A Very Personal Assistant

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CEO & PA have unknown crushes on each other.
6.6k words
4.68
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Part 1 of the 2 part series

Updated 02/05/2024
Created 12/31/2023
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The Very Personal Assistant

A thank you to those who have that helped me with this story.

"Ladies and gentlemen, it is my honor to present to you the new CEO of Watson Enterprises, Ms. Kathryn Watson."

Her name tag said "Katie Watson" but everyone in the boardroom already knew her name. Few knew much more about the daughter of the late CEO Jim Watson, whose father started the company. Rumors about Katie ran rampant throughout the company. There were many questions. Today, they were getting some answers. The members on the Board were taken aback by her stunning beauty. Besides her model-like appearance was an air of intelligence and confidence. A brief round of applause followed her entrance.

Katie knew exactly the image she was trying to portray. She chose a tailored gray jacked and skirt because it showed both her amazing figure but also a lot of class. She felt she needed to impress those in the room. She gripped the sides of the podium and looked at everyone, trying to exude confidence but had butterflies in her belly. Deep down she was afraid she wasn't up to the task.

She said, "To answer the question that many of you are asking, yes, I am qualified to take over the company with my father's passing. For the last three years, he prepared me. Not only did he groom me for the position, but my engineering degree from M.I.T. demonstrates my knowledge to run the company."

She continued her speech, discussing how she planned to carry on the excellent reputation her father had built in the industry.

Hannah was seated at a table against the wall behind Katie. She had been Jim Watson's personal secretary and after Jim's untimely death, had no idea what would become of her. Hanna wasn't even sure she would have a job. After all, what if Katie had her own assistant? She would find out later and her world would never be the same. All she knew was she had a crush on Katie since the first time they met.

Hannah marveled at how gorgeous Katie was. She thought to herself, I'd love to have a figure like hers, and that long blonde hair. She looks really good in that outfit.

She listened intensely to Katie's speech, awed at how the new CEO's poise and confidence added to how smoking hot she already was. She tried to stop her thoughts about her. They weren't appropriate, considering the woman was possibly her new boss. Despite her best efforts, Hannah tried focusing on Katies's words but was too distracted by her infatuation with the woman standing in front of her. Hannah had no real experiences with women, but she knew what turned her on.

Sitting behind Katie, she thought she had a perfect ass. She looks so perfect, Hanna pondered. I'd love to rub my hand across that ass.

Hannah was lost in a fog of desire which had become more than just a crush: it had turned to lust. Eyes closed, in a whisper, she quietly said, "God, that woman is smoking hot."

When Katie finished her speech, Hannah was still in her fantasy world. Everyone but her and Katie had already left the room. She heard what Hannah whispered and said to her, "Excuse me, Hannah?"

Hannah was surprised and a little startled.

"Do you like what you see?" Katie smiled. "Do I meet your approval?"

Realizing she'd been caught, Hannah's face flushed with embarrassment. She lowered her head down and stared at the floor.

"I'm sorry, I... I shouldn't have said that."

"It's okay, I don't mind you looking. In fact, I take it as a compliment," Katie said.

Katie thought Hannah's cute reaction made her even more appealing. Her innocent face, her petite perky breasts, hidden modestly behind a conservative blouse, her shyness and naivete. She was intrigued by Hannah's comment: after all Hannah had caught her eye in the past. She wanted her and hoped maybe the feelings were mutual.

Katie's father had hired Hannah as his "Executive Assistant" just out of high school three years ago. But really, the job was nothing more than to be his errand girl. He expected her to jump at his bidding.

As everyone left the board room, Katie put a hand on Hannah's shoulder and said, "I want you to come to my office tomorrow. I would like to talk to you about a position I would like to offer you. How does being my personal assistant sound?"

Hannah thought about those words: personal assistant. Probably nothing but a fancy word for secretary, errand girl, or something like that. Nothing will change, just the person who bosses me around."

Katie saw Hannah's look of disappointed. "Now, before you let your mind go somewhere it shouldn't, let me tell you what I need from my personal assistant. Yes, it might mean some of those 'secretary-type tasks.' However, there's so much more. I know how my father treated you. I'm not like him. I know how to treat a lady and fellow professional. As my personal assistant, you won't be a secretary, but more my right-hand woman. You would keep me organized, manage my calendar and other things I may ask of you as well."

