The Boss Gives It Up

The Boss Gives it Up Pt. 01

It is never a good idea to dip the quill in the company inkwell and date coworkers. Oftentimes, these liaisons occur spontaneously, and the regret is instantaneous. Sometimes, they can be very fulfilling. Adding additional spice is when my female coworker is cheating on her husband and must sneak around to indulge in an extramarital affair. The cherry on the cake is when she has a taste for kinky fetishes.

Our affair began at post-work drinks at the Mitre Tavern in Melbourne's CBD. At the time, I was having a torrid relationship with my next-door neighbour, who had the body of a porn star and the personality of a psychopath. We were not suited for anything long-term, but with the toxicity rising, I was looking for ways to extricate myself from her alluring web. Simone, my boss, had imbibed a little too much and disclosed to me that my co-worker, a woman, had caught her masturbating in the office bathroom with lesbian antics ensuing. Simone further disclosed that Amanda, the discoverer, had the hots for me.

These revelations made my head spin, but I did nothing with this intel in the following weeks. Life at work continued as usual, with my attention focused on exiting my domestic situation. At a subsequent visit to the Mitre Tavern one Friday, Simone approached and asked me if I was interested in Amanda. My response was non-committal, but I wanted to ask my boss if she was still flicking beans with Amanda.

"Nah," Simone answered, "We had a couple of follow-ups, but I prefer men."

Men? I wondered. Not my man? I gave little weight to her response initially, assuming that she was a hetero woman who preferred men to women, but a kernel of doubt popped in my mind, and I wondered if my boss was a player.

"Did you tell your husband?"

"Fuck no!" Simone chuckled, "I thought about what you said, but decided against it."

At the time of the disclosure, Simone had felt embarrassed at being caught, felt awkward engaging in girl-on-girl action, and felt guilty for cheating. I joked that confessing to her husband would be his wet dream.

"Maybe, but I doubt it," Simone replied at the time, "He's not that imaginative."

"Shame."

"Why is that?"

"Because if it were me, I would have..." I began before realising my full sentence would have been grossly inappropriate given the power dynamics and the working relationship, "Well, never mind."

Simone shot me a sly glance and a suggestive smile. I turned away momentarily as my cheeks burned with foot-in-mouth embarrassment.

"Mister," Simone said sternly and tapping my shoulder with an elegant finger, "Now you have to tell me."

Looking at Simone, her eyes betrayed a certain level of inebriation. So, I wondered if I spoke my mind as ordered, she would forget the next day.

"This won't affect my end-of-year bonus, will it?" I jokingly asked, "And no complaint to HR?"

"Of course not," Simone smiled, "Tell me."

Slightly reluctantly, but eager to see her response, I spoke my mind. To my surprise, Simone did not recoil, but her eyes widened, and she smiled with an alluring look.

"Really," Simone said, suggestively running her index finger down my chest, "That sounds good."

"But you're married," I said, emptying my glass, "So, it's just a fantasy."

"Maybe," Simone teased, "Maybe not."

"Meaning?" My cock was stirring.

Simone was not just my boss. She was a friend outside of the office. We shared a lot of non-work interests and would talk for ages about the history of Asia, which we had visited a couple of times.

I've worked for some hot bosses in my time, but Simone took the prize. Slim and tall with a natural D-cup chest, long flowing blonde hair, wearing minimal to no makeup in the office, she was severely educated, erudite, commanding and discerning in taste for the finer things in life.

She had been in a long-term marriage to a guy whom I had met on occasion. He worked in the financial sector doing M&A work. He was an affable guy, and the couple had two grown daughters. At the time of our dalliance, Simone had ten years on me.

"Meaning, I like the sound of that."

"Interested?" I asked, being a tad more confident in my approach.

Simone cocked an eyebrow, bit her lip and provocatively circled her glass of wine.

"Yes, I am."

"What about this?" I asked and tapped her wedding ring with my fingertip.

"It'll be our dirty little secret."

Simone was not aware of my domestic troubles, but if we went in her direction, we would be both cheating whores. Given how toxic my relationship was, and my desire to sever ties, my conscience was as clear as Simone's.

"And Amanda?"

"Forget about her," Simone chuckled, "I'm way better."

"Is that so?"

"You're the type of guy that can really scratch my various itches."

"And they are?" I asked, becoming seriously aroused.

"You'll find out."

We exited the bar discreetly and walked, hand in hand, back to the office. It was 9 PM, and the office was shrouded in darkness. On our level, Simone dragged me to her office and slammed the door. She pushed me into her chair, sat in my lap and kissed me furiously.

