches from her pussy. For a moment or two I stayed there, gazing at her shiny flesh and savouring the aroma of a woman's arousal, and then I slowly lowered my mouth to her slit.

If anyone had told me a week or so before that I would be going down on a pensioner, I would have laughed and told them not to be so stupid, but here I was doing just that, and more to the point I found I liked doing it, regardless of the payment I was receiving. I put out my tongue as I neared her pussy and licked it from one end to the other, unexpectedly enjoying the experience. I was used to her taste now, and I loved it, letting the flat of my tongue run all the way up and down her pussy, pushing it into her hole and then flicking the tip of her clit with it. She gasped with each little flick; a quiet little 'oh' and a tiny jerk of her hips showing how much she liked it.

It didn't take long before her gasps became louder and her movements stronger, and I smiled to myself, sure that I was going to bring her off for a third time. But Mary is nothing if not unpredictable, and suddenly she pushed me away, swung her leg back over me and sat up, breathing heavily.

'What's the matter?' I asked, confused and disappointed, and fearing for my pay.

She shook her head and then gasped. 'Nothing.'

I must still have looked confused, because she licked her lips and tried to explain between breaths. 'You nearly made me come again.'

I waited, wondering why that would be a problem.

'I can't keep coming like that; I don't make it beyond twice usually.' She took a deep breath. 'And I want to climax when you enter me.'

I smiled as she explained, listening to her quaint phrasing, and then I abruptly realised that I hadn't failed - I'd been better than she expected.

'I'm not as young as I was.' She went on. 'And my heart is pounding like mad. Give me a minute to get my breath and then we'll do it.'