Boiling the Frog Ch. 01

Warning: This chapter contains only flirting, teasing, and character development, but I promise future chapters will get naughtier. Scott is a successful young professional who knows he's a bit--different--but never allowed himself to really look down the rabbit hole. That is, until someone comes along and gives him a helpful shove....

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After a solid 90 minutes of Christmas shopping on a Saturday afternoon in late December, Scott Carson decided he'd earned himself a reward. He'd heard the new Barton Place hotel attached to the upscale shopping mall had a good bar, so he worked his way through the crowds in the lobby to the host stand. His hopes sank as he saw the lounge packed with holiday shoppers like himself.

"Any chance I could squeeze in for a cocktail," he asked the very pretty young blonde as she tapped out a message on her phone. She smirked momentarily then looked up, as if surprised.

"We're full, but you could try the bar in the back," she said disinterestedly. Scott glanced over her shoulder and into the crowd.

"Is it back that way," he asked, motioning to the right.

"Go all the way in and then follow the wall to the left. It's small but you should see it."

He nodded and thanked the girl and then let her get back to her TikTok-ing as he threaded his way through the packed room. The hotel was brand new and lavishly decorated, with the lounge furnished like the interior of a wine cellar, but with a bit of a clubby gothic vibe. Finally he turned a corner and saw a much smaller bar tucked into a back corner that looked like it was chiseled out of solid rock, with stylized neolithic paintings on the walls that looked like they were lit by torches.

"This is weird, but kind of fun," he said, as he touched the wall and realized the "paintings" were actually projected from the ceiling. He could see why this place was buzzy, it was dramatic, and unique. There were groups clustered around high-top tables, noisily getting into the holiday spirit at two in the afternoon (not that he was judging), and he was pleasantly surprised to find the three middle seats open at the five-seat bar in the back of the "cavern." The rightmost stool was taken by a woman with long, sharply-styled deep purple hair, dressed very much like she belonged here, while a well-dressed middle-aged man took up the left flank.

The stool next to the woman appeared empty, and Scott briefly considered taking it, but quickly thought better of it. She was reading a book, and probably wanted to be left alone, and her hair and makeup was giving strong queer vibes. Even if she was interested in men, Scott thought, he probably looked far too conventional to be her type. He sat down next to the man. A few moments later a bartender appeared and handed the man a check. He was young, mid twenties at most, and rail-thin. Scott thought he might be wearing makeup, and his gaze lingered a second too long as he tried to confirm his suspicion in the dim warm light of the bar.

"Would you like to see a drink menu," the bartender asked with a knowing smile, catching Scott off guard.

"Uh, yeah, thanks," Scott said, as the twinky bartender deposited a dark leather folder in front of him. He was definitely wearing foundation, and his eyebrows had more than a bit of a feminine shape to them. Scott looked over the drink list briefly, and the bartender returned a few minutes later to take his order.

"How's the Bouches-du-Rhône," Scott asked.

"It is a rosé, just so you know," the bartender said.

"Yeah, I was looking for something a little different."

"I like it a lot, it actually drinks a lot like a red, but it's a little lighter with more minerality. I can give you a taste." The bartender poured a splash into a glass. Scott tasted it and gave it the thumbs up. "Enjoy!"

Scott took a sip and began scrolling through the to-do list on his phone to plan out the rest of his shopping. The older man had left and it was just him and the purple-haired woman at the bar. He glanced over at her, trying to be as inconspicuous as he could. She might be a few years younger than his 31, and her skintight black outfit hid none of her gamine form. She looked up from her book and over towards him, and he glanced away. Before he could contemplate just how much he might have creeped her out, he heard a slight commotion behind him and glanced over as a gaggle of twentysomething bro types piled in to the opening in the bar.

"So did you fuck her or not," one of them said loudly.

"A gentleman doesn't kiss and tell," replied another.

"Stop being such a pussy," the first one said, drawing laughs from the others, "either that or just hire a hooker, you've spent enough on her to pay for one of the good ones."

"Actually for what Joe's spent he could even pay for one of those chicks with a dick, that's probably what you want anyway," another one piled on, slapping the target on the back hard.

