My New Career – Diane


My accidental career as a gigolo began only recently and my very first customer was an elderly neighbour, Mary Shaw. I was penniless at the time due to the combination of a lost job and a broken marriage, and so I was only too eager to take up what might normally have been an unlikely occupation. I had initially intended it to be a one off with Mary, just to dig myself out of the financial hole, but, without wanting to sound big-headed, she was so satisfied with me that she recommended me to some of her friends and the one off became a career. Naturally her friends tended to be in the same age bracket as she was and so without really intending to I found myself looking after the needs of a number of mature ladies. But be that as it may, how can you top a job like that, having regular sex and being paid for it, no matter who it’s with?

One of these ladies was Diane, who rang me and made an appointment to visit me solely on the back of Mary’s recommendation. I suppose anyone doing my job wonders who they’re going to have sex with next and what sort of sex they’re going to be asked for. This was certainly the case for me with Diane, because when she rang she sounded most business like and told me quite bluntly that she expected me to do what she wanted and not just get myself off at her expense. My wallet instructed me not to turn her down, but I did wonder what I’d let myself in for.

Her knock on my door was rather peremptory, just a quick tattoo as if expecting me to be standing behind it waiting. That did nothing to reassure me about her, and nor did her appearance when I opened it. She was the epitome of an overindulged wealthy retiree, blonde hair permed to within an inch of its life, with most of the local make-up counter on her face and wearing a very vibrantly flowered summer dress. She had tried to hold back the years but only succeeded in looking eccentric. Just for once I hoped nobody had seen her calling on me.

The silly thing is that under all that was quite an attractive woman in a blousy sort of way. She wasn’t fat, but she certainly wasn’t skinny, just a little padded, although I wondered if her breasts hadn’t seen a surgeon’s knife at some point. Her face certainly had, which was a shame because her bone structure was fine. The effect was a little bit scary to be honest, she certainly gave the impression that she was used to getting her own way and the opening conversation proved that.


‘Yes, hello, are you Diane?’


I was going to say ‘come in’ at that point, but she already had, striding past me into my living room and then turning to await me shutting the door and following her. At least she had the grace to explain.

‘I didn’t want to be seen waiting at your door, someone might tell my husband where I was.’

I hadn’t known she was married, but that didn’t matter.

‘Not a problem.’ I told her. ‘Take a seat, can I offer you a coffee?’

She shook her head and sat down. ‘Thank you, but no.’

I sat down opposite her, the look on her face told me that she was intending to tell me something but wasn’t sure how. But then, after a minute or so thinking time she looked up and launched into her announcement.

‘I’m here because my husband isn’t up to it anymore; it’s as simple as that.’ She said. ‘But he must never know about this.’

I just nodded wisely. ‘I understand, and your visits will always be kept confidential.’ I said ‘visits’ plural somewhat optimistically, but you never know.

She delved into her purse and extracted some banknotes. ‘You’re not cheap, and so this is what I’m going to do. I have no objection to paying for quality, but I refuse to be fleeced by inferior service under any circumstances. So here is your money.’ She waved the notes around and then stood up and placed them under edge of the clock on my fireplace. ‘But I’m not here for a quickie; I want to be made love to properly and pleasured fully. Treat me as if I was your latest lover and you won’t go far wrong. Then if you’re as good as Mary Shaw says you are then I shall leave it all, but if I don’t get the satisfaction I’m looking for when I go I shall take back however much I think you don’t deserve. Those are my terms, do you agree to them?’

That was something I wasn’t expecting, my client telling me how they were prepared to pay, and I will readily admit that the implication that I might render an ‘inferior service’ irritated me somewhat, but I couldn’t let it show. In any case the devil in me is always up for a challenge so I figured I’d show her just what a quality service was. My only problem was that satisfying a woman as haughty as Diane Westbury might prove to be a difficult undertaking, but okay, I thought, if you want to be made love to properly, you’re going to wonder what hit you. ‘Oh, you won’t have any cause to complain.’ I told her smugly.

‘Good.’ She said, the first hint of a smile on her face. ‘Then shall we…?’ She was looking izmit escort around pointedly.

