Sissy Alex is feminized by his boss

The story is so familiar I hardly need to repeat it. I’m talking about layoffs of course and today it was my companies turn. It started this morning, rumors started right away and by lunch it was clear what was going on – our company had been purchased by a competitor, and they were liquidating half the staff by sundown. Anyone judged to be redundant was gone. Practically our whole building was being fired.

We all want to think we’re unique, but I don’t kid myself, ultimately I’m identical to the scores of claims adjusters in cubes all around me. Shoot, I am a good deal worse than many. I am a 24-year-old college dropout with no skills and a painfully shy personality. Thin, small, frail, and leveraged out my ass in credit card debt and car payments, if I was lucky, I’d get a job in fast food, if not I’d end up on the street. My girlfriend would dump me for sure.

“Alex . . . Alex!” I looked up. I was Tracy, the ditsy but sweet secretary. She had tears in her eyes, and her normally flawless attire appeared a bit rumpled. “Anderson wants to talk to you now.” She said and burst into tears. I could still hear her sobbing as I walked down the long hall to my boss’s office.

“Alex, take a seat.” Mr. Anderson said. He was a large man and his frame blocked the light from the window behind him.

“You obviously know why you’re here today. You’re not a total idiot, that’s one of the things I like about you.” He paused for dramatic effect. “We’re firing people today of course. Whole bunches of people, entire branches are being systematically shown the door.” I couldn’t understand why he was drawing it out like this. He continued, “Of course, one of the things I like about my job is that I possess a great deal of discretion in my actions.”

He rose from behind his desk walked around until he was in front of me. He leaned back against the desk and I noticed that he placed one foot on each side of my legs. Sitting in my chair like that, his crotch was directly at eye level. I could see the bulge in his pants and how it stretched against his zipper. I felt ashamed that I noticed. I looked away from it for a moment, but was afraid of being disrespectful. I tried looking up at Anderson, my eyes wide and pleading, but I couldn’t hold his steely gaze. Ultimately I dropped my head and, afraid to close my eyes entirely, stared at the bulge, massive and masculine. He was talking, but I couldn’t hear him, all I could think about was that bulge, how big it was and how small it would make me look in comparison. I was thankful I wasn’t standing, as my penis is barely visible in the front of my pants. It was shameful to be fired, and even more so by a man so much larger than me – in every sense of the word.

“You don’t mind if I stretch a little do you Alex?” he said. I meant to mutter an “nuh uh”, but nothing came out of my mouth. He was looking down at me with his cruel, masculine handsome face. Having him this near with his legs positioned in that way underscored how tiny and frail I was compared to him. To my amazement he dropped his hand to his bulge and started to rearrange his big cock through the fabric of his chinos right before my eyes. I passed it off to locker room rules, the kind of thing confident fraternity boys to mark their territory.

“My discretion allows me to pick and choose who I want to fire, and who I want to spare. You know I could fire you right now, and you couldn’t do a thing about it. Practically the whole building is being laid off; no one would believe you were fired for any other reason. Complaints would be interpreted as sour grapes. Isn’t that right Alex?” My heart leaped, I felt hope for the first time that day, maybe I wasn’t going to be fired. I tilted my head up and looked at Mr. Anderson’s face for the first time, blinking my eyelashes slightly in an unconscious effort to please him.

“Do you know why Tracy was crying so much when she left my office?” He asked me.

“I supp . . . I suppose because you f, f, fired her, Mr. Anderson.” I could hardly speak, I sensed he was toying with me and all my terror was now back.

“That’s cute Alex, you have a little stutter there when you’re nervous. No Alex, I didn’t fire her, she quit, and because she quit she won’t get any severance package or any unemployment benefits. Stupid girl, and I was going to promote her too. Oh, don’t look so surprised. With everyone leaving, we’re going to need young, how should I say this, attractive people, to pick up the slack around here. I offered her the opportunity to be my very special assistant, but she decided she just couldn’t handle the added . . .” He stopped and smiled at me “added responsibilities.”