Hannah couldn't believe her ears. She thought, "Work with her every day?" She couldn't deny the attraction, how her brain was sending electric shocks to her pussy. "What am I thinking? She's probably straight. But even if she isn't, what chance do I have attracting someone like her? I'm too young and plain, not what someone would call pretty."

"Why me?" Hanna said, "They're others with more seniority."

"Because I want you. I want you as my assistant," Katie stated firmly.

To herself, Katie thought, I want you in other ways too, but you probably aren't interested in women, much less an older woman like me.

"I'm not sure I'm qualified," Hanna said. "Your father always told me I wasn't a very good secretary. He only kept me around because he didn't want to train someone else."

"My father was an asshole. He acted like he was a king and anybody else like peasants who should jump at every command. I'm not like that. Please give me the chance to prove that."

Katie took her hand off Hannah's shoulder and slid it to her chin.

"Come to my office tomorrow so we can talk about this some more," Katie said, admiring the look of Hannah's lips and wondering what her reaction would be if she kissed her.

Hannah found herself standing alone and incredibly aroused. She didn't know what had just happened. All she knew was her nipples were rock hard and her pussy ached and clamored to be touched. She closed her eyes and fantasized about her and Katie in bed like she'd seen in lesbian porn movies.

It'll never happen, she thought. She wouldn't want someone young like me.

Katie walked to the ladies' room. As she splashed water on her face, she looked at her reflection.

Kathryn Marie Watson. What's wrong with you? You can run a major corporation, but you can't decide if you want to come onto this young thing? She's not Janelle, your last girlfriend, and definitely not a bitch like she was.

Katie couldn't get her mind off Hannah. She headed to her office and locked the door. Plopping on the couch, she reached down and pulled her panties off. She was almost frantic. Spreading her legs, her hands raced to her pussy.

"Oh, Hannah. Fuck me," she breathed.

She was so wet that two fingers slid in and out of her quivering pussy with no effort. Feverishly, she began rubbing her clit with her other hand. Her clit was throbbing and it didn't take long before an orgasm flooded over her. Katie started shaking and thrashing as the orgasm rolled over her. As fast as the climax came, the high it often brought left just as fast. She laid there and brushed a strand of hair from her face, feeling sort of satisfied but wanting more. She pictured Hannah's breasts, her cute figure, her face when Katie made her cum.

*****

The next day, Hannah arrived at the office for her meeting with Katie. She was still confused by their conversation at the meeting. And this personal assistant job? All she knew was she really liked being close to her.

Maybe someday we could be more, she thought.

Katie opened her office door and welcomed Hannah. She enjoyed the view of Hannah walking to the desk and standing in front of it—her bright smile, her perky breasts, that cute butt.

"Ms. Watson," Hanna said, trembling, "you wanted me to come and talk about this position thing?"

"Honey, please call me Katie. I'm only Ms. Watson in formal settings with clients. Even though you're younger than me, I don't want to be just your boss, but a friend as well."

And maybe more, Katie thought.

When Katie moved close, Hannah inhaled the soft scent of lavender emanating from her. It was almost intoxicating. Her heart was pounding and she felt a tingling sensation all over. Goosebumps covered her arms. She took a half step back.

Walking over to the coffee pot and filling her mug, Katie asked, "Want a cup?"

"Uh, sure," Hanna said. "Cream, please. No sugar."

In her head, Hanna told herself, Stop! Think about work. I've gotta get rid of these thoughts about Katie."

Katie handed Hannah a mug and motioned to the couch. "Why don't we sit over there?"

After they sat down, Katie said, "Here's the deal: I need someone to help me stay organized, keep my calendar for me. I need someone to be my 'gate keeper' and shoo people way I don't need to see and let me know about those I should."

Hannah nodded. "Okay."

Katie continued. "You'd make arrangements when I have a business trip. I want you to be my plus one—to come on trips as my companion. I hate going on business trips alone. I also need someone to keep me from making an ass out of myself, or to reign in my bitchy side. Does that sound something that might interest you?"

Katie watched Hannah's eyes widen and her breath quicken. It seemed like she was going to accept, but then she saw doubt cloud Hannah's face.

Hannah sat, conflicted. How was she going to be around this woman without looking like a fool?

