Office Trouble - Part 2

Stacy takes a big leap by accepting what happened and asking Jared for a second round.

“Be patient. I know she will fuck up soon enough, and by then you are the first to know.”
“How do you know for sure? You made a promise!”
“I know I did. I’m working on it. Like I said, be patient. If nothing happens, I will make her fuck up.”

~ ~

It had been two weeks since Jared had fucked me on his desk. It was forced, but I didn’t fight him. You see, if I didn’t do this for him, he would fire me. I had come in late multiple times, messed up something with different accounts and was on the brink of losing my job. With my sky high loans, my rent and basic living expenses, I needed this job. It paid well, and it was hard to find something new. So I endured. And to be completely honest, it hadn’t been the worst experience. The build up to it was worse than the actual deed.
And now that we’re sharing secrets, I had started to fantasize about the size of his cock late at night. It was an absolute beast and I had been sore for days after he had fucked me. Every time I moved, I felt it. It made me hungry. I wasn’t wearing panties under my skirts to work anymore, part of the arrangement, and I had noticed I started to look forward to the early morning check-ins. I made sure I came in earlier than usual, eager to feel his fingers between my legs. Even if he didn’t enter my pussy, feeling him there was a very enjoyable way to start the day.

The office was still empty when I came in that morning. I placed my bag on my desk, turned on my computer and walked towards Jared’s office. The door was open, but I knocked anyway.
“Good morning, Jared,” I said, a bit too cheerful. He looked up and nodded, not saying anything. I walked towards him and quickly glanced through the window to see no one had come in yet. Without needing his words, I stood beside him, opening my legs slightly, so that he could feel me up. I started to love the ticklish feeling of his fingers sliding up my inner thigh, all the way to my pussy. This morning, he surprised me by parting my lips and pushing a finger inside me. I was so surprised, I couldn’t hold back a gentle moan.
“Hm, someone seems to like these early morning sessions.” He started to gently fuck me with his finger, adding a second one to my tight hole. I had to place my hand on his desk to steady myself. I couldn’t lie, with my head swimming like this.
“Yes, Sir.” He found my most sensitive spots and quickly brought me to the edge of an orgasm, surprising us both this time. But at that moment, I saw movement. Someone walked in. Jared quickly removed his fingers and sadly I stood up straight again.
“Go back to work.” His voice was all business again and I nodded, going back to my place. Jared was already typing before I had even walked out the door. With flushed cheeks I sat down, wiggling in my seat, looking for that little bit of extra gratification to maybe pull me right over the edge, but to no avail.

I had seen the looks Tom gave me, whenever we crossed paths. But we never spoke, besides the polite ‘good morning’. Tom was an older gentleman, probably early fifties. We both knew he saw me getting fucked on Jared’s desk late that night. I was wondering what he thought of me. Did he really think I laid there because I wanted to? I didn’t know the story Jared told him. He wouldn’t have been honest, maybe he told Tom that we were secretly dating? I don’t know. I shrugged it off as I grabbed myself a cup of coffee. To be honest, I loved the mornings with Jared’s fingers on me. I preferred the mornings with Jared’s fingers IN me. But I started to secretly long for a possibility to have Jared’s cock in me again. Stretching me so wide it hurts. Entering my pussy so deep that my belly bulges. Filling my pussy with so much seed, I would still be dripping by the time I came home. I rubbed my thighs together as I leaned against the wall in the break room, my eyes slowly moving over the tables and the kitchenette. There were several people out and about, but all I could think of were the different surfaces and me in different positions with a cock stuffed in my pussy. Fuck, I needed to be careful. Being so close to an orgasm this morning made my head swim. I needed to focus. No, I needed Jared’s cock inside me again. I could just come late again, but who was I kidding? I wasn’t the bad girl on purpose. I had been raised right, so I would just go and ask him.

