The Trans Ultra Collection Vol 3

by Ursula Lovelace

  Now this was getting weird. Plenty of gamblers had weird charms and rituals to boost their luck at a casino. Management didn’t mind as long as they didn’t cheat. However, I never heard someone refer to a person as their lucky charm.

  “Good luck charm?” I asked. “Sir, are you feeling alright?”

  “I’m fine,” he said, wiping his tears. “Call me John. What’s your name son?”

  I had a name tag but I answered just to be polite. “It’s Ken, sir. How can I help you?”

  He stroked his chin. “I think you can help me out a bunch. I need a good luck charm in a pinch. You could be just the person I’m looking for. I’ll make sure you’re well compensated, Ken.”

  My ears perked up at the last bit. I was always in need of extra money. It wasn’t strictly speaking legal to do these kinds of things for guests. Then again, the casino was paying us pennies in the first place. “What do you have in mind, John?”

  He smiled. “My late wife, Barbara, used to be my good luck charm. I won so much money with her standing by me. It didn’t matter if it was at a poker table or a slot machine as long as she was there with me.”

  I didn’t really follow his line of thought. “I see…”

  John continued. “I need you to dress up in my late wife’s clothes. I need someone like her to be there with me while I’m playing. It’s the only way I can get back into the rhythm of things. I’m sure I’ll be back to winning in no time!”

  There was a lengthy pause as I digested that statement.

  “Is this some kind of joke?” I replied, blinking in disbelief. He looked too sober and rich to be a crazy person. “Or a scam?”

  “No scam,” he said, plainly. John took out his card key. “I have a room booked up in the penthouse suite.”

  I knew it was a legitimate card key. However, I didn’t know if the man was on the level. “Look, I don’t know about this-”

  He took out his wallet and pulled out a few hundred dollar bills. “How about ten thousand dollars? If I win something, then I’ll throw some of it your way as a bonus. Not bad for a few hours of work.”

  It was easy money compared to sinking a small fortune in a casino in hopes of a payout. I’d just have to dress up as a woman for an easy pay day. Drag queens weren’t an unusual sight at these kinds of places.

  However, I would be in a lot of trouble with my boss. Management could have me fired for working off the books with a guest. Worse, my coworkers would have unlimited ammunition to make fun of me. I couldn’t risk getting recognized while wearing drag.

  Sensing my reluctant, John put his wallet away. “I’m sure some of your coworkers will be more interested.”

  Considering the state of my bank account, I couldn’t let this opportunity pass. “Okay, I’ll do it!”

  John chuckled. “Excellent! I’ll take you up to my hotel suite. You won’t regret this!”

  As I followed the eccentric man up to the elevator, I got a better look at him. You wouldn’t have been able to tell that he was crazy. His clothes were quite expensive. He had a pricey Rolex on his wrist. Maybe he wasn’t lying about being a high roller.

  John wasn’t half bad looking either. He looked to be in his forties and in good shape for his age. A few of the female guests we passed eyed him up. The man certainly had the money to take care of himself. I didn’t care how crazy he was as long as he threw a few bucks my way.

  Finally, we the elevator doors opened up and revealed the lavish penthouse suite. As a relatively recent hire, I actually had never been up here before. While the rest of the hotel was a bit shabby looking, management had pulled out all the stops to make the penthouse suite look ritzy. It would take a month’s worth of my pay to book a night in there.

  I followed John into his room. The whole suite was immaculate from its leather furniture to its pinewood floorboards. I couldn’t help but whistle at its furnishings. “Nice place.”

  “Maybe you can book a night here if we hit it big,” John replied, getting settled in. “Now, do you want anything to drink before we begin?”

  I reminded myself I wasn’t here out of courtesy. “I’d prefer it if we got this over with.”

  “A man of action,” he smiled. “I like that. Follow me.”

  Chapter 2

  We entered his bedroom and he pulled out a suitcase next to the bed. He opened it up and revealed that it was full of clothes and various feminine items. The latter ranged from various makeup kits to sultry lingerie. There was even a set of wigs.

  I watched as John placed the clothing on the bed. I wasn’t just going put on a dress and call it a day. The man wanted to completely transform me into a woman. I saw him place a set of bra and panties on the pile. The bra itself was padded to give its user a bust.

  When he finished sorting everything, he fold his arms. “Okay, I need you to strip out of your uniform and put these on.”

  Having second thoughts, I glanced at the door and asked. “Strip?”

  He groaned. “I could always ask one of your coworkers, Ken.”

  I imagined the ten thousand dollars floating away. This humiliation was a small price to pay for that kind of money. “I get the idea…”

  Taking a deep breath, I began undressing before a man I had just met. I quickly reached for the lingerie once I finished taking off my boxers. I would’ve felt embarrassed but John looked businesslike about the whole scenario. This wasn’t as humiliating as I thought it would be.