"I need some time to think about it," she said. "But it does sound interesting."

Katie then rested her hand on Hannah's thigh, making Hannah's breath become shallow and her hands shaky. She couldn't quite comprehend what was happening. Katie's touch felt gentle, almost sensual. Hannah figured she was only imagining things.

Looking into Hannah's brown eyes, Katie said, "You seem so jittery. Relax, I don't bite, at least not hard." Katie chuckled. "I know there's been so much going on since my Dad died. I know we're just getting to know each other. Like I know Dad hired you right out of high school. You're bright. You're capable. Can I ask why you didn't go to college?"

Hannah looked at the floor. "Issues with my parents. They threw me out. So, I had to get a job, an apartment, and there wasn't a chance for college."

"Wait a second, your parents threw you out? Why they anyone do that?"

Hannah looked up with tears in her eyes. "Promise me you won't tell anyone."

Katie reached up a wiped away a tear. "Of course."

"I'm not into boys," Hannah said quietly. "I prefer to be with women."

"Your secret's safe with me." Inside Katie was thrilled. Maybe there was a chance.

They chatted more. Hannah said she preferred pop music, while Katie liked jazz. Katie loved skiing and kayaking. Hannah enjoyed long bicycle trips. They both started to be more comfortable around each other.

Katie thought to herself, well, here's goes nothing.

She held Hannah's hands and said, "Yesterday, when I said I wanted you, that's what I meant. I want you. I love your smile, your laugh, your simplicity. I want to get to know you better. Being my assistant, you could be someone I confide in, to share things with. I really don't have anyone in life I can do that with."

Katie let out a nervous sigh, wondering how Hannah would react.

Hannah didn't know what to say. On one hand, she was excited to be able to spend time with Katie. On the other, what was Katie asking? It almost felt like she was coming on to her. Her heart was beginning to race, but her mind was telling her she was still imagining things. There was no way Katie could be interested in her. But boy, was she interested in Katie.

Hanna said, "I'm not sure what to say. There's so much to take in."

An awkward silence filled the room until Katie said, "There would be a significant raise, plus I would give you a clothing allowance. Some of the functions I attend are rather dressy. And when we travel, the company pays for all expenses." She imagined how Hannah would look in an evening gown.

Hannah nodded. "I need a little while to think about this." Inside, her head was like a washing machine on the spin cycle.

Katie nodded. "Tell you what, Hannah. Why don't you take the rest of the day off? It's a nice day. Go outside, get some fresh air and do some thinking. Whatever you decide is all right by me."

After Hannah closed the door, Katie took a long swallow of her coffee and thought, Well, she didn't run away screaming. Maybe—no. Girl, slow it down, don't chase her away. Unconsciously, she dropped her hands into her lap and started rubbing.

******

The next day, Hannah made sure she arrived at the office before her boss. She decided she wanted to take the position.

When Katie arrived, she was surprised to find the lights on and her door open.

She stepped through the doorway. "Hannah, are you here?"

From behind the door, Hannah stepped out.

"Hi, Katie. I wanted to have things ready for you to start your day. As your personal assistant, I want to always have things ready for you." Hannah tried to sound confident, but did not succeed very well.

Katie walked over to her. "I'm very happy you accepted my offer, Hannah."

She reached to place her hand on Hannah's shoulder, but Hannah turned it into a hug. It started as a simple polite hug, but it lingered. Their bodies pressed close to each other, Hannah resting her head on Katie's shoulder. As the hug continued, it became more of an embrace. Neither wanted to let go, but slowly they parted.

Stepping back, Hannah blushed. "I'm so sorry, I shouldn't have—"

Katie interrupted. "Honey, there's nothing to apologize for. That was a wonderful hug. You are a wonderful young woman. Nothing wrong with an affectionate hug between two friends." Katie wanted so much to take things further, but her inner voice urged caution.

Hannah was trembling, wanting so badly to tell Katie about her feelings. Not knowing Katie was thinking the same things, she was terrified Katie would be appalled. An uneasy and awkward silence filled the room.

Hannah finally broke the stillness. "I suppose I should start setting up things for the office. I'll need access to stuff and passwords. Maybe I could have a sort of To Do list?"

"There's a folder on my desk with everything you'll need. Use the same desk you have been using."

