Horror Story

Original:  This was labeled simply "Skirts and Dresses". My guess is that it's the graphic for a newspaper or mail order catalog ad, anywhere from the mid thirties to the early fifties.

It's not the forced feminization or the age regression that makes this a horror story, it's forcing him to go to a Justin Bieber concert.  

The body language, the poses, and the clothing of the three all suggest that the girl on the left is younger than the other two and that she is not having a good time. The pose shows that she is flat chested, she's looking down and not smiling as the other two are, and the hat also make her look younger.