  It helped that the bra and panties fit like a glove. The soft fabric didn’t chafe against my skin. Hell, the padded bra made me look like I had a nice pair of tits.

  “I knew they would fit you perfectly,” John said proudly. “Now for the makeup.”

  “Makeup?”

  He chuckled. “Don’t worry, I’m a pro at this.”

  Indeed, the man knew his way around a makeup kit. He dolled me up with everything from concealer to eyeshadow. He was careful not to put too much on me. It was just the right amount to bring out my hidden feminine side.

  I was shocked when I saw my reflection in a nearby mirror. “Wow…”

  I didn’t just look like a woman.

  I looked like a drop-dead gorgeous woman.

  The careful use of makeup had brought out a beauty in me I didn’t know even existed. Days of working at a thankless job had made me look gaunt and lifeless. Now, I felt reinvigorated as if I were becoming a new person.

  John wolf-whistled. “Looking sharp.”

  My face looked like I had been instantly teleported to an operating room with an expert plastic surgeon. The blush John had used made my cheek fill out. I gingerly touched my face in disbelief. “Wow, this is real.”

  I saw John rifle through the clothes and take out a beautiful dress. It was a lengthy one piece dress with a rich dark red color. I didn’t have much body hair so the dress didn’t reveal too much of my masculine side.

  I twirled around in it as he watched. “It looks like your size, Ken.”

  Indeed, it fit like it was made for me. It felt a little weird wearing the dress of a dead woman. John was transforming me into his good luck charm in more ways than one. He took out a pearl necklace and a wedding band. “This belonged to Barbara. They’re yours now.”

  I hesitated about taking the jewelry of his late wife. As strange as this encounter had been, I wasn’t eager to cross that line. “You don’t have to.”

  John was adamant. “You’re not my lucky charm without them.”

  I wordlessly took the wedding band and necklace. I put on the ring first and slid it down my finger. It was just the right fit. The necklace followed and perfectly matched the curve of my neck. I felt regal like the Queen of a European nation.

  We finished the look with a pair of platform heels. They weren’t too high so I could walk around them with little difficulty. With the last piece of the puzzle in place, we were ready to depart.

  John did a last minute checkup. He spent quite some time examining my face. “Don’t slump your s
houlders. That’s a dead giveaway. Other than that, you look perfect.”

  I wasn’t as convinced about my new appearance. Sure, I looked completely different but I was still a guy at the end of the day. Any half-drunk person could see through me. Nonetheless, the money was too good to pass up. I’d just have to put and a smile and bear the humiliation for a couple of hours.

  “You’ll knock them dead, Ken,” John said proudly. The man seemed to think I was a real beauty. “Can I call you Ken? It works as well for a girl as it does for a guy.”

  I followed him to the door. “Sure…”

  Saying I was mortified when we reentered the casino would be an understatement. I felt as if ants were crawling under my skin. The fear of being identified by my coworkers made this seem less and less of a milk run. I just needed to keep my head down and pray that no one noticed me.

  Unfortunately, I seemed to draw all kinds of attention. Guests and casino workers all flashed smiles at me. I didn’t know if it was the dress since I got ignored whenever I wore the casino’s uniform. One waiter working at the bar came to me.

  “Would you like a glass of champagne, miss?” he offered. I never imagined a waiter could be so friendly. Usually, you wanted to avoid talking to the guests and doing extra work. “On the house, of course.”

  I forced a smile. “No thank you.”

  When we walked further, John smiled and said. “Looks like you’re a hit.”

  He was right.

  Men were eyeing me with desire. Believe me, it took a lot to make gamblers focus on anything other than the game. I figured it was my dress rather than my face. There was no way I had actually fooled them.

  Soon, a spot opened at John’s favorite slot machine. It was one of those mega-jackpot machines. The payout depended on how long you played and how much money you put in. I didn’t have much hope in John coming out ahead. In any case, this one had two seats so I could sit down without hogging another machine.

  In his element, John rubbed his hands together. “Okay, now it’s time for me to do my part.”

  At the very least, I got some money off of him to order a drink. With some liquor in me, I began to finally relax. Both the staff and guests were quite friendly to me. This wasn’t so bad at all.

  It was funny how a dress and a bit of makeup had transformed me. In fact, it had transformed my opinion of the casino. It was no longer my hated work place. I was beginning to admire its glitz and glamour.

  I couldn’t remember the last time I was so happy to be here. No one was rude or pushy towards me. I could casually walk around the slots and watch John pump in more and more money into those damn machines. I almost felt sorry to bamboozle the man as badly as a slot machine. I was getting paid a small fortune to have a good time.

  If anything, I was attracting a little too much attention from the men. I got hit on quite a number of times. I decided to pretend to be John’s girlfriend and sit beside him. The man was more focused on the game so he didn’t mind. “Here to cheer me on?”

