So, bad memories, where to start? I don't enjoy humiliation, it's not a kink of mine, so in the spirit of confessions, the title and over-sharing I'll go with this one.
They say it takes tens of thousands of hours of interaction for humans to reach an acceptable level of social comfort, or roughly to the age of 25. As a young man in my early twenties I had absolutely not reached that point. I was a perfectly happy child, rarely in the limelight and content with mostly solitary pursuits. I was never really much use with women, I never felt particularly comfortable with them and the memories are so very painful in hindsight.
I never did manage any experiences at college despite living my best life through IRC. So when I made it to London for a first real job I was determined to pursue my lifelong dream of submission. I did what any sensible person would do - I hit the message boards and with a remarkable degree of luck the first advert I responded to somehow landed a NSA attached date with an extremely attractive woman who was perhaps 15 years older than me.
Incredibly, she was for real. As attractive in real life as her pictures, and seemingly as enthusiastic as promised. We met on a Saturday morning in a smart Central London hotel. I was painfully awkward when I think back to it, but she complimented me for wearing a shirt as we made our way up in the lift to the room. I put my arm around her, it wasn't so bad, maybe this was going to be ok.
In her room, a small suite, she suggested I lie on the bed and she disappeared for a moment to change into the most gorgeous lingerie that years late I still don't think I've ever seen better. We see the past in rose-tinted glasses, but I can honestly say she was the most beautiful person I've ever been with. I had stripped down and laid back on the bed. She straddled me while I was still barely able to speak, we kissed, my hands in her hair, and then I realized that I could not get it up. She tried her best, and god knows it was nothing to do with her, but I couldn't get a response. She offered a handjob, but I was broken and I could maintain enthusiasm. I apologized profusely, made my excuses, and left, ashamed.
And so began a lifelong problem that I've still not managed to overcome. I'm sure it's psychological, but decades later I've never quite managed to overcome it. As bad memories go it's hardly the most traumatic, but of all the negative experiences I've ever had, whether personal or professional, this is the one that still hurts the most.
I never heard from her again, I look her up every so often, she's still stunning.
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