Jenny

Story Info
Senior flirting at checkout has unexpected result.
2.4k words
4.41
52.2k
21

Part 1 of the 2 part series

Updated 06/08/2023
Created 04/09/2017
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So I've got the bread, the bacon, the eggs, some fromage de chèvre and the inevitable salmon portions. They always come in twos so I shall have to have it two days running or put one in the freezer. I favour two days running otherwise the freezer fills up, as I forget to defrost stuff. Basket full enough, I set off for the check-out.

There is an old boy in front of me, actually he's about my age, but this queue has been chosen, as always, for conversation potential. I have chatted to this particular check out lady several times before, she brightens my day, and I freely admit that I go to the supermarket nearly every day and mostly for conversation, maybe even a little light flirting. Well where's the harm?

The check out lady could most graciously be described as mature, but then so am I: very mature. She has an open face framed with obviously newly styled hair, a light grey colour, curved in just below her ears. I cannot assess her figure but she is well presented, someone who obviously takes a pride in her appearance. I, however, am not! I'm, lets face it, a bit scruffy, old shoes, nondescript trousers, ordinary shirt and my uniform fleece: no Adonis!

The "old boy" in front makes a strange remark about the place being full of oldies, pays and departs. She rolls her eyes at me which opens the conversation. We talk about rubbish while she scans my items and I can't resist it, my mouth says. "Really great hair do."

"Well thank you, kind sir."

"No, I mean it, it really suits you."

"It's not best presented in a supermarket overall."

There is no one behind me so I revel in the moment, lean forwards and say,

"I'd very much like to see it better presented."

"I do believe you are flirting with me, kind sir.." As she adjusted her hair.

Even I can read this sign, two 'kind sirs' in two minutes and the old hair preening gesture.

"I certainly am, and I'd consider it a honour to take you for a pub supper."

Shit, my mouth always works faster than my brain. I'd just let it run away. What if I get rejected: simple, choose a different check out for a while.

"Actually, I am available on Friday."

Did she really say available rather than free? Am I reading too much into this?

"How about the Bell at seven thirty?" My heart stops for the reply.

"The Bell, 7:30 on Friday it is. I'm Jenny by the way."

"And I'm David. So see you Friday Jenny and don't change the hair!" I leave with a smile which is reciprocated.

What have I done? I'm bloody sixty seven year old. I've just hit on a pretty girl (any female younger than me is a girl, it's just an expression, she is probably only a few years younger than I am) and she's accepted: wow. The week drags, I cannot even bring myself to flirt with other check-out ladies. I am behaving like a teenager. It's only a pub supper. Yes but it's a date: a date!

Eventually Friday arrives, the morning drags, the afternoon drags. For goodness sake, we'll probably just have an agreeable meal, the Bell is always reliable, run out of conversation and part in an embarrassed silence.

"David?"

I turn towards the voice. She looks stunning. I recognise the face and the hair do but the rest is a surprise. She is average height, not overweight but 'generous' in the hip department, wearing a loose flowing dress and a little bolero style jacket. She looks marvellous.

"Jenny! Delighted to see you, come on, sit down. You look wonderful, so much better than that orange uniform!"

"Hey, too many compliments for an older lady: stop it, I love it!"

We sat down, chose a Malbec, ordered our food and got to know each other.

It turned out that we had both been on our own for some time and enjoyed the simple pleasure of day to day interactions with the opposite sex. I was not expecting the question when it came.

"So David, kind sir, do you do this sort of thing all the time?"

"No, not at all." I managed in an embarrassed stammer.

Her hand reached across the table, covered mine while she said.

"It's quite OK," she cooed. "You're single. You can do exactly as you wish. Anyway monogamy is overrated."

What did she just say? Can I believe my ears? What the heck do I say now?

"Er," stammer. " You are probably right."

"Of course I am. It's a learned behaviour, not natural at all. Look, why do you always flirt with me at the check out? Because you liked the look of me and probably had a mild fantasy about what might happen. Well, why did I respond? The same reason. I didn't respond to all the other men that day, just you. I felt the same. Now we know each other a bit we can either faf about all evening or go somewhere and get to know oneanother."

