Sissy Slut Ally

I primped and preened as I tried on the new tight black dress that you bought me, happy that you would finally show me the attention that I had been yearning for years but too afraid to ask for.  You told me that tonight you had a surprise for me and that you’d treat me exactly as I deserved to be treated.

My obsession with you started the first day you appeared at work, so handsome, bold, and so much younger than me.  I was a much different person then, still pretending that I wasn’t interested you… threatened by your mere presence.  I even made you call me “sir” to assert my authority over you as a way to put you in your place.  I could tell that didn’t sit right with you, but that made me believe that I had gotten under your skin.  I’d often find you skulking in my office, and I had my suspicions that you were stealing my work or trying to find dirt on me as I’d often catch you at my desk doing something to my computer, but I could never prove that anything was amiss and couldn’t get HR to fire you.

It was soon after that I started noticing you in a different light.  My jealousy soon became attraction, as I started noticing your handsome features that far surpassed mine.  I was threatened by your strong, masculine presence, your hard body, even your cologne was intoxicating every time you crept behind me while I was working at my desk and leaned in to tell me to pay special attention to the Very Important spreadsheet that you insisted that I open in front of you.

I stayed at work later and later, obsessed with trying to understand the spreadsheet that you had pointed out to me, but no matter how much I tried to look at the numbers, I found that my mind could never focus and that I would only return to my senses well into the night.

As my work suffered, you began to impress the CEO with your work and it wasn’t long until you became the lead on all of my former projects.  You didn’t mind having to carry my workload though, as you insisted that I focus all my attention on the Very Important spreadsheet instead because it was crucial that I understood what the numbers were trying to tell me.

Rather than feel threatened by your promotion or the fact that you were now effectively my boss, I felt in awe of how intelligent you were and the fact that you let a middling failure of a man continue to work for you when you could have anyone on your team.   The fact that you were giving me so much extra attention felt like a privilege to me, even if I was too stupid to figure out what was so special about the spreadsheet I spent so much time examining.

One day I found myself in the bathroom as you entered and almost deliberately stood at the stall next to me.  You didn’t seem to have a care in the world as you unzipped your fly and whipped out your monster of a cock to take a piss.  I think you caught me staring at your enormous member wide-eyed and slack-jawed, because you sneered at me and asked me if I was impressed.  I blushed furiously and turned my head away from him to look down at my own penis which seemed microscopic by comparison.

I was too afraid to move, so I stood at the stall even though I was long done, hoping that you’d leave.  After what seemed like an eternity of hearing your piss hit the porcelain of the urinal, you finally finished up and walked past me, slapping my ass as you went to the sink to wash your hands and left.

I started to panic – something about this felt so wrong and it seemed like I should tell someone!  But when I cleaned up myself and began to head back to my desk to make a complaint, I felt my phone buzz as I received a new message.  I pulled it out and opened the message and what I saw definitely should have made me angry.

It was a picture of a giant cock with a message: “Now you can take a look at my cock any time you want, you little faggot.”

I wanted to delete it in disgust, or report it to HR for harassment.  But all I could do was stare at it, almost as intently as I stared at the spreadsheet each and every day.  It was only the sounds of people approaching that brought me back to reality and made me hide the phone before anyone could see what I was looking at.

If I was already distracted at work by the Very Important spreadsheet that I was still trying to understand, the picture of your cock did nothing to help as I found my attention wandering to my phone.  At first I had glanced at it occasionally, but as night came and everyone vacated the office, I was practically staring at my phone as the image of your cock burned itself into my mind.  I felt my own tiny falsehood of masculinity twitch as I continued to stare at your magnificent member, steadily getting hornier and hornier as I studied the contours of your head and imagined what it must feel like to touch… to suck… to force itself inside me.

I was startled out of my lustful gaze by the sound of my office door closing.  That’s when I looked up and to my horror, I saw that your face cheerfully staring back at me.  That’s when I looked down at myself and saw that I had been tugging away at my small penis, stroking it raw while I was consumed with the image of your cock.  Despite the fact that you had literally caught me with my pants off, I continued to stroke away as if my life depended on being able to experience the bliss of release.  Whatever shame I might have had was simply overwhelmed by my desire to cum.

Try as I might to stop, I couldn’t.  If anything, your mere presence made me even hornier and I felt the need to cum even more.

“I sent that picture as a joke, but it seems like you really are nothing more than a perverted faggot!”

It wasn’t even a question – just a statement about who and what I was.  I wanted to disagree, but his words just made me hornier and an unwanted moan escaped my lips as the word “faggot” rolled around in my mind.

