Another story from many years ago…
This took place while I was at a week- long conference in a mid-sized Canadian city. One evening after the training all of the people in our training group went out to get drinks and decompress. So far we hadn’t had a chance to get together like this so we collectively were all ready to let loose.
One of the girls in the group was named Carla and I could tell during the training that she had a crush on me- I would catch her staring at me or she would laugh a little too hard at my jokes. She was very nice but not really my type physically – although she had red hair, she was a little on the plump side and very over-sized boobs. Anyway, a nice girl.
During the night out, most everyone in the group got pretty wasted at a downtown bar. Most of the evening she was giving me these doughy eyes and always managed to be sitting near me. At some point the group got into some version of Never Have I Ever, not hardcore version, but with just enough racy questions that the erotic sensors in my brain started to kick on. And Carla was beginning to be more and more of my type as I downed pint after pint. She was definitely feeling it too, as she was now very obviously snuggling up next to me.
At closing time, the group all headed out back to our hotel. We were all paired with someone for our rooms, so neither of us had a private place to go, which posed a problem my drunk brain was trying to figure out how to solve. Carla and I were walking far behind the group, casually bumping into each other, keeping that physical connection. I was pretty sure she would be agreeable to wherever the night would lead, but I wasn’t sure where that would be given our lodging situation. But that didn’t deter me, and we started our own Never Have I Ever game, with every time we had done something, we would pinch the the other person’s ass. After several blocks of this, we were both fully ready for more touching than this. She asked where should we go, but I just kept on till an opportunity arose.
Not long after this, the answer appeared. I spotted a secluded part of the sidewalk that we might be able to slip away. The sidewalk split and went around a large planter box with a good-sized tree growing in the center. We walked to the side that was away from the street (but only a few meters away from the curb) and sat on the ground. It started as sloppy kissing but soon enough I had her massive tits out of her shirt and I was sucking and biting her erect nipples. Carla reached unbuttoned my pants and released my very stiff cock. She stroked it fast while I alternated between kissing her mouth and her giant rack.
I then pushed her gently down on her back onto the sidewalk, laid next her and plunged my hand down her jeans. Her pussy lips were flappy, but completely soaked. She started writhing under my hand as my fingers explored her hole and teased her clit. She had a hold of my cock the whole time and was working my drunk member into a real state. She and I got her wriggled out of her jeans, but only so that they we down to her knees. Her bare white ass was on the dirty sidewalk and her legs were spread just wide enough to open to me. I pulled my pants down to my knees and slid my cock in that desperate cunt. Her pussy was pretty loose and my dick easily entered, but fuck was it wet! Placing my hands on her shoulders, I started a rhythm, rocking up and down, filling her pussy deep till my balls were slapping her.
Carla was a pretty good moaner despite the publicness of our situation. Lots of “ooohs” and “oh yeahs”. Anyone walking by would have heard us, maybe they did and didn’t say anything, but the streets were pretty deserted at that time. Cars were passing by and in the illumination of the head lights I’d get glimpses of Carla’s face with her eyes closed enjoying the moment. We fucked missionary for a time like this and after a few minutes I revved up the pace, which changed her audible “oh yeahs” to louder “oh God”s. I pumped her hard like this, the sound of her very wet cunt adding to the noise of the scene. I still recall looking down and seeing her ample tits hanging out of her pulled-down shirt, watching them rolling around as I thrust in and out of her. After a few minutes of this, I pulled out just in time to blow my wad all over her shirt and some on her tits. I stroked out the last of it, my dick completely soaked in the juices of her cunt.
I laid on the side of her and we kissed and chuckled about the fact that we couldn’t believe what we had just done. We walked back to the hotel holding hands, her shirt stained with my cum. We acted like nothing had happened for the remainder of the week, but she was pretty tearful when we said our goodbyes at the end. My momento I took away from this were the very scuffed toes of my shoes from the shredding they took from the sidewalk.
Source: reddit.com/r/gonewildstories/comments/123r3uy/sidewalk_sex_mf