Hooking Up with My Brother’s Boss… and That’s Not Even the Juiciest Part

Things get messy in today’s Dirty Little Secret when one listener admits she’s hooking up with her brother’s boss — and that’s just the beginning. From secret office hookups to a wild gift that turns into a potential threesome invite, these confessions go from awkward to unbelievable fast. You’ll have to hear it to believe it. Listen now to The Jubal Show’s Dirty Little Secret!

---

The juiciest, most outrageous confession podcast from The Jubal Show! It's the Jubal Show's Dirty Little Secret! Listeners spill their wildest, weirdest, and most scandalous secrets anonymously—no judgment, just pure entertainment. From shocking revelations to hilarious mishaps, you never know what you'll hear next! Hosted by Jubal Fresh and the team, every episode is packed with jaw-dropping confessions, witty reactions, and unexpected twists. Got a secret? Share it with us… we promise we won’t tell!


➡︎ Get on The Jubal Show with your story - https://thejubalshow.com

---

This is just a tiny piece of The Jubal Show. You can find every podcast we have, including the full show every weekday right here…

➡︎ https://thejubalshow.com/podcasts

---

The Jubal Show is everywhere, and also these places:

• Website ➡︎ https://thejubalshow.com 
• Instagram ➡︎ https://instagram.com/thejubalshow 
• X/Twitter ➡︎ https://twitter.com/thejubalshow 
• Tiktok ➡︎ https://www.tiktok.com/@the.jubal.show
• Facebook ➡︎ https://facebook.com/thejubalshow 
• YouTube ➡︎ https://www.youtube.com/@JubalFresh

Support the show: https://the-jubal-show.beehiiv.com/subscribe

See omnystudio.com/listener for privacy information.

Episode Transcript

Speaker 1 (00:01):
Jubal's Dirty Little secret.

Speaker 2 (00:03):
Hello, Hello, Hey, you have a dirty little secret. I
do sweet?

Speaker 1 (00:08):
What is it? Oh?

Speaker 3 (00:10):
No, I'm hooking up with my brother's boss.

Speaker 2 (00:13):
Brother's boss.

Speaker 3 (00:14):
Wow.

Speaker 2 (00:14):
Oh cool. Okay he doesn't know.

Speaker 1 (00:18):
Now.

Speaker 3 (00:18):
He did catch me and downstairs in their office, but
I just said I was coming to visit him, so
he couldn't think anything of it.

Speaker 2 (00:27):
Your brother, is he nothing? That's weird? My brother would
be like why Yeah, Like if my sister showed up
to my job to visit me, that would be odd.

Speaker 1 (00:35):
No.

Speaker 3 (00:36):
I mean we're pretty close to net family. We have
dinner every Sunday together.

Speaker 1 (00:40):
Like that's the kind of thing we do.

Speaker 3 (00:42):
But the thing is that my brother was just kind
of an ad to me when I was a kid.
And so my guy that his boss is like making
him do work and he complains about it every Sunday
at dinner, and I just think it's hilarious and it's
because of me. I just I'm horrible. I just I

(01:03):
couldn't help myself.

Speaker 2 (01:04):
You wait, your boss is making him do that work
because of you?

Speaker 3 (01:10):
Yes, like doing this stupid thing.

Speaker 2 (01:13):
Oh you guys, and brother doing the things that you need.

Speaker 3 (01:16):
You even had him do his dry cleaning once like
one is dry cleaning to the dry cleaners, but it
was actually mine. Fantastic.

Speaker 2 (01:24):
Oh wow wow, I guess that's a win win for you.
Right well, thank you for telling you her little secret.

Speaker 3 (01:32):
Thank you.

Speaker 2 (01:34):
Hey, what's up? This is the ju will shows dirty
little secret? You have one?

Speaker 1 (01:37):
Yeah, so I gotta warn you because my dirty little
secret has layers. But let me start by telling you
that I've been getting anonymous gifts at work. Cool, and
I think I know who it's from. Who So my
boss he has a boyfriend, so he's gay. And my
boss's boyfriend comes around office sometimes and he always has

(01:59):
these off handed comments about, you know, how I fit
into my parents, or how my hair looks nice today,
you know, things.

Speaker 2 (02:04):
Like that nice we're sexual harassment.

Speaker 3 (02:07):
I don't know.

Speaker 1 (02:09):
Pretty much. But anyway, the last time we were together,
we were looking at something online and it was like
a CHACUZI said something like, oh, that'd be perfect for
the three of us, meaning him, my boss, and me. Right, So,
getting this anonymous gift at work. It's got a little
note attached to it saying, hey, let me know if
you don't want to try the other side. And then
it says something like like with the number three on it,

(02:31):
and I'm like, oh, that's totally who it is, you know,
and I have a girlfriend. I'm straight. Just to make
that clear. Now, my girlfriend, I've been bringing her to
like work events, so she's met everybody. And to make
this whole situation that much weirder, I brought it up
to my girlfriend. I told her that this is what's happening,
and she's kind of into it.

Speaker 2 (02:52):
Like for you to watch or like do that too.

Speaker 1 (02:57):
No, like she wants to be involved. But the thing
is that I wouldn't want, like my boss would be involved.
So I mean, we're thinking about it. Maybe maybe not,
who knows if it'll happen. I don't know, but I
think it's.

Speaker 2 (03:07):
The right career move. Good luck with that, and thank
you for telling us your dirty little secret.

Speaker 1 (03:16):
All right, thanks for having bye.

Speaker 2 (03:18):
What's your dirty little secret