Letter to the Staff of Sissify – Chapter III

My first visit to a beauty salon the next day was a revelation, all those unguents and mirrors and rollers and comb outs and blow driers and paints and powders and pills. I assumed I’d go in my own clothing so as not to attract attention, but the reverse was true. Kate insisted that morning when we left the house that I should look like the woman I was becoming.

“There will be other women there,” she said, “And I don’t propose to look foolish, coming in with an obvious sissy, a man who wants to be prettied up as a girl! I’d do that to humiliate you of course, but you’ve been a sweet dear so far so there’s no need for it. You’re not perfect, Annie — you should brew my coffee darker tomorrow when you bring me my breakfast in bed.”

She waited. “Yes, Ma’am,” I said.

“But I love it that you thought of breakfast in bed for me all by yourself. And the Eggs Benedict were a nice touch. Today you’ll go to your first beauty parlor appointment already looking female, and we’ll see if you can keep up the illusion while you’re there for. For your own good.”

So she had me wear my undies and a dress she picked out that showed my breasts as distinctly large mounds thrust way forward. She showed me it had “darts” sewn in to allow for them, and told me I’ll need to know all about such things from now on.

“Shirt Waists and unfitted tops won’t do for you,” she said. “No understatement. You’re a girl who believes if you’ve got ‘em, flaunt ‘em!”

And she insisted that I wear make-up, but not brazen, just light liner and mascara, and a pale lipstick. And that I wear my hair in a pony-tail gathered on the crown of my head instead of as usual at the nape.

“That’s enough. If you move with dainty steps and hold your shoulders back, you’ll pass. Your beautician will know of course.”

When the front door was open and I was about to step outside into the sunlight, I suddenly felt a deep pit open in my stomach, and I tried to move my legs — they were in pantyhose and low heels — but they wouldn’t lift off the floor.

“Is something the matter, Annie?” Kate asked just behind me.

“I’m frightened, Ma’am,” was all I could say.

“Big strong mans is frightened to look like an itty bitty girl?” she mocked.

“No, Ms. Katherine,” I said in a small voice. “I’m not a man, I’m a sissy, who is trying to be a girl because that’s what you want me to be, and I don’t want to look ridiculous. I’m afraid, yes.”

There was silence. “Tell me again what you are, Annie. Several times.”

I repeated it. “I’m a sissy, trying to be a girl.”

“Good! Now out the door, sissy girl. You’re dressed appropriately. Be proud of it!”

Still muttering my mantra, I stepped outside. The air felt strange on my legs. A neighbor walking his dog glanced at us and walked on. I felt a little easier and got into the car. Kate drove. The same thing when we arrived. The place was full, and the receptionist didn’t even look up. “Yes,” she said, checking off

my name. “Just have a seat, Annie, and Joanne will be right with you.”

We sat down, and I remembered to smooth my skirt under my bottom as settled onto the chair. “Elbows in,” Kate muttered to me as she handed me “Beauty Culture Magazine.” I glanced at the cover. More articles for women on how to get roundly boinked. “Just theads, dear,” she said when she saw me starting in on one. “I’ll decide when and how and whether you’ll have any sex life at all.”

A neat, short, cheery woman in a purple smock approached. “Annie?”

I nodded.

“I’m Joanne, sissy. Oh, don’t look so mournful! This is the nicest day of your life! Come on, Sis, over here. You can come back for him in about four hours, Kate. We have a lot to do. But you’re right, there’s a lot here to work with.”

Joanne really was nice! I just sat there, and as she snipped and poured and combed and rolled and dried and primped and called over the nail specialist and the ear-piercing girl, she explained everything she was doing, and in between, she told me gossip about other customers. She knew the most intimate things!

