This is a weird story; check out the tags for more info. Enjoy!
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As he walked home from work at two in the afternoon through the sparsely populated streets, he kept peeking inside every alleyway he passed by, wondering if anything was inside. It was a fairly safe city, but he always liked to keep an eye out for danger. Why not?
He turned to his right and looked into the next alley. Barely eight feet wide, but well lit by the overhead sun, it was flanked by orange-brown brick on the left and mostly windowless concrete on the right. It took a ninety degree bend further down, and he saw some graffiti and--
--He bumped into something that felt like hoodie-covered jelly, and his reflexes saved him from tumbling into the rest of it.
"Oh! Sorry!" he said, looking down apologetically and backing up before even looking at who he bumped into. She was wearing... short yellow boots with black shoelaces, which were a weird fashion choice, but nothing too absurd; he quickly brought his eyes up her body, past her thick, fluffy gray skirt, and up to her oversized, partly unzipped gray hoodie with... a yellow necktie between her big...
He took his eyes away from her generous cleavage. It felt like every time someone surprised him, he always reacted in the worst possible way...
"Sorry, sorry," he said, looking her in the eyes. His heart pounded as he wondered if eye contact was a bad idea given the circumstances. She seemed to be staring back at him, and he didn't know if that was good or bad. And were her eyes different colors, or was it just the light? One brown, one hazel. And her blonde hair was a little too yellow. He resisted the urge to ask if she put in the wrong contact lenses; as for her immediate reaction to the bump and everything he did, he was relieved that he seemed unbothered.
"Oh, hi there," she said in a bubbly voice, holding up an arm and waving her hand like she was saying hello to him from fifty feet away. Then, she giggled. "It's funny that we bumped into each other, isn't it?"
"I guess?" he said.
She went back to a neutral expression. "It's like we were meant to do that. Anyway, I heard that guys like it when girls give them handjobs... Is that correct?"
It took him a moment to process what she just said. He looked around to vent the shock as well as see if anyone else was around. Nobody was nearby; the streets were basically empty, except for some people walking on the opposite side of the street half a block away. He looked at her as she stared at him, seemingly expecting a response.
"I, uh... yeah?" he sputtered.
"Whew! I was worried I was wrong for a moment," she said, dramatically wiping the nonexistent sweat off her brow. "Anyway, interested?"
"Interested in..." Suddenly, it made sense. She was probably just a prostitute being a little pushy. "Oh, no thank you, I don't have money to spare, and also I, you know, sex work's cool and all but it's not my thing..."
"Money? I didn't say anything about that. I just wanna jerk you off," she said blankly, then she gave him a wink and a smile. "Besides... When's a girl with boobs like these gonna ask you again?" She put her hands on the underside of her breasts, the fabric of her hoodie shifting as she jiggled her chest.
Yet, as strange as this all was... A flush of warmth went through his body. He wasn't seriously considering it, right? Right?
"Oh!" she said, pointing a finger upward as if she had an idea. "I thought it was obvious, but we're going to do it in that alley over there," she said, then pointed towards it. "By the way, guys like kisses, right?"
He was stepping towards the alleyway. Even though part of him really didn't want to do that, she did have nice boobs... Somehow this didn't feel like a trap. If this were a trick, surely she'd be less... weird.
"I, um..." he stammered.
Maybe this wouldn't turn out so bad after all. She was, after all, just weird.
She was waiting for him to say something, so he relented. "Yeah, yeah, kisses are great... So uh, lead the way I guess?"
"If you need me to, sure!" she said. She winked and gave him a thumbs up, then turned towards the alley with an almost startlingly quick speed, looking straight ahead blankly as she walked into it at a slow pace.
He followed her with a little hesitancy, looking around as they walked. It was at least a fairly clean and trash-free alley, with nothing more than a little dirt gathered in the edges where the walls met the ground. She led him past a couple of trash cans, and around the ninety degree bend.
No windows overlooked the part of the alley past the bend, and the sun was still shining bright overhead. It was largely barren except for some tall, four foot wide wooden crates that were pressed up against the left and right walls at various spots, and he felt oddly alone in the tiny maze. She led him past a couple of the crates, and stopped right in the midst of two stacks of them, with a six foot wide gap in between the tall stacks.
"Now," she said, "Just lean against the concrete wall and I'll show you a good time..."
He nervously obeyed, pressing his back against the slightly warm concrete. She came closer, boxing him in, and she went from a blank expression to a sultry, almost predatory smile.