There's been a few...
But I think this one wins out!
This happened 20-odd years ago and was the result of a lot of online exchange between me and another guy who was proudly 'training' his submissive.
We'd had a lot of correspondence and clearly had a lot in common. He was obviously far more experienced (in R/L) than me and to a far more extreme extent in that not only was he sharing her, he was actively involved in group activities and if I say they weren't walking their dogs, you'll perhaps get the memo?
An occasion emerged when we'd have the opportunity to meet. Sounds strange perhaps but C & K lived in very North Wales (by the Electric Mountain) and I live in very central England (very close to the last big power station to recently close).
By UK standards, it's a bit of a trek!
As things happened, I was working in Wales and could take a different route back which meant we could meet.
C was all over it and well up for it but it wasn't all plain sailing (or driving!). Traffic was bad, I was delayed, nearly binned the car at one point and by the time I finally arrived, I really wasn't in the mood for much.
More unfortunately than that, when I met K, I really didn't fancy her either. I don't consider myself a snob particularly but her place was more than a bit squalid (which also dampened things considerably) but for her part, she'd been kept (literally) hanging around for quite a while and it was pretty sure she'd lost what interest she had too.
Nonetheless, C was still very keen to get things cooking, insisting that she address me as Sir ..... (which I find really cringey!) and took great delight in stripping her naked for me.
Next fail: K had very obviously spent a lot of time in shoes far too tight or small and one thing that really kills the thrill for me is damaged/deformed feet!! Oh well, man up....
So she's naked between us and C is doing all kinds of rude things to her. I will say K had very nice tits but when I picked on up by her nipple, she really didn't like that and made that abundantly clear. Another downer!!
"Do you want a condom?" I was asked. Now things were really starting to feel contrived. As if it wasn't bad enough already, I knew there was very little chance of me making use of such a thing and politely declined, pointing out that my cock was already buried in K's mouth while C fucked her from behind.
What really fucked things up big time was his bloody black Labrador, constantly fussing around the whole thing and very clearly desperate to get involved!!
I can't remember clearly past that point other than the dog didn't get a go and neither did I! I really wasn't interested at all by then and I think things just gently crumbled as politely as we could manage and I left.
What I did find ridiculously ironic was that many years later, LinkedIn suggested K as someone I might like to connect with!! Considering we'd never exchanged any correspondence or communication and LinkedIn only (theoretically) 'knows' my personal and professional emails (neither of which I'd used for 'private' purposes), I thought that really showed the extent to which social media secretly mines its way into your life and those around you, no matter how tenous the connection!!
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When I say 'older women' that's older than me, not just my daughters!
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