A Long Day Transgender & Crossdressers


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“Try the other ones,” Riley said.

John sighed and plodded back into the changing room to slip on a different pair of jeans. It seemed to him he had been doing this all day, trying on pair after pair of jeans, while Riley judged each by completely incomprehensible standards, considering each deeply for a few seconds, chin in hand, before inevitably dismissing him back to the changing room for another pair.

So it was with some reluctance that he opened the fly of the current pair and began the process once again. Or he had tried to, anyway. To his surprise, he found that they would not come off, held to his legs by some invisible force. He found this odd, but he was more concerned about his algebra test. It was getting late in the day and he would surely miss it if they couldn’t settle on a pair soon. He stepped back out of the changing room, fly open.

“This isn’t working,” he said.

Liam looked up from his newspaper with a mixture of annoyance and amusement, swiveled in his chair behind the desk and replied, “It seems fine to me. It’s just never quite what you want, is it?”

John’s eyes opened to find the couch he had been sleeping on bathed in the uncomfortably blue light of the tv as it blared out a movie he did not remember choosing.

“Fuck, what time is it?” he asked nobody in particular as he sat up. He tried to mentally piece the day back together: he remembered driving Liam home some time around noon, then driving back home, where he had put on the tv as background noise while he considered what to do with the rest of the day. Of course he could have spent the remainder of it with Liam, but if the boy was even half as exhausted as John had been after their extended foursome with Ethan and Curtis, he would probably have passed out just as soon as John had.

What a night, John thought, and morning, too, I suppose. He searched around for his phone to check the time and found it, to his mild surprise, in his pocket. I must have just zonked out immediately, he concluded. To his slightly greater surprise he found had received multiple texts from Riley while sleeping:

hey how was the butt?

good I hope

hope it didn’t break your butthole

These texts were each separated by around ten minutes, John’s phone helpfully told him, and the remainder were sent a few hours after, evidently when Riley had tired of waiting for a response:

free this week

if your butthole still works

hint hint

I mean I want to put it in your butt. tomorrow?

well let me know if you’re still into girls

He chuckled, then responded.

hey sorry I missed your texts

butthole still works, as far as I know

He put the phone down and stretched. Passing out during the day was always annoying in that it meant trying to force oneself back to sleep at a reasonable time. This was of course even worse on a Sunday, with work coming the next day, despite his body’s inevitable objections. Fuck, he remembered, still don’t know what to do about Penny.

A response from Riley temporarily distracted him.

good. still into girls right? at least if they have dicks?

tomorrow?

He found himself smiling despite his body complaining about the couch being a poor substitute for a bed. Sure, tomorrow’s fine he texted back. Just woke up but actually now is fine if you can’t wait.

She quickly replied. wish I could. but work is light this week. hint hint

I gotcha he texted back. Odd that work isn’t light on a Sunday night, he thought, but she’s probably just otherwise busy. He realized he was a little hungry, but, more importantly, that eating whatever leftovers he had in the fridge would provide him another excuse for putting off figuring out how to deal with Penny.

The morning light through his window proved to John to be no less annoying for having anticipated how unwelcome it would be. He had ended up spending the remainder of Sunday night eating, working out, and showering, which had proved to be a sufficient distraction that he hadn’t even begun thinking about work before shutting off his laptop and finally calling it quits around 2AM. Truly, I am a god amongst men, he thought. Surely there’s a Greek god of procrastination, right?

He vowed to look into it on his phone over coffee as he swung his feet over the edge of the bed and began his morning routine. Don’t worry, Johnny boy, that annoying little voice in his head started in. It’s only one more week. Surely a god of procrastination like you can parlay your skills into delaying Penny’s plan to pass out pink slips to everyone and their brother that doesn’t satisfy whatever vaguely defined requirements she secretly has in mind.

Not really the same skill, he mentally replied. I don’t think it’s transferable to another party.

Well, have fun with your firings, then, the voice replied, I hope the layoffs really go well for you.

John grumbled out loud and began his day.

