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Chunkypete Member Since October 16, 2018

A straight guy gets his anal cherry taken by his Boss

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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 looki

Nate sets me a task to complete while he is away on business.

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Nate was away on business, but that didnt mean I could rest on my laurels, he had set me a task.

The message came through while I was on a night out with my housemate who of course had no idea that I was now into cock and was being fucked regularly by our boss Nate for cash and other benefits.

GET FUCKED BY SOMEONE TONIGHT, FILM IT AND SEND IT TOO ME.

I was stunned, he really wanted me to be fucked by someone else? But how? I was out with my house mate and no where near a gay club, how could I explain it?

A plan formulated in my mind, I hit the internet on my phone and posted an ad on craigslist, I needed a top to fuck me super discreetly at home, downstairs while my housemate slept

Just the thought of it had me nursing a semi in the club....

We got home in the ear

A young chubby straight lad has his first gay experience

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I had always been a little curious as most young men are even if they admit it or not. Tall for my age i stood around 6 foot tall even at the tender age of 18.

At this time i hadnt had much luck with girls, id lost my virginity of course but i wasnt very experienced overall. I started a new job and i was getting along well with everyone and working hard, i had noticed the boss's extra interest in me.

It started off as innocent accidents, you know he would brush past me from time to time, a smirk on his face. His name was Nathaniel and he was the owners son, he stood slightly taller than me, he was built but not fat like me.

I hadnt thought about trying anything with guys for a long while, but there was something about him and the way he looked at me.

One day as i was clocking