I was shivering on the cardboard in the alley behind the 24-hour diner when he found me. Rain had soaked through my thin hoodie and jeans, making everything cling to my skin like a second layer of misery. My stomach was empty, my pussy even emptier, and I was desperate enough to do anything for a warm bed and a meal. When the tall guy in the leather jacket stopped at the mouth of the alley and looked down at me, I knew exactly what he wanted.
"You look like you need help," he said, voice low and rough. "How bad do you want it?"
I crawled forward on my knees, not bothering to stand. "Bad enough to suck your cock right here if you want."
He unzipped without another word. His dick was already half-hard, thick and veined, the head flushed dark. I wrapped my lips around it and sucked hard, tasting salt and skin. He grabbed my wet hair and fucked my mouth in short thrusts, pushing until my nose hit his zipper and I gagged. Spit ran down my chin and dripped onto the wet cardboard.
"Get up," he ordered after a minute. "Turn around and pull those jeans down."
I did it fast, shoving the soaked denim and my panties to my thighs. The cold air hit my bare ass and cunt, but his hands were hot when he spread me open. Two fingers shoved straight into my pussy without warning. I was wet already, desperate and slick, and he laughed low when he felt it.
"Fucking soaked for it, aren't you? Homeless little slut needs a cock that bad."
He pulled his fingers out and replaced them with his dick in one hard thrust. I cried out, bracing against the brick wall as he started pounding me. Each slam drove me forward, my tits scraping the rough surface through my hoodie. He reached around and rubbed my clit in tight circles while he fucked me, making my legs shake.
"Don't you dare come yet," he growled, pulling out and spinning me around. He pushed me to my knees again and fed his cock back into my mouth, making me taste my own juices. I sucked greedily, hollowing my cheeks, until he yanked me up and bent me over a stack of crates.
This time he took my ass. Slow at first, working the head past the tight ring, then deeper until his balls slapped my pussy with every stroke. It burned and stretched and felt so fucking good I started pushing back against him. Rain kept falling, running down my back and between my cheeks, mixing with the mess we were making.
He reached under me and fingered my cunt while he railed my ass, two fingers, then three, curling them until I was shaking and begging.
"Please, let me come. I'll do anything."
"Come on my fingers then, you desperate whore."
I came hard, clenching around his cock and his hand, my whole body jerking. He kept fucking me through it, using my ass until he pulled out and painted my lower back and ass with thick ropes of cum. It felt hot even in the cold rain.
He zipped up, tossed me a twenty and his jacket. "There's a motel two blocks down. Room 7. Be there tomorrow night if you want more."
I stayed on my knees in the alley a while longer, cum cooling on my skin, the money clutched in my fist. My body ached in the best way. I was still homeless, still broke, but for the first time in weeks I felt full. And I already knew I'd be waiting in that motel room tomorrow, ready to take whatever he gave me again.