I didn’t have the time to speak to Jared that afternoon, and he left early for a meeting elsewhere. The whole evening and night, I was thinking of how to ask someone such a question. How to initiate.
By the morning, I still didn’t have an idea, so I decided to just go for it. I came in, just in time as the bus was running late, but I still made it. I turned on my computer, waited for it to start and pretended to send something to Jared, as there were already people around me. I knew he was looking at me, waiting for my arrival, but this needed to be done the right way. I walked to Jared’s office and knocked on the door.
“Jared, can we talk about that project? I would like to discuss the parameters. I sent you something.” I spoke loud enough that people would hear, making sure our story was still solid. My heart was pounding though.
“Sure, close the door behind you and grab a seat.” I did as he asked and pulled the chair closer to his desk, so I could look at his screen. Like every morning, I opened my legs wide, using the desk as my cover, and pointed at his blank screen. His fingers tickled the way up my leg again, meeting my wanting pussy. I was already wet this morning and he hummed in surprise.
“What is it you want to discuss?” he asked softly, as he used his fingers to open up my lips. He didn’t slip inside, like I hoped, but he kept teasing me. Dipping just a bit inside my pussy to put me on edge, but not giving me any pleasure. I had to clear my throat a few times before I could speak.
“I - well. I would like to ask…” I stuttered and I had to take a deep breath to gather my thoughts. Jared knew what he was doing to me. I realized then and there that these morning routines had been put in place to mess with my head. To make me want his touch. And in the end, to want his cock. If I wanted it, I needed to ask for it. “I would like to ask you to fuck me again, Sir.” My voice was soft and timid, and I knew I had to be blushing deeply. I saw his smirk and as a response to my question, he pushed one finger deep inside me.
“Like this?” I moaned softly, but shook my head.
“N-no, Sir.” I was out of breath from arousal. “Well, yes, but no… I…”
“Use your words. Be as specific as I need you to be when it comes to work.” I looked him straight in the eyes, the world around us forgotten as he kept slowly fucking me with one finger.
“I want you to put your thick cock in me, stretch me so wide it hurts. I want you to fuck my brains out, until I can no longer walk properly.” My blush deepened. My words had never been this vulgar, but he seemed to like it. He then pulled his hand away from my pussy and sat back in his chair.
“So the little slut needs more?”
“Yes, Sir,” I answered quickly, wiggling in my seat. I watched how he grabbed his phone from the desk, opening his digital agenda.
“I might have an opening tomorrow, after work. It’s Casual Friday, so wear something that would please me.” The fact that he was planning this in his agenda like I was a common whore, or just something unimportant made me ashamed, but I nodded and stood up.
“Thank you, Sir.”
“Oh, and touch yourself tonight. Repeatedly. But don’t come. I want you to be dripping with need tomorrow.” With a wave of his hand, he dismissed me as he typed something on his phone, not hiding the smirk.

The next morning, I arrived early at the office. I was wearing a dress, tight around my curves but still professional enough to wear at the office. I wasn’t wearing a bra with this, which I already regretted, as my nipples were poking through the material. It wasn’t that obvious, but you could see them if you really looked. There was nobody yet when I arrived, except for Jared of course. He was always early. I did my normal routine of firing up the computer and placing my purse on the desk, before going in to greet him.
“Good morning, Sir,” I purred, when I stepped into his office. He turned his chair towards me and smiled. I walked closer and sat down on the chair next to him. Shamelessly, knowing we were still alone, I opened my legs wide, so my dress would ride up completely, showing him my pussy. I spent a lot of time in the shower yesterday, shaving every last hair on my pussy, scrubbing and moisturising until I knew I was soft and ready for him. He leaned forward, placing a hand on my most private part.
“You really are a filthy little slut, aren’t you?” he said, and I heard the joy in his voice. I bucked my hips against his hand gently.
“Only for you,” I replied, letting lust drip from my words. I grabbed his wrist to hold him in place and leaned forward a bit, looking more serious. “I am not kidding. I am not this type of girl, but you did something to me. All I keep thinking about is feeling your hands against my pussy.” I pressed him closer, moaning softly as he rubbed the tip of his finger over my entrance. “All I keep thinking about is wanting your cock inside of me. I am not a slut, but I am a slut for you.” Jared smirked and nodded, still rubbing my entrance. I knew he was enjoying watching me squirm in my seat.
“Then be the slut tonight. For me. I want you to bring yourself to the edge each time you go to the bathroom today. But don’t come. You know where to find me once everyone is gone.” I nodded and pouted a little when he pulled his hand away from me. Feeling empty and needy, I stood up, pulled my dress down and made my way back to my seat, swaying my hips as I walked.

The day was hard. So hard. I had the feeling that I had soaked through the chair, I didn’t have much focus and Jane kept yapping about her kids. Yet I smiled. I stayed polite. I engaged in conversation. I tried to act as normal as possible, while my insides were burning because of my own arousal. Finally the moment came. The clock hit 5, and slowly my coworkers went home. One by one, the office grew quieter.
“Staying late again?” Jane asked, as she packed her bag. I nodded as I typed something on my screen.
“Yeah, it’s just this project that Jared needs me for. I don’t know how much longer it’s going to take, but it is interesting.”
“Well, you’ll have to tell me all about it soon, okay?” I hid my smirk and nodded. She would have a fit.
“Have a good evening, Jane.”
“You as well, Stacy.” I watched her leave and waited to be completely alone. When it was just my keyboard making sounds in this quiet evening.

