Work Desperation (1)

Hello dudes and dudettes,

here is another caption for you all to hopefuly enjoy!
This is a new series, commissioned by niceagent42.

This time around a poor sap can't find a job because of past mistakes. And what do you do when you can't get a job as yourself?
You simply turn yourself into a woman with the help of your sister, duh!

I hope you all enjoy this new series, and hope you are ready for more, because there is more to come!

But until then stay happy and healthy, and I hope to see you all next time.

--- Text ---
The current job market was a cruel one, something that Harris Meeks quickly learned first hand after he tried to get a position for months now without any success.
Of course having a criminal record because of drug possession after he was caught smoking pot in the park by police nearly a year ago did not help him either.
To add insult to injury just 2 months after his charges weed became legal in his state, but by that time it was already too late.
Now Harris wants nothing more than to hire a lawyer to get this injustice expunged from his records, but with no money he needs a job, which he does not get because of his criminal record.
And so the vicious cycle continues until one day Harris was desperate enough to ask his sister for help.

"Please sis, you really have to help me out here. I know that I was not the best person, but I seriously want to turn my life around" he begged her the same way he did for days now.
Meanwhile Holly Meeks, his older sister by one year and a mid-level manager for NA Corp., just looked at her brother before letting out a sigh.
"Maybe I can help you, Harry" she said before quickly holding up her hand to stop her brother from overreacting before he heard the whole deal.
"Our company has some open assistant positions, and I think I can get you one. But I am tasked to diversify our department, so you will have to work as a woman. That is the deal."

After hearing this Harris wanted to flat-out refuse, but then he took a few seconds to think things over and quickly realized that he had no other options left.
"Ok, alright. I will do it. But only until I can afford a lawyer" he agreed, letting his shoulders fall in defeat as he did so, making his sister smile.
"Great, I will make the necessary calls then, until then you go upstairs and shave yourself. Can't have an office girl running around with hairy legs after all. And make sure to use my shampoo!"
With that Holly took her cell phone to get the necessary paperwork done while Harris was left to go upstairs and prepare himself for things to come.

Once in the bathroom, he unclothed before stepping in the shower where he began to use the razor and shaving cream of his sister, and once he was hairless from head down he started to shower himself, making sure to use the shampoo as Holly instructed.
Once done he was left with baby-smooth skin, while his long brown hair that ran down to his lower back was now silky smooth and smelled like peaches.
Just as Harris was done toweling off his sister came into the bathroom, carrying a bunch of female clothes alongside a corset in her hand.

"Wow, you could really pass as a girl if it was not for that thing dangling between your legs" she giggled, making the brother only grumble in response.
"Will this thing really be necessary?" he asked, ignoring her previous remark while pointing at the corset with a frown.
Holly just apologetically shrugged her shoulder. "These are some of my old clothes, so they will be a bit tight on you, but without a corset, they won't fit at all. So unless you have your own skirt and blouse we will have to use the corset for now".
Harris just sighed, before turning around, accepting his fate, and letting Holly put the corset around his waist before pulling it tight, robbing him of some of his breath.

Once that was done Holly grabbed a pair of panties and handed it to her brother alongside some sheer stockings, and Harris began to pull them up his legs.
Afterward came a black bra with some slight padding and a pleated black blouse, before the outfit was finished by a gray skirt and some black heels that were new for Harris to walk in.
"Well, you nearly look like one of the office girls already. Just have to work some of my make-up magic and we are ready to go!" Holly said, excited about how well her brother looked as a female.
"Wait, ready to go where?" Harris replied, his face scrunched up in confusion.
"Well, the paperwork is done, just have to get the info into the system and you are officially part of the team! Congratulations! Now I just have to introduce you and show you around the office."

Harris was shocked that everything went so fast, but before he could say anything further Holly whisked him away to the vanity table where she did his make-up.
She began by plucking his eyebrows, putting them into thin arches, before covering his face in foundation and applying some light pink lipstick to his lips.
After that she only did some light eyeshadow, but nothing more as she did not want to make Harris stand out too much from the other female workers at the office.
"Well, we are done, and I have to say I did a very good job, don't you agree?" Holly asked her brother, showing him his image in a mirror, and Harris could only nod dumbly.
He could not believe how much he looked like a girl, and he had to admit that maybe, just maybe, he felt attracted to his own female version.
"Now enough staring at how pretty you are, Hannah" Holly snarked, making Harris glare at his sister, but she ignored it. "We have to go and get you introduced!"
And with that Holly grabbed her brother by the hand and dragged him after her to the office, with Harris stumbling alongside her in his unfamiliar heels.

At the office Holly just made Harris sign some paperwork to make everything official, and after that the next few hours were spent getting introduced to the whole department.
And while at first Harris was shy and nervous, believing that he would get found out any minute, he soon gained more confidence as he realized that nobody was able to tell his real gender.
After that everything went smoothly, until Luke Dixon, one of Holly's employees, went to grab and sort her paperwork like he always does, and while doing so found "Hannah's" application.
"Wait, isn't that the new chick" he wondered to himself as he began to feed the info into the system. "Wonder what she did to get hired so fast. Probably because she is the sister of Bitch-Queen Holly. Or maybe she took one or two of the CEO''s for a ride. But I can't really blame them with such an inviting piece of ass..."
While he began to think about his boss and crush Holly, who until now has harshly declined any of his "charming" advances, he came around to check Hannah's social security number.
But when the screen displayed "Harris Meeks" all of Luke's thoughts came to a halt as a sinister grin started to grow on his face, especially when he saw the documents where all signed by Holly, who was also written as the recommendation.
"Well well well, looks like little Miss Meeks has some dirt on her. I bet I can use that for some favors..." Luke thought as a plan began to hatch inside his mind.