April Fool Office Sissy

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Coworkers prank him into coming to the office crossdressed.
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"Dear Colleagues

This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and ties for the girls and skirts and heels for the guys!). This is not compulsory, but it should be fun for staff and help us raise money for charity.

Regards

The Management"

I read through the email again, not really entirely believing it. My office was honestly asking its staff to come in to work crossdressed. It seemed odd, but it was also the perfect opportunity that I'd been looking for. This email was almost like the answer to my most deeply held wishes.

You see, I'd been dressing at home for a couple of years now, perfecting my most feminine look, loving the feel of wearing sensual lingerie, stockings and heels. All this time I'd been too timid ever to take my feminine self outside the apartment and into the wider world. I'd just been waiting for an opportunity, or rather for a sign, that this was something that I should do. And then that email from management had dropped into my inbox.

Today was Monday and the "dress up Friday" was just four days away. It was four days that I spent nervously picking out and perfecting my outfit. I wanted to look just right, to pass completely as a sexy office girl that nobody on the subway commute could ever suspect was really a guy underneath it all. I wanted my feminine side to impress my colleagues, the small team of three guys that I managed, my own boss Drake Thompson, and Jenny Macaulay, the secretary that I had a crush on.

Friday came and I was up early in the morning. I bathed and shaved my body completely hairless before starting to dress myself with trembling excitement. First I tucked my little hairless cock into a pair of lace trimmed black bikini-cut panties and then added a matching black lace bra around my smooth flat chest. Over my panties I added a black lace garter belt and then slowly slid a pair of sensuous shear stockings - the ones with a seam up the back - up my shapely, silk smooth legs and clipped the garters to their lace stocking tops.

Now dressed in sexy underwear, I began to feel more feminine already. In fact, it was hard to keep my pale little dick from making a small bulging tent in the panties or wetting the material with my precum. It was going to be hard to concentrate on work around the office if I kept this up.

I added a thin white blouse, whose material was deliberately light enough that my lacy black bra was tantalisingly visible beneath, and a pinstriped pencil skirt, and now I looked every inch the hot office girl. My makeup was in the form of dark eyeliner and false lashes along with red lips. Ever since I'd started crossdressing in my spare time, I'd been growing my dark brown hair out and now I teased it into a feminine wave. Finally, I added the finishing touch, a pair of black six inch stiletto heels that I'd been practising in until I had the perfect heel-toe walk that swayed my ass enticingly in my tight pencil skirt.

And then I was ready for the first time to leave the house as a girl. I checked myself in the mirror one last time - satisfied that I looked pretty fine, in my thick rimmed glasses, wavy hair and scarlet lips just like a fantasy of an office beauty - and then stepped out of the door of the apartment and set out for work, butterflies in my stomach with nerves and excitement.

On the subway commute into the office, my thin, practically see-through blouse and tight pencil skirt certainly drew some admiring attention from my fellow travellers. I began to get a bit of an insight into what it must be like for natural women every day as I felt the eyes of hungry, horny men running over me, checking me out, wanting me. I felt a strange mix of flattered and a little scared as a tough looking black guy a good head taller than me and with a broad muscular chest gave me an approving leer and a barely disguised lustful smirk. I could just tell that he was imagining what it would be like to tear off my neat skirt, pull open my stockinged legs and tear into me with his no doubt monster black beast of a cock.

I felt myself blush under his attentions and that dirty thought. Now that I could sense he was thinking this of me, I couldn't help but imagine it too. For all the time that I had enjoyed dressing in sexy girly clothes and looking pretty, I hadn't really before imagined being with a man, but I couldn't help myself now. It felt naughty, it felt wrong, and it felt exciting. Beneath my skirt and panties my little hairless cock began to twitch.

Finally, I got my thoughts under control, got off the subway and, my stiletto heels clicking on the sidewalk and my ass swaying seductively, I headed into work. I looked around, eager to see how my various colleagues had approached the task to dress up as the opposite sex. Would they all be in their boyfriends and girlfriends' clothes? Would they have outfits that looked deliberately half-assed and rushed? Or would others have, like me, thrown themselves into the task and transformed themselves into a version of the opposite sex more desirable than their normal selves?

