Drinking and dressing is not a good combo

I woke up with a groan, my alarm blasting in my ear. One hand groped feverishly for the loud blaring alarm while the other went to my head to calm the pounding going on. After fumbling for several seconds I was able to turn off the infernal blasting and lay back with another groan.

“Fuck, I can’t drink like this. That cheap whiskey gives me the worst hangover”

I grab my phone and look at the time and shoot up in a panic. 8:30 am! I have to be at work at 9! Fuck fuck fuck!

I swing my legs off the couch and stand up and run to the bathroom. As I’m running I notice the tickle of hair against my neck and shoulders and a lot of air rushing up against my “downstairs”. I look down and a small but very visible cleavage stares back at me, contained by the fitted white blouse and the black velvet bustier. The rush of air along my junk was from the short pleated miniskirt swaying from side to side on my hips, with my white thigh high socked legs coming out the bottom. Fuck! I’m still wearing this girly get up! Shit shit shit!

I rip off the blonde wig with its two pig tails and start unbuttoning the blouse while rushing to the bathroom. I see my red glossy painted nails trying to rid me of my cam girl wear and panic a bit, but first things first is getting this slutty outfit off of me. Fuck the buttons are on the wrong side! Goddamnit hurry. Finally unbuttoning the blouse and throwing it aside, I rush into the bathroom in just the black velvet and mesh bustier and mini skirt and thigh high socks.

I look in the mirror and see the bright glossy red lipstick still on my lips, making them look still very plump even slightly smudged. Looking at the clock I have no time for a shower so I quickly wash my face and scrub off the lipstick. The red was washed away but my lips looked much pinker and puffy from all the scrubbing, giving me a slight feminine pout. I threw on some deodorant and brushed my teeth and did mouth wash to try and get rid of the horrible stale **** smell from me. It was disconcerting seeing my face in the mirror doing all these things on top of a slutty female body wearing a little bustier and mini skirt. But I didn’t have time to think about that as I rushed over to my bedroom to change.

I shimmied the skirt down and pulled off the thigh high socks leaving them in a pile on the floor. I struggled for a bit with the hooks in the bustier but finally got them undone, breathing a sigh of relief as it fell to the floor. No wonder girls love taking their bra off when they get home. I took off the black mesh and velvet panties, leaving me back to my normal male self. My cock immediately sprang to attention now out of its tucked prison.

I opened drawers to grab some clothes, simple polo and khakis for the office when my phone rang.

“Hello???” I asked exasperated as I reached into a drawer to grab some underwear.

“Carl, it’s Derek. Are you on your way to the office? We have the presentation to the customer at 9:30.”

Derek’s my number two guy. He’s a nice enough guy, very hard working, but I swear he’s trying to get my position as lead manager.

“Yes yes! I’m on my way. I’ll be there” and hung up. Fuck I forgot about that presentation! Why the fuck did I drink so much last night son of a bitch!

I slid on the underwear, so stressed out that I didn’t realize I reached into Allie’s drawer as I settled the lacy red cheeky panty on my hips. A shiny red satin gusset and back was connected by red lace waist band. The cheeky Brazilian cut panties left half my cheeks exposed. Grabbing my khakis and putting them on quickly, I didn’t even realize what I had on as I was too focused getting ready. Sliding on the blue polo and a pair of socks, I ran to the door to get my shoes on with my keys and briefcase and practically flew to my car.

Arriving at the office, I ran to the door breathing heavily before stopping to compose myself. I checked myself in the reflection of the glass doors brushing out my hair so it wasn’t so much of a mess and straightening my polo. I saw my red nails while smoothing out my hair and immediately stuffed them in my pockets. Fuck fuck fuck. I have blue latex gloves and a face mask at my desk I can put those on and cover up these nails and lips. For the first time ever, thank god for Covid.

Taking a deep breath to steady myself, I walk in with a smile on my face to greet our receptionist Jackie. The 20 year old brunette didn’t have much between the ears and messed up quite often, but her chipper bubbly attitude more than made up for it. Or maybe it was her DDs she got for graduation.

