Becoming His Personal Assistant - Part 1 free porn video

This is a work of fiction, the forced sissification of Patrick, turning into eventual acceptance and appreciation. If this offends you, please read no further, as there will be explicit acts of forced sexual intercource and the like. My nylon legs are spread apart, pushed all the way up to my head and held in place, my limp clittie bouncing around in its cage, and my head is tilted backwards, as i let out girlie moans of pleasure while my pussy is being used for a stranger's pleasure. Above my head, a second stranger is getting warmed up, aroused by the sight of the sissy slut giving in. He orders me to give his huge swaying balls a tongue bath as he is stroking his cock, and i fill my mouth with his sack, before he even finishes his sentence. I didn't ask for any of this, but then again, i never really had a choice. I was a normal 22 year old just a year ago, a little scrawny looking perhaps, short, and didn't possess the most masculine features, but was often complimented by women on my looks. Cute and adorable was often used to describe me though, and other than some kissing and holding hands in my younger years, i had managed to never find myself a girl, not even for a single night. I suppose i should tell you that i suffer from mild anxiety and nervousness, which makes it nearly impossible for me to approach women. This of course means that all my sexual experiences happen from the safety of my home, usually looking at my monitor. My ordeal started shortly after landing my very first actual job at a law firm, though as an assistant to a few of the lawyers. I had left behind friends and family in pursuit of this chance, which meant moving to a new city, in the rougher part of town, and not having much of a social life. Working your way up though, requires starting at the bottom, and I felt this my very first week, where one of the senior attorneys, Roland, for some reason saw me as a doormat, and made me do rather humiliating things, like picking up his dry cleaning, and get him coffee. Roland was rather large, not overweight exactly, but just a big frame, chunky, muscular and tall. He was quite intimidating in the way he walked and talked, oozing confidence and ruthlessness, all good features for a lawyer i suppose. Essentially, he was everything i was not, and i felt like a mouse every time i was around him. "Hey Patricia, get over here," he called one day (my name is patrick). I hadn't seen him in the door, and jumped slightly, being startled, and rushed over perhaps a little too fast. He smirked briefly and threw a couple of folders to me. "i need you to take these files up two floors ASAP, and make sure you hand it over to Lisa at the desk." "Yes sir," i exclamined, and nearly ran to the door, folders tucked under my arm. "And be careful with those, this is an important client, and they are in the meeting right now." I felt great, this was the first real job Roland ever gave me, a clear sign of trust. I stepped into the elevator, pressed the floor button, and started humming a little, things were going great. As the elevator reaches the floor, the door opens, and i rush out, in such a hurry in fact, that i bump into a man about to enter. I drop one of the folders, and to my absolute horror, i watch it glide through the only crack it could possibly fit through, in the elevator door, and disappears. "Nooo!" i scream, and fall to the floor, trying to see if i can somehow see it, or reach or just anything, but it's useless. I start sweating, and look up at the man. "Sorry about that buddy, but can you get out of the elevator, i'm sort of in a rush." I stay in the elevator, push the button down again, and start practicing my speech to Roland. I sort of tiptoe into his office, head down, hands shaking, and clear my throat. "Well that was fast Patricia, good job," he said, before noticing the single folder in my hand "Sir.. uhm, i dropped one of the folders. It went through the crack in the door of the elevator, i'm so sorry!" Roland jumped out of his seat, his eyes wide with anger, and rushed over to me. "What the fuck did you just tell me?! do you have any idea who is sitting in that meeting room up there? Do you know how many signatures we had collected on those papers, you incompetent little ant. Are you telling me that i have to go up there now, and make excuses for your sorry little ass, and making the firm look like a fucking circus." "I'm so sorry sir, i.. i .. dont know what to say," i started mumbling in shock, as Roland grabbed my arm, and clamped down hard. It started hurting and i cowered a little as Roland towered over me "Please sir, it hurts..." i managed to say. I was now pretty much on the floor, and he finally stopped. I look up at him, with fear in my eyes, and meet his cold eyes as he looks down at me in disgust. "You're staying late tonight, and clear your calendar for the next two weeks, you'll be busy," he simply said as he left the office, and me on the floor. 