Missed Opportunity or Wishful Thinking?

Thought I would share this memory of mine from a few years ago.

My first ever job was working in a supermarket - stacking shelves, working the till etc.

Throughout my time there, I would develop camaraderie with some regular customers. Just friendly smiles and hellos, nothing more. There was one particular couple that would often visit. A middle aged, married couple. She was in her 50s, frumpy, and quite plain looking. He too was in his 50s (most likely older than her), silver haired, stocky and chunky. But the one thing I would always notice about him, was that he would wear various black leather jackets. All of them looked great. He wore them well. I knew exactly why he would wear them. He knew he looked good in them, he would turn heads from many of the female shoppers and workers. It gave him confidence, and I knew I wanted to be just like him when I was his age.

If you've read my bio you'll know that I admire older/middle age men who are fucking younger women. It's my favourite kind of porn to watch. I get so inspired by seeing these men fucking, sucking and bringing younger women to orgasm. It always makes me want to join in and have a threesome - spit roasting, double penetration/vagina/ass - of course only if the lady in question permits us.

Anyway, a few years after leaving that job, I met up with a bunch of buddies at a local pub for a few drinks. Partway through the night, I noticed a middle aged, leather jacket wearing man sat at the bar having a friendly conversation with the bartender. It was the same man who would visit the supermarket. And he was wearing his black blouson leather jacket - one of my favourites. Sat next to him, however, was not his wife, but a much younger woman. I'd say a good 20 years younger. Him in his late 50s, her in her early 30s. And she looked stunning. Beautiful. Hot. Initially, I didn't think too much of it until I noticed her hand was caressing his inner thigh. Rubbing the inside leg of his blue jeans (a great combo with a black leather jacket). He would also turn to her, smiling and chatting and at one point gave her a quick kiss.

I was quite stunned by what I was seeing. I don't condone adultery, and of course I have no idea what happened between him and his wife, but I could not shake this overwhelming feeling of adoration for him and his new stunning partner. I got up to use the bathroom and as I walked past them, her hand still caressing his inner thigh, he noticed me and nodded. I smiled back but quickly made my way to the bathroom.

As the night was coming to an end, I decided to take my leave. I said bye to my buddies and left the pub to walk home. As I was walking up the street, I noticed two figures locked in an embrace leaning against a shop window. It was the leather jacket wearing middle-aged man and his hot young partner. It wasn't a very public street, and it was late at night, so no-one else was around. As I got a little closer, I could see the full extent of their make-out session. It was passionate. So passionate that I instantly got hard. Her hands placed on his stocky, leather, back - feeling the leather, making it creak. I slowed down my pace as I didn't want to disturb them and ruin this moment. I kept imagining what they would be doing when they got home.

After a short while, they unlocked and started walking up the street away from me. I walked behind, but kept my distance, as not to interfere. However, he looked over his shoulder and noticed me walking up. He and his partner slowed down their pace so I could catch up. We had never really spoken before, so it felt odd that he would do this, but we entered conversation as we all carried on walking. Pretty menial stuff - my time at the supermarket, what i was doing now etc. No mention of his wife.

We soon hit a side street, which wasn't my exit. We all stopped and he said:

"This is us. We live down here."

"Oh right", I replied.

There was a slight awkward pause.

"So what are your plans for the rest of the night?", he asked.

Suddenly I felt overwhelmed. Was he hinting at what I hoped he was hinting at? I was still relatively young at this stage in my life and not overly experienced. But I had watched a fair amount of DP porn online, and knew what I liked. I also noticed that the young woman literally could not keep herself off him. Her head coyly resting on his shoulder. The top buttons of his shirt were undone. Her right hand was inside his shirt, stroking is visible hairy chest.

"Erm. I'm just gonna head home", I answered.

I don't know if I was imagining this (i was a little intoxicated), but they looked at each other and I could see their faces frown a little.

"Okay then. Well, have a good night", he said.

And the two of them walked off down the side street, her arm wrapped around his back. His hand gripping onto her tight little ass.

I was kicking myself. I didn't know how to answer. But one thing I did know, was that I was very hard. I quickly got home, whipped my cock out, and fantasised about those two fucking all night. I hope they did.

Even to this day, I think about both of them fucking, and I ask myself: "Missed opportunity or Wishful Thinking?"