Perhaps it was mostly due to the anxiety he felt on his way into work, but the simple fact that when he arrived at his desk, there was no smartlydressed and aggravatingly y Penny to be found sitting on it made him think, for a few seconds at least, that the day might not be so bad, after all. Maybe with some clever bullshitting, he might even manage to knock the remaining five days down to four without anyone being fired in the name of “efficiency”. In that spirit, he quickly vacated his desk and began the process of acquiring an otherwise unused conference room for his own personal meeting space. This was a handy trick he had used to kill time in other offices. It usually required some form of scheduling, which ate up some time, even before he had begun using the room, usually for very little, and almost always for nothing that couldn’t be done without such a room. But this was, of course, the goal: to waste time doing nothing of value and, especially in this case, separate himself from some manager who would surely wish for something more “productive” to be done with their company’s time.

Having secured the room in the eyes of whatever invisible archons ruled this particular corporate sphere, John set about getting meetings set up to make use of this room. This was usually the sort of task that was best left to email: it would add lag time to the process, which was ideal if one’s goal was, as John’s generally was, to run out the clock. He had decided that the risk of Penny coming by while he appeared unoccupied was far too high, however. This meant that he needed to manually drag people along. Since Priya’s desk was the only one he remembered the position of, he started there, finding her busy typing away at something.

“Hi, Priya,” he greeted her, which seemed to come as something of a surprise to the girl, who practically jumped in her seat.

“Oh, hi,” she said, flashing him a charming smile.

“Oh, hey, sorry, I didn’t mean to startle you,” he fumbled for words. “Could I, uh, see you for a quick meeting?”

She looked at her computer screen with what seemed to John like concern for a second, then turned back. “Sure,” she said.

“If you’re busy…” he began.

“Oh, no,” she said, then seemed to reconsider. “I mean, I’m busy. I’m working. But I’m not too busy.”

“Uh, ok,” he said. “Can we just head to the conference room over there?”

She followed him quickly, which he was fine with; any more time spent in the open than necessary simply risked contact with Penny and he still had no idea what to do about her. When they reached the conference room and had settled in on opposite sides of the table, he closed the door and, happy to see no sign of Penny, breathed a sigh of relief.

“Is this…what did you want to see me about?” Priya asked; her tone was jittery and she seemed to be focusing on her hands, which were hidden out of view under the table.

“It’s uh…” he paused. “It’s actually nothing.”

She looked up with a quizzical expression.

“Actually, I was…can I ask you something?”

She seemed to be even more confused at this. “…Ok?” her answer sounded more like a question.

“What do you think of Penny? I mean, Penelope,” he asked.

She looked away before returning her view to him and starting to answer slowly. “She is a good manager, I think.” If she was trying to hide the fact that she was straining to read John’s face, she was doing a poor job of it. “I mean…she can be kind of…”

“You can be honest,” John said, knowing that such statements never actually worked.

She didn’t respond, but rather bit her lip.

“Look, I’m not here to spy for her or whatever,” he said. “I actually want to know for sure. She seems kind of…”

“Yeah,” Priya said, evidently understanding what John could not comfortably put into words. “She’s very…yes.” She looked around. “Are you going to fire people?”

“Oh god no,” he responded before his brain caught up. “At least I hope not.” She did not seem comforted by that. “I mean,” he said, “I don’t have any plans to fire people. I don’t find that that’s pretty much ever helpful, as much as managers seem to love the idea.”

She seemed to relax at that. “I can be honest, right?” she said.

“Yeah, please,” John answered. “I could use any information you have.” He wasn’t really sure whether that was true, but anything might be helpful, and at least it would kill some time.

“So Penelope,” Priya began.

“Knock, knock,” Penny pronounced the words as she entered the conference room. She stood in the doorframe, clad unsurprisingly in a skirt suit, although this one left far less to the imagination than the others he had seen her in, the skirt barely covering half her thigh. It was also black, though John surmised her closet contained zero tops that were not a shade of blue designed in a lab to accent her eyes.

Priya immediately stopped talking.

If Penny had heard the opening to Priya’s sentence, she gave no indication. “I hope I’m not interrupting this… last minute meeting?” She wore a smile that John did not find particularly friendly.

“Oh, no problem,” John answered. “Yes, I was just getting a few more details that I’d neglected to get the other day.”

