Assistance needed Ch. 01

Chastity was nervous going into her new job. She had picked out a white long-sleeve button-up, a sharp black blazer, a pencil skirt, a simple black purse, and simple heels for a professional first-day look. She was already regretting the heels as she walked into the clean white lobby of the huge marketing firm. She was lucky to have this job. Straight out of college and already the assistant to the CEO of the biggest marketing firm in her state. When Chastity heard the CEO, Estelle, speak at her university last year, she knew she needed to work for this company. Estelle was intelligent, driven, and had built this company from the ground up. Plus, the woman was absolutely gorgeous. Chastity had to remind herself to focus on the content of the speech more than once during that conference.

The eager assistant walked up to the large glass elevators and clicked the button to go up. While waiting for the elevators to make their way to the lobby, someone approached her.

"Hi I'm Avery, they/them," They said, "you must be the boss's new assistant".

"That would be me!" She responded cheerily. "Chastity, She/her. Nice to meet you, Avery. What do you do?"

"I am head of the art department" they explained as the elevator dinged to signal its arrival.

"Going up?" Chastity asked.

"Down" responded Avery. "You take this one. Can't be late on your first day. See you around".

Chastity smiled sheepishly at Avery and walked onto the elevator, trying not to slip on her 2 inches too tall shoes. She hit the button to take her to the top floor where she would meet her new boss, Estelle Desai. She had met Estelle during her interview, but it had been a video call. She felt nervous to be meeting her in person for the first time. By the time she reached the top floor, her stomach was churning. She walked off and headed towards the large glass doors that must lead into Estelle's office. When she walked in she smelled warm tobacco and rose. Estelle lifted her gaze from her computer screen and met Chastity's eyes.

"Hi! I'm Chastity! It's so nice to finally meet you in person!" Chastity bounded, unable to contain her excitement.

In response, Estelle slowly rose from her important-looking chair and walked around to lean on her sturdy, oak desk. She motioned for Chastity to come toward her. Chastity did as she was directed and hurried to the CEO. When Estelle decided she was close enough she gestured for Chastity to sit in the tall, black leather chair that sat in front of the impressive desk. Chastity sat.

Estelle's gaze lingered on Chastity for a few moments. She looked her up and down. Chastity looked down at her own body, in case she was looking unkempt in any way. She decided nothing was out of the ordinary. Then, her boss walked back around her desk but did not sit back down.

Chastity held her breath waiting for her boss to speak.

"Hello, Chastity," Estelle said with a low and smooth voice. "I am Estelle Desai, as you know. We already discussed your day-to-day duties. Your desk is outside the door. You can put your bag and any personal belongings in this closet"

Chastity waited for her to say anything more. When it became clear that was all, she got up from the cold leather chair, hung her purse in the closet, and slowly and quietly peeled off her blazer. She felt her boss's stare and turned to nod goodbye to the looming woman and walk out of the clear glass doors. She found her desk right where Estelle said it would be and sat behind it. This desk was more of a minimalist design than her boss's grand piece of furniture. It had a thin glass top and skinny metal legs. She wished she had picked a longer skirt because if she didn't keep her legs pressed together someone could easily see her panties under the tiny table. On top of the simple desk were a stapler, a computer, and a large pile of papers with a sticky note reading "CATALOG" in black sharpie. Chastity pulled off the sticky note and inspected the top paper.

After 4 hours of data entry, Chastity's fingers hurt. She contemplated asking her boss when her lunch break was but decided against it when she remembered their previous conversation. She looked around at the other, less grandiose, doors around her and saw one labeled "Mark Hale - director of operations". She remembered the name from the research she did on the company, and decided to see if he was a more friendly option. She pushed her chair back and stood up. When she went to push her chair in, her top button got stuck on a sharp piece of the chair that was sticking out. It pulled the button off her blouse entirely, exposing her cleavage. Her face turned red and she bent down to look for the missing button. It was no where to be seen. She didn't want to talk to anyone at her professional new office with her cleavage exposed like this, but with a growling stomach, she still decided to ask her co-worker.

"Hi!" She said.

Mark looked up at her, then down at her newly exposed breasts.

