Disturbing Things My Boss Has Said: Part 40
Me: Thus far this year, I've not had any meat.
Boss: Oh yeah? Want some sausage?
Me: Goddammit.
Disturbing Things My Boss Has Said: Part 39
Note: Because of the heat, my boss is wearing a t-shirt that he has rolled up and modified into a tank top.
Me: Why are you wearing your shirt like that?
Boss: So my arms can breathe. Does it make me any cooler? I don't know. It's mind over matter. It's like my penis. If I shave my pubes, does it make my penis bigger? No. But when I walk in front of the mirror naked and see that little stub, I feel better.
Me: ...
Disturbing This My Boss Has Said: Part 38
Boss: Today's the day that I make your butthole bleed, Josh Richey.
Me: ...
Boss: What do you think about that?
Me: I have no comment on the matter.
Disturbing This My Boss Has Said: Part 37
Boss: Do you want to know how you can tell that I respect you guys?
Us: ...
Boss: After I get done pissing in the sink, I wipe my pubes off for you.
Disturbing Things My Boss Has Said: Part 36

Me: If they don’t stop beeping their horn, I swear to God I’m going to…
Boss: Stick it up their ass?
Me: …yeah!
Boss: And then lick it?
Me: …no :-\ 

On one hand, I can’t believe that there’s been 36 of these things. On the other hand, working with the guy every day for years, I can’t believe that there’s only been 36 of these things.

If you’re new to the blog, check out the previous 35 by clicking here.

Disturbing Things My Boss Has Said: Part 35
Boss: I just want you to know that, 100%, I'm not even kidding, I'm not wearing any underwear today.
Me: It's 94 degrees, why aren't you wearing any underwear?
Boss: BECAUSE I DIDN'T HAVE ANY CLEAN IN MY DRAWER THIS MORNING! I even rubbed my naked ass on my wife last night in bed to let her know.
Me: Was your wife awake?
Boss: I don't know. I called her this morning and said "Just so you know, I have water running down my ass today because of you..."
Me: ...
Disturbing Things My Boss Has Said: Part 34
(Context - Just had a very scary moment at work where something very bad nearly happened)
Boss: ...were you scared?
Me: Yeah, I think I might've shit my pants.
Boss: I did that on Friday. Just be glad that you're not stuck in traffic for two hours between Crittenden and Dry Ridge like I was with no air conditioning. It's starts to get chaffed and...
Me: Oh, well I didn't really shit my pants.
Boss: Oh. Well I did...
Disturbing Things My Boss Has Said: Part 33
Boss: I'm going to stick this [Diet Mountain Dew bottle] up your butt.
Me: I don't think it would fit. I once had to stick one of those pills up my butt to make you stop vomitting...what are those called?
Boss: I have no idea.
Me: Oh, you know. You put them in your butthole and they melt.
Boss: ...
Me: Anyway, I couldn't hardly get that in there and that was the size of a piece of chalk.
Boss: Wait. You mean you don't jerk off while you shove your old ladies dildo up your ass?
Me: ...no.
Boss: Oh man. You're missing out.
Me: ...
Boss: Just don't sniff it afterwards.
Disturbing Things My Boss Has Said: Part 32
(Going past my bosses desk, minding my own business.)
Boss: Rich, today might be the day you give me a blowjob.
(Continue walking, pretending to have not heard what he said/gotten the "uh-oh" feeling)