Oh, I’ve got a few girlfriends, and they fuss and worry over me sometimes, and sometimes they arrange dates for me and we go out together, and sometimes I arrange my own dates. But dates are always a problem. I don’t know which gender to ask out. I look like a girl and I dress like a girl, and I live like one.
A novelette by Vickie Tern!
Jack & Jill – Chapter 1
![Jack & Jill - Chapter 1](https://www.sissify.com/wp-content/uploads/2014/11/beach-babes-featured.jpg)
I work like as a woman, as a kind of secretary-typist-administrative-girl-Friday who doesn't mind solving her boss's computer programming problems ...
Jack & Jill – Chapter 2
![Jack & Jill - Chapter 2](https://www.sissify.com/wp-content/uploads/2011/04/warning.jpg)
I went back behind my desk and sat down, and she settled into her usual chair when taking dictation, and ...
Jack & Jill – Chapter 3
![tg bianca](https://www.sissify.com/wp-content/uploads/2015/04/tgbianca-featured.jpg)
Jill never did say anything about her discovery of my little tryst with Darlene, and I never saw those pictures ...
Jack & Jill – Chapter 4
![Jack & Jill - Chapter 4](https://www.sissify.com/wp-content/uploads/2014/11/ava-featured.jpg)
There I was, finally on the street dressed like a woman, in full makeup, no place to hide from anyone ...
Jack & Jill – Chapter 5
![legs & stilettos](https://www.sissify.com/wp-content/uploads/2015/04/legs-stilettos-featured.jpg)
"I want you to think about me and Tom here tonight, in our beautiful bed. Are you thinking about it, ...
Jack & Jill – Chapter 6
![Jack & Jill - Chapter 6](https://www.sissify.com/wp-content/uploads/2015/01/prom-queen-featured.jpg)
Carl looked at his notepad, then turned over a few pages and smiled at me again. "No, Jane, my arrangement ...
Jack & Jill – Chapter 7
![True Stories](https://www.sissify.com/wp-content/uploads/2014/11/travel-featured1.jpg)
The night just past, my sense of entrapment, my acceptance of the inevitable, my conversion to desire for a man, ...
Jack & Jill – Chapter 8
![Jack & Jill - Chapter 8](https://www.sissify.com/wp-content/uploads/2015/02/spank-featured-2.jpg)
And Jill had decided for herself what kind of a woman I was, and what was best for me. She ...
Jack & Jill – Chapter 9
![legs & stilettos](https://www.sissify.com/wp-content/uploads/2015/04/legs-stilettos-featured.jpg)
I must say about Jill, it didn't take her long to put me through her crash program in "womanhood." What ...
Jack & Jill – Chapter Ten
![Fashion Show](https://www.sissify.com/wp-content/uploads/2015/06/fashion-show-featured.jpg)
Five minutes later I had poured Art a full tumbler of whiskey and he had emptied it down, by the ...