Hands roamed and squeezed body parts, teasing and arousing. Simone's lips were incredible, and her tongue was devilish. My cock was rock hard and pointing, through my trousers, towards her fuck holes.

Being my boss, I felt it appropriate - nothing was appropriate about this situation - to let her take the lead. She encouraged me to unbutton her top and free her magnificent breasts. For someone in her fifties, her titties remained remarkably firm and very sensitive. Sucking on those firm nipples brought her to a quick climax.

Next, I attempted to penetrate the inner sanctum, but was quickly disabused, with the well-worn first-date excuse that she was behind the red curtain. Simone did, however, slide off my lap and drop to her knees. Deftly unbuckling my trousers, she quickly freed by poor, suffering cock and took it into her mouth. I almost yelled with uncontrolled pleasure.

Her expert technique of using her lips, tight mouth, liberal use of saliva and the cupping of my balls had me lobbing ropes deep down her throat. Not a drop was wasted and Simone continued sucking, albeit at a lesser pace, post orgasm as I deflated.

"Did you like that?" She asked after smacking her lips and looking up at me with fire in her eyes.

"That was fucking amazing," I panted, spent and tired, "Never came like that before."

"Sweet and tasty," Simone cooed, "But my favourite worker, I have to get home else hubby might become suss."

This was fine by me since I had shot my bolt. Plus, by the time I got home, the foul temptress next door would be haunting hallways, cursing my absence. With any luck, the drugs would have knocked her out and she would become a Saturday problem.

The arrangement that was settled upon between Simone and me consisted of a Friday night office fuck, followed by two weeknight meets whereby we drove to an industrial area and had car sex. These nights coincided with her husband's personal commitments, which I wondered were extra-marital, that would have added a delicious irony to our situation. Weeknights also took my neighbour out of the equation as she was passed out on drugs.

At work, Simone and I used a WhatsApp connection to exchange racy banter that usually resulted in several risers out of me. We met several times during the week in one of the office's least frequented bathrooms, constantly worried about being rumbled by Amanda, which led to a dusting of additional spice to our dalliance. Sneaking around was exhilarating.

One Friday night, some months after our affair began, as Simone sat on my lap, both naked, dripping in sweat, nuzzling my neck, I asked about her kinks and fetishes.

"I thought you'd never ask," Simone teased, "You an ass man by any chance?"

"Honestly," I began, "I love ass and yours is particularly inviting."

"Oh, you like my ass?"

"It's like a Georgia peach," I replied, slapping a cheek gently, knowing exactly where this discussion was going in the direction I wanted, "You giving me your ass?".

"Not now, baby," Simone kissed me passionately, "Maybe next week."

We cleaned up and discreetly exited the office building and departed at Flinders Street Station. Upon returning home, my neighbour was otherwise engaged by some of her drug-dealing customers. Over the weekend, I hate fucked her while thinking of Simone.

The following Monday and Tuesday were frustrating days because Simone and I had a full calendar of corporate meetings and could not make time for some office fun. In a way it heightened the anticipation for our Tuesday evening car meeting where anal was on the menu.

My nerves were taut as I waited nervously in the car park, sat in my beaten-up Toyota Landcruiser, drumming the steering wheel with one hand and squeezing my rock-hard cock with the other.

Simone finally arrived, slowly driving her Mercedes up the road to our discreet meeting place. The night was humid, being a late spring evening. After parking next to me, Simone flexed her long, luscious legs, opened my car door to greet me with a passionate kiss. She chose to wear a sheer black onesie that accentuated her nipples and denim shorts perfectly sculpted to her round booty.

"Can I join you?"

"Of course."

We fucked in the Landcruiser for obvious reasons, space and adaptability. Leaving my car door open, Simone walked around the bonnet and climbed into the passenger seat. After an eternity of passionate kissing, Simone grabbed my hand and encouraged me to fondle her massive breasts while spreading her legs. I pulled down the onesie and exposed her breasts to the warm evening air.

Voluntarily, Simone undid the buckle of her jeans shorts and began playing with her clit before reaching over and squeezing my bulge.

"Get your cock out," She breathed.

I undid my jeans and shuffled them down my legs to give her easier access. Simone reached across and rapped her elegant fingers around my leaking shaft and roughly wanked me. At the same time, I reached across and slid my fingers between the onesie's gusset and roughly inserted them inside her. Simone's reaction was instant, and she arched her back in pleasure.

