Story Details

A straight guy gets his anal cherry taken by his Boss

Chunkypete on Anal Stories

It had been a few weeks since my boss Nate had made his "offer"

i knew he was itching for a reply but business had called him away, it was a Saturday night and i was out with mates in the centre of town.

More than a few drinks and some recreational drugs later i glanced at my phone and saw a notification of a text from a number i didn't recognize, i opened it and struggled to focus on the words.

IM IN TOWN IN A HOTEL
TIME FOR YOU TO MAKE A CHOICE
YOUR ARSE OR YOUR JOB

Nate


My heart skipped, he was in town!? i replied quickly to find out where so we could talk

he replied almost instantly with the address and before i even knew it i was strolling past the reception like i owned the joint, i exited the lift and stumbled along the corridor checking the room numbers looking for the one i needed.

I knocked lightly and a call came from inside "Its open Scott!"

I walked in, the room was magnificent, befitting his stature and monetary means, i rounded a small corner and saw the beautiful bed. Id stayed in hotels before of course but nothing like this, my eyes moved from the bed to a plush chair in the corner of the room where Nate sat smirking that smirk of his.

"Would you like a drink?" He asked silkily

i shook my head and stood like a deer in headlights, a million things rushing through my mind, what was i doing? what happens if i do this?

Nate could sense my discomfort and gestured to the bed.

"Take a seat there"

I sat down opposite him, i didnt have a jacket, only my button up shirt, nice jeans and smart shoes from my night on the town.

I was searching his eyes looking for a clue on what i should do, he seemed to notice.

"Ok Scott, im sure you remember our encounter a few weeks ago in my office?"

I Nodded slowly

"So have you come to a decision?"

I looked into his eyes and i saw the hunger, i looked down at my feet and mumbled "Im not sure"


Nate shifted slightly in his seat and spoke softly almost fatherly

"Lets sweeten the deal, rather than threaten your job how about i make you an offer?"

I looked up and met his gaze "What offer?"

He could hardly hide his sense of victory as he spoke

"Well, as you know i have a wife, and you have a girlfriend so we want to keep this little arrangement as discrete as possible, how would you feel about being paid? handsomely i might add"

My mind raced, i have had alot of money troubles and Nate was rich beyond belief, he could have any man or woman he wanted, but for some reason he wanted me? the fat hairy guy from his warehouse?

I was jerked back from my thoughts as Nate spoke sharply "I have a meeting tomorrow morning, so you cant be here long so either leave, or present yourself to me"

I was stunned, the change in him was so quick and so aggressive, so dominant...i felt my cock twitch in my jeans.

i stood up slowly, i thought about leaving and just taking my chances, but something inside me wanted this and wanted it bad, i turned from him and began to slowly slide my jeans to my ankles.

I bent over the bed my fat arse presented to my boss, i didnt hear him stand but i felt his hands grabbing my arse cheeks, before i knew it i felt my boxers being pulled down and i was spanked hard.

i didnt make a sound, then he hit me again, and again eventually a moan escaped my lips

"Oh, you like that?" i could hear the smirk in his voice

Suddenly i felt his weight upon me as he leaned down to whisper in my ear "This first time wont be pleasant but i will make it upto you down the line, i dont have time to be gentle or patient"

I struggled but he pushed my head into the bed roughly and growled like the dominant animal he was, i submitted and raised my arse higher.

I was still drunk so when his finger found its way into me it didnt really hurt, i knew he was being rough but i forced myself to relax into it, it felt ok actually.

i felt his finger slide out of me and i heard his zipper go down, i felt the tip of his massive cock press my arsehole and i tensed up.

"Shhhh no no no relax" he purred in my ear

i tried to relax, the head was in, he moved it deftly in and out of my fat arse, teasing me, readying me for his full shaft.

His hand moved over my mouth and held it tight, i barely had time to register what this meant when his entire cock was rammed deep inside me, i let out a cry but it was muffled against his strong hand.

The pain was intense at first, but i began to ease into his long deep strokes, i could hear his thighs slapping into my arse as he pounded me, my cock began to harden.

He let go of my mouth and pulled me back into a proper doggy position, my decidedly average cock sprang to attention.

I moaned loudly, each thrust making me realize what a slut i was.

"Oh my god, so so tight" Nate moaned as he pounded me harder.

My eyes rolled into the back of my head, i let myself go completely, before i knew it my cock was spurting hot sticky cum all over the bed, i had never experienced an orgasm like it, i exclaimed aloud before my body gave out and i fell limp onto the bed.

Nate followed me down, his cock still deep inside me "oh no scotty im not done with you yet"

He mounted the bed and really went to town on my broken body, then i felt it

His massive cock seemed to stiffen and get even bigger!, followed swiftly by wave after wave of hot cum shooting deep into my arse, it seemed to never end!

I felt his weight lift off me, i heard him get dressed and approach the door

"This room is yours, im elsewhere, See you Monday...Your mine now"

As the door slammed shut i realized that i was, i was his slut and my god was it good.

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