The Bosss Daughter 1

By Rayne416

All characters in this story are 18 or older, and the author does not in any way condone non-consensual sex. This story is fiction and contains: rough anal, pain, humiliation and degradation, oral and nonconsent/reluctance; if you don’t like these themes, please do not read or rate it. This work is purely fantasy, and any resemblance to actual persons, living or dead, or actual events is purely coincidental.

My reverie was interrupted by a rap at my office door, quickly followed by my boss, Pierre. I waved him in with one hand as I pretended to look up from my monitor.

“Hey Marcus, do you have a minute to talk about this quarters’ numbers now that you’re back?” he asked, his pudgy body overflowing from his suit. Pierre was VP of our division, and while he was a nice enough guy, he was a shitty VP. The company was doing very well this year because of the long hours myself and the other directors were putting in, and this waste of space got the boards’ praise. Sure, it pissed us off, but it was expected and you didn’t get to position I sat in without some political sacrifices. I couldn’t complain too much though: nice corner office with a view, a competent assistant, and a fat paycheck.

“Of course, Pierre,” I said enthusiastically, flipping one of my monitors around to face him. He shuffled over to one of the chairs in front of my large black desk and settled into it while trying to make sense of the graphs in front of him. I began to cycle through the charts and numbers I maintained, explaining shit he had long lost sight of, my other hand keeping a solid grip on his daughter’s head under the desk.

Lily was attempting to keep my cock lodged in her throat and not make too much noise around my thick cock as her dad struggled to pretend he understood what was in front of him. She only had about five inches of my shaft in her, but was successful thus far in not tipping off her dad.

Last weekend I had gone to Coachella with some friends from college, and happened to stumble into Pierre’s daughter there. Actually, she had stumbled into me; I had realized during our interaction that she was flying high as a kite on some version of Ecstasy. After some chitchat, she appeared nervous that I was aware of her drugged-out state, but my chill mannerisms and conversation quickly put her at ease.

We’d met a few times before since she liked to come by work and see her father, particularly when she needed more shopping money. She was your typical “daddy’s girl”: drove a new BMW, borderline hooker attire, bleach blonde hair and a flirtatious personality. She was going back to college this fall, and I was sure going to miss her perky tits occasionally skipping past my office door.

In her inebriated state she had flirted with me, and I had thankfully documented our interaction on my phone. Considering her state, I had taken her back to my hotel room to come down, listening to music and just chatting. She tried to put the moves on me multiple times, but I wasn’t about to fuck the stoned-out daughter of my boss, so eventually she passed out on my couch.

On the other hand, I had no problem fucking her brains out when she was sober, which I did the following day. What started as polite conversation over room service breakfast quickly turned to horror as I dredged up her antics from the night before on my phone. That turned into embarrassment, which I quickly dismissed by pulling my cock out and making my own intentions clear. The shock on her face forever burned in my mind as she drank in the sight of my dangling 9” cock, her mouth still agape as I pushed her to her knees. Her awe quickly turned into a struggle as I forcibly wedged more and more of my meat down her inexperienced throat. It became apparent that she had never been forced to deepthroat, so the morning turned into a tutoring session that she failed at repeatedly. Tears mixed with saliva on her cute face as she tried to unlearn her gag reflex again and again. It was only when I dangled her head off the side of the bed and pinned her hands with my own that I was ever able to seat myself fully within her blossoming throat.

When I felt as though she had learned enough for the day, I then turned to broadening another of her horizons... and orifices.

I’m so horny

, she had said, wiggling her butt at me and sensually trying to mount me once I’d released her mouth from my hips.

I want you to fuck me so hard with that huge cock!

Clearly, she’d never done anal before either, based on the protests and sobbing when my tip jarred her sphincter open. It took me threatening to show her drugged up episode to her father for her to lay still enough for me to penetrate her again. And by still, I mean trembling facedown on the bed, her hands pinned to her sides by mine as I forced myself deeper into her. Her crying and moaning into the sheets kept my cock as hard as granite as I slowly pushed inch after inch within her.

I can’t take it

, she had wailed,

your cock is too big for me!