“I should have fired you a long time ago, but I kept giving you chance after chance to do the simplest task and tell me what you see in the spreadsheet.  Instead, now I know exactly what you’ve been spending all that time doing.”

I mewed pathetically in response as I felt the shame of disappointing a great man like you.  I really did try!  It was just so hard to concentrate no matter how hard I stared at the screen.

“But I’m not a cruel man,” you say as you laugh, almost as if you told a joke that only you could understand.  I watch as you deliberately step closer toward me, my mouth practically watering as I couldn’t help but notice the growing bulge ready to burst out of your pants.  I could feel my tongue practically tingle as I imagined using it to lick your member, feeling the texture of the skin that I had studied so carefully, imagining the overwhelming musk of your scent filling my nostrils and the taste… my god, it must taste so wonderful.

You stood in front of me, your bulge practically inches from my face, as you looked down at me.  “Tell me what you are,” you command coldly before adding, “and I’ll give you what you want.”

Without looking away from your crotch, I mumble in desperation, “I’m a faggot.”

“Yes, but I don’t want a faggot,” you derisively spit back at me.

My heart skipped as I saw you take a step back away from me.  That’s when it all become so clear.  The spreadsheet I had be staring at for some long, all those numbers thousands and thousands of rows of numbers that seemed to make absolutely no sense or had no pattern, it was so obvious that I couldn’t believe I had missed it all along.

“I’m a sissy!”, I desperately shout at you to try to stop your retreat.

I could hear your mean laughter in response to my declaration, but I was ecstatic when I saw you step closer to me again and watched as your hands slowly undid your fly and let your monster out of your pants.  I didn’t even flinch as it practically slapped me in the face before it hung in front of my eyes.  I felt my cock squirt a little, but I still couldn’t find any relief.  My tongue instinctively began to reach past my lips as I leaned my head forward to meet your cock.

“STOP!”, I hear you shout at me right before I could finally taste you manhood.

I whimpered but froze in place before turning my eyes up to look at you.  Your mean sneer told me exactly what you thought of me, but I didn’t care anymore.  I was a faggot… a sissy, and you were my better.

You ask a simple question, “How will you address me from now on?”

Deep down inside, I knew the answer and I didn’t hesitate: “Sir.”

“That’s right you dumb sissy faggot.”  That’s when I felt you reach down to grab the back of my head before you forced me forward and down onto your engorged cock.  I began to gag as I felt your giant manhood brutally force its way down my throat, but you didn’t care and held me down as I struggled to breathe.  I was in so much pain, but I also felt ecstatic as I finally understood what the spreadsheet was telling me.  

This was my purpose, my reason for existing! 

I am a sissy and my job is to be your personal cocksleeve.  By keeping you happy, I can help this company become even more successful than it already is!

You roughly force my head away from your cock so that I could breathe again before pushing me back down to fill me once more.  This happens over and over until you build a confident rhythm and begin to fuck my face.  I can barely see anymore as I’m crying tears of pain… and tears of joy at being used as the sissy faggot that I knew I always was.  I was just too stupid to see that reality and I was so lucky to have a young, brilliant, amazing man like you to show me my place and to tell me what to do.

After what seemed like an eternity, I could feel your cock begin to violently spasm as you gripped my head and pressed it against you so hard that my face was practically buried in your crotch.  Seconds later, a white hot stream of liquid emitted from your cock as your sweet nectar began to fill my throat and pour down into my stomach.

At that moment, I finally came.  It wasn’t as spectacular as your manly eruption as I practically spurted pathetically while making a mess of my pants, but it was a release all the same and I felt a sense of calm and bliss as I happily drank your cum while having my own pathetic orgasm.

I barely noticed as you pushed me off your cock and wiped yourself clean on my face as I continued to enjoy the post-orgasmic bliss of my release.  “I knew you’d make the perfect test subject for my little virus.  Things are going to get so much better for me now and I have you to thank, my pathetic little sissy.”

“Uh huh,” was all I could manage to utter as waves of pleasure continued to roil through my body.  Your words didn’t mean anything to me any more, I just wanted you inside me again.  I sank to my knees and began to crawl toward you, reaching out with my hands at your crotch before I felt you kick me away to bring me back to reality.

It was at that moment that I realized exactly what had happened and exactly what I had done.  I felt sick and started to gag as the taste of your cum registered in my brain, but the shame of being used by you… of cumming in front of you… it was all too much.  But despite my desire to try fight back, all I could do was pathetically cry in front of you as you started to laugh again.

You told me that you had a lot planned for your future at the company, but that I’d be your special project that you would devote much of your attention.  I wanted to ask what you meant, but you told me to go home and wait for your surprise.  As I moved to clean myself off, you laugh at me again and tell me that I need to “wear you” for the rest of the evening like the sissy I am and leave.

