• From shitting on a co-worker’s computer to screwing the bosses wife, the Planet Dolan
crew re-enact some of the best true stories from our subreddit about the craziest things
our bosses ever asked us to do.
I’m Nixxiom and today I’ll be your narrator.
Number 9 was submitted by Doe-dippitey Hellbent
One time, Hellbent worked at an auto body shop.
While he was working on a car, his boss went up to him, which didn’t surprise Hellbent
because he was known to be a lazy employee.
Instead, his boss seemed nervous, saying very quietly, “Will you fuck my wife while I
watch?”
Hellbent politely declined, but watched as his boss went to one of the other guys.
He heard one of his co-workers yell, “Hell yeah!
She’s hot!”
Hellbent believes that everyone but him fucked the boss’s wife, since his boss would go
to an employee every once in a while to ask.
Number 8 was submitted by Drawkillfoxygamer360 Dean, the Time Wanderer
Dean was working the night shift at a business office when his boss went up to him.
He asked him to shit on his co-worker’s computer.
When Dean asked why, his boss told him that he wanted him to quit, and that he would pay
him 700 dollars if he did it.
Since he needed the money, and despite the co-worker also being a friend, Dean did what
his boss asked him to do and took a shit on the computer.
The next morning, his co-worker saw the pile of shit on his computer and immediately quit.
Number 7 was submitted by Idx_K3 Grgak
One time, Grgak worked at an adult video store.
His boss e-mailed him one day, asking him to go to his house and bring him some things.
Grgak thought his boss had been hurt, because he told him to go to grab some bandages, a
bag of pills, and a grocery bag on his stove.
Then he went to another address that his boss gave him, which was to another adult video
store.
When he got there, Grgak was directed to go to the VIP room, which was where his boss
was.
He entered the VIP room and saw a hole on the wall.
It turned out that his boss had stuck his dick into the hole… but found out too late
that it had been ‘treated’ by a guy.
When he found out, his boss had some kind of reflex, getting himself stuck in the hole.
So, he told Grgak to push it out from the other side.
Not wanting to touch his boss’s dick, he went to his boss’s side and pulled instead.
It eventually “popped out” and, while doing so, his boss hurt his dick and told
Grgak to bandage it, which he did.
The pills in the bag were Viagra and other pills that stopped erections.
The grocery bag was full of magazines and some weed, too.
It’s a job that Grgak now leaves off his résumé.
Number 6 was submitted by FluffyFurry_097 Andiemations
Andie once worked in a restaurant with one of her friends, who worked as a waiter.
One time, he dropped the food on the floor.
When Andie went to clean it up, her friend ran away… and her boss came up and got angry.
He blamed her for dropping the food, and punished her by demanding that she eat the food from
off the dirty floor.
If she didn’t, then she would be fired.
Since she was broke, Andie decided that it would be best to obey her boss.
Her boss was surprised that Andie ate all the food that was dropped, and gave her 100
dollars.
Number 5 was submitted by We_girls_game Honeybits
When she was 16, Honeybits worked at Wal-Mart.
It went all right for the first couple of weeks, until one day when her boss pulled
her aside.
Confused, she asked him why he wanted her.
He told her to be quiet and to not ask any questions.
That scared her.
He brought her into his office and told her to sit down.
Her boss proceeded to tell Honeybits that his girlfriend broke up with him, and that
he missed her every night.
Shocked, and thinking he wanted her to be his ex-girlfriend’s replacement, Honeybits
yelled and jumped out of her chair… but her boss grabbed her arm and pulled her back
down.
He continued to explain that he didn’t want her that way, but instead told her to bring
the female customers into his office so he could have sex with them.
Terrified, Honeybits nodded and left.
She then pulled out her phone and called the police.
Number 4 was submitted by Squeak_Attack Cidius
Back in high school, Cid worked at a taco stand in an amusement park.
A week after he started working there, his boss threw a box of gloves on the counter
in front of him.
He told Cid to fill five with sour cream and five with ranch dressing.
Thinking it was a joke, Cid ignored him, but then his boss came back about ten minutes
later and demanded to know where his gloves were.
Nervous, he did what his boss told him to do.
He tied the bottoms of the gloves shut before putting them in the refrigerator.
It turned out that his boss only wanted the gloves filled so he could squeeze the contents
of each one into the condiment bottles.
Although Cid thought it was a smart idea in hindsight, he still wonders why his boss didn’t
just tell him in the first place.
Number 3 was submitted by PrestontheWerewolf14 Derek
One of the craziest things Derek’s boss asked him to do was go to the diner next door
and tell the waitress to put her hand in his pants.
His boss offered him 100 dollars to do it, so Derek went to the diner and told the waitress
the situation.
Strangely, it turned out that the waitress was his boss’s daughter.
She put her hand in his pants in a heartbeat, and Derek received his 100 dollars.
Number 2 was submitted by 4Corry MKyleM
MKyleM worked for a boring insurance company when his boss came up to him one day.
He told MKyleM something surprisingly interesting.
It was something that probably wasn’t too interesting to the average person, but in
a boring insurance office it was cool.
His boss told him that he wanted him to sing to his plants and fish.
Just for singing country music to his boss’s plants and fish so they would grow better
and stay healthy, MKyleM got some good bonuses.
Number 1 – What was the craziest thing my
boss ever asked me to do?