There’s this alley I walk through every day to get to my apartment block. It’s not a very safe looking place. But it’s the fastest way to my apartment. There’s this homeless man who is always there. Let’s call him Greg. He’s, around 55 or so, and I see him almost every day. Over the months, we’ve had basically no interactions, except a polite nod or smile if we ever make eye contact. And a few times I’ve given him some change.

The first time Greg ever actually talked to me was a few months ago. He was drunk and slurred out, “Let me see them tits!” It freaked me out, but he didn’t try anything, so I just kept walking. A month later, he talked to me again, something along the lines of him being happy he gets to see me everyday. I didn’t really know how to respond, so I just nodded and moved on.

Then, a few weeks ago, he was drunk again and said I was “a hot piece of ass” and he wished he had someone like “me in his life”. He kept talking until the end of the alley. Quite crude and explicitly.

A few days ago , it was really late when I back, much later than usual. The alley was quieter than normal, no humans around, just traffic noises. Greg was there, in his usual spot, except leaning against the wall, and at first, I thought he was asleep. His head was drooping, and his eyes were fluttering. But he wasn’t asleep because he opened his eyes and he said something to me along the lines of “you fucken walk past everyday and never show me your tits”

For some reason, I stopped. I don’t even know what came over me, but I just felt like I should let him see my tits. I lifted my shirt and let him see my tits. It was such a random, impulsive thing to do, and I still don’t fully understand why I did it. But I did.

He just stared at me. I froze. I didn’t know what to do. We stood there for what felt like forever, and then he smiled and said, “Thanks, beautiful. I’ll be thinking of this tonight. You’ve made my day.”

I smiled awkwardly and went to pull my shirt back down, but then he said, “Can you keep them visible while you walk away?” I don’t know why, but I did it. I walked a few more steps with my shirt up completely exposed and nervous someone else might see me.

Before I got to the end of the alley, he called out again: “How about a look at that pussy?” I didn’t say anything or turn around. I just kept walking, and as I reached the end of the alley, I heard him say, “Maybe tomorrow then…”

That was a few days ago, for the next 2 days I just walked past him ignoring his requests to see my tits and pussy this time. Today he practically begged… The thing is, I don’t know why, but I’m considering letting him have a quick peek at my pussy too. The thought is very exciting for some reason.

I’ve even started thinking about how I’d do it. If I’m going to go through with it, I want to feel confident about it. I’ve been thinking about getting waxed, maybe leaving a landing strip. It’s a weird detail to focus on, but it makes me feel like kinda excited thinking about it