Letter to the Staff of Sissify – Chapter II

After a while, not quite as shaken as when I first sat up, I looked across the room. There on a chair within easy reach was a luminous blue satin dressing gown, a brighter shade than Kate usually wore, and a large, heavy-duty bra. Then as if to make up for the utilitarian massiveness of the bra, a teeny pair of delicate rose lace hi-leg panties. And a note.

I sat back on the bed and opened the note. Kate was going all out — the paper was perfumed, that floral scent I remembered from before she went to work at the clinic, that she still wore when we went out somewhere fancy. I breathed it in and opened the note, and read:

* * *

“My Darling Annie, or if it’s Andy reading this, my poor bewildered Andy. First, I want to remind you, whichever you are, that you are *mine*, not your own person. You pledged yourself to me knowing

that I intended to do things you might not like, however deeply a desire for some them might be implanted in your psyche. I think you know now what I intend. I intend to make a woman of you. A real one, not a simpering transvestite concoction of one, which is probably all you’d have managed to make of yourself without me, and not a Drag Queen either. But also, not the kind of woman you’d be if you’d been born a girl and raised in the same circumstances you’ve enjoyed as a boy, not a restrained, educated professional woman. Not even a woman like me, more venturesome than you are, more of a take-charge kind of person. No, someone different.

“Brace yourself, darling. I want you to become my kind of woman, the kind I’d love to spend time with, and go out with, and make love with. And date men with. The kind I find exciting, as you’ve never been as a man. Impulsive. Playful, even silly at times. Instinctive and generous, warm hearted. Physical in many ways, most of them feminine — tender and demonstrative when you feel affectionate, which will be often, and sexy when you feel a yearning for that kind of pleasure, also often. Not too inhibited. In fact, a little smutty in pursuit of your pleasures. The kind of girl men are happy to find they’ve been fixed up with on a blind date, because attractive at first glance. The kind men remember the next day with smiles on their faces. And don’t be shocked dear. The kind of girl women can remember the next day with smiles. The kind I’ve always wanted to remember with smiles.

“If that isn’t you now, and I know it isn’t, that’s what will be you. You are mine. I’ve always wanted that kind of girlfriend, so that’s the kind of girl you will become. You’ll try with all your heart, soul, and might to become that girl. I know you will. You have no other future.

“When you’ve succeeded, when you like being that kind of girl, then you can be my friend as well as my servant, and we can enjoy that relationship too. You are already married to me, as you know. I may then be willing to marry you. But only then. We’ll see.

“Love,

Ms. Katherine

P.S. You see in front of you the first intimate wear of the kind you will wear for the rest of your life, your first bra and panties. Congratulations, sweetheart. Also a rather lively gown, the kind Annie will soon love to wear as the truest expression of her own lively nature. I’m sorry the bra looks something like a washer woman’s, but your breasts, your pledge of servitude to me, need that kind of support right now. I’ve tried to make up for it by giving you panties a whore might blush to wear. Put them all on, and splash some of my cologne on too, and some matching scuffs from my closet. While you wait for me to return I want you to begin browsing through some of the women’s magazines I’ve accumulated downstairs, ads and all. They’re your kind of magazines now. They’re the sole occupation of your mind from now on.”

* * *

With my nightie off I saw Kate was true to her word, the only fringe of hair anywhere on my body was neatly trimmed around my pubes — the rest was smooth. I dressed as Ms. Katherine ordered. The bra felt heavy on my shoulders until I realized the weight was in my hanging tits, eased when I remembered to stand up very straight. But then they protruded out, way too far forward. I doubted even a loose sports jackets would cover them, much less a tailored suit jacket. How would I go to work? With a weight on my shoulders, or else with a lot of explaining. The panties were indeed teeny, designed to curve below the curve of my belly and across the curves of my buns. I didn’t have a woman’s sexily rounded buns yet, but I knew I’d get them, if not by hormones then by more implants. Kate would see to it.

I inspected myself in the mirror, and I saw a man with straight long hair — that’s how I liked it — wearing a large bra and skimpy scanties. Boobs nicely proportioned for his shoulders, which were a little large. The breasts would swell up even more when the hormones got hold of them, I realized, no doubt as part of Kate’s plan for me to look like a sex pot at anyone’s first glance. Waist a bit thick — I should diet. Then I realized that was a girl’s thought, Kate’s scheme was getting to me. Hips narrow, but that’s true of some women, I knew. Big bulge in my panties so far, thank God! Could I become the kind of girl Kate wanted? Possibly, with diet and the right makeup and gear. And the right temperament. It could be fun. My face was small-featured, and I had an unassertive chin I’d always regretted. Now I could see it was a dainty chin. Or might become one. Did I want to become Kate’s kind of girl? Did I have a choice?

