Old Boss, New Job

Old Boss, New Job

Sometimes it's good to fall on your ass in front of the boss

Many thanks go to RF-Fast and Just918 for their editing and suggestions that enhanced the story. Any bad grammar left is wholly on me and my artistic style.

LEGALESE: Don't read this if you are underage, if it is illegal in your area, if it is offensive to you, or if you cannot distinguish fiction from reality. This is a work of fiction. All characters active are of the age of consent.

I don't consider myself a writer or author, I'm a storyteller. So please take that into consideration when you read it, it should be read like someone is telling you the story. I am not now, or never have been, an English major. So synonyms may be wrong, and the grammar may not be correct, but it is like people really talk. I've never talked to someone that had perfect grammar.

There may or may not be discussion of political issues in my stories. If you are a Snowflake that feels you need to be protected from any mention of politics or reality in general, then click the Back button now, and never attempt to read any of my stories ever again. You've been warned. For those of you that do like what I've posted so far, thank you and I hope you enjoy reading it as much as I did writing it.

To all the true Americans in one uniform or another, THANK YOU FOR YOUR SERVICE! And remember, thē greatest enemy of the United States Constitution and your individual freedoms and rights is not China, is not Korea, is not Russia... no, the greatest threat to America is the American Mainstream Media, their corruption, their dishonesty, and their rabid political bias toward the American Socialist Democrats.

John Stuart Mill once said, 'Bad men need nothing more to compass their ends, than that good men should look on and do nothing.' Whenever possible, I will do my best to shine the light of truth on the bad people. I write for my enjoyment and for the patriotic people that like it. If you don't like how and what I write, oh well. Don't read it. My feelings won't be hurt.

Copyright (c) 2022 by Acup

- - -

Old boss, new job,

MUCH better benefits...

- - -

I could feel his eyes on me as I typed. I had to get this out before they got here, and he was making it difficult to concentrate.

I had made the last of the corrections when I saw his shadow approach as he stepped up behind me. Felt his hand lightly touch my neck as his hard dick pressed to the back of my arm.

I tried to control my sigh, but it didn't work.

My hands were trembling as I managed to move the trackball enough to get it saved as his hand slid slowly down inside my dress. Clicking on the icon as his fingers found my aching nipple.

I tried not to press into his hand too much, but his chuckle said otherwise.

I felt his other hand come down outside my dress, and I knew it was coming, the wait killing me.

He got good grips on my nipples and pulled them out through the holes in my bra and nipped my earlobe.

I shuddered and came just a little, grinning at knowing I was going to be spread in a little while for him to lick and play and probably make me scream a few more times.

I grinned even harder, sometimes it is really good to fall on your ass in front of the boss.

* * *

I had been with the company going on ten years now. I started out as general secretarial in the pool on fifth, but with the luck of the draw and a few lucky breaks, I was now Andy's personal assistant.

Of the ten VP's he was... safe. Fifty-nine compared to my thirty-two. Happily married compared to my still single and hunting. He was a decent looking guy, and complimented me on my outfits and such. Not overtly so, but just enough to tease my over active imagination. He would glance at my boobs when he thought he could get away with it, and if it had been a while since I got laid, I might even give him a bit more to look at.

I might get a bit of a look from some of the other PA's once in a while, but I wasn't some old married woman, so what the hell. In spite of what they wanted to imply, the company didn't really have a written dress code. And I would occasionally take a few liberties with the unwritten one.

I had a couple of special versions of the same dress. The normal one was as is off the rack. The 'special' ones had slightly thinner material or no inner liner. Enough to let a bit of texture through, maybe even a nice silhouette if back lighted. The wrap around versions were a bit less wrapped around to show a little more cleavage and leg. I had one of them that was a LOT less wrap around. I had to put little snaps in to keep it at least halfway decent.

I wore that little blue number to work a total of twice, and both times back when I was still on the fifth floor. The first time was a Friday when I was supposed to have a hot date after work. I got a lot of looks from the guys and a few glares from the women, but I thought I was going to get well fucked that evening so I didn't care. Hell, I hit the bathroom and lost the bra on the way out. Boobs were bouncing and nipples dancing as they tried to get up and out of the neckline. I drove to the bar with one tit out just because I didn't want to tuck it back in. With 32B's bras were always optional.

