Sissy Tamer's Contest Prize and "Bonus"

I'm continuing to post my "prize" captions for the contest winners and today are the captions I made for Sissy Tamer. Now, even though two of his captions were winners, I was only supposed to do one caption for him. But, I liked his caption about the Tyra Banks Show episode so much that I wanted to do a sequel of it for him in addition to his custom caption.

So first, part two of his winning caption:

And for his actual prize, Sissy Tamer wanted a caption with a teenaged-looking transsexual as Bobbi. he wanted it to be about his father being humiliated because he's in chastity and accepting a future punishment to get unlocked because of how turned on he is by Bobbi. With direction like that the caption wrote itself:

Once again, congratulations to Sissy Tamer. I hope you guys like these as much as he did.

PS: I'll get back to posting my non-custom stuff tomorrow. Jenny, my other contest winner has asked that her prize remain private.