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 about is having your cock in my mouth ;) 

Mark: Mmmm

Mark: I’m about to start a meeting now, then just administrative type stuff for the rest of the day

Mark: I think you should come meet me at my office

Mark: I have something for you

My stomach fluttered with excitement when I saw Mark’s replies. I didn’t know if he meant he’d gotten me a gift or what, but really, I didn’t care. I just felt excited that he invited me to come meet him at his office despite the riskiness, and that there was something that made him think of me. 

Sam: Okay :) 

Mark: Oh, and wear a skirt :-*

I chuckled, a big smile on my face as I looked up from my phone to cross the street, almost back at my apartment. Once I was across, I texted back. 

Sam: haha, okay

Sam: Any other requests? ;)

Mark: I’d tell you to make sure you’re wet when you arrive, but I don’t think I even need to ask, do I? 

Sam: No, you definitely don’t need to ask :P 

Mark: mmm

Mark: Can’t wait to feel that

Mark: Meeting is starting now, should just be half an hour

Sam: Okay, I’m just going to go up and change, then I’ll be on my way :) 

Mark: Sounds good 

Mark: Text me when you’re here

Sam: Okay

Sam: See you soon :) 

Sam: Have a good meeting

Mark: Thanks :-*

Mark: See you soon, my slut

My cheeks were already hurting from smiling so much as I clicked off my phone to let myself into the building. As I climbed the stairs, I planned out what I would change into, getting excited about what Mark might have planned. 

As soon as I got into the apartment, I kicked off my sandals, dropped my backpack right inside the door, and went into my room. My roommate Molly was still out, so I took off my clothes without bothering to shut the door, tossing my shirt and shorts into the laundry in my closet. Then I looked down and stripped off my underwear and bra too, wanting to put something special on for Mark. 

I didn’t register that my curtains were wide open until I was already naked. As a habit, I normally didn’t think twice about changing in front of an open window. But now that I had a voyeuristic neighbor and a dominant married guy who wasn’t always okay with him watching, I had to be more careful. I looked over to Chris’ window as I shut the curtains… no sign of him, anyway. 

Ten minutes later, I was ready to go, wearing red lace cheeky underwear and a matching bra under a cute black, white, and red dress with a heart pattern, short sleeves with ties, buttons all the way up the front, and a belt tie. The dress came to my mid-thigh, so I knew it would provide easy enough access for whatever Mark had in mind, without being so slutty that I’d draw too much attention at his office. 

Mark had texted me the address to his office, so I looked up the route on the CTA site, already heading out and guessing that the #22 Clark bus would be the best option. I’d probably arrive within a few minutes of his meeting ending. 

As I walked and waited at the bus stop, I texted Mark to give him an update. 

Sam: On my way now :) 

Sam: Just waiting for the bus

Sam: Should be there in about 20 minutes 

Before putting my phone away, I scrolled back a bit to reread our recent text exchange. I smiled again when I saw Mark’s message about having something for me, wondering again what it would be. Knowing Mark, it would likely be something with a sexual theme. Did it have anything to do with him telling me to wear a skirt? Or was that just him not wanting clothes in the way, so he could easily fuck me in his office? I knew there was no use guessing, so I tried to practice patience, putting my phone away to look around and people-watch instead while I waited for the bus. 

***

I remembered Mark saying that his office was right next to the Willis Tower, so I knew about where I should get off. I texted again as I made my way to the address he gave me on Wacker Drive. 

Sam: Almost at your building now :) 

He got back to me right away.

Mark: Okay, I’ll come down to meet you :) 

I waited just outside the main doors, looking around as a mix of tourists and people in business attire passed by. It was nearing 5:00, so there were a good number of people on their way out of Mark’s building, leaving work for the day. I smiled to myself, getting excited about what we might get away with in a nearly empty office. 

“Hey there, sexy,” Mark called over the city noises as he approached me. 

“Hi,” I smiled back. I wasn’t sure how to greet him there, in public. Any of the people walking by could be his coworkers and might know his wife, or at least what she looked like. So, I waited to follow his lead. 

Mark wrapped his arms around me in a hug when he was close enough, kissing the side of my cheek. Then he spoke into my ear, “Cute dress. I can’t wait to see what you’re wearing under it.” 

I shivered a little, feeling his warm breath on my neck and reacting to his words. 

He gave my ass a quick squeeze and winked as he pulled back, leading me inside. 

I bit down on my bottom lip to keep from smiling too much as Mark held the door for me and directed me to the right elevator bay for his floor. I was feeling jittery with excitement as we waited for several people to get off of an elevator on their way out before we could get in. Since it was nearly the end of the day, we were the only ones going up. 

Mark hit the button for the 29th floor, then backed me up against the side of the elevator. I gasped and moaned as he pressed himself against me, kissing me deeply right away. His hands slid over my hips and down to grab my ass through my dress before pulling it up, revealing lace and bare skin. 

“I want to fuck you right here in the elevator,” Mark groaned, pulling on the back of my left thigh until I wrapped my leg around him. As his lips slid down my neck, he brought his right hand around to my front, fingers rubbing and pressing into my slit through my underwear. 

“I want you to,” I moaned, grinding on his hand and reaching for the front of his pants. 

He took my encouragement, pulling my panties to the side and slipping his fingers into me, feeling how wet I was for him. 

