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Meagan's Journey Into Business - Her First Day

Meagan's Journey Into Business - Her First Day

This is Meagan’s story of adventure into being stripped, fucked and beyond.

With that, Meagan slid into the backseat and settled in as Andy closed the door and went around to get in the front. He pulled away from the curb starting Meagan’s first day of her new job.

Meagan’s heart beat a little faster.


Meanwhile in Richard’s office that morning...

“Gladys, get your ass bent over the desk facing the window!” demanded Richard.

Gladys stood up from being on her knees where she had been lavishing his cock with her tongue. She knew what he wanted when he had her bend over the desk facing the window. And she knew that she would be enjoying every minute of it as long as Richard would last. As she bent over she presented a gorgeous site of her firm ass highlighted by her white thigh stockings and a light blue garter belt holding them up. She had already discarded the matching bra and panties, along with her dress, at Richard’s direction earlier. She always got so turned on following his directions, stripping each layer for him. At forty-five years old, she was almost fifteen years older than he was, but he made her feel young and desired.

Richard moved to the side as Gladys moved past him to the desk where she bent over, resting her breasts on the shiny surface and gripping the other edge. He admired the view of her firm ass and the thought of parting her cheeks to get to her tight puckered hole made his rock-hard cock jump at that thought. Stepping around the desk, he removed a bottle of lube out of his desk drawer. Moving back around the desk he stopped behind Gladys’s ass. Reaching down with his left hand he slid it along her firm cheek until his fingers were deep in the crevice made by the part of her ass cheeks. He pulled on the left cheek spreading her open until he could see her puckered anus. Taking the bottle of lube, he squeezed a generous amount out just above her anus. The lube being a thick gel, it didn’t run down her ass but sort of oozed its way along.

Richard took the ring finger on his right hand and smeared the gel over Gladys’s anus. He slowly massaged around the opening, pushing gel into it until he pushed his finger into the first knuckle. Letting go of her cheek, he picked up the bottle that had been laying on her back and squeezed more around his finger that was inserted. He pulled it out and gathered a generous amount of the new application of lube onto two of his fingers. He pushed them back in her anus along with the lube. He continued to work them in and out in small motions.

Even though Gladys knew what was coming when she felt him separate her cheeks, the coolness of the lube still surprised her. Then his massaging of her anus left her softly moaning until he slid the first finger in. She had been fingered by Richard many times anally, it was still always the first entry that caused her to tense. Knowing she couldn’t stay that way, she concentrated on the sensations of his actions and was able to relax. As he continued to massage the lube into her anus, she began to moan louder as he excited her with his action.

Seeing Gladys had relaxed, Richard withdrew his fingers and was satisfied to see she was gaped open slightly. He knew the first penetration always caused her some discomfort, but that never stopped him from taking what he wanted. He took the bottle of lube and squirted a generous amount right her opening. He immediately placed his cock head against her and pushed into her anus, spreading it around his cock. Although Richard was not much longer than six inches, he was almost three inches thick, so he was stretching Gladys’s anus around him. He felt her tense and ran a hand along her spine, soothing her.

“I’m almost through, luv. Just a bit more. Relax for me.”

She made an effort to relax, looking at her own reflection in the window glass. He continued to apply pressure as she pushed out against him as he had taught her to do over there first few times of anal.

Richard suddenly felt her inner muscle open and his cockhead slipped past. Once he had moved beyond this hurdle, he steadily pushed his cock deeper, listening to Gladys moan in both pain and pleasure. As his pelvis touched her ass, he knew he was fully seated in her anus. He held still for a few heartbeats letting himself and her adjust to both the tightness and the fullness of the moment.

Picking up the bottle of lube, he squirted more at the point where his cock disappeared into her. He slowly started slipping his cock out of her, careful not to pull the head past her inner muscle. As his cock came out he took two fingers and spread the lube along his shaft. He then started pushing back in causing more moans to escape from Gladys. He continued until he was fully inserted again.

Stroking her back he asked, “Are you ready for more?”

With her head tilted so she could look back over herself, she said, “Yes!”

Knowing she was ready, he slid out part way out before pushing back in all the way. He continued this for some time, continually lengthening the strokes until he was pulling almost completely out and sliding all the way back in. Watching his cock move in and out of her, he would see the rim of her anus pull outwards as his cock did and then push inward as he went all the way back in.

Gladys raised up on the desk, moving a hand to her clit. She vigorously rubbed it in time to Richard’s in and out thrusts. It had the effect of relaxing her to his actions and also pushing her towards an orgasm herself.

