Office Policy

“I can’t believe I was fired.” Jackie sighed. “Rent’s due in two weeks but I can’t get my stupid severance pay till next month.”
Her friend Liam peeked up from his laptop. “Got any savings?”
Jackie groaned. “I wish. The day I get savings is when hell freezes over. How can I find a job fast that’ll pay me right away?”
He shrugged. “I mean, you could work for me as my personal assistant.”
Jackie’s eyes widened in surprise. “Wait really?”

Liam worked for his father’s business conglomerate and was being molded into the next CEO. He even had his pictures taken for many business magazines, calling him the next prodigy.
“I don’t see why not. You’re more than qualified. Plus I can throw in a nice sign on bonus.” He playfully winked at her from above his screen.
“Let me look a little harder. If not, I’ll have to let you know.”

Jackie wasn’t against working for her childhood friend. They’ve known each other since they could remember. Her mother would always take her whenever she cleaned up in their building. Liam never made her feel belittled for being the housekeeper’s daughter. He was always fiercely protective over her. They even got into the same university together. But Jackie wasn’t blessed with Liam’s connections so she ended up working part time jobs while searching for better jobs. Graduating in the middle of the recession also didn’t help her cause. Since university finished she hardly saw her friend, save for when he popped by the cafe she used to work in as a barista. But she always knew that he always cared for her.

Once another week passed by with a single rejection email, Jackie found herself texting Liam about the job opening. Almost immediately he responded, which was unlike him, and found a massive contract at her doorstep the next day.
She flipped through the pages. “How on earth does a personal assistant need to sign so many NDAs.” she thought to herself. Some even required a notary and witness when she signed. Under all those were basic office policies she had to follow including dress code and general tasks she was expected to do.
Her phone dinged with a notification from Liam. “You can come up to my office when you receive your contract. We can get everything signed and all other office policies met tomorrow.”
She clicked her tongue. It was like him to text so formally.

The next morning Jackie woke up extra early to fix her makeup and hair. She was by no means a model, but more like the cute girl next door. She looked mostly androgynous, save for her only feminine feature being her hair. Her jet black hair just barely reached her waist, thanks to her skipping out on haircuts to save money. She never had much of a womanly figure, her chest barely required a bra since she remained in the double AA territory.

Because of this it was crucial for Jackie to accentuate her feminine charm. She fixed her makeup to make her almond brown eyes pop. Her long hair was intricately placed into a braided bun. She still wore a quite conservative suit with her skirt tailored to cinch at her small waist. “Alright, it’s go time.” she thought.

Her nerves kept her on high alert till she reached the familiar building in downtown. She hadn’t stepped foot inside since Liam persuaded her to join him at their Christmas party. The housekeeping staff smiled at her as she walked through the glass doors.

Liam’s office was on the second from the top floor. He was waiting by the door looking anxiously at his watch. His unruly blonde hair looked even more unkempt than usual. Under his piercing blue eyes were dark bags.
“Rough night?” He perked up when he saw Jackie walk in.
“Oh thank god. I’ve been without an assistant for a few days and the replacement is god awful at her job.”
They sat down and after what seemed an eternity of signing and confirming NDA’s with the lawyers, Jackie was officially Liam’s assistant. Liam breathed a sigh of relief.
“Sorry we gotta throw you through the ringer, but since you’re familiar with how we run things I figure it won’t be too bad. You read all the office policies before, right?”
“Yea I skimmed it a bit.” Jackie nodded as she flipped through the assistant handbook.
“Alright,” Liam glanced down at his watch and groaned. “I have to prep for my meeting in the next room. The ladies will get you more familiar with the policies. Then we have a meeting with Dad in a bit.”

As he exited the office, two women appeared at the doorway. They didn’t seem like office ladies, dressed in more fashion forward casual wear. One was a brunette, the other blonde.
“Are you Jacqueline Kang?” One asked as they both eyed her from head to toe. She nervously nodded.
“We got our work cut out for us today hmm…” They linked their arms with Jackie on each side and lead her into the next room. Jackie rarely went inside his personal study. Inside was a spare bed for overnight stays and a place to get ready. Set up was a large mirror and a chair and cape.
“What are we doing here?” she timidly asked.
“You did read the office policies right?” One asked as they sat her down in the seat. “Especially the one about personal assistant’s appearances. Mr. Liam has specific requests for us today for you. It is our responsibility to make you look – professional.”
The other lady untied Jackie’s long hair from her bun. Long black hair tumbled down to her waist. The first helped her out of her suit jacket as she pinned the cape around her neck a little too tight. Jackie’s eyes widened in surprise.
“Wait – are you guys cutting my hair?”
“Unfortunately yes.” The blonde pulled out a contract with highlighted lines. Jackie grabbed it and read “Personal assistants should adhere to professional appearances at all times as determined by employer’s specifications.”
“Ok yeah this is a little vague, but I’ve worn this exact hairstyle and suit to almost every job fair and presentation. No one has complained about me being unprofessional.” Jackie protested as they started braiding her long hair on each side.
“Oh no honey,” the brunette said. “You look lovely, too lovely even. Mr. Liam probably didn’t say anything since he didn’t want you to back out.”
“Trust us. It pains us to do this but Mr. Liam has his reasons which we agreed with.” They finished plaiting each side of her head. “But we can ensure that a patient would be so blessed with a wig with this donation. You had lovely hair.”
“Had?”

