A “WouldaShoulda” story is a moment from my real life where I made a decision that I later regretted or seriously wondered about. This is what might have happened if I hadn’t replied with a friendly smile, said “Good Morning,” and continued on my way. What if...

The subject of this WouldaShoulda I will dub “Duane”, since I have no clue what his name could be.

At the time this happened, I worked in a large city and lived on the outskirts. My daily commute included a walk from the subway station to my workplace. The path led past an outreach center for the homeless and there were often sketchy-looking people sitting around, but they generally behaved.

One morning, a tall Black man stood up as I approached. Naturally, I was on alert, but panhandling was just a part of daily life there. However, it turned out he was not looking for money.

He strode up to me and as he approached he dropped his pants and grabbed his cock with one hand and swung it back and forth.

“Look at this dick. You wanna suck it?”

Honestly, I did. Want to do that. It was mouthwatering. Even now, years later, I think back on that moment. Only fear of disease and arrest held me back. The fantasy played out in vivid detail behind my eyes.

Stylus scritching on a vinyl record...

I put on a friendly face and walked (quickly!) by while saying something like “Good Morning”. A few yards further I glance back and he was just ambling back to the door step, laughing and chatting with his friends.

But what if...

What if instead of walking past, I had stopped and spoken with the man?

I was lost in thought as I walked along the bustling city street, barely registering the people passing by or the cars zooming past. My mind was elsewhere when suddenly, a man stepped out from an alleyway directly into my path. Startled, I froze.