(as dictated to Vickie Tern)
Dear Sissify Staff:
I think you should know how my signing on with you has changed my life. I know I’m happier now by far, but that isn’t up to me any more. My girlfriend now owns me and she’s so satisfied with me that finally she has decided to marry me. But ours hasn’t exactly been a typical romance. I’d better tell you about it.
I’ve always enjoyed imagining what it would be like to be a girl, to look as pretty and dress the way girls do. I’ve downloaded lots of stories about it from the Net. But I’ve never had the courage to try it myself, not even to try on a pair of panties. The thought always got me trembling. My urges got so powerful they frightened me — I couldn’t tell where they’d lead. That’s why I joined up immediately when I saw your web site instructing me how to become a virtual girl. It was fun obeying your orders, and pretending I was doing all those feminine things, and then reading your encouraging messages.
Well, it happens that a couple of months ago I was reading where you explain to sissies how to please their men by sucking their cocks, when suddenly I heard my girlfriend’s voice just behind me.
“Oh, my!” she said. “How fascinating! But you read so slowly, Andy! Scroll down so I can see which they advise you to do first, lick the pre-cum off the tip of the man’s cock or just take the whole head into your mouth! Which do you do?”
I was shocked! Never so embarrassed in my life! There behind me was my girlfriend Kate calmly reading the screen over my shoulder! How long had she been there?! What must she think of me!? That would never have happened last year when she was still doing office work, and wore perfume and clicked around all day on heels. I always knew when she was home, from her scent and her sound. But then she finished her nursing degree and took that job in that downtown clinic, and now between her rubber-soled shoes and her silent ways she could be anywhere! Like, just behind me!
“Is this what you dream about when you’re not working?” she asked. “Becoming a girl? Tell me, sweetie, right now is that what you are in your own mind? If that what you want to be? Do you want to wear pretty clothes, and look cute, so boys will like you? I mean even when you aren’t giving them head?”
“I e-mailed a long report in this afternoon,” was all I could think to say. “My boss says he’s happy with it. I thought I’d just look around a little,” I finished vaguely. My face was flushed deep red because now the screen was illustrating the best ways to slide your bright red lips up and down a cock so a man will cum in your mouth.
“Let’s see what this place is, what the web site is where you like to just look around a little.”
Before I could reach for an off-switch she leaned over and took the mouse and began clicking her way back and forth through the whole Sissify web site. I just sat there, humiliated. There was no escaping even the name, “Sissify.” That is what it was for. For feminizing men. She glanced at medical papers on hormones and stories about wives and girlfriends converting men into their sisters or whores and different domineering women demanding that their sissies wear panties and brassieres all the time and pictures of men fully dressed as women with real breasts and real cocks too, and many appreciative letters to the staff thanking them for their help. Now and then she glanced at me, a slight smile curling her mouth. In no time she’d seen it all.
“Well,” she said. “Very interesting. I see you didn’t just stumble into this garden of delights. You had to join up, didn’t you, uh, ‘Annie.’ That’s your screen name, isn’t it, sweetheart? That’s so sweet! You even had to fill out an elaborate questionnaire, didn’t you? You really want this, don’t you?”
She remembered something. “Did you remember to tell them how once you volunteered to rinse out my soiled undies, and I let you? I thought it was an odd offer at the time, and I wondered about you. Did you sniff them? Did you try on some of my prettier panties afterward?”
“No, I didn’t dare.” I had nothing else to say. I sat there clutching my hands in my lap. Nowhere to hide! I felt devastated!
“You didn’t dare follow out your little urges? You wanted me to tell you to wear my panties?” Her voice was no longer mocking, but it had taken on an odd lilt.
I said nothing. That was what I wanted, yes.
“You know, Andy dear,” she went on. “I’ve been thinking about your proposal to me, your wanting to marry me? I mean, we do live together and all, but I’d had no idea you felt that way toward me, that you wanted to spend the rest of your life with me and all. I was really deeply moved, Andy honey, really, and I’ve been looking very deeply into my own feelings and needs since then. Into what
I want in a husband. But this puts a different color on a decision like that, doesn’t it? It does make a difference.”
