Chapter 1: The Auction
I'd been looking forward to attending this year's annual LGBT charity fundraiser, not only because it would give me the chance to mingle with many long-lost friends and colleagues, but also rub shoulders with some of the city's most notable celebrities and politicians. The mayor would be there of course, but also plenty of famous athletes, musicians, and movie stars. As I slipped on my clingy silk ball gown and Christian Louboutin heels, I angled my body sideways to examine my figure in my full-length wardrobe mirror.
Not too shabby for a thirty-five-year-old, I nodded to myself.
My natural breasts stood high and plump behind my plunging neckline, and my butt was still round and firm against the outline of my gown. Even my larger-than-normal boy-cock was nicely concealed behind the thigh-high slit of my dress from my tight-fitting compression underwear. I was curvy in all the right places and excited to see who I'd have a chance to meet at the swanky gala. It had been too many weeks since I'd been on a proper date, and I could feel my pussy throbbing at the idea of hobnobbing with all these glamorous guests.
I gently placed my Swarovski pendant around my neck, then glanced down at my glistening cleavage under the bright lighting of my walk-in closet. It was a far cry from a real diamond necklace, but something told me not many people would be staring that far up my exposed chest anyway. With flushed cheeks and a wide smile, I headed out the front door of my condo when I received a text notification that my Uber ride had arrived to pick me up.
When I got to the Ritz-Carlton hotel, I walked up the granite entrance steps and noticed a sign in the corner of the lobby pointing toward the gala being hosted in the Grand Ballroom. As I approached the closed doors of the room, I could already hear the buzz from the voices of those who'd arrived early, mixing with the sultry sound of soft jazz emanating over the speakers. I presented my entry pass to the doorman, and he opened the door, waving me in. When I entered the room, my eyes widened at the size of the crowd, with well over a thousand well-dressed guests mingling and laughing in small clusters under the sparkling chandeliers. I felt a little awkward and exposed standing there all by myself, and I grabbed a flute of champagne from the silver tray of a passing waiter, quickly gulping it down.
"Shae!" a familiar voice said as someone caressed her fingers over the small of my back from behind. It was Jade, my friend and occasional lover, who I'd met at one of the cabaret shows I performed in.
"Jade!" I said, turning around to give her a big hug. There weren't many people I'd feel comfortable greeting in such an overt physical way, but I'd had enough hot and heavy makeout sessions with Jade to ease any inhibitions I might otherwise have. "It's so good to see you! How long has it been? It seems like ages–"
"I know," she smiled. "Fortunately, I have a pretty active imagination that allows me to relive our many moments together and remind me of you on lonely nights..."
"Don't get me started," I laughed, crossing my legs uncomfortably. "I'm already having a hard enough time keeping my dick in my pants around all these glamorous celebrities and movie stars."
Jade glanced at the high slit in the side of my dress, peering at the curvature of my exposed thigh protruding from the gap, and grinned.
"Well, if you need any help with that, let me know," she said. "Because it doesn't look like I'd have too much trouble massaging that big thumper of yours if you need some temporary relief. We can steal off to the ladies room for a quickie any time you're ready. I've missed playing with that beautiful joystick of yours. My plastic dildos just haven't been doing the job for me lately."
"Stop already!" I groaned, moving closer to her to hide the growing bulge in the lower part of my dress. "I'm trying to act like a lady tonight. I don't want anyone to know that I'm carrying a concealed weapon, at least until later in the evening when I might be lucky enough to catch the eye of one of these superstars."
"Well you're certainly a full-blooded woman as far as I'm concerned," Jade smiled, kissing me softly on my cheek. "You just happen to have a little extra equipment that makes you even more desirable."
"Thanks, sweetheart," I said, glancing around the room to see if I could recognize anyone else I knew. I immediately noticed the flaming red hair of the emcee at my cabaret revue, Ginger Snaps, standing in a small circle with a few of the other female impersonator performers from my troupe. She motioned for me and Jade to join them, and we ambled over in their direction while I discreetly pressed my flaring prick back between the folds of my dripping pussy.
