Cassie Gets Some Overtime Ch. 02

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Cassie does a double!
4k words
4.58
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Part 2 of the 3 part series

Updated 06/07/2023
Created 07/29/2015
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*****

It had been several weeks since my encounter with Mr. Decker, but I had scarcely seen him since. I knew he was busy with the project we had been working on, but it didn't make me feel any less disappointed (or horny) with each passing day.

I certainly wasn't in love with the man, but I did have a strong attachment to his big cock and the effect it had on me. I was so horny at this point that I had already pleasured myself in the bathroom at work a few times this week, not to mention fucked myself with my vibrator (which didn't compare) almost every night at home since it that night with him.

It was the end of the day and I was debating on whether I should make the first move or wait for him to do it, when he roared for me from the doorway of his office.

"Cassie! I need you in here, NOW!"

The last of the workers had just finished punching out. They looked at me with half-pity and half-relief that it wasn't them as they filed out the door. I stood up and walked toward his office. I was a little nervous and VERY wet. I wasn't really sure what to expect, but I was hopeful. I walked in and stood in front of his desk. He threw a file across the desk at me.

"What the fuck is this?" he snarled, "This is the most poorly put together proposal I've ever seen. I gave you the information you needed, so I don't know how you fucked it up so badly!"

I picked the folder up and opened it, my hands shaking slightly. Looking it over, I could allow that it wasn't my best work ever, I had been pretty distracted lately, but I certainly didn't deserve this reaction! I was totally confused. What was he trying to get at?

"I'm sorry, sir," I said, "I'll look it over first thing in the morning and have the revised copy on your desk by 9."

"I don't think you're going to get off that easily, Cassie." He stood and started unbuckling his belt. I could see a telltale bulge in the front, giving away his aroused state.

I relaxed. Now I knew where this was headed. "Maybe I could help you with that? Would that make things better?" I said coyly, gesturing to his crotch.

He frowned and stopped unbuckling. "You'd like that wouldn't you? This big cock deep in your pussy? But I don't think you'd learn any lessons that way. Maybe I should just fire you. I'm sure it wouldn't be that hard to find someone else. Someone who even knows what the fuck they're doing!"

Now I was confused again. Was he serious?! I didn't think the proposal was that bad! It could've used a little fine tuning, but to FIRE me over it?! That was a bit excessive!

I looked down at my hands. "I-I'm sorry," I stammered. "Please don't fire me!"

"I don't know, Cassie." He looked dangerous. "How far are you willing to go to keep your job?"

"I'll do anything!" I blurted out. I immediately thought about the implications of what I had just said. Was I really willing to do anything to save my job? No, I wasn't. I could easily get a new job with the experience that I had. However, I had a good idea of what he might have in mind and the thought of succumbing completely to this man's desires left me weak in the knees. Was I willing to do anything in hopes that I might be able to experience the level of pleasure I had felt the last time around? Absolutely!

He raised an eyebrow, "Anything?" he asked.

"Anything!" I repeated, anxiously. I was a nervous about what he had in store, but my curiosity and excitement got the best of me.

"Take your clothes off! " he barked. His dark eyes grew darker. "This is going to be for my pleasure, not yours. This is a punishment. If you do get any enjoyment out of it, it is purely coincidental."

As I listened to him, I stripped my clothes off unceremoniously. I was turned on by his little speech. I knew he meant business, but I also knew whatever he did to me, I would enjoy immensely. I got a lot of satisfaction out of pleasing him.

He walked out from behind his desk, his belt undone. "On your knees," he ordered, pointing at the floor in front of him. I dropped to the floor, awaiting his further instructions.

"I think you know what to do next, Cassie," he said, his voice frightening low. I undid his pants and dropped them to the floor. His cock was only half erect, but it was still impressive. I wrapped my lips around it and took as much of it as I could into my mouth.

"Not good enough!" he growled as he grabbed my hair and choked me with his huge cock. I tried to pull back, but he used my hair to grind my face onto his dick. "Swallow it, slut!" he said. I knew I would have to start swallowing him while he was half hard or I wouldn't have a shot. He was merciless.