I looked around for any answer to this and suddenly realized that something wasn't right. There were my colleagues, like every day, and they were dressed just like on any other day. There were no guys in skirts and heels, no girls in suits and ties. Nothing. It was just me, embarrassed and flushing red, provocatively overdressed in blouse, skirt and seamed shear stockings, and attracting the shocked and amused attention of the rest of the office.

"Wha...what...? I don't understand," I stammered, "Why aren't you... Is nobody else dressed up?"

"Ha ha! April Fool!" came a triumphant laugh from across the open plan room.

"God, I can't believe you fell for that!" joined another, equally amused.

I looked over to see the small team of three guys that I managed, sitting at their computers and turning to face me, laughing. If I had been embarrassed and humiliated as I came into the office, I was mortified now. I suddenly realized what an idiot I'd been. Of course today was April 1st, a day for pranks and tricks. How had I been so absorbed with the excitement of getting to doll myself up as my femme self this Friday that I had completely failed to notice that. Or the fact that the email (although addressed to "colleagues") had only me in its recipients. My team had set me up to come to work dressed as a girl and had succeeded incredibly in embarrassing me. I don't think that even they could have anticipated the lengths that I would go to to look girlish though and that just made them even more gleeful.

"I never thought you'd be fooled by it at all, but these two were insistent," said one of my subordinates, Terry, as I embarrassedly paraded my feminine look in front of the whole office on the way to my desk amongst my team.

"Yeah, I thought we'd get a laugh at you in a wig and a skirt or something," added his colleague Shawn, "I never expected you to put such an effort in to looking like such a girl!"

"Yeah, wow, you make one pretty little piece of girly ass," laughed my other subordinate Ben, "You look more like our secretary than our manager, "Lulu"!"

From then I knew that I wasn't going to escape the name "Lulu", that was what I'd be from then on. Even if I could make it through today with some of my dignity in tact, I knew the three guys that I was supposed to be in charge of would never again respect me as their superior, not when they could bring things back to "Lulu" again. Being a somewhat timid, slight white man managing a trio of virile young black guys it had always been tough to assert my authority and this April Fools prank was making it no easier.

As the morning went on, I managed to get my head down and get some work done and even get my team to do a little as well. All throughout, though, I was aware of the glances and titters from around the office as they looked at me in my feminine outfit. No matter what I tried to say to stop it, I could also do nothing to prevent my team from teasingly referring to me as "Lulu" throughout. And every time they said it I felt again the slapping humiliation of that first realization that I'd been pranked and embarrassed in front of colleagues who I could never look in the eyes in the same way again. And then my boss called me into his office.

"Come in and explain yourself," said Drake Thompson, shutting the door behind me.

He was about 45 years old but still in great shape: black skinned, tall and broad shouldered in a well-tailored suit that served to show just how great a body he had. He stood in front of me and ran his eyes judgmentally over my blouse, skirt and stockings, taking in my false lashes and makeup.

"I hear they're calling you "Lulu" now, Lucas," he said, "What's this all about?"

"It...it's...just a prank," I stammered. I had always been a little bit both intimidating and awed by my boss, who I had always tried to impress. This, though, certainly hadn't been how I'd planned to catch his eyes. "An April Fool..."

"An April Fool?" he said in his deep, commanding voice, "You were pranked to come in dressed like a slutty secretary?"

"Er... well... yes, kind of," I blushed again under his judgmental gaze, "My team sent an email saying today was "dress up Friday" and to come in dressed as the opposite sex."

"And you didn't think that was odd? And didn't clock that today was April 1st, "Lulu"?"

"No, sir. I... I didn't think."

"And with that short notice, you still come in with all this sexy finery. You didn't just throw this girly outfit together, did you, Lulu?"

"No, sir. It's... well, I had some things lying around," I was getting more and more uncomfortable and flushed as the conversation went on.

"Are you wearing lingerie underneath that?" he had obviously noticed the way that my expensive black lace bra was very visible through the blouse and I began to think that that had not been a very good idea at all. "I think that's really going beyond whatever a "dress up Friday" would involve, even if it were a real thing!"

