Sissy's School Reunion

This is the first chapter of a completed, 8 chapter, 100 page book with images.

Chapter 1

It would take so long to explain how I got here. I don't even know if I could untangle it, to be honest. I certainly didn't intend to end up like this. My dreams involved me wearing a trim suit and coming home to a loving wife. I thought I'd be a real guy's guy and conquer the world. I wasn't sure exactly how I'd do it, especially since I was mediocre at everything from grades to athletics. But this was not the plan. I cannot emphasize that enough. I know it's hard to believe me. Anyone who saw me now would assume that I was born for skirts. They would assume I chose this. Maybe I accepted it, but I certainly did not choose it. It was all circumstance and misfortune and my life turning out in ways I couldn't imagine.

I mean, who could imagine becoming a sissy!

I didn't even know what it was until I ended up as one. By then, it was too late to turn back. "Sissy" was simply the word to describe the culmination of all that had already been done to me. I was already dressing en femme, already on hormones, already at the beckon call of a rich man. He supported me. He saved me. But it all came at a cost. I couldn't say if I was manipulated, though it's hard to say otherwise. I couldn't make any sense of it, and even trying gave me headaches. All I could say was that there was no going back, and that he took care of me.

In a way, it wasn't even that bad. I tried to forget about my old life to make it easier, because it was great in a vacuum. Without the knowledge of who I had wanted to be, without the knowledge of what had been taken...

Anyway, it was a pretty okay life.

My main responsibility was looking pretty, and even that was more or less handled for me. He told me what he liked and I catered my appearance to those preferences. He made three appointments a week and I kept them, spending the day at the spa and salon until I was utterly perfect for my Daddy. Those were my main excursions, but even those short trips were enough to remind myself of my new state. Daddy was truly a wealthy man, and had spared no expense making me ideal. There were Hollywood actresses who had less resources at their disposal when it came to getting work done. I could take that for granted when I was alone, but even the walk from the car to the salon door was enough to remind me. Guys whistled. They patted their friends on the shoulder so they could all stare at me together. A few bold ones tried to catcall, and one caused a fender bender by looking too hard at me instead of the road. It didn't help that Daddy's wardrobe for me was rather provocative, and meant to show off that which would be jaw dropping even in modest clothing.

Those moments were the ones that really made me squirm. I occasionally minced faster through the doors, making it clear that all the attention was getting to me. Even inside, the women judged. They stared at my brazenness, and seemed to share looks of judgement. I was just some hussy to them. I was a bombshell bimbo that was probably the trophy wife of a rich guy...

And they were right. That was the worst part.

All I did now was read gossip mags, watch reality TV and stay up on fashion. It couldn't be done entirely at the salon, so it was up to me to know how to upkeep my beauty. I probably could have done everything my beauticians were capable of and more, but I get the feeling that Daddy wanted me to go out and see them. Maybe he knew how it made me blush.

I wasn't entirely eye candy though. He must have sensed how listless the sissy life made me, and allowed at least some alteration to my normal routine. That's why he paid for culinary courses for me. I actually got really good at it, and was left with the idea that I might have been a good chef. If only I had known that before everything. I could have been a world renown cook, doing a reality show where I tried food around the world and then going back home to my wife. That could have been the way I ended up a successful and accomplished man...

But, again, it's best not to think about that.

Most days start with me waking up and taking stock of how sore my anus is, before heading to the kitchen to make Daddy breakfast. He's the CEO of a major corporation, so he needs to get plenty of calories to be ready for the day. I mainly subsist on salads, shakes and vitamins, and don't really get to eat my own food. But at least I can smell it while I cook him up his breakfast.

I then mince back to the bedroom with his meal, ready to help him start the day. I should explain that I sort of have to mince now. I've been in heels so long that my tendons have shortened, and I stand on my tip toes even in bare feet. The good news is that Daddy has bought me more shoes than any girl could ever ask for, and I get to wear them about. Besides, a part of me thinks I'd look silly in flats now. They're just another thing I've left behind, along with pantlegs and high cut tops.

It wasn't that bad though! I got everything provided for me, and was totally looked after. Besides, I could do a lot worse than Daddy. So many of these sissy stories dealt with ugly old men, and my Daddy was actually a year younger than me. He was tall and fit and had a square, handsome face. He was a better looking Daddy than any of those in the stories that he made me read. Even sleeping there, I thought of how lucky I was by comparison.

I leaned forward and cleared my throat. Three years as a sissy had taught me that women had natural poses they tried to avoid when it came to showing themselves off. They were conscious of their bodies and outfits and knew how to avoid being objectified. I'd learned that because my Daddy wanted me to do the exact opposite. He had paid a lot for these boobs, and he expected me to present them.

"Breakfast is served, Daddy."

He opened an eye and looked at me. Jet black hair. Piercing blue eyes. You really could do a lot worse...

He took the tray and I gave a curtsy which made him smile.

"How is my little Missy today?"

"I'm good. How is Daddy?"

"Daddy is fine. You really gave me a workout last night... surprised to see you aren't limping."

"Oh, Daddy. You're so naughty..."

"I feel like a glutton. I'm eating but you're not. Here..."

He pulled off the covers to reveal her underwear, and the pipe-sized bulge within. That was part of the reason my Daddy had wanted a sissy. Women with cervixes to hit didn't like his size. Even some people who liked anal found him to be a bit much, but I was lucky to be well trained for it. And he was lucky that I wasn't allowed to have much of an opinion.

"Oh... Daddy..." I purred as I crawled into bed. I made sure he could look right down my dress and I wrapped my hands around his waistband. I made sure to be slow as I dragged it down. He liked it slow. But soon enough I had pulled it down enough to make his member spring straight up.

"Kiss it hello..."

He didn't need to tell me. I knew exactly what he liked. But I let him tell me all the same, because I knew it made him feel even more in charge than he already did. I leaned in and placed a tender peck on his tip as my hand wrapped around the base.

He ate without giving me much thought. I hadn't done anything to deserve it yet. But as I began to lick him up and down with tantalizingly slow streaks of saliva, I knew that would change. I must have put in 10,000 hours when it came to this, and so I was able to make him groan when I wanted to. I teased the bottom of his balls with the ends of my long nails and then started to take it down my throat. My gag reflex was long gone, but I still put on a good show. I paused. I made the noises. I let it seem like he was too big for me, even though you could have shoved a baseball bat down my throat.

Then, I kissed the base.

He was still eating, but it was clear he was enjoying it. He actually had to stop himself so that he could feel and savor it all. So I made sure to give him something worth savoring.

Each bob up must have been an absurd sensation. My throat. My mouth. My tongue. All of it clenched tight and dragging against the sensitive flesh of his massive shaft. Not a bit of it neglected. All of it wet and warm.

Each bob down was a feat of my abilities as I drooled and unleashed globs of saliva. As I went down, so did streaks of wetness which soaked his rod in successive coats of moisture.

His hand was on the back of my head now, and he guided me to increase the pace. He was a true stud, and could have lasted against even my best attempts for an hour. But he had work, so I knew it wouldn't be that long. I quickened my pace until it looked like I was trying to headbutt his hups, going up and down so fast that it was almost violent. It was so wet, so loud... so degrading.

But then I felt a powerful heartbeat in my throat. It pumped harder and harder inside of me, and I knew it wouldn't be long. The pulses came hard and faster until-

Until he shot ropes of his seed into my gullet.

I knew what to do after. I went up and down two more times, using my lips and tongue to get him completely clean. With a pat on my head he let me go, and I sat up with a smile.

"Was that good, Daddy?"

"Very good, Missy. Well, I have to be getting to work. But first... present."

I nodded, so used to my routine that I would have been unnerved if we skipped this step. Getting out of bed, I reached down and lifted off my dress to reveal the glint of a silver metal circle. It was completely bare down there, waxed and Naired constantly to make my balls look like pale globs of porcelain beneath their metal cage.

"You know what's coming up in a few weeks?"

"Umm.. no?"

"A thousand days caged."

"Oh..." I said, somewhat struck by the news. I knew I could be caged forever, but actually having a number attached to it made it all seem more real. "That's exciting."

"I thought you'd say so. Of course, we had you in a bigger cage then. You almost had something you could call a dick."

"I... I don't know, Daddy. I think I've always had a clitty."

"Well, of course you would say that. Now you're flat. Flatter than a girl, to be honest. At least they have a little bean. You're all locked up."

"Of course, Daddy. A sissy needs to be locked up!"

He leaned over and wrapped his hands around my balls, which made me shift. I still had sensation, and it had been honed into a fine point by so much neglect. Just a breeze on it was enough to make me shudder.

"Don't worry though. You can spurt without touching your clitty. It's clear though. Dead. No continuing your line. No seed for you! But imagine you as a parent. No... you're always be a little girl. You'll always need a Daddy to take care of you."

"That's so true. And I love my Daddy!"

He patted the front of my cage and got up, stretching out for the day. "Have fun today. No appointments. You can read your cookbooks. And tonight... we'll see about making you squirt."

The day passed by relatively normally from there. I didn't particularly like reality tv, but it was actually somewhat entertaining when you turned your brain off. And I did get to cook more when I had nothing to do, provided I didn't ruin my nails. The only caveat to my relative freedom was that I needed to be ready and presentable at 5:30 when Daddy got home. I was supposed to kneel in the foyer and greet him with a great big smile. So I went about occupying my time until that moment arrived, mostly wasting it however I could. I did have some exercises to do, like squats and other things designed to keep me trim and pretty. I also had to send him a selfie for his lunch, one that looked right down my top. But once I got that high angle pic out of the way, it was all pretty simple. I was actually so bored that I decided to take an early shower to get ready early. It was therapeutic to be under the hot water, even if it enveloped my body in a way that made it impossible to ignore. My breasts. My cage. My butt. Everything about me was as feminine as possible. It was his. Not mine.

And as I washed myself, I heard him laughing outside.

I nearly jumped out of my skin. He wasn't supposed to be home yet! He was still supposed to be at work, and that meant... he couldn't punish me, could he? I had to be kneeling in the foyer at 5:30. It wasn't my fault he was here early!

I quickly got out and wrapped myself up, going out to see him laughing in the hall. He didn't seem to be in a punishing mood. In fact, he seemed downright gleeful. He was holding a piece of paper, and looked up to me as if he had excellent news.

That couldn't be good.

"Daddy... what is it?"

"Oh, I just had to come home. They have everything handled at work and well... I got an email."

"You... what?"

"Not my email. Your old email. When I took away all your communications, I kept it. But you got an email..."

"What is it?" I asked, not entirely sure what to expect. My parents were both dead. Daddy had handled all my affairs and financial obligations.

He handed me the paper and chuckled to himself as I read. The more he laughed, the more expression left my face. The more his flushed with enjoyment, the more mine went pale.

"Miles Washington. We are holding our ten year reunion and would love for you to attend! Please RSVP at your earliest convenience."

I looked up to Daddy with sheer horror in my eyes. "Da-"

"We're going, Missy. I, for one, am eager to meet your old friends."