A Super Halloween

This is my entry into the 2022Halloween Story Contest 2022. I always like to reinforce that like my author name says, all of the stories I tell here have a basis in truth and are always based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers.

Please remember, authors & our stories thrive on ratings. We get better with feedback, so PLEASE leave your comments on our stories. I also love when people guess in the comments what parts are "Truth" and what I added for "Twists"

Everyone in the story is 18 years of age or older.

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I've always had a love/hate relationship with Halloween.

When I was a kid: loved it, because free candy.

High school: hated it, because I never seemed to be invited to any of the "cool parties".

College: loved it, because booze and coeds in slutty costumes.

After college: hated it, because new city, few friends, no parties.

Grad school: loved it, because sexy adventurous girlfriend.

In the couple of years after Grad school, I was back in a "hated it" zone. Similar to post-college, I was in yet another new city, working in a firm that helped companies transition from old to new ownership. As a result, I was rarely at the mid-west home office and I would spend 3-4 months at hotels and businesses around the country before moving to the next one.

I learned along the way that wherever I was, there was a certain "stigma" if you didn't participate in Halloween festivities. I was amazed that people would get angry and aggressive just because you weren't that into a holiday that wasn't really a holiday. So, at some point, I came up with the most passive-aggressive "non-costume costume" I could. One year, I purchased a simple Superman t-shirt - one that was blue with his old-school "S" logo in the middle. The only thing was that the material was like an Under Armor stretchy material, so that the shirt was tighter than usual on me. Being in my late-20s, I still had the body and muscles to pull of the look.

I then bought a pair of thick-rimmed glasses with clear lenses. Each year, I would simply throw on my usual business suit, unbutton the shirt and tie with the t-shirt underneath. Add the glasses and some hair gel to get one of my curls to fall to mid-forehead and voila - I was Clark Kent hiding his alter ego! For me, it was an easy costume that kept people off my back but basically allowed me to wear my regular clothes.

On the year of this story, I was working at the company's home office. It was in a downtown high-rise in the mid-west that was part of a larger complex that housed shops, restaurants, offices and a hotel. The owner of our company was either an investor or on the board for the complex, so we would often get small requests to help or support some of the other businesses that normally couldn't afford our services. I think it was some sort of "giving back" that Mr. Williamson did to support local businesses.

The week before Halloween (which was on a Friday that year) we all got an internal memo saying that the one of the bars downstairs was inviting all our employees to their annual Halloween bash. The bar was one of those late-90s franchises that was made to look retro - even though it was all manufactured and meticulously planned by marketing and branding teams. They were waiving any cover for all of us and giving us tickets that were valid for free drinks. Because the bar was the usual post-work meeting spot on Thursday nights anyway, the buzz among our employees started immediately with anticipation.

Whenever I was asked about going by coworkers, I would either dodge the question or give a non-committal response. I was swayed on Thursday when I was approached in the break room by a couple of coworkers, Lizzy and Claudia. Lizzy and I had worked together a few months previously for a client in Virginia. Her specialization was in IT and system migrations, while I was on the operations side. She was a tiny brunette with short, frizzy hair and a compact frame. She wore little makeup but was attractive in a "natural" way. Claudia, on the other hand, was the complete opposite. She was of Spanish decent (and pronounced her name with a "juh" sound in the middle, making her even more exotic) with a mane of dark brown hair with blond highlights. She was always perched on high heels and dressed like she stepped off a fashion runway. Her skirts danced on the line of "work appropriate" and her blazers did just enough to conceal the set of tits that were under her tight tops. She wore makeup that seemed like it was professionally applied to highlight her blazing eyes and pouty lips.

Claudia was in sales and if I'm being honest, drove me crazy when I first met her. She was demanding, could be rude, and spoke to everyone like they were slightly beneath her. The facts were that she backed it all up by bringing in high-priced clients that kept us all employed. Somewhere along the way, she and I formed a strange alliance in meetings: maybe because we were similar in age and experience, maybe because I didn't fall into her web of charms. We formed a mini twentysomething alliance and had developed a flirty, sarcastic banter over time, too.

