Work Desperation (3)

Hello dudes and dudettes,

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

Looks like Holly got a new sister now. If only "she" could have found a better boyfriend.
And why does Holly got this weird feeling in her gut when she should be happy her brother found his real identity?

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.

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"I still can't believe how much Harris has changed the past few weeks" Holly thought to herself as she was sitting behind her desk and finishing the last reports for the day.

And indeed she could not believe it, ever since he got his first paycheck it was like her brother Harris was a completely changed person.

Instead of saving money for the lawyer he wanted so he could get rid of his criminal record he suddenly started to spend most of it on new clothes.

Now of course Holly thought it was a good idea at first, after all as a secretary he needs more than a single outfit, but Harris bought a lot of everyday clothes, dresses and even nightgowns.

And Holly's disbelief and confusion did not end at this behavior, as just 2 weeks ago she overheard her brother sobbing as he was taking a shower after a long day at work.

She immediately got concerned, not knowing what could have gotten her usually strong-willed brother in such a state, and when he left the shower and got dressed she immediately confronted him.

But instead of an answer Harris just walled himself off, at first stating that she must have misheard, but she got more insistent he got annoyed.

"Look, there is nothing wrong with me, alright? So just leave it be" he gruffly answered, leaving her more confused and slightly hurt that her brother apparently did not trust her with his problems.

After that encounter at first she thought that maybe he was starting to have troubles or second thoughts about working as a woman, which just made her worry more.

At one point her anxiety about her brother's situation got so far that she decided it would be best if he quits, and that she would work overtime and just give him the money.

But when she went around the office searching for Harris to tell him the good news Holly finally found out why exactly her brother was crying in the shower days earlier.

Because when she got around the janitor's closet she heard strange noises and decided to investigate, and low and behold there was her brother, pressed against the wall and Luke pistoned his cock in and out of his ass like a man possessed.

The sight shocked Holly, and after a few seconds she closed the door again, a relieved look on her face.

"Wow, I never thought that Harris was like that" ran through her mind as she made her way back to her office. "This of course explains quite a lot".

Holly shook her head to snap herself out of her daydreaming and continued to finish the reports that were due tomorrow.

"Well, I am happy for Harris. I would have never thought that he wanted to be a woman" she said to herself with a smile, but then a knot formed in her stomach.

She frowned as she felt the queasy feeling in her stomach return, a common staple ever since she found Luke and Harris together in the janitor's closet.

"But why can't I feel that something is not right?" Holly mused as she tried to explain her discomfort. "Probably has to do something with Luke, he is a creep after all..."

But before Holly could think more about the subject there was a knock on the door, and shortly after her brother Harris entered the room.

"Welcome back, Harris" Holly said with a smile as she greeted her brother. "So, how was the saloon appointme-" she continued but quickly silenced herself in shock.

There, in front of her, was her brother, wearing a blue skirt that barely reached his knees with some sheer nylon stockings, black high heels, and a white and black striped shirt.

Of course, this was nothing unusual, as Harris was working here as a secretary, so the thing that ACTUALLY shocked Holly was her brother's new, dirty blonde hair.

"H-Hi Holly" Harris replied, nervously playing with his new hair as he avoided his sister's gaze. "The saloon has been nice. I g-got this totally amazing new hair color. O-oh, and it is H-Hannah now..." he meekly continued, his voice sounding a bit strained.

Once again Holly had to shake her head to get rid of the shock she was feeling.

"Harr-- I mean Hannah, why did you dye your hair? I mean I am not complaining, I think it really fits you, but I just did not think you would do something like this" Holly returned.

"W-Well, you know what they say, right? Blondes have more fun..." Harris replied, his face red from embarrassment.

This made Holly relax a bit, as her mind went to more pleasant thoughts.

"He must be talking about Luke," she thought to herself as her brother mentioned "fun". "After all he always talked about preferring me as a blonde..."

After those thoughts her grin turned into a mischievous Cheshire smirk as she regarded her brother in front of her, looking him up and down like a lioness ready to pounce.

"Oh, and by fun you mean your little get-together with Luke in the janitor's closet?"

Now it was Harris's turn to be shocked, his eyes widening and his mouth falling open in shock.

"Y-You k-k-know about th-that?!" he stammered out in surprise, making Holly giggle.

"Well, of course, I do. The walls of this building are thin, and you are not really keeping it quiet in there, you know?" Holly smirked, making Harris's face go pale and his cheeks go red.

"I have to admit Harr-- Hannah, I was quite surprised when I found out you want to be a woman, and while I can't really approve of your choice of a boyfriend I am still very happy for you," she said before moving around her desk and giving her brother a tight hug.

Said brother just tensed up into the hug before awkwardly returning it.

"Yea, it came as a surprise for me too, but the moment I put on the dress I just knew that I was made to be a woman," Harris said, each word forcing itself out of his mouth.

"Also I must say that my Luky is a really big sweety once you get to know him, while he is being a big hunk in bed" he continued, forcing himself not to gag.

Hearing this his sister released him and looked at him with some doubt.

"Well, if you say so... I still don't think he is good for you, but I will have to trust your judgment..." Holly said, still not feeling comfortable that Luke and her brother are together.

But not wanting to argue with Harris Holly turned her frown into a smile before addressing Harris.

"Well, anyway, I think that you accepting your true self deserves some sort of celebration! I am just finished with my reports, so why don't we go to dinner, and maybe some shopping afterwards?"

"S-Shopping? What would you want t shop for?" Harris asked nervously, not really liking the idea of being forced to go outside dressed like a woman.

"Well, I have been thinking about getting a nice ballgag for you. What do you say?"

"What?!" Harris exclaimed in shock, thinking he just misheard, but his sister's snicker said more than a thousand words.

"A ballgag, silly. I can't have you scream down the whole building while you and your boyfriend get it on in the janitor's closet. And I bet Luke would like you all gagged for him."

Hearing this Harris paled in horror, but he knew he could not really deny his sister without the possibility of revealing what was really going on.

"Y-Yeah, a ballgag so-sounds just g-great" he instead replied with a shaky smile.

"Yay! And maybe we could even get you some dildos for practice. Get some 4-inch ones before we move you to the big 10-inch league, so Luke doesn't have a problem with your backdoor!"

And with that the siblings made their way out the door to fulfill their plans, both having knots form in their stomachs.

For Holly, it was because something still kept nagging at the back of her mind, while Harris just dreaded what the future will hold for him.