31F / 32F - Ask us anything (and make us feel embarrassed)

PurveyorOfFineDares · 02-29-2024, 03:47 PM

Oh I love an excuse to break out my embarrassing questions. Here's a first batch, probably more to come later...

For Jess:

How much money would someone have to offer you to post a video of you and Steph having sex to a porn site? For this question, assume she would agree no matter what amount you pick.
What is one thing you know about Steph that she doesn’t think you know?
What is one sexual fantasy or kink that you have never told Steph about (if there aren’t any, which one were you most nervous to first tell her about?)

For Steph:

Have you ever taken a nude picture of yourself and if so who has seen it?
Imagine Jess has lost a bet and must do anything you want for one day. For this fantasy assume she will consent to anything you choose to do, even if it’s normally a limit. What does her day look like?

02-29-2024, 03:47 PM	#11
PurveyorOfFineDares getDare Sweetheart Join Date: Jul 2023 Posts: 262	Oh I love an excuse to break out my embarrassing questions. Here's a first batch, probably more to come later... For Jess: How much money would someone have to offer you to post a video of you and Steph having sex to a porn site? For this question, assume she would agree no matter what amount you pick. What is one thing you know about Steph that she doesn’t think you know? What is one sexual fantasy or kink that you have never told Steph about (if there aren’t any, which one were you most nervous to first tell her about?) For Steph: Have you ever taken a nude picture of yourself and if so who has seen it? Imagine Jess has lost a bet and must do anything you want for one day. For this fantasy assume she will consent to anything you choose to do, even if it’s normally a limit. What does her day look like? __________________ 27M, straight Interested in: giving dares, designing complicated dares, receiving reports