Unceremoniously the two pulled scissors out of their pockets. They each began hacking through each braid. Jackie could feel tears forming in the corners of her eyes. Her one feminine trait was being cut away from her. She stared directly in the mirror, trying to keep her composure. She hated every second of it. The tight tug each braid was getting looser and looser. Her head grew lighter. Short hairs flew to the front of her face as they were freed from the shears. The longest barely reached her chin. She could feel the cold air conditioning biting on the nape of her neck.
“Alright, the worst is over.”

Jackie’s former glory was gone. Her makeup was all smudged from crying. That morning she lovingly braided waist length hair. Now that hair was laying on the counter in two braids. What was left was a makeshift bob that just touched the tip of her chin.
“If he wanted me to get a stupid bob he could’ve asked me to go to a salon beforehand.” Jackie cried. “This feels like a total blindside.”
The brunette gently pinned the top layers up. “Honey I’m afraid we’re not stopping at a bob.”
Unfamiliar buzzing filled the room. Jackie glanced at the blonde who was holding clippers.
“Please no. I don’t want to go any shorter. My hair is my greatest asset.” Jackie begged. “I’ll find a different job.”
“Sweetie, we and you signed the contacts. Don’t make this harder than it has to be.” The blonde practically forced Jackie’s head down to her chest. She felt the clippers bite more hair away from her scalp. She seemed to be shaving all the way up to her ears.
Jackie shut her eyes closed. How dare Liam spring this on her. As children he once got gum in her hair and she had to get a dorky bowl cut. She hated having her ears stick out for everyone to see. But she did like it when he would stroke her undercut whenever the two of them were alone. She felt in her gut that it might be the haircut Liam requested as some sick joke.
“Alright Jackie, we’re going to keep the top layer long enough to style. Mr. Liam wanted us to give you -”
“A bowl cut right?” Jackie rudely spat out. Normally she wouldn’t be so rude but she was so angry.
“Yes. Although if you dislike it you can always go shorter.” The brunette spoke. “I do think it looks nice on you.”
The blonde let down the chin length tresses and began combing it from the center part. With precise snips she swiftly cut bangs that were slightly above Jackie’s eyebrows. Her gut felt heavy as the blonde used it as a guide to keep snipping around her head. The bowl ended up being a few centimeters above her ears, way shorter than her childhood haircut. Underneath the bowl was a faint dusting that felt more like stubble than hair. Jackie felt like she went from a solid 7 to below a 1. It would take years for her hair to grow back to its former length. Her ears stuck out, now freed from the thick blanket of hair. There was no styling that could change it from a strict bowl cut. She was stuck with it until it grew out.

After tinkering with her hair for a bit longer they finally undid the cape. Jackie’s hands immediately flew to her head as she stared in the mirror. Her undercut felt rough and foreign. The bowl itself stayed firmly in place since her hair was so straight. She felt like she was transported straight to the past.

“Ms. Jackie, when you’re done with checking our work we can address your wardrobe.” The brunette opened the closet to reveal a row of suits. “He wasn’t sure if he got your measurements right.”
The blonde held out a black suit. “He would like you to wear this for the meeting. We’ll be outside if you need assistance.” They both stepped outside and allowed Jackie some privacy. She sighed and began undressing. It was a basic black suit it seemed, but did nothing for her petite figure. It hung off of her awkwardly and made her look boxy.

The women stepped in once more. “Oh thank goodness it’s tailored right.”
“I’ve had tailoring done, I think -”
The blonde interrupted her. “It’s tailored specifically to Mr. Liam’s needs. Now please remove your makeup and jewelry. You can leave them here for now. Oh and these are for you.”
She handed her a pair of thick black glasses. “I have perfect eyesight.”
“Non-prescription blue light lenses.” the brunette said. “Mr. Liam insists on protecting your eyesight and wants you to wear them during business hours.”

Jackie washed her face and left the small gold earrings she wore on the counter. She glanced up at her reflection once she placed the glasses on. It was her face, but not quite. Her boyish body looked even more androgynous in the suit. The thick frames obscured her soft facial features. The harsh bowl cut made her jawline more pronounced. Liam had some explaining to do.