Chastity pressed on, "I'm Chastity, Estelle's new assistant. I was wondering if you could tell me when lunch is?" She asked.

"You will have to ask Estelle. She's in charge of you." He explained, looking back down at his screen.

"Oh ok. Thanks." Chastity said, disappointed.

She walked out of the doorway back to her little desk. She organized her papers to see what was finished and what still needed to be done. The finished pile was bigger so she decided it was ok to try talking to the CEO again. She stood up, pulled her skirt down, and tried to push the two sides of her shirt together. She didn't have particularly large breasts, but without the button, her cleavage looked rather impressive. She was nervous about looking unprofessional in front of her boss. She started toward the glass door and pushed it open. This time Estelle did not meet Chastity's eyes but lingered on her breasts. Chastity's face grew red and hot.

"Um... hi again. Sorry to bother you. I was just wondering when my lunch break is." She stumbled.

Estelle let her gaze wander all over Chastity's body. "Did you bring lunch?" Estelle asked, without meeting her eyes.

"I didn't. I was planning on picking something up quickly." Chastity explained.

"Great!" Said Estelle looking back at her computer screen "Bring me back a chopped salad from Vera's and lobster cauliflower bisque from Saint Augustine's by 12:00pm"

Chasity looked at the watch her mother gave her as a graduation gift. It said it was 11:23 am.

"I'm not..." Chastity started.

Estelle finally met Chastity's eyes and the assistant stopped speaking. The intensity of the eye contact made her instantly stop and turn to push the door open.

"Oh and Chastity dear" Estelle called. "I noticed your, ahem, wardrobe malfunctions. I'll have something more durable picked out for you when you get back"

Chastity's face turned scarlet again. She didn't know what to say so she nodded and rushed out of the office to the clear elevators, clutching her collar closed. Her mind was racing so much that she almost didn't notice Avery step off in front of her.

"Hey again," they said to Chastity. They were holding a large white garment bag. "How's the first day going? You look a little frazzled"

"Oh um yeah," Chastity mumbled noticing the bag and feeling mortified. "Just getting used to everything. Nothing I can't handle." She said.

"Ok," Avery said looking concerned. "Let me know if you need anything," they said as the elevator doors closed.

Chastity was so embarrassed. She couldn't believe she had already made her boss unhappy. She felt shame at letting her boss see so much of her body after knowing her for only a few hours. Fearful that she would disappoint Estelle again, she looked at her watch: 11:32 am. She'll have to run.

She somehow managed to get both items requested by her boss despite having forgotten her purse and jacket in the CEO's closet. Luckily, both restaurants had a standing order for her boss and were able to add the meals to a running tab. The places were also within walking distance of the massive marketing firm. Chastity was glad to make her boss happy but, she was disappointed in being unable to get anything for herself without a wallet. Her stomach was growling, her hair was a mess, and she lost yet another button on her white blouse. It was now exposing the top of her light pink bra but didn't have time to worry about that. As she gasped for breath rushing onto the top floor, she saw that it was 11:59 am. She pushed the glass door open with her hip and set the food in front of her boss. Estelle checked the time and smiled when she saw it was 12:00pm on the dot. She also noticed the second button missing on Chastity's rumpled shirt.

"You did it," she said to Chastity's breasts. "Sit with me" she slid the expensive bisque toward her assistant.

Chastity was hesitant but was going to faint if she didn't eat something soon.

"Thank you," chastity said into her soup. She didn't like to take handouts, but when she popped the lid off of the plastic container she no longer cared. She took a huge spoonful of broth, cauliflower, and decadent lobster into her watering mouth.

"If you keep performing like this, I think you will do very well here" Estelle explained, opening her salad container, "I always reward hard work"

Chastity's face grew hot again, but she smiled at the compliment.

After a few moments, Estelle stood and walked over to the coat closet in her office. She took out the garment bag Chastity had seen Avery holding earlier."I had our art department pick this up for me earlier. I think you may be more comfortable in something that isn't falling apart at the seams." She unzipped the bag and revealed a black bodycon dress.

Chastity felt so much shame and anxiety about what she looked like in the presence of someone she admired so greatly. She wanted so badly to make a good impression today that she bought the whole outfit brand new. Apparently, that had been a mistake.