5 days later, i was stuck alone at the office again, doing meaningless tasks as my punishment, looking at the clock that seemed to be running slower than ever. Roland had made it quite clear that my time at this firm could quickly come to an end, after such a big mistake, and i was being watched constantly. It was stressing me out beyond belief, and i was getting roughly 5 hours of sleep a night these last few days. In fact i hadn't even had time for my daily jerk off sessions at home, being too exhausted, and my tension was building up. Walking around these office ladies in their tight skirts all day, just to be left on my own each night, with only my thoughts, wasn't exactly helping. As i went into Rolands office to place some files on his desk, i saw his computer was still on, and was hit with a sudden urge to fire up his browser in the standard incognito mode that had become part of my jerk off ritual at home. I quickly looked around, even though i knew the entire floor of the building was empty, probably even the whole building. I ran over and locked the door regardless and hurried over to the desk again, and entered the URL for my favorite tube. The years of no sex, and a growing porn addiction, had pushed me towards the more kinky stuff, and i had eventually landed in the shemale section of the internet. It seemed to hit the spot for me, and for years i watched as these trans women had taken cock in just about every way, moaning in delight as their floppy little dicks was the center of attention. Watching them get pounded in a reverse cowgirl, or in doggystyle was by far my favorite, and i quickly found an interracial video, with a small asian shemale getting spitroasted by two big black cocks. I nearly ripped my pants in half trying to get them down to my ankles, and quickly grabbed my modest 4" dick as i started the video. The sound was turned up a little high, and her moaning filled the room, but i just didn't give a fuck, no one was here to listen. I buttoned up my shirt and started rubbing my nipples, while running my fingernails over my small ballsack. I started slowly jerking off, as she was now deepthroating, both cocks pistoning in a steady rhythm. I felt my climax build up, started to moan, and pinch my nipples. A few seconds later i blew my load over my chest, in the most fulfilling way, panting away, as the girl is on her knees accepting her reward with a smile, fuck i loved those horny little cock hungry girls. "Well well well, looks like this just changed for the better," i hear from behind me, as a pang of fear and shock jolts through my entire body. I spin around on the chair, while trying to pull up my pants, as i see Roland standing there with a smirk on his face, and a cellphone in his hand "Looks like i came just in time, and luckily i have keys to my office, didnt know i would need them tonight." I started stammering wildly, trying not to cry, while attempting a feeble apology, and speed dressing. "Stop what you're doing, get your pants back down," he said, as the camera was pointed at me. I dropped my pants again in defeat, as i started sobbing. "You like girly boys huh, thats funny. You arent much of a man yourself from what i can tell." He Laughed out loud as he stopped recording, and a little relief went through me. It was short lived though. "I think you may be working late, a whole lot longer than the two weeks i told you. See you tomorrow Patricia." I was panicking quite a bit at this point, as Roland just seemed to leave the office. Why didn't he fire me, and exactly how long would i be working late from now on.. And oh god, how much of that did he catch on his camera. I cleaned up best i could, and left the office for the night. I would probably get fired tomorrow, and i had basically just ruined my life. I come into the office the next day, with a look of defeat on my face. I feel like i'm waiting to be taken to the gallows, as i get my first cup of coffee, and smalltalk with some coworkers. I hadn't noticed Roland showing up yet, and was worried what that might mean. "Hey any of you know where Mr. Tanner is today," i ask, hoping some of the others know what Roland might be up to." "He has been in his office all morning Patrick, before most of us showed up i think. I guess he is working on something big." I start sweating immediately and gulp down my coffee in a hurry. I don't want to face Roland right now, but i have to know what my fate is. I leave the others and head for his office. I knock quietly, and after a few moments, i'm called in. "Ah Patricia, the office masturbator, lock the door behind you," he said as i enter. With a red face, i do as i'm told. "Sit down, kick up your feet, feel right at home. You sure did last night," he said with a sadistic grin. "Please sir, i'm so sorry, it will never happen again! I'll do anything to get out of this, i swear, it was just a mistake." Roland put up a hand silencing me. "Well i dont think you get out of this one sweetie, in fact, your decisions in the next few minutes, will greatly determine the outcome of the rest of your life as i see it. You see, i now have everything i need to make sure you never work at a law firm, another day in your life." My jaw dropped for a second, as i start to stammer again. "Shut up if you know what's good for you, and listen. I have a full video of you spanking