Society & Culture Awkward Working situations

[HolyRioli]

The most awkward situation for me was as follows.

I shagged my boss who was this awesome MILF. She was married to, which made it even kinkier. We shagged a few times over the course of a few months. Anyway, one night a few months later I picked up this hot young chick and she took me back to her place. I was a bit apprehensive because she said her parents were there, but she said it was cool, because her parents were fairly open-minded and didn't care if she brought guys home (she was 20.)

So, we get to her place and her Mum is there and guess who her Mum was? My boss. She smiled at me, introduced herself, offered me a cup of tea, and basically put on this massive act, so as to not give away the fact that she rooted me.

Strong play

 

[Unrivaled Mach]

The most awkward situation for me was as follows.

I shagged my boss who was this awesome MILF. She was married to, which made it even kinkier. We shagged a few times over the course of a few months. Anyway, one night a few months later I picked up this hot young chick and she took me back to her place. I was a bit apprehensive because she said her parents were there, but she said it was cool, because her parents were fairly open-minded and didn't care if she brought guys home (she was 20.)

So, we get to her place and her Mum is there and guess who her Mum was? My boss. She smiled at me, introduced herself, offered me a cup of tea, and basically put on this massive act, so as to not give away the fact that she rooted me.

Wow, full of win + awkwardness, well done

 

[Ed_Gein]

I'm a gardener, work in a team of four. We have a computer in our office which is shared by all. One of our team starts work an hour before us, so he has the place to himself from 6am until 7am. One morning there was pubic hair all over the desk, and pr0n in the recent documents. Awkward, especially considering one of the other guys frequently browses the internet while eating his lunch.

lawl.

The most awkward situation for me was as follows.

I shagged my boss who was this awesome MILF. She was married to, which made it even kinkier. We shagged a few times over the course of a few months. Anyway, one night a few months later I picked up this hot young chick and she took me back to her place. I was a bit apprehensive because she said her parents were there, but she said it was cool, because her parents were fairly open-minded and didn't care if she brought guys home (she was 20.)

So, we get to her place and her Mum is there and guess who her Mum was? My boss. She smiled at me, introduced herself, offered me a cup of tea, and basically put on this massive act, so as to not give away the fact that she rooted me.

Full of win!

I don't have much to add. But know a guy who just recently got the sack because he said to a fellow worker that the team leader had a "face like a wasp"

 

[Shimmy90]

The most awkward situation for me was as follows.

I shagged my boss who was this awesome MILF.

This!!!!!!!!!!! Not to the extent of porking her, but my manager is a dead set milf. Working in office environments is pretty cool, especially when she comes in wearing office attire.
-The business skirt
-shirt..etc
I purposely excuse myself from my desk to ask her for "Office equipment" which force her to bend over narrow places.

yeah im sick.

so what.

 

[cplfc]

Working in a hospital as a doctor we comes across many awkward things, but over time you become desensitised to it.

Recent example. Was doing the ward round with my registrar (who is female) and we had to do a PR exam (rectal examination) on a male patient in his fifties. This is a regular event and procedure goes something like this.

The man gets on his side. Pants down. Gloves snap. Squeeze of lube. Penetration.

It wasn’t really awkward until the guy says “it’s like a role reversal”.

 

[Caesar]

Clearly he's a medical malpractice lawyer.

 

[RU_]

Caesar never fails to amaze me, haha.

 

[Tigger Please!]

why do chicks insist on showing so much cleavage? It's not fair, how am I supposed to work with those delicious clefts tantalizing me all day??
apparently saying, "if you don't tuck those things away i'ma have to take you out the back for a good rogering" is considered "sexual harrasment" in the work place.

 

[Simple Jack]

why do chicks insist on showing so much cleavage? It's not fair, how am I supposed to work with those delicious clefts tantalizing me all day??
apparently saying, "if you don't tuck those things away i'ma have to take you out the back for a good rogering" is considered "sexual harrasment" in the work place.

lol'd hard.

 

[Power King]

strong thread so far

The most awkward situation for me was as follows.

I shagged my boss who was this awesome MILF. She was married to, which made it even kinkier. We shagged a few times over the course of a few months. Anyway, one night a few months later I picked up this hot young chick and she took me back to her place. I was a bit apprehensive because she said her parents were there, but she said it was cool, because her parents were fairly open-minded and didn't care if she brought guys home (she was 20.)

So, we get to her place and her Mum is there and guess who her Mum was? My boss. She smiled at me, introduced herself, offered me a cup of tea, and basically put on this massive act, so as to not give away the fact that she rooted me.