219: The Oclophobia Boat
August 2, 2018 at 2:15PM •
56 minutes •
This awkward week we're talking about the oclophobia boat, penis envy goals, and toilet vagina with special guest Stewart Wade!
Show Notes & Links
Presented by CacheFly
Awkward Story Time:
Stewart encounters an awkward actor when casting his web series.
Special guests: Stewart Wade
Timothy: "Hey there awkward humans,
My name’s Timothy and I’m afraid of cruise ships and my fiancee won a cruise vacation on a public access game show. She (Gretta) knows about my phobias and decided straightaway that I don’t have to join her. Phew! Or so I thought. Gretta is now saying that she will bring along her second best friend Michael. Michael flirts with her all of the time. Michael is mostly gay therefore I have not gotten jealous but he will play for the other team when drunk. Gretta has short hair like Ellen just not like a lesbian. If I were drunk I might think she looks like an adult boy from behind.
All in all I need your help so I can overcome my fear of cruise ships and not risk a drunk mishap between my fiancee and her mostly-gay runner-up best friend. For the details: I am afraid of cruise ships because of sea sickness and crowd entrapment, not sinking like the titanic. I would have the same fear in a floating mall or a refugee boat prior to the holocaust. I would not have survived the holocaust. Even though my nickname is Tiny Tim (not because of my penis) I am Jewish. Please don’t be offended. That’s just a holocaust joke I like to make about my troubles. Can you help me? I am seeing a psychiatrist but it will take a year she says. I need results in a month. All creative ideas are welcome.
a shortie for ya: do girls get penis envy? my girl is always on about havin a dick, wants to know what its like etc. is there pegging in my future or what? just gotta know if i got a problem."
Jasmine: "I love my boyfriend. All is well except he says “careful, careful,” when he’s putting his penis in me like it’s a grand piano getting lowered into 21st floor penthouse. I want to laugh but it kills the mood. He knows and we talk about it but it’s a compulsion for him. His first time he put in too fast and ejaculated into her. The girl told everyone in their class so he got made fun of a lot until he could go away for college. I made a list of new words to say but he tried and it looked like he was having a stroke and then said “careful, careful” and I just waited for his penis to slowly make its way inside of me. You become very body conscious in a moment like that, okay? I have thought of everything while it happens. The worst is when I think of a poop sliding out of a butthole. That’s what it’s like but in reverse. I imagine his penis is a poop sliding into my vagina. It’s slow and then plop. My vagina is not a toilet but he fucks it like one. I know better but come on. He’s seeing a therapist but what about me for the meantime?"