Just as I was working on opening his pants, we heard the elevator ding, letting us know we were approaching his floor. Mark pulled back just slightly, and we smiled together, enjoying the closeness until the elevator came to a complete stop and the doors opened. Then I quickly readjusted my panties and smoothed my skirt down as we stepped out onto his floor. 

We passed a few others as I followed Mark through the common areas of his company’s office. He said a quick, “Hi,” or “Goodnight” to most of them in passing. I met eyes with a woman walking down a nearby aisle between some employee cubicles, and she seemed to look me over, eyeing me and Mark together and assessing our situation. I could feel my cheeks heating as I blushed, and watched her smirk at me before continuing on her way. After that, I opted to avoid eye contact with any others. 

Mark walked quickly, leading us straight to his private office. It was a decent size, with an exterior window and view of the Willis Tower, as well as an interior window leading out to the rest of the space, which was mainly filled with cubicles. Luckily, Mark already had the blinds closed, so we didn’t have to close them suspiciously now. 

As soon as he’d locked the door, Mark reached for me and pulled me closer, one hand on my hip and the other behind my neck. He kissed me deeply, and I moaned, wrapping my arms around him, too. 

We made our way around the desk. Mark led me, tugging on me as we kept kissing before his lips started trailing down my neck as his hands worked on the front buttons of my dress. He moved a few things out of the way on the desk, then his hands slid around my back and down to my ass, squeezing and lifting me until I was sitting up, right in front of his chair.

I felt my heart pounding in my chest as Mark pushed my knees apart and ran his hands up my thighs, pushing my dress up to my hips. Then he slid a hand between my legs to rub my pussy through my underwear again, pressing his fingers into my slit. 

“Fuck,” I gasped, freezing and clenching for a moment before reaching for him, too. 

My hand went straight for the bulge in his pants before slipping up higher to undo his belt. I fought his pants open as quickly as I could and reached inside to wrap my hand around his hardness, earning a groan right into my ear as he sucked and nibbled on my neck and earlobe. 

Before I could get much further, Mark pulled back, sitting down in the desk chair. He pressed back on my thighs, keeping my legs spread wide and looking me over as I sat up on his desk before him with my dress hiked up. I followed his gaze to the wet spot that had quickly formed on my underwear. He rubbed it with his thumb, slowly at first, but getting faster quickly, pressing harder. I sighed and moaned, my head rolling back momentarily, and then back up, our eyes locking. 

“I’ve been hard for you sitting here at this desk so many times, Sam. Every time you text me while I’m working, my cock stiffens and twitches for you.” 

“Ohh god,” I moaned, getting close. I was already losing the ability to form complete phrases or even thoughts, only focused on cumming with Mark; cumming for him. 

“I’m going to make you cum just like this, so I’ll always be able to picture you here, sitting up on my desk with your legs spread, cumming for me.”

“Yess, so close,” I breathed, my eyes still trained on him, only looking away to glance down at the way his fingers were moving over my clit, rubbing through my underwear. I tensed up, my toes curling, pussy clenching, hands forming into fists as my face furrowed in pleasure, bracing for the impending release. 

“So wet already. You are always so wet for me; I love it. I want you to cum. I want to make your underwear soaked for me.” 

“Fuck!” I groaned, my hips grinding, pressing up to feel more of his fingers. 

“That’s it, cum for me, Sam. Cum hard, right here on my desk.”

I felt it building. Soft, staccato moans flowed from my mouth involuntarily as my pussy clenched, my hips raising in quick thrusts. 

“Cum!” Mark ordered. “Cum now!”

And then I was. I yelled out, cursing and moaning as I rolled over the edge, fighting to maintain eye contact with Mark as my body writhed on his desk. 

“That’s it, good girl,” he moaned, smiling as his fingers pressed into me, rubbing fast through my orgasm. 

Even as I came down, he continued pressing his fingers in, rubbing between my slit and pressing up into my opening, getting my underwear as wet as possible. 

I smiled too, sighing as I recovered, still breathing hard. “Is this the image you were hoping for?” 

“Definitely,” Mark concurred. 

Then he reached to open one of the side desk drawers and pulled out a small gift bag, setting it on the desk beside me. 

I couldn’t help the big grin that spread across my face. “For me?” I asked. 

“It is,” Mark nodded. 

I sat back up on the desk, my skirt still hiked up, and legs still spread around Mark as he sat between them. I picked up the bag and reached inside through the tissue paper, pulling out a smooth box that was not fairly small, but heavy. It was pink and purple and displayed a picture of what appeared to be a pink sex toy, shaped roughly like an egg with a longer tail. 

I smirked up at Mark. “I had a feeling it was going to be something in this genre.” 

He laughed. “Yeah… I guess I’m pretty predictable, huh?” 

I laughed too and shrugged. “You know I like it. What does this one do?” 

“Well…” Mark started, taking the box from me and pulling off the lid, taking the toy out of its packaging. It looked like he’d already opened it to set it up and get it ready to go. “You slip it inside, and you can wear it around. You can either control it with the button that’s at the tip of the little tail part that sticks out, or there’s an app that works as a remote control.”

“Oh?” I asked, getting intrigued. 

“Yep. And you can allow a partner to control, too. From a distance,” he added with a wink. 

My smile grew even wider. “Interesting.” 

“I thought so,” he smiled back. He held the toy and looked up at me expectantly. “Want to give it a spin? I already charged it up, so it should be ready for action.” 

I laughed. “How thoughtful of you.”

“I try,” he smiled. 

