A Week with Diane

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This story is not, like some of my previous stories, a romance — it’s basically about a young guy having raunchy sex with a lady in her late sixties. It does contain quite a lot of anal sex play so if this isn’t your preference this story may not be for you.

All comments and feedback welcome, as always.



Great Whiston is variously described by estate agents as a bustling village or a small town, depending upon who they’re trying to sell a house to. I was only in the area for a month, so I didn’t care one way or another about the distinction. And of course I was only renting — an eighteenth-century brick cottage on the outskirts of the village/town which suited me fine because it was only two hundred yards from one of the two pubs and I could eat all my evening meals there without the faff of having to go out shopping and cook and clean up afterwards. The joys of an expense account!

I’m Stewart, by the way, a twenty-eight-year-old solicitor and junior partner in the firm, which means I get all the jobs that require travelling away from home for any length of time. I don’t mind; I’m single and unattached and there’s always the chance of a no-strings fling with one of the local girls. Which is what happened here, except that you wouldn’t really describe Diane as a girl.

The story starts near the end of the third week of my stay, in the month of July. I was overseeing a big commercial purchase and it was going smoothly and I’d be back at base in a little over a week. The Plough public house was doing a grand job of looking after all my nutritional requirements with an albeit limited range of meals such as ‘cod and chips’ and ‘pie of the day’ or ‘Thai green curry’. Then someone spotted a rat in the kitchen and grassed them up to the local council who withdrew their food licence until they’d dealt with the infestation and done a deep clean. That meant I had to walk to the other end of the bustling village which, on foot, felt more like a small town, to The Feathers, which was the more up-market of the two public houses and which I hadn’t yet been in.

It was subtlety different to The Plough: for one thing it was carpeted throughout and there were white linen tablecloths on the tables in the dining area. The menu was different too, more gastro than pub grub. That Monday evening I opted for whitebait followed by lamb cutlets and, taking a paperback out of my jacket pocket, settled down to read and wait for my food, a pint of bitter on the table in front of me.

It was about seven-thirty and although the dining area was quiet, there were quite a few patrons in the lounge bar and in the snug that adjoined it. I’m pretty good at blocking out background noise but some of the voices, especially the strident tones of the gentlemen farmers, penetrated my reading. After one particularly loud burst of laughter, emanating from the snug, I looked over in irritation. Nobody noticed my peevish glance except a middle-aged lady facing me, penned in by two grey-haired, pink faced hunks in Harris tweed jackets with leather elbow patches. She smiled at me sympathetically and I nodded slightly and went back to my book.

Five minutes later I became aware of scrutiny from across the room, as one sometimes does, and I looked up to see that the lady in the snug was still looking at me. She didn’t look away in embarrassment or anything, in fact she smiled at me again and then addressed a remark to her neighbour. My meal arrived at that point and I turned my attention to it. Well, most of my attention. Because I was now aware that I was being watched from across the room. Not continuously, that would have been weird, but enough for me to be aware of it.

Half an hour later I’d finished my meal and asked for the bill. Across the room, in the snug, the farmers and their spouses were getting up to leave. The barmaid came over with the card reader and put another glass of beer on the table.

‘I didn’t order another pint,’ I said.

‘It’s from the lady over there,’ she replied, waving a hand in the direction of the snug. ‘She said they might have spoilt your meal with the noise they were making.’

‘That’s really not necessary,’ I protested, looking over at the backs of the party who were now disappearing through the door into the High Street. She didn’t reply and I paid and slipped my book back into my jacket just as the lady who’d been staring at me came out of the ladies’ toilet. She glanced over at me then walked across the dining room and stood by my table.

‘I’m sorry we were so noisy. My chums get a bit boisterous after a day of strutting about their farms and ordering everyone around. I hope it’s bitter that you were drinking.’

Chums? It sounded like something from a nineteen fifties kids’ comic. And the accent was pure English upper-middle-class. I glanced up and found myself looking at a remarkably attractive woman. Close up it was evident that she was older than the mid-fifties I’d Yeşilköy escort assumed from across the room, more like mid to late sixties I’d have guessed, maybe even early seventies. Her shoulder-length dyed blonde hair curled in at the ends and framed a face with humorous grey eyes, a straight nose and full lips. True, there were lines on her forehead and above her upper lip and pouches under her eyes. There was also slight sagging of her cheeks and some loose skin at her throat but this seemed not to detract from my overall impression of a good-looking and carefully made-up woman. Twenty or thirty years ago, I felt, she’d have been a real head-turner.

