Bobby Gets Lucky at the Office

Story Info
Bobby gets lucky with two hot MILFs.
3.7k words
4.18
73.8k
18
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

The Day I decide I Loved my Job and would never retire...

Well to be fair I knew I really wanted work right from the interview.

My Interviewers were two totally hot busty MILF's!!

Mrs. Hettler was super sexy in that naughty mousy librarian way. At first glance she wasn't much to look at, but with her quick wit and contagious smart ass sense of humor she had me relaxed enough to notice that she was hiding quite a hot body under her clothes. My other interviewer Mrs. Cummings was a brunette she also was wearing not very revealing clothing but I had a suspicion that she was a knock out underneath the office attire.

They were both plenty attractive but they both wore more make-up than I like, but then I go for more of that au natural look. I have always had a thing for older women.

These two hotties not only made me excited, but after a couple of ice breaking stories and their expressed interest in me as an employee I loosened up enough to even flirt a little. I think I ended my interview saying something like

"Anytime I can spend time alone with you two lovely ladies."

which I think made them both blush and giggle.

I was hired by them trough a temp service in January.

Up here in northern Wisconsin in January women bundle up and hide all there lovely curves, well mostly. I was lucky enough that each of them at one time or another wore fairly tight fitting sweaters that showed off Mrs. Hettler's at the very least D cup and Mrs. Cummings's DD cup I haven't really measured them yet.

But then summer came and WOW! Like butterflies coming out of cocoons the women up here shed there clothes. The ninety degree weather and humidity help get them into really skimpy things and my supervisor was no exception.

I used to frequent Mrs. Hettler's office quite often that first year because I didn't and still don't know the in and out's of our software as well as she does. I remember the first time she wore her short flared jean shorts and a tight yellow T-shirt.

Loose interpretations of a business casual dress code are a really nice benefit of working at a small company.

I came into her office that morning and her computer faced the inside of her cubicle so she would have to swivel around in her chair to talk to me. I had the hardest time not staring at her gorgeous breasts and my eyes kept wondering up her thighs.

I had to stare her in the face and concentrate really hard so I didn't get really hard.

A few days later it was the ALL staff meeting and which means all 12 people of which 3 were hot women I haven't even mentioned Mrs. Stacy our receptionist and the rest are men.

So I and a few of the younger men had showed up early and somehow the ladies came up and one of the guys said "You know who has a really huge rack but hides it all the time is Mrs. Cummings"

I said

"Yeah but I think Mrs. Hettler is hot too."

They kind of looked at me funny but I am more of a living breathing horn dog than anyone I know just ask my wife.

So as if to answer our prayers when the meeting started Mrs. Cummings decided she needed to take off her sport coat, I'm not sure but I don't think I was alone in my momentary jaw drop eye popping stare at her luscious melons!

For a long time I only had fantasies about banging Mrs. Hettler, Mrs. Cummings or our receptionist on their desks or after a game of strip poker in the conference room or something. One hot summer day though that all changed.

I try to keep my perversity under control but some times it gets the better of me and has caused me problems even with my marriage, lucky for me I am married to the most understand women in the world.

I wasn't getting enough sleep between late night on-line gaming, college and full time work I had been EXTRA, EXTRA horny.

So at risk to my employment been surfing fairly risqué videos on YouTube.

As can often happen in a small office when anyone can walk into your cubicle I think both my supervisor Mrs. Hettler and Mrs. Cummings the HR manager walked into my cube not only when I had a massive hard-on but when one my partially averted second monitor was playing some naughty secretary video or something.

After this had happened a few times I was not surprised and mostly worried when Mrs. Cummings said I should come to her office.

So I prepared myself for the possibility of getting fired, swallowed hard and walked sheepishly into her office. She asked me to close the door and sit down. Unknown to me at the time my supervisor was listening in on the phone over speaker phone.

Mrs. Cummings stood up from behind her desk and looked at me very sternly with her hands on her hips and I thought to myself oh crap what has my overactive libido gotten me into now.

She began

"It's come to my attention that you have been viewing some very inappropriate videos at your desk."

She paused waiting for me to confess which I always do women have crazy control over me.