She was nothing if not practical. I stood up. ‘Let’s. It’s this way.’

She walked into my bedroom and immediately stopped and looked around, her eyes roving over everything in the room without a sign that anything was to her liking. I didn’t mind her not liking it, it was my bedroom and my taste, but I did want her to feel at ease as a customer, and so I tried to redirect her mind to other things. ‘Anything you don’t want me to do?’ I asked.

‘Yes.’ She replied. ‘I’m not into pain and keep away from my rear entrance.’

She turned her back to me and lifted her hair clear of her neck. ‘Undress me please.’

I moved forward and found the tab of her zip, pulling it slowly all the way down, deliberately allowing my fingertips to trace very gently down her spine as it went. Then I leaned forward and planted a soft kiss on the nape of her neck, feeling her shiver just slightly. Well, it was what I would do with my latest lover.

That set the tone for my undressing of her. I did it all from behind and stroked and caressed her at every opportunity. As I slid her dress from her shoulders I let my fingers run gently down her arms until her dress dropped away and pooled around her feet, and then I ran them very gently back up to her neck, stroking her skin but hardly touching, and breathing softly onto her neck. She didn’t move or speak to deter or encourage me, not even when I kissed her neck once more and trailed my lips down her neck and across her shoulders. She just stood there and accepted what I did. It was slightly scary getting no response, was this what she wanted or not? In retrospect I think she was coming to terms with more than she had expected, but at the time I had no way of knowing. Working on the assumption that she would stop me if she didn’t like it I carried on, touching her as softly and tenderly as I possibly could.

I unhooked her bright white bra, allowing the heavy contents to fall free as I slid the straps down her arms and lifted it away, intentionally stroking the sides of her breasts in the process before reaching back around and cupping them, my thumbs stroking her nipples. This time she did respond, I heard a quiet sigh and she leaned back against me, her head resting back on my shoulder. For a few minutes we stood like that, she naked except for her panties and me fully dressed and playing gently with her breasts. It would have appeared a strange tableau to anyone watching, especially as her panties were large, old fashioned and plain white to match her discarded bra. I wondered briefly if she had deliberately worn virginal white knowing that she was visiting me, or was it just her normal attire. It didn’t matter; I dropped to my knees behind her and hooked my fingers into their waistband, carefully sliding them down over her buttocks and down her thighs. She lifted one foot after the other to allow me to pull them clear and let them join her dress around her feet. This time when I leaned forward I planted a gentle kiss on each of her butt cheeks, being rewarded with a rather surprised gasp. I figured that I wasn’t doing too badly.

When I stood up I took hold of her shoulders and steered her towards the bed, standing over her while she sat on the edge for a moment or two, gathering herself before she swivelled to lie flat out and gaze up at me. I was looking down at a body a tiny bit past its best, although her large breasts seemed firmer than they had any right to be, maybe because of the thin scars under them, each one topped by a pink nipple surrounded by a very large pale areola. Her slightly rounded stomach showed just a little sign of a waist before it ran into a tidily trimmed pubic bush that betrayed her natural darker hair colour. It must be said that altogether she wasn’t as worn out as I’d feared. I gazed down and she gazed back, and then suddenly she smiled, the first smile I’d seen, and her face lit up. Undressing in front of me apparently hadn’t been quite the ordeal she had thought, and at least she was more relaxed now.

‘Are you going to join me?’ She hinted, her mouth curving quickly with a hesitant smile.

I smiled back and began to undress, pleased by the thought that she wasn’t quite as formidable I’d thought. I was beginning to think that her high-handed approach was only a front to cover her nerves. Whichever it was, I was pleased to find that she was beginning to thaw, although I still felt very conscious of her watching me as I undressed. I was just hoping that my cock would respond when it hit the open air, but the best it could manage at the prospect of making love to Diane was a reluctant half-mast.

‘Not ready yet?’ She asked, one eyebrow rose as she stared at me.

‘It will be.’ I assured her as I sat on the bed beside her. Now I had to set about pleasuring her ‘properly’ because I was absolutely determined to earn my pay, and then we’d both be satisfied!

I figured that there was no rush and that it would pay me to take my time, and so I began by leaning over and stroking her neck, running my fingertips very gently and slowly from behind her ear down until I was touching the very first curves of her breast, then across to the other one and up to her other ear before returning to where I began. Before I had completed two circuits like this her eyes had closed and she was visibly relaxing under my touch. I carried on doing it slowly and gently, just gradually extending my range and variations so that I turned my hand over and trailed the backs of my fingers over her lips, around her chin, down her arms and across her front, each time stroking just a little more of her breasts. All the time she breathing softly with her eyes closed and her mouth carrying a tiny smile.

Soon my hands were ignoring her neck and wandering almost exclusively over her breasts, sometimes I used the back of my hand and sometimes my gentle fingertips, all the time skittering so softly over her skin that I was barely making contact. Eventually I gave up all pretence of caressing her anywhere else and concentrated solely on her breasts, skating over the flattened mounds and drawing my fingertips across her nipples, occasionally deliberately catching them with my fingernails and making her gasp from the sensation. I wandered on, letting my fingers stroke her belly, again keeping it soft and gentle, so soft that sometimes the flesh of her stomach fluttered under the tiny sensations. From time to time I glanced at her, wanting to be sure that she was enjoying my attentions, but each time her eyes were closed and her mouth just slightly open, only her breathing betraying her heightening arousal. I smiled to myself and moved down the bed a little way, bringing more of her body within reach. Now I could do what I wanted and I ran my fingers down her side, from the nipple of one breast down to her hip and then on over her thigh almost as far as her knee.

Only now did she move for the first time, and that was just to part her legs a little, bringing her thigh within easier reach but also handing me an invitation to touch her so much more intimately. And so I would, but in my own time. Until then I let my fingers wander over her entire body, ranging from her breasts to her knees, never quite touching her pussy but sometimes just brushing past her bush, causing her to quickly lift her hips slightly in unfulfilled anticipation. I had to be careful that I didn’t take my teasing to the point of her frustration, and so after a few minutes I swung my legs up to lie alongside her and reached down between her thighs, hearing the sigh of contentment as her legs came further apart that told me I’d timed things just about right. Even so, I still wanted to take my time to make sure she got the full benefit from my efforts, and so I didn’t just concentrate on her pussy, I simply included it in my wanderings. At first I simply roamed up the inside of one thigh and down the other and back, lightly stroking her pussy as I crossed from one leg to the other. She moaned softly and draped an arm around my neck, gripping my shoulder harder every time my fingers touched her pussy. She was becoming more highly aroused and I figured now was the time.

This time when my fingers reached her pussy instead of passing on I let the tips walk along its length, two tracing their way up her labia while a third ran between to dip momentarily into her vagina before catching on her clitoris as it passed, Up and down her slit I trailed, listening to her quiet little moans become more louder and more urgent with each pass until finally I pushed two fingers straight into her wet and slippery vagina and pressed the ball of my thumb against her clit. This time she let out a loud gasp of excited surprise, instinctively pushing back against my fingers to try and take them deeper. I couldn’t help but smile to myself at how this very pushy mature woman was now almost literally under my thumb.

I fingered her hard, not fast, but forcefully, pushing my two fingers as far into her as they would go so that my knuckles were pressing up against her pubic bone before pulling almost all the way out again. Slowly but surely I increased the rate at which I thrust into her, never easing off on the strength but just getting faster and faster until my fingers were thudding into her and she was responding by groaning deeply, wriggling and pushing against my fingers. Her grip on my shoulders was becoming noticeably stronger all the time until suddenly she gasped loudly and pulled me to her, pushing my face onto her breast so that I could feel her nipple pressed into my cheek. For a moment my fingers slipped from her soaking pussy as I tried to regain my balance, but then I let my body rest against hers and turned my face to take her nipple into my mouth before slamming my fingers back into her as hard as I could. She kept her arm around me, holding me tight and gasping harshly while I sucked and chewed at her nipple and carried on fingering her, my thumb hitting her clit each time. Then, all of a sudden, without any further warning, she came, gasping and calling out as she bounced on the bed, her free hand scrabbling to grab mine and ram it even harder into her pussy.