To my shock he began to ease down his zipper and I could make out the outline of a thick half hard penis pressing against the tight confines of his briefs. I couldn’t believe he was actually doing it and my mind couldn’t clearly process the situation. “So her loss Alex, but your lucky day.”

“I don’t know what you mean sir.” He fished in the fly of his briefs and pulled out his cock – – large, much larger than mine, heavy and thick, and growing longer every second. Adjusting himself he made sure to grab his heavy weighty balls and pull them through the opening as well. I was trapped between the chair behind me, his legs besides me, and now his large, thick, uncircumcised cock in front of me.

“Do you understand better now Alex? When I heard there were layoffs coming I looked around the office. Tracy was the hottest piece of ass in here . . . I mean even a faggot like you must have noticed those tits, didn’t you Alex?” The word faggot felt like a punch in the stomach.

“B, b, but I think there’s a misunder . . . misunderstanding sir – I’m not gay.” I blurted out. My mind was reeling. I wasn’t stupid; I knew what was going on. There was a misunderstanding. I was terrified of this man, but to my growing humiliation, I was also ashamed that my heterosexuality would likely mean my firing. For a second my little desperate mind wished I were gay. I needed this job.

“Gay? I didn’t say anything about you being gay Alex. I called you a faggot. A sissy, fairy, tiny . . . sexy little faggot.” His cock began to grow hard and lengthen, it rose so that the tip, shinny with a drop of precum, was pointed right at my face. Its impossible to say my reaction was anything but shock. I could hear myself breathing, nearly panting with fear, and I have to admit it, excitement as well.

“That’s right Alex, I called you sexy. You are sexy too. Don’t tell me you don’t know that. Don’t try to play dumb, like you don’t know how men look at you wanting to fuck that little ass of yours. I’m talking real men Alex, big strong, powerful men like me, not weak fairy sissies like you. Of course you must not spend that much time with men like that, that is, unless you’ve been sucking cock in secret all this time. Have you been sucking cock in secret Alex? Do you find yourself in those adult bookstores, on your knees, on those filthy floors, with some stranger’s dick in your mouth? Your urge to be a cocksucking whore must be powerful to degrade yourself like that.”

My cheeks were burning. How could he know? I had once or twice when drunk, but I’ve never admitted it to a sole.

“Now, as I was saying Alex.” Mr. Anderson continued ostentatiously stroking his cock inches from my face. “I looked around the office. I mean Tracy had the obvious advantage over you that she actually has a pussy, while you – – – well you just are a pussy,” he was smiling at his own sadistic banner “but apparently she’s religious or something, a devout Jew or Muslim or something like that – must be the same place she gets that hot olive skin I want to cream all over – anyway, she won’t fuck for pay, so its unemployment for her, and leaves me with you. Alex, you pretty little thing, you are the next sexiest thing in the office, the second hottest piece of ass. What do you think about that?” He eased a hand behind my head and pulled it forward. I am so ashamed, I was so afraid of being fired that I let him. Plus who am I kidding, I was aroused. I was hot. My cock, no I don’t deserve to call it that, my tiny little penis was rock hard and making a little tent in my pants. Mr. Anderson was treating me like his property, like a little fairy sex toy, and my reaction? I’m such a faggot that I had an erection.

I felt him press the smooth, mushroom head of his dick against my lips, he rubbed it back and forth across them glossing them with precum. “Kiss it.” He whispered. “Kiss my cockhead you faggot bitch.” Self-control got the better of me, I pulled my head back.

“But Mr. Anderson, I’m a man. A guy, I mean . . .” he pulled my head back by my hair so that my neck stretched and my mouth opened. His strong massive hand pulled my hair so hard it hurt and brought tears to my eyes, but it also turned me on. I was totally controlled by the man, and he knew it. He dismissively tweaked the hard-on in my pants with his fingers. I was so turned on, just from that I almost came. “You little queer, don’t play shy with me.” Mr. Anderson stood strait up so he towered over me. He placed his heavy masculine balls into my open gaping mouth. I could taste the salt of his perspiration and smell his odor. He was sweaty, hot, and masculine. His balls were so huge they overflowed from my lips.

