My mom did so many unintentional things to encourage me to become a Sissy, then punished me when I got caught.
She strewed her bras, suspenders, stockings and heels across her bedroom, that it was irresistible to try them on. Then I found her makeup drawer and was caught in red lipstick and a black bra (didn't fit).
I was punished and banned from her bedroom, but I got back in and found a "breast exhauster" in a drawer. It was glass with a rubber bulb and a bulge to collect the milk.
Been pumping as a Sissy ever since.