At least the shitty night was ending on a better note. After being stood up and embarrassed in public I did not think anything would cause my frustrations to ebb. But then I got to, serendipitously, follow you. I wasn’t following you purposefully, you just happened to be in front of me walking. But that didn’t stop me from watching you. Small build, a tight ass contained in a short skirt. Midriff out for the world and a tight top to contain your small chest. I watched your ass sway as you walked, less than elegantly, in your heels.

Maybe you were on your way home from a bar or date. Something that turned out better than my night. Maybe it was a girl’s night and you were the last straggler heading home. Who knows what the situation actually was, but I had fun imagining and forming plots in my head about your night out. It helped that your ass rocking back and forth was such an inspiration. I wanted to get closer, and see if I could catch a glimpse of what was underneath. But I did not want to startle you or cause you concern. There is no harm in looking after all. As I was playing the game of how close can I get I saw you stumble. Tripped over something on the sidewalk. You were going to go down when I instinctually reached out. I caught you by the upper arm and pulled you back to your feet.

Looking back at me shocked, your mouth opened in surprise and disbelief. A meager ‘thank you’ escaped your lips without your thinking. I don’t know what it was. Maybe the look in your eyes, maybe all the situations I had imagined you in, maybe I was just having a bad day and wanted to take it out on someone. But I didn’t let go of your arm. Rather, I pulled you into the ally that was adjacent to us. As secluded as an ally could be, I took you behind some boxes and pushed your back up against the wall.

“You want to thank me? Don’t scream.” I told you while I placed a hand on your shoulder and forced you to your knees with one hand. You willingly dropped down, the surprise and disbelief turning to fear in your eyes. With my other hand, I undid my pants and pulled my mostly hard cock out. I moved my hand from your shoulder to head, grabbing a fistful of hair. I pulled your head closer to my waiting cock. I did not even have to direct you, your mouth opened on its own to take me inside. You seemed almost willing to open your mouth for me. My trepidations of you biting my cock soon replaced with the pleasure of using your soft wet mouth. I thrust inside and back again, and you dutifully kept your mouth open and accepted every inch I gave you.

Slight gagging but never resisting or fighting, I used your mouth and throat for my enjoyment. Looking down on you to see you focused clearly on the cock that was abusing you. I didn’t even need to hold your head anymore, you started to move back and forth on your own. Your acquiescence only made it better for me, I liked a woman who knew their place. I could feel you start to fall into a rhythm, sucking and working your tongue around my hard cock. But my curiosity got the best out of me. I had spent most of the time following you wondering what color your panties were, and I was going to find out.

I pulled you up by your hair and spun you around. Hands bracing on the rough brick all in front of you I slid up your short skirt to reveal a possibility I did not imagine. No panties, nothing underneath that short skirt as a barrier to the world having its way with you.

I was going to teach you a lesson. I lined myself up behind you and slid my cock deep inside your exposed pussy. I slid completely in, to the base. It felt amazing, you were already so wet for me. You must have enjoyed sucking my cock on your knees in a dirty ally. I started to pump into you. Using your willing hole for my pleasure. I could feel your body respond to me. Your legs got shaky, and I wrapped an arm around your belly to hold you up. I heard you start to gasp and moan as I thrust repeatedly inside of you. Your sounds of ecstasy driving me to say things I would have never normally uttered.

“You like being raped you slut?”

“How does it feel to be nothing but a set of holes?”

“You’re lucky I only want to use you.”

And other degrading things came mindlessly from my mouth. I wasn’t going to last long. The thrill coupled with your willing body was driving me to my breaking point. I was going to cum deep inside of you. I could feel myself getting closer with each thrust. I wanted to fill your pussy with my cum. Holding you tightly by your waist, I pulled your ass into me and shot load after load of hot cum deep inside your womb. I felt you shake and quiver under the sensation. And after I had completely emptied my load inside of you, I dropped you to the ground. You collapsed in a heap of heavy breathing and sticky juices. You looked up at me.

“T-t-that was the first time.” You said shakily.

“What?” I respond.

“I walk this street every night wearing this outfit, hoping someone will take advantage of me like you did.” I could not believe what you just said. I tucked my now limp cock back into my pants, gave you one last look while you were a mess on the ground, and turned to walk away. Maybe I would start more late night walks from now on.