My Hot Boss’s first time anal experience

Works drinks shenanigans with my Boss, a true story by Kryz…

A few years backI was working for one of the larger Superannuation companies in the Sydney CBD.
Every month we would have extravagant “team building drinks” nights in one of several city hotspots.
I always liked attending these events, for the free drinks, dancing and eye candy of my fellow employees (Boys and Girls) letting their hair down.
Each month that year I had made a point of having a drink with my department head. He was technically my Boss’s Boss. He was in his mid forties at the time, so about 15 years older. He went through a nasty divorce at the beginning of the year (the source of a lot of water cooler gossip!) when his wife left him for another man.

He was a kind, funny guy, quite good looking and was always a gentleman. He was about 6 foot, a joggers body and always wore nice suits.

I had made my mind up for him to be a “project” to work on during the year... I should point out that Mr S. knew about my schemes and plans (we don’t keep secrets from each other. Secrets are what kills relationships!)
Each month at the drinks event I would make a point of having a bourbon with Scott* and a talk and a light flirt. I would find reasons to be in meetings he would be in, etc.

By September or so, we would have lunch together every other week at a Vegan diner. He would usually complain about how hard the dating scene was and how all the best Girls like me were spoken for.

I could tell he was interested in me in a very unprofessional way, so I ramped up the flirting, sending him some very suggestive signals.

Octoberfest rolled around and our workplace hired out an entire pub in Sydney for end of month Friday night drinks. I made sure to wear my little Bavarian servant girl outfit, my hair in plaits, stockings, etc.

The venue was dark and noisy, everyone was feeling no pain, the night winding down.

Scott and I were in a back corner having our customary drink together (Jagermeister instead of bourbon, in honour of Octoberfest)
I had been quite busy and popular on the dance floor in my outfit and had noticed Scott, noticing me, several times.

Full of Dutch (or was it German?) courage, I had decided tonight was the night Scott was getting lucky. I had been waxed that week and I was keen to get this particular bed notch cut.

Once I was able to see that nobody could see us at our booth under the stairs, we were alone at last. Well alone as a crowded nightclub full of work colleagues that knew who we were, could get....

I apologised to Scott abruptly for “neglecting to get him an Octoberfest gift”
He looked puzzled at what I was talking about, but his eyes widened when I sat up and slid my silky white panties off and presented them to him, asking if he liked them as a present?
He put them in his jacket pocket and stammered a thanks...
“Oh dear, now my pussy is cold, Scott. Feel it!” I said guiding his hand underneath the table to my eager snatch. Scott looked furtively around but wasted little time in fingering me. He seemed very taken with the clit piercing... (spoiler alert, my pussy wasn’t cold at all...)

“Now, you owe me a gift, Scott” I pouted.

“What did you have in mind?” he gasped as I ran my hand over the bulge in the front of his suit.

“How about you give me something sweet and salty to slurp down and we call it even?”

With that, I slid underneath the Table and released his hard cock. Not enormous, but clean and ready for attention, so I wasn’t complaining!

He threw his jacket over the top of my head and the table, making me giggle. Then I got down to action. Deep, throat filling action. Cupping his balls lightly and sucking him down greedily. The thrill of what we were up to was exciting both of us, and it was probably only a minute before he shot his first load in my mouth. I swallowed it like a good little bar wench and washed it down with my remaining Jagermeister.

Scott was still very keen to fuck me, so we arranged to meet at a hotel in Haymarket in forty minutes. I sent a text to Mr S. letting him know that I would be a little later than expected due to “something coming up ;) “ He knew what that meant.

Scott had booked the room and messaged me the room number.
I got some strange looks in the elevator in my outfit, but it was Friday night, so I figured I didn’t stand out too much. As I knocked on the door Scott opened it and almost dragged me in. We kissed passionately before he dropped to his knees and began to lick and finger fuck my pussy. He slid a cheeky finger onto my arse and rested it there and seemed surprised when I reached back and guided it into my backdoor.
“My Ex would NEVER let me even touch her there and I have ALWAYS wanted to try anal!” He said, looking up at me with pleading eyes.

I reached into my handbag and took a bottle of lube and stood him up. I covered his shaft in a generous coating of gel and then positioned myself on all fours on the bed.

“Then, Fuck my arse please, Sir” I requested coyly.

He wasted little time in easing himself into me, commenting on the tightness of it. He began to slide in and out grunting and giving me a light slap as he went...

“Fuck me harder, Scott!” I begged as my fingers frantically delved in and out of my snatch and rubbed my clit. He grabbed my plaits in one hand a griped my hip with the other. He was now pistoning into my arse, and I was loving every naughty second of my boss butt fucking me like he owned me. He gave me a firm slap every dozen or so thrusts.

We changed positions to missionary with my legs up, so he could play with my breasts and kiss me. He was a great kisser and smelled absolutely heavenly. He seemed to enjoy watching me finger my self as he rocked back and forth into my arse. He felt so great in there. I was so excited about finally getting to screw him that my pussy was creamy wet…

It was about ten minutes before he gasped that he was ready to cum...

Deciding that this whole experience was so nice and deliciously dirty, I gave him the full pornstar experience and told him that he could give me a facial - in fact I prettymuch demanded it... he pulled out, I hopped off the bed onto my knees and I jerked his cock off over my face, licking my lips and smiling up at him as he began to ejaculate hot sticky white cum all over me. He came in a torrent over my face and into my mouth. I kept working his shat until he dragged my hands away.

He fell back on the bed as I skipped to the bathroom and had a quick shower, before leaving to catch a Cab home. Another perk of the job!

I got to tell Steve all about my naughty adventure while He fucked my neglected pussy that night.

Things at work on Monday seemed a little weird at first, but then we fell back into a rhythm of all Buisness at work for a month, but every end of month drinks, we would rendezvous at the hotel afterwards and we would fuck like rabbits. Scott eventually moved to another company about 6 months later, and we sort of lost contact. I heard on the grapevine since that he got remarried, and I really hope that his new wife likes anal!

*name changed for his privacy