08/10/2019
I walked into my boss’s office. He was sitting in his chair, looking at his laptop when I coughed and he looked up. He smiled at me. “Hi Katherine. Have a seat.” I swallowed and walked over to his chair, my heels clacking on the hardwood floor. As I made my way across the floor he kept his eyes on me. I nervously sat down on the soft chair across from his desk and crossed my legs, my skirt riding up a little, showing the tops of my black lace garter tights.
“I called you here because of your email.” he said, closing his laptop. I nodded, hoping to god that I didn't look as nervous as I felt. “You said that you deserve a raise?” he asked, looking at me, then down at my boobs, which he did a lot. I guess I wasn't helping much. I always wore white, sheer blouses, unbuttoned so my boobs were close to spilling out, with tight black skirts that were just crossing the line of appropriate. You could see my black lace bra through my shirt.
I nodded at him. “Yes sir. I really need a raise, and I've been working really...hard.. as your secretary.” I gave him a smile, and he grinned. “Oh really?” he asked. “How badly?” he asked, eyeing my boobs again. I smiled at him, running my hand through my long blond hair. Maybe if I flirted more than usual, I could get this raise. “Really badly sir.”
He nodded and paused for a second, adjusting in his chair and smirking at me. “I think…” he started, leaning across the desk. “There could be a way I could give you that raise.” I smiled. “That would be great sir, thank y-” “But,” he said, cutting me off. “There would have to be an arrangement for a few weeks before I finalize anything.” I tilted my head, he was grinning like mad now.
“What kind of arrangement?” I asked him. He pointed up and down my body. “All this...is mine whenever and for whatever.”
What? I couldn't believe what I was hearing. “I don’t understand,” I told him, nervously running my hands across my leg. He smiled at me deviously. “I think you do. And I know how much you need this raise, so when I call you in here, you’re gonna do whatever I tell you to do. Do you understand?”
I didn’t know what to do. I really did need the money, and my boss was super hot. Blue eyes, short brown hair, definitely a six pack. Fuck it, “Yes sir, I understand,” I said, finally meeting his eyes. He grinned. “Good,” he opened up his laptop and looking up at me. “You can go now.” I nodded and stood up, pulling my skirt down as far as it could go, which was not far, just barely under my bottom. I could feel him staring at it as I walked out. I closed the door and walked over to my desk, sitting down in my chair. What had I just done?
The next few hours were hell. Waiting for my boss to call me in was torture. He hadn’t asked for anything yet. I spent the day answering phone calls, setting appointments, normal work. Around 8 everybody started to leave and I started packing my things to go when the door to his office opened. My heart started beating faster than it had ever before. I looked up and he grinned at me. “Katherine can I see you in my office?” he asked, already walking back in.
I wiped my hands on my skirt and walked through the door. He was leaning on his desk, his suit jacket off, his collared shirt unbuttoned at the top. “Lock the door.” I did and turned back around. His pants were unzipped and his shit was off. That was fast. He smirked and mentioned for me to come to him. “Come here kitten” he said. I slowly stepped towards him until I was facing him directly. “With your mouth,” he said, pulling out his penis. I almost fainted seeing it. I got down on my knees and took his dick in my hand. 10 inched, super thick, circumcised.
He put his hand on the back of my head and I looked up at him. “I don’t have all night darling,” he said, pushing me towards his throbbing cock. I took a breath of air as he pushed his dick into my mouth. The hard, hot skin filled my mouth, sliding down my throat and almost gagging me. I sucked on it, twirling my tongue around the tip. He moaned, shoving it further, making my eyes water. I kept my mouth tight and wet while he pounded down my throat. Suddenly he pulled out and I gasped for air.
He pulled my hair up and I quickly stood. He pulled down my skirt and I stepped out of it. He started unbuttoning my shirt, throwing it on the floor next to my skirt and unclasped my bra. My boobs spilled out and my hard nipples felt cold to the sudden exposure. He grinned, looking at them, pinching them with his fingers. I couldn’t help but let out a small moan. He looked at me, “You like that kitten?” He asked, putting his hands on my waist. I nodded. “Call me sir, and sir only. Answer when I ask u something.” He said, ripping my panties off. I gasped.
“Did you like that?” He asked again. I nodded, “yes sir.” “Good girl,” he said as he turned my around. “Bend over the desk.” I put my elbows on his large desk, my boobs hanging off and my ass in the air, only tights that ended at my thighs and my heels on. “That’s a good girl.” I felt in fingers rubbing my clit, dipping into my wet pussy. “Fuck you’re wet. Such a good little slut, isn’t that right?, he asked me, removing his hands. “Yes sir” I responded, dripping with anticipation. God I just wanted him to fuck me like a slut.