It took ages when I finally closed my computer and stood up from my chair. I pulled my dress down a little, pinched my nipples to make them pop and took a deep breath. This was it. With confidence, I walked to Jared’s office. I didn’t knock, as the door was wide open. He was waiting for me. He had left the blinds open, because we both knew nobody would come in on a Friday evening. I stood in the middle of the room. Jared was just watching me. His eyes raked over my body. Very slowly, teasingly, I moved my hands to the small zipper at the side of my dress. I pulled it down, allowing the dress to fall open. I was still completely covered, but that wouldn’t take long. I wanted to feel his eyes burn on my naked body. I wanted to expose everything I had for him. So I let the straps of the dress slide over my arms, so the dress fell down and pooled at my feet. I heard the sharp intake of breath when Jared realized I had been bra-less the entire time. Riding the wave of confidence, I turned around and bent down at the waist, my ass pointed straight at him as I grabbed my dress off the floor. I hung it on his coat rack and turned back at him, standing in just my high heels.
“My god, woman,” Jared breathed, the bulge in his pants clearly visible. I walked towards him, feeling my tits bounce freely with each step. It felt so liberating to just do what I wanted to do. And right now, I wanted to feel his hands on my body. But I wanted to tease him as well. I leaned forward and took the keyboard off his desk, placing it to the side. The rest of the desk was already cleared as he waited for my arrival, but this was the only thing in the way. I turned my back towards him and immediately I felt his hands on my ass. So I leaned forward, hollowing my back and wiggling my hips as he followed the contours of my cheeks. His hands moved up, over my slim waist before pulling me back down, so I was sitting on his lap. He moved my body like I was a doll, wrapping his legs around mine so he could pull them open without using his hands. I leaned back against his chest, my arms behind his neck. I was fully exposed like this, and he took full advantage. He kissed and suckled on the side of my neck as he took a hold on my breasts. He kneaded them, rolling the already hard nipples and chuckled when my body squirmed. This time, I didn’t hold back with my moans.

While one hand kept playing with my tits, the other moved down slowly. In between my tits, down my sternum, slowly down to my flat stomach. I stretched my body towards his touch, silently begging him to continue his route down south. He inched down, over my belly button to my lower stomach. Using his legs, he pushed my legs even wider and finally, his hand reached the outskirts of my pussy.
“So soft,” he murmured in my ear, as his fingers danced over the shaven skin. He moved slightly to the side, moving over the edges of my outer lips, following the curve to the little spot between my pussy and my asshole. I was breathing heavily by now. He moved up on the other side, still moving slow.
“Please,” I sighed, my hips bucking up in a desperate attempt to feel him.
“Patience, little one, you will get what you want. But first, I’m going to fully explore you.” His fingers moved down again, same route, just slightly closer to my pussy. “Put your feet up against the desk.” I immediately did as he asked, letting my knees fall wide open. On his way down, he slipped lower this time, caressing my puckering asshole.
“Has anyone ever fucked you in the ass before?” He applied some pressure on it, so that just the tip slipped in. I shook my head, not feeling bothered at all.
“No, Sir.” He hummed, pushing in a bit deeper.
“If you please me tonight, I might take the honors then.” I didn’t know if that would actually be a reward, but right now I didn’t care. I just moaned as he pulled himself out of the tight hole, working his way up again. This time, he went straight through the middle. His finger slipped over the entrance of my pussy, very gently caressing the edges, going round and round until my body was shaking out of need. He then moved up, finding my clit.
“You are so willing, so ready,” he complimented, and I moaned in response. I was wetter than Niagara and I needed him inside me. But I loved this teasing. He drove me wild.
“Get down on your knees, princess. You’re going to get me nice and wet, before I give you what you need. You have been so good already.” I sighed at his words. It felt like my head was in the clouds. I was so turned on I couldn’t think straight, like I was high on lust. I wasted no second as I stood up from his lap. Jared turned his chair to the side as he took out his cock and I dropped to my knees in front of him. I gasped when I saw the sheer size of him. I had felt him inside me, but I hadn’t seen it yet. It was huge and gorgeous. Veiny. I could barely fit my hand around it, it was that thick. And length, oh god. Maybe three fists? Maybe more? Who cares, all I knew was that he was mine to please. I leaned forward and eagerly took the tip in my mouth, sucking him in deeply. He hit the back of my throat way too quick, but that didn’t matter. I did my best to give him all I had. I liked the length of his cock, sucked on the tip, and took his balls in my mouth. I even attempted a deepthroat, although I knew beforehand I would fail miserably. One day I would have to ask him to fuck my throat, with me laying on my back on his desk. That would be hot. I wiggled and looked up at him as I pushed him as deep as I could go.