“Alex, here’s the deal. I am offering you a new job as my executive secretary. I will double your salary, vest you in the pension, shoot I’m such a nice guy. I’ll even give you healthcare benefits. Alternatively, you can refuse this promotion and quit. Unfortunately your other job no longer exists. I have done my best to find alternative employment for you, and if you refuse, you’ll have no recourse. Do you understand? No severance, no unemployment.” He fished in his pocket and pulled out a shiny metal tube, a lipstick container. He opened it and showed the fresh stick to me – hot pink like what high school girl, or what a porn starlet wears.

“Tracy must have dropped this.” He said, though I knew for a fact Tracy would never wear a shade like that. He applied the makeup thickly to my lips so that they grew sticky and wet. He pulled my hair from behind so that I fell forward out of my chair onto my knees in front of him, his hand still controlling my head and my mouth still open.

“Alex if you accept this job there’s just one condition.” He said as he eased his cock between my newly painted lips. “You are never . . . NEVER to refer to yourself as a male again. Don’t mistake me Alex, you’re not a girl, at least not yet, but you are my bitch. My little sissy, cunt, bitch. Do you understand that?” I nodded my head, looking up at him with my eyes wide and his penis filling my mouth, the salty taste of precum on my tongue. He started to fuck my face more fiercely and I could feel the tears well up in my eyes, and roll down my checks. I was ashamed, humiliated, practically raped by this man, but to my further humiliation I was intensely aroused as well. To my horror my little dick was standing at attention and almost painfully pressing against my pants. Mr. Anderson pulled his manly cock out and slapped my lips with it, pressing it in my face, owning me through its placement.

“If you want this job little girly Alex, beg me for my cock.” He was rubbing his balls on my face and slowly stroking his massive shaft up and down, I heard him start to moan. “Times almost up Alex, if I come before you beg I’ll move onto the third sexiest bitch in the building. Beg me Alex, beg me for my cum.”

“I w, w, want you cum sir.” I whispered, aroused and ashamed, more motivated by my desire than my greed for employment.

“Louder Alex, scream it, I want everyone in the hall to hear you.” I was crying now.

“I’m ashamed sir, please, I’m embarrassed, those are my friends out there don’t make me.”

“C’mon faggot, you don’t think they don’t already know what a pussy you are, you don’t think you’re they don’t already gossip about what a little fairy you are at the water cooler. We all know about you Alex. You’re a cocksucker, what makes you think you can hide that. Oh yeah Alex, this is getting me hot, I’m so fucking close, scream it, scream, ‘Shoot your hot cum all over my face’ right now so they can hear you or I’ll, or I’ll, or I’ . . .” He was grunting, and I could tell he was going to cum. To my horror, I yelled as loud as I could.

“Cum on me sir, cum on my face, cum on my face like I’m a hot little bitch.”

“Oh yeah, fuck YES!” he screamed as huge shots of jizz flew from his cock and smacked me all over my face. My face was coated with his hot sticky load and I felt a hot salty jet smack onto my tongue. Pussy that I am, this made me cum as well.

“Oh my god.” I cried in a high pitch voiced sounding for the life of me like a shocked schoolgirl discovering she can orgasm for the first time. I felt my tiny penis leak its cum into my pants making a wet spot in my crotch, just like I had a pussy wet from the excitement. Anderson was rubbing his half-hard meat in my face, moving his cum around and smoothing it over my lips and cheeks, using his manly dick as a paintbrush to cover me so I glistened. He was the alpha Rocky, and I was his bitch, he had taken me, and was now marking his territory with his cum.

When it was done, he flung the door open, his thick juicy sticky cock still hanging free. I looked out the door, on my knees, my face covered with cum, and my lips painted pink like a girl — there was no mistaking what had occurred.

I saw the two people still left in the office staring at me in shock. There was Lucy from accounting, the one I always joked with at the microwave. She had a pretty face but was a little plump. She must be who Mr. Anderson thought was the third sexiest ‘piece of ass’ in the building. Then their was James, oh my gosh, my basketball buddy James – what must he think of me? Then I looked at him and realized he was kind of small and frail too, just not quite as cute as me. The fourth sexiest bitch. I wondered if he would have been as compliant a slut as I was, but to tell you the truth I hardly cared. With pride that astonished me I realized that Anderson thought I was sexier than both of them, and with self-satisfaction I realized that I truly was.