“Now this will feel cool, but its a cream you’ll use on your own face every night from now on, Sis. Starting tonight! See how I rub it in with circular movements, just my finger tips? Well, this customer of mine, her name’s Susan but she likes to call herself Suzette, she’s such a petite, dainty, precious little thing, and her husband thinks her ass is made of candy. But really it’s got to be cast iron, because every afternoon while he’s off at the office with his clients earning the money she spends on herself, she’s home in his bed with three, four, five guys from the Truck Depot. Big guys, my dear, and every day! She likes toofers, one in her butt and one in her pussy, you know? Lean back, dear. I don’t know why she’s never been crushed when they hump up against each other with her in between. Well, she told me she was giving up toofers for Lent, but these guys bring each other over to her house, and if a newcomer wants in while the other’s pumping away in her, she never says no. She says afterward she feels like a sewer with all that jism puring out of her. She loves it! And her hubby still thinks she’s practically a virgin, he never suspects anything! See how I brush it, Sis, up from the neck, never down? You’ll do that every morning. Then I hear Mrs. Eldridge is getting divorced, but not from her husband….”

So the time passed.


I emerged that first time a blonde, with darling little curls clustered all over my head and the sweetest tendrils pulled down in front of my ears to soften my face — that was what Kate taught me say right then and there when she returned and smiled her approval. My nails were long and red and I had been taught how to keep them that way. My eyes were deeply shaded from their black liner and heavy mascara through to their blue shadows on my lids and their silvery gray highlights under my brows. It was as complex a procedure as I’d imagined when In was first looking at the cosmetic ads, but Joanne taught me the basics and a few tricks. And Kate loved the effect — I looked wide-eyed and bright-eyed, staring everywhere at the world as if a little perplexed. “Perfect!” she said when she saw that!

During the next few days I learned to do day and night versions of eye-look on my own, until I could fix any defect even while still at the table of any restaurant, with only a slight flourish of a wand. My beard had disappeared during the three days that endowed me with breasts, electrolysized out of existence while I was asleep on tranquilizers and sedatives. So almost immediately my face became what Kate wanted, cute, sprightly, doll-like, the face of a girl who is amusing but not threatening, maybe a girl who’d be a challenge to get into bed but one who might be hard to stop once she got there. She kept training me to look fascinated by anything said to me. And to make perky little movements. And to smile and look a little grateful and a little hungry when I was complimented.

By the third week I took great pride and pleasure in the fact that I could maintain my looks by myself. We shopped whenever Kate could spare the time, and I had lots to wear. She always chose clothes that were slightly brassy and provocative. My new bras and panties were strange lacy whisps of things with oddly shaped openings, mostly from Fredericks of Hollywood, “just this side of whorish, Annie, because that’s how you’ll want to feel.” Each day she had me walk about only in my underthings and high heels for a few hours, so I’d always see myself wearing them in my own mind no matter what I was wearing on top. My blouses and dresses and skirts were a little tight. “They’re for showing off your body to strangers,” she said, so she had me practice sashaying through malls and parking lots in clinging clothes with hips that moved like a pendulum, and I got used to being stared at. Even began to like it!

I practiced my high voice — she wanted a near falsetto from me, though many women don’t talk that way, and lots of tonal range. Each day after I’d moved my bowels she had me use a “Summer’s Eve” douche down there, and then work my finger into my anus coated with KY jelly. “A girl can’t be too dainty down below,” was all she said in explanation. “And besides, doesn’t your finger feel nice moving around in there?” It was a fact, once past the anus my colon felt silky to the touch. The TV game shows and talk shows and soap operas and the women’s magazines began to get to me, until by the second month of my new life when I was back at the salon for retouching I was only one more woman leafing through style books under the dryer and gossiping in my newly trained, slightly squeaky voice, about nails and hemlines and unfaithful wives and cute guys on TV.

It was clear from the start, Kate wanted me to feel kept, dependent. Being attractive the way she wanted was the reason for my existence, and I did work at it, very hard. I really tried! A few times when I forgot some simple feminine thing — I sat knees apart when wearing a dress, or I sat knees together when I was wearing jeans — she would criticize me and punish me by denying me access to her sweet, dear pussy. Around the fourth week I started to cry when she used a rough tone with me — I couldn’t help it, I’d forgotten that she wanted me to be forgetful, and silly, and sprightly, not a real ditz but the kind of girl even a shy guy could admire close up and feel manly with. Kate credited it to my hormones and forgave me when it happened, and I was so grateful that I crawled between her legs and licked and sucked and kissed her sweet cunny all night long. And she let me, too!