"Of course, I'll need you to try it on first," Estelle said expectantly. "Once you're finished eating. Take your time" the boss looked at Chastity expectantly.

Quickly, Chastity stood and asked, "where can I change?"

Estelle was now standing directly over her assistant. She could easily see down her practically ripped-open blouse.

"Right here is fine" Estelle replied easily.

Chastity was suddenly glowing the deepest shade of crimson she could imagine from head to toe. She was shocked at such a suggestion from her new boss. Even if she could accept that maybe it's not weird for women to change in front of each other, this was the CEO of the company. Not to mention, this office was 99% windows. If she changed in here, any of her new coworkers could see her exposed body.

"Are you sure?" Chastity asked "I really wouldn't mind changing in a bathroom or even a closet"

"No need," Estelle said looming over her subordinate, "you can get changed right here and save some time".

Chastity needed this job. She had hundreds of thousands of dollars in student debt and had already applied to every other marketing firm in the state. This job could also be a major stepping stone in her own goal of being a CEO one day.

She had a flashback to the day in college when she watched Estelle speak. She was a beautiful, full-figured woman with jet-black waves that grazed her muscular shoulders. She wore a form-fitting black dress that exposed her arms, and chastity swore she glimpsed the edge of a black and white tattoo on the CEO's shoulder. She remembered staring at the woman's hands as she gestured to the PowerPoint slides. They were strong and steady. Her wrists were delicate and she had short neat fingernails. Chastity was intoxicated by Estelle's smooth alto tone and her attention-commanding presence. The college student had spent countless nights researching Estelle after that day. She was addicted to the woman. She would do anything to work with her.

Chastity waited again to see if there were any other options but found none. She stood and began undressing in front of Estelle. She undid the remaining buttons on her blouse and slipped it off of her body. Then folded it and placed it on the leather chair she was sitting on before. Then she unzipped her pencil skirt and began sliding it over her hips revealing the thong she was wearing to avoid panty lines in her form-fitting skirt. Her boss admired the new skin Chastity hesitantly exposed. As the assistant folded the skirt her boss handed her the new outfit. The dress was difficult to shimmy on her curvy body. She had to jump to get it over her hips which made her full chest jiggle. Her boss looked pleased once she managed to get it on.

"You look great! Let me" Estelle said gesturing to the zipper on the back of the tight dress

Chastity spun around and Estelle stopped the woman by touching her waist when her back was to her. The CEO walked close and forcefully pulled her back.

Estelle reached for the zipper and slowly pulled it up from her lower back to the nape of her neck. Then, the boss opened the closet door to reveal a full-length mirror.

"What do you think?" Estelle asked

"I... I... don't know what to say" Chastity responded checking herself out.

The dress was tight, revealing every curve on her body. There was a peek-a-boo cutout to expose her cleavage and had a cut out in the back that almost reached her butt.

Estelle walked up behind the woman looking in the mirror and whispered "you look so damn good"

"Now bend over" Estelle commanded, walking further away to get a good look at her exposed body.

Chastity, stunned, reluctantly did as she was told. She told herself her boss just wanted to make sure it was an appropriate length.

"Mmm good girl" Estelle purred

Chastity froze.

"D-does this look better?" She stuttered.

"Fuck yes. You have a beautiful body" Estelle said as she pulled off her own blazer, placed it in the closet, and shut the door. Then, she took chastity by the hand and walked her to the impressive desk.

"I'm not sure if this is quite right for you though. I'll call down and have Avery pick out something new" Estelle explained.

She unzipped the woman's dress as slowly as she zipped it. Estelle peeled the form-fitting piece off of the assistant. Then she took her by the waist and lifted her onto the wood surface.

"Separate your legs," Estelle said softly

Chastity parted them slowly, embarrassed to expose her wetness. The experience of having her boss dress and undress her had turned Chastity on against her best efforts. Trying to remain professional on her first day now seemed like a pipe dream. Estelle noticed the nearly nude woman's glistening core, and she lightly grazed Chastity's clit through her panties. Her breath hitched at the surprising touch. She touched chastity's upper thighs. The woman on the desk's breathing got even heavier. Her boss moved up to her bra and undid the clasp exposing her breasts.