Another subject she would relearn that day. She didn’t know how adaptable she was yet, but I did take pity on her and only filled her asshole with about half my cock that day. The perpetual crying might have brought housekeeping and she still had a long and arduous future ahead of herself at my hands. As the fight slowly drained out of her and I was able to mold her into different penetrable positions, she learned to find the pleasure in the friction and pressure in her nether region, and my occasionally rough ministrations on her clit accelerated her orgasm.

I began to notice with each new slap, choke, or fist of hair pulled, her breathing intensified and her face flushed with involuntary lust. By the time I had her in a full nelson on my chest, hands locked around her tiny throat rocking her ass up and down on my spear, I knew she couldn’t contain herself anymore. Strained gasping accompanied full body convulsions as she coped with the immense flood of sensations from her first anal orgasm that threatened to never end by my sustained penetrations. I could feel her slobber run down my arms as her petite body twitched on top of mine, the sawing motion of my hips keeping her ass on fire and her mind in an unintelligible state. When I finally released her from the full nelson, she lay on the bed sobbing quietly as I dragged my cock out of her asshole and placed it in her unresponsive mouth. Several more involuntary orgasms followed as I rotated between her two orifices, keeping my cock hard and her asshole sore.

Please cum

, she had moaned weakly as I returned to her gaping asshole.

Where do you want me to cum?

I had asked as I rhythmically fucked her asshole, pinning her legs to her chest.

In my ass, baby,

she tried to moan seductively as she looked up at me, her septum piercing accenting her pale face and dark eyes.

Wrong answer,

I had growled, punctuating it with a deeper stab to her colon than usual. Her scream was abruptly cut off as I roughly grabbed her by the throat and pulled her off the bed to her knees. Nesting my cock deep into her throat, I grabbed a large handful of her bleached hair and pinched her nose shut. As her body contorted around on the floor beneath me and she fought against my strong grip, I verbally cemented our relationship.

You’re gonna take my load on that cute little face of yours, you little anal whore,

I had growled into her ear.

A good anal slave takes it in the face, doesn’t she?

Whether or not she agreed or just wanted to breath, she nodded energetically and I released her from her muzzle. Gasping, her beautiful face hung from my grip as I lined up my cock and plastered her face with cum. The first stream covered her nose and cheek, and I adjusted for the next blast to get her in the eye. Laughing, I showered the rest of her face with my remaining cum as she struggled to remain composed. When I was satisfied with my handiwork, I placed my deflated meat back into her mouth to clean off.

“-and these are good for us? This is better than last year?” Pierre broke through my recollection as he scanned the screen.

“Oh yeah! Even with the turbulent semiconductor market this year, we were able to sustain growth not only in profit, but also employee numbers,” I gestured at the presentation. I readjusted in my seat and tried to force Lily to accommodate more than the front half of my cock. I didn’t have to worry about the threat of her making noise since I think she was more concerned with him finding out. Occasionally I would clear my throat or have my feet shuffle to cover a bit of silence so she could continue to quietly gasp around my cock. She had really improved her abilities, breathing around my monster cock and suppressing her gag reflex to deepthroat even in this kneeling position. Regardless, I kept a vicelike grip on her skull to ensure there was no slack in her throat.

I scanned Pierre’s face and watched him try to put together something intelligent. You could always tell when he thought he needed to say something and was struggling by the way his bald patch started to sweat.

“Rest assured, I think your new policies this year have really solidified our foundation in these markets and secured our future outlook,” I blathered gracefully, gesturing to the last few slides.

“Good... uh, that’s great!” he smiled back and stood up while giving me a thumbs up. “Good talk!”

“You got it, boss!” I grinned back as Lily sputtered around the base of my cock. I had finally succeeded in lodging the entire length down her throat, and she was beginning to wiggle in discomfort between her father and I. The tears I felt hitting my lap made my cock harder in her throat and filled any remaining room in her gullet. As he walked away, I began to drive her head back and forth under the desk while thrusting my hips to meet her mouth. Retching sounds emanated quietly from my desk and I cleared my throat again to mask the noise.

As Pierre reached my door, he turned around as something came to him.

“Oh yeah, have you seen Lily? Mrs. Davis said she came by today...”

“Um, I think she went to the café, she sounded awfully hungry!” I said while pretending to recall something, “Oh, can you shut the door, I have a lot of work to do this afternoon.”