One evening during the fifth week we were both putting night cream on our faces when she looked over at me and said, “Annie honey, you have made marvelous progress, by leaps and bounds. I’m sure that in your heart you really wanted this.”

“Yes, Ms. Kate,” I said. “I’m sure now too!”

“I think it’s time you enjoyed some of the distinctive pleasures of being a woman,” she said.

An odd statement, considering that I was that moment wearing my softest, laciest nightie, pink and black, and had put up my hair, and was removing the makeup I’d worn all day. I said nothing.

“So tomorrow you won’t prepare dinner for when I get home. We’ll double date and go out for dinner.”

I felt a shocked and distressed, both at once! Kate with another man? Me with…a man?

“But I’ll go easy with you this first time. With Claire and Wilmer. We’ll meet them at the Pavilion for dinner, and then come back here afterward. Your red mini with all the flounces will be just right. If you can walk and move through the dining areas with just a touch of dignity, they may not take you for a provocative tart and throw you out at first glance.” She smiled at me.

I was nervous all the next day, and kept adjusting my make-up, but at the actual dinner I was a great success. Claire looked at me with a sardonic expression, delighted and slightly mocking!

“Andy darling, you never were much of a man, but how you’ve changed!” she said, as we clasped both our hands and leaned forward to touch cheeks to each other, as women do who don’t want to mess their faces. “You’ve taken to all this so well! Don’t tell me you haven’t wanted it all your life! I never understood what Kate saw in you, when you were still playing at masculinity. Probably that you were really a closet fag!”

Kate had reminded me when we were walking from the parking lot to meet them that Claire was often insulting, but Annie was brassy, lively, and incapable of feeling offended by insults.

“Why thank you, that’s a very sweet compliment,” I gushed. “Oh, Claire, I haven’t had a chance yet to thank you for these wonderful titties you gave me that first weekend! They’re really all anyone needs to be happy, whether a man or a woman! And aren’t you lovely tonight! Is that the dress you were wearing last time we saw each other? It looks even better tonight! And Wilmer, how nice to see you again! I’ve really wanted to get to know you better!”

And I smiled at him, a restrained but unmistakable come-on Kate had made me practice repeatedly, even though I was thinking meanwhile that there was nothing much in him to get to know. Wilmer smiled back, nervously restrained with Claire close by, but I sensed he relaxed a little when he concentrated his attention on me.

Encouraged, I took his arm, thereby claiming the only male in the company for myself, and we followed the Maitre’ d to our table. I saw at once that my red mini really was a sensation for this restaurant, and decided to walk on Wilmer’s arm as if everyone in the place was applauding. Every other woman including Claire and Kate was wearing black or subdued shades, with hemlines below the knee while mine barely covered my buttocks, and my flounces exaggerated every movement of my breasts and hips. Far from embarrassed that I looked so flamboyantly feminine, I felt pleased. Attracting Claire’s husband was a kind of petty revenge against Claire, who had been part of the conspiracy to make me into what I was. Of course I didn’t dare feel that way toward Kate. Or want to.

I looked back, and was surprised to see that the two women walking together behind us were watching us with wide grins on their face, Kate delightedly telling Claire something, Claire giggling in response. As Wilmer led me to our table and held out a chair for me, I realized with a shock that I’d been set up! They’d wanted me to resent Claire, and to try to steal Claire’s husband from her! They’d wanted me to set up a liaison with a real man! And I’d done it! Just how far did they want me to go? I was suddenly frightened. But I just clutched Wilmer’s arm tighter, and then as I sat down I trailed my fingers down his arm. I’d started it, so I’d finish it! As he sat down too I looked into his face the way the magazines had advised me, eyes wide with interest, and asked him what he liked most about his work, and what he’d done he was most proud of. And marveled with prettily pursed lips as he told me about some obscure accounting practice he’d reformed.

Kate had to cue me a few times to remember my training, be very delicate with my hands when holding my silverware and wineglass, primp my curls up in back with my palms now and then, be very bold while looking around the room, and look the waiter up and down with hooded eyes when he bent over me to take my order, as if I were sizing up a delicious slab of beef. Now and then, shoulders back and shake my breasts back and forth — I did that once in Wilmer’s face, and he almost went catatonic!

