My friend Molly and I were running down Wacker Drive, nearing the two-mile marker of the Shamrock Shuffle, an annual 8k race through downtown Chicago. We’d been running together every March since we were sixteen, now seniors in college and roommates. “Let’s grab some water,” Molly panted as we approached an aid station. “Okay,” I agreed, following her lead to veer towards the left side of the street where the volunteers h...

Wrigleyville was crowded for a non-game night. The sidewalks were packed as Molly and I approached the bar, just south of Wrigley Field on Clark Street. We loved coming to Sluggers on Saturday nights for $1 Jell-O shots and the dueling pianos show, followed by dancing in the downstairs bar area, or hanging around at the batting cages. Somehow, we’d arrived early for once, so we got some drinks downstairs while we waited f...

The next several days after Sluggers were a whirlwind of sexting and phone sex. Mark and I were getting pretty swept up in the thrill of whatever was happening between us. Or at least I was. But it felt like he was right there with me. We started talking every night. Mark stayed up chatting with me after his wife went to bed. I would talk to him on my way home from night class or work, or I’d let him distract me from read...

“Soon” finally came that Saturday afternoon. The morning after that fun chat on my way home from campus, Mark told me to send him my schedule and Molly’s so that he could find a time that worked for him. We were both desperate at that point. Mark: Let’s do Saturday Mark: I’m going to tell my wife I need to go to work for a while Sam: Will she believe that you have work on a Saturday? Mark: Yes Mark: It’s happened before M...

There she is again. Right on time, just like clockwork. Tonight she’s already dressed for bed, wearing a black tank top and some pink shorts. Lying on her bed, talking on the phone. It has to be the same guy she’s been talking to every night. Or a girl, I guess. Maybe a boyfriend or girlfriend. They always call at the same time. I wonder if it’s a long distance thing, since she hasn’t had them over yet, as far as I’ve see...

After that first time (or times, plural) with Mark, I somehow felt even more insatiable. We continued with sexting and phone sex mostly, out of necessity. But then, Mark started coming by my apartment on his way to and/or from work on days when I was home and had the place to myself, telling his wife he had to go in early or stay late. Sometimes I would end up running late to class or scrambling to switch a shift at work...

It was a warm Spring afternoon, and I’d just gotten out of the shower following a run along Chicago’s Lakeshore. I was fortunate to live practically across the street from the Lincoln Park Zoo and Lake Michigan, in a cozy two-bedroom apartment with my best friend Molly. She was going to be busy all afternoon and evening with classes and a shift at the bar on the corner where she worked as a server/bartender, so I was wait...

“He’s watching again now, isn’t he?” Mark asked. It had been a few days since The Show, and Chris had been at his window watching me touch myself as I chatted with Mark every night since. The only time I didn’t see him was when Mark was over. That time, Chris seemed to keep himself hidden behind his blinds; though I suspected he was still peeking through and watching. “Yes,” I said, sitting on my bed and looking out the o...

As soon as my meeting ended, I went straight back to my office to check my phone for a message from Sam. I’d hardly been able to concentrate as I sat in the conference room, just knowing that her neighbor was there with her, thinking about what they might be doing. Almost an hour had passed since I told her to invite him upstairs and have fun, and she still hadn’t texted back to say they were done. As I debated about whet...

(Sam) It was a Saturday afternoon, and I had nothing to do. Molly was working, and the few other friends I checked in with already had plans, too. It was a rare, beautiful day in Chicago, so I went out to wander around. Heading north on Clark Street, I was just sort of walking aimlessly, stopping in some shops here and there. Of course, I couldn’t resist texting Mark to see what he was up to. Sam: Having fun family time?...

Sam Later that week, one of my classes got canceled, and I ended up with an afternoon free. I knew Mark was working, but texted him anyway as I walked home from campus in case he had a light meeting schedule and might have time to chat a little. Sam: My afternoon class got canceled :) Mark: Nice Mark: What are you going to do with all your free time? Sam: I guess I should probably study… Sam: But all I can seem to think a...

Sam About a week earlier, I was at home watching TV with my roommate Molly as the app-controlled vibrator Mark bought for me (Eggy, as we called it, affectionately) vibrated gently inside my pussy. I was working on checking off another item from Mark’s sexy scavenger hunt, which outlined several places and situations to wear the toy and try to make myself cum. 1. In class 2. On the train 3. Walking home from campus 4. Out...

Sam The next morning, I woke to noisy construction sounds flowing into my open window from across the street, where a new condo building was going up. I groaned and rolled over, pulling a pillow over my head to block the sound. But then my brain put together that construction sounds meant it must be after 7:00 already, and my first class started at 7:30. I pulled the pillow back away and checked the time on my phone. 7:38...

Mark I was still feeling bad about having to cut my chat with Sam short last night, so when my last meeting of the day got canceled, I figured I’d surprise her with an impromptu visit on my way home. Heather was already expecting me to be home late, so I didn’t even have to worry about making up an excuse. I checked my phone and saw that I had a few messages from Sam. Sam: I can’t wait to talk later Sam: I have a fun stor...

Sam I had the biggest smile on my face all day, knowing that Mark was coming to spend the night. An entire night. Part of it was a relief that he even wanted to come spend the night with me after catching me having sex with my neighbor Chris a couple days ago. I tried to prepare myself for the possibility that he could end up leaving early, not wanting to be around me after hearing everything I had to tell him. But I hope...

