A Natural Sissy Part 5

I bought a few things that ladies wear, mostly lingerie, but a couple of really smart looking dresses, and a wig. Since I was a wealthy kid, I lived in my own apartment off campus. Every night, after classes were over, I'd go home and change into lingerie and put on a dress and the wig, and pretend I was a beautiful, rich lady. That even carried over when I graduated and started working as an electrical engineer. I dressed whenever I could in my ladies wear.

I moved up rapidly in my profession because I'm smart. Eventually I became the CEO of a large software developer. I won't tell you which one, because you'd recognize it right off, I'm sure. And I don't want to stain their stellar reputation by having it known publicly that the CEO was a cross-dressing sissy. Let's just say I was rich in my own right when my parents died in a tragic automobile accident some years back. The news about the accident hit newspapers around the world, but they were soon squelched by money. My sisters told me later that my mom was doing weird, perverse, things to my dad in the back of the limo, and it distracted the driver, who ran head on into an 18 wheeler coming the other way, killing all except the truck driver.

In settling the estate my sisters got the larger share, as is only right because they are ladies and I'm just a sissy. So they got joint ownership of mom's business, and each of them got 2/5ths of the rest of the estate. I haven't had much contact with either of my sisters in a while, but as far as I know, they are still running the business my mom started, and doing quite well. That left me with 1/5th of the estate, which, when added to my own hard earned wealth, made me very, very rich indeed. No, I won't share any of it with you. It's mine. Well except for what I put in trust for Gail. Two-thirds of it. And no, Gail didn't ask for it. I did it because I love her. And if I die before she does, she will get everything else that I have.

I was still cross-dressing when I first met Gail on an Internet forum, and as our relationship online progressed I let down my guard and told her a lot about myself, but didn't mention the dressing thing.