"Hey beautiful," I said when I reached Ginger's group, giving her two kisses on the cheek. "What brings you to the other side of town? This is a long way from our little cabaret club, both geographically and metaphorically. This isn't exactly our usual type of crowd."
"Are you kidding me?" Ginger said, placing her hands on her hips. "This is the biggest LGBT party of the year. I wouldn't miss it for anything!"
I peered toward my troupe of fellow 'Lips' performers, glancing at their over-the-top female impersonator costumes.
"Hey guys," I smiled. "Glad you could make it. Do you remember my friend, Jade? She's been to our shows a couple of times–"
"How could we not recognize the prettiest girl this side of Chicago?" one of the performers with the stage name Lola said, holding out his hand to greet Jade warmly. "But go easy on the 'guys' comments–we’re trying to stay in character for the duration of this little shindig."
"No worries," I chuckled. "Your secret is safe with me. I'm sure no one would even suspect you're anything other than the glam queens you already are."
"It's a little harder for us than it is for you," Lola grumbled, nodding toward the rest of the group, who were staring at the wide slit of my skirt that exposed my tall, slender legs. "You've already got most of the natural endowments to create the persona. The rest of us have to use lots of strategically placed padding and makeup to look like real women."
"All the endowments except one," I laughed, nodding toward the bulging crotches of my friends. "I still have to conceal certain parts to complete the act."
"It's a shame too," one of my other colleagues named Roxy said. "We've seen you undressed. It's too bad you save that pretty poker only for your private affairs. I'm pretty sure I'm not the only one of us who's fantasized about jumping into your deep end."
"That's sweet of you to say, Rox," I said with a lopsided smile. "But you know how I don't like to mix business with pleasure. It would ruin the special chemistry between us that makes our show such a big hit."
"I suppose so," Roxy frowned. "Just let us know if you want to branch out sometime..."
"Speaking of branching out," Ginger said, interrupting our awkward conversation. "We're going to be auctioning off some special prizes later in the evening. I don't suppose you'd like to volunteer to be one of the date-for-a-night prizes? It's for a good cause after all–"
"What do you mean, we?" I said, peering at her with pinched eyebrows. "Are you one of the organizers of this event?"
"I'm the MC," Ginger said, nodding her head. "And you'd be a perfect catch for one of these rich celebrities. It's mostly just for show, anyways. They'd be buying you only for one night, with no strings attached."
"I dunno, Ginger," I said, crossing my arms over my exposed bosom. "It's one thing to vamp it up on stage and quite another to go home with the customers. I've never felt comfortable crossing that line..."
"But I understand you do make the occasional exception," Ginger winked, smiling toward Jade. "I imagine it wouldn't be the first admirer you've mixed with outside your professional circle."
"Who I mix with outside of work is my business," I said, clasping Jade's hand and moving in front of her to make it clear she was off-limits when discussing my private life.
"It's okay, Shae," Jade smiled, rubbing her hips softly against mine. "Ginger has a point. It would just be an innocent date and nothing more. Plus, you'd be raising money for a good cause. You can walk away any time you wish..."
I paused for a long awkward moment, staring at Ginger and my fellow cabaret performers, feeling uncomfortable and flushed.
"Come on, Shae," Lola smiled. "We know you like to flaunt your stuff. You're a natural at this. Besides, don't you want to know how much you're worth? You could raise thousands from a simple date."
I shook my head, exhaling heavily, then the rest of my band encircled me, clasping my hands while they sashayed their hips in synchronization.
"Shae, Shae, Shae!" they chanted in unison.
"Free your mind of doubt and danger," they crooned, reprising the Spice Girls' song 2 Become 1 from our cabaret show. "Be for real, don't be a stranger..."
"Fine!" I stammered, laughing out loud with my bandmates. "For one night only, I'll make an exception. But no sex. It's just a simple date for a good cause."
Ginger nodded, peering around the room at some of the eligible bachelors eyeing my curvy figure from afar.
"Don't close all your options too fast," she smiled. "You never know who might choose you for his date. This could be your chance to really spread your wings–"
"Not to mention a few other things," Jade said, noticing just as many women staring in our direction. "It could just as easily be a pretty actress or a glamorous rock star..."