Shit, I think I just grew up! It would appear that all that leisurely seduction stuff of my teens was now as out of date as my dress sense.

"Would you care for a coffee, chez moi?"

"Coffee yes, brandy perhaps, then we'll see."

I paid, returned to the table, offered my hand, she took it, we went to my car hand in hand like teenagers. Très emoustillant!

During coffee, with brandy, we chatted about our various interests, previous liaisons and a few risqué tales, when she dropped the bomb shell.

"Look David, I really enjoy your company and the meal was delightful, so where do you want to go from here?" Putting her hand over mine again.

"I really enjoyed it too but I don't want to spoil a new friendship by rushing." With that she leaned forward and kissed me gently on the lips. I didn't need any further encouragement and wrapped my arms around her and kissed her deeply, our tongues darting in and out of each other's mouths. To feel the warmth of her body flowing through the thin fabric of her dress, as her generous breasts pressed into my chest, was fantastic.

"Show me round your home," she breathed. I had never met such a delightfully open woman. My upbringing had been very reserved and I guess I hadn't changed much in the intervening half century. I wasn't used to being led, particularly by such a confident woman, but I took my queue, stood up, took her hand, pulled her towards me. We kissed again. I ran my hands over her hips and down over her yielding buttocks, then escorted her to my bedroom.

She was definitely a leader. She pushed the door shut with one foot and slipped into my arms, for another languorous embrace.

"So, kind sir, I do believe you have managed to get me into your bedroom, with the door shut! Wicked man. I wonder what your intentions are now, I do so hope they are not honourable!"

By now my intentions were far from honourable. My imagination was running riot, not just the old cerebral cinema of what could happen, but images of what was almost certainly going to happen. My cock started to stir in my pants. We embraced again as I massaged her buttocks through the thin fabric of her dress and I felt her hands move towards my belt.

There are few more erotic sensations in this world than having a woman undo your belt. The anticipation is exquisite: you both know where this is going.

The belt was undone and I sensed the familiar vibrations of my zip being slowly lowered and she gently started to rub the outside of my boxers as my cock swelled appreciatively.

"Mmmmm, nice. I think someone is pleased to see me!"

She tugged my trousers, which slid to my ankles, knelt down in front of me, pulled open my pants and allowed my stiffening cock to escape. Taking me in her welcoming mouth she started to suck and lick. It had been years since I'd had a blow job and my cock quickly rose to the occasion. She continued until my erection was as proud as it was ever going to be.

"Right, kind sir, time for you to pleasure me." She slipped the sleeves of her dress over her shoulders and let it fall. Now I could see why her embrace was so warm: no bra, just a magnificent pair of full, pliable, mature breasts terminating in large pink nipples, surrounded by even larger darker areolae. Who could resist? I buried my head in them and sucked on those delightful nipples in turn. They quickly came to attention and stiffened in my mouth.

"It's no use pretending I don't like that then." She quipped with a mischievous grin. "I like them sucked and really quite hard, as hard as you like just no biting."

I carried on for a few minutes and, judging by her breathing, she was really into it. Then I worked my way down, over the soft, yielding flesh of her stomach to her navel and a vertical scar where the flesh was a little puckered, so probably an old caesarian? The scar led down into her pants, not a thong, not a tanga, nor even just plain cotton panties but those delightfully erotic looking, loose fitting, french knickers; in silk if you please, hanging gently over her hips and concealing the delights below.

What a delight! I took the helm of each leg and pulled slowly: very slowly, savouring each second. My excitement built as I gradually revealed more and more of her lower belly. I find the delightful outward curve of the mature female belly highly erotic and my cock was certainly appreciating the sensation of my lips running over her. The more I lowered the more it became obvious that Jenny liked to keep a smooth pussy, and this was eventually confirmed as her delightful cunt finally came into view for the first time. Completely hairless, smooth as a baby's bum, not shaved, definitely not shaved, but waxed.

