tagTranssexuals & CrossdressersA Natural Sissy Ch. 05

A Natural Sissy Ch. 05


Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justify it.

Ch. 05 Stacy's Interlude

"Hi, guys. I'm Stacy, and I guess you know I'm a sissy from what Gail has been writing about me. I don't mind being called a sissy, because that's exactly what I am, and we should all be proud of what we are, shouldn't we? Gail told me that I needed to write this chapter, and tell you some of the things she has learned about me from our private talks. I resisted at first, but when she threatened to tie me to the toilet with my face up so all her friends could come visit and piss in my mouth, I decided that compromise was my best option. I've tasted piss before, and everyone knows it's sterile, but I just don't like the taste. So just sit back and listen while I tell you a little about me and how I grew up as a rich kid. Yeah, my parents were very rich. My dad, who I didn't know was my dad until I was a teenager... well that's getting ahead of the story. Let me just say 'he' never worked a day in his life – at least not for pay. He inherited a really big estate when his parents died, just like I did later. My mom was rich, too. When I was small, she would go off everyday and not come home until sometimes very late at night, and sometimes it was late morning when she got home.

She never told me what she did while she was gone, and I only found out when my two older sisters sat me down when I was thirteen and told me. I remember that day like it was just yesterday. Here I was, dressed just like my sisters, in a girl's school uniform. They wore them to school everyday, but I was wearing one because I was being punished for mouthing off to my oldest sister. Did I say that my sisters had absolute authority from my mom to discipline me when they wanted to? I didn't? Well, it's true.

So here I was, dressed like a schoolgirl, except I didn't look like a schoolgirl because my hair was short, like any other boy. The younger of my older sisters was doing things to me that I can't mention, until I yelled, and then they would both laugh their heads off. I didn't dare talk back to them, because one time I did that and they took me down to the dungeon, and strapped me to something they called a St. Andrew's cross, and they beat me with all kinds of things they took down from the dungeon wall. I never want to go through that again.

Anyway, my sister let something slip about what mom was doing that day, and when I asked what she was talking about, they whispered to each other for a minute. Then one of them said, "Okay Stacy, I guess you're old enough to know. Mom is a professional dominatrix. Do you know what that is?"

I did, because I had been reading erotica stories from Literotica and other websites since I was ten. But I feigned innocence. "No. What's that?"

So I got the whole nine yards about my mom. She made her money training men to be subservient to women. Her clients even included royalty from all over the world, and all her clients were near the top of the wealth chain. She was too, because her fees were out of sight. And none of it was reported to the IRS. Only my dad's inherited money was reported. But I still didn't know who my dad was. It wasn't until I was about to go away to college that I found out our live-in maid was my dad. He was absolutely gorgeous, and I wanked off thinking about him when I went to bed at night. He was the most beautiful woman I had ever seen. I mean he put movie stars to shame he was so beautiful. But he was always rather quiet around the house. And he always deferred to my mom and my sisters in everything. I guess mom had trained him well.

Being the baby in the family, I was always the first to bed every night, and as I look back I realize that some of the strange noises I heard after I went to bed were my dad being disciplined by my mom and sisters for some fault they found with him. Some of the noises were not discipline at all. Well maybe they were, but they didn't sound like it. I've heard the same noises as an adult, and they were definitely sexual in nature. My mom and my sisters were using my dad the same way I get used by Gail now.

Anyway, after I went off to college, I though about my dad, and the life he lived, and how beautiful he was. Or she. Having been dressed as a schoolgirl by my sisters kinda crept up on me, and combined with my images of my dad, I developed a desire to dress like a woman. I didn't want to be a woman, but I certainly wanted to look like one. Does that make any sense to any of you?

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. But she's a smart lady, and in reading between the lines I guess she recognized a sissy. Turned out that she has trained a few herself, so she has a kind of kinship with my mom. And that's not a bad thing at all. I loved my mom, and I love Gail.

And that's what brought me to be where I am now. And yes, I'm very, very happy with my station in life. I do have ambitions to be a beautiful lady like my dad was, and it will happen. I know it will, because Gail loves me, and she will let me do it someday, when she's ready. Yes, of course it's her decision to make. Who the hell else would make such a decision for me?

Oh, excuse me for a moment. Someone's at the door. Okay, I'm back. Sorry it took so long. It was the new neighbors from next door. Adriana and Joel, or Joy, maybe is his name. I heard Adriana call him both while she was talking to Gail. They're all in the bedroom right now, and it's getting a little noisy up there. Can you hang on a sec? I need to go ask them to hold it down a little so I can think what I need to tell you next. Be right back. Just help yourselves to some refreshment while I'm gone.

I'm back. Sorry about the delay. I had to watch for a few minutes. The new neighbors are sure a friendly pair. Let me just take a moment to tell you what I saw up there. I guess this Joel guy, or Joy... whatever, is a sissy like me. I thought he looked kinda meek when they came in, and he didn't say a lot, but when he did, he curtsied, even thought he wasn't dressed like a girl... then, anyway. But now he is. He's wearing his own lingerie, but he has on a pair of my high heels, and my best wig. I guess the makeup he's wearing is mine too. Anyway, Gail is naked as a jaybird, lying on the bed, and Joy's head is right there between Gail's legs, and he's slurping at her pussy like mad. Gail had her hands on his head, guiding him in deeper, I guess with his tongue extended. That's the way I do it, anyway, and Gail likes it just fine. But get this. Adriana is buck naked, too, and she's wearing Gail's really big strap on. The biggest one we have, and she's fucking Joy like there's no tomorrow. It's a really hot scene, if you know what I mean. She's pounding his ass so hard she's driving him deeper and deeper onto Gail's sweet pussy.

Well, enough of that. Where was I, when I was interrupted? Oh, yeah, I was telling you about my ambition to look like a beautiful woman like my dad was. So...

Well dammit, I just got called upstairs, so I guess I'm done with my story for now. Maybe Gail will let me write another chapter later. Bye now.

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