"I, yes I, have and I am so sorry if you need to fire me I understand"

To which she replied smoothly

"Well let's not be hasty, you are one of our better hires, you are always here and on time, and get your work done in a timely fashion and I have never had to discipline you for anything before."

I thought for a moment when she said the word discipline I saw a spark in her eye

"Mrs. Hettler and I have not yet determined what your punishment will be but you WILL stop watching those videos immediately."

I felt a huge relief I had been sweating bullets and was thinking things like

'Oh shit! How am I going to explain this to my wife?'

Before my mind could get out of that vortex she said

"Upon observing this behavior I happened to notice that your taste in videos seemed to be older married women."

I just didn't know where this was going or what to say so I just sputtered out

"Um yes"

"Well..."

She was now sort of pacing about the office now and taking off her sport coat she sat behind her desk again

"Mrs. Hettler and I were considering having you work on a special project as a repercussion for your actions."

"Sure anything I'll do anything!"

She smiled and leaned back in her chair for the first time I notice that her button down was so tight that from the side you could see her bra because the shirt was barley able to restrain such a mighty force as those mountains.

"Very good that will be all for now we will contact you with instructions for completing the special project."

I tried not to seem like a blabbering idiot, but between her shirt and my relief, I was stuttering towards the door saying

"Oh thank you, thank you, I will do anything."

Just as I put my handle on the door she said

"One more thing,"

When I turned around she had apparently had enough time to unbutton her blouse.

There they were bouncy and full and barley contained in a white lacy brassier, I stuttered again and gulped

"Yes what can I do?"

She asked

"Tell me do you find me attractive?"

I think she saw her answer before any words came out of my mouth I had a big bulge in my jeans.

She looked over her shoulder and said into the speaker of her phone

"I think he will be able to fill our special project needs quite nicely Mrs. Hettler!"

Mrs. Hettler's voice came over the phone

"Good, good I am getting wet just listening!"

That is when I knew work was going to change forever.

As I turned to leave her office I heard her Mrs. Hettler say

"Can you send him to my office I'd like to inspect his capabilities?"

I was still headed for the door as my hand reached for the handle Mrs. Cummings said

"One more thing you naughty boy, don't ever let me catch you looking at those other women again, oh and Billy close the door on your way out I need some privacy."

In my disbelief at the current situation and trying to figure out how I was going to walk past the Male owners office and conceal my raging hard-on I almost stumbled into the door while replying

"Yes Mrs. Cummings." she said

"Call me Cathy, now go."

Thank Goodness I usually where my XL hooded sweat shirt I was able to pull it down to conceal my rock hard cock as I staggered to Mrs. Hettler's office.

When I entered her office I had an idea of what was coming so I closed the door right away.

She was standing there with a wooden ruler in her fist that was resting on her hip she had a matching fist on her other hip. She was looking hot but pissed, she had that angry school teacher look and there she was in all her beauty.

She started giving me a stern lecture about the company policy and how I ought to be reprimanded. She was talking a little loud then I realized that was because the owners' office was right next door. This became very apparent as she put down the ruler unzipped and stepped out of her tight shorts. The whole time she is giving me the third degree, I was a little bewilder by the visual counter point, and caught my self drooling a little.

Realizing that here I am staring at a glimpse of sweet creamy thigh and pink panties of Super mom, Boy Scout troop leader, scrap booking and now cougar out to measure my capability. She came around the desk and wriggled up on to her desk and pulling my chair closer she put a dainty elegant foot on my bulge and started rubbing it, I came in my pants instantly. She realized what had just happened and with a wicked grin she said

"That's all for now Billy."

As she dressed I began to leave in awe I mumbled

"Thank you Mrs. Hettler"

To which she replied "Call me Heather please you big dirty boy!"

Again I closed the door and stumbled down the hall. I had to get to the bathroom to whack off or I wouldn't be able to sit at my desk. After blowing my load all over my hand and cleaning up I made it back to my desk still in a daze of my new work environment.

A few moments later the receptionist paged me to the conference room. When I got there I was greeted by our new receptionist Mrs. Stacy. Mrs. Stacy was a young single mom with a nice ass. She was chatting with our former receptionist who retired to go back to school she was another MILF, who often reminded me of Janeane Garofalo she had the same sexy short hair and black glasses. Did I mention I have a thing for MILF's in glasses... I digress.