I got frightened. “Kate, please!!” I said. I’d blown it! She’ll never want to marry me now! Oh, God! “Kate, this isn’t me!” I almost started to cry. “I’ve never done any of these things!”
A surprising question. I turned to look behind me, and found I was looking straight into her eyes. They were quite serious, curious, not at all scornful. I couldn’t answer her. Because I’m a real man, not a sissy? Because the idea scared me? Would pretending to be a woman scare a real man? Any answer declared that I was either a wannabe sissy or a pathetic wimp! So I said nothing.
There was one pathetic wimp in our circle we saw socially now and then, and I’d always felt sorry for him. In fact just the previous week Kate’s best friend Claire had brought him to dinner with her — they were married. Claire is a strong-minded, no-nonsense doctor where they both work, stunning and self-assured, and Wilmer looks to be her completely opposite — he’s good-looking enough, and well-built, but very quiet, even timid. I think he’s an accountant. And Claire keeps him that way. Wilmer spoke up only twice all evening and she put him down both times, and he looked apologetic both times.
After they left we talked about mismatched couples. Kate thought Wilmer an interesting choice in a man for a dynamic woman like Claire. “She likes to be in charge, I suppose,” she said. “There’s something to say for that.”
I thought so too. “I guess Claire likes wearing the pants. Or maybe she enjoys Wilmer so much from the waist down — he looks pretty fit, physically — that she doesn’t mind any deficiencies higher up.”
Kate started to say something about that, then lapsed silent.
But now, I thought, she’s surely thinking I’m another Wilmer! Oh, God!
Suddenly she came around in front of me and pushed my keyboard to one side and turned and leaned her round rump onto the edge of my desk and then lifted up and sat down right where the keyboard had been. There just under my face was her crotch, covered by her tight jeans, the deep crease between her legs visible despite the heavy denim. Her labia may have been swollen the whole length of her slit. Was she excited about something? I couldn’t take my eyes off that crease. Was the denim dark there, because she was a little wet?
Now her body was blocking the screen. “Never mind these games you like to play with your imagination,” she said. “Let’s see what you’re really capable of doing. Do you really want to be my submissive sissy girl, Annie honey? To do everything I tell you? Let’s say I want you to kiss my pussy, right there where you’re staring? Would you want to?”
There was safety in honesty. “Yes.”
“But would you do it? Kiss it just the way it is, just because I tell you to? I’ve had no shower all day, and there’s sweat and who knows what other kinds of dried moisture down there, maybe even some pee that never got wiped away. And who knows what else right now.” She wiggled her bottom on the desk a few times, tempting me. I thought about it. We’d never done any oral sex, just a lick and a promise once, right after we’d both showered and gotten into bed. She didn’t seem to want it, at least from me. So this was a test of some kind.
“Yes,” I said.
“What if I’ve just been with another man, and haven’t had time to clean myself up. Would you kiss me there anyhow? Like right now?”
Now she was playing with me. There haven’t been any other men. There couldn’t have been. “Have you been?” I asked.
“That’s not the question. The question is, would you if I told you to? Now that you’re worried, why don’t you ask me to let you kiss my pussy? Are you afraid to ask, sissy girl!”
“Please, Kate,” I blurted out desperately, trying to show her I was a man, not afraid to ask. “May I kiss your pussy?” There it still was, that magical crease curving down below her pelvic mound.
I thought a moment. I knew she was a quick study, and I couldn’t be sure what she’d absorbed while she was surfing her way through “Sissify.” So I went all out. “Please, Mistress Kate, may I kiss your beautiful cunt? Please?”
“Maybe,” she replied.
She sounded as if she were enjoying this new teasing game. I didn’t dare look up and break the spell. It isn’t polite to look directly at your Mistress’s face when you are being dominated.