“I see,” Penny replied. “Well, I’m sure Priya here has been very helpful. She’s really something, don’t you think?”

“Uh…yeah, she’s been great,” John said. He glanced at Priya, whose expression betrayed that she would rather be anywhere else. “Anyway, I think I got all I need,” he continued, pretending to check his notes. “And I’m sure you’re busy, so how about I let you get back to it?”

“Thank you,” Priya said. She somehow managed not to trip fastwalking out the door.

Penny waited, her eyes following the poor girl out the door, which she then closed before turning her attention back to John. “So, I take it she tops your list?”

“My list?” John said, knowing full well what she was referring to, but lacking any other tactic for stalling.

“Yes,” replied Penny, “You haven’t forgotten already? Or did you perhaps have a particularly wild weekend and blacked it all out?”

“Oh, nothing too wild,” John said. Unless you count taking two dicks up my ass at the same time as ‘wild’, he added mentally.

She seemed to scan his face. “Good,” she said, “then you can accompany me to my office and we’ll go over your results.”

He started to reply but thought better of it.

“…unless there’s another employee here you’re interested in seeing?” she added. He did not know how to interpret the emphasis she had placed on “interested” or even if he hadn’t just imagined it.

“Oh, no,” he replied. If you’re going to sit in here, it’s hardly worth doing, anyway, he thought, consigning himself to dealing with her more directly.

She gave a playful little “hmm,” as a response, then opened the door. “Come on, then,” she said. As he followed her through the maze of cubicles, John could swear he could feel the eyes of the various employees probe him for any sign of what was going on before darting back to their work. It was almost a relief when they entered Penny’s office and she closed the door behind him. “So,” she said, brushing past him to circle around behind her desk as he stood awkwardly, “what have you got?”

“Uh,” he stammered. His stomach was doing somersaults. This was exactly what he had been dreading; the weekend had afforded him the chance to stop thinking about it, and he had joyfully embraced that, pushing this unpleasantness as far out of his mind as possible.

“Nothing, I suppose,” she said, her cool blue eyes cutting through him.

“Well,” he said as he felt the gears in his head begin to grind agonizingly slowly, “after consideration of the multifaceted nature of the work that you do here…”

She raised her eyebrows and somehow this was enough to get the gears to stop turning once again. “Let me stop you right there,” she said. “You know I don’t want to hear more MBA horseshit.”

“So,” he tried again.

“Ranking,” she said, and then after a pause, “What’s their ranking?”

He bit his tongue, took a breath, and said, “It isn’t possible to just rank people.”

She rolled her eyes. “Bullshit,” she said. “It’s very easy.”

Well, this is already fucked, thought John. Might as well just go with it.

“Ok,” he said, “since it’s so easy, why don’t you do it yourself?”

“I’m the boss,” she said. “I don’t do; I delegate.”

“Very convenient for you,” he said. Fuck, that was not the ideal response.

Penny stared at him for a painfully long second in silence, then smiled. “It is, really.” She sat and surveyed her desk for a few moments. “It’s good to be boss,” she said. “But of course it requires a bit of skill.”

“No problem there,” said John.

“Indeed,” she said. “And of course, a boss has to make the hard decisions.”

“I would imagine so,” John replied.

She nodded subtly, then turned her eyes back on him. “And of course, while the boss gets what she wants, she does have to first know what that is.”

“I assume that’s not a problem, either.” John was becoming very aware of the chair in front of her desk that remained unoccupied while his legs grew restless.

“Not at all,” she said. Her tongue played along her teeth.

“And what is it that you want?” John asked.

“A ranking,” Penny smiled.

“I told you, I don’t know how to rank people,” John answered. He gave in and sat in the chair, an action which elicited an expression of slight surprise from Penny, though she quickly wiped it off her face.

“It’s quite simple,” she said. “You certainly do it all the time.”

John could feel his face twist up involuntarily into a quizzical expression.

“I suppose that at least you were being honest when you said you weren’t that clever,” she said, with a small laugh. “Points for that.” She paused for a moment, then continued, “Consider this. Who is prettier, Priya out there, or me?”