‘Thank you,’ I said, ‘but it’s really not necessary. You expect a bit of noise in a pub.’

‘Well I can’t take it back now,’ she smiled. Then she held out her hand, some light brown spots and prominent veins on the back but with long, slim fingers tipped with crimson lacquered nails. ‘I’m Diane.’

I stood and took her hand. Her grip was dry and firm. ‘Stewart.’

‘I don’t think I’ve seen you in here before, Stewart. I’m sure I’d have remembered a handsome chap like you.’ She made no move to release my hand.

‘Oh I’m only here for a few weeks. It’s nearly up now. I’ve been eating in The Plough,’ I added. It’s just down the road from where I’m staying, next door to the Post Office.’ I don’t know why I felt it necessary to add all this explanation; by now Diane had released my hand but she still made no move to go after her companions.

‘Don’t tell me you’re renting the Old Bakery!’

‘Yes, why?’

She laughed. ‘It used to be my home, when I was a child. The family still owns it. How are you finding it?’

‘It’s lovely. It’s just the sort of place I like. Old, characterful but not falling down. And it’s handy for the pub, at least it was until they had a visiting rodent.’

‘I haven’t been inside since it’s been rented out, years ago now.’ She paused and looked at me. ‘Would it be terribly inconvenient of me to come and have a sneaky look inside? It would bring back so many memories.’

‘Of course,’ I said. ‘When would be best? I mean I don’t do much after work.’

‘Shall we say tomorrow evening then. Would eight o’clock suit you?’

‘Yes, that’s fine.’

‘And you’re sure I won’t be putting you to any trouble?’

‘No, of course not.’

‘See you tomorrow then, Stewart.’ She turned and walked across the dining room towards the door and I saw, inconsequentially, that she was quite slim and had nice legs. Was it my imagination or had there been a hint of invitation in her last remark? Surely not.


I was at my client’s office until gone six. It was a full-on day and I only remembered about Diane as I was driving home. She was due at eight which didn’t give me enough time the eat at The Feathers so I got a frozen ready meal from the village store and defrosted it in the microwave while I tidied the house. It didn’t take long; I’m not a messy person and I hadn’t brought much stuff anyway.

She was ten minutes late, ringing the bell just as I was beginning to wonder if she was coming at all. But there she was when I answered the door, smiling at me with her white teeth, her lips a deep red, and simply dressed in a pearl-coloured satin blouse and a dove grey skirt that came to just below her knees — it was a warm evening.

‘Come in,’ I said, stepping aside. She walked past me, through the tiny entrance hall and into the sitting room, a faint scent of rosewater trailing behind her.

‘It hasn’t changed much,’ she said, looking around. ‘Of course we didn’t have a great big flat screen television, just a little black and white thing that was always going wrong. And my mother had a rocking chair in that corner. She used to rock while she darned socks. All those years ago,’ she sighed. ‘Do you mind if I look round the whole house, Stewart?’

‘Be my guest. I was going to offer to show you but you probably know your way around better than I do.’

‘In that case,’ she said, ‘I’ll show you around.’

We went into the little dining room and then the kitchen. ‘This is all new of course,’ Diane ran a red-tipped finger over the granite work surfaces, ‘probably several times over. We had an earthenware sink, and a mangle instead of a tumble drier!’

The stairs were off the kitchen and I followed her up, feeling a bit guilty about staring at her bum and legs, which were encased in smoke grey tights — or stockings. She showed me which bedroom used to be hers and which was her elder sister’s and how the bathroom had changed since the nineteen fifties. Then we went into the master bedroom.

‘This was my parents’ room. I was born here.’

I was amazed. ‘Seriously? In this actual room?’

‘Yes, but not on this big fancy bed.’ She looked at me with a hint of a smile. ‘I’ll bet it’s seen some action.’

‘Not while I’ve been here,’ I admitted.

‘What, a good-looking Yeşilyurt escort bayan young man like you? I’d have thought the local girls would be queuing at the door!’ She reached out and laid a hand on my bare forearm — I had changed into chinos and a short-sleeved shirt after work. She was standing very close to me and her scent was in my nostrils. ‘They would have been in my day.’

