My Job Doesn’t Suck, But I Do!

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By Lauren McAllister

For my 45th birthday, I decided to go back to work.  My husband makes a good living but one doesn’t like to feel totally dependent.  Plus, the kids were both away at college so I found myself more or less “at liberty”.  While sitting around the house masturbating all day was fun, I didn’t really want to turn into one of those women who ends up in a Motel 6 under her tennis instructor out of boredom.  I’d already made the mistake of letting my masseur eat me out.  Even though I’d had a few drinks at lunch with the girls beforehand (and the orgasm was so intense it gave me the squirts), I should have known better.  Yes, it was definitely time to get my still shapely butt back into the workplace before I really did something stupid.

Executive assistant had a nice ring to it.  Alas, you have to be able to type and spell for a job like that.  Bank tellers need to know all kinds of stuff.  Can you believe you actually needed a license to sell real estate?  I’ve lived in houses all my life, I should know how they fucking work. After several weeks of unsuccessfully pounding the pavement, and dozens of disheartening interviews, I ended up at the DeTwine Technology Company.  It’s not nearly as grand as the name would have you believe.  Robert DeTwine was a twenty-two year old (he looked more like a 12 year old) computer whiz who ran a one-man business out of a loft downtown.    

            Bobby poured over my exceedingly slim resume.  “You haven’t done much have you?” he rhetorically inquired.

            “I raised two children,” I responded with a smile.

            “We don’t have much call for that here at DeTwine Technology,” he smirked.

            I got up (perhaps I could learn to flip suspect meat at a White Castle).  “Well, I’m sorry for taking up your valuable time.”

            “Sit down Grandma, I was only joking.”

            Grandma!

            “I’m only 39, you little shit,” I rudely lied.

            “Listen, what I need is someone to answer the phone for me, make the coffee, fetch my lunch and shit like that.  It pays 700 bucks a week.  Interested?”

            I was a little take aback.  Could I really work for this impudent and insulting infant?

            “Now, I’m not a huge fan of paperwork, so you have a choice.  You can either take the seven hun in cash and keep it all for yourself or you can make me fill out all those forms and give half of it to Mr. Taxman.”

“I’ll take the cash,” I heard myself say.  “When do I start?”

            “Well, I’m a little hungry right now,” he said, tossing seven hundred and twenty dollars onto his desk, “So, why don’t you trot on down to the Sandwich Barn and get me a veggie roll?”

            And that’s how I started working for a tactless hipster who was barely out of diapers.  I spent the rest of the day making coffee and watching him leer at me between phone calls and spirited games of Fruit Ninja. 

            Robert was not what you’d call a “by the book” sort of boss.  “Nice outfit,” he smiled.  “I can see right down your top when you lean forward.”

            “I don’t believe you’re allowed to say things like that,” I mildly huffed.

            He shrugged.  “You have a very acceptable set of jugs, Mrs. Ahern.  There, is that business-like enough for you?”

            Okay, I’ll admit that I smiled.  He had a weird sort of adolescent charm.  Plus, he was absolutely right about my jugs.

            A couple of weeks went by and Bob would do his teenage flirt routine and I would pretend to be annoyed.  All things considered, I quite liked the job and I became quite fond of him.  He was marginally funny and had that 22 year-old unstoppable life-force which was a refreshing change from the tired, middle-aged hubby I had waiting for me to cook supper at home.    

            One day, Robert closed a really big contract and took me out for drinks in the afternoon to celebrate.  He got completely shitfaced and put his hand on my knee several times.  I didn’t see much harm in it so I let him fondle my patella while he downed yet another crantini.  Bobby also doubled my salary and spent an extended period of time informing our waitress about how exemplary my work had been as his assistant. “She’s never, ever brought me a sub-par sandwich,” he laudatoryily slurred.  

            He was so pie-eyed by then end of our celebration that I was afraid to put him in a taxi.  It took me about 20 minutes of remarkably patient questioning, but eventually Einstein remembered where he lived so I could drive him home.  Upon reaching his apartment, he immediately proceeded to vomit in a disorderly manner.  I mean, it was all over him and half of the furniture in his living room.  God knows how I managed to get his big floppity drunken body into the bedroom but, in the end, that turned out to be the easy part.  Removing his clothes was nigh on impossible, not to mention thoroughly disgusting.  I decided to take all my clothes off before attempting it.  There were two very good reasons.  Number one – he was in absolutely in no condition to see me sans attire.  Number two – there was no way to put that messy inebriated lump of flesh into bed without being contaminated by large and rapidly cooling outcroppings of puke.  At least if I was naked, I could take a quick shower before heading home (he was going to have to clean up his own damn furniture). 

            Taking off his underwear was a revelation.  For a geeky guy, he was packing a substantial wad of manhood between his legs.  Okay, I’ll admit it; I reached down and held his big hunk of penis and nutsack in my hand for a second or two.  It was larger soft than most cocks I’d experienced at the very apex of arousal. 

So now, Mr. Boss Man was lying on his back and snoring like a fairy-tale mountain troll.  I was just about to put on my clothes and leave but decided I had better roll him over onto his side, just in case the idiot upchucked again and choked on it.  So, I got up on the bed and just grabbed one more handful of that sizeable cock (since I was never going to get to see it again) before shoving him into a non-asphyxiatory position.  Gosh, his man wand had a lot of heft to it.  I wondered how often he got to use it. Being fabulously rich, I was guessing it didn’t often go short of company.

“And who the hell are you?” a voice bellowed from behind me.