“Annie, I don’t think I want you to call me “Mistress,” except maybe when I need to be strict with you. But you can’t call me ‘Kate’ any more. It isn’t respectful from a sissy-girl. “‘Kate’ is for an equal, for a boyfriend or a girlfriend. And you aren’t my boyfriend right now, and you aren’t my girlfriend either. Not yet. So you’d better call me ‘Ms. Katherine’ or ‘Ma’am’ until you’re one or the other. Are you willing to serve me unquestioningly, Annie dear? To do everything I tell you? To be mine? For me to own you?”
I was absolutely entranced! This was too good to be true! Here was my actual girlfriend playing my favorite fantasy game, and I never knew she even knew about that kind of thing! Maybe we could stretch this out through the entire weekend? “Oh, Yes, Ms. Katherine!” I replied. I glanced quickly up, then shyly back down to her crotch again. She was indeed grinning broadly to herself, delighted about something, and from the gleam in her eyes I could see that her mind was racing away at a mile a minute! “Yes, Ma’am!,” I repeated for emphasis.
“Everything? I mean it, Andy! I really mean it! Are you sure you don’t want to back away!”
What could she have in mind? I didn’t care! I was ecstatic!
“Yes, Ms. Katherine.”
“Then in token of your new servile status you may touch your nose and mouth to my pussy and sniff me once, and then kiss me through my jeans. Later maybe I’ll let you smell my naked slit and lick up anything you find there, if you can prove you’re really sincere, and if you do everything I ask. Not yet.”
She paused for a moment. I could tell that all kinds of switches were closing on plans in her head. “Then, Annie dear, I want you to go up to our bedroom and strip yourself naked and wait for me to join you there. I need to make some arrangements down here before we continue with this.”
I hesitated. Had she finished speaking?
“I should have known about this streak in you, Andy, or now you’re ‘Annie,’ aren’t you? But I can’t say I’ve ever suspected it! Well! It couldn’t be more convenient!”
“Go on, go ahead! Hurry up! Kiss me, then upstairs quickly, and wait! I’ll want to look through other files in this computer of yours, too, and see what else has been on your mind. I want to see what else you like to think constitutes the good life.”
So I closed my eyes and leaned forward and nuzzled her crotch. The denim was in fact damp, with a faint end-of-day body odor, like perspiration, a little sour, and a little musky, but nothing specific. I pushed my face deep into her, then kissed her gently. She responded by pushing her pussy back into my face ever so slightly, just once, as if nodding in acknowledgement.
Then not daring to look at her again I stood up and ran out of the room, up into our bedroom, and I stripped down. I was still terribly embarrassed, but now also terribly excited, and I had this incredible boner, the biggest and hardest I’ve ever had! Nothing like this had happened between us in the whole time we’d been living together, nearly two years! It had started out as a pairing of convenience, I had the whole house and she had money to share the rent. Then it quickly become a bedding down of convenience too — we liked each other and we got on, and we slept together whenever either of us wanted to. Then after a while it looked as if we were going steady. She had other friends, and I did too, and we had no specific understandings and made no exclusive claims on each other, but there we were. Little by little my other really intimate relationships dropped away. Kate worked long hours, days and nights sometimes, and she took a girl’s night out with Claire or some other woman from work now and then, to unwind with them. But otherwise we’d become a close couple.
Not long ago I realized that I was in love with her. I couldn’t stop thinking about her. She’s tall, with smooth dark hair that just barely curls in to hug her neck above her shoulders, and huge eyes and wide cheekbones, always with a grave but gentle expression on her face, and she always moves gracefully, perfectly self-assured. She’s everything feminine I’d ever wanted! And she has this positive way about her, touched with playfulness. I realized I’d do anything for her!
So I finally got up the nerve and asked her to marry me. I wanted us to go on forever. She’d never suggested to me that she felt the same way about me, but she listened to me carefully, I thought affectionately, and then quietly she’d told me she’d let me know. It might take some time, there were things she wanted to think about, she said, but her answer for now was not ‘No’ and I’d have to be content with that.
But now, I thought despairing as I sat on the bed naked, waiting for her, the odds for a ‘Yes’ had dropped to zero. My cock shrank down.