it to some pretty kinky stuff, that i'm sure you dont want anyone to see. On top of that, your screw up last week, is more than enough to make sure that you would be lucky to work in this town at all, other than flipping burgers perhaps. So this is what i propose. You become my personal assistant from now on, and do exactly as i say, and you may just have a future in this firm." I couldn't believe my luck, and was so greatful to Roland for at least giving me another chance. And personal assistent for a senior attorney, is actually considered quite a step up. Roland slides some papers over to me, my new job description and title. "Sign this if you accept.. And i do strongly suggest that you accept this Patricia," Roland said with a calm voice. I start flipping through the many pages of the contract, quite a few more pages than i would expect for a simple PA job. Roland starts tapping his fingers on the desk as i read, starring with his hard cold eyes. "Dont think too long on this Patricia, the offer might go away." I grab a pen, flip to the last page, noticing the name at the bottom says Patricia instead of Patrick, Roland of course already signed his part. I sign it and slump back in the chair. "Thank you sir, you dont know what this means to me, i know i can do better, and i wont let you down," i say, but again he stops me. Roland slides his chair back from his desk, starts to unbutton his pants, and in a commanding voice says "Get over here Patricia, and drop to your knees sweetie, your new job is about to begin." I stare in disbelief, feel my mouth dry up, hands start to shake again, as i stand up, and start moving to the door. "Sir... i dont know what this is, but i'm not into that at all," i stammer, but Roland just chuckles. "Get on your knees Patricia and crawl over to me, NOW! You should really read something before you sign it, because you basically just signed away your life. Sure its cleverly hidden in lawyer mumbo jumbo, but TRUST me Patricia, you do not want to test me right now. I will rip away everything you ever fucking hoped for, with just this little slip of paper," he says as he holds up the rather thick stack of papers i just singed. "Please sir, i..." "NOW," he yells, and in shock i fall to my knees, my mind racing as i feel the tears forming in my eyes. "Crawl over here, do as i say Patricia," he says, now calmly. I start crawling, i hear myself sobbing slightly, as i go around the desk and stop at his feet. "Take off your clothes Patricia, ALL of it." I undress slowly, trying to think of a way out of this. I know it isnt legal, but i dont fully know what is in those papers. And with the other stuff he has on me, the video and my office screw up, i'm simply too afraid to object right now. I was never any good at confrontation, and was easily bullied around. I was now being bullied around by the scariest man i could imagine, and as i reach my boxers i stop for just one second, look up at Roland, who has a very sturdy look in his eyes, and with an exhale of defeat, i pull off my boxers, now completely naked at the feet of my boss. "Good girl, i knew you would see reason. You really dont have much of a choice in this, and it's not as bad as you might think. Now pull down my pants, get my cock out, you little slut." I start seeing spots as i move slightly closer to him, i can hear my own pulse in my ears, and i have no control over my breathing, i slide the pants down, only to realize that he has no boxers or briefs on. His semi erect cock starts growing a little, and looks absolutely massive. Just like a porn cock, too big to be real, and yet just right there. "Make sure my balls are free as well, get the pants all the way down," he says as he spreads his legs a little. I pull the pants down all the way and off his legs, and he spreads his legs more, giving me a full view of the intimidating size of his cock, and now his balls that are equally as big. I look up at him, with a questioning expression on my face, Hoping this has all just been a prank. "Cup the balls sweetie, feel the weight of those things, you'll get to know them quite well in the future. Dont hold back now," he says, now with a look of pure lust and amusement. I shakily put my right hand towards him, and then start sobbing. I stop halfway there, begging him with my eyes not to do this, but it has the opposite effect. He forcefully grabs my hand and yanks it towards his balls, and i now have more than a handful of the biggest, warmest balls i have ever seen, in my hand. I freeze completely, trying to imagine this is happening to someone else. "Now grab the cock sweetie, dont be scared of it. If you treat it right, it can make you feel sooo good." I dont move, incapable of even responding, as i sit there cupping his balls. A few more seconds pass, and he suddenly jumps out of the chair, slaps me across the face, and before my head snaps back naturally, he grabs my hair, and smashes my face into his groin. "Dont you ever fucking disobey me again, you hear?! I own you now slut, and this cock is your new master. Now fucking get to know it, because it will be your main focus for a LONG fucking time." He grinds my face on his balls, slaps the dick around on my face, and then forcefully pulls back my hair, pointing my face upwards "open your fucking mouth, and stick out your tongue, NOW!" I quickly obey, sticking out my tongue as far as i can, He places his balls on my tongue and start to move it around. I cant believe this is happening to me, the humilitation of another mans cock in my face, as he gives himself a tonguebath using my mouth. Suddenly he stops, looks down, and commands me to start licking. In my defeated state, physically and mentally overpowered, i simply comply. I start lapping at his ballsack like a kitten, as he moves his large cock to rest on my forehead, i hear a grumble of satisfaction, as i move around. The smell and taste of him is almost intoxicating, and the texture of his rippled yet soft balls, honestly feels quite nice. I stop for a second in sheer horror, that i just realized how quickly i accepted the abuse from my boss. And not only that, i am finding positive things while being used by another man. Why must i always try so hard to please others, i should be freaking out right now! My train of thought is disrupted as quickly as it started, as he pulls back on my hair again, and commands me to stick out my tongue "Learn to love this taste slut, love it like your fucking life depends on it, because i am going to make it your new favorite meal." He has his cock in his hands pointing straight at my mouth, and i can see a large drop of precum almost hanging off it. He moves it closer to my mouth, as he makes are sort of milking motion, starting all the way from his balls, and i see a large glob jet out of his cock, as he places it on my tongue. My eyes widen as i taste precum and cock for the first time, and again am given little time to absorb this new feeling, before he forces the head of his cock inside my mouth. My arms are now hanging limply down my side, sitting on my knees, as he grabs my head with both hands and starts facefucking me. I have trouble with my breathing, and the sputtering of saliva and precum, as he forces himself deeper down my throat. It's painful and i am constantly gagging, and yet i have time to be amazed at how soft his cock really is, especially his cockhead. Before i feel another pang of regret over how easy i am accepting this situation, he pulls his cock from my mouth, leaving only the embarassing sound of my suction. Apparently i was unknowingly helping him along. "Good girl, very good," he says as he starts jerking his cock in front of my face. "You are already working on your technique i see. You need to watch your teeth a little more, and i need a lot more suction from you, but not a bad start. I'll break that throat of yours in no time, but for now, stick out your tongue and open your mouth as wide as possible." I knew what was coming next. I have seen plenty of porn to know exactly what this is, yet just like a bimbo, i stare up at him, accepting my fate, as he grunts heavily, his legs tensing, cock throbbing, and the first blast of his cum hits my face. The next 3-4 blasts, shoot right into my mouth, as he moves closer, ensuring i get it all, and he eases the cock back into my mouth with only a mild pressure on the back of my head. "Clean up the mess darling, i don't want any traces of my cum anywhere. Use my cock to scrape it off your face if you have to, and fondle the balls with your hands while youre working. I want to make sure you get all you can eat sweetie." He sits back in his chair, holding my head close as he does so, his cock never leaving my mouth, and simply sits back with a content look on his face. I slowly lick and suck his cock, knowing how sensitive it can be after you come, slightly disgusted at how considerate i am being after this treatment of his. I do the same motion of milking his cock, starting from his balls, to make sure i get everything, and it amounts to another big load of cum. Thank god i didn't miss that, he would have been so angry. I start rubbing his cock all over my face, trying to scoop up the the remaining cum on my face, but end up smearing it more than anything. It is taking a long time cleaning up, but i'm being very thorough and systematic. I guess i'm coping with it by simply focusing on the task i have, and getting it done as fast and effeciently as possible. His cock has gone more or less limp now, but is still much bigger than mine could ever be even at its biggest and most throbbing. I notice that my cock is in fact slightly hard, and a little precum is leaking out. Roland sees it as well. "Ok i think my cock is clean now slut, but make sure to scoop up your on precum, i dont want any to dribble on the floor." i instantly comply, and as i run a finger over the tip of my cock, i feel a small jolt of pleasure. I lower my head in humiliation and shame over my own bodys response as i lick my finger. Now that the job is done, i am catapulted back to reality, and what i just allowed Roland to do. And how easy it had been for him. He opens a drawer in his desk, pulls out a thin pink leather strap and hands it to me. "Its a collar, that i would like to you to put it on now sweetie, you've earned it." The collar has a heart shaped tag with