We went back to our house in separate cars, and Kate established her authority over me again as soon as we were alone. “You enjoyed being a woman tonight, didn’t you, Annie?” she commented.

“Oddly, I did, Kate” I answered affably. “It felt almost normal, and what was new, like teasing poor Wilmer, was actually fun.”

Her face darkened. “‘Kate’? You call your Mistress ‘Kate’?”

I immediately started apologizing. She cut me off angrily.

“You know what you are going to do tonight when we get home, Annie?”

“No, Mistress Kate.” I was suddenly fearful again.

“You are going to seduce ‘poor Wilmer.’ You are going to go all the way with him! You remember those cock sucking lessons you were studying when I caught you at it? Final exam time! You’re going down on him, Annie, and by tomorrow morning you’d better know what he’s like in your asshole too!” She sounded furious!

I shrank down in my seat, terrified. She glanced over at me, and suddenly broke out into a sweet smile. “Don’t look so scared, honey! That’s what all girls do when they get guys interested in them. Because it’s fun all around. You’ll see. You knew it was coming, didn’t you? Well, sweetheart, with you, it’s coming sooner than either of us had thought. Being a woman felt normal to you? We’ll see! Maybe those hormones are acting on you more powerfully than we’d anticipated. Go with them! The moment we get into the house, start working on it!”

We pulled into the driveway, and she pulled the parking brake forcefully, then looked at me with a level gaze. “Annie, it’s this way. Tonight you will seduce Wilmer and get him to sleep with you, and tomorrow when he wakes up he’ll have a smile on his face. Then maybe I’ll feel I want to marry you before too much longer. Or if you fail at this simple feminine task, then tomorrow you’ll begin parading yourself down by the railroad station, learning how professionals do it until you’re as good at it as any of the others. That’s if you want to have anything more to do with me.”

I said very seriously to her, “I’ll do whatever you say, Mistress Kate. With all my heart! Anything!”

She sounded pacified, and patted me on the leg. It felt nice on my nylons. “Enjoy it, sweetheart. This is what it’s all about.”

So I just thrust away from me all thoughts of humiliation or macho pride. Here was a man and I was a cute woman who wanted into his pants, and no other feelings applied! When Wilmer and Claire arrived and I’d gotten us all n ightcaps I settled down next to Wilmer on the couch and snuggled into to him. I didn’t dare look at Claire or at Kate, and it didn’t seem odd until later on that they both left us alone, watching at first without saying a word. I remembered some things from my magazines, and while I asked Wilmer to tell me more about his wonderful bookkeeping innovations, I trailed my fingernails up and down his thigh. Now and then, as if absent-mindedly, I caressed his chest in the vicinity of his nipples. Once I reached across him to pat him on his far cheek to console him when he sadly told me his supervisor didn’t fully

appreciate him, and when I had turned his face toward mine with the palm of my hand, I leaned forward and opened my lips slightly, and closed my eyes, and waited.

And then opened them again. He was looking at me bewildered. “Claire told me that tonight I should be on my best behavior,” he said. “I don’t know what that means.”

“I do,” I said in my huskiest woman’s voice. And I moved my hand from his cheek to the back of his head and pulled his face toward mine. He kissed me. I could feel his beard stubble against my smooth lips and cheeks, and his tongue went into my mouth and I began to lick it with mine, and I gently put one of his hands on my breast, and he began to caress the nipple as it rose up, through my dress and bra. Again I began to melt from that exquisite feeling in on the tip of my breast, and a yearning began to build and spread through my groin. I moaned and twisted to press my whole body against his. We embraced passionately, and we writhed against each other, while I tried to swallow his tongue. Then he took one

of my hands and put it on his crotch. There was an enormous bulge there! Huge! It crossed my mind I was right, why Claire kept him on, and I unzipped him while my mouth still clung to his, and then pulled out an enormous weight of meat! My eyes still shut, I began to stroke it as if it were a large puppy. And I heard Claire’s voice behind me,

“You were right, Kate. They really are going at it. What in the world did you tell him?”