Mark’s free hand cupped my cheek before sliding down to my neck and squeezing gently, then trailing down my chest through the open buttons of my dress, squeezing my boobs through my lacy bra and moving down further still. He pushed my thighs back up and pulled my underwear to the side before rubbing the toy along my wet slit. 

Then he pressed the button at the end of the toy’s tail and it buzzed to life, vibrating against my lips. 

I gasped and bit my lip, watching as he continued to rub it on me for a few more strokes before pressing it inside. I was wet enough by that point that it slipped in easily. He teased me with it a little more, smiling up at me as he slipped it in and out. Then he pressed the egg in deeper, his fingers following as he pushed it up as far as he could inside of me, leaving just a couple of inches of tail sticking out. 

I gasped as I felt it pressing so deep into me, my thighs clamping shut around his arm reflexively. 

“I want you to wear it now, while I show you around the office and control the settings on my phone,” Mark commanded.

“Mmm,” I moaned. “You already downloaded the app to test it out?” 

“I already had the app,” he explained, scrolling on his phone to find and open it. “Heather has a similar toy that we hardly use. So I figured this would be pretty safe, since she won’t question why I have the app at least. Might just need to keep deleting yours from my profile while we’re not using it, just in case.”

“Oh, okay,” I agreed, smiling and looking over the top of his phone as he maneuvered through the app. “That works.” 

Then Mark started adjusting the vibrations using the remote function, changing the style and pattern of the vibes, as well as the intensity. He smirked and watched my reactions to each one, asking me what I thought.

“I like that one,” I moaned, when he’d stopped on one that felt like a heartbeat pulsing. 

“Yeah?” he asked, turning up the intensity of the vibrations.

“Fuck!” I yelped in response, my toes curling again. “Yeah, that’s good. And the one that’s like a wave.”

“Good to know,” Mark winked. 

“What does the ‘touch’ function do?” I asked, looking over his phone at the app screen. 

“I’m not sure… I was curious to try that out, actually. Heather’s toy doesn’t have that.” 

Mark clicked on the icon I’d asked about, and a blank box came up. He touched within the box and started moving his finger around, and I felt the vibrations swivel with his touch. 

“Ohhh, that’s good,” I moaned, smiling. “It’s like you’re touching me.” 

“You like that one?” he asked. 

“Yeah… that’ll be fun when we’re not together. I can imagine your fingers inside me.” 

“Yeah, I like that, too.” 

We experimented with it a bit more before deciding to get on with the tour. I re-buttoned the top of my dress and adjusted my underwear around the tail of the toy before smoothing my skirt back down. 

Mark continued teasing me with the toy as we left his office, changing up the vibrations here and there as we walked, and he showed me around. A few employees were still working in their individual offices and cubicles, but most people seemed to be gone for the night. I was mostly glad about that, feeling self-conscious, and wondering whether the vibrations would be audible. But I realized that there was also a part of me that was sort of wanting more of an audience. 

I got a taste of the riskiness I desired when Mark led me into a conference room, where the after-hours cleaning crew was already getting to work. Mark led me over to the windows while they worked, pretending to be showing me the view. One woman was vacuuming, so at least there was a noise buffer to cover up the sounds of the vibrator, and Mark’s words. 

“This is where we always have our meetings. I spend a lot of time sitting at this conference table. It would be nice to make some memories in here, so I can entertain myself with those thoughts whenever I get bored during meetings from now on.”

I smirked at him. “Might be disrespectful to make a mess right after the cleaners finish…”

“Maybe we should start now, then. They can clean up around us,” Mark teased, turning up the vibrations yet again. 

I flinched again when I felt it. He was making it hard for me not to react or moan. I felt my nipples tingling and getting hard, and couldn’t decide whether I hoped they were visible through my dress and thin, lacy bra or not. 

Mark leaned in closer behind me as we continued facing out the window, leaning in to speak into my ear. “I’m going to sit you up on the conference table as soon as they finish, in the spot where I usually sit. Then I’m going to go down on you until you cum all over that freshly cleaned table with the toy still going inside you. So any mess we make will still be there for tomorrow’s meetings.”

I watched as he used the app to turn the vibrations up again, as high and as loud as they would go, and felt my pussy clench in reaction. 

“Fuck!” I muttered, reaching back and gripping Mark’s thigh. 

Then, the vacuum turned off just as he said, “I can’t wait to feel you cumming on my face,” in a voice much louder than a whisper. 

“Shit,” Mark cursed. 

We both started cracking up, glancing at the cleaners, who all graciously continued their jobs with little more than some amused smiles. In fact, they seemed to move a little more quickly, trying to finish up and get out of our way, apparently. 

They left the room soon after without a word, and Mark kissed me again, guiding me back to the table right away. 

“Right here,” Mark directed, helping me up onto the table in what was apparently his unofficial spot. He kissed his way down my neck, once again working on the buttons of my dress, pushing it open and off of my shoulders. It felt so naughty, knowing that anyone who might still be around working, including the cleaning crew, could easily walk in and catch us. I was a little surprised that Mark wasn’t more concerned about that, but I figured if he wasn’t too bothered, then I shouldn’t be, either. 

He pressed himself between my legs and pushed down on the backs of my thighs until I was leaning back on my elbows, my dress sliding up once again. This time, Mark hooked his fingers in the waistbands of my underwear and tugged them down and off quickly, tossing them aside and leaving me exposed. 