“Yeah, no problem,” he obeyed, and left his daughter to my cruel hunger.

Hitting the electronic lock on my desk, I slowly rolled my chair back and was greeted by a tear and mascara streaked face.

“Good girl,” I said kindly as she crawled out from under the desk, trying to catch up to my receding cock. Her butt wiggled beneath a pleated blue skirt, her tight white top matching the white stockings she wore with heels. A black leather choker contrasted her bleach blonde hair, which was now tied up in a tight bun on her head. It really did wonders to keep her hair out of her face when she impaled herself on my cock, and it served as a great handle for that fuckhole.

“Please can I have your cock in my pussy today?” she pleaded with her large glossy eyes and pouty lips. Her face winced as my hand struck her cheek hard, a ritual she had gotten used to in our freshly carnal relationship. Growling, I grabbed her by the bun on top of her head and dragged her body up and over so her body was laying across my knees.

“Anal slaves get fucked where?” I twisted her head so I could whisper in her ear as my other hand snaked between the thong dividing her asscheeks. Dragging my fingers along her slit roughly, I covered my fingers in copious amounts of juices.

“In the ass...” she whimpered pathetically before sucking off the slick fingers I shoved in her mouth.

“Exactly,” I affirmed, “And if you weren’t such an anal whore you wouldn’t be so fucking wet now, would you?”

“Mmmmhmmmm,” she murmured around my fingers as I roughly explored the inside of her mouth with my fingers, trying to fit more of my hand in her.

“Good little anal whore,” I murmured back to her before removing the hand from her mouth, letting her gasp for a moment before striking her with the same hand on her exposed butt.

She yelped playfully and her feet wiggled in the air as I rained moderate strikes down on asscheeks. As the onslaught of strikes began to wear on her butt, the yelping increased in pitch and I saw tears start to pool in her eyes again. Releasing her hair, I instead shoved four fingers into her mouth to mute her, causing her to gag as I held her there. As I continued to rain strikes down on her ever-reddening butt, my thumb on her chin and fingers in her mouth kept her immobile. Tears began to flow freely as her gag reflex and pain threshold fought for a reprieve. Finally convinced she wasn’t thinking of anything else other than survival, I released her from her prison and stood up, dragging her by her hair around my desk. Placing the chair her dad was just sitting in against my desk, I hoisted her onto it and bent her over the back of it. Her hands resting on my desk, I stood behind her and drank in the sight of her firm butt, black thong askew.

“Don’t you move a fucking inch,” I growled in her ear as I held her throat with one hand, and slid a slick finger into her asshole with the other.

“Unnnhhh,” she breathed out, but stayed put as I dropped another finger in her anus, loosening it for the upcoming sodomy.

“Huuurrrrmmmmk!” she moaned through her constricted windpipe as more fingers entered her, only lubricated with the saliva from her throat.

“If you weren’t so fucking slick right now, I would probably quit doing this to you, you know?” I chided her as I re-lubricated my fingers with the juices flowing from her exposed pussy.

Her face hung in defeat as her body continued to betray her brain, and my iron grip on her neck reminded her there was no release from her predicament.

“Now remember, when I stick my whole cock in you, you don’t want to alert your dad,” I reminded her, “How unfortunate would it be for him to come over and learn his daughter is a certified anal whore?”

She groaned quietly and nodded her head as I removed my fingers and stepped up behind her. She moaned pretty loud in the past, but I intended to use the last few inches of my cock that had never seen her rectum, and I knew it was not going to be pretty.

“Spread ‘em,” I said gruffly while spitting onto my dick and aiming it. Obediently, she reached back, laying her head on my desk and peeled her cheeks back, revealing a recently stretched but still snug asshole. Placing my head at her entrance, I shoved it in roughly until the head was embedded. She gurgled in an attempt to quiet her reaction, so I reached an arm over her head and again shoved my fingers in her mouth, covering her face. Lifting her head up, I kept an iron grip on her skull through her mouth, while pushing forward with my hips. Her hands left her ass and thrashed on the desk in front of her as I started my descent into her. Head tilted back hard, her cries became distorted but there was no opposition against my anal invasion. Her petite body perched on the chair completely within my reach; there was no part of her nubile body I couldn’t touch, couldn’t pinch or slap while sodomizing her. I owned her body completely.