I sat there for two hours, and wound up with 'Mr. Right Now' for the night after I had too many drinks. Thank god we went to his place, no way in hell would I want him to know where I lived.

The second time was a few months later just before I moved upstairs, and I would have sworn at the time that dress was cursed. This time I was anticipating another hot evening, just different undies. I had a nice thin bra, satin under cups and sheer lace upper over skimpy crotch less panties. All in blue to match the dress.

The day was not going that great, and I had major computer problems early on so even with barely taking breaks, I was running about half an hour behind. I had finished the document and hit print about fifteen minutes after everyone left for the day, I thought.

I went to the copy room to catch the collated presentations, standing there getting impatient, and rocking back on my heels like I do. Problem was I was actually in some three inch heals instead of my regular shoes.

After one too many times rocking back, one of the heels said fuck you.

All of a sudden I was falling back and flailing. I stepped back with my other foot, and caught the hem of the dress as I fell. That in turn popped the strip around my waist and all the snaps opening me up to the world. Sitting on the copy room floor in crotch less panties and lace cup bra with my dress wide open around me.

I managed to get standing, kicking the other fucking shoe off, holding my dress closed enough to turn around and look out into the hall, and gave a big sigh. No sign of anyone. I grabbed my bag from under my desk, and got my morning after clothes to change into.

I at least called him to tell him I couldn't make it. Unfortunately he didn't seem all that disappointed. Never heard from him again. I repaired the dress and hung it in my closet as a reminder to keep my wild notions in check. Well kind of.

We had casual Fridays, and some of us took advantage of them more than others.

Most of the time we just dressed a little less fancy, but some of the fall Fridays, I'd do the sweatshirt over snug jeans, or lately over leggings. Most of the time black, but I've occasionally worn some lighter colors.

If I'm in a randy mood, I'll make sure they are the ones that snug up tight in my ass and pussy. And I've found a few thin stretchy panties that have some really slutty VPL. I literally heard Richard gulp behind me when he came into the copy room as I was reaching up for some three part paper.

I went back to my desk and sat cross legged so I could run my big pen up and down my cleft imagining what he was thinking looking at my barely covered ass.

Now don't think I was the only one. At any given time there are around five or six of us spread out throughout the building. Hell, Ginger down in receiving looks damn fucking hot in her skinny jeans and denim top. I'm not into girls, but those big boobs bouncing around in there even get my attention.

As long as we're not too overt, it's no harm no foul. An extra button or two undone near the end of the day is just smiled at.

Oh that fucking smile. That cocky little grin that I would just love to sit on. There is usually a slight wave of silence as Carl walks through the office. He has the whole Sam Elliot look and then some. Like Road House cocky grin look. His voice just a little lower and gravely. Hearing it makes you wet. Him talking to you makes your nipples ache. Well mine anyway.

And he was leaving.

His wife had fooled around. They were in the final stages of divorce, no kids, and he was going off to open his own shop. We had about three months to fantasize about him.

Five weeks later it was casual Friday, and the building had been having AC problems. So instead of a light sweatshirt over my bra and off white leggings, I had a thin old tan tank top and a thin stretchy bra. I had to tie the tank top shoulder straps up to keep from showing bra band and most of my side. The good and bad of that is that it left my pussy and ass fully exposed if I was up and walking around. I did my best to make consolidated runs.

I did make an extra pass by Max's desk just to see if he would gulp looking at me again. I got a nice tingle when he didn't gulp. He sounded more like he was choking on something. I got wet when I saw the window reflection of him sticking his head out just past the edge of the divider to get a good look at my ass. I made sure to take the last few steps with legs wide imagining him looking at my wet spot.

I was sitting at my desk after afternoon break fantasizing about Carl running his hands over my body, running my big pen up and down my cleft pressing it in as much as I could get away with...

"Hey Vicki?" I heard that gravelly voice behind me startling the hell out of me.

"ACH!" jumping and launching my coffee cup skyward. Luckily it wasn't very hot, but unluckily it landed on me as it came down. "God damn son of a..." I stopped to see Carl grinning and trying not to. A moment later I knew what he was trying not to grin at.