I relaxed and opened my throat. He shoved his way in until I gagged, pulled out slightly, then slid his cock fully in and held it there. I breathed in noisily through my nostrils. I could feel his cock thicken in my throat. I moaned around him. He began to slowly slide it out, then slammed it back in. He did this a few times, my mouth salivating more and more with each thrust. When his cock was well lubricated, he started thrusting hard and fast into my throat. I grasped at his hips and dug my fingers into his muscular ass cheeks. My eyes were watering and saliva was running down my chin and throat onto my breasts. I looked up at him and, as we made eye contact, he slammed his cock into my throat with a particularly hard thrust and then pulled out.

He pulled me up so I was still on my knees, but no longer sitting on my feet. He reached down and tweaked my nipples, hard. I squealed. He ignored it and continued manhandling my tits, squeezing them and kneading them with his rough hands.

"God you've got some beautiful tits." he said as his slid his cock into my cleavage like it was the most natural thing in the world. He squeezed my tits around it, his thumbs grazing my hard nipples. My breath caught as a jolt of pleasure shot down to my pussy. He began furiously pumping his hard dick up and down in my cleavage, my saliva acting as a lubricant. The head of it hit me in the chin with each thrust. I bent my head down to catch it between my lips each time he thrusted up, just catching the head with a hard, quick suck before he pulled out with an audible "pop".

Finally he stopped thrusting, but kept his cock sandwiched between my breasts with most of it protruding towards my chin. I sucked at the tip of it, swirling my tongue around and then tonguing his sensitive frenulum as I bobbed my head the best I could.

"God that's a beautiful picture," he groaned, "but I'm not finished with you yet!" He seemed reluctant to remove his cock from my ample cleavage and my talented mouth, but he finally did and pulled me to my feet. He stroked his thick cock while pushing me behind his desk. Standing behind me, he kicked my feet into a wide stance and pushed me forward until I was bent over his desk, my ass in the air and my nipples grazing the desk beneath me. He slid one thick finger deep into my waiting pussy.

"You're a wet little slut aren't you?" He sounded pleased. "I know how much you love it when I fuck that sweet mouth of yours!" I let out a low moan. He pulled his finger out and a second later, he appeared in front of me. "You want something in your mouth, slut?" he asked. I opened my mouth thinking he wanted to fuck my face again, but instead, I felt a piece of cloth being shoved in!

It took me a second to realize that the cloth was my panties. I could taste my pussy on them. It was different. A little musky and very erotic.

While I had been getting acquainted with my own womanly essence, Mr. Decker had resumed his position behind me. "Hold onto the edge of the desk above your head with both hands and keep them there," he ordered me. I complied and I felt him slide the tip of his cock up and down my wet slit, being careful not to enter me yet. Every part of my body tensed, waiting for penetration.

"Fuck, Cassie," he murmured, "who knew that under that suit of armor you wear everyday, you were such a horny little bitch?" I wiggled my ass a little, trying to encourage him to penetrate me. He slapped the entrance of my pussy with his cock a few times, making a wet, fleshy thwacking sound.

"Oh I know want me to fuck you in this tight, wet hole," he growled, entering me with just the tip. I tried to push backwards to impale myself on his huge erection, but he grabbed my ass with one hand and stopped me, using his thumb to pull my ass cheek outward. He slid his cock upwards until it was pressing on my asshole. "But maybe I want to fuck this tight, little hole!" he said as slowly leaned towards me, the blunt head of his cock putting more and more pressure on my virgin asshole.

I had never had anal sex before, but after he had penetrated my ass with his finger during our last encounter, I was curious. However, the thought of losing my anal virginity to his mammoth cock was still a frightening concept. I took a deep breath and tried to relax, but he had barely gotten half the tip in when I experienced a searing pain and panicked.

I lifted my body from the table, turned towards him, and reached out to stop him. He immediately pushed me back down on the desk, following that with the resounding crack of his hand hitting my ass. I shrieked around my panty gag and resumed my grip on the edge of the desk. He began to rub my now stinging ass cheek.

He chuckled softly, "I wasn't going to ruin your pretty little ass, Cassie. Not yet anyway. I just wanted to see how you'd react. You let me go farther than I expected you to... But I did tell you to keep your fucking hands on the desk!" He slapped my ass again. I let out a whimper and flinched a little, but I kept my hands in place.

I thought about this for a second. He knew that, with the gag in my mouth, I had three options: turn around to stop him, pull the gag out and yell, or let him fuck me in the ass. I knew what happened when I chose the first option, and my guess is that I would've gotten the same outcome if I had chosen the second one. So it was get spanked, or have my ass violated. He was a twisted individual.