"Surprised?" She said as she sensed my intake of breath, "Well no-one likes a mouth full of hair do they?" Can this lady be so open? It was delightfully candid, so totally sexual. We weren't even fully undressed yet and she had intimated that she wanted some oral attention. I took the hint. Now wearing only her holdups and a cheeky grin, I laid her gently on her back, on the bed, with her knees bent over the edge. I gently spread them and knelt down on a pillow to admire this beautiful, mature, confident, naked woman and her completely bare pussy.

"Oh, wicked sir, are you about to show me what you can do with that tongue? Are you going to be kind to my smooth pussy? Are you planning to kiss it, to lick it? Take it slow and I promise you a real treat."

I did as I was told. A hint of moistness was already starting to show between her legs as I started slowly. First I licked her inner thighs, then her pussy lips, sucking them alternately deeply into my mouth and as they started to swell and open naturally, I turned my attention to the petals of her inner lips and on up to her clit. Slowly it started to emerge from below its hood and I drew it into my mouth. She became more animated and much more vocal. I find a woman being noisy, during sex, incredibly arousing and the more I licked and lapped the noisier she became until she tensed, her belly muscles started to quiver, as did her buttocks. Then she shuddered and I guess she came.

There is little more stimulating than having a woman orgasm on your tongue and my cock responded accordingly. I slid up her supine body towards her face, my rigid cock feeling its way to its natural destination.

"You'll need a condom to go any further," she breathed, "are you a boy scout: prepared or am I just going to have to suck you?" I hadn't expected things to move this quickly but luckily I had a packet, in the bed side drawer, from a previous encounter that hadn't gone as well as I'd hoped. I grabbed the foil package, tore it open and slipped one on.

"OK, mr scout penetrate me: fill me: take me."

"God you're so sexy, so frank."

"I talk really dirty too, but I don't want to shock you."

"You won't." I said sliding my erection up to the entrance to her pussy.

"Then fuck me, kind sir. Stick your cock in my nice wet cunt and fuck me slow but firmly."

We enjoyed some missionary for a while and I got seriously turned on watching her thrash about under me before she took control and rolled me over onto my back. She straddled me, one knee either side of my hips and then lowered herself slowly back onto me.

She rode me cowgirl, with my cock deeply embedded in her warm, wet, pussy. She knelt up and straight and rocked her pelvis against mine. The sensation was wonderful as she forced her clit against the base of my cock. Then she started to breath more quickly, reached behind her to take my balls in one hand and massaged them. This is something I am not used to and very quickly I got that well known feeling of approaching the point of no return. It starts in my toes and runs up the inside of my legs. I know that when it reaches my inner thigh the result is inevitable.

I felt her pussy squeeze my cock. I went over the edge. My muscles spasmed and I came with several powerful contractions.

"Oh fuck, that was good." Jenny sighed, collapsing on top of me. "Fucking great. Tell me a sexy story, your wildest fantasy while I rub myself on your dick. I want to come again." She rubbed. We talked. Swapped sexy stories. She rubbed some more. We giggled. She got noisy. She came. I felt my cock shrinking. I withdrew, shed the condom and we cuddled for a while.

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5 Comments
oldtwitoldtwitover 2 years ago

This could so be real

chytownchytownover 3 years ago
Now That's Mature Sex****

Damn good read! Thanks for sharing.

shoeslayershoeslayerabout 7 years ago
Very nice!

I sure enjoyed this delightful story,

having been married to a lady 27 yrs older

than I for twenty years, I can't agree more

that older ladies are great. I like the way

Jenny knew what she wanted and how

nicely she went about getting it. I'll be checking

for more of your stories!

AnonymousAnonymousabout 7 years ago
Senior sex

Nothing like senior sex! My wife is 60, I'm 68, and every time we hit the sheets the results are earth shattering! I could never have imagined sex at this age would be so fantastic! Climaxes for both of us are unreal, she convulses for a couple minutes every time and the way she makes me explode leave me more satisfied than any other time in my life!

AnonymousAnonymousabout 7 years ago
It's nice to have woman in your bed

Great story - nicely told with a senior wit and appreciation. Tell me, does she have a sister?

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