As I drove more of my cock into her, muffled sobbing began to emanate around my hand, and I felt saliva running out of her agape mouth.

“Good little anal whore,” I reminded her sweetly as I pinched a nipple with free hand. I assumed she barely noticed it through the burning in her rear. My cockhead was on fire as it pushed through her rectum in an effort to straighten her back passage out. Even after our weekend at Coachella transforming her into an anal slave, her canal was still so fucking tight. She was starting to shift her knees, trying to slow down my invasion as I sought to bury the latter half of my cock in her. Every time she shifted away from me, her spine would compress into her skull and she was forced to settle back into me. I could feel her entire body trembling beneath me, the painful position combined with what I assumed to be cramping or a tearing sensation in her abdomen. Not wanting to distract her from the painal, I released her skull from my hand, and she wept into the desk.

“You’re not still wet are you, Lily?” I questioned cruelly, already knowing the answer. It didn’t matter how much she had fought the sensations back in the hotel room, how much she’d tried to convince herself she was being anally blackmailed: she came like a geyser when I abused her insides and she still didn’t know why.

“I, I ... I don’t know,” she gasped in between hyperventilating sobs right before I gripped her hips and abruptly shoved the last three inches into her, my balls slapping her slick pussy.

“AiiiiiiGH!!!!!!,” she screamed, her back arching and head flying into the air. Seizing the opportunity, I reached around and clamped my hand over her mouth, muffling her wailing.

“Shhhh, shhhh, shhhhhhhhh,” I hummed quietly into her ear, leaning over her as I flexed my hips back and forth deep inside her, “Don’t want daddy to hear, do you?”

Her hands scrabbled around on the desk beneath me, clawing at the rich wood, trying to find purchase and adjust her position as I seated myself deep in her. Warm tears streamed over my hand as she groaned into my hand. Her ass was clenching, trying to reject the invader, but it was just increasing the friction that was laying waste to her insides.

“It’s gonna get a bit worst before it gets better, slut,” I muttered into her ear as I placed one foot onto the chair and reached my other hand to grip her choker roughly. With my center of gravity directly over her butt now, I pistoned my cock in and out of her, barely silencing the sobs and grunts emanating from her other fuckhole. With a strong grip on her mouth and neck controlling her entire body, I pulled my cock out until I could feel her sphincter clutch only my bulbous tip before pushing it back in one smooth motion. Well, my hips moved smoothly into her, but her body shuddered throughout the penetration, only stopping once my entire length lay in her. Her trembling and struggling was just making it harder for her, and my cock even harder. Glancing down at her small muscular back, I tried to imagine how far up her body my cockhead had made it. Her cute butt was grotesquely split wide by my shaft, veins bulging through the taut muscle that used to be a virgin asshole.

“C’mon babe, I know you like this shit. Tell me how hard you’re gonna cum, you little butt-slut!” I growled into her ear as I continued the anal assault with a consistent rhythm.

Her groan affirmed the inevitable, so I tightened my grip on her throat and increased my pace. Fresh hot tears hit my hand over her mouth as I felt the sounds of the beginning of an orgasm start in her chest and try to escape her throat.

“You like that rough ass fucking, don’t you?” I jeered while nibbling her ear, removing my hand from her mouth, letting her know a response was expected.

“Haaaahhh!!!” she screamed into my office, before realizing she needed to keep it down.

“I... No! I don’t... like this!” she stammered out, even as she trembled below me from impending orgasm.

“It huuuuurrrts,” she sobbed miserably as she tried to convince me that she wasn’t just an anal fucktoy, but a girl worth fucking in her pussy like past boyfriends had.

“Oh, you want me to stop?” I said, pausing my thrusts but keeping my cock lodged in her. Just enough to make her feel full, but no more pain to curb the anal orgasm that’d been building in her loins. My hands snaked down to hers on the desk and interlaced our fingers gently, but firm enough to ensure she couldn’t escape. It was sensual, our bodies and fingers intertwined like lovers except that the position maintained control of her petite body, ensuring she knew her freedom and pleasure was dictated by me alone. The huge log in her asshole also changed the nature of it.