“Well, well, well. What is going on here?” A voice broke through the space, and I immediately wanted to pull back and hide myself, but Jared was quicker. He grabbed the sides of my face and held me in place, using this interruption to change roles. Instead of me sucking and licking him, he gently fucked my mouth.
“Tom, glad you could join us. I hope you don’t mind we started without you.” I looked up at Jared in a panic, not understanding what was happening. He just smiled down at me. “Tom promised not to tell anyone, as long as he could watch up close. I told him yes, of course.” With his hands, he tilted my head back a bit and stepped closer, forcing his way deeper in my throat. I choked, taking a gaspy breath in between thrusts, but being able to respond. Jared saw me struggle and smiled again. “Once more, darling. Relax your throat. I’m going in deep.” I took a hasty breath, barely getting any time to prepare before he pushed in hard. My jaws hurt from how wide they were pushed, but I did feel Jared slip down my throat, pushing in deeper than I ever had a cock before. I couldn’t breathe, but I needed to trust him. Trust. I relaxed, keeping eye contact with Jared as he pushed just a little bit further, before pulling back. His cock was covered in a thick, creamy saliva and I coughed. Letting him fuck my throat would be a challenge, but it was one I wanted to take.

Jared pulled me to my feet, holding me steady as I tried to catch my breath.
“Go and take a look, Tom, while I get undressed.” Jared released me and stepped back. Tom immediately appeared in front of me. He gently wiped a bit of saliva off my chin, only to smear it on my tit.
“She is exquisite,” he mumbled, as he walked around me like I was something in an art show. Perfect round tits.” He grabbed both of them, using his thumbs to rub over my nipples. His fingers were rough, his touch greedy. “Gorgeous narrow waist and flat stomach.” His hands moved down, pushing against my sides as if he wanted me smaller. “Good hips to grab while you’re fucking.” His hands moved from my sides to my hips, but they quickly moved to my ass, almost holding me in an embrace as he massaged my ass cheeks. “And a glorious ass.” He squeezed hard before releasing me, and he guided me a few steps back, until I felt the desk against my skin. He pushed me down, so I was laying down and opened my legs. “Oh and won’t you look at this! Are you sure you are going to fit inside this tiny little pussy, Jared?” Tom laughed, as he used his fingers to pry my pussy open a bit. I did not like his eyes, nor his touch, yet at the same time I felt an odd tingling in my lower stomach. I might not like it, it did arouse me even further. Jared stepped into view, his hard cock standing fiercely upright. He chuckled as Tom and him switched places, and he laid his cock on my body. With his hips pressed against mine, his cock covered almost half my stomach. At least, it felt like that, because I didn’t see. Just the feeling of his hot skin against mine made me twitch.
“I am sure it will fit. And if not, I will make it fit.” He moved back with those words, so his cock slid down over my stomach and he lined the tip up with my pussy. Yes, this is it! In anticipation, I pulled my knees up and held my legs wide with my hands. Very slowly, just like last time, Jared pushed himself inside my tight pussy. This time, I didn’t hold back. My back arched off the desk as he slowly forced his way deeper inside of me. Just like last time, my insides stretched wide over his girth, burning as he pushed deeper. I gasped and winced, but he didn’t stop. He kept pushing firmly, until he was completely embedded deep inside me. I let out a big breath, trying to adjust to his size.
“I am impressed,” Tom said, but I ignored him. All I could focus on was the feeling of the huge cock sliding out of my pussy again, all the way, until he popped out. My body felt instant relief from not being stretched so wide, but I didn’t agree. Tom mumbled something else, but all I felt was the tip of Jared’s cock popping in my pussy again. I needed more. I needed it to hurt, I wanted to feel everything he had.
I lifted my head to look at Jared. “Hard,” I pleaded through gritted teeth. Jared nodded once, took a hold of my hips and slammed himself all the way in. I screamed at that, but it is what I wanted. He pulled himself back again, only to slam back in. Hard. Yes! Once more and my body exploded. Every muscle twitched as a huge orgasm washed over me. Jared adjusted his stance a little, before he started fucking me. Really fucking me, not holding back. With his arms around my legs, he pulled me into his deep thrusts.
“Tom, look here,” Jared panted, as he pointed at a spot on my belly. I knew I was bulging every time he pushed himself in as deep as he could go.
“My god,” Tom responded, as he placed a hand on that spot. The other hand slipped in his pants, and by the looks of it, he was rubbing himself. My eyes found Tom’s face and I bit my lip as I saw how his eyes were glued to the spot where Jared’s monster cock disappeared between my legs and to the spot under his hand that bulged every time Jared bottomed out. My tits bounced on my chest and I grabbed my own nipples, twisting them and pulling them. The feelings inside my small body were huge, and I didn’t know what to do with the pleasure and the lust that filled my veins. But Jared did. He released one of my legs and used it to grab my chin. He pointed my face right at him, telling me wordlessly to keep looking at him. He then suddenly slipped out of my pussy, slapped the sensitive skin hard and rammed straight back in. My skin burned from the stinging slap. With wide eyes I watched him doing it again. Pulling back, leaving me empty. Slapping me hard, right on my clit, only to move back in. The pain, the stinging. It was an overload of feelings. I was surprised when one of my hands was suddenly pulled away from my tits, and a mouth covered my nipple. Tom suckled hard on the little bud, his eyes cast down at the spot where Jared and I were one. When Tom bit down hard at the same time that Jared slapped my clit once more, I couldn't take it anymore. My body exploded. My back arched, my muscles contracted and a gush of fluid released from my pussy and covered Jared’s cock.
“Fuck, that was the hottest thing I’ve ever seen,” I heard Tom say, but I was barely aware of what was happening. All I felt was my body bouncing on the hard desk, the delicious pain between my legs and my nipple that was gently throbbing. “I’m going to come soon.”
“In here,” Jared said, as he pried my lips apart and pushed my face to the side. I didn’t protest when Tom’s cock appeared in front of my face. He pushed himself between my lips and I started sucking. Within a couple of seconds, I felt how he stilled, his cock twitching and my mouth filled with seed.
“Swallow,” Jared warned, as he saw a small trickle of cum slip out from between my lips. I immediately swallowed it all, sucking softly until I knew he was empty.
Jared was close too. I could tell by his movements that became slightly more erratic. He grunted, right before his cock started pulsating. I felt how thick spurts of cum filled my pussy, covering my womb. He came so much, that I already felt it trickling out while he was still in there, covering my asshole with his seed. Jared then stilled, panting loudly.