When Lizzy asked if I was going to the party, I threw out my usual "I'm not sure. It'll be a game-day decision." That earned me an eye-roll from my work friend.

"Oh stop it with your 'I hate Halloween' crap." She scolded. "Everyone is going, it's right downstairs at the usual spot."

"Wait" interrupted Claudia, "Why do you hate Halloween?" I didn't miss her stare aimed at me.

"Like I've told everyone. I just don't like it. I think it's another excuse for people to get dressed up and drink. It's great for kids, but I just think the whole thing is overblown at this point."

Lizzy piped up, "Well, hate to break it to you, champ. But it sounds like Mr. Williamson and the owner of the franchise are trying to get the parent corporation as a client, so he is strongly suggesting that we all make an appearance. I guess one of the Regional VPs is going to be checking in on the location."

"Yes, so if we're getting dressed up in silly costumes on a Friday night to go to a bar we always go to, so are you." Claudia said. "Besides, I bet you could hook up with one of the girls from Logistics. I see the way they look at your ass when you walk through their area."

As they walked away, I laughed and said, "I'm calling HR and reporting you!"

"Good." Replied Claudia. "Tell them this, too." And she proceeded to show me a very well-manicured middle finger as she walked away.

It turned out that Lizzy was right. Mr. Williamson sent all the managers a 'strong suggestion' that we stop by the event to show the owner and VP our support. That night, I dug out my t-shirt and glasses and grabbed some gel to fix my hair for the party. Worried that the costume would be a bit too subdued for the event, I called Lizzy on her cell phone.

"Hey, weird question." I started. "Do you or the either of the kids have a red Superman cape by any chance?" I explained that I wanted a peek of something more as part of my costume and I figured she was my best chance.

"Ironically, I do." She said. "It's actually an adult Supergirl cape. Will that work under your suitcoat?"

"Yup. Perfect!" I replied. "I'm not taking it from you am I? I don't want to mess up your costume."

"No. It's fine. It's technically my costume, but I'm not wearing it for Halloween."

"Then why do you have a Supergirl costume..."

"Stop asking questions, Jay" she laughed. "I'll bring the cape tomorrow." I hung up with a chuckle realizing that I had a surprising, new, little tidbit about my coworker's private life.

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The next day at work, productivity wasn't at its highest. Some employees had worn their costumes to work while others were planning to change before heading down. There were bags and buckets of candy at various cubicles and offices, and the music had changed to a Halloween mix. I popped my head into Lizzy's office to grab the cape and touch base. She was dressed for the office and handed me a shopping bag with the cape inside.

"So, you changing before you go down tonight? I asked.

"Uh...I have bad news." She replied.

"What? Don't even tell me you're not going."

"Ok. I won't tell you."

"Are you kidding me? Mr. W said we all have to go! You basically told me I had to go!"

"I'm sorry! Ted has to work late, so I have to get home to take the kids trick or treating!"

We bantered back and forth a bit more until her phone rang and I left her office. The rest of the day went by as usual, but I noticed more and more employees changing into their costumes as it got later in the day. I was buried in a spreadsheet when I heard a knock on my door. Looking up, I saw Claudia in her usual attire of heels, short skirt and blazer.

"So, are you going to bail out tonight, too?" she asked.

"No. I already committed to heading down. I'll probably work a bit late and then head down around 6:30."

"Alright. I'm going to change and then head down." She pointed a manicured finger at me. "But you better not find a way to weasel out of this. I swear, I'll hunt you down if you do."

A few hours later, I packed up my stuff and did a quick refresh in the men's room. The office was mostly empty as I remerged with my modified Supersuit. What I liked about the costume was that I could still look normal in the public areas of the building just by buttoning and tucking in a few things.

Arriving at the bar, I saw much of the company was already there and had started imbibing on various spirits. I grabbed a drink and headed over to some of the people I knew. We all ordered, ate and drank. Looking around, I didn't see Claudia anywhere and I started to angrily stew thinking she had decided to bail, too. I was introduced to the manager and VP of the restaurant and put in some face time with Mr. Williamson. Around 9:00, I noticed that the executives all excused themselves and left the party, which was the signal for things ramp up a bit.