He slid down into a chair, still holding my legs back, his eyes trained on my pussy as the toy continued to vibrate within me. 

“See the wetness glistening on your lips?” he asked, smiling up at me. 

I smiled back at him and leaned up to look. 

Mark continued to tease me by tugging on the tail of the vibrator, pulling it out and pushing it back in a bit more. Then, as promised, he leaned in closer slowly. His eyes met mine and held my gaze as his tongue and then his lips met my pussy, first teasing my lips, brushing over me lightly. Then his mouth hovered over my clit before his lips circled around it and held there, his tongue alternating between rolling over it in circles and then flicking up and down, back and forth quickly. 

“Ohhh god,” I moaned, my hands coming to the back of his head, fingers combing into his hair. “That feels so good. I love feeling your mouth on me.” 

He pulled back and looked at his phone once more, setting the toy to the highest vibration on the wave setting that I’d told him I liked. Then he set the phone down at the table beside us and got back to work, licking and sucking on my clit while the toy stimulated me from within. 

“Fuck!” I yelled out, leaning up to watch him, maintaining eye contact so he could see the pleasure washing over my face. 

My hips started grinding of their own volition until I was practically rubbing my pussy on his face. I felt myself quickly building up to an intense orgasm and decided not to hold back, despite the semi-public setting. My moans got louder in between muttered curses and encouragement. 

“Don’t stop! Fuck, that feels so good! I love how hard you always make me cum. You’re going to make me cum so hard on your face… I’m so close. It’s so hot being here in your office… and feeling you control the toy. I can’t wait for you to make me cum with it all the time while we’re on the phone.”

I felt and heard Mark moaning into my pussy as I went on. Then I leaned up again to watch him and noticed that he was stroking his hard cock as he licked and sucked on my clit. There was something about seeing him getting so turned on as he was pleasing me that just drove me crazy. I started breathing harder and felt myself clenching suddenly, knowing I was close. 

“Fuck, I’m gonna cum!” 

And then I was. It came on more suddenly and stronger than usual, my body writhing out of control on the table. I felt my thighs shaking and clamping closed around Mark’s head, trapping him there as my hand held his mouth down on my clit. I was yelling out so loudly that anyone on the entire floor likely heard me, despite the sound of the vacuum being audible, as it was still running in another part of the office. 

It took some time for me to come down and relax from that intense orgasm, especially with the toy continuing to buzz inside me. But then, as I finally released my grip on his head, Mark stood up over me, smiling and wiping his face. He opened his belt and pants quickly, pulling his cock out and rubbing the head along my pussy, getting it wet on my lips and pressing into my opening a bit to feel the vibrations on his cock.  

I moaned and smiled up at him. “I want to feel you inside me now. I need to feel you fucking me.” 

“I’m going to,” he assured me, continuing to rub and slap his cock on my pussy. “I’m going to cum fast inside you. Do you feel how hard I am for you?”

“Yesss,” I breathed. “I can’t wait to feel your hard cock inside me, filling my pussy. I’m so wet for you right now… I always want you so much.”

“I always want you, too. It’s so hot having you here, making you cum in my office. Seeing the wetness on your lips and the tail of the toy sticking out, and hearing your reactions as I controlled it.” 

“Yeah, it’s really fun,” I grinned. 

Then Mark reached down and pulled on the tail of the toy until it popped out of me. As it released, I could feel a gush of fluid that followed. 

“Fuck!” Mark cursed. 

I leaned up on my elbows again, looking down to see a puddle on the table beneath me. My surprise must’ve shown on my face. I felt myself smiling involuntarily, somewhere between embarrassed and excited. 

“That’s never happened before,” I told Mark, laughing a little, nervously. 

He just grinned back at me, shaking his head. “So hot.” He leaned over me, holding me behind my neck and pulling me in until our lips crashed together, kissing me hard. 

I moaned and sucked on his tongue and bottom lip to encourage him and keep him from pulling away. 

Mark moaned into my mouth, sliding the head of his cock between my wet lips before finally pressing into my opening, groaning as he filled me. 

“There’s going to be a lot more where that came from,” he added as he pulled back from the kiss to thrust into me, hard and deep right away. 

I gasped and sighed as he held the toy on my clit and continued pumping into me. The wet sound of his cock sliding in and out of me was audible in the room.

“God, that’s so hot!” Mark groaned. “I love hearing how wet and sloppy you are.”

I smiled and moaned, my back arching again as he pressed himself into me, hard and deep. “You always make me so wet.”

“I’m going to cum so hard inside you.” 

“Ohh god,” I moaned. “I want you to. Please give me your cum.” 

Mark groaned, pounding into me as he held my hips. “I want you to cum again first. I want to feel you gushing and cumming all over me before I fill you up.” 

My head rolled back as I moaned and clenched around him. 

He kept thrusting, slowing just a little as he rubbed the toy in circles over my clit. “That’s it, Sam. Cum on my cock.”

“Fuck!” I yelled, feeling him pick up the pace of his thrusts again.

“Who’s slut are you?” 

“Yours! Ohhh god!”

“Show me! Cum on my fucking dick. Make that wet fucking pussy cum all over me! Now!”

“Ohhh my god! I get so fucking wet all the time thinking about you, and how much I want your cock. All the time!” 

He grunted, slowing his thrusts slightly as he seemed to get closer, too. “You’re such a good slut for me. My sexy college slut.” 

