Work Desperation (2)

Hello dudes and dudettes,

here is the second caption of a new series commissioned by niceagent42.

Everything seems to be fine with the Meek siblings, but what is that? Luke the creep knows about Hannah's real identity.
What is a feminized guy to do if he does not want to end up in prison?

Well, find out in this new caption!

I hope you all enjoy this 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 ---

"Ok, I get that I have to dress as a woman, but why does this skirt have to be so short? It just barely reaches mid-thigh! And why do I always have to wear heels?" Harris complained to his sister as he saw his outfit for the day.

"Ugh, really, again with this?" Holly just responded with annoyance. "You have been a woman at work for a month now, and you still complain about it nearly every time it is time to dress!"

"Well excuse me, but I am the GUY that has to wear WOMAN'S clothes, not you. So I can complain all I want!"

"You can just quit anytime you want, right?" was the deadpan response Harris got. "Just put in a notice so it doesn't look bad on me, alright?"

"Oh, trust me, I will be out of there once I have enough money to get my name cleaned again!"

But that was still a bit away, so with more grumbling and complaints Harris started his transformation into the secretary called Hannah.

He undressed himself before sliding a pair of pink panties up his smooth well-shaven legs which were followed by a sheer black pantyhose that he rolled up.

Next he grabbed some breast forms that his sister got him after his first day at the office "so he looks natural", and with a sigh, he slathered them in glue before attaching them to his chest.

Once the glue dried he just turned his back to his sister and motioned for her to come close.

Said sister just rolled her eyes, before grabbing a corset, wrapping it around her brother's waist and starting to pull, slowly making his waist smaller and smaller, inch by grueling inch.

"You know, it is good that you just got your first paycheck" Holly said as she tightened the laces. "Because now we can finally shop for some fitting clothes for you!"

"Clothes?" Harris questioned with ragged breath as the corset got tighter and tighter.

"Yes, clothes. You have to get some of your own, you can't just use my hand-me-downs all the time, you know?"

"But that will cost so much money! I want to get out of this situation as fast as possible!"

"It is not that much, you drama queen. Just some cheap skirts and blouses, maybe a blazer, some pantyhose and heels, so maybe 400$ total. Or you can keep using a corset to fit into my clothes."

Harris only grumbled in agreement, seeing his sister's point, as she finished lacing up the corset.

Once his waist was small enough Harris grabbed a black bra and pulled it over his chest before pulling a black long-sleeved wool shirt over his torso, which was quickly followed by a pink skirt that barely reached mid-thigh being added.

The last piece of the outfit was a pair of glossy black heels that he now could walk in without any problem thanks to a month of daily training.

"So, do you want me to do your make-up?" Holly asked her brother once his outfit was done.

"Nah, better not. If I have to be like that I think it is high time I learn to apply it myself".

And so he sat himself at the vanity table, and just like his sister always did he began by adding foundation to his face, which was quickly followed by some blush around the cheeks.

Next he grabbed some natural eye shadow, painting his eyelids, before he took some pink lipstick and covered his lips just enough to be noticeable.

The final piece was a chain necklace which he clasped around his neck before he took an iron and straightened out his naturally long brown hair.

"So, how do I look?" Harris asked his sister, hoping that he did everything alright.

"Hmm... Your lipstick is a bit smudged, you used a bit too much blush, and maybe you should outline your lips more. But other than that you did fantastic for your first time. Or maybe you did some practice runs beforehand?" his sister answered with a smirk and a wink.

"Not really. Just watched what you did over the last month alongside some tutorials on the internet" he replied, making his sister send him a genuine smile of appreciation.

"Well, I am glad to hear that you take this seriously. I don't even want to think about what would happen if somebody finds out. Now, how about we head off to work?"

And with that the siblings were off to work, not knowing that the day will have a nasty surprise for them.

It began after hours when everybody besides the Meek siblings left the building. Holly was writing some reports in her office while Harris was filing some documents in the printer room when Luke came through the door.

"Oh, hey Luke" Harris said in his best female voice, even though his voice was frosty as he talked to the creep that always bugged his sister.

"Don't worry, I was just about finished. You can have the room for yourself" he continued, but as he was about to leave Luke moved in front of him, making Harris narrow his eyes.

"Oh, you can stay, Hannah. Or should I say Harris?" Luke said with a smirk, making Harris's eyes go wide in shock as he dropped the documents.

"Oh yeah, I know who you are. Can happen when you use your social security number. And I have to say I am quite impressed that bitchy Miss Stickler-for-Rules would do something like that."

Harris could only grit his teeth as he saw Luke's shit-eating grin. "What do you want, Luke" he spat out, now using his normal voice as rage started to bubble as he heard Luke slander his sister.

"Normally I would want nothing, I would probably even applaud your sister for sticking up for her brother like that, and you for going through all this. But thanks to your sister I am more inclined to just report you. Who knows what they will get you for. Maybe fraud? Or social security scam? Or maybe corporate espionage?"

Harris began to ball his hands into fists as his whole body began to tremble as Luke listed off what he and his sister can be charged for, but before he could say anything Luke continued.

"Or maybe I could keep it for myself. For a price, of course. You know I am kind of lonely without a girlfriend to keep me company. And maybe you can help me out there."

"Hell will freeze over before I let you anywhere near my sister, you creep" Harris spat out, not caring about the consequences if it means keeping his sister safe, but Luke only laughed.

"Oh, trust me, I don't want anything from Miss Frosty Bitch anymore. No, I want YOU! You are way cuter than her. So what do you say? Wanna be my obedient little girlfriend?"

Harris was once again shocked to the core when he heard that Luke wanted him instead of his sister, but he also knew that he could not be the reason his sister loses her job or worse.

"Fine, you win. I will be your girlfriend..." he said instead in a subdued voice, his shoulders falling as all fight and anger left his body, now replaced by distress and despair.

After all the only other option was to tell the creep to take a hike, but that would only worsen his record with the police and put his sister down the same path, ruining her life, all because she helped him.

"Good, I am glad that you are smart. Well, not smart enough to hide your social security number, but at least smart enough to realize when you have lost" Luke began to say with a snicker.

"Now here are some rules that you will have to follow for this deal:

1. You have to make it look to others like you have fallen head over heels for me.

2. Nobody can know the truth, not even your sister. You will say this relationship was your idea.

3. You have to show utter submission and adoration for me, alright?"

Harris could only nod, knowing there was nothing he could do.

"Good" Luke said before he started to unzip his pants and let his rock-hard dick fall out.

"Now you can show some of that adoration by getting on your knees and worshiping me like the male I am!"

With tears in his eyes Harris slowly lowered himself to his knees, crawling forwards until he was face to face with Luke's crotch and hesitantly started to open his mouth.

Luke, who thought this was taking way to long, just grabbed the back of Harris' head and started to piston himself in and out to the feminized guy's shock and disgust.

"Fuck, that hits the spot baby!" Luke groaned as he kept going. "By the way, you should invest in some sexy dresses and lingerie. I want you to look pretty for our future dates after all! Also I like big boobs, those mosquito-bites of yours are laughable! So get some bigger falsies, the bigger the better!" Luke demanded as the wet smacking sounds of lips hitting a pelvis over and over again filled the printer room, with Holly continuing her work none the wiser.