Thursday, March 20, 2014

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.


  1. love the follow up may be room for another? great fun caption two, Poor daddy. excellent captions

  2. soo grosss why cant the dad just watch why did you have to bring him into it..

  3. This may be my favorite on the site so far! Wow...