His words did the trick yet again. I held his hand with the toy down against my clit, grinding my hips and writhing, thrusting up onto him as I came again, clenching on his cock and yelling out again, practically screaming and not caring who heard me. 

“That’s it, Sam. Good girl. Cum on my cock. Cum hard,” Mark said, holding my hips to keep his cock buried deep inside me. 

I was breathing hard and moaning contentedly as I came down again, toes curling and continuing to squeeze around him. “Cum inside me now. Please?” I begged, smiling up at him. 

He smiled back. “I’m going to. I’m going to send you home with a big fucking load of cum in that slutty pussy. So hot hearing you beg for my cum.” 

I moaned, listening to Mark’s hot words and feeling his hands slide up my chest. He tugged the lace of my bra down roughly, grabbing and squeezing my tits before reaching up higher. One hand clamped around my neck while the other held onto my shoulder as he braced himself to keep pumping in and out of me furiously. I yelled out again, feeling his deep, hard thrusts. And then he was moaning and grunting over me, cumming deep inside. 

I smiled and moaned, running my fingers up and down Mark’s sides and back, luxuriating in the feeling of him holding me and filling me. He was breathing hard, too, and still moaning as his eyes gradually fluttered open and his body relaxed. He leaned over me and waited for me to meet him halfway for another kiss before slowly pulling back and out of me. 

I started to get up too, but Mark stopped me. 

“Wait a sec,” he said, holding me down gently with a hand on my chest. 

He picked up the toy again. It had stopped vibrating at some point. I guessed that the battery must’ve finally died. Still, Mark smiled as he pushed my legs open and pressed it into me yet again. 

“I want it to hold my cum inside you as long as possible. I like thinking about you having it inside you all night as you go home and have dinner with Molly, watching TV or doing your homework. So you’ll keep thinking about me every time you feel it.” 

I smiled back up at him, staying put on the table with his cum and the toy, his gift, inside of me as requested while he retrieved my underwear and slipped them back on over my legs. 

Then, we both readjusted our clothes and helped each other to check and make sure we were presentable enough before leaving the conference room. It felt like a futile effort, since the cleaning crew clearly knew what we were up to. But we both had to look presentable enough to make it home, anyway. 

Mark had finished working for the day, so he was ready to head out with me. But as we passed by his office, he squeezed my hand to hold me back for a moment. 

“Oh, hang on a sec, I almost forgot something.” 

I followed him in, watching and waiting as he went back around his desk, retrieving the gift bag and box from the toy. He reached into the bag and pulled out a small piece of paper that appeared to be some sort of list. He smiled as he held it out to me across the desk. 

I smiled back, tilting my head to the side quizzically as I stepped closer to take the paper from him. “What’s this?” 

“It’s another part of the gift. And maybe some more homework for you.” 

I laughed a little, inspecting the list:

In class

On the train

Walking home from campus

Out shopping / at the grocery store

Watching TV with Molly

At work lifeguarding

During swim lessons

Out at a bar, while you’re flirting with someone

In a cab / Uber

“It’s a sort of to-do list, I guess. Or maybe a scavenger hunt is a more fun way to think of it. I want you to wear the toy to each of these places and try to cum while you’re there. And I want you to let me know when you’re getting ready to cross an item off the list so I can log onto the app and control it if I’m available.” 

My smile grew and grew as my eyes scanned down the list and I heard Mark’s explanation. I felt the excitement growing fluttering in my stomach. “I see you’ve been thinking about this quite a bit.” 

“Maybe a bit,” he replied with a wink. 

I laughed again, reading over the list again, picturing what it would be like to have the toy buzzing inside of me in each of those places. 

My attention caught on number seven: During swim lessons. My first thought was of how exciting it would be to wear it with Mark and his wife and kids right there in the pool, too. Not to mention the other swim instructors and all the other families. He obviously wouldn’t be able to control it in that scenario, but it would be exciting to have that little secret just between us with so many others around. I wondered whether the vibrations would be noticeable underwater, or whether it would cause bubbles or something… It made me nervous but so excited at the same time. 

“What are you thinking?” Mark asked, sensing me getting lost in thought. 

I shared my reactions with him, and he grinned in response. “Yeah, it’ll definitely be daring. And exciting.” 

“Yeah,” I agreed, blushing. Then I asked, “Is this list complete? Or still in progress?” 

“Why, do you have some places you’d want to add?” he asked, smirking back. 

I shrugged, playfully. “Maybe.”

“I’m sure we’ll both come up with some more ideas as you go.” 

“Probably,” I nodded.

“Better get to work,” he teased, coming back around the desk and leading me back out of the office, towards the elevator.

I laughed. 

“Which one do you think you’ll go for first?” 

“Hmm…” I pondered, looking back over the list again. “Well I guess I have to take it home and charge it first tonight… but maybe I could try in class tomorrow.” 

“I think that’s a good plan.” 

“I’ll probably try to go in order, unless other opportunities pop up sooner.” 

“Sounds good,” Mark concurred, pressing the elevator call button as we entered the bay. 

“And I think I want to wait until you’re free to help control it for at least part of the time… I like the idea of it being something we’re doing together,” I suggested. I wasn’t sure if that’s what Mark had intended, but it felt more fun to me that way.  

“Yeah, I want that, too,” he agreed, reassuring me. 

“Okay, good,” I smiled as we heard a ding, an elevator approaching to take us down to the lobby. 