The room was quiet now. Tom was still watching my body, how I tried to catch my breath and slow down my heart rate. Jared was still buried inside me, but we didn’t speak. I felt how he slowly softened inside me, before he stepped back, his cock slipping out. Tom moved in between my legs, watching how my once tight little pussy was now gaping and raw. I knew it must be swollen and red, covered in white cum. Jared helped me up from the desk, before pushing me down to my knees. Quietly, I licked him clean, my chest still heaving from my heavy breaths.

“Thanks, Jared. You can count on my discretion,” Tom said, shaking Jared’s hand. Jared had put on his boxers and his pants, standing shirtless in the middle of his office. I stood naked next to them. To my surprise, Tom leaned forward and kissed me gently on my lips.
“And to you, beautiful. Thank you for allowing me to watch.” I wanted to say that I didn’t even know, but one look from Jared shut me right up. I just smiled and nodded. We both watched Tom leave, before Jared turned towards me.
“You did well. Now, tell me again how you’re only a slut for me? You loved being watched, didn’t you?” I blushed deeply, but nodded.
“I did. Very much, surprisingly.” I swayed a little when I walked towards my dress. I had asked Jared to fuck me until I could no longer walk, and it seemed like he really made an effort to achieve that. I took my dress off the hanger and stumbled back, holding the fabric in my hand.
“Did you mean that, wanting to fuck my ass?” Jared placed a hand on my cheek and I lifted my face up to him.
“Yes, princess. We will start your anal training soon.” It wasn’t a question whether I wanted it or not. It was going to happen. Facts. I didn’t know if I was looking forward to it. I could barely handle him inside my pussy. Or my throat. That reminded me...
“I want you to fuck my throat too,” I heard myself say boldly. I pointed at the desk. “On my back, head hanging over. I want you to fuck my throat until your balls slap in my face.” At that, Jared laughed loudly, before helping me in my dress.
“Making demands now? I will see what I can do. Now, let’s get you home, where I can fill you up once more before we start the weekend, shall we?” And with those words, he guided me out of his office, leaving the mess behind. I chuckled when I thought about what the cleaners would think when they came in tomorrow.

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Part 3 isn't written yet, but I'm willing to work on it if people are interested. Feel free to post ideas!