the inscription "Cocksucking Cumslut," on it, and i feel the tears forming in the corner of my eyes again. Roland sort of pets my head, with a "there there," feel to it, and orders me to put it on. As i lock it in place, he attaches a small heart shaped padlock, and i slump even further, as i realize this thing isn't coming off anytime soon. "You will wear that at all times now, its up to you how you hide it, or if you want, you can just let people see it. At the office, you will of course wear a shirt and tie, and this WILL be kept a secret for work. Now, before you get dressed, i'm gonna have to ask you to lay over my lap. There is the little matter of your disobedience." I know what's about to happen, but in the scale of things, i suppose i just went through something much worse. I place myself over his lap, my butt pointing straight up at him, and await his punishment. Rolands hands feel soft and hard at the same time, as he slowly rubs each buttcheek. The motion almost tender, as he squeezes, his thumb getting a little too close to my butthole than i would like, as he grabs more firmly. I try to look up, to see whats going on, but he barks an order to keep my head down, as he keeps squeezing. Then suddenly a large smack seems to almost echo through the small office, i'm not even sure how thats possible. And almost with a delay, i realize how hard he just slapped my buttcheek. I gasp and inhale sharply, now feeling the tears again, as another one lands on the other cheek. "Start counting, and if you miss a count, i start all over again," he says as the third hit lands. "THREE," i exclaim in pain as i begin sob, the sting almost unbearable "FOUR," the tears now running down my cheeks, an incredible warmth spreading over my butt "FIVE," i say in a cracked voice, the pain still just a strong, but my acceptance helping me cope "SIX," i say in a lower voice now, worried that someone might hear me He continues to slap another 15 times, each slap just as hard as the last one, and my ass feels like it's on fire, almost like i feel heat radiating from it. When he is done, he slowly begins to rub and squeeze again, and while still painful, it also feels amazing, almost like a reward. "Good girl, you handled that very well. It's important you understand, that i will not accept defiance from you at all, and i have many ways to punish. Now i dont enjoy harming you, so please make sure to not give me a reason in the future. Also, i expect only two sentences out of you, 'Yes sir,' and 'Thank you sir,' got it? Anything else, and i'll ask you first." There was a moments pause, before i realized what he expected, and squeeked out a small, "Yes sir." "Good, you are learning quickly. Now do you see that large crate next to my desk," he asks as he slowly turns his chair, with me still on his lap, hand resting on my buttcheek. I didnt notice the crate before, but then again, i was kind of busy. "Open the lid and see what i have for you in there. Lots of fun little toys, but we will get to that." I slowly open the lid, and it's filled with a lot of smaller boxes, some shoeboxes, some bags labelled Victorias secret, and other labels i wasnt familiar with. And underneath i thought i could see maybe.. A dildo or something, more than one even, but too hard to see for all the boxes and stuff. My eyes locked in on one specific thing at the very top of one of the boxes. Lubricant, a medium sized buttplug, and what appears to be little frilly panties, open in the back. My heart started pounding again as i began to understand the magnitude of this whole thing. He put together this crate just yesterday, and its filled with a bunch of things that i didn't even want to think about right now. I realized that i truly had no idea where this was all going. He slowly pats my butt, which sends a jolt of panic through me, expecting another slap. He chuckles as he caresses my ass "Take out the lube, buttplug and panties, and put them on the desk will you." I do as told naturally, too weak to put up any resistance against what is about to happen, too ashamed of what has already happened, and with the small hope that i just have to endure a little, to escape this horrible ordeal. "Spread your buttcheeks for me darling, and show me that sweet little pussy of yours, and be quick about it." i snap both arms around and pull my buttcheeks apart, much to Rolands amusement, the last punishment still fresh in my mind, and on my ass. My cheeks are still sore from the spanking, and i can feel the cool air on my now exposed butthole. Out of the corner of my eye, i see Roland reaching for the lube, and my breathing intensifies. I look straight down at the floor, hands still firmly pulling apart my cheeks, and prepare for whatever is about to happen. I felt something cold land on my hole, which sent shiver down my whole body, and after a moment, i feel the tip of a finger start to slowly spread it around. My body quickly heats it up, as every nerve ending in my opening is sending signals to my brain. To my absolute horror, i feel my small cock stiffen again, right into Roland legs "Interesting Patricia, very interesting," he says as his finger keeps circling my