It Starts With A Fall (Chicago #01)

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 you coming up on my left, attempting to pass me. You 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?" You said at the same time, your hand on my arm as you braced yourself.

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

We both started laughing. You removed your hand, and I felt its absence. It looked like you were ready to take off again and continue running, but something was holding you back.

When I picked up on that, I felt a strong and sudden desire to keep you 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, you just laughed and told me not to worry about it.

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

You smiled. "Nah, I'm not really concerned with that."

I smirked and blushed, happy to hear you 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 you.

"I actually don't remember the last time a pretty girl offered to get me a drink," you 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."

You 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 to you.

"This is my friend Molly," I said to you. "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," I said to her.

We all laughed together, you 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 told you, giving you permission to run ahead of us.

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

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

"He was cute!" Molly said once you were 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 you 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 you were, standing amongst the volunteers handing out water, smiling, with two entire bottles in your hands.

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

We jogged up to you, and you told us you talked the volunteers into giving you the full bottles, knowing the flimsy 1/2 filled paper cups wouldn't do the trick for us.

It was enough to win Molly over. "You are a genius!" she exclaimed, thanking you as you 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, you 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.

You shook your head, "No, not long at all."

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

You 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 you 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.

You kept looking at me, your eyes roaming over me and then returning to meet mine. Your gaze was intense, making me wonder what all you were imagining, or picturing. I had to force myself to maintain eye contact, feeling overwhelmed, my pussy suddenly throbbing, wondering if you 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 you again for the water bottles.

Then, as we got ready to continue the race, you said, "I'm gonna hang back another minute or two to see if one of my co-workers will catch up." I noticed your 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 you over my shoulder. Sure enough, I caught you 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.

***

After finishing the race, Molly and I met up with some other friends who came to watch and support us. We all hung around in Grant Park for the post-race festivities, walking around to the different tents and booths set up by vendors and sponsors, getting some more water and snacks.

At some point, Molly noticed me scanning the post-race area, obviously looking for you.

"What?!" I asked when she gave me a knowing look. But I knew I was busted.

"Oh yeah, and Sam met a guy during the race!" Molly excitedly shared with the rest of the group.

"Oh my god, stop!" I groaned.

But she'd caught the others' attention and regaled them with the story. She was teasing me a little, but mostly intending to encourage me to look around for you again and go for it.

I just shook my head, rolling my eyes and telling her to drop it. But she knew me better than that, and I knew any resistance I put up was a waste of breath.

Then I spotted you, walking with your group of coworkers, most of you in matching t-shirts. I kept trying to steal glances, not wanting to get caught staring, by you or my friends.

I noticed you were looking around, too, and I tried not to let myself believe you might be looking for me - not wanting to get my hopes up. I forced myself to look away, but kept you in my peripheral vision. Then, when I thought I felt your eyes on me, I looked back over at you. Our eyes met again, and you were already smiling. I felt myself smiling too, an involuntary reaction, biting my lip in a vain attempt to control it. I knew I was in trouble.

Then my friends started talking about leaving, to go out to a bar for some proper food and drinks. I tried to muster the courage to go up to you and get your number or give you mine, hoping that Molly would see you, too, and give me another push to do it, frustrated with myself for needing that.

You were still watching me as we left, glancing over as you stood around talking with your group. I gave you a little wave. You looked like you were considering trying to catch up with me before I was gone, but then your group was moving on, too, in the opposite direction. So that was that.

***

After lunch and drinks, Molly and I walked home together to our cozy 4th floor apartment in Lincoln Park, just across Clark Street from the Zoo. We were groaning from exhaustion by the time we got to our door.

Molly was still teasing me about you. "I still can't believe you didn't get that guy's number! We should've scoured the park for him before we left!"

I had definitely been feeling regret, too, and hadn't quite stopped thinking about you all afternoon. But I had also wondered about what kept you from coming up to me after the race, when you saw me leaving. As I overanalyzed the situation throughout lunch, I'd eventually concluded that you must not have felt interested enough to chase after me, and so it was probably better that I didn't go back up to you and embarrass myself any further by trying to offer my phone number.