Scott rolled his eyes, mostly in amusement at the display, but also a bit of solidarity with the put-upon one, as he'd been that guy with those friends, once. Ironically all of those friends were now married, living out in the suburbs with a wife and kids--or an ex and a custody agreement--and imagined him living the life of a playboy in the city. In reality his sex life wasn't nearly that exciting, but with a successful career in the tech industry, he'd paid off his loans well ahead of schedule and with no dependents was now starting to enjoy a healthy excess of disposable income at least.

Scott saw motion out of the corner of his eyes and looked over to see the woman leaving her stool, her chunky heels clicking loudly as she strode across the floor. Scott's eyes followed her as she walked towards the bathrooms.

"You can look but I wouldn't touch," the loudest of the bros said to him.

"Why do you say that," Scott replied.

"She's the kind who thinks a man hitting on her is literal rape," he said, "and looks like she shops at the fish counter anyway."

"I don't mind a little seafood," Scott said. "Sometimes appearances are deceiving."

"Well, if you wake up in a bathtub full of ice while she removes your balls to do some witchcraft shit, don't say I didn't warn you."

Scott held up his glass with a nod. The woman returned and resumed her reading, and Scott traded a few more half-friendly barbs with the bros as they pounded their beers and ordered two rounds of Fireball shots. The bartender seemed relieved when they left.

"Another glass," he asked Scott.

"Eh... why not, it's Christmas," he replied, even though he knew he should probably get going. But he didn't have any plans later--the date he'd lined up canceled on him earlier, blaming Covid, but Scott suspected it was more likely due to lack of interest. He'd become fairly good at first dates, but they rarely led to seconds, and those usually led to the friendzone. In fact, he'd largely given up on dating--it was complicated, to say the least--but he'd met this one at a holiday party a couple weeks earlier and they'd spent twenty minutes talking about an exhibit they'd both seen at an art museum, until a voice in the back of his head--actually the voice of his friend Sarah, who'd invited him to the party--told him to ask for her number. Of course, maybe she really did have Covid, he thought, and he could text her again after the new year's holiday. But even if she was interested in him, she was interested in the him that she'd met at the party, and that wasn't the part that held him not so much back as... apart. Not bothering was always the easier option, and he often took it.

His wine was almost finished, and he began thinking about getting the check. He looked to the left, and saw the bartender and the purple-haired woman talking and laughing together like old friends. He allowed his gaze to linger as his eyes traced the woman's profile, especially her long legs in patterned sheer black tights, tall heels studded with chrome spikes, the whole look giving more than a whiff of fetish club vibes. Her hair was shaved on one side, and her eyes rimmed with heavy black liner brought back to a point sharp enough to kill, a look intended to repel as much as to attract. Scott realized it almost certainly wasn't her goal, but he was definitely in the latter camp. The bartender said something that made her laugh loudly--a big, unselfconscious laugh--as he walked away and winked over his shoulder to her. Then, as if she could feel his no longer subtle stare, her head pivoted and her eyes bored right through him.

"You can take a picture," she said with a sneer, "it would last longer."

Scott's brain glitched for an instant and she started to look away. "I like your tights," he said. Where exactly it had come from--the wine, who knows--but something had possessed him to say exactly what he had been thinking at that moment.

"What?" Her expression seemed more curious than annoyed.

"I said, I like your tights."

The woman cocked an eyebrow his way, then looked away and crossed her legs, then bounced one of her shoes on the end of her toes. She ran her hands along her leg, as if appreciating the feel of the sheer nylon, then gave Scott a sideways look.

"They're Wolford," she said. "There's a boutique on the third floor, they should have them in your size."

Scott smiled back. She seemed to expect this to shock him, but instead he turned slightly in his stool then leaned forward and pulled up his pant leg.

"I know," he said, revealing the same distinctive pattern in matching sheer nylon on his own leg.

"Oh," she replied, like someone pleasantly surprised. "Why don't you come over here so I can take a closer look?"

She motioned to the stool next to her and Scott relocated himself, bringing one leg up across the other and pulling back the cuff of his grey chinos. She reached down as if to touch and paused just short. "It's OK," he said, and she wrapped a hand around his ankle then slid it up his leg, sending a tingle up his spine.

"Did you shave?"

"This morning," he replied.

"Are you wearing anything else," she asked.

"No, just these," he replied.