“Hi Mr. Matthews! Howre you, like, doing today?? Oooo you don’t look so good are you feeling ok?” Jackie asked as she bounced in her seat waving to me, causing her chest to jiggle and wiggle with each wave. She wore a high necked sleeveless red body suit with a deep cut out to show off he artificially enhanced chest that was pushed up even more by the black satin bra, which I had a great view of since she was sitting down and leaning forward a bit. I could see she was wearing a white pencil skirt underneath with a high slit on her left thigh showing off her super tanned legs. On her feet were shiny red 5 inch stiletto pumps with no platform, giving her feet a severe arch. Her hair was slicked back in a high ponytail except for two highlighted bangs that hung on either side of her face. The amount of hair implied extensions but they were so well done that you could never tell.

“Hey Jackie. I’m doing well. Yeah a bit under the weather but I’ll be alright.”

“Oh my gawwwddd I hope you feel better! But whatever you have it made your lips GORGEOUS! Oh em gee I pay good money for lips like those!” Jackie giggled as her unnaturally inflated lips split into a smile.

I cringed at the thought of my lips as plumped up as Jackie’s and gave a nervous laugh in response before turning away and hurrying to my office. Thank god she didn’t see my nails. The whole office would hear about it from the gossip queen.

Getting to my office I quickly shut the door before rummaging through my desk for the gloves and mask and putting them on. I sighed in relief that I’d at least be covered for the day. I turned on my computer and grabbed my notes for the meeting before quickly heading over to the conference room.

Opening the conference room door I saw my deputy Derek Johnstone. The 24 year old came to us fresh from his MBA and quickly shot up the ranks. He’d only been here less than a year and he was already named my deputy. Don’t get me wrong, the guy knows his stuff and the team love him too. His nonchalant confident attitude, always looking out for the team, and charming smile make it easy to like him. But I feel like he’s definitely not content to stay as a deputy for long which makes me wary. He hasn’t done anything to undermine me, if anything he’s been a consummate professional, but I know he’s gunning for my job.

And it doesn’t help things the guy is handsome as shit. No homo of course but Jesus dude. 6’ 2” with wavy dirty blonde hair and the body of a surfer or swimmer. His torso is like an upside down Dorito with a trim waist and big broad shoulders. His blue eyes can go from easy contagious laughter to intense pressure that makes you feel uneasy so naturally. The guy is a natural alpha executive.

But I’m know schmuck either. Before Derek got here I was the rising star. I mean I’m only 27 and a manager for our warehouse team. I get along great with our team, I just don’t have the alpha male persona that Derek has.

“Hey Carl. Damn are you ok? You look beat man”

“Yeah yeah I came down with something. I’ll be alright. Let’s get this presentation over with.”

The rest of the leadership team came in, including my boss Brian Leary. Brian was in his 60’s but still looked great for his age with more salt to the pepper in his hair than I’m sure he liked. He had an old curmudgeon attitude, very traditional and old school about things. But he was well respected and the team liked working for a boss who was firm but fair. He gave me an odd look when I came in.

“Carl you look like shit. After this meeting I want you out of here and back home. Don’t need the whole team getting sick.”

Thankfully, the client was on video so I could kind of blend into the background as Brian got the meeting started. Derek was taking lead on this I was here for anything Kevin couldn’t answer but of course, Derek had no issues. The meeting went flawlessly with the promise of a great partnership in the future. Derek got congratulations from the team, especially from Brian. It miffed me a bit but I was still happy for the guy.

The rest of the team filed out leaving just Derek and I to finish up. As I was cleaning up some papers, they fell to the floor. I bent over to pick them up when I heard an odd grunt from behind me. Looking over my shoulder, I saw Derek staring at me with an odd look on his face, a mix shock with an odd look of desire? And that look quickly turned to a sly smile.

“You alright, Derek?” I asked.

“Oh yeah. Just… PEACHY. Sorry, must still be a little RED in the face after that meeting. They really tried to stick my BUNS to the fire. I’ll finish up here. You go home and rest up.”

I didn’t love that reaction, it looked like he was trying to hold back laughter. And who was he to tell me what to do. I’m his boss. But after last night, I was ready to head home and take a rest.

“Alright I will. Thanks Derek. I’ll see you next week.” I said walking out.