‘Yes, oh yes, oh my god yes.’ Her voice was loud in my ear as she announced her climax, her hand holding my fingers inside her so that I could feel the throbbing of her pussy until her orgasm slowly faded and she released me to fall back on the bed, gasping and panting.

‘My god.’ She got out eventually. ‘Thank you.’

That, I reckoned, was my money earned. I couldn’t see her removing any cash if she was thanking me for what I was doing, although it wasn’t over yet of course. But at least my cock had finally decided it liked my line of work and was upright and ready to perform. I think it had been Diane’s orgasm that had persuaded it. We sprawled silently side by side for a few minutes while Diane regained her breath.

‘Would you lick me there please?’ She asked suddenly, her eyes pointing downwards.

That was an improvement. I was pretty certain that when she first arrived that would have been phrased as an instruction rather than a request. My only annoyance was that she had beaten me to it. I was still intent on showing her that my service was not as inferior as she had implied and oral sex was the next thing on my list to prove her wrong, even though I was beginning to think that she hadn’t really meant it.

I moved around and positioned myself between her legs, pushing them apart to give me room and then pausing to gaze down at her pussy. It didn’t look like an old woman’s pussy, I mean, yes her outer lips were a little slack but her inner lips were short and simply guided my eyes to her little button peering out shyly from under its hood. It was time to impress her with my oral skills, or maybe my lack of them, and so I rolled back her legs with my hands, using my thumbs to part her labia, and then lowered my face to her pussy.

I ran the flat of my tongue along the length of her slit, lapping at her juices, dipping my tongue tip into her hole, and then licking all the way along until my tongue flicked at her clit. I heard quick little gasps each time I made contact there, and so I concentrated on her button. I placed my mouth over it and then kind of sucked it out from under its hood so that I could massage it with my lips and tongue, stretching it taut by gripping it between lip covered teeth and then flicking and licking it with the tip of my tongue. It didn’t take long before she was moaning again. I could also hear sharp gasps of pleasure when I lapped at her clit, and she quickly began fidgeting under my hands as her pelvis responded to the sensations she was feeling. I felt a strange pride in getting her to react so quickly and I could sense a second orgasm was on its way. I gripped the flesh of her thighs with my fingers, holding her, trying to make sure she wouldn’t be able to squirm free of whatever my tongue was doing. I was intent on making this orgasm even stronger than her first.

I released her clit for the moment and moved downwards until I could reach her vagina, licking around the entrance and then stabbing my tongue as far inside her as I could. She moaned loudly and her body jerked upwards from the sudden sensation as if wanting me to go deeper. But my tongue was gone, licking its way back along her pussy, rolling around her clit before taking her nubbin into my mouth like before and biting it gently, licking the very end now with the tip of my tongue. I suppose I was teasing her again in a way, but it didn’t seem like it as I alternated between licking her clit, pressing the flat of my tongue along the length of her slit and stabbing it into her entrance.

The combination was too much for Diane and she climaxed noisily once more, this time twisting her fingers into my hair and pulling me hard against her so that my face was squashed into her pussy. She rubbed herself back and forth on my face; powerful floods of pleasure making her cry out again. I couldn’t breathe, but I held my breath and extended my tongue, trying to give her the last possible moment of pleasure until I was finally forced to turn my wet and slippery face away and take deep urgent breaths before my lungs exploded.

This time we both lay side by side fighting for breath and smiling stupidly. Diane from her orgasm and me from being pussy suffocated, although that mattered little. As our breathing slowly returned to normal she looked sideways at me and giggled girlishly.

‘You’re covered in my wetness.’ She told me, beaming smugly.

‘That’s ok.’ I told her, still feeling a little out of breath and thinking that even though I’d already earned my pay I still needed to earn release for my suddenly eager cock. By my reckoning it was time to move smoothly on to the finale before she decided she’d had enough. I turned on my side to face her. ‘As long as you enjoyed it.’

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