I wriggled my hips at the apparition in the mirror, and immediately felt silly, even indecent. So I took a full-figured blouse and a wide skirt out of Kate’s closet almost without looking at them, and I put them on. The bottom of the skirt brushed my calves delicately. The blouse was short sleeved and nylon or something, so when I put the satin dressing gown on over it I felt incredibly slippy all over, like wearing liquid. With another glance in the mirror I saw that its bright iridescent blue seemed to light up the room. That’s me, life of the party, I thought ruefully, and went down to the living room.

There I picked up a copy of “Cosmopolitan.” I noticed immediately that my breasts were already larger than on most of the women photographed in that magazine, even the “Cosmo” girl. I started reading an article on how to keep *him* interested in asking you out again. Some of the advice was excellent — ask him to tell you about himself, and admire anything you can that he’s accomplished — I wished girls would do that for me. I wished girls had done that for me. I realized that I was expected to do that, now. But a pang of panic struck my midriff! With guys? No, I wouldn’t! I was Kate’s!

Some of the advice was practical — “If he seems excited to be with you, help him sustain that level of excitement by caressing him in sensitive areas. You can find out quickly enough if he’s sized to your needs. And being kissed by a smooth, wet, deep mouth is sure to please him!”

Now I shuddered. To kiss a man? Did Kate mean that? Before this was over did she want me satisfying men with hand jobs? Worse, with blow jobs? Real ones on real men, not idle fantasies? Swallowing real cum? “Smutty” was what my Mistress wanted, and she’d see to it that’s what she made me! Even more, would I as a woman need to let men — I tried to imagine it and couldn’t, and felt a little queasy — enter me?

And pump me? And cum in me? Deep inside me? Oh my God!

That was as much as I could take. There had to be a way out of this! This was only a game, a scene we were playing, and I was taking it too seriously! Then I realized I had no safe word. Kate had started me off with the injected hormones and breast implants so the road back would be harder than the path of least resistance, so I’d go with whatever she wanted, like it or not, and learn to like it. I was already part way where she wanted me. Dressed like a courtesan and reading up on how to get laid.

I decided to read the ads instead of all the distressing no-brainers on “How to Get Real Hunky Men to Fuck You Senseless” There were hundreds of ads for make-up! Eye liner and shadow and pencil and mascara in varying shades were individually mysterious, and as I realized when I studied page after page of superbly blended eyes on gorgeous models, how those powders and brushes and pencils could create the mysterious seductiveness of those eyes was beyond any male comprehension. I’d never learn how to use them!

Still, I had to please Kate until I could persuade her somehow to give up her plan for me but marry me anyhow — my only apparent way out. Applied Lipstick looked like a course I could teach myself. I read an article on the new shades, and figured out the uses of lip liners and upper-lip shaping, went back to our bedroom, and applied a dark maroon to my mouth. That would show Kate that I was trying.

Now a glance into the mirror revealed a man in a bright blue satin gown wearing lipstick. Neatly, though. I went down again and read on, wondering why I wasn’t getting increasingly resentful. Was I really a wimp? Look what she had done to me! Did I really want it? I suspected there were more tranquilizers in me than I knew.

A few hours later Kate returned. I was back at the computer when she arrived, originally to get some more advice from Sissify.Com about make-up and how to cope with my new situation, but now looking at different e-mailed reactions to the report I’d turned in. I saw I had to go into the office to talk to some associates.

“Looking for some new games to play, Annie?” she said when she saw me staring at the screen. “Remember you’re my plaything now, and I make up all our games. Any time you forget that, just fold your arms across your chest to remind yourself.”

“No, this is business,” I said a little morosely. “I have to talk to some people downtown. Tomorrow.” I turned around and stared at her. I was now in no mood to play, but realized that for a servant I had spoken out of line. “Ms. Katherine, Ma’am?” There was a faint edge of sarcasm in my voice. “Do I have to kowtow to you all the time from now on? Can’t we just talk?”

She didn’t seem to mind my asking. “Any time there are other people present, certainly we can just talk, Andy honey. Then we’ll talk the way we’ve always talked. Of course you’ll always agree with everything I say, and I look forward to hearing the reasons you’ll give for agreeing with some of my the things I’ll say.

I’ll say some outrageous things sometimes, just to keep you in line. At first you’ll agree with me any way you can, but when you’ve become the woman I want, I’m sure you’ll agree with me sincerely.”