Richard felt her raise up and knew she would be fingering her clit as he continued to fuck her ass. He could hear the moans emitting from her throat every time he drove his cock deep and yanked it back out. As soon as she started this he knew she would cum quickly causing her anus to become almost vise-like on his cock. He knew he was nearing his limit of stimulation as well and would probably be pushed beyond.

As if on cue, Gladys let loose a protracted moan and he felt her anus clamp down on his cock. He struggled to continue to slip in and out of her, but the increased resistance pulled his own impending orgasm from his balls. He slammed his cock hard and deep into her, forcing her to flatten out on the desk as he shot his cum deep into her ass. He stood there and shook as his orgasm passed through his body and he felt her shudder as well working through the end of hers.

Finally, completely spent, he pulled his semi-hard cock from her ass, allowing a small bead of his cum to slip out as well and run down her crack. Backing away from Gladys he stopped a few steps from her. Gladys recovering from her orgasm and his stood up and turned towards him. Looking down, she could see his cock slick with cum and lube. She didn’t hesitate before dropping to her knees and taking him in her mouth, licking and sucking him clean. When she was done, she stood up and moved to the red circle in the carpet about ten feet in front of Richards desk.

She stood there with her head bowed waiting for him to let her go. He turned and looked at her, taking in the sight of this woman who had so freely given herself to him so many years ago. It was she that set his sexually controlling nature free. Through all the women that had paraded in and out of his life, she always stayed loyal and serviced his needs in every way. He had offered her promotions and better jobs, but she always refused. When she had been ill for so long, she had gone and found Glenda for him. She had introduced her to him and instructed her as to what his needs were. Glenda had become part of his staff ever since. Finally noticing the top of her stockings were showing signs of being wet, he realized he needed to let her go and get cleaned up to start their day of business.

Walking over to her, he lifted her chin and kissed her softly on her lips and said, “You never need to bow your head to me, luv. Go ahead, get cleaned up. Go home if you need to change. Sorry, I messed up your stockings.”

She had felt the cum and lube mix run down her thighs, but she would’ve never have cared. Looking at him, “I have a clean pair. I will go and get freshened up. I’ll be at my desk by the time Meagan arrives. Are you going to greet her today or have me get her started? The Stuart account, right?”

Sitting down in one of the armchairs in front of his desk and not being bothered by being completely nude, he crossed his legs like he would anytime doing business and replied smiling, “Yes, the Stuart account. That should give her a taste of some of what will be expected of her.”

With the plans finalized, Gladys gathered her underthings and dress. She walked out the door towards the bathroom off the conference room leaving Richard relaxed in his armchair naked. As she crossed towards the bathroom, she could see that Glenda was at work in the outer office through the unfrosted edges of the outer doors.


Andy pulled up in front of the Whit building and jumped out to come around to open the door for Meagan but she had already beaten him to it. He grabbed the edge of the door and offered her his hand to help her out of the car. As she slid to the edge of the seat, her dress had ridden up her thighs just enough so you could see the very top edge of her stockings. This gave Andy a very nice view of her legs all the way to her thighs. He felt the stirrings in his groin but knew better than to do anything stupid.

“Thank you, Andy,” Meagan said standing up and smoothing her dress down.

“You're welcome, Ms. Lewis. Also, here is my card with my phone numbers for when you need me. I can usually be ready to go with ten minutes notice but if you can give me more that is better,” Andy said, handing her a card.

“Thank you again, Andy and it’s Meagan, got it?” she said smiling at him. Meagan slid it into her messenger bag’s front pocket and turned for the door on this first day of work.

She entered the building and headed towards the reception desk. As she approached, she saw the same man that had been on duty when she was there last week. When she stopped at the desk he looked up at her and started fishing around for something on the desk. Picking up an identity card, he said, “Here you go Miss Lewis, this is your I.D. card for the building. Ms. Gladys will take care of any other things you need. Welcome to the company. Just take the same elevator you used last week and it will take you right up.”

“Thank you,” taking a moment to look at his name tag, “Glenn,” she said to him.

Walking towards the elevator, she glanced at the I.D. card and realized it had a picture of her on it. It was a picture from the day of her interview but she could not remember having a photo taken that day. Then again, there was a lot about that day she couldn’t forget. Just as she neared the elevator the doors opened. Stepping in, she glanced at where you would hit a floor button and that was when she remembered that there had been no buttons to push. The elevator automatically started its journey upwards.

When it stopped and the doors opened, she could see into the same reception area Gladys had taken her to last week. The first thing she did was look down at the two red circles inlaid into the carpet. This had the effect of sending a warm flutter through her body that ended in her pussy. She wasn’t sure why but she did know the sensation felt good, not bad.