My vagina practically shot up though my throat, I was so startled.

“I, ah….And just who the hell are you and what are you doing in Robert’s bedroom?”

“I’m his girlfriend.  I live here.”

Oh fuck!

The next morning I slunk into work at 8:45.  My plan was to make the coffee (which I’m sure he was going to need more than oxygen), write a very contrite note of resignation, and run off home for a good cry.

“Good morning,” came a hungover voice from behind Robert’s desk.

“Oh hi!  I didn’t think you’d be in this early,” I feebly stammered.

“I’ve been here most of the night.  My girlfriend threw me out.”

“Really?”

“It turns out, she came home and found a naked woman in my bed with me.”

“Uh, yes she did.  But there’s a perfectly good explanation for that.”

“And this naked woman had my penis in her hand.”

I paused.  “There’s a relatively poor explanation for that.”

Bobby bounced up from behind his desk and grabbed me.  Before I knew what was happening, I had his tongue halfway down my throat.  I’m rather ashamed to say that I returned his lingual fire.  A few seconds into our most unbusiness-like smooch, he had his hands all over those “jugs” that he professed to admire.  My nipples almost ripped through my bra and blouse to cheerfully meet his exploratory fingers.  This was so wrong.  He was younger than my son, for crying out loud!  Alas, sometimes when things are that wrong, it just makes it all the hotter and if my vagina was any barometer, this unforgivable affront on wholesomeness and decency was absolutely scorching.

Bob lifted me up onto his desk and spread my legs forcefully.  The hem of my short skirt was pushed right up to my hip joints.  What panties I was wearing (I’ll admit they were pretty skimpy) were yanked aside to give him full and unfettered access to my swollen and undulating quim.   Robbie took hold of his long, thick shaft and pressed his astounding manhood against my ludicrously wet womanhood.

A thought crossed my mind, as I spread my legs even wider to receive him.

“If you’re going to fuck me in the office everyday, I want fifteen hundred dollars a week.”

 “I’ll give you two thousand.”

“Then I’ll also suck your cock and throw in some anal.”

“Deal!” He pushed the head of his knob into me.  That alone practically made my hair stand up on end.  If I’d have known huge schlongs were this much fun when I was single, I would have made it a condition of going out with me! 

The sensual overload of having my cunt stretched to the very limit as more and more of his penis penetrated my inner sanctum was breathtaking (Though, I did wonder, after about 7 or 8 inches of that monster, how the hell I was ever going to fit it all up my ass.).  I wrapped my legs around him for balance while I undid my blouse and bra.  Bobby went after those tits like my nipples were made out of bacon bits.  His tongue circled my areola and his teeth nibbled tenderly on my nips as the last couple of inches of his giggle stick made themselves at home inside me.

I had to hand it to him, for a super geeky techy, he really knew how to fuck a woman.  Once his King Kong dong was fully ensconced in my cock cave, he started to pump that sucker right up into my Fallopian tubes.  Base, primordial noises started to leak out of me.  I bit down hard onto his ear lobe as he continued to try and cut me in two with his massive Johnson. 

“Jesus fucking Christ!  Fuck me!  Fuck me, Mr. DeTwine!”

I could have called him Bobby (our relationship had become a wee bit more informal by this point) but when you’re being screwed by your boss on his desk, it was way hotter to refer to him as Mister.

He grabbed my ass cheeks and really started to ram it into me.  I was being completely filled up with his meat hammer.  His long hard thrusts were like nothing I’d ever experienced.  I could practically feel the tip of his dick in the back of my throat.  My cunt became as tight as discount shoes and I began to drool all over my own breasts.  That’s when I pretty well I lost control of everything.  The climactic build was fucking staggering.  Every muscle in my body felt like it was going to snap from the tension.  My clit and vulva were having the daylights pounded out of them.  One last monumental cock-wallop and I exploded.  Streams of girlie cum squirted of me like someone had stuffed Mentos and a Pepsi up my pussy. My cock-cave and womb contracted to the size of a singularity and then burst forth throughout my entire body.  I grabbed onto Bobby’s derriere and pulled every last nano-meter of his wad inside me as I continued to soak us both in a veritable fountain of my orgasmic liquids. 

As my epic, blinding spasms began to subside; Robert quickly yanked his righteous rod out of me and jerked-off all over my naked stomach and skirt, adding huge dollops of creamy spunk to our salty, soupy sea of sex.  And then he stuffed it back in!  The shock and force of his unexpected vaginal return set off a second major gut buster.  I must have been getting pretty loud because guess who ran in to see if someone was being murdered. 

Jessica, the dreaded girlfriend just looked disgustedly at the two of us conjoined and snarked, “I don’t get it.  What does an old woman like you even see in this loser geek?”

 “The same things you do, honey,” I snarked right back.  “His money and his dick.”

Well, Jessica knew exactly what I was talking about because she fell on the floor laughing.  We’re great friends now.  I service Mr. DeTwine’s every need and comfort at the office and she handles the big guy’s joint when he gets home.  Girls have never been my thing, but on his birthday and holidays we treat the lucky shit to some simply amazing threesomes.  And I have to admit it; burrowing into that pretty little snatch of hers with my tongue is a little slice of heaven – especially when I’ve also got my boss’s eleven inch doowanger up my ass. Yep, I finally let him up there and somehow it all seems to fit, though, my husband does wonder why I spend some nights sitting on ice and smelling of Anusol. Hey, us dull old lady’s sometimes suffer from sore bums. Cut the girl some slack!

The End

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Copyright Lauren McAllister 2022

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