Anyway it was an informal visit they asked if I would come in and close the door and help them set up the A/V cart.

After closing the door and setting up the cart they said they had something to show me.

I sat down as the hot young one bent over and insert the tape in the VCR as she did her short skirt slid up just enough for me to get a flash of panty.

As the TV came on I could not believe my eyes there I was on the screen jerking off in the bathroom stall. I must have turned a million shades of red. The girls just started giggling.

Finally I couldn't take it anymore and asked if we could turn it off.

Mrs. Jenkins the former receptionist said

"Well we can if you like, but if we do that you might not get to see us naked."

For a moment I just sat in stunned silence.

Then the younger one put her hand on my thigh and said

"Or if you would like to do that for us in person we might get naked even faster!!"

So with my cock just barley being settled down, I decide what the hell.

So I stood up undid my jeans and started playing with myself. They started undressing each other in between giggles and rubbing their crotches. I was soon at full attention again. I couldn't believe the day I was having, and then remembered I better check the lock on the conference room door.

So just as things were getting interesting over the intercom came a page for me to handle a technical support call with a client.

Not wanting to leave I said

"Ladies I think I have to get that call."

Well Mrs. Jenkins was having none of that

"Then you will just have to take the call here, we are SO not done with you!"

So with my pants around my ankles I sat down and grabbed the phone. Mrs. Jenkins hitched up her skirt and hopped on the table in front off me and started stroking her panties with her legs spread wide in front of me.

This was making it really hard to concentrate on the call, to make matters worse I suddenly felt the gentle brush of hair on my inner thigh. As I looked down Mrs. Stacey was teasing the tip of my solider with her long brown hair.

I had been managing the phone call fairly well, until Mrs. Stacey licked the under side of my crown.

I swallowed hard and asked the client if I could call them back after I did some more research on my end.

Standing up Mrs. Jenkins hooked her fingers into the waistband of her soaked panties and dropped them to the floor.

That was all it took I felt my balls twitch and just as Mrs. Stacey slipped her wet mouth over my tip I unloaded.

Mrs. Stacey had just gently taken hold of my nuts so she knew it was coming so she slurped down the first spurt and then leaned back and I shot the rest of my seed on her perky C cups which she rubbed all over her breasts and then started licking her fingers.

Mrs. Jenkins was still in motion she hooked her arms under Mrs. Stacey's armpits and with one fluid motion picked her up swung her around and put her on the table.

Mrs. Stacey quickly assumed a from behind position waving her scent in the air as Mrs. Jenkins pulled down Mrs. Stacey's dripping thong.

Mrs. Stacey's swollen wet pussy was mostly bare; there was a neatly kept V of mouse brown pubic hair that crowned her now on display throbbing sex.

I wasn't sure what was happening, since this morning I had not been in control.

I had been informed that I was to be some sort of play thing for the two highest level women in the office, and now I was in some sort of black mail induced ménage a trios, with the new and retired receptionist.

I was not sure I would be able to satisfy the current ferocious MILF's as well as know how or what was expected of me.

Mrs. Jenkins the older of the two put my worries from my head when she pulled my chair forward placing my face about a 12 inches away from Mrs. Stacey's swollen and hungry vagina, then quickly stepped between us and with a deft hand she reached between her leg's and guided me into her hot sex.

As if by the flip of some invisible switch, in the brain that lives below my belt, the one that gets me into trouble all the time, my rock hard cock took over.

The horny little bastard, my cunt hungry cock went flying into action! My pussy crazed cock sending signals to my body on what to do, to make this as exciting and rewarding for the 3 of us.

With a quickness that caused Mrs. Jenkins to moan softly, I grabbed her two nice ass cheeks and kept her from impaling her self on me.

I began gently teasing by lifting her up and down gently so just the head of my cock was barley pushing on the entrance to her magic kingdom.

I let the ridge of my crown just inside and gently back out so that it was teasing her tightening pussy lips. This brought Mrs. Jenkins to a new level of wetness and anxiousness she began to try to thrust her self down on to me.

Over the delicate line of her delicate back I glimpsed the source of the low moans in the room.