"Why?"

"I just--I like how it feels."

"They do feel nice," she said. "Put your leg down," she said, and turned slightly to face him more closely as he rested his foot on the stool. He had no idea where this was going, but following her lead seemed like the best idea. He heard a slight thump on the ground, and a moment later his eyes widened as she felt her stocking foot brush along his ankle and feel its way up his leg.

"Do you only dress under your boy clothes?"

"Well, yeah, I mean, at least outside of my house," he answered.

"Why? Is it just a fetish for you?"

"I--I don't know," Scott replied. "I guess like how it feels, but I don't like how it looks."

Scott looked away as she continued to measure him up.

"You shouldn't feel shy," she said. "You'd look pretty in a dress."

Scott felt a surge of emotion rise within him. "I guess I've never felt that way."

"No, look at me for a second, I want to look more closely," she said as she looked at him the way a doctor looks at a patient, nudging him left and right with a finger on his chin. "You might be surprised what some makeup can do. You might not be the next femboy porn star like Alex over there," she said, nodding towards the bartender, "but a lot of your features are on, like, the softer side of male, like you don't have huge boxy shoulders or a really square jaw--no offense."

Scott's mind swirled at how rapidly things had escalated, from the casual mention that the bartender was some kind of porn star to the fact that he was sitting here, talking with an intimidatingly gorgeous woman who he'd just barely met, about one of the deepest and most shameful secrets in his life, that he'd kept from almost everybody except a couple of girlfriends who gently dumped him shortly thereafter.

"Are you trans?"

"I guess I don't really know. But like, I've just always wanted to know what it would feel like."

"To be a pretty girl," she said.

"Yeah," Scott said, his gaze off in some faraway place.

"And you've never tried, really?"

"I mean, I've gone out like once or twice for Halloween, like really bad-"

"And you really liked it," she said.

"I mean," Scott replied.

"Be honest."

"I had fun."

"But that's it?"

"Yeah, I mean, I've dressed up at home, and I look in the mirror and just feel kind of ridiculous. I've bought some makeup, but the one time I tried it, I looked like a deranged raccoon."

The woman laughed. "You should have seen me in junior high. Hot mess."

Scott smiled and the woman took a long pull on her drink.

"I could show you," she said.

"Show me-"

"Doll you up a little," she said, "slap on a little warpaint, hold up a mirror, you look and go all like 'holy shit.'"

Scott blinked several times as his brain tried to catch up.

"Um, I mean I guess, maybe sometime?"

"Right now. I live upstairs."

Scott blinked again. He wasn't expecting either of the things she said.

"Are you surprised?"

'Rich parents,' Scott thought. 'Or a renter. Maybe that's the answer? But even renting in this building costs a medium fortune.'

"I--I don't mean-"

She let him off the hook. "It's OK, I suppose I don't look like some middle-aged tech exec. But enough questions. All you need to know is I live alone and I can assure you I only hurt people who ask very very nicely."

The mischievous gleam in her eye was irresistible.

"Well, I guess I can--I can finish my shopping later," Scott said.

"It's a deal then," she said, sealing it with a delicate handshake.

"I should just close out my tab here," Scott said.

"Oh, don't worry--Alex?" The bartender stopped and looked her way. "We're closing out, you can put it all on mine."

Scott blushed, and couldn't shake the feeling that he was the one being picked up. Not that he objected.

"Thank you," he said.

"You kids have fun now," Alex said as he brought the tab over, then looked directly at Scott. "And I'll be here until 11 if you want to come back and tell me all about it." He winked at Scott and then picked up the tab and sashayed away.

"He is--a lot of personality," Scott said, shaking his head.

"A filthy, filthy man," she replied. "But a heart of gold too, and I don't just mean from all the old rich men who pay him to suck his dick."

'You're in way over your head,' Scott thought.

They walked out of the crowded restaurant and through the lobby, to the separate elevator bank that served the private residences in the tower. An older man behind a desk smiled as they approached.

"Good afternoon, miss," he said.

"How are you, Edwin," she said, the question sincere.

"Busy busy, Christmas you know!"

"Well good luck," she replied, and they entered the elevator. The door closed, and she hit the button for the 13th floor.

"I don't even know your name," Scott said.