  I watched as reels and numbers lit up on the screen. “How well are you doing?”

  “My combo meter if full,” he replied. The man made it sound like he was playing a video game. It was no wonder he was addicted. “But I haven’t struck gold just yet.”

  I rolled my eyes. “I’m sure you’ll win something.”

  I couldn’t help but enjoy myself. People around here thought I was Ken the sexy gambling companion instead of Ken the boring casino employee. I wondered if this could be a recurring thing with John. While the money was nice, the dress was much nicer.

  Chances were that John would struggle to win a single cent off these damn things. Most players could play for hours without winning anything. Like I said before, they weren’t called one-armed bandits for nothing. He would need his good luck charm for a few more nights.

  Or so I thought.

  “Jackpot!”

  Chapter 3

  Before I could comprehend what was happening, the slot machine lit up like the Fourth of July. The word ‘Winner’ rang from the machine’s speakers. John had won!

  It wasn’t just a small win.

  He had won the Jackpot!

  “Congratulations!” I told him. I was more in a state of shock than he was. My coworkers had always talked about seeing someone win the big jackpot but I never had the chance. “You’ll have to go the counter to cash out a sum that big.”

  The whole place erupted into pandemonium. Guests and gamblers alike swarmed us. The blocked our path until a pair of employees forced an opening through the crowd. Despite my excitement, I knew this was my cue to step aside for a moment. I couldn’t risk any of my coworkers seeing me like this.

  “We’ll cash out,” John said over the loud chatter. I remembered that he was splitting the earnings with me. My eyes lit up like the display on a cash register. “You and me both!”

  I didn’t argue the point. “You go on ahead.”

  John headed to the pit boss to redeem his prize while I slipped away. I didn’t know how much exactly he had won but a mega jackpot was worth millions. Even after taxes, he would be set for life.

  For that matter, I was going to be rich as well. I just needed him to keep his part of the deal. Then, I could take my fee and do home. I’d have a funny story to tell and a lot of money to keep me happy.

  Soon, John came back. “It took a while and I had to dodge a few journalists but I got it all sorted out management.”

  The excitement had died down and the path was clear. When I saw the receipt in his hand, I laughed. “How much?”

  John looked cool as a cucumber. “Five million dollars straight to my bank account!”

  My eyes widened in shock. “Congrats!”

  “The manager wanted me to keep playing with my new earnings,” John said. “It sounds like he wants me to lose it all back to the casino.”

  I chuckled at the anecdote. “It’s the oldest trick in the book. Know when to cut bait when you’re up ahead of the house.”

  “I think my good luck charmed has earned herself a cool million,” he continued, flashing me a grin. The management usually cut a check but registered players could have their winnings directly wired to their account. “Don’t spend it all in one place.”

  The knowledge that I was rich had begun to sink in. “No!”

  “Yes!” he replied with a smile. The man took my hand. “It’s only fair after all you’ve done for me. But first, we should celebrate.”

  A moment ago, I wanted to collect my money and leave. Now, a round of celebration couldn’t hurt. We had pulled off a miracle. More importantly, John had been generous enough to share the wealth beyond our initial agreement. I owed him this at the very least. “Why the hell not?”

  He nodded. “Let’s head back to my suite. I’ll order us some room service.”

  We took the express elevator to the penthouse. John went on and on about how much of a good luck charm I had been. I really hadn’t done much other than sit around and look pretty. It wasn’t too much work considering that I was going to become a millionaire because of it. In any case, I didn’t mind another stay at the penthouse.

  It would give me more time in my new dress. I dreaded taking it off and going back to being a man. My past hour as a member of the fairer sex had been some of the best moments of my life. Perhaps, I could convince John to let me keep the clothes.

  We entered the suite and John ordered us some room service. It didn’t take long before someone came to the door with a full loaded dining cart. “Compliments of the manager. Please enjoy your stay!”

  After tipping the man, John brought in a food basket with a set of glasses. It included a wine bottle, a champagne bottle, various cheeses, and some crackers. There was even an ice bucket for good measure.

  I watched as he uncorked the champagne. The last time I had some bubbly champagne was at the casino staff’s New Year’s Party. That cheap stuff stated like motor oil. I knew the one we had now was the most expensive
bottle on offer at the hotel. The wine was just as expensive with a price tag of over a thousand dollars.

  John poured out a pair of glasses. “Cheers!”

  I clinked my glass against his. “Cheers!”

  The champagne tasted like its price tag. It didn’t take me long to drain one glass and pour myself another. As we drank, John reminisced about his dead wife. “We booked a place just like this for our honeymoon. It was out in Hawaii. Barbara was thankful for the air-conditioning.”

  I placed my empty glass down on the table. “Sounds romantic.”

  “It was,” he said with a soft smile. “This is why I miss our time together at the slots. It didn’t matter if I lost or won. Just sharing the experience with the woman I loved.”