I felt that coffee soaking through my top and bra. It was making it cling to my skin and turn translucent I'm sure. I kicked my head back, "Oh god."

He held up a tiny coffee napkin, "Need to dry off a little?"

I snorted, then we both laughed.

"Go dry off, I'll hand you a dry shirt through the door."

The bad part was, the way he was looking at my boobs, I wasn't so sure I really wanted a dry shirt.

I put my arm across my chest and made my way to the ladies room with several looks and chuckles.

I had my top and bra off and was wiping my boobs, the leggings had only gotten a few spots, when there was a knock at the door making me screech. I heard his laugh, and an arm come in with one of his denim shirts in hand.

My nipples ached and my mind wanted him to come in and put it on me... eventually.

I slipped it on, and was drowning in it, the tails well down to my thighs. That was good because I could smell his cologne on it and the soft inside was doing wonderfully terrible things to my nipples. Any shorter and there was a damn good chance of someone seeing the wet spot that was forming again in my swamp of a crotch.

I stepped out to see him waiting and smiling, then chuckling. "A little big on you huh?"

I pulled one side out to snug the other side up, "Room for at least two of me in here." I let it go kinda quick realizing I was almost hanging my boob out the shifted neckline.

He followed me back, and I wiggled a little extra knowing he was there. I shoved my rolled up top and bra under my desk, "Now what was it you wanted?" I almost leaned forward, but that would definitely have had me hanging loose in front of him.

He chuckled, "Well I was going to ask you if you had any evening free this week to discuss a possible business opportunity." This was said in a much quieter tone than normal.

I glanced around, "Like?"

He smiled that smile that was really ramping up my wet spot, "Not here. Whenever you're available."

"I don't have any hard plans for the next few days." Well other than shoving my big dildo in hard and fast imagining it was you. My nipples were starting to ache again.

"After work okay?"

I looked down and tugged up on his shirt I was wearing, then looked back at him looking at my body. I really needed to cross my legs HARD, preferably with my finger, or better yet, my vibrator against my clit.

He looked me in the eyes with those light gray eyes, "Just a quick informal meeting. If it's something you'd be interested in we can discuss it further down the road a bit."

I shrugged because that was all my brain was capable of, barely able to ask, "Where?"

"How about The Bistro after work? I'll buy you dinner and we can go from there."

I just nodded. I was imaging him having my sloppy pussy for dessert, and maybe breakfast.

"Okay, I'll see you there." He turned to walk back to his office, and I bit my lip as I watched his ass, then dashed to the ladies' room to Jill off while huffing cologne from his shirt.

I was a total mess walking to The Bistro. Part of me fantasizing about Carl, while another part was curious about why me.

He already had a booth in the back, and rose to greet me. I leaned over and slipped in the other side, only realizing as I sat that I probably gave him a good look of at least one boob if not both.

We ordered and ate, and while his attention was elsewhere, I undid one more button. I was now unbuttoned right down to my nipple line. His shirt wasn't gaping open, but he already knew I was braless. I could feel the little glances at my cleavage every so often.

With dinner finished he sat back and just looked at me. "So, I imagine you are wondering what this is all about?"

I nodded.

"Well, a little background first. You know about the divorce, right?"

"Common knowledge."

He sighed, "Well the reason she said she cheated was I was boring."

I about spit my wine at him and started coughing.

He smiled. "I was raised to respect women, and I guess I was always worried about stepping over the line. So I never really pushed things with Evelyn."

I nodded again.

"So, when I open my new office, I guess I'm looking to go the other direction."

"Like?"

He took a deep breath, "I'm looking for a PA that thinks a little bit of sexual harassment might even be a good thing."

I was glad I wasn't drinking my wine.

"A woman that takes a lusty undressing with my eyes as a compliment. That if I find her bent over the filing cabinet in a short dress, would enjoy a light caress of her ass."

"Oh..." I was starting to get tingly imagining his hand on me.

He took a deep breath, "A woman that thinks one of those tiny little blue wrap around dresses might even be a bit over dressed."

I was coughing, then looking at him bug eyed.