I was incredibly aroused thinking about what this brute of a man could do to me. In fact, I was so wet at this point that I could feel my juices starting to trickle down my thighs. I didn't have to wait much longer. I felt him at my entrance and he was buried in my tight pussy with one thrust.

"Like a glove," he grunted.

I moaned around my gag and pushed back into him. He didn't stop me this time. He started with long, languid movements, pulling almost all the way out before sliding deeply back into me. I let out a muffled wail. His cock filled me in a way that I had never felt with anyone else. I couldn't get enough of it, it was like a drug.

I began to rock my hips, riding his cock as he slammed it into me. He grunted and began to pick up speed, holding me by the hips and pulling me into him, slamming into me over and over.

I exploded on his cock. I screamed around the gag. I gripped the desk so hard my fingernails dug into the wood. When it was over, I was a whimpering mess. I rested my face on the cool desk, raising my ass high in the air, as he continued pounding me from behind.

"B-Boss? CASSIE?!" I thought heard someone say. At first I thought I had imagined it, like some kind of hallucination. Either way, real or not, in my orgasm induced stupor, I didn't care. Let them watch.

"Adam, what the fuck do you want? I'm kind of in the middle of something!" Mr. Decker snarled, continuing to pump his cock into me without missing a beat.

"Umm...uh... I'll just talk to you tomorrow," I heard Adam say.

"The fuck you will," Mr. Decker barked. He lifted my head from the desk by my hair. I saw Adam standing in the doorway through heavily lidded eyes; he looked wide-eyed and bewildered, but intrigued. "She really loves a cock in her mouth, and I'm a little busy at the moment," Mr. Decker told him.

I knew Adam a little from work, it was a large company, so I wasn't well acquainted with everyone. He was in his mid 20's- a good looking guy, but very immature and a bit of a cocky asshole. Typical of a lot of guys his age. I had never seen him speechless before. I tried to imagine the scene before him through his eyes.

He would see Mr. Decker pummeling me so hard from behind that the desk was shaking and jumping, his fist in my auburn hair, lifting my listless head from the desk. This would give him a good view of my creamy tits pressed against the desk beneath me, bouncing vigorously with each thrust. He would see me holding onto the edge of the desk for dear life, my dark eyes somewhat glazed over, my pink panties stuffed in my mouth.

The visualization of this made me overcome with desire, and I came. It wasn't as hard as the first time, but I knew Mr. Decker felt it as I quaked and seized around him. I closed my eyes and let out an animalistic groan.

"Oh god yeah!" he exclaimed. "Cum on that dick! What the fuck are you waiting for, Adam?! She's ready!"

Adam hesitantly pulled my panties out of my mouth. My lips were dry, so I ran my tongue over them, trying to entice him. I looked up at him seductively. I wanted his cock in my mouth in the worst way and I knew he had always wanted to fuck me.

"Yeah, Adam, what are you waiting for?" I asked huskily.

CRACK! Mr. Decker's hand landed on my ass. I cried out. "Did I say you were allowed to talk?" he growled. I turned and glared at him, but I kept my mouth shut and my hands on the desk. He pretended not to notice and continued to assault my pussy with his rock hard dick. When I turned back to Adam, he had his cock out and was stroking it in my direction.

I could tell he was a nervous and I couldn't really blame him given the situation. I tried to smile at him encouragingly, but he was fully absorbed in trying to achieve an erection. I reached out to give him a hand, but as soon as my hand left the desk, Mr. Decker's hand landed on my ass. Hard.

"Fuck!" I shouted.

Another crack. I bit my lip to keep from shouting again. My ass cheeks were on fire and my eyes were watering involuntarily, but my pussy was gushing. I felt the tip of Adam's cock pushing at my lips. I opened my mouth to let him in.

He wasn't as large as Mr. Decker, but I figured not many men were. His cock was a little larger than average, smooth skinned, with a slightly tapered tip. It was much less imposing than Mr. Decker's massive, veiny cock with its large, purplish, mushroomed head.

He pushed his cock in past my lips and teeth until the smooth head was resting on my tongue. I sucked on it enthusiastically, trying to take him farther into my mouth without pulling him towards me with my hands or pulling off of Mr. Decker, who was still slamming me from behind. I heard him take a sharp breath in. I swirled my tongue around the tip and lapped at the underside frantically. I wanted more!

