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 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...

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 “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 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. “...

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 “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...

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...

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 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...

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 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) 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?...

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...

“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...