Feeling frustrated, and as the physical and mental tiredness seemed to catch up with me, I ended up snapping at Molly. "Just drop it, okay?"

Molly bristled at my outburst, but knew me well enough not to push any further in the moment. "Okay, sorry."

Then her phone rang as we came inside.

"My mom," she shared. "You can shower first."

I sighed, all the annoyance already gone, just grateful that she was so understanding. "Okay, thanks."

Then Molly went into the kitchen to talk on the phone, while I went into the bathroom to shower.

As I stripped my sweaty clothes off and turned on the water, waiting for it to heat up, I started thinking back over our interactions, trying to persuade myself that it wasn't really anything, or at least that Molly was making it into something more than it was. I shampooed and conditioned my hair, and washed myself with the sudsy loofah while I fought any notion that there was something special about the connection we had.

And yet, as I thought about your smile and the way you looked at me so intensely, I felt my pussy clench. The memory was making me wetter than the shower could.

I allowed myself to picture you standing here in the bathroom with me, looking at me like you did as Molly and I were running up to you at the second water station, with that dangerous smile, saying something flirty and funny. I pictured your body, wanting to peel your sweaty shirt off and run my hands over your chest. I imagined looking down and watching the bulge grow through your shorts as I touched you. Then you'd slide the shorts down, letting me see you, your cock already hard, springing free. I'd watch as you moved closer to join me in the shower, not saying a word.

Getting lost in the fantasy, I leaned back against the shower wall, propping one foot up on the edge of the tub. I reached down and rubbed my entire hand over my pussy, my middle and ring fingers pressing in between my lips, and then slipping inside, pressing in gradually deeper as I slid them in and out. I sighed, feeling the water washing over me. With my other hand, I reached up to squeeze my breasts and roll my thumb over each nipple, feeling them harden.

I imagined you there with me, watching your eyes rake over me as you stroked your cock. Wanting to feel your hands on me, almost as much as your mouth. My index and middle fingers moved to my clit, rolling circles over and around it as I imagined you leaning in close to me. Teasing me. Making me think you were about to kiss me, but then just reaching around me for some soap. Using the loofah to wash me, rubbing it all over. Feeling your fingers "slip" and touch me, too. Rubbing over my nipples. Grazing my ass. Then you'd lean down and gently ease my legs apart to wash between them, fingers brushing over me there. Rubbing. Watching my facial expressions as you touched me.

My pussy clenched at the thought of having your fingers inside of me. I knew I was close after thinking about you all day long, building myself up. I imagined you there fingering me, telling me how much you want me. How you haven't been able to stop thinking about me, either. Telling me about all the different things you want to do to me.

It didn't take long before I was rolling over the edge, writhing and bracing myself on the shower wall to keep from slipping. I rubbed my clit fast and hard through the orgasm, my mouth hanging open in a silent moan.

As I came down, I rested my head back against the shower wall, breathing hard and cursing under my breath. As good as the orgasm was, I knew I wasn't nearly sated. I pictured you pulling your fingers out of me, immediately replacing them with your cock. The image caused my pussy to clench yet again, and I knew I needed to feel something more.

My eyes roved over the shower rack hanging on the nozzle, and then around the edges of the tub, which were also covered with random bottles and tubes, looking for something I could use as an alternative to your cock. My eyes caught on a small shampoo bottle, one of the few we had that wasn't gigantic and didn't have sharp corners and/or an attached pump. It was Molly's, and I knew it was a bitch move, but I didn't even try to resist. I grabbed the bottle and brought it down to my opening, rubbing the cap end along my slit before attempting to push it inside. It was a tight fit, but I was able to get it in about halfway. I started thrusting it in and out, gradually pushing deeper and moving faster while fingers from my other hand worked on my clit.