“When nobody’s around it’ll always be different. I’ll expect you to remember your place and my place, and to address me appropriately. This is a process, a journey, and we’re only just beginning. When you finally arrive where I mean to take you, when you’re the kind of girl I want you to be, then maybe we’ll talk as

equals sometimes. I expect that by then you’ll be so pleased with yourself you’ll want to thank me. Are you resenting me a little right now?”

I hesitated. “Yes, Ms. Katherine” was all I said.

She stared at me a moment. “I appreciate your honesty. And also your effort to please me by wearing lipstick. You did a good job there for your first time. The shade’s a bit too maroon for the color of your robe, but you’ll learn about things like that.” She smiled. “That’s the favorite shade of a girl I went with my last year in college. I loved seeing her lips that color while they tugged on my nipples and nibbled on my clit. I’ll love seeing yours there too. If you really like it, we’ll build your outfits around it, honey. It’s still fashionable.”

Kate a Lesbian when she was in college? No, probably experimental, bisexual. And now me too?

Then Kate commented further. “That’s a pretty blouse you picked out, even though I didn’t ask you to. I’m glad you like it. It’s yours now, and I think that’s what you’ll wear when you go to your office tomorrow for your meetings. Just a touch of lace on the collar ends, and it billows beautifully, so no one has to know about your new breasts. They’re a ‘C’ cup now, incidentally. Your hormones will soon make you at least one size large still, really a knockout, though of course we don’t want to overdo anything.”

She waited. “Yes, Ms. Katherine,” I replied. What else was there to say? The humiliations were beginning? She was punishing me for my lack of enthusiasm earlier that I was being turned into her slut girlfriend? What else she was planning to do to me?

“When you go in for your conference, select a nice gold chain for a necklace and wear that too, tucked under that collar, so no one can miss seeing the lace. I don’t care how you explain the blouse and chain if anyone asks, but I think afterward you’ll feel a little more grateful to me for what I’m doing. Remember, you agreed to all of this, wholeheartedly and repeatedly. And I saw when we were prepping you for your breast implants that you had sealed your agreement with an orgasm all on your own!”

I swallowed hard. “Yes, Ms. Katherine,” I said a lot more sincerely.

She waved her hand to say that gratitude was unnecessary. “Don’t worry about what people think. If you feel like it, flash your tits at anyone who mocks you. They’re real conversation-stoppers already, those breasts, believe me. Some women would kill for a figure like the one you’re going to have. Finish up the project you’re on, and then turn in your two-weeks notice, and tell them you’re taking off those two weeks as accrued sick leave. I need to change you utterly, Annie, and I can’t do that if you’re spending all your days in some cubicle worrying about people who have nothing better to do than insult you for obeying me.”

“Yes, Ma’am.”

“That’s better. You should know that one more insolent innuendo in your responses would have sent you to work tomorrow in a skirt too. Any questions?”

“Yes, Ma’am. How will we get by without my salary?”

“Don’t worry your pretty little head about that, Andy honey,” she said. “Maybe you’ll work for me in the Clinic. We need to make our records more accessible. You can do that for us. Maybe later on I’ll get you to turn tricks — it would help you develop the right kind of sluttish personality. Which reminds me, we need to make your pretty little head pretty as soon as possible, so you can begin being a girl in public right away without disgracing either of us. Learn by doing! So day after tomorrow we get you a new hair style and makeover.”

The next day’s meetings were arduous, but we got all the understandings ironed out and concluded that I could fine-tune the project completely from home in no time. I thought at first everyone was pointing fingers at my blouse, but I suspect most never even noticed. I suppose they thought I was affecting some

mod style, or a pirate or an 18th century grandee.

Only Becky Davis, our whiz kid from Sales, commented on it. “Very pretty blouse, Andy,” she said. “Looks just like one I once had. I didn’t know you leaned toward my taste in clothes.”

I didn’t know if that was a compliment or not. Becky was thin as a plank and as starved as a model, but she wore her clothes with great style and panache. So I looked pleasant and said nothing.

“It’s so full in front you could grow tits in them and no one would ever know,” she added. “Have you thought of doing that? Have you found yourself a boyfriend who likes big tits on guys?” So her remark *was* intended to be an insult.

I straightened my shoulders and thrust my chest way forward, and my bra poked unmistakable mounds into the front of the blouse. Becky stared! “I already have grown them,” I said. “You should try it some time yourself, and get some guy interested in you for once. Or some girl!”

It was her turn to say nothing.

When I got home Kate was stretched out on the couch in a robe, obviously through with her own work for the day. I changed into the skirt and medium heels she’d laid out for me, and then told her about my interchange with Becky. She was both pleased and amused.

