aka “My Boss, The Bimbo“
by James J. Craft

Color Illustrations by blackshirtboy

A "Tales of Transformation" Story

Lucas is the young, wunderkind CEO of his company, groomed to be the next Chairman of the Board. Unfortunately, he’s not much for making friends or being particularly genial. His secretary, Irene, has had to put up with his macho, competitive personality for too long.

When Lucas makes some outrageously misinformed claims toward women, he’s put to the test. He makes a bet that he can wear a pair of heels for a week, just like the women of his office. 

After losing his bet, he makes another, pushing it farther. He loses. Then another bet. He loses. Soon, he finds himself going to the extreme to prove his point, that he can do anything a woman can.

Written by James J. Craft, author of “Big in Japan” and illustrated by TG favorite blackshirtboy.

Instant Download for

If I Were a Betting (Wo)Man


Rated "PG" for sexual
suggestion & language.


• Slow Change

• Character Change

• Crossdressing

• Gender Change

• Offices & Secretaries

Book. 38 pages.

• 10 illustrations in color

• Instantly downloadable PDF for $7.95

• PDF edition with no copy protection

• Fulfillment by lulu.com

Preview the first 14 pages. PDF Download.

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