John blinked rapidly a few times. “What?”

“You may not be clever, but you’re not that stupid,” she said. “It’s a simple question. Who’s prettier, me or Priya?” She suddenly stood and approached the office window, walking by John. His head turned to follow her as she took a position gazing out the window.

He got to his feet and joined her, following her gaze out to the cubicles on the other side of the glass. Almost involuntarily his eyes searched for Priya’s friendly face, but all he could see was the sea of gray.

“I don’t think…” John began.

“You don’t need to,” she cut him off. “Just answer.” She punctuated her demand by snapping the vertical blinds to the office window shut, shot him an evil smile, and brushed past him once again, this time walking to the only other window looking out on the sea of cubicles. She looked at him expectantly, then snapped those blinds closed as well, throwing the office into shadow.

The light from within the office was still more than sufficient to see, but it did obscure her expression. Not like I could read her, anyway, he thought. “Look, this is…”

“Inappropriate?” she cut him off. “Coming from the guy who by his own admission frequents, what was it again, ‘seedy strip clubs’?”

“That was just a joke,” he said.

“And do you think that joke was maybe inappropriate for your boss?” she asked. She took a step towards him.

“I recall you saying we were, what was it again, ‘off the clock’?” he replied, taking a step back.

“And that means you’re free to just say whatever deeply perverted thing is on your mind?”

“Look,” he said.

She took another step towards him; she now stood only an arm’s length away in the low light. “Just tell me,” she said deliberately. “Who is prettier, me or Priya?”

“I…”

“Just imagine this: we’re at a bar, the three of us, one of your preferred, low class ‘joints’, if you want, and you see me, and you see her, and you decide to approach one of us. Which one is it?”

“Suppose maybe I’m not interested in either of you,” he says.

“Unlikely,” she replied. “Just choose. If it makes it easier, we can substitute Bill for Priya. Or Marge in accounting, or the new delivery boy I know you’ve seen around the office. It’s just a hypothetical.”

“Well, if it’s just a hypothetical,” he said. “I suppose I would probably approach you.”

Her hand snapped out from her body suddenly, causing John to jump back, but he quickly realized she was simply reaching towards the wall of the office, where she manipulated a dial to bring the light level in the room back up.

“See,” she said. “It’s easy. You just ranked me above Priya.”

John let the air he had not realized until just then he had been holding in his lungs out.

“So,” she continued. “Just continue the process. You’ll have a ranking for me before you know it.” She looked into his eyes with a smile on her face that sent a shiver down his spine.

“And, what, I’m supposed to give you a ranking of who I find most attractive?” he asked.

She shrugged. “I didn’t say that. I said you could choose your own system. You’re the expert, after all.”

“Look,” he said, “it’s not so easy. There’s a difference between who’s good at their job and who I want to f…” he stopped himself.

“Go on,” she said. “You were saying?”

“It’s just,” he paused. “It’s more difficult than you make it seem.”

She bobbled her head in a little dismissive gesture.

“And what, pray tell, are you going to do with this ranking?” he asked.

She bobbled her head again in lieu of a meaningful response.

“You can’t be serious,” he said. “You really expect me to produce an ordered list of which employees are most attractive, and you’re going to use that to decide who to fire?”

“I didn’t say that,” she said. “I didn’t say anything like that. Is that what you’re worried about?”

He sighed in exasperation. “To be honest, yes,” he answered. “I don’t want to be responsible for anyone losing their job, especially not based on…I don’t even know.”

She made her face into a little pout that John took to be sarcastic. “You know, for a corporate parasite,” she said, “you seem to be a very good person. Are you a good person, John?”

He had no idea how to reply to this.

She stepped toward him again, bringing herself to within inches of him. He could feel the heat of her body as she craned her neck forward over his shoulder, bringing her mouth next to his ear. “I’m not.”

Words formed on his tongue, but would not, despite his insistence, leave that position. She stepped back.

“Of course,” she shrugged, “like I said, nobody has to lose their job. I just asked you for an assessment of the employees in this department.”

“A ranking,” John tried to correct her as she walked away back towards the desk, but she responded to this with a dismissive wave before turning to face him again.

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