“The same thing you told Wilmer, that he’d better, however he really felt about sex with other men, or else! But I must say, I didn’t expect there’d be this much heat between the two of them. I really think that right now Andy’s convinced he’s a real girl!”

“Just look at Wilmer’s face. I Know Wilmer’s convinced of it! You’ve done wonders with Andy, Kate. And he looks so cute! That darling dress! I’d love to see the rest of his outfits. Shall we get to bed now? Let’s go upstairs now, sweetheart! The way they’re behaving is making me feel hot to put my hands on you! And other things!”

“Just a moment, love,” Kate answered. “I want to see something else first!”

By this time I realized I had better get down on Wilmer right away, or he’d blow his wad and tomorrow night I’d be hustling tricks downtown on a technicality. So I said, in my most seductive voice, “Just a moment, sweetheart. Just relax!” And I disengaged from him with a sigh and another erotic squeal, and slipped down on the couch so I could take his prick into my mouth, and looked for the first time at Wilmer’s equipment.

My first thought was, if that’s a man, I’ve got no business imagining I’m one too. The thing looked longer than a tennis racket handle, nearly! There was no way all that could fit into my mouth! A huge purple helmet with a single eye stared at me, my fist barely encircling the shank just below it, my deep red fingernails pressing their tips lightly onto the underside. There was a large drop of pearly white liquid sitting on top, almost obscuring the piss hole opening. I leaned over and lapped it up. It tasted sweet, salty, creamy. I kissed the eye, then tongued it, then settled Wilmer’s whole cock head into my mouth and began to move down on him.

“That’s what I wanted to see,” I heard Kate say. “That was what I asked Andy way back when I first caught him dreaming about this moment at that Sissify web site, would he want to lick the precum first, or just head straight for the main action. Now we both know. He’s a natural cumsucker, even before he’s a cocksucker. He’ll be very useful to us!”

“Yes,” I heard Claire say. “With practice he may get to be as good at sucking cock as you are. And at drinking cum out of you, the way we make Wilmer do it now as a punishment. This is a much better arrangement. I’m really so glad you thought of it, sweetheart. Between the four of us, look at the possibilities! Now we have three usable assholes not counting Wilmer’s, assuming that Wilmer gets into Annie’s tonight and opens it up.”

“He will,” Kate said. “Annie will see to it. I’ve seen to that! And I really do think that when it happens he really will love it. He really is a slut! Just look at him!”

Claire continued her inventory as I began slipping my dark red lips up and down Wilmer’s shank, sucking gently, licking the underside, and hearing him groan deep in the back of his throat. “And between us,” she said, “we have three functioning cocks until those heavy doses of hormones reach Annie’s, then two. And one real vagina for servicing with Wilmer’s cock or mine, whichever you want, the way we’ve been doing it since we first met. We have one submissive straight male, Wilmer, with a dominant transsexual wife, me, now getting deep into an affair with a brand new transsexual woman, your submissive boyfriend. So Wilmer’s happy too, I should say!”

Wilmer began thrusting up at me, and I tried not to choke on his meat. I gripped with both hands the part of his prick below where my lips could reach, and gently jerked him off as my lips continued to pulse and rise and fall on the upper part. I heard Kate’s voice,

“And now I’ve got two good looking women to sleep with whenever I want, one of them proper and well bred, you, and the other getting on to be a wonderfully flirtatious hussy, Annie. I have your cock to fuck, Claire, or Wilmer’s when I want a real man. And that cock of Wilmer’s is a prize! Just look at it! Annie can barely get the top half of it into his mouth! And I can have Annie’s cock too, if I want it, for the time being. But I think I’ll leave it alone — it would interfere with his feminizing if he got used to using it again. Anyhow, I’m sure he’ll want it to be a vagina by the end of the year.”



Wilmer put both hands on my head gently, and held me over his giant prick, and began to move me up and down in his own preferred rhythm. I pulsed my lips as rapidly as I could as they slid along his shank, and meanwhile continued to jerk him off.