I made a muffled noise of frustration that Mr. Decker must've heard because he boomed out, "Give her more than that, she can definitely handle it!"

More cock slid in until my mouth was full. It was a delicious feeling, being this filled with cock; Mr. Decker's giant member hammering away at my wet pussy, Adam's smooth young cock in my mouth. I was in heaven!

I started to bob my head, sucking with all my might and gently curling my tongue around the underside of his girth. I heard him emit a low groan and felt him place his hand lightly on the back of my head. Mr. Decker reached down and began rolling my clit between his rough fingers. I spread my hips and thrust my ass out as much as I could to ensure he was reaching balls deep penetration. I could feel an orgasm starting to build, but it wasn't quite ready to boil over yet.

All of a sudden Mr. Decker thrust fully into me and stopped. I didn't even have time to react before he pushed me forward causing me to engulf more of Adam's cock, the head hitting the back of my throat. I knew what Mr. Decker wanted from me-I wanted it too- but it depended on Adam.

I leaned forward as far as I could, pulling slightly off of Mr. Decker, and felt Adam slide into place down my throat. It was a cakewalk after swallowing Mr. Decker's giant dick. I let out a low moan that I knew would cause pleasurable vibrations around his shaft, but I didn't move, hoping he would get the hint. He did. He moaned and started pumping into my face, gently at first, but then increasing speed and roughness.

I slowly eased back onto Mr. Decker's hard cock and Adam moved forward with me, continuing his assault on my mouth his hands on the side of my head. Mr. Decker resumed pounding into me and rubbing my clit vigorously. I could feel an orgasm building again and I hoped this time he would allow me a release.

When he stopped rubbing my clit suddenly, my body tensed in frustration. But then I felt something pressing on my asshole, so I relaxed and let him slide his finger in. He didn't move it, just kept it inserted in me. It was uncomfortable at first, but after a few minutes I had grown accustomed to it and he began to wiggle it gently, then slowly slid it back and forth. This sensation, with the combination of Adam furiously fucking my throat and Mr. Decker hammering my pussy from behind, pushed me over the edge.

I erupted into the most intense orgasm I had ever experienced. It shattered me to my core.

I began to buck and grind involuntarily against Mr. Decker's cock and finger, my pussy spasming wildly and my clit twitching in a frenzy. My body felt so tense that I was sure that any additional stimulation would send me flying into a million pieces.

I heard Mr. Decker's voice say "Oh fuck," in a hushed tone. I let out a long wail around Adam's cock, which I was really struggling hard not to choke on.

Thank God my vocalization made him begin his own orgasm, because I couldn't control my breathing any longer. He pulled out of my throat, grabbed the base of his cock and pumped into my mouth in short, jerky thrusts, spurting his hot load into my mouth. I greedily gulped down what I could, but some of it leaked out around his still thrusting cock and my tight lips and ran down my chin. He finished cumming and pulled out.

I collapsed onto the desk, Mr. Decker still ramming me from behind, his finger now slamming into my ass. He continued this for a few more minutes. This man had more stamina than anyone I had ever been with before. Finally, he pulled out of me and I felt his large hand squeeze my ass cheek, his fingers digging into my flesh as he grunted and then spurt after spurt of hot liquid unloaded onto my ass and lower back.

I heard Adam exclaim, "Holy shit!" as he caught the first glimpse of his boss's enormous member. I felt sore, weak, and empty, but incredibly sated.

Mr. Decker and Adam left the room with me still bent over the desk. I heard them have a brief conversation and heard the front door open and close. Mr. Decker returned alone. He toweled me off, wiping his copious amounts of cum from my back and ass, then he pulled my aching arms from the desk and sat me in his chair. He crouched before me, gently massaging my shoulders.

"Are you ok?" he asked softly.

I responded with a satisfied half-smile, "Mmm hmmm."

"You were incredible," he said, almost reverently. "Let's get you dressed so you can head home and get to bed. You're going to be sore tomorrow!"

He helped me on with my clothes since my legs still weren't very cooperative and he was getting dressed himself when he turned to me and said, "Actually, if you want, you can have tomorrow off, paid.

"No, I'll be fine," I replied, "Besides, I need to review that proposal, remember?"

He grinned sheepishly, "That proposal wasn't really that bad. Not the best I've seen you do, but it'll work. I was really using it as an excuse to make you stay late."

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