Change of Heart

change of heartMoved by the spirit (no pun intended) of the season, on the very night before Halloween I decided to throw together a caption that had something to do with dressing up as a woman. I had already posted a Halloween caption this year, so it wasn’t like I had to, I just felt like it. (I don’t dress at Halloween, so maybe I’m compensating.) Anyway, I found this pic in my to-do folder (which has well over 200 items) and the story in it fell into place very quickly (compared to my usual pace). For the record, I have no idea why the girl with the ponytail wants to humiliate her target or why she chose poor Kenny as the means of doing so. TG fiction is littered with women who do this sort of thing for either no obvious reason, or at least no good reason, so for now we’ll just have to go with the stereotype. Enjoy!

I’ve written quite a few captions where the hapless hero is coerced into cross-dressing. (Don’t ask me why; I’m still trying to figure that out.) The last caption to involve both that and hypnosis was “White Collar Crime” from earlier this year. There are many others in the archives.


P.S. We got us here another quite wide caption, so here’s the JPG file for the viewing convenience of all those who don’t dig the whole PDF experience (you know who you are). Click on the above icon for the PDF version.

5 thoughts on “Change of Heart

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  3. I bet Kenny or Kenna will have been taken to a new level. Turns out the reason Damien is the boss is he got eyes everywhere; the salesperson that sold this woman the fake breasts was on Damien’s payroll. And the woman was a jilted lover of Damien’s, seeing she thought Damien only liked girls; turns out Damien likes both Girls and T-girls but no one in Damien’s organization knew about the T-girls so this is why the revenge. Kenna’s programing ended and she woke up in Damien’s bed totally nude. When his secret was known he thought he was going to be dead, but Damien was spooning him and asked, what is your name sweet cheeks. Kenny was so scared he answered him in a mousey voice: it’s Kenny. When Damien corrected her NO it is Kenna, my new woman. Kenny, realizing his life was over, answered yes my name is Kenna your new woman. Damien said to make this real you will have to see my private doctor; she will make you beautiful.

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