"It... it seemed like the appropriate thing to wear, sir... I mean, with this blouse and skirt."

"You know I should discipline you. This outfit is hardly within the dress code. Even for a female member of staff, having your bra so on show like that would be seen as likely to distract her male colleagues."

"Yes, sir... I... I understand. I must be disciplined."

"But, seeing as you've done such a good job of making yourself a perfect embodiment of the slutty office girl, then perhaps your punishment should fit the crime."

"Sir?"

"Get on your knees, Lulu," my boss said, standing in front of his desk, his legs wide in a commanding stance as he unzipped the fly of his suit pants, "You want to look like a slutty secretary, maybe you can act like one too."

"Sir... I don't know... I mean, I didn't want... It's not something I've ever done..."

"Listen, Lulu, you can either get on your knees and blow my big black cock. Or I'm giving you a formal disciplinary write up and news of your girlish dress up will go right through the company and right up to the directors and clients. Nobody will know what goes on in this office. You have my word."

Faced with what seemed like no choice, I followed my boss' command, dropped to my knees and watched as he pulled out what must have been the biggest black snake I'd ever seen. It made my little white dicklet look laughably small as it flopped into my face, already getting semi-hard and as thick as my wrist as Drake began to stroke the throbbing, veiny shaft.

"Suck it, Lulu, you dirty little bitch," I couldn't believe the language coming out of my normally respectable manager's mouth, "You know you want that fat black cock!"

I took the shaft in my right hand, feeling it hard and alive and throbbing, feeling it get harder as I stroked along it, pulling its glistening purple head towards my painted girly lips. I opened my mouth and let my tongue flick across my boss cock, circling the head and tracing all along the shaft. It felt warm and fleshy and very exciting. I might never have given much thought about sucking dick before in all my experimenting with dressing up, but right now I knew that this is where it had been leading. I couldn't help but feel weak, submissive and needy in the presence of my boss' dark powerful member. I just wanted it inside me.

"That's it, Lulu, the office whore, swallow my dark meat," Drake said, pushing his fat black member between my lips, "Don't you love the taste of the boss' black dick?"

I began inexpertly to bob back and forth on it, taking in the first couple of inches of what must have been around eight of pure black masculine hardness. This wasn't enough for my horny boss, though. He grabbed the sides of my head and pushed deeper, making me gag. Still he wouldn't stop. He was fucking my face now with no doubt of who was in control. My mouth, indeed my whole expensively made up girly body, were just for him to use and abuse.

"Get ready for it, little white bitch, because I'm about to blow a nut," my boss said, "I hope slutty Lulu likes a big mouthful of salty cum."

There were tears in my eyes as my boss raped my mouth with his massive black beast and I choked and gagged, but I could tell from how stiff my own little dick was that this was where I belonged. My little black lace panties were getting stained by my own precum even as my boss' dick made my mouth drool.

Then I felt it, my boss' ejaculation hit the back of my throat. I tried to swallow but it was all too much for me with a big black dick in my mouth. Cum leaked from the corners of my wet lips. Drake withdrew his cock from my mouth and, still jerking the shaft, shot a couple more streams of cum across my lips and cheek and over my glasses.

"That's it. You make a good little white bitch for your black boss, Lulu," said Drake, "Looks like I won't have to write you up after all. Now, you can go."

He tucked his still massive but now limp black pecker back into his suit pants and I got up and tried to make myself presentable, wiping the cum from around my lips and off my glasses, noticing it drip onto my blouse.

As I exited the office, still licking a little sticky salty manjuice from my lips - kind of enjoying the intoxicating taste of my boss' power - I was shocked by a cheer that went up around the office. My team had turned the screens of their computers to face the room and were livestreaming from a camera in Drake's private office. Everyone had seen everything.

"You know when I said nothing that you do in here would ever be known," came my boss' deep voice behind me, "Well... April Fool!" He laughed, slapping me on my pencil skirted ass. "Your team rigged up that camera so the whole office could see what a naughty little bitch hungry for black cock you can be!"

"God, I can't believe how gullible you are, Lulu!" laughed Terry from his desk, "It's April 1st. How do you keep believing what everyone says to you?"