I found the girls from Logistics and was more than happy to buy a round of shots for the sexy cat, sexy nurse, sexy baseball player and even a sexy Mario. Dance music has started and in my buzzed state, I joined a whole crew on the dance floor. Abbi, the sexy baseball player from Logistics was bumping and grinding against me and I was starting to feel some constriction under my suit. After a few songs, I was sweating through my layers and decided to grab another drink at the bar.

As I was about to order, I heard a familiar accented voice behind me, "Don't tell me Superman is all worn out already." I turned to see Claudia and I stopped dead. She had her hair pulled up and back into a messy ponytail. It was being held in place by a floral scrunchie. She was wearing a bikini-style half-shirt, which left her arms and shoulders exposed along with her toned stomach. The shoulder straps where wider and ruffled and in a floral pattern and the bust had her breasts lifted in an extraordinary display of cleavage. Her legs were perched on a pair of high-heeled wedge sandals and bare ... up to the grass hula skirt that ended at her knees. When she moved, the grass would shimmer and move and I was able to catch a glance at her matching bikini bottoms underneath.

I made room for her to slide up the bar next to me ordered some drinks and said, "Where have you been? I thought for sure you no showed."

"No. I was with Mr. Williamson, the manager and VP talking about the account."

"Ha. I should have known you'd be angling to get in on that one."

"Fuck off. Like you won't try to get it? Big payday and close to home."

"Touché" I replied and lifted my drink to clink against her cocktail. We stood at the bar and kept chatting and drinking for a while. We were both drinking vodka tonics and they were starting to affect us both. As we drank, we naturally migrated closer to each other and kept 'accidentally' brushing up against each other. Claudia was playing with her hair more and I thought I saw her licking her lips.

"It's getting tight down here - want to head upstairs?" she asked over the noise of the crowd. I looked up and realized she was referring to the balcony area that ran around the perimeter of the bar. It was roped off for VIPs, so I asked how she intended to get us up there.

"It's where I was sitting with the big wigs." She replied. "Then I just sat up there and watched everything - including the dance floor." She smirked at me, grabbed me by the hand and led up to the staircase. The bouncer didn't give her a second look, he just nodded and let us pass. Claudia led me to a table in a corner that was a little booth with a cushioned seating area. From the seats, we could see most of the bar including most of our coworkers on the dance floor.

We sat down and the sofa forced us closer to each other. Claudia flagged down a waitress and ordered us another round of drinks. She had turned toward me so that her breast was pressed against the side of my chest and I could smell her perfume. I shifted (for a few reasons) and put my hand on her knee. Realizing where this was heading, we both started to lean in when we were interrupted by a cheery exclamation, "Halloween Shots! Only $10!"

We pulled back and saw a buxom waitress dressed as Dorothy from the Wizard of Oz with a tray of test tubes filled with colorful liquid.

"Uh...we'll take two." I said, reaching into my wallet.

"Don't be a pussy." Said Claudia. "Make it two each."

$50 dollars with tip later, Claudia and I were shooting down the sweet shots and wincing at the odd concoction of booze. She shuddered at the taste and when she looked up, we were close and face to face. I leaned forward and locked lips with her. My hand snaked to the back of her head and pulled her in tighter as our tongues started to wrestle. Claudia shifted closer and pressed her impressive chest against me, and I ran my other hand up her leg, caressing her thigh under her grass skirt. Claudia pulled away and shifted her head and starting kissing my neck which drove me crazy. We paused and came up for air when the waitress delivered our drinks. Once we moistened our parched mouths, we went back to our activities.

Claudia's hand was now rubbing up and down my leg, occasionally working its way over my covered crotch. I had moved one hand up and was caressing her breast, trying to play with the stiffening nipple under her top. We were turned toward each other, and she was rubbing her groin against my thigh. This continued for a while: drinking, talking, kissing, groping. Even though I didn't want to stop making out with my sexy co-worker, I realized that we were quickly becoming "those" people in a bar, putting on a PDA that I would normally criticize.

