This is a caption I made for contest winner Elena Starz, operator of the amazing Elena Starz TG Stories/Captions. Elena's contests are what I based my contest on so it's only fitting that she get a prize. And coincidentally she started a new caption contest today so go check it out if you had fun with mine.
For her prize she gave the direction of a bimbo-type blonde, MILF sissy having trouble explaining to his son why he's giving-in to being a sissy. I decided to use a photo of Summer Brielle because she's my favorite blonde bimbo right now. This is how it turned out: