Caught spanking Jenny's bottom at the seaside

In one of my first posts I mentioned Jenny a sexy plump civil servant who was always up for a good hard caning followed by sex. Jenny stayed with me several times and we always made a point of going out shopping looking for school uniform items for her to present her bottom in. Jenny dressed smartly for our meetings, always a tight business skirt, high heels, proper stockings or stay-ups, and a thong, she reserved the big knickers for the school scenes we did.

During one of of our early meetings Jenny talked about shaving her fanny for the first time, so it was off to a local supermarket for some suitable razors, then the fun job of attending to her pubes until all was smooth. From then on she kept her bits super smooth. It was around then that she also wanted to give anal a go, so after a good caning to get her aroused we set to. I had a vintage glass pestle (as in mortar and pestle), with knob like ends, one big and one small. With some lube and some careful work with both ends of the pestle I was able to relax her bum enough to slide my cock in, Jenny loved it. Happy memories!

On one of Jenny's visits we headed down to the coast for a meal. It was a warm summer night so after eating we walked along the promenade, me teasing her chubby, shapely bottom with the odd smack. It never took Jenny long to get going and soon she was suggesting that she deserved a proper spanking. I guess it was around 9 at night, so getting dark, but still this was a public promenade with little privacy. Wandering on we found a neat little garden right next to the promenade, it might have had a bandstand in it. It was surrounded by well kept hedges just high enough to give some cover. Inside the garden we found a bench seat, itself screened by some hedging. This appeared to be the ideal spot. Seated I lifted Jenny's skirt and pulled her over my knees. Jenny had her normal stockings and thong on, so all of her chubby buttocks were on display. Jenny was the sort of woman who wanted a good hard spanking (or caning or slippering), no weak taps on her globes, so I set to walloping her plump rear until it was red. Neither of us thought at the time that spanking her big fat buttocks was a noisy business! Concentrating closely on this task I was aware that someone had walked into the garden until she actually walked right past us! As I looked up I caught the amused look and quick laugh of a woman, she looked like a well to do lady in her 50s or 60s. She must have had Jenny's spanking, and more or less nude buttocks, in view for a good ten seconds or more, and of course she heard it. She could have taken a different route out of the garden, but she had marched on right past us, probably less embarrassed than we were. I gave Jenny's backside a few more slaps and we then both decided it was time to head for my house for some privacy. Back home her smarting rear end received a thorough caning, before she lay back, legs apart, pussy sopping wet, for some attention of a different nature. And all the time me thinking of the mature woman in the garden and her laugh.

I've added this image, it's not of Jenny but her bottom is very similar in shape.





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Published by dagworth
6 years ago
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bingobob3018 2 years ago
Reminds me of a GF I had when I was about 30. She always wore stocking and suspenders (think that was part of the attraction to her by me ?), who once split a drink over me. She said she was sorry and I'd said it wasn't a problem, but she insisted that she deserved to be punished. I said ok and smacked her clothed arse three or four times.
That didn't satisfy her, so she told me in no uncertain terms what I had to do. So, I found myself lifting her skirt up above her waist and pulling her skimpy knickers down, before slapping her arse with a slipper that she had handy (oh yea !!)
Having given her six of the best, I felt that I had to offer her some comfort, so I began gently stroking her reddened arse and ever so gently working my figures down towards her pussy lips. Wow, was she wet !
She obviously enjoyed being spanked and it turned her on. I seem to recall that we spent a very energetic night fucking each other silly.
Happy days
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loves2watchwmuk
very erotic
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petdyke
petdyke 4 years ago
I'm much more into as smart :heart: as slender :heart: and best l<3 ooking like still under thirty ...
In my Mighty Mind they Always Are And Lots Less in age so to say, but butts by 2 :stuck_out_tongue_winking_eye: ! ? 
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tobiasj 5 years ago
to dagworth : No, after wiping it clean and returning it to its box you'd never have known, some slight discolouration to the wick, but not enough to tell the tale. 
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tobiasj 5 years ago
to dagworth : Yes, some of my favourite conquests have had plump bottoms. 
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dagworth
dagworth Publisher 5 years ago
to tobiasj : I trust you didn't tell these ladies "oh I've used this before on a bum hole, it's perfect"
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dagworth
dagworth Publisher 5 years ago
to tobiasj : I love plump bottoms for caning
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tobiasj 5 years ago
to dagworth : That's interesting, as I've still got the candle. It was a gift from a friend who'd been on holiday to Greece, a sort of church candle in a presentation box. I'd kept it in a drawer for years until I used it on Sally and a couple of others, each time returning it to its box. It's somewhere in my loft, nowadays.  
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dagworth
dagworth Publisher 5 years ago
to tobiasj : still got the pestle, it's perfect for bum holes!
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tobiasj 5 years ago
Jenny sounds amazing and with a bottom similar to the one in the picture, she must have presented a delicious target for a spanking or caning. Love the idea of you using a pestle to open up her anus, did a similar thing to a girl called Sally a few years back after giving her a caning. Would have used a pestle if I'd had one but used a candle instead. Sally too, had a large plump bottom! 
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dagworth
dagworth Publisher 5 years ago
to 210959 : Distant memories now, probably about 20 years ago. She insisted on being properly dressed for discipline and this included me, if I was in Headmaster role I had to wear a suit and tie. One weekend she came over and told me she'd been talking with a girl online who'd had about 150 strokes of the cane/slipper and strap over a couple of nights. Jenny wanted to outdo this girl so I was tasked to thrash her big bottom thoroughly, I think we got to about 200 strokes.
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210959
210959 5 years ago
oh my word ...you lucky spanker! and she was in stockings 
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spanka4on
spanka4on 6 years ago
to Glasgowsfinest : Oh yes, what an excellent, unforgettable time it must have been. I had a similar experience with a lady who enjoyed being spanked very hard (significantly harder than I'd normally spank actually) and she would orgasm several times during her spankings. She seemed to particularly enjoy being over my knee and receiving a fairly short 14" tawse. That blissful segment of my existence lasted about four months from beginning to end. Wonderful times, so I can certainly appreciate your experience. 
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dagworth
dagworth Publisher 6 years ago
to spanka4on : I've just replied to Jim with some thoughts of how it might have panned out.
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dagworth
dagworth Publisher 6 years ago
to Glasgowsfinest : What an experience, I do love it when women get all wet with a good spanking.
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dagworth
dagworth Publisher 6 years ago
to jimwebley : If only, but what an experience if it had taken place! The thought of Jenny and the woman both bent over the park bench, Jenny's thong round her knees, our friends sensible drawers at her ankles, both in stockings, the stranger gasping as my hand tickles her ample backside, Jenny yelping as her already glowing bottom receives more attention. And then both bottoms well reddened the stranger picks up her knickers stuff them in her handbag, turns to us asking "Perhaps you'd like to carry this on a bit further, my house's just round the corner...".
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Glasgowsfinest
Glasgowsfinest 6 years ago
Great wee tale. I went out with, very briefly, perhaps 4 weeks or so, with a lady who orgasmed ever time I spanked her bottom. It was the strangest of experiences. Not a woman orgasming, but the way she peaked immediately her bum was spanked. Looking back, perhaps I should have held onto her a little longer. She’s still my friend on F.B., but she’s married now. So there’s no chance of a reacquaintance. Pity!
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spanka4on
spanka4on 6 years ago
You have some cracking tales to tell...and I dare say, Jim's suggestion, although I very much Iike the sound of it, would probably have been too good to be true, if she'd have accepted the invitation!
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jimwebley 6 years ago
Perhaps you should have asked her to join you! It's certainly a germ of an idea for a sequel.   Xxx.
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