"Fuck me, yes!"

After minutes of breast fondling and pussy fingering, Simone demanded to suck my cock. She leaned over and took my twitching and leaking prick deep inside her generous mouth. Simone was the best cock sucker I have ever met, and I did not want to blow too soon before having some ass pie. She did her best to make me blow my stack.

Knowing I was holding back, Simone changed tack. Instead, she started coating my hard prick in dripping ribbons of saliva. Rubbing the viscous fluid all over and across my shaft, acting as a substitute for synthetic lubricant.

I was in no rush to interrupt this amazing action. However, Simone got to the boiling point. Once satisfied that my prick was sufficiently lubed, she released my cock from her mouth, turned around and began provocatively shuffling her short jeans down her legs. The black onesie g-stringing between her ass cheeks.

Pulling the flimsy material aside, Simone placed both hands on her ass cheeks and pulled them apart and then backed up against my dripping prick.

"I need you cock in my ass."

Turning around into a reverse cowgirl position, I pressed the glistening head against her dark pucker and allowed Simone to rest her weight against my cock. To my surprise, my shaft entered with little resistance, and we both let out a cry of surprise.

After a moment of adjustment, Simone placed a hand on my leg and began bobbing up and down as my cock buggered her most precious hole. The heat and tightness were intense and a completely different sensation from being inside her pussy.

I grabbed hold of the onesie and encouraged Simone's fucking motion. My cock looked amazing inside my boss' asshole. Placing fingers on each cheek, and pressed them aside so that I could get a better view.

"Give it to me, doggy," She demanded breathlessly.

Changing positions, Simone stood up and my cock exited her hole with a satisfying 'pop'. We changed positions with her climbing onto all fours in the back seat and me climbing onto the platform so that I could thread my cock back into Simone's asshole.

"Oh, fuck yeah!" Simone gasped repeatedly as my cock slammed deeply inside her funky hole.

By now, sweat was pouring down my head and chest in the late spring humidity.

"Fuck me, I'm coming!" Simone yelled while her face was planted on the back seat of my Land Cruiser.

I pulled out briefly as Simone came down from her anally induced cosmic high to finger her greasy hole.

"How was that?" I asked as my thumb explored her spongy bung.

"Amazing," Simone moaned, "I want you to cum inside me."

Not that I needed to be asked twice. I gingerly inserted my cock back inside my boss' hole and fucked away until I deposited an enormous load that would have been heard three suburbs over.

"Fucking hell, I felt that!" exclaimed Simone.

After an age I withdrew my limp cock. Simone's anal aperture snapped shut but I asked her to flex it. Like in the movie 'Alien' those weird corridors have those openings, the same with Simone's asshole. She pushed and flexed it until my thick funky seed spilled down her cunt and onto the seats. It was a magical sight.

Watching Simone's sphincter shoot out my jism over my car seat was sublime. Witnessing that buggered wrinkle expand and contract, was pure hardcore. She knew exactly what effect that would have on me, and I quickly rose to a renewed secondary hardness.

Begging for another go on her asshole as the last dribbles spilled out, Simone refused. Instead, she spun around, sat on the platform and took my shitty stick in her mouth and blew to a second climax, swallowing whatever was left in my balls with glee.

By this time, I was a physical and mental wreck. Sweat was pouring from my body, and my ball sack was non-existent. Simone spat out my deflated cock and ran her hands threw her blonde hair letting out a loud sigh of contentment.

"Fuck me, that was good!" She exclaimed, "Good sex, as usual."

"It sure was." I groaned, slumping against the side of the Land Cruiser.

Simone glanced at her Omega Seamaster watch and checked her phone before announcing that she had to go home before her husband returned home.

After cleaning up, we hugged and prepared to leave.

"That was fantastic anal," Simone said, "I want more."

"So do I."

"Really," Said Simone, "There's a lot more we can do with that."

"Ah, I guess I'll have to wait for that."

"Yes, you do." Simone leaned in and kissed me before sliding into her Mercedes and driving away back to her husband.

I slumped against the Land Cruiser and revelled in my good fortune. Fuck me, Simone was a fantastic lover. However, she was not a long-term acquisition; she would never leave her husband for me, so I had to enjoy this affair for as long as possible.

Retrieving my phone, I saw several messages from my unstable neighbour demanding to know my whereabouts. It was 9 PM, and I would be home in 30 minutes. While she was demented, her body and appetites could not be ignored, and as I drove home, I was about to violate my own rules, again.