‘I’m only here for a month,’ I said, weakly.

She looked at me critically for a second or two then released my arm and went downstairs. I followed.

‘Can I offer you a drink,’ I asked, as we stood in the sitting room.

‘Well as a matter of fact I brought something as a thank you for letting me look round.’ She reached into her leather shoulder bag and pulled out a bottle of chianti. ‘Why don’t we open this?’

I fetched glasses and a corkscrew and poured us both a drink of the fruity Italian red. Diane sat on the two-seater settee and I took the single chair. Once seated she crossed her legs elegantly, straightened her skirt and sipped her wine.

‘Tell me about yourself, Stewart. Are you married? Engaged?’

‘Single, at the moment.’

‘Playing the field eh? Good for you.’

‘Well,’ I said, trying not to blush, ‘something like that.’

‘What about the boring stuff like where do you live and what do you do for a living.’

‘I’m afraid it is pretty dull. I live in Worcester and I’m a conveyancing solicitor.’

‘And what do you do when you’re not soliciting?’ She smiled at her deliberate misuse of the word and I grinned back.

‘Oh not too much. I run quite a bit, go to the gym, play golf. And I read a lot, too. What about you,’ I asked, feeling that the conversation was in danger of lapsing into an interrogation. ‘Have you always lived in the village?’

‘No. I lived here until I got married, a terribly long time ago, and then my husband and I went off to Kenya for twenty years. He was an architect. We came back after his mother died and inherited a great big old pile at the other end of the village and I’ve lived there ever since.’

‘With your husband?’ I couldn’t help asking.

‘Until he died, twelve years ago.’

‘Oh, I’m sorry.’

‘He was quite a few years older than me.’ She shrugged and we sipped our wine in silence for a few moments and, uninvited, I topped up both our glasses.

‘You’ll get me all tiddly.’ Diane smiled archly at me. ‘And then goodness knows what would happen.’ As though wishing to find out, she finished her glass in about four or five mouthfuls and patted her lips delicately with a lacy handkerchief that she kept up the sleeve of her blouse.

‘Actually I’ve got a Women’s Institute meeting in the village hall at nine-thirty and it wouldn’t do to turn up looking the worse for wear. Though God knows you need a few drinks to combat the boredom. Otherwise I’d be quite happy to sit with you and drink all evening.’ She paused, looking at me. ‘I probably shouldn’t say it but I do find you a remarkably attractive man. I’m sure that sounds terrible coming from an old thing like me.’

‘You’re an attractive lady,’ I said, without thinking. Though it was true, she was, in an old-lady sort of way.

‘I was once,’ she replied, wistfully. ‘And thank you, that’s very gentlemanly of you.’ She quickly applied a touch of lipstick then stood and smoothed her skirt. ‘Now I should be going.’

I opened the door into the tiny hall and she went through and I followed her and we stood very close together, her scent in my nostrils again.

‘Thank you, Stewart, for showing me around. I’ve enjoyed meeting you very much. It’s a shame you’re going away so soon…’ We looked at each other for a few seconds and I was just about to open the front door when she reached up and put her arm around my neck and pulled my face down to hers, her lips meeting mine and opening in invitation.

The kiss lasted about twenty seconds and it didn’t feel like I was kissing an old-age pensioner. Quite the reverse. It was one of the sexiest and most intimate kisses I’d ever had: warm and liquid with lots of lip and tongue work. It was Diane who broke off.

‘Hold out your hand,’ she said, rummaging in her shoulder bag and finding a biro. I held out my hand, palm up, and she scribbled a phone number across it. ‘That’s my mobile number. I’d love to hear from you but if I don’t, I won’t contact you.’ She said this without looking at me, presumably embarrassed, and next thing she’d opened the front door and was disappearing down the path to the High Street. I watched her go then shut the door and looked at myself in the hall mirror. I looked shell-shocked, and there was lipstick around my mouth.


It was difficult to concentrate the next day at work, which was a problem because I was drafting the final contracts and they had to be right and reflect all the things we’d agreed over the past few weeks. But I couldn’t stop thinking about Escort Zeytinburnu the previous evening, about Diane.