"Want to get out of here?" I asked.

"Yes. Right now." she replied huskily.

We slid out of the booth and worked our way around the perimeter of the bar attempting to avoid the eyes of our remaining coworkers. We went to the plaza entrance only to see a huge line waiting for taxis.

"Fuck" I muttered. "My car's in the garage, but I can't drive right now."

"The hotel." Claudia was making a statement - not a request or a suggestion, so I grabbed her hand and we started walking through the concourse to the connected hotel lobby. The entire complex was like a weird science fiction or fantasy movie. The highly polished glass and chrome building was full of strange people in strange costumes seemingly wandering around.

As we entered the lobby, we saw other partygoers being turned away at the desk and I felt my chances of banging Claudia slipping through my fingers. I said a disappointed, "Fuck" for the second time in the span of a few minutes.

"No" Claudia said. "Follow me." She dragged me to a seating area around the corner away from some of the noise and activity. "Go in the bathroom and put yourself together as best you can."

I did as I was told and thanks to some water through my hair, I actually made myself look somewhat presentable. I buttoned up my shirt, took off the fake glasses, then removed and folded up the cape. I put my suitcoat back on, tightened my tie, then picked up the cape and held it under my arm as I walked out to find Claudia. She was on the phone as I approached, and I heard her finishing up her call.

"Wonderful Annika. I appreciate your help. I'm with Mr. Reynolds at the bar now, so I'll walk him over. Thank you so much for your help." Closing her phone, she grabbed me by the hand and said, "Let's go."

"What the hell did you just do?" I asked.

"Simple. I called the hotel, asked for the manager on duty and explained that you were one of the executives that were meeting here tonight. I dropped the names of Mr. Williamson and Mr. Helwig, who own parts of this complex, and said they would really appreciate any room they had for you tonight. Annika was perfectly lovely and said they would be sure to accommodate you this evening."

"Holy fuck. You ARE good at what you do."

"Let's get upstairs and I'll show you just how good I am."

This time, when we approached the lobby, there was a security guard posted by the door. He asked if we had a reservation and when we said, "yes" he let us in. We went up to the front desk and Claudia did all the talking. It was amazing to see her in full action. She wasn't slurring or showing any signs of the alcohol we had consumed. Despite the fact she was standing there in a bikini and grass skirt, she acted as if she had on her Armani power suit and was closing a deal. She introduced herself to Annika, apologized and joked about her attire, "had to dress for the occasion" and mentioned her meeting with the executives. She explained how I was supposed to fly out earlier that evening, but missed my flight and was going to spend the weekend instead.

"Oh, will you need the room for more than one night?" Annika asked.

"Yes, we got him booked on Monday morning, so three nights would we wonderful." Claudia replied before continuing her repartee. Listening to her, one would think that she and Annika were old sorority sisters. I suddenly understood why she was the best salesperson in the company. Watching her in action, she was smooth, professional, friendly and endearing.

At the end of the transaction, Claudia handed across her corporate Amex card, then her business card and a folded one hundred dollar bill. She told Annika if she could ever return the favor, to let her know. She took the room keys and handed them to me, taking me by the arm.

"Will you need assistance to your room, sir?"

"No" Claudia replied. "I'll escort him up myself." I could have sworn I saw her give her new friend a little wink as we walked to the elevator.

"That was amazing. I mean ... you were amazing." I stammered, legitimately impressed by her ability.

"No shit, Sherlock. I'm fucking good at what I do. Everyone thinks it's my tits and my legs and ass and yes, they don't hurt. But the fact is, I bring in the dollars I do because I work that same ass off to learn how to deal with people and convince them that what I want, is also best for them." The elevator doors closed and she added, "And I know what I want right now."

With that, she lunged toward me and pressed me against the corner of the elevator wall. Though she caught me surprise, I responded quickly and once again attacked her mouth with mine. I reached up under her skirt and got a firm grip on her bikini-covered ass, feeling just how firm it really was. I pulled her tightly against my swollen groin so she could feel my erect cock pressed up against her.