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 quickly 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.

The “me” in the story could be a man or a woman or anyone else interested in giving head to a penis. Duane is an adult, black male with a massive schlong. You are who you are.

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?”

My eyes locked on his penis. It was honestly breathtaking. An amazing and just fucking lovely cock. Thick without being scary and it was long. He was maybe half hard. Enough that I could see it was really nice, and his tip was just emerging from his foreskin. Glistening.

Imagine hearing the sound of a stylus scratching across a vinyl record...

I put on a friendly face and walked (quickly!) by, saying something like “Good Morning”. A few yards further I glanced back, and saw him ambling back to his community doorstep, laughing and chatting with his friends.

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

I stopped abruptly, stunned at being confronted so blatantly with a Big Black Cock in the STREET of all places. My eyes locked on his penis, and I mumbled, “Hi. Um. That’s a nice cock there.”

His eyes shifted from arrogant and braggy to a little unsure. “Thanks,” he said, waving it slowly back and forth. I think he expected me to run or scream or something.

I hesitantly reached out my left hand, palm open and up. “May I ... touch it?” I asked, my voice a little quavery as I suspected this was going to turn out to be a poor life choice.

He nodded, looking even more nervous. We were gathering a crowd, but it was all the vagrants – his friends - hanging out there at the time. No one would see this happen but them. And him.