Bet Her Not

Greetings everyone, happy Friday.

Today's cap got a bit long, so I'm just posting it as text like last week. Silly little transgender caption this time, hopefully you all enjoy it. It used an idea I had for Chief Executive Bimbo but didn't use. Though I might use it again in part 3, if I can ever get back to writing it.

Anyway, without further ado:

“Dammit Jenna, the lockdown was one thing, but--”

“But nothing, Tiffani,” his roommate chided, unable to stop grinning at his obvious discomfort. “Now, hurry up, we're going to miss the carpool.”

Timothy Wiffeneve, or Tiffani as he'd been called these last few months of working from home, tried to glare at her, but the recent botox injections just left his face stuck in the permanently confused expression he'd been seeing in the mirror for the last two weeks. He sighed, and finished applying his makeup, as Jenna hogged the sink.

“I've lived like a woman since March,” he began, barely fighting an urge to stomp his heeled foot. Jenna had insisted on feminizing his body language, and weeks of training had made the motion second nature. He slid the lipstick cap back on, smacking his lips once in the mirror. “But I can't go back to the office looking like this! Even if security lets me in the building, my boss will have a conniption fit--”

She rolled her eyes, finishing combing out her long hair. “For fuck's sake, Tiffi, did you not read the message from Human Resources this morning?” He started to reply, but she held up a hand, stopping him. “Nevermind, I forgot you lost phone privileges after that stunt at the salon last week. Here.”

He winced, reminded of the horrible incident. His groin still burned from the waxing.

He followed her into the living room, where she pulled his phone out of her purse. He blinked in horror. 

“What did you do to my phone?!”

She glanced at the device, as if not understanding why he was so shocked to see it. “Huh? Oh, I figured you were due for an upgrade. The guy at the store was very helpful, let me customize it and everything.”

He took the phone gingerly, unconsciously careful not to damage his long plastic nails. The device was hidden inside a massive, bright pink hard cover, the case further covered in red-and-white glitter-coated hearts.

It looked like something a teenage girl would own, not a thirty year old man. Not even one decked out like a woman.

He touched the screen with his thumb, then frowned as it refused to unlock. “How--”

“Oh, these new models have a facial lock,” Jenna said, pulling a compact from her purse and checking her own makeup, nonchalantly. “Just look into the camera and make your best 'O' face, Tiffi.”

He gasped at her in shock, only for the phone to blink 'Wrong Facial Password'.

Shit! He winced, then sighed. Well, fuck it, I'll get this over with and just reset the damn thing. Surely it can accept thumb prints too....

He opened his mouth, making a ridiculous circle with his lips. His face appeared on the screen, a red square forming over his image. Only when his lips pursed enough to hide his teeth, did the square blink green, unlocking the phone.

“Don't bother trying to change it, either, dear. The boy at the phone store was nice enough to lock the settings for me.” She smirked over the top of her compact's tiny mirror. “Only cost me a blowjob. Now that I see your reaction; it was totally worth it.”

Timothy glared at her, then tried swiping the screen, careful not to put any pressure on his nails. They took ages to fix when they popped loose. “Hey, it's not working.”

“Huh? Oh, sorry, the case window is too think for the touch screen to work easily, so I had it disabled entirely.”

He sighed. “Then how the hell am I supposed to use the damned thing, Jen?!”

She just smirked again, a look he'd grown to hate since he lost the bet and his life was turned upside down. “Easy. The camera facial system is always on. If you want to swipe, just look at the screen and shove your tongue in your cheek, Tiffi.”

His mouth fell open, in horror. But he could tell she wasn't bullshitting him. Fuck!!! He looked at the camera, gulped, then shoved his tongue in his cheek. Only when the bulge was as large as he could make it, did the screen start slowly cycling through his apps. He went too far, and had to shove his tongue in the other cheek to get it to go back to the right app.

He nearly touched the Message icon, before remembering, and looked back at his bitch of a roommate. “ App functions are sound-based. Just a light moan to open an app, dear.” She winked evilly. “A gasp to close. A squeal to-- well, I'll leave the rest for you to find out on your own. I'm sure it'll be loads of fun to watch you experiment.”

Timothy groaned, only for the phone to relock. “Dammit!” He did his 'O' face again, then tongued his way back to the Message icon, and moaned. It took several humiliating tries before the app finally opened, and he wasted far too long trying to figure out how to resort them, before giving up. He spent a moment tonguing his way through his messages to get to the newest ones at last.

A final moan to open the message, and he began to read, horror filling his voice. “HR Memo to all employees of Gerson Industries LTD returning to routine office work as lockdown ends: Effective Immediately, sales representative Timothy Wiffeneve shall be referred to by all employees as Tiffani Wiffeneye, per her new status. All employees are required to address Miss Wiffeneye using her preferred pronouns of her, she, miss, babe, doll--!!!”

He couldn't finish reading the memo, nearly hyperventilating as the ramifications hit him. He couldn't bear to see what more the department had sent out, but clearly his job was about to become far worse than the humiliating experiences of the last few months.

“Oh good, they didn't forget the 'Y',” Jenna chortled, taking the phone from his hand before he dropped it. A loud honking sound boomed from outside. “Ah, and there's the carpool, right on time. Let's get going, wouldn't want to be late to our first day back to work, would we, Tiffani?”

Too stunned to speak, the feminized man could only stare at the phone in her hand.

“Oh, don't look so glum, Tiffi.” Jenna sighed, pushing him toward their apartment door. “Okay, I'll tell you what. You beat my sales record this quarter, and I'll let you skip out the rest of our bet. That's nearly six months early.”

Timothy blinked, finally snapping out of his shock. His sales had been skyrocketing all lockdown, though he hated to admit it. Jenna's insistence that he use a feminine tone on the phone calls had almost certainly been a major factor in his higher sales. I could win this, I've had my best month ever.

He didn't want to add to his bet, but getting out of the last one so early. He might only have to spend a few weeks at work as a woman!

“Okay, you're on--” he started, but Jenna continued, cutting him off.

“Of course, if I win, then those silicone falsies of yours are getting replaced with a real set. And I'm not letting you stop at those pathetic B-cups, either, Tiffi. You are getting a real set of jugs, babe!”

He gulped, but nodded, desperately praying her sales hadn't been booming too.