He slapped my ass, the pain making me moan. Suddenly I felt something hard and cold against my clit and I gasped. “Relax kitten, its a butt plug so you’re loose enough later.” I couldn’t believe it. He was gonna fuck my ass? I had only done anal a couple time, years ago in college. But I knew I couldn’t say no. I needed the money. He dipped the plug into my pussy, getting it all wet, and slid it across to my small asshole. “Relax” he told me, pushing it in a little. I moaned, gripping the desk. He pushed the rest of it in quickly and I gasped. I could feel the metal stretching out my tight hole. If this little thing felt like this, how would his huge cock feel?
Before I could think about it anymore, he pushed his dick into my pussy and I groaned, biting my lip. “That’s a good girl”, he said, slapping my ass again. I hadn’t ever been fucked by a dick this big, and I could feel it stretching my pussy. Suddenly he started moving out, then in. I dug my nails into his desk, moaning out in pleasure. Before I could adjust, he picked up the pace and I screamed out, pulling away from him. He grabbed my waist and pushed deeper into me, pounding even harder.
“What do you think you’re doing, you whore,? He asked, his balls slapping my clit with every thrust. He slapped my ass harder than before and I clamped my teeth together. “You want that raise, you’re my little whore. Got it?” He demanded again, slapping my burning ass cheeks again. “Yes sir,” I said, feeling my pussy being fucked, his whole dick plunging into it over and over. God his dick was huge. My eyes started to water, but he kept going, slamming his thick dick into my tight pussy over and over again.
“Oh fuck, you’re pussy is so fucking tight,” he said, gripping my waist harder. “You like my dick in you, huh, you like being fucked by my cock you slut?,” he asked, going even faster. I had to dig my nails into my hands to keep from passing out. It was too much. I could feel him filling me up to the brim with his penis. But what choice did I have? “Yes sir.”
He groaned. “Thats what I thought,” he responded, giving me one last thrust. I moaned out, feeling him hit so far in my vagina. Suddenly he pulled out and I started gasping for air. Why did I miss his cock in me when it hurt so much? He slapped my ass again. “God you’re dripping.” He said, running his hands across my clit. I moaned, shaking my ass in the air. I wanted more. I wanted more if his huge cock filling me up.
I felt pressure on the butt plug and suddenly, he started pulling it out. I clenched my asshole, but he pulled the plug out fast, leaving me no time to adjust. I sighed in relief, but it didn’t last long. He rubbed his dick across my wet pussy, getting all the moisture on my dick. He gripped my hip with one hand, and I felt the tip of his cock at my asshole. I braced myself, closing my eyes. Unlike my pussy, he slid his dick slowly into my ass. His tip passed my asshole with a little push and I groaned. God it hurt. He felt so big in my small hole. He braced himself by putting both hand on my ass, spreading my cheeks, and I braced my self against the desk.
Then he pushed himself in. All of his dick in my tight asshole. I screamed, not caring about my raise anymore and tried to move away from him, but his grip was too strong. “No, please no,” I begged, but he didn’t care. “Shut up slut, and take it.”
He pulled out a little and thrust all 10 inches into me again. I screamed, crying out in pain, but he started pounding away in my ass. “God your little asshole is so fucking tight,” he said, not letting me go. I could feel my asshole being stretched out, hurting so much as he slapped my asscheeks. “That’s right,” he said as I screamed out again. “Take my dick in your ass you whore.” Tears started creeping down my face, my whole bottom shaking. His balls hit my pussy with every thrust, and I cried out every time. He didn’t care. I agreed to this. My asshole was his, and I was just his little slut. “Tell me how much you like my dick in your ass,” he said, digging him fingers into my hips. “I like it a lot, sir.”
I felt his balls tighten when they hit my pussy. “Im gonna cum in your tight little asshole,” he said, speeding up. I couldn’t take it. I screamed out again as he thrust his whole length in my ass, his stomach pressing against my cheeks and his balls against my red pussy. I felt his hot cum shoot out of his dick and deeper into me. He moaned, giving me a few last sloppy thrusts before pulling out. My asshole immediately opened, and I could tell it was gaping. Hot cum started leaking out, running down my pussy and a little down my thighs. He gave me a slap on my asscheek and I whelped.
I heard a click and I bit my lip. He had taken a picture of me bent over his desk, my pussy and asshole destroyed and dripping with his hit cum. I couldn’t move, every small amount of effort to stand up shooting pain through my holes. I heard him get dressed. “Good job Katherine he said, picking up his briefcase. I couldn’t lift my head to face him. He chuckled and walked towards the door. “Clean yourself up and go home, this agreement is for a few weeks, i’ll see you tomorrow morning.”
I closed my eyes, cannot believing what I had gotten myself into. He opened the door, but before stepping out he said, “Oh, and Katherine, take the butt plug home, keep it in, I’m gonna fuck that ass again tomorrow.” He walked out and closed the door. My knees bucked and I fell to the ground, my asshole and pussy throbbing. I wiped my tears away. What the fuck did I agree to?