“Have a good weekend, Carl-I”

I froze for a moment cause I could have swore he called me Carli. I turned back towards him and he had a big smile on his face and waved before returning to finishing up. Must be my imagination and that shit I got up to last night.

I stopped by the rest room on my way out and upon reaching the urinal I about had a heart attack! Shining brightly through the fly of my pants was shiny red satin! I quickly headed into the stall and pulled down my pants seeing the satin and lace panties nestled on my hips. Looking over my shoulder, I saw the Brazilian cut cheeky panties encasing only about half my cheeks. The red satin gusset ran up my crack like a thong, widening into an inverted triangle at the waist band, while the red see through lace covered my cheeks. And covered was a strong word as only half of each cheek of that was covered.

At that moment I realized, did Derek see these when I bent over??? Fuck that would explain the weird look on his face and the odd inflections on words! Fuck fuck fuck! The guy was already gunning for me, already an alpha jock, and he’d just seen his boss sporting a whale tail like some slut!

Ok ok, settle down, Carl. You can fix this. He’s a professional, we won’t bring anything up at work. And even if he does, just say you and Allie were mixing things up. Or just say you have no idea what he’s talking about. They were just red underwear. Not a big deal. It’s ok.

Either way, I’m done with this girly shit. No more dressing up. I’ll figure out another way to get the money.

I drove home after stopping at a pharmacy for some nail polish remover, and walked in. I saw the aftermath of my night with an empty bottle of whiskey sitting next to my laptop next to the couch. The slutty school girl outfit was in a trail of discarded clothes leading to the bathroom, including the wig. I groaned seeing the mess and the aftermath of my drunken attempt to make money. No way would I do that again.

I sat down on the couch, flopping down and laying my head back trying to calm my still aching head. My laptop screen came to life, showing the new Twitter page for Carli. Fuck, I can’t believe I made this I gotta delete it and try to forget about this girly shit. Leaning forward I picked up the laptop and saw there was one tweet my account posted. It said:

“Cumming soon to a cam site near you! This new sissy girl like totally can’t wait to meet you boys! Xoxoxxx Carli Cummings”

With a gif of me blowing a kiss to the camera, my red lips matching my nails as they pursed into a kiss before widening to a bright toothy smile. My small faux chest on display in the skimpy white top, the tartan skirt hiked up a bit showing off the skin between the tops of my thigh high socks. A typical, but very hot gif of a slutty school girl. But that school girl was me. The tweet had ten retweets and a hundred likes with several comments. No chance was I opening up that can of worms.

I had to delete this shit, NOW! I went over to my profile when I saw I had a message. A message from BigDaddyM.

“Hey sissy girl, hope you like your first post. It’s already getting some attention. I put your name out there in some communities I’m a part of and the guys can’t wait to play with you. You’re going on tonight so be ready for me at 9 pm in just bra and panties. I’ll help you get ready for your first real cam show. We have a lot to go over.”

Fat fucking chance I’m doing that, buddy. Sure he gave me some money but he’s trying to order me around? And not even asking if I’m free tonight. Screw the is guy. I’m telling him it’s over.

“Yeah, no chance, buddy. I’m done with all this girly shit. Thanks for the cash though.”

Was all I typed in response. That’ll show him. I shifted in my seat and I felt the satin and lace on my behind rubbing. Oh shit I’m still wearing panties. I got up, completely forgetting my mission to close my Twitter account and headed to the bedroom.

Stripping out of my work clothes and the super dainty little panties, I felt much more myself. Sure my chest and underarms were hairless but they’ll grow back. After taking off my gloves I quickly removed the nail polish from my nails, feeling much more manly now that I didn’t have slutty red polish on my fingers. Putting on some normal boxers and a t shirt and shorts, I picked up the school girl outfit and accessories and carefully placed them back in their drawers.

My wild girly night now out of sight, I needed to feel like a man again. I sent a text to Allie saying I was taking her out tonight and wear something hot. Sure, money was tight but I needed to regain my masculinity. Getting a text back with a winky face saying she can’t wait, I laid down in my bed to get some shut eye. Tonight was gunna be a good night, tomorrow I figure out how to get out of this financial hole.