We stepped inside, both smiling at the memory of our ride up to his floor, just about an hour earlier. I knew that’s what he was thinking too, as he pressed me back up against the side of the car, seemingly unable to resist. We both chuckled as he kissed me again, reaching up my dress again to flick the tail of the toy through my underwear briefly before pulling back again. 

Mark

I was finishing up a call at work a few days later when I got a text from Sam. 

Sam: I’m at work now, sitting in the guard chair with Eggy in :) 

We’d landed on that name for the toy at some point. Not the most creative, but it felt like we needed a name to refer to it, rather than “the toy.” It / He was quickly becoming a prominent fixture in our conversations as Sam was working through the to-do list / scavenger hunt. 

Sam: Any free time between meetings this afternoon? ;) 

I smiled at my phone, deciding to wrap up the call in favor of the chance to play with Sam a little. So far, I’d been able to help her check off each place on the list and I wanted to continue that record. 

I texted Sam back to let her know. 

Mark: Give me a couple minutes ;) 

I clicked to open the app and connected to Sam’s toy as I wrapped up the call, already requesting to control the vibrations. Sam allowed my request right away, and then I was in. I started her slow as usual, choosing a low intensity setting on one of her favorite vibration patterns. 

We’d quickly discovered that there was also a chat function through the app itself, which made it easy to communicate while we were playing, without having to toggle back and forth to texts. I saw the message notification icon pop up as I was adjusting the vibration settings and clicked through to read it and respond. 

Sam: hi :) 

Mark: Hi, my slut

Mark: Feeling tingly in that lifeguard chair? 

Sam: I am 

Sam: Thinking about the time you turned me on with your onslaught of messages and caused me to run into the guard office to make myself cum during my shift :P 

Mark: Mmm

Mark: I want to do that again

Sam: :D 

Mark: Just finishing up a call now

Sam: Okay, take your time ;) 

I didn’t take my time, though. Feeling impatient, I brought the call to an abrupt end, pretending to have another emergency come up. Then I turned my attention back to Sam, turning up the intensity of the vibrations to get her attention and let her know I was back. 

Mark: Think you’ll be able to sneak off again? 

Sam: Maybe… only one swimmer now 

Mark: Mmm

Mark: What are you thinking about?

Sam: Still thinking about that other time I came for you during my shift

Sam: And the time you met me here as I was getting off at the end of the night and fucked me in the office

Sam: And getting excited for the next item on the list… swim lessons :P 

Mark: Mmm, yeah I’m excited about that one, too :) 

Mark: Thinking about you wearing Eggy all morning, and how turned on you’ll be by the time we finally come

Sam: Yeah :) 

I turned the vibrations up more. 

Mark: Might have to come up with an excuse to sneak off and fuck you after 

Sam: Fuck

Then a knock on my office door jarred me back to reality. My coworker Andrew poked his head in, and I clicked my phone off and put it down in reaction, spinning back to my computer to act like I was working.

“Hey,” he greeted. “Everything okay? What’s the emergency?” 

He’d been on the call too, and was clearly checking up on my excuse for hopping off so abruptly. 

“Oh, it’s actually not a big deal. I just realized I still have to finish this spreadsheet before the end of the day and wanted to get off that call. You know how that customer is. She could keep us on all fucking day just complaining about random shit.” 

Andrew laughed and agreed, but also seemed to pick up on my quick cover-up. He stepped into my office and nodded his head to my computer screen. “You know that spreadsheet isn’t due till Friday?” 

“Oh,” I stalled, trying to figure out how to pivot my terrible excuse. “That’s right. I don’t know what I was thinking.” 

He gave me a knowing look. “So, who are you texting with? It’s still not Monica, is it?” He closed the office door and made himself comfortable in the chair on the opposite side of my desk. 

I laughed a little, deciding to just give in, knowing I was busted. Andrew had been the only guy to know about another affair I’d had a couple of years earlier with a woman who still worked with us in the office part time. I guess he caught on to my bullshit pretty easily. 

“No, it’s not Monica,” I answered. 

“Good. I was hoping you’d learned not to dip your pen in the company ink after that blew up.” 

“Yeah, no shit,” I agreed. 

“So?” he pressed, a smug, insistent look on his face. “C’mon, don’t hold out on me! Who’s the new girl?” 

I smirked and shrugged, deciding to give him what he was asking for. “Her name’s Sam,” I answered, feeling a little excited to actually tell someone about her. “She’s a student at DePaul.” 

Andrew started cracking up. “Of course you’re fucking a college girl. Damn! Good for you, man. I don’t know why Heather puts up with your ass.” 

I scoffed. “Yeah, well, she probably won’t if she finds out. So keep your fucking mouth shut. Please.” 

He laughed. “You know you don’t have to worry about that. And there’s no way I’ll be the reason it blows up in your face again if you’re still being this obvious. Didn’t you learn anything after last time?” 

I knew Andrew was right, and that I had to be more careful. Even more than I thought I was being, already. But despite how easily he’d just caught me, I also knew I was being smarter about everything than I had been with Monica, and suddenly felt a need to prove it. I was pretty proud of my idea of getting the toy for Sam, using the same app that I had for Heather’s. So, I showed him. I told him all about it, and all the places Sam had worn it already. Then I showed him the app and the messages I was exchanging with Sam currently, as she wore the toy at work. 

“Shit, that’s pretty hot,” Andrew admitted. “She’s using it right now? And this controls it?” he asked with a smirk. 