Sam “What about the guy over there in the Bears hoodie?” It was Friday night, and I was out at a bar with Mark, discussing his latest assignment for me: I was to flirt with another guy while wearing the remote control vibrator he’d gotten for me, while he controlled it through an app from across the room. I smiled and waited for a beat before turning around to check out the guy Mark picked out, trying not to be too obviou...

Mark My phone buzzed and chimed on my desk as I drafted an email to a client. Glancing over, I saw the text was from Sam and smiled, allowing myself to get distracted from work. I picked up the phone to see what she said. Sam: Just getting out of class :) Sam: What time do you think you’ll be able to come over? I checked the time and then typed out a response. Mark: I just have a few things to finish up, give me twenty mi...

Sam I was already several tequila shots in and stumbling slightly by the time my friend Jenna and I made it out Friday night. We went straight to the bar for more drinks, talking and laughing together as we looked around to check out the guys nearby. I’d always been a loud and horny drunk, which I got a lot of shit for from many of my friends. But my obnoxiousness was nothing compared to Jenna’s, and I loved her for it. “...

Sam “Fuck, I want you so much,” Adam, my Saturday night guy, groaned into my ear as he slid his fingers into me in the back seat of the Uber. We were on our way to my apartment from the bar where we’d just met. “I can’t wait to feel your wet cunt wrapped around my cock.” I moaned and pulled him into another deep kiss, spreading my legs open further and grinding on his hand as my pussy throbbed and clenched. It turned me o...

Sam Before I even opened my eyes, I felt Chris spooning me, grinding his hard cock into me as he groped my breasts and kissed my neck. My body was already responding to him, tingling and writhing before my brain caught up and I realized what was happening. I hadn’t meant to fall asleep or let Chris stay the night. But my initial panicked thoughts vanished pretty quickly as I felt his cock pushing through my swollen lips f...

Sam After my slutty weekend, my thoughts kept returning to Friday night, my first group sex and bisexual experience with my friend Jenna. I realized I was curious to try more things with her and daydreamed about it that week during class. I turned myself on, imagining what else could happen, and what else I might want to try. So, I decided to talk to Jenna about it. We both worked as lifeguards and swim instructors at the...

Mark Before I met Sam, I thought my cheating days were behind me. Although I still look back on my first affair with my coworker Monica as one of the most fun parts of my life, it was also stressful. The lying and sneaking around became harder and harder to keep up with until I couldn’t. Inevitably, my wife Heather discovered our texts, including some racy pictures, which I’d forgotten to delete. I wasn’t sure we’d be abl...

Sam It was really rainy when Mark and I landed in Boston. A good excuse to spend our first night at the hotel, enjoying some alone time together in the room. We fucked over and over, and lay around eating room service and talking while we recuperated. It felt so exciting having Mark all to myself for a little while. I smiled when I noticed how nice it was that he didn’t have to keep checking his phone to see how much time...

Sam I shivered in my seat at the trendy Boston restaurant where Mark and I were eating. It could’ve been the cool breeze flowing through the outdoor dining area, chilling the June evening air. Or it could’ve been the egg-shaped vibrator in my pussy that Mark was controlling with the app on his phone. “Cold?” he asked with a smirk. “I’m not sure,” I chuckled, struggling not to moan as he increased the intensity of the vibr...

Sam I woke up alone in the hotel bed and checked the clock on the bedside table. 9:43 AM. Mark must’ve let me sleep in after another late night of orgasms, rather than waking me as he was leaving for work. I moaned contentedly and luxuriated in the cozy bed, stretching my limbs and enjoying the soft, cool sheets on my bare skin. As I reached onto Mark’s side of the bed, my hand brushed over something. I found a postcard-s...

Sam On our last night in Boston, Mark and I decided we couldn’t end our trip without checking out the hotel’s outdoor hot tub. It was a perfect, chilly, late spring night, and the only thing keeping me from feeling fully content was the knowledge that our bubble of bliss was about to pop. Normal life and Mark’s family would be waiting when we returned to Chicago. “I hate that this week is already over,” Mark said, as if r...

Mark It was a Saturday night, and my wife Heather and I were attending a fundraiser at the rec center where my girlfriend Sam worked and taught swim lessons for my kids. I knew it was reckless, but the thrill of sneaking around with Sam was irresistible. And beyond that, she made me feel so desired, which I rarely felt at home. As soon as Heather and I stepped inside, I looked around for Sam. I quickly spotted her at the...

Molly “Ohh, that feels good,” I moaned as Josh teased me with his tongue. His warm breath tickled my inner thighs and caused my pussy to clench and my legs to clamp around his head. He tugged me closer to him by my hips and moaned into me, pressing his tongue in between my lips. My body writhed in response; my back arched, and my toes curled. I was getting so lost in the feeling of Josh’s mouth on me that I didn’t hear th...

Mark I rearranged my schedule to take a long lunch at the end of the week, planning on swinging by my girlfriend Sam’s place for a quickie. I’d been busy at work on top of needing to be extra cautious at home with my wife, Heather, so it had been a while since I had time to see Sam. She’d been understanding about all of it, but I could tell she was getting frustrated with me. I had a feeling she was holding back from shar...

12 Years Later Mark I spotted her from the stands at the swim meet, wearing shorts and a polo shirt with the Alto Swim Club logo, her long, dirty-blonde hair tied up in a ponytail. She had a stopwatch around her neck and held a clipboard to her chest. My heart pounded as I watched her talking and laughing with the other coaches. According to the heat sheet, her team had two swimmers in the finals for the thirteen-to-forte...