“Kate, do you have any idea how Annie’s desires will settle down when you’ve finished with him, when he’s finally a her? Certainly he can be our house maid, what with the three of us working and earning good money. And you say he’s a data base expert too? That’ll be useful at the clinic. You should plan to marry him soon I think, while he’s still a man, while it’s still legal. He’s slipping fast. Just look! Now he’s doing Wilmer’s cock like a starved animal!” There was a long silence, and then I heard Claire add in a subdued, almost fainting voice, “Oh, Kate, that was so wonderful! Do it again to me? Or can Annie do it to me now?”

I could feel Wilmer begin to tense, and his huge cock swelled until the veins up and down it stood out like cords. I began to suck deep, with all the pull my cheeks could muster!

Kate again. “No, let’s leave him alone with his very first boyfriend. Just look, isn’t that sweet? And I did promise him his first assfuck too with that glorious thing of Wilmer’s. And you know Wilmer’s tongue is magic on anyone’s tits, and Annie loves that sensation — she plays with her nipples all the time. I’m sure she’ll be in love with Wilmer by morning. Let’s just go to bed now, baby! I want to feel you in me, Claire, pushing deep, deep into me! That wonderful cock of yours! I’m so glad it’s still functioning!” Kate’s voice that sounded nearly hoarse.

I heard their footsteps on the stairs, with shufflings and silences, when I suppose they were gripping and kissing each other. Then the door to our bedroom upstairs closed.

At that moment I felt Wilmer’s pelvis rise up out of his seat and his prick thrust deep into my throat and begin to pulse. Cream filled my mouth, and I swallowed it as fast as I could! It was so delicious! I’d never dreamed a man’s cum would taste so good, and feel so satiny on my tongue and lips! It was so glorious at that moment, being a woman!

When he’d finished pumping and I’d swallowed it all, and licked him lovingly, I smiled up at him, then sat up to kiss him on the cheek. I remembered from what Claire said that he wasn’t crazy about the taste of cum, not the taste of her cum in Kate’s cunt, anyhow. His cum? I put it out of my mind. “Come on, lover,” I said. “There’s lot’s more! Let’s get to bed.” He was still breathing hard, and he looked at me. Then he smiled, shyly, and the two of us got up and headed for the guest room.

The next morning when I woke up, there were Kate and Claire wearing negligees, hair pinned up and arms around each other, standing in the doorway looking down at us with smiles on their faces. I was curled up on Wilmer’s hairy chest, and he had one long leg draped over me, and I still had an arm encircling his neck, where I’d hugged him to sleep. My rear end felt terribly sore, well-used, but somehow wonderful! My breasts too! I saw that Wilmer was smiling too as he snored gently. And I know I was.

“Honey,” said Kate. “You two look so precious together! We’ve brought you your negligee — I know you’ll want to look pretty when Wilmer wakes up. But meanwhile, we need to talk. There are some things you may not know. I want to tell you what they are, and put a proposal to you. I still own you, but this involves more than just your relationship with me. So I have to get your free consent. If you can agree to what I’m about to say, I’ll accept you as my husband and my steady girlfriend, and we’ll get married as soon as we can decide on our bridal gowns and make the other arrangements. And find a larger house, because there will be four of us living in it. I’d better explain.”

And she did.

So, dear Sissify Staff, there’s where I am now. I love my new life! Somehow during my month or two of living as Ms. Katherine’s submissive sissy, I really did turn a corner and became a real woman. A real transsexual woman. I live now with Claire, a shemale transsexual woman who is also my fiancee’s girlfriend, or sometimes her boyfriend, and is also my doctor. And I’m beginning to get to know her intimately myself. Then there’s my fiancee Kate who is my beloved Mistress and owns me, a born woman. And there’s sweet, darling Wilmer, an ordinary man with exceptional gifts – as I understand it, I’ll have to share Wilmer with his wife and my wife, but that’s OK, there’s lots of him to share. So my life is full, and my other openings are too, often. I feel so pretty, being wanted by so many people, and so satisfied too!

And I owe it all to you. I just wanted you to know that I’m grateful.

Yours sincerely,

Annie