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cuckold date challenge

Life in my female led relationship is never boring. My Goddess has given me until the 13th of this month to ask a another girl on a date (something I'm slightly terrified of) I will be in chastity like always. She has upped the stake tho. If i ask a woman and she says no, i get 2 more months locked up with no relief (it's already been 3) if i don't ask anyone, i get 3 more months. I have no idea where to start. So....... Any sexy Michigan bbc lovers interested in dating a well trained, respectful, chastity boy for a night? E could end it with some cuckolding fun of course!


Real Person
Gold Member
Interesting challenge! Your Owner wants you to ask another woman out on a date with the term of your chastity depending on it.

Two things I don't understand:
1. What would the cuckolding fun, that you allude to, consist of, as it would appear to be just your Owner, you and the woman that has agreed to going on the date. What would be the "pay off" for the lady accepting the date?

2. If you fail to ask anyone you get 3 more months, if you ask and are declined, you get 2 more. If you ask and the lady accepts, what do you get?

The reason I ask is, depending on what the pay off for the woman is, when weighed against the amount of additional time you will be subjected to in extended chastity, she may decide it more amusing to turn you down just to enjoy knowing she is causing you that much more suffering. :devil::D