Mrs. Stacey was bucking her hips forward trying to fuck Mrs. Jenkins's tongue deeper into her now noisily wet flower.

This brought me into a new realm of hot and bothered.

I felt myself stiffen and swell, and I was reaching a second explosion.

Much to Mrs. Jenkins pleasure I could not stand the teasing any more and I pulled her down hard on my shaft and that was all it took, I could feel my cum splashing off her cervix and splash around filling her cavern.

Mrs. Jenkins clamped down hard and with her Kegel muscles she milked the last of whatever I had left into her vagina and then let out a moan.

I felt her back arch and her legs quake. From her inner thighs a rapidly ascending, to her already fiery hot cave, came another more intense wave of heat and as she trembled she removed herself from Mrs. Stacey and bracing her self with one hand on Mrs. Stacey's ass she plunged a finger into the prone Mrs. Stacey.

They both gasped and groaned and my nose was assaulted by a new tidal wave of their scents colliding in the air and filling conference room with and even denser fog of the smell of sex.

I collapsed back in the uncomfortable conference room chair feeling totally spent. I felt my own thighs get drenched in a mix of Mrs. Jenkins and my juices.

I also felt my little man begin to fade in erectness, Mrs. Jenkins must have felt it also because she hopped off of me and said to Mrs. Stacey

"I am afraid honey, if you are going to ride that sweet cock you better lick the sweetness of my pussy off poor Billy."

Being the spry extremely athletic league volleyball player Mrs. Stacey launched her naked lithe body from her prone position and on to me.

With her wet bush straddling my stomach she slid down my front leaving a wet sticky trail of her juices on my chest, stopping her self so my cock was resting by her tight buttocks.

This new smell of her sweet peach and the thought of Mrs. Jenkins licking her to get her this wet and I felt my cock twitch yet again.

Over Mrs. Jenkins shoulder Mrs. Cummings voice said

"Well Heather it looks like he may still have the stamina of youth to fulfill our needs!"

I had not heard them come into the room.

However I seemed to be alone in my surprise.

I was just about to throw Mrs. Stacey off of me but instead what I saw there in the open doorway made my jaw drop.

There was Mrs. Cummings in a hot and naughty lavender lacey corset with matching thigh-high stockings and matching garter belts.

Behind her Mrs. Hettler had her right hand in Mrs. Cummings lace panties and was pinching Mrs. Cummings left nipple between her thumb and index finger.

Unbelievably my cock was at full attention yet again and pulsing.

The throb did not go unnoticed as Mrs. Stacey stood up and turned around and slid herself on to my cock while leaning down to lick my seed from Mrs. Jenkins dripping pussy.

In between groans I managed to sputter out my concern about the open door.

Mrs. Cummings said

"Not to worry Dirty boy I sent them all home an hour ago."

Feeling another surge of heat engulfing my cock I squeaked out my other concern

"My wife she could stop by anytime!!"

To my horror a voice in the hall said

"I'm already here dear"

I swallowed hard and began to push Mrs. Stacey off me and made a vain attempt to reach for my pants.

I could not believe what I saw next.

My voluptuous BBW wife with her glorious 36 DD's her perfect heart shaped ass, came into the room in a transparent black negligee that draped off her perfect and rock hard nipples.

"Relax dear; this whole thing was my idea. I figured if you thought you could handle more than I can offer we had better experiment!"

I felt a hand tighten at the base of my cock and I felt myself stiffen even more as it twitched and pulsed.

I could feel my balls begin to tighten.

I opened my eyes and to my confusion I was in my bed.

The hand I felt on my, so rigid it hurt, penis was my luscious BBW wife smiling down at me she leaned in and whispered

"Goodness big boy what were you dreaming about?"

Before I can answer she gives me another squeeze and as her lovely red hair gently tickles my abdomen she says

"Feel like getting lucky? Or do you just want go back to your dream?"

I can only let out a grunt as she flicks her tongue over the slit in my tip licking up the precum. I arch my back hoping and yearning that she will oblige me with a blow job.

My wife is not big into blow jobs but when she does they are amazing which she attributes to tips from her gay friend that she wanted to date before he came out to her.

12