The next morning I woke up to the sound of an early morning delivery, embarrassed that the delivery man saw the dried cum on my face because he insisted that I had to sign for the package.

I dreaded opening the box, but I also knew that it would be the only way to get a taste of your cock again and practically tore it open when the image of your magnificent member flashed into my head.  In it I saw several items that were new to me, but somehow I instinctively knew what they were for.  I pulled out a chastity cage and took off my pants, before awkwardly slipping the cage onto my pathetic penis, feeling it press against the cold hard steel as the thought of trapping myself began to turn me on.  As I clicked the lock shot, I knew that you would be the one who would hold my key for me – permanently.

The next thing I saw was a fancy looking box that contained steel butt plugs of increasing sizes.  My eyes were immediately drawn to the largest size, dreading at what that might feel like, but I was happily able to use the smallest one instead.  I took it out of the box and sucked on it to provide some lubrication before reaching behind me and shoving it inside my ass.  I could feel my penis twitch again in its new prison as the sensation gave me waves of pleasure, but I knew that I would not find release any time soon.

At the bottom I found a small laptop that I hurriedly plugged in and turned on, seeing only two icons when it had finally booted up.  One was the familiar looking spreadsheet that I knew I would be studying intently at home as much as I did at work.  The other was a document that contained instructions for me, telling me that I needed to start ordering more appropriate clothes to wear, complete with links to women’s clothing stores and lingerie stores, that I needed to begin beauty routine to remove all the hair on my body and plaster my face with makeup, that I needed to order special hormone pills that would improve my appearance and take care of my pathetic little problem currently locked in its cage, and most importantly, that I needed to study hours and hours of porn to learn how to please a real man.

All of these purchases would be at my expense of course, since I should be grateful that you would take the time to give me all this attention even after catching me masturbating at work and not firing me on the spot.

While I was preparing myself to look more like the sissy faggot that I knew I was, I noticed that everyone at work became very invested in their own spreadsheets.  Maybe not as obsessed as I was, but during the few meetings I was now allowed to attend – usually on the floor under the table between your legs, sucking your cock – I could tell everyone was intently discussing the Very Important spreadsheet and occasionally as I passed by other people’s desks on my way to do your errands, I would see people staring at the spreadsheet on their screens.  It was hard not to become entranced myself and stare along with them, but I knew that I would be punished if I was late with your coffee or your files.

When I started coming to work in dresses, no one seemed to notice or care that I had so drastically changed myself.  My former colleagues began to see me as I saw myself, the pathetic sissy faggot who yearned for male attention and a cock in her holes.

Men who I thought respected me began to treat me like cheap trash, groping me whenever I was alone with them, before escalating to simply pushing me down onto my knees and forcing their cocks into my mouth right in the middle of the office.  It soon became routine for men to have meetings in the middle of a hallway, with me on my knees hungrily bobbing away at their cocks in order to suck them dry of their delicious cum.

Given that I wasn’t doing my original job anymore, you told me that it would make sense if I also took a drastic cut in pay but that you would help me but selling all of my junk and moving me into a tiny apartment that I could afford to rent if I did some special favors to the landlord and his friends.  I wanted to protest, but your mentorship and guidance really meant the world to me so instead I happily agreed to everything you suggested and soon found myself in a bachelor apartment that was barely bigger than the living room of my former condo.

You told me that you’d help me by controlling all of my money as well and I happily signed everything away to you so that you could manage that for me.  That’s when you began to schedule appointments with different doctors to help me improve my appearance, giving me the breasts I always knew I wanted, fixing my feet so that I would always have to stand on my tip toes or wear heels, correcting my voice so that I would sound more like the sissy that I knew I was.  If it wasn’t for the tiny piece of locked up flesh that reminded everyone that I was a sissy faggot, people might have mistaken me for a real woman!

If I slowly descended into being a sissy whore for the company, you had a meteoric rise and soon became the owner’s right hand man and at some point you practically began to run the company yourself.  No one seemed to mind how implausible your rise was – in fact, everyone seemed quite pleased that you were in control and all I could do was be grateful that such a powerful and important man still took time out of his day to manage my life… even if I didn’t get to taste your cock as often as I used to.

For my part, I became the best at being the office cum dumpster, and as soon as I was able to work up to the largest plug in the box, I knew I would be able to serve two men at the same time and double my efficiency.  I was happy because I knew you would be pleased at how productive I could be now that I could serve more of your employees.  I practically came when I saw you walk up to the men who were using me and they told me how happy they were to have a sissy to relieve themselves with.