I felt my cheeks flush red again as the humiliation of earlier - the raw embarrassment that I thought could never be topped - returned in even greater amounts. There were warm tears in my eyes, and not just from gagging on the monster black cock I'd just been swallowing. I couldn't believe my whole office had not just seen me dolled up like a slutty girl but willingly sucking off the boss at work as well!

Utterly shamed, I hurried out of the room and staggered into the women's bathroom. Standing in front of the mirror, I tried to calm myself by fixing my makeup. I wiped the last of my boss' cum from my lips and glasses, licking it clean from my fingers. Sure, I was humiliated, but I couldn't not admit to loving the feel of swallowing a real man's powerful masculinity. Then I reapplied my makeup and lipstick and soon felt a little better about myself. Hell, if I was going to be seen by my office co-workers as a slutty sissy, at least I made a pretty hot one.

"Oh, I'm sorry, I didn't realize that there was anybody else in here," I heard a voice and turned to see that I was not alone in the women's bathroom, Jenny Macaulay was there too.

A perky, leggy blonde, Jenny had been my office crush from the moment that I started working here. I knew a couple of guys in the office had been with her - including Shawn from my team - and she was supposed to be pretty easy. I had been trying to get her attention for months but had made no progress. But now here I was sharing the intimate space of the women's bathroom with her.

"Oh, it's you," she said scathingly, "What are you doing in here? You may be dressed like a bitch, but the little boy's room is really for you."

"I... I..." I stammered without answering.

"My, but don't you make a pretty sissy," she grinned, looking me up and down, "And you got a tasty big black treat from the boss, didn't you?"

Was she flirting with me? I couldn't tell. I'd never had this kind of chat with Jenny before. Perhaps she was into the new me. Perhaps I could still turn this day to my advantage.

"M...maybe..." I agreed.

"Bet it made you all excited having to submit to such raw black power," she said.

Her hands were now circling the hem of my skirt, slipping up under it and caressing my legs in the smooth shear stockings.

"Mmm, yes," I decided to agree, "I loved being made to kneel and submit to it."

"Did it get you nice and wet, like a good little slut?" Jenny said, lifting my skirt to reveal my black bikini-cut panties, tented out by the bulge of the erection she was giving me.

"Oh yes, so good," I sighed, the wet spot of my precum on my lacy panties enough to answer her question.

"Oh my God, no wonder!" she giggled, pulling my panties aside and revealing my naked stiff hairless cock, barely three inches fully hard. "You call that a cock? Well, I'm not surprised your such a sissy, it's barely bigger than my clit. How puny and pathetic!" She took out a phone and snapped a picture. "Wait until all the women we work with as clients see this. You think it's embarrassing now, you just see how you're treated at every meeting you go to once our clients know what a tiny sissy clitty cock you've got, Lulu!"

She turned to leave, still giggling, leaving me with my skirt pulled around my waist and my admittedly pretty insignificant cock jutting out as hard and erect as ever, barely reduced by my crush's mocking belittling words.

"But...b...but..." I said, as Jenny walked out.

"But what?" she demanded, turning in the doorway, "But you thought I was into you, watching you debase and humiliate yourself like a pathetic sissy? Ha. I guess that's another April Fool's prank on you then. Yeah, I've known about your crush on me for ages, "Lulu", but if you think a hot piece of ass like me would be seen dead with a tiny dicked sissy bitch like you then you couldn't be more wrong. I'm only into real men with real dicks, big black ones like the boss or the guys in your team. Maybe a cock hungry bitch like you can understand that. Oh, and next time, use your own bathroom bitch boy."

And then she walked out and my humiliation was back again. So far today I'd been embarrassed by dressing as a slutty woman in front of the whole office, shamed by getting my face fucked on video by my boss' massive black member, and humiliated by being told by my long term crush that I was a pathetic excuse for a man with a tiny hairless white clitty cock. And it wasn't even half way through the day. This was turning out to be one hell of an April Fool's Day!

***

"Hey, Lulu, the boss wants to see you again," Shawn smirked as I returned to my desk after having some lunch.

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