"That was the hottest thing I have ever seen. And who knows, if it happens down the road, I might have helped you to stand up, then made a detailed inspection of that lovely behind of yours to make sure you weren't injured."

Fuck, now I was getting wet and very tingly imagining his lips all over me, "And afterwards?"

He shrugged, and looked down at my boobs, "Depends on where the detailed inspection started." Then he smiled, "Something like that."

I gasped, then grinned. Without realizing it I had brought my hand to my boob. I glanced around, then undid one more button and pulled his shirt outside my boob.

I heard him suck air, "Damn," he said softly.

I let it go almost but not quite giving in to the urge to bare both boobs, and it just barely covered my nipple. "How long do I have to decide?"

He was still looking at my almost bare boob, they were both aching. "Few days would be nice. If not, then I'll have to go to the next woman on my list."

I snorted. "So you've already asked Ginger."

His head snapped up from looking at my boob, then he smiled. "No, you are the top of the list."

That made me even more tingly.

"And her wife might take offense to her being groped by a mere man."

I gasped, "I didn't know she was a lesbian."

"Think about it. If you can deal with that part, we can discuss the rest."

Deal with it? I wanted him to reach in and play with my boobs right now! We got up, and he took another good glance down his shirt at my boobs when I got up. I stopped him and gave him a soft kiss. "I will definitely think about it."

It was all I could think about driving with one hand in my crotch. I managed to make it home without cumming, but these leggings were fucking soaked.

I ran to my bedroom, the leggings came off, and I was diving for the nightstand drawer. I flopped back on the bed and drove that big dildo hard and deep in my sloppy cunt. Jamming it in over and over while imagining it was Carl above me. Watching my boobs bounce as he went all cave man in me. I twisted my nipple and came around that dildo as my legs snapped shut.

I laid there panting in afterglow, reaching down and pulling the shirt collar to my nose to inhale his cologne as I squeezed down on that dildo imagining it was Carl. I think I knew the answer when his eyes locked on my boob at dinner. All too many men are into big boobs. Some will tolerate small ones. Very few actually like them, and Carl appeared to be one of those select few.

The only thing I wore around the apartment all weekend was his shirt, and my pussy was almost raw by Sunday evening I had abused it so much dreaming it was Carl instead of my dildo. I had even used the small one in my ass and nearly passed out imagining him taking me that way.

So how to do this.

I went through all my outfits, selecting and tossing out different combinations until I had what I wanted.

Monday and Tuesday I would wear some nice to very nice outfits. A little short in the skirt, but tolerable. A little thin and loose in the top to let me move, but again tolerable. Wednesday I'd tell him yes, oh boy would I tell him yes.

From the outside it looked perfectly professional, a jacket over a nice dress. I had to keep the jacket on all day, because it wasn't exactly a 'nice' dress underneath. There wasn't much up top outside of what you could see in the open jacket. More like a very skimpy halter doing an impression of a dress shirt. Even with my small boobs it was hit or miss if it covered as I moved.

I waited until a little after lunch, slipped my thong off under my desk, and went to his office with some folders in my hand.

He looked up as I came in, and smiled when I turned to close and lock the door. I set the files down, then hitched up the waist string and spread the neckline a little before I turned back to him to remove the jacket. I was all but falling out of the neckline.

His jaw literally dropped. I picked up the folders and slooooowly walked up beside his desk, then leaned forward and just as slooooowly set the folders on his desk.

His eyes were dancing on my body. With the waist hitched up and neckline opened my boobs were hanging in midair. I glanced back, "No filing cabinet in here, but will this do?"

His eyes immediately went to my ass, then his hand slowly reached for it. We both moaned as he lightly cupped my ass, then gave it a slight squeeze. I pressed back into his hand a bit, and he reached for the other cheek giving it some nice attention.

"Your hand is in the wrong place." He froze. "It's on the outside."

I heard him gulp, and my pussy was quivering.

His hand slowly went down my ass and the back of my leg to the hem of the dress, then began coming back up my thigh. Before he had even reached my pussy, he was lifting my dress with his wrist. I groaned when he got a good grip on my ass knowing my crotch was completely exposed from the back.