Chicago

It Starts With A Fall

Sam

My friend Molly and I were running down Wacker Drive, nearing the 2 mile marker of the Shamrock Shuffle, an annual 8k race through downtown Chicago. We’d been running together every March since we were 16, now seniors in college and roommates.

“Let’s grab some water,” Molly panted as we approached an aid station.

“Ok,” I agreed, following her lead to veer towards the left side of the street where the volunteers had tables set up. I assumed the plan was to just grab a cup from one of the volunteer’s outstretched hands as we jogged by, but apparently Molly had another idea. She left my side suddenly to come to a full stop at the water table, double fisting water cups.

“Molly, what the hell?” I muttered to myself, doubling back.

I turned to cut over to the sidewalk and out of the way of the other runners, not noticing the guy coming up on my left, attempting to pass me. He collided with me suddenly, which sent both of us stumbling.

“Ouch!“ I yelled, more a knee jerk reaction than a response to pain. I recovered quickly, realizing I wasn’t actually hurt. “Shit, I’m sorry! I didn’t see you coming!”

“Oh my god, I’m so sorry! Are you okay?” he said at the same time, his hand on my arm as he braced himself.

I would’ve expected him to be annoyed with me for getting in his way, or not paying enough attention. But when our eyes met, he just looked genuinely concerned. I couldn’t decide whether it was better or worse that he also happened to be really cute.

We both started laughing. He removed his hand, and I felt its absence. It looked like he was ready to take off again and continue running, but something was holding him back.

When I picked up on that, I decided to act on it, feeling a strong and sudden desire to keep him there. So, in my awkward way, I attempted to flirt by making a self-deprecating joke - something about being a human hurdle that I blocked from memory as soon as the embarrassing words were out of my mouth.

Again, he just laughed and told me not to worry about it.

“Well, you’re very nice,” I said. Then, furthering my attempt to stall him, I offered to “treat” him to a cup of water. “It’s the least I can do. Unless I’ve already messed up your race time enough?”

He smiled. “Nah, I’m not really concerned with that.”

I smirked and blushed, happy to hear him going along with my obvious ploy. “Do you want a water, then?” I gestured behind us to the table as the other runners continued to dodge around us.

“Sure.”

I was more careful to watch where I was going this time as we backtracked towards the water tables. I grabbed us a couple of cups and handed one to him.

“I actually don’t remember the last time a pretty girl offered to get me a drink,” he flirted. “I like it - it’s a good move.”

My laugh was louder and more bubbly than usual. I mentally slapped myself and told myself to get a grip. “Oh yeah, I’m full of those. Clearly.”

He laughed with me.

Molly finally caught up then. “Okay, I’m ready,” she stated, then noticing the handsome stranger I was chatting with, her expression turning curious as she said hi.

“This is my friend Molly,” I said. “And this is a poor unsuspecting runner I almost took out trying to stop and wait for you to drink a gallon’s worth of tiny water cups.”

We all laughed together, my new friend and I taking our last sips and discarding the cups. I knew I couldn’t stall any longer. It was time to move on.

“Good luck making up your time,” I said, giving him permission to run ahead of us.

“Yeah, we’ll see,” he chuckled. Then he winked at me as he said, “Thanks for the water,” and I felt a tingle spread through me, from my nipples down to my pussy.

And with that, he continued running, and so did we.

“He was cute!” Molly said once the guy was out of earshot.

“Yeah,” I agreed easily. “I guess I should thank you for drinking like a camel.”

She laughed, and we continued on our way.

The next water station was almost 4 miles into the race. I knew Molly would want to stop again, so I was already planning on it this time, looking behind and around us as we made our way over. I was so busy checking my blind spots; it took me longer than it should have to notice him standing there.

“Isn’t that the guy from the last water station?” Molly asked.

“What?” I said, glancing at her to see where she was looking, and then following her line of sight to the water station. And there he was, standing amongst the volunteers handing out water, smiling, with two entire bottles in his hands.

I couldn’t help smiling back right away, feeling a flutter in my stomach, excited to see him again.

We jogged up to him, and he told us he’d talked the volunteers into giving him the full bottles, knowing the flimsy ½ filled paper cups wouldn’t do the trick for us.

It was enough to win Molly over. “You are a genius!” she exclaimed, thanking him as he handed her one bottle. She took a big gulp right away, then said, “I think I’m gonna take a minute to stretch over there,” giving me a quick look and raising her eyebrows as she jogged away.

I knew I was friends with her for a reason. So, the sexy runner and I stood off from the water station to talk some more.

“I hope you weren’t waiting that long for us to catch up?” I said, then taking a sip of water.

He shook his head, “No, not long at all.”

“Are you running with anyone? Some poor unsuspecting friends that you ditched to serve water?”

He chuckled. “No, I’m just running with a group of coworkers. It’s like a company team building type thing, I guess. But no one I was running side-by-side with or anything.”

“Oh, okay,” I smiled.

“Anyway, it was kind of fun waiting and watching for you. And even more fun enjoying the view as you ran up. Now I’m feeling pretty tempted to follow you the last mile to enjoy the view from behind.”

Fuck. I felt heat rush to my cheeks when he said that, and I hoped that it just looked like I was red from the run. My throat suddenly felt dry, so I took another sip of water, trying to hide my grin, biting my lip when I finished drinking to hold in the nervous laughter.

He kept looking at me, his eyes roaming over me and then returning to meet mine. His gaze was intense, making me wonder what all he was imagining, or picturing. I had to force myself to maintain eye contact, feeling overwhelmed, my pussy suddenly throbbing, wondering if he could notice my nipples hardening through my shirt. Neither of us said anything else. We didn’t need to.

Molly came back over soon. “Ok, I’m ready if you are.”

I snapped out of it, finally. “Yeah, okay,” I agreed.

We thanked him again for the water bottles.

Then, as we got ready to continue the race, he said, “I’m gonna hang back another minute or two to see if one of my co-workers will catch up.” I noticed his slight grin and wondered if that was just a story, for Molly’s benefit.

We took off jogging again, and I tried not to be too obvious as I peered back at him over my shoulder. Sure enough, I caught him watching us running, smirking. I blushed harder and smirked back.

I wasn’t sly enough - Molly noticed me looking. “Okay, tell me you got his number?! He’s totally into you!”

I just shook my head, but my smile must’ve given me away. “No numbers. Not even a name.”

“Samantha, what the hell?!”

I shrugged dramatically. “You know how awkward I am! What do you expect?!”

“You better hope you have another shot at the finish line! And you know I will make the move for you if I have to!”

I laughed, but didn’t argue. I was thankful for Molly’s pushiness, knowing it was usually what I needed.