That kiss had been dynamite, had changed all my preconceptions about older ladies. I’d gone back into the sitting room in a daze and finished off the bottle of wine, my penis rigid in my chinos. Then I’d gone to bed and masturbated while visions of Diane floated through my mind and I tried to visualise what she’d look like naked, or partially clad. How she would look underneath me as I thrust into her and how she would smell and taste. I came like an express train and half an hour later I was hard again.

It’s not that I hadn’t thought about older women in a sexual sense before, I had, often. But the older women were in their forties, not their sixties or seventies. I just had never considered ladies of that age in a sexual context. But after yesterday, a whole area of previously unexplored erotica seemed to open out in front of me.

I managed to get through the day without any disasters and went straight home where I took out my phone and looked at it, pondering. I had come to a conclusion by about lunchtime that I would contact Diane and suggest meeting up. But how should I phrase it? I didn’t know the woman and although her intentions seemed pretty clear she came from a different generation to me. One that was (supposedly) subtler, less forthright perhaps. I’d put Diane’s number in my phone the night before, now I tentatively started writing a text:

Dear Diane. Thank you for yesterday, it was really good to talk with you too. Although I’m only here until Friday, I would like to see you again if that’s convenient. I’m free this evening, if that’s any good.

Look forward to hearing from you.

Stewart xxx

I read it over a few times. The “I’m free this evening, if that’s any good” bit sounded a little needy but it was true and anyway, what the hell. Nothing ventured and all that. I thumbed “send”.

An hour later, as I was pacing up and down and telling myself that the whole thing was a mistake, my phone bleeped it’s incoming text message alert and I fumbled the thing off the coffee table and read her reply.

Dear Stewart,

I’m so glad you’d like to get together! I was worried that my kiss was a bit much and frightened you off! And tonight would be lovely. I’m supposed to have a meeting about the harvest festival at seven o’clock but I’ll make some excuse, put them off for a couple of hours. Come to me — it’ll be more discreet! My house is the red brick place that backs onto the playing fields. There’s a black-painted door in the wall which I’ll leave open. Come as soon as you can!

I stood in the sitting room and breathed deeply, excited beyond measure, my cock like iron in my underpants. Realising that I hadn’t eaten I went next door to the Post Office and bought a sandwich from their chiller and ate it with a cup of tea. I had a shower and changed into a casual shirt and trousers, then I texted Diane:

On my way xxx

I wanted to savour the walk to her house but Great Whiston really isn’t a very big place and ten minutes later I was pushing through the black, wooden door in the brick wall that ran along one side of the village playing fields and hoping it was Diane’s house.

It was a big, detached place: Edwardian, I guessed, and set in secluded and substantial gardens. There was a conservatory on the back and as I approached it I could see Diane inside, sitting on a settee and reading a newspaper. She must have seen movement because she looked up and saw me and came out onto the patio area and waited as I came up to her. She was wearing a white, cotton blouse and a plaid skirt and she’d obviously spent some time on her make-up. I thought she looked good. No, that wasn’t the word. She looked old-lady-sexy, if there is such an expression.

‘Hello Stewart, welcome to my house.’ I followed her through the conservatory and into a big kitchen with a scrubbed pine table and oak dressers. She turned to face me. ‘Now come and kiss me.’

I went towards her and she put her hands on my shoulders and I put my arms around her and our faces tilted to each other and our lips met and we kissed long and hard, tongues exploring, lips mashing together, saliva mixing freely. Her hands went to the back of my head and she pressed my face to hers. My hands went to her bum cheeks and I pressed her into my erection and, to my utter delight, she squirmed her crotch against mine and dug her plum-coloured nails lightly into my neck. I rubbed myself against her, feeling her breasts against my chest and she broke the kiss and looked up at me her mouth still half open, her lipstick a red mess across her mouth.

‘Bloody hell, Stewart,’ she said in her cut-glass accent. ‘I can’t decide whether to drag you upstairs right now or to offer you a drink. I think on balance a drink might be sensible. We’ve got a few hours. At least, you don’t have to be anywhere do you?’

‘No,’ I confirmed, and a drink would be good.’

We drank white wine, in her big, elegant drawing room with its upright piano and oil paintings on the wall. ‘The conservatory’s better at this time of year but one or two of the neighbours can see in and I don’t want them to get the wrong idea. Or the right one,’ she corrected herself.

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