“You’re all fired.” Mr. Anderson said. Go collect your severance. Say anything about this and you’ll never get a dime.” They started to yell, but he just slammed the door in their face. He turned to me wiping his hand with a cloth handkerchief and smiled

“So Alex.” He asked rhetorically “How did you enjoy your first assignment?”

My instructions were explicit. I was to go home for the weekend and prepare myself for Mr. Anderson on Monday. I was to remove all obvious traces of my masculinity ‘excluding your faggot sissy-stick of course’ in order to prepare myself to be his fuck toy. This meant shaving my body hair, clipping and painting my nails, sanding my calluses, and waxing my eyelashes. Anderson wanted my ass especially smooth and gorgeous. ‘I’m not interested in using any bitch with a hairy hole.’ He said. ‘I want your little pussy clean.’

I knew how my girlfriend Bella would react. It’s enough that I don’t deserve her, that she’s a drop dead knockout, that she attracts stares from men who are much larger, stronger, and more successful than I am. She has to put up with all that and now I was going to ask her to date a drag queen? How could I expect her to ignore the men who catcall to her on the street when we walk arm and arm? The men who yell, ‘Baby, why don’t you leave that shrimpy faggot, and date a real man?’ or ‘My dick weighs more than your boyfriend baby!’. After all, its not like I was going to be a faggot, I already was a faggot. Just yesterday I had dropped to my knees and sucked another man’s cock. I allowed him to cum on me. No, that’s not right. Allowed is the wrong word. I had begged for it. I was eager for his spunk. Now, ostensibly to keep my job, I wanted her to put up with me shaved and dressed like a slut everyday. There was just no way.

Bella is a bombshell, just incredibly sexy. She’s about 5’6″ with long black hair; she’s thin but with a ripe round ass and nice natural tits, big enough to look hot in a tank top but not so large that you think she has implants. She works as some sort of cocktail waitress, I don’t really know, she dresses sexy and stays out late and she always tells me how much she appreciates me for understanding. Who knows? I was lucky to have her as a girlfriend. I was in no position to complain even if it was true that she virtually never allowed me to touch her anymore. It was always ‘not tonight dear’ or ‘I think I have a cold, you better not kiss me’. I didn’t ask many questions, I was happy just to be allowed in her presence. Given that I would soon be a painted little fuck whore for Anderson my only hope of keeping her was to simply avoid her. I figured she would dump me eventually, I was just hoping to postpone it as long as possible.

I’d managed to avoid Bella most of the weekend. Friday night she’d stayed out late again and didn’t roll into bed until well after 5:00 am. She slept most of the day so that I hardly saw her. I managed to shave while she was at work Friday night. The most difficult part was finding a place to dispose of my pubic hair where Bella wouldn’t see it. It felt strange to be hairless. I felt rubbery until I covered my body with powder, and my little penis felt overly sensitive to any touches. It was difficult to just walk around the house as without leg and arm hair my clothes strangely caressed my body in a way I was not accustomed to. Needless to say I had a constant hard on and internally I was ashamed of what turned me on.

In bed Saturday night, Bella long gone to her Bar to work I allowed my hands to touch my little sex. It was hard and erect, awake and at attention. I tried to reclaim my masculinity, at least psychologically speaking by visualizing sex with Bella. She had rejected my recent advances and we hadn’t fucked in ages. I tried to imagine her as I saw her that first time she let me fuck her. She had been drunk and willing, her body taut and eager. She had offered herself to me on her knees with her face pressed against the carpet of our mutual friend’s guest bedroom carpet. Her hands were behind her and she held her cheeks apart, pushing first one, then two fingers up her asshole. ‘Fuck my cunt baby!’ She panted ‘Fuck my bitchy little cunt.’ And what a cunt it was. Slick and shaven, it was hot and pink, and I could smell her musky odor. Everyone knew Bella was a whore, and I desired her even more because of it.

By : Cute Little Thing

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