Hannah said, "Well, I better get started. Don't want to tick the boss off before lunch."

She got up and hurried out the door.

After a couple of weeks, Hannah and Katie fell into the routine of office life. Hannah discovered that Katie seemed to prefer emails instead of face-to-face communications. She wondered if there was something she did wrong.

I don't know what I did to upset her, she thought. She took a deep breath and hit the intercom. "Katie, are you busy?"

"No honey. What's up? Come on in."

Katie had felt an uneasiness between the two. She was torn between telling Hannah her true feelings and fearing her rejection. She was so happy Hannah was turning out to be a great assistant.

Hannah stood in front of Katie's desk, head down, eyes on the floor.

"Are you mad at me? Did I do something to upset you? Whatever it is, I'm sorry."

"I'm not upset with you, Katie! Why would you think that?"

"Well, you seem to be avoiding me. You only talk to me on the phone or in emails. I figured I must have done something wrong." Hannah fought back tears. "Maybe I'm not right for the job."

Katie wasn't sure what Hannah was talking about. "No, no, no," Katie said. "Hon, you're doing a great job."

Then it dawned on her that she'd been trying hard to keep her real feelings in check, and that maybe she was avoiding Hannah because of it.

Katie said, "I guess I'm use to just using email and stuff to communicate." That was a bold face lie. "Tell you what, why don't I take you to lunch? We can do the Sushi bar or the Taco place. You pick."

Hannah was relieved to know she hadn't upset Katie. "We can do tacos. I'm not too fond of raw fish."

"Well, then tacos it is. Let me grab my phone."

They walked down to "The Taco Shack" and got a booth.

Katie said, "I'm sorry you thought I was upset with you." She took Hannah's hands. "I've been a little overwhelmed with everything. I don't know how Dad handled running the company. I guess I've sort left you on the side of the road."

"Just let me help you," Hannah said, pleading. "I want to be the person you need. I can't help if you don't let me." Hannah wanted so much to confess her crush on Katie, but didn't know how.

While waiting for their food, they began chatting and learning more about each other.

"Could you tell me more about the Hannah outside the office?" Katie asked.

Hannah shrugged, "I do a lot of reading. I love playing tennis. I do things that help me forget about work. Often, I wasn't happy working for your father.

"Well, I hope you're happier now."

"Oh yes," Hanna said. More than you know. And I'd be even happier if I could tell you my feelings, she thought.

Over lunch, they talked to each other, both opening up more of their personal lives.

When getting ready to go back to the office, Katie opened her arms and said, "Come here."

She took Hannah in her arms and gave her a hug. Hannah felt so good in her arms.

"I'm glad you said something, Katie said, loving the feel of Hannah's body crushed to her, her scent, her warmth, how her initial stiffness melted and she returned the hug. "I need you, you're what I need." She stopped before saying something she might regret.

****

As time went on, the friendship between the two became very strong. Going out to lunch became a Monday ritual.

"When we get back to the office," Katie said after lunch one day, "I need you to make all the arrangements for us going to Houston next Monday for the meeting with Solar Energy. We're working on a contract to help with their infrastructure plans. Arrange the flights, Hilton Suite for two nights, rental car, the works. I've got the particulars on my desk."

Every time Hannah needed to talk with Katie, she got butterflies. She was getting desperate

to tell Katie about her feelings, but feared rejection and losing her job.

Katie found herself in a dilemma. She longed to tell Hannah how she felt about her but was so afraid how she might react. She also was worried about how it would look to the board if they started a relationship outside of work. As a result, there was an uneasiness between Katie and Hannah that started to be noticeable.

Monday afternoon came and they took the shuttle to the airport, then discovered flights were running behind and theirs was delayed at least two hours.

"Why don't we go over to the VIP Lounge and chat?" Katie suggested.

"Sure. Sounds like a great idea! Lead the way," Hannah said, jumping up excitedly. She had never been in an airport lounge.

The lounge was the airline's VIP area. Access was limited to business executives with memberships. Everyone looked important. There were leather chairs, fancy decorations, even waitresses who asked what they could bring you. Katie seemed quite comfortable in this environment, but Hannah felt like a fish out of water. She felt like she didn't belong there. When she saw how Katie was at home in the lounge, she tried to enjoy herself.

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