That’s when you told me how I could increase my productivity even more and told me about my final surgery that would improve me.

I practically jumped up and down in joy as soon as I realized that I would lose my now dead nub of flesh and have a new hole that men can use to release their stress inside me!  I was so happy that I could be a better sissy whore for you and be a better employee for the company.  Maybe you would even start using me again!

It was almost one year to the date that you had caught me in the office and I discovered my true self as a sissy that I had my surgery that made me the best office cum dumpster that I could be, and now that I was fully recovered, you had given me this beautiful black dress and told me that you had a special event for me to attend.

I had a big smile on my face when I opened the door to my tiny apartment and saw you waiting for me.  I thought maybe you’d have me take the bus, or if I was lucky, you’d make me pay for a ride with my meager savings or one of my holes, but to have you here instead?  I could already feel my new gash begin to heat up at the mere thought of your special attention for me.

You led me to your limo and we drove to a fancy reception hall where you told me you had an event just for me and this special occasion.

When we arrived and entered the hall, I was confused because I saw a group of men all dressed in black suits as if it were a somber event.  Many of them were men from the office whose cocks I grew to love, but I also noticed some former friends of mine, and even my father and brother.

Seeing the confusion on my face, you began to explain, “This is a funeral for a stupid man who thought he was better than me, but I didn’t want everyone to be down thinking about someone who was so insignificant, so I thought who better to bring than my favorite whore Olga to liven up the room and make this into a party?”  You lean in close to whisper in my ear, “And don’t worry Olga, you don’t need to study your spreadsheet any more.  I want you to be fully awake to understand exactly what I’ve done to you, you little sissy faggot.”

I blinked several times, remembering that I hadn’t been studying my Very Important spreadsheet for some time now, a fog slowly lifting from my mind as I began to process what had happened to me.  I turn to face you with an angry look on my face but before I could say anything, you stop me and give me a sneer, “As far as the world knows, you are an illegal immigrant from some backwater Eastern European country with no identity or paperwork.  I’d be more than happy for you to give me a reason to report you to the authorities and to have you deported.”

You shove me to the ground and tear my dress off me, stripping me of the only dignity I had left as you grab my ass and shove your cock deep inside the virgin cunt that you had given me.  The sheer amount of pleasure overwhelmed any thoughts of resistance I had as all I could think about was the pleasure of having your cock inside me.  You signal to the group of men to come forward, but single out my father and say, “Since this reception is for your son, I think you deserve the first go at the entertainment.”

My father didn’t hesitate as he pulled out his cock and shoved it past my willing lips.  I know for sure you must have done something to him, the same thing you did to everyone at the company… and to me.  But in that moment, all I cared about was the fact that I was being filled and that I would be having lots of cum tonight.

Feeling your hot seed shoot into my newly constructed cunt was the trigger that sent me to my first of many orgasms tonight.  I didn’t even have time to recover because as soon as you were done, another cock – this time my brother – entered from behind me and began to rape me harder than I had ever been used before.

“What a touching family moment,” you laugh as you watch the three of us fuck each other.  You sneer at me and tell me that I would be working in a new role, “I can’t have someone undocumented working for me at the office now, but you’ll make a fine whore.  Consider this an audition for all your former friends and family and maybe they’ll pay to fuck you next time.”

You look up to my father and ask, “How does this whore feel?  Do you think you’d want to use her again?”

My father grunted as he held my head tight against his crotch as he came, “She’s definitely a great cock sucker.  Maybe I’d pay her 5 dollars for a suck and fuck sometime.”

You slap my father on the back and laugh, “That’s right, Olga here is a five dollar whore.”  You then turn to the crowd and add, “But don’t worry everyone, she’s free for this evening!”

You look down at me and give me a final triumphant look as you say, “I hope you enjoy your new life.  And if you behave, maybe, just maybe, I’ll hire you back as my maid and nanny.  I’m going to marry the owner’s daughter and she’s going to have many, many children so she’ll need some help.  How does that sound?”

I gasp for air as my father pulled out of me and used my hair to wipe his cock clean.  I wanted to cry, to shout, to scream in defiance, but all I could say was, “Yes sir, thank you sir.”

My fate was sealed.  I was now and forever Olga the sissy whore and, if I was lucky, future nanny to your new brood.  I didn’t have much time to think about it though as the next cock soon came to replace my father’s and I was back to work as the party’s entertainment.  I watched as you walked away from me and left me to my new life.  But none of that mattered… all that I cared about now was making sure every man here was happy with me so that they would hire me out again.  After all, how else was I going to making a living?