I knew right away what he was thinking, but wasn’t sure how I felt about it. I guess it took me too long to answer though, and he just went for it, trying out some of the different vibes and the intensity control. “I wonder if she’ll be able to figure out it’s not you on the other end of this thing?” 

I just shook my head and sat back, letting him have his fun. “We’ll see.” 

Andrew laughed then, turning the phone back to me and holding it out so I could see that Sam had sent another message.

Sam: Fuck, you’re going to make me cum right here in the seat if you keep that up :P 

I shook my head at him. “I guess you’re a natural.” 

“Guess so,” he smirked, continuing to change up the vibration styles and intensity levels haphazardly. 

I wouldn’t be surprised if Sam noticed something different. Even after just a couple weeks of playing with the toy, I’d figured out some patterns and moves that she liked and what helped her to cum. So, I could also manipulate that to tease her and draw it out when I wanted to, which had been my plan while she was at work. It seemed like Andrew had other plans, though. 

“Alright, calm it down, man. I don’t want her to get in trouble at work.” 

“I don’t know. I think she’s liking it,” he responded, showing me some more messages Sam had sent, still gloating. 

Sam: My legs are squeezing together so tight right now

Sam: Clenching hard

“Should I ask her if she wants me to stop?” he teased. 

I just shook my head. I knew I should get the phone back away from Andrew before he took it too far, but seeing Sam’s responses gave me pause. Maybe it was exciting for her, feeling something different like that, rather than my usual teasing patterns. I was curious to see what else she’d say, and excited by the prospect of my coworker making her cum while she thought it was me. I wasn’t sure how fucked up that would be, or whether Sam would be pissed if she found out. But my horniness won out in the end, and I let him go for it. 

“Go ahead,” I conceded. “Do what you want.” 

His grin widened, eyebrows raising in excitement as he typed out a message back to Sam. 

I decided not to even ask. I knew I’d be able to read the messages back later anyway and had decided to just sit back and see what would happen. So all I got were Andrew’s occasional muttered comments, like “This is fucking crazy,” and, “I’m surprised by how hot this actually is. I might have to pick one up for Nicole,” referring to his wife. 

The awkwardness came in as I noticed him getting hard right there in my office. I couldn’t really blame him, though. Chatting with Sam and teasing her with the toy always had that effect on me, too. 

Rather than sitting and watching Andrew’s hard-on growing, I turned to my computer to actually do a little work, grazing through some emails and working on the spreadsheet a little while he chatted away with Sam. 

Almost a half hour later, he finally clicked off the phone and slid it back across the desk to me with a big smile on his face. “That was hot. I think I got her.” 

I gave him a questioning look. “In the lifeguard chair?” 

“Yeah, that’s what she said,” he shrugged. 

I was a little surprised that Sam would actually let herself cum that way, out in the open like that at work. She’d never let herself go like that with me before. But then again, she’d never had Eggy in when I’d teased her the previous times. And I guess we’d been building up to it with everything else on the sexy scavenger hunt list so far. 

I resisted the urge to click the phone on and check the messages right away. 

Andrew seemed to know what I was thinking. “I told her you had to get back to work,” he said, answering my unasked question as he got up to leave. “And that you’d call her later,” he added with a wink. 

“Okay,” I said, shaking my head.  

“Can’t wait to hear how that goes! Good luck with the spreadsheet, man!” Andrew yelled over his shoulder, as he finally left my office. 

Once I was sure he was really gone, I couldn’t resist opening the app again and reading the messages that Andrew and Sam had exchanged. There wasn’t anything that I found offensive, although it bothered me a little to know that someone else made Sam cum in her guard chair for the first time. But I knew I’d been the one to allow it, so I couldn’t exactly get mad about it after the fact. 

As I read on, I realized it was actually hot, reading Sam’s sexy chat with another guy. It felt similar to the jealous yet turned on feeling I got when I thought about her hooking up with her neighbor. Maybe less of the jealousy, since this time she thought it was me she was chatting with. It made me feel more curious about seeing her flirt with other guys, though. And maybe more. That one was coming up soon on the list, too. 

***

Later that night, Sam and I had our usual chat, making each other cum before bed. She was the first one to bring up our Eggy escapade from earlier. 

“That was interesting today,” she started.

“What was?” I asked, playing dumb. 

“When we were chatting during my shift. The way you were controlling the toy felt… different, I guess.”

I couldn’t help smirking, but also felt a little nervous about how Sam would react when she heard the truth. 

“Good different?” I asked, sort of teasing, but also curious.

“I don’t know… I mean, you made me cum pretty hard, so I guess it was,” she laughed. 

“I didn’t, actually,” I said, deciding to just tell her the truth. 

“Umm, I think you did. Trust me, I was there.”

I laughed with her, but then tried again. “So… I have a confession to make. One of my coworkers came into my office and kind of caught me ending a call early to chat with you, so I ended up telling him about you and the thing with Eggy. And then he wanted to see the app, so I showed him, and he saw our chat, too. And one thing led to another until he sort of took over chatting for me. So, he was the one who actually made you cum today. Pretty hard, apparently.”

There was silence on the line. Enough that I had to check if Sam was still there, or whether she’d hung up on me. 

“I’m sorry,” I tried. “Was that a really fucked up thing to do?”

“I don’t know,” Sam admitted. “I think I’m just surprised, and a little embarrassed, maybe… Was it your idea or his?”

