From December of 2015:
I have been sitting on this caption setting for MONTHS! I knew it was a good setup but really couldn't get the whole gestalt together, and didn't want to half-ass it. I even thought about offering it as a DIY Challenge caption at one point but with "Themes" the last few months, I didn't use it then either, so while figuring out my posting habits for the rest of the month, figured I would pull it back into Photoshop and take another stab at it.
Which I am glad I did. This time I had a much better feel for what I wanted to do. I had always thought it was either going to be a school or a resort that would be converting her husband to a woman / sissy. Making a decision that the two representatives from the school be alumni, which many schools do anyway when they recruit top incoming members of the student body, I think is what makes it a better caption that what I've had done with it months before.
I mean, that is quite a sales pitch. Your hubby is going to look, and act like this, and we are going to rock your world in bed to prove that our graduates are ready to please you in any way you wish!
I left this caption a bit open ended, so that the reader can place themselves in the role of the husband. Do you wish to be your wife's lesbian lover? Well, fine, that is what she is going to sign you up for, but if a sissy maid is what you want to be, then there's an option for that too. Continue the story in your mind, and there are so many pages in that contract and brochure. I'm sure that their campus is large enough, with a patient enough staff of teachers, that you can be taught whatever you need to know to make yourself the bestest plaything for your former wife/current owner!
I bet you can't wait to unwrap your new student school girl uniform on Christmas morning, along with everything else needed to make your year at the academy a perfect one. I wouldn't expect you to be anything less than a valedictorian sweetie! You've got so much feminine potential, we just need to bring it out to the forefront and dissuade you of any lingering masculine pride! Be the girliest girl, or the swishiest sissy you can possibly be!
DISCUSSION QUESTION: I didn't make this a trade caption due to there being no protagonist in the actual picture. For reasons stated above, I thought it worked best in showing the wife and the alumni negotiating the contract. Do you think this was the best way to handle the caption? What other ways would you have worked with this photo and what sort of story would you have come up with?