As she stepped out, Gladys was just coming through the double doors from the conference. She was busy buttoning up the front of her dress and didn’t notice Meagan at first. As she moved towards her desk, Meagan got the impression she had just gotten dressed. This caused another flutter to run through her body but this one ended in her gut.

Since Glenda was turned towards her computer and Gladys hadn’t noticed her, she said, “Hello Gladys. I’m here for my first day of what I hope is going to be a very exciting job.”

Gladys had just finished smoothing down her dress over her tummy and legs. She looked up at Meagan with a little sly smile as if she knew more than the girl did, saying, “Hi Meagan, we are so glad you decided to join us.”

Gladys sat down behind her desk and motioned Meagan to come over and have a seat that across from here. “Okay Meagan, I have some paperwork for you to sign and a security card for the office for you. I’m going to assume Glenn gave you the security card for the building?”

Meagan nodded her head, yes, holding up the card.

“Well, you won’t need that one anymore. Just keep it safe somewhere. This card,” Gladys held up a blue card with a stylized RWT on it for her to see, “will get you into the building, our offices and the records area.” Reaching out, she handed it to Meagan.

Gladys went through the other paperwork that was needed and had Meagan sign or initial anything that was required. When it was all done, almost an hour later Gladys stood up and Meagan did likewise.

“Now that we got all the legal stuff done, let me show you to your office.”

Gladys led her through the doors into the conference room and Meagan immediately looked at the red circle she had been standing in when Richard had asked her to strip for him at the interview. She then looked up at the double doors were Richard had disappeared to afterward.

Gladys kept moving but knew what was probably running through Meagan’s mind at the moment. After all, she hadn’t been the first girl to have an interview in here but was hoping she’d be the one to last. Moving towards a door on the opposite end of the room as the bathroom, she stopped waiting for Meagan to catch up.

“Okay Meagan, this is your office door. As you can see it has a security lock but any of the locks in here can be opened by your card, Glenda’s, Mr. Whit’s or mine, with the exception of Mr. Whit’s inner office.” With that, she swiped her card over the reader and the door clicked open. Pushing it lightly it swung open into an office. Stepping out of the way, Gladys let Meagan pass into the office first.

She was greeted with a terrific view out a wall of floor to ceiling windows. Centered in front of them was a beautiful ornate oak desk. Then looking around she took in the rest of the office. The place was huge, along the wall to the right was another door and Gladys indicated it was a private bathroom with a shower. Hearing this, Meagan had another flutter that ended in her pussy. Along the other wall was a set of double doors with frosted glass that Gladys indicated went into Mr. Whit’s outer office. Along the same wall was situated a small sitting area with a very nice couch and a few chairs. The rest of the office had the typical upscale office furnishings like shelves and file cabinets.

Meagan continued to take in the office as Gladys explained the doors but tuned out towards the end when she noticed the red circle inlaid into the carpet about ten feet in front of the desk. She stared at it letting her mind drift back to the circle in the conference room, wondering if she would be standing in this one soon, almost naked.

Suddenly she was shaken out of her thoughts by Gladys asking, “You have any questions about the office?”

“No, I think I can find my way around here. I wasn’t picturing anything this lavish though for my position.”

“Well, you’ll find out Mr. Whit treats his personal assistants really well. Now if you are okay, I have a file for you to review for Mr. Whit and as long as it is okay it will need to be hand-delivered to Mr. Stuart this afternoon. Andy can take you. He knows the building downtown. If you need anything just hit the button for the outer office.”

With that, Gladys indicated the blue file on the desk as being Mr. Stuart’s file to be reviewed and she headed for the door.

Meagan caught Gladys just before going through the door with a question. “Will I be seeing Mr. Whit today?” she said with a little catch in her voice.

“No, he will be gone for a few days this week. As I said if you need anything just let me know.” With that, Gladys was out the door.


Meagan laid her messenger bag on the corner of the desk and sat down in the chair. She spun it around, looking out the windows. She sighed and thought, ‘What am I getting into here? I thought I could handle anything but I’m not so sure now.’

With her self-reflecting done, she swiveled the chair around to the desk and picked up the file laying there. It had a note from Richard on explaining what she was to review. It laid out what was expected and what to do if something wasn’t right. Turning to the computer situated on the corner of the desk, she clicked on the mouse and was surprised when it woke up with ‘Welcome Meagan, Richard’ scrolling across the screen. Mentally kicking herself, she got to work on the file. A few hours later she was done and found the file met all the requirements listed in Mr. Whit’s instructions. She picked it up and walked out to Gladys and Glenda.

Standing there she turned towards Gladys saying, “This all checks out. Should I go ahead and take it to Mr. Stuart’s office?”

“Sure dear, would you like me to call Andy to have the car ready?”

“Yes, thank you, Gladys.”

Meagan walked back into her office and grabbed her messenger bag slipping the file inside and she went out the door heading for the elevator. As she neared it, the doors slid open and she stepped in. It was a little unnerving not to have to push any buttons though. She felt the smooth ride to the lobby and the doors opened. She started off across the lobby towards the doors and could already see Andy waiting by the car.

Opening the door for her he said, “Ms. Lewis.”

Looking up at him as she slid in, “Meagan!”

“Yes ma'am, Meagan it is,” he said smiling.

Getting in, he looked back towards her and asked, “Mr. Stuart’s office, correct?”

“Yes Andy, thank you.”

Meagan settled back in the seat as Andy navigated traffic. It wasn’t long before they were pulling up in front of about a twenty-story building. She looked out at it and just smiled. It was all modern with dark stone and glass.

Reaching for the door handle before Andy could jump out, she looked over shoulder and said, “I’ll be back shortly, Andy,” and with that, she was out of the car.

She stopped at the information desk on the ground floor and was directed to the fifteenth floor for Mr. Stuart’s offices. Getting off the evaluator she walked over to the receptionist and asked to see Mr. Stuart, that she had a delivery from Mr. Whit. She was directed down the hall where she came face to face with a woman a lot like Gladys. Explaining again why she was there, she was ushered into Mr. Stuart’s office.

Walking into the office one feature jumped out at her and almost made her stumble. There in the middle of the carpet was a blue circle, identical to the red ones in Richard’s offices.

Walking up to the desk she said, “Mr. Stuart, this the file Mr. Whit sent over to you.”

Looking up he replied, “Thank you and you must be Meagan? It’s nice to meet you in person, Richard told me a lot about you already. I think you’ll enjoy working for Richard, it has some unique fringe benefits.” He smiled broadly with that last statement. “Tell Richard I said hi when you see him.”

She said, “Okay,” but he had already started going through the file. Assuming she had been dismissed, she left and made her way back to the car Andy had waiting at the curb.

She slid in before Andy saw her coming and said, “Back to the office, Andy.”

On the ride back, she kept picturing the blue circle in Mr. Stuart’s carpet and his sly comment about the fringe benefits. She again wondered what she had signed on for by coming to work today.

They got back and Meagan went right up to her office. As she opened the door the first thing that hit her was the smell of flowers. Sitting in the middle of her desk was a huge bouquet of roses and wildflowers.

There was a card and she plucked it off reading it,


Welcome to your new job. I hope this first day was wonderful and I hope you have many more. I look forward to working with you and getting to know you MUCH better.


She moved around the desk and sat down thinking, ‘It wasn’t much of a first day!’

Meagan sat there for a few minutes looking over her desk and getting a little better acclimated to her new office. Standing up, she walked over to the bathroom door and opened it and just about passed out in shock. It was no office bathroom. It was all decked out like a high-end motel suite bath. She just shook her head and closed the door going back over to her desk. She looked at the clock and saw it was 4:30 already.

Not having anything else to do, she decided it was quitting time and gathered up her messenger bag and picked up the huge vase of flowers. She headed out towards Gladys and Glenda’s area. Stopping in front of Gladys, she asked, “Is there anything else I need to do today?”

“Not that I know of Meagan. I got a phone call from Mr. Stuart's office that he was thrilled to meet you.”

“I don’t know why. I didn’t do anything special while I was there.”

“He’s just that kind of guy. Would you like me to have those arranged and placed in your office for tomorrow or would you like to take them home?”

“I think I’ll take them home with me. My little apartment could use some brightening. If you talk to Mr. Whit, please tell him I said thank you for the flowers.”

“I sure will. See you in the morning.”

Meagan moved towards the elevator and it opened for her. It had just started moving when she remembered she hadn’t called Andy, but holding the flowers and her messenger bag, she couldn’t get to her cell. It would have to wait until she got out of the elevator. The door slid open and as she started looking around for a place to set the flowers down, she caught sight of Andy waiting for her. She headed for the doors and had a gentleman hold it open as she went.

Andy opened the door and helped her in with the flowers asking, “Good first day, Meagan?”

Waiting until he had gone around and got in replied, “Yes it was, Andy. Home please.”




This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © 2019
All works published under the author's name of Road_Runner are entirely of my own work. No part of this material may be reproduced or transmitted in any form or by any means, mechanical or electronic, or used in any other fashion without the express permission of the owner.

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