entrance, which is now twitching and tensing beyond my control. I feel him position his thumb as if ringing a doorbell, and he starts pushing gently. At first he is met with resistance, but keeps a firm constant pressure on my hole "Lets see if we can loosen up your pussy sweetie, it sure is wet now. Come on, open up for daddy, let me in. I know you'll like it. Thats it, relax your muscles, just let it happen." I can feel my resistance lessening, and his thumb begin to disappear, as my mouth is open and i am gasping even though i dont need air. "Fucking hell, your pussy is so tight," each mention of my pussy sent a jolt through my little cock, that was digging into his leg, and with a whimper i felt myself opening up, and his thumb plunged deep into me. The whimper instantly turned into a moan, that sounded entirely too girly even for me, and he slowly started working his thumb in and out. A small amount of drool left my mouth as he started to loosen me up, sending sensations through my body i had never felt. I was involuntarily grinding myself against his leg, my eyes closed, and my body shivering, not from cold, but from something i had never felt before. He was massaging something inside me, that was literally turning me crazy. Suddenly a slap hit my buttcheek, from his other hand "Dont fucking cum, stop moving around so much, or i'll give you something to cry about." The slap made me tense up instantly, and my pussy gripped his thumb like it would never let go "God, you are so fucking tight, almost seems like a shame to break you in, but oh well," he said as he continued to loosen me up, rotating and pulling with his thumb. I relaxed again, and he regained full access to my pussy. He quickly repositioned my small cock so it was pointing backwards, resting on his leg, in full view, as he chuckled "Look at that adorable little clit of yours, so eager to be rubbed by master huh. Well maybe if you are a good girl, we can look into that later." He pulled his thumb out with entirely too much speed for my liking, and reached for the buttplug. He coated it with a little lube, and put it against my entrance. Even with his preparation, this wouldn't go easily into my pussy, i could tell. I tensed up and bit my lip, in anticipation. But he just held it there for a while, applying constant pressure, while slowly stroking my back "Easy now sweetie, let it happen, just let it happen. Exhale slowly and open yourself up. Take it and afterwards i promise you will feel so proud." I tried controlling my breath, and relaxing my pussy. My cock had now gone completely limp again, and despite it feeling much too tight, i could now feel the slightly bent buttplug begin to slide into me. I moaned again, with a mixture of pain, pleasure and disbelief, and suddenly it popped right in, locking itself in place as my pussy once again grabbed a hold of its intruder. The second it was in, Roland stopped stroking my back, and almost pushed me of his lap, and i landed on the floor. "Now put these black panties on, and present yourself to me slut." I was still gasping for air, and now there was a buttplug constantly putting pressure on my pussy, and giving me weird sensations over my entire body. I tried standing, but my legs were quite wobbly, and started shaking uncontrollably as i did. I gathered myself, and stood up straight. I picked up the panties, hardly any fabric to them at all. Once i figured out which way to turn them, i bent down and stepped into them. Without even noticing, i wiggled my hips as i pulled them up, like ive seen women do, and instantly felt my face get red. "You're a natural sweetie, so very delicate and feminine, turn around for me." I started turning, while covering my face in embarassment. I was on display now, and i couldnt hide myself in a task, or get distracted by eager hands. Roland was just looking at me, and i could feel the panties tight to my body, the buttplug grinding my pussy with each movement. I turned all the way around, and then Roland made a circling motion with his finger. "Turn back around sweetie and spread your cheeks, let me see that sweet little pussy getting a workout." I did as told, turning my exposed ass his way, and gently pulled my cheeks apart again. The cool air once again hit me, and i could feel the buttplug more than ever. I could hear sounds of approval from behind, as i realized i was now starring into a full lenght mirror. I saw myself standing there, with a pink little collar, and completely naked except for the adorable little panties covering my clit, as Roland calls it. I felt another jolt of pleasure and my clit started hardening again, guilt and pleasure rolling over me. "Hmm we will have to do something about that clit of yours Patricia, but for now i think you need to get back to work. Put your clothes back on, and go about your day as if nothing changed. When everyone is about to leave, i expect you to show up at my office and get ready for your overtime. It will be one interesting evening, dont you think?" "Yes sir..." End of part 1 If you made it this far, PLEASE PLEASE PLEASE leave me a comment on [email protected] with anything you can think of, pics, comments etc.