I was feeling close again when I heard Molly knocking and calling in. "Hey, save some hot water for me, Sam!"

Fuck. My concept of time whenever I was masturbating and/or having sex had always been horrible, and I realized I did not know how long I'd been in the shower, much less what had come over me. Deciding to wrap it up before I did indeed use all the hot water, I washed off and replaced the shampoo bottle, then turned the water off. I climbed out of the shower carefully, my ears ringing, feeling light headed from that orgasm. I wrapped myself in a towel and headed to my room, calling to Molly that the bathroom was all hers.

Closing the bedroom door behind me, I sighed, thinking that I should just push you from my mind and let go of the regret I felt. I tried to convince myself that I was building up our interactions in my mind, that it was really nothing, and rather than leaning into the unhelpful thoughts, I should distract myself from it/you until I just forgot about you altogether.

The trouble was, I knew that wasn't what I wanted to do. So then I swung the other way and tried to rationalize another line of thinking. I probably wouldn't ever see you again. So, I wondered, what was the harm in fantasizing? That thought felt more like what I wanted to hear, so I just went with it, smiling and lying back on my bed, not bothering to close my curtains before continuing to play.

My towel came undone as I lay back, spreading my legs, pressing my breasts together, squeezing them, pinching and playing with my nipples.

I started imagining your mouth on me, your piercing eyes looking up at me as you flicked your tongue at my clit, then rubbing it, building me up again.

I reached down to rub my fingers along my slit, dipping inside and feeling how wet I was. Then I continued rubbing my clit, rolling around in circles, spreading the wetness around my pussy.

I kept picturing you, flashing through all the images again more quickly: the way you looked at me right after you first crashed into me, and again when you were waiting for me to catch up later, then when we saw each other after the race. Imagining you stripping your clothes off in my bathroom and joining me in the shower. Touching me. Cleaning me. Fingering me. Licking me. Dirty talking, telling me you were picturing exactly this when you first saw me this morning. Making me cum again.

And then I was, my whole body bucking up and writhing on the bed as my fingers pressed down on my clit and kept rubbing. My eyes squeezed shut as my face contorted in pleasure, my head rolling to the side and pressing into my pillow.

I came down slowly, breathing heavily as I relaxed into the mattress. My body writhed, legs rubbing together, toes curling, hands running all over myself, squeezing my breasts.

It still wasn't enough. Going again didn't feel like a decision I was making, so much as an impulse. I pulled the towel off the rest of the way and out from under me, discarding it on the floor. Then I reached for the middle drawer of my bedside table and opened it, taking out my vibrator. It was compact and purple, with a rounded hourglass shape. When activated, it pulsated and swiveled around in the middle like an inchworm, with various patterns and levels of vibration. I held down the small power button to turn it on and clicked ahead to my favorite setting, which swiveled in a random pattern of circles and staccato movements and seemed to best simulate the feeling of a tongue on my clit.

I rubbed it along my slit and slipped it into my pussy first, getting it wet with my juices. Then I held it against my clit and closed my eyes, head arching back as I continued to imagine you going down on me. Feeling close again already, I pressed the vibrator down onto my clit harder, rubbing it around, and I swung my legs up and back, reaching down with my free hand to plunge two fingers into myself hard and fast until I was coming again. My hips jerked and writhed, and my shoulders tensed as I rode out the waves of pleasure a third time.

My face felt on fire as I relaxed my limbs once again, leaving the vibrator in place, squeezed between my legs and against my clit.

"Fuck..." I muttered, the pleasure feeling like too much and not enough all at the same time.

Then I reached for my phone, where I'd set it down earlier on my nightstand. I swiped it open, then clicked on the app icon for my Chrome browser and navigated to my favorite porn site. I started browsing, following my usual pattern of scrolling through the recently posted videos, until I would find one that piqued my attention. This time, I scanned for a video featuring a guy that might at least somewhat resemble you, hoping to find some new fun things to imagine us doing together while I continued to masturbate...