“It was his. But I realized that I kinda liked it, too. Similar to how I enjoyed hearing about what you did with Chris, maybe. I think I like to think about you being with other guys like that. Especially when I’m telling you to, or at least allowing it, if that makes sense. Although it sounds kinda bad when I put it that way.”

Sam laughed with me on that one. 

“I guess I’m proud of myself for noticing the difference,” she added. “Not that I can claim that I actually predicted that you’d handed your phone off to someone else to control Eggy and make me cum. But I could tell something was off. I need to go back and reread the chat now.”

I laughed again. “So you’re not mad?”

“I don’t think so,” she answered. “I guess it is pretty exciting to think about. What did he say when you told him everything? And is that going to cause you problems, with him knowing? Does he know Heather, too?”

“They’ve met a couple of times. I’m sure that won’t be an issue, though.” 

“Okay, that’s good.”

“He said it was hot, by the way. I’m pretty sure he was getting hard as he was chatting with you.” 

Sam laughed. “That wasn’t awkward for you? Just watching him chatting with me and getting hard?” 

“I wasn’t really watching,” I laughed. “I kept myself busy with work and read it back after.” 

“Okay,” she chuckled. 

There was a bit of a pause. Then I pressed things a little further. “Think you might want to try something like that again? Or maybe more than just chatting with another guy?”

“Well, that depends. Will I know it’s happening next time?” Sam joked.

I laughed. “Yeah, I guess that would be okay.” 

“I think it could be fun. Is that really what you want? I wasn’t sure, after everything with Chris…” 

“I was thinking about you with other guys, not Chris,” I added quickly.

“Okay,” Sam laughed, sounding a little nervous. “Yeah, we can try.” 

“Good,” I smiled. “Because I want you to get fucked by other guys. I want to watch you out flirting and picking someone up. Then I want to hear all about how you suck his cock, how he fucks you. I want you to be such a slut for me.” 

I could hear Sam’s breathing getting harder through the phone. 

“You know that’s coming up on the list,” I added.

“Well, it says ‘flirting’ with another guy,” Sam said. “Are you amending the list? Or adding to it?” 

“I do want you to wear Eggy while you’re talking to someone else, and flirting. Probably at a bar. I want to be controlling it from across the room while I watch. And maybe then you can take him somewhere to suck his cock while you’re still wearing it.”

“Would you want to watch that, too?” 

“Of course I would. But I’ll settle for hearing about it afterwards, if that’s what works out, logistically.”

Sam laughed a little. “Okay.” 

“Getting excited?” I asked, smiling. 

“I am, yeah.” 

“Touching again?” 

“Yes.”

“Mmm. I want you to cum again. Touch yourself now, thinking about how I might watch you make another guy cum.” 

“Fuck… okay,” Sam agreed, easily. “Touching now.”

“Good slut. Tell me what you’re thinking about.” 

“I’m just thinking that I really want that. I want to suck a stranger’s cock, knowing you’re watching me do it. Then I want you to take me somewhere else in the bar, or right outside or something, and fuck me right there. I’ll be so wet. I know I’ll feel like I just need you to fuck me after that.” 

“Yeah? Think your slutty pussy will be dripping from having a stranger’s cock in your mouth?”  

“Yess,” she moaned. “Fuck, I feel close again already. You’re making me so wet.” 

“My cock is so hard again, too. I wish I could feel your wet pussy right now.” 

“Fuck, so do I… I need you.”

“Get your dildo,” I commanded, reaching for more lotion and stroking my cock faster. “Fuck yourself hard and fast, just like I want to fuck you right now. Make yourself cum as fast as possible.”

Sam moaned again and then there was a rustling sound as she must’ve been reaching for her toy drawer. Then the sound of the dildo clicking on, the loud buzzing easily audible through the phone, at least until she pressed it down under her blanket, between her legs. 

“Rubbing it on my clit… between my lips… now pushing it inside,” she narrated, knowing from experience that I’d want to know how she was using the toy. “All the way, deep inside right away… Imagining it’s your cock and you’re thrusting hard and deep.”

“Yes, just like that. I want to fuck you hard and fast. Just using your pussy to cum deep inside you.”

“Oh, fuck!”

I could hear the wet sloshing sounds as Sam speedily pumped the dildo in and out of her wet hole. That sound, together with the mental image I had, got me suddenly close again. 

Before I could even tell her so, she whisper-moaned into the phone, “I’m cumming!” 

I groaned, squeezing my hand tightly around my cock as I continued stroking, imagining the feel of her pussy clenching and tightening around me. “Fuck, I want to fill that pussy up.” 

Sam continued moaning and breathing hard as she finished cumming. “Yess, fill my pussy with your cum. I want to wear it around inside of me all day again. That was so hot when you used Eggy to hold your cum inside me after you fucked me at your office. Give me another big load like that one.”

“Fuck, cumming!” I grunted, feeling the first spurt shoot from my tip with her words. 

“Mmm,” she moaned, listening to me finish. 

“Don’t make plans for Saturday night,” I said then. 

“What do you mean?” Sam asked, a hint of a smile in her voice. 

“Swim lessons are Saturday morning, so we can cross number seven off of the list. Then I’m taking you out to get number eight.”

“Really?” 

“Yes really. Unless you change your mind.”

“No, no!” she answered quickly. “I’ll make sure I’m free.” 

I smiled. “Good slut.”