“See, I told you,” she said. “Accept yourself for what you are, right now a man with big boobies, and later a woman with generous boobies, and no one can reach you. So what are you?”

“Right now I’m a man with big boobies, Ma’am, and your property.”

“That’s right. My sissy girl property. I’m very pleased that you’re through working downtown. Those breasts aren’t a mere whim, they’re very important, they’re your passage into a new life. I mean for you to become a passable woman. It will take time and effort, on your part especially. But there will come a moment, you’ll see, when the sissy man disappears in your own mind and the girl of my dreams replaces him. That’s where I want us to end up. When I saw you playing girlie-girlie fantasies at that computer,

lots of things fell into place for me. You’re going to become a girl very soon. Now listen closely, Annie. Do you want to become a girl as soon as possible?”

“Yes, Ms. Katherine,” I said. I realized that wasn’t enough of a response. But I wasn’t really persuaded. And I had one serious reservation. “Ms. Katherine, may I ask you a question?”

“Yes, of course.”

“Ms. Katherine, when I’m a girl, will I still have my…my…male parts?” I was afraid to name them, for fear she’d suddenly be reminded I wasn’t already gelded, pick up the phone, and order up a castration and penectomy to go.

She just smiled. “You poor dear. That’s the last vestige of masculinity a man reaches for, isn’t it. Well, your female hormones will soon render them useless, but you can keep them as long as you want them. I suspect there will come a time when you’ll prefer a cunt, if only because by then you’ll like being attractive to men, and men adore cunts. When that happens we’ll have your “male parts” as you call them turned inside out into a cunt. It’s done all the time these days. Does that ease your mind?”

“Yes, Ms. Katherine.”

“Learn your girlhood lessons well, and I’ll let you masturbate a little, while that thing still provides you pleasure. On rare occasions, when you accomplish something I find impressive, I may even allow you to masturbate until you cum. But your main sexual pleasure from now for a while to come will be from your new nipples– caress them all you want, whenever you wish. It’ll help you appreciate them. Enjoy your femininity! And right now, Annie, it’s time for you to enjoy mine. Here!”

She pulled back her robe, and I saw that she was wearing nothing underneath. I saw the furry triangle of her crotch, and her slit. and her creamy white thighs.

“I promised you could kiss my naked pussy. Now you shall. It’s exactly the same way it was when I brought it home from work a few days ago, a little sweaty, a little pissy, maybe even a little lubricated too, because feminizing you excites me. Is some man’s cum in there too? You don’t know, do you? Well, you’ll just have to work it out on your own.” She smiled to herself and went on, “With your tongue. Come here and lick me now, Annie. This will be a regular reward for you whenever I come home, as long as you do your other work well.”

She shifted her hips slightly and dropped one leg to the floor, then raised the other high onto the back of the couch. There it was! Her pink slit was now perched on the edge of the couch, wide open. I fell to my knees and again buried my face in her crotch, this time slathering my nose into its musky, fermy, sour center, and I began to lick her. She tasted slightly acrid, but sweet, and salty, and fishy, and creamy, and — she was the woman I had sworn to serve with all of the manhood in me, and now all of the femininity too,


and I began to lick and suck and tongue and kiss her more passionately! Was there a love potion in that twat? Really some man’s cum? I didn’t know! It was divine! I loved her! My tongue probed way down and became a prehensile snake. I buried it in her and started to tongue-fuck her.

Almost immediately she started to moan. I ran the tip of my tongue up one edge of her slot and down the other, then up onto her clit, and again into the center line where there lurked, I knew, a deep and mysterious hole fit to entertain a small man’s five inch prick or a large man’s fist and wrist. Then I moved back to her lit again, where I loitered and licked and loitered and labored. She moaned louder, and shook, and screamed, then began to make strange animal sounding growls, and then screamed again. No woman’s cunny was ever cleaned more thoroughly or enjoyably.

When I lifted my soaked face I felt proud. “Very good, Annie honey,” she said, still breathing hard. “I knew it! You will make the sweetest girl anyone can imagine. Next time would you wear that dark lipstick for me? Now fix me dinner.”

I did that too. It was easy. I was in love again. Before I sat down to eat with her, I tried to make my whole face up like a woman’s, as a gift to my precious, my darling Ms. Katherine. I failed, but she looked at it and smiled, and said nothing. That night we slept in the same bed, and in the early morning when she was returning from a visit to the john and the moisture of her piss was on her like rank dew, I kissed and licked her crotch to yet another orgasmic spasm. My own prick was pulsing fit to explode the whole time, but she wanted me to hold back, she said, so she could redirect my sexual energy. Toward who? Toward what? I maintained iron control, and nothing came of it.

…continued in Chapter 3