Wednesday, April 13, 2016

I Won! I Can't Believe That Dee Lost the Bet!

I'm nothing if not a gracious loser though, so enjoy your "prize" because you've earned it!

Luck Be a Lady Tonight, INDEED!

Made this for Brittany7, who has been a steady contributor to our DIY Challenges almost since when they first started. You can always expect her to come at it from a slightly different angle than what you would expect, and that is part of the fun of running the Challenges.

I saw the picture and knew I should work in the booth and the guy that was in it, well at least his jeans were in it. I guess the irony is that I ended up cutting them out as the photo was big enough as it is and I edited out everything I could. I thought about her not wearing panties, and it almost seemed like the protagonist was actually rubbing the lack of panties in the photographers face .. and that gave me the idea of someone that "won" a bet with Dee, especially once everyone was a bit soused with some demon alcohol.

Even with all of Dee's magic, she still "lost" and that is definitely something to be proud of I would think, since that doesn't happen too often. Even though you might have to redefine what winning meant in this case, Brittany seems to be having a good time anyway, and I think the booth guy will enjoy it too. Something tells me that I had bet him earlier that he'd be having sex with a former man by the end of the night. No idea what pay off THAT will bring me. Sometimes when you bet, it is more of a crap shoot than anything else!

DISCUSSION QUESTION: Do you like it better when the subject LOSES a bet, or technically "wins" but ends up feminized due to the way they won? How about if the subject plays to lose? Is it better if they win or lose at the end?


  1. I enjoy bet captions either way. but having them lose more than they won is a great twist to the caption. my tastes are for forced fem so i am not so keen on the guys playing to lose.

  2. Seeing a guy lose a bet is the typical road, so seeing something different happen is always a breath of fresh air. I like captions that take the road less traveled.