Liam walked in again glancing down at his watch. Jackie was about to start yelling at him for this sick prank but he spoke first. “Oh thank god they work magic don’t they.”
Jackie’s words stuck to her throat. Did he earnestly request this un-makeover?
“I’ll explain everything after the meeting, Jackie. Please.” He thrust a laptop into her arms. “We’re running late so just take notes for me.” She nodded as they ran to the meeting room.

The board room was one of the few they never played in as children. Liam’s father was already sitting at the head of the table. “Liam my boy, I see you have a new assistant.”
“Yes Father,” Liam said as he sat down. “You’ve seen Jackie before.”
His father squinted a bit and nodded. “Ahh, yes little Ms. Kang. I hope your mother is still doing well. I see you still wear your hair like that huh…” He seemed a bit disappointed.
Suddenly a woman burst into the board room. “Sorry I’m late.” She wore her long blonde hair loose. Every stitch of clothing was molded to every contour of her body. “I’m Kylie, your father’s new assistant.”
Liam sighed. “I see we both got new help.”
“Well the other wasn’t up to my standards.” His father suddenly grabbed Kylie’s ass and played with her long hair. “Kylie is pretty cute don’t you think?”
Liam rolled his eyes. “Let’s get on with it and we’ll be out of your hair.”
After an hour of Liam and Jackie awkwardly ignoring their PDA they were free and suddenly eating dinner in Liam’s apartment. Jackie was practically stunned into silence after the day’s events.

“As you can see, Father is still the same as always.” Liam spoke, cutting the quiet.
“Yea a little warning would’ve been nice” Jackie slammed her fork down.
“Jackieeee.”
“What the fuck Liam! You cut my hair, you give me a whole business wardrobe out of the blue. Do you know how long it’ll take to grow out?”
Liam looked away from her glare. “I mean, it feels quite nostalgic, no?”
She ran her fingers through her short hair. “You of all people know best that I look awful with this hair.”
“I had to do it to protect you.” He stood up and took her hands from her head. Gently he stroked her exposed nape. “With Father the way he is, I didn’t want his eyes on you.”
She placed her head into his chest. She didn’t realize how much she missed his hands at her nape. “You don’t need to protect me.”
He took his hand from her head and lifted her chin. He realized how fragile she looked after being stripped from her hair.
“But I wanted to.”
He gently kissed her. Her eyes grew wide.
“You think the only beautiful thing about you is your hair but I can assure you that you don’t need it. Honestly you could shave your head and be bald for the rest of your life and I would still think you were the most gorgeous woman I’ve ever met.”
Jackie’s cheeks flushed. “How long have you been waiting to say that?”
“Since the day we met. Father never liked me and you but I don’t care about his approval.”
“I don’t know what to say -” Jackie was interrupted with another kiss. He lifted her into his arms and carried her into the bedroom.

He fumbled with her unbuttoning her shirt as she took off his belt. Underneath the boxy suit she still was quite feminine.
“You know you could’ve confessed and I wouldn’t have to have this stupid bowl cut.” Jackie murmured as she pulled out his rock hard cock.
“If you really hate it that much,” He paused and grabbed his beard trimmer nearby. “You could just take it all off.”
“And you’ll have a bald assistant? We’ll be the talk of the company.”
“You could rock a wig, any style you want as long as it’s short enough. But in private I’d want to keep you shaven. It’s in the contract after all. I get to choose what’s best.” He flicked the clippers on. She nodded and began sucking him off. He was much bigger than she thought. Above she could hear the vibrations of the beard trimmer cutting away at the last locks on her head. Three inch hairs fell all around her. She could feel the cold rush of air on her virgin scalp. It would likely be patchy but she didn’t care anymore.

Liam tried to hold it in as much as he could until he shaved the rest of her bowl off. Not his greatest work for sure. Her head bobbing up and down made it very uneven. He could see the pale white skin of her scalp peeking through the rough black stubble that remained. He couldn’t hold it in anymore and pulled out suddenly. He came all over her barren scalp, covering the faint traces of hair with his cum.

Jackie sat there as he wordlessly pulled out a razor. She began taking off the rest of her clothes and sat patiently. She began the day with waist length hair and starting a new job with a childhood friend. Now what was left was being shaved off completely by her now lover. She could feel herself get wetter with each scrape of the razor. Tiny bits of hair and the sticky residue rained on her nude body.

Liam had to concentrate to not nick Jackie’s scalp. Slowly with every stroke of the blade her pale white scalp shone. Finally her hair was completely under his control. His cock was trembling with excitement again. The longest she would have her hair would be stubble, he decided. She did look best bald. Daily blowjobs, daily head shaves, he would request her to add into his schedule. He could tell that she was getting into it too by the wetness on her panties. Not only could he stay with his childhood friend but now they shared the same fetish.

Once he finished he placed his hand firmly on the top of her head. She recoiled at his touch. Her bare scalp was much more sensitive than the bowl’s undercut. She turned towards him and saw he was practically hard again.

“Ready for round two?”

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