"Would you like me to put your old outfit on you dear?" Estelle whispered to Chastity rolling her assistant's nipple between her fingers.

"N-no" gasped Chastity

"Want me to stop?" Asked Estelle

"No," Chastity said in a small voice

Estelle moved close and put the nipple she was playing with in her mouth. Licking and nibbling softly. Chastity let her head fall back with a sharp inhale.

Just then Avery walked in.

"I see she liked the outfit," Avery said, announcing their presence

Chastity immediately covered herself with her arms.

"Not quite," Estelle said, turning her attention from the woman's body. "Would you be able to find something a little less fucking sexy? I'm trying to run a business here."

"Oh course, I'll get right on it!" Avery said sincerely.

Chastity shivered with the embarrassment of being naked in her boss's office. She didn't know what to do so she leaned over to get her clothes.

"Oh no no." Her boss stopped her. "Not yet" "what did you need, Avery?"

"I just need a signature on this and I wanted to let you know that the design on the panty project might be a little later than anticipated," Avery explained, ignoring the naked woman sitting inches away from them.

"Ok. Put it on my desk. I'll get to it right after this," Estelle said looking back at Chastity eagerly, "Someone better be on death's door for what this ad is costing me!" Estelle said looking over her shoulder

"That's what I told her," Avery said on their way out

"That's the head of our art department," Estelle said teasing Chastity's clit with her fingertips "You'll learn who everyone is soon enough"

Chastity gasped at the friction she was finally getting between her legs.

"Take off your panties" Estelle commanded

Chastity did as she was told and pushed her panties down her legs, letting them fall to the floor.

Estelle got on her knees in between the sitting woman's legs and put her nose in her bush. She licked gentile circles around Chastity's clit until she felt it swell under her tongue. Chastity put her head back again, forgetting where she was and getting lost in the pleasure. Estelle stuck one finger in the woman's slit slowly pushing in. Chastity moaned with pleasure and looked down at what her boss was doing. Estelle looked up at her, tongue still working on her clit. Estelle curled her finger inside still licking her clit and earned a loud moan. She inserted another finger rubbing the top of her pussy and licking her clit in unison. Chastity grabbed a handful of Estelle's hair and grinded her hips. Estelle did not let up. She sucked hard on the other woman's clit and started fingering her harder and faster.

"Oh my god, I'm cumming!" Exclaimed Chasity out of breath

Estelle kept her fingers in chastity until she felt her walls release. Then the boss stood up, kissed Chastity on the forehead, handed her her clothes (including the black dress deemed "too sexy"), and walked back to her desk chair.

"Tomorrow you will be expected to return the favor," Estelle said, out of breath, "See you then".

Chastity caught her breath and got dressed. She decided on the black dress rather than the broken blouse. This time her boss kept her eyes on the computer. Chastity looked at her watch and saw that it was time for her to go.

"See you tomorrow," she said confused, and quickly walked out of the office toward the elevators

Chastity touched the button to go down when Mark Hale appeared behind her.

"Saw you had a good first day," Mark said staring through her dress. "Make sure you stop by my office tomorrow morning to show me the new little outfit you get. I can't believe she gave you something even shorter. All day, every time I looked over at your desk and saw you were showing your little pussy I had to rub one out. Of course, that wasn't as good as what I saw in Estelle's office." He grabbed her ass as he walked past her to get on the elevator, "going down?"

"I actually forgot something in the office," Chastity said at the ground in a voice so small she barely heard herself.

"Too bad. See you tomorrow, office slut" Mark said as he hit the lobby button

Chastity felt hot tears fill her eyes. She didn't want to be known as the office slut. She needed to get out of there, but she actually had forgotten her purse and jacket in Estelle's office. She turned to go back into the office, eyes blurred from the tears. She pushed open the double doors and heard moans coming from the CEO's computer. Estelle was masturbating. She paused the video.

"Can I help you with something, dear?" Estelle said fingers still over her clit.

"No sorry" Chastity apologized, hiding her face "I just forgot some things in your closet"

Chastity hurried out.