After a long half-hour, maybe more, she came into the bedroom. In between I heard her make a couple of phone calls, and mutter some things in a low voice, and share a laugh with someone at the other end once, someone female I figured because she finished the conversation squealing in delight and giggling about something I couldn’t quite make out. I was sitting on the bed waiting for her as ordered. No big deal, we’d seen each other in the buff almost from the moment she moved in. It was a matter of convenience, two
people living together and sleeping together and working odd hours.
She shut the door behind her. “I see you haven’t learned some of the things I’ve learned while scanning your interesting little collection of smut. First of all, what does a sexual inferior say when he’s been permitted to kiss his Lady’s private parts? You came here without a word.”
“Thank you, Ms. Katherine,” I instantly replied, making a mental note never to forget that courtesy when we next got to play this game together.
“Do you know how to curtsy when you say that, sissy girl?”
I stood up and tried. Right foot back, hands at sides, bend the other knee, and bow. Or something like that.
“And how does a sissy await a Mistress when she’s told him to wait for her?”
I immediately fell to my knees and pushed my forehead into the shag rug that covered the floor. My cock became hard again, crammed between my belly and my thighs.
“That’s better,” she said.
Then for ten more minutes, not a word from her. She went into her closet and rustled among the clothes hangers, and she opened a locked cabinet where she kept different things related to her work, and closed it again, and she hummed to herself for a minute or two, I imagined she was doing something that didn’t require her full attention. I heard her sit down on the bed behind me, and I worried that now I was presenting my backside to her, high up in the air, mooning her. That didn’t seem very respectful. But I didn’t dare raise my head or change my position.
My penis gave a little leap at that, and I settled in to listen very carefully, eager to play the submissive some more with her!
“I told you before that I was going to test your sincerity. I mean really test it. What I have in mind is not a game, though I’m sure you still think it is. I hope you’ll like the new relationship I have in mind, and that afterward you’ll truly appreciate what I’ve done. If you do, we may even end up married after all!”
My heart bounded up at that, and I felt it beat powerfully inside me! Hope!
“But not everything a sissy girl ends up doing is necessarily what she expected or wanted to do in the first place, is it, Annie?”
“No, Ma’am,” I muttered, my mouth muffled by the thick shag rug. My knees were grateful for that rug at the moment. Kate apparently had a plan now fully ripened in her mind. Did it include whipping, or torture? I wasn’t into pain of any kind, as my knees already testified. I hoped not. It surely involved the entire weekend the way I’d hoped, because she’d said “afterward,” and talked about how we’d “end up.” Maybe even married!
“I saw from all those stories you read downstairs what turns you on. Not cruelty, but humiliation. You really want to feel yourself being transformed into a woman. Any of your usual manly pride or dignity has to be melted down, made to feel uncomfortable, even intolerable, so you’ll be eager to collaborate with me as I reshape you into what I want. That’s what assures me you’ll obey me in everything, isn’t it? That my way becomes the course of least resistance for you. Not what you think my way ought to be, and not your way. My way!”
Kate had this incredible ability to get to the heart of things! I was enthralled! “Yes, Ms. Katherine,” I said. “That’s it exactly!”
“Your opinion whether I’m exact or not is not welcome, Annie!” Kate snapped. “I asked you for a simple ‘yes’!”
I cringed even further into the shag rug, my mouth now filling with the yarn, but I dared not lift my head. “Yes, Ma’am,” I said muffled.
“And you know from your stories that sissy submissives often get more than they bargained for, don’t they? Mistresses go much further than their slaves mean for them to go, don’t they? That’s where the excitement comes in, doesn’t it? From feeling that things are out of control, that control has passed from your desires to hers, that you’re now helpless to resist her desires, that you’ve made yourself her creature. Don’t bother to answer this time. I know this is so.”
I writhed for just a moment to try to dislodge my mouthful of shag rug. It was effectively gagging me. But since my forehead had to stay plastered to the floor, my mouth filled all the more.
“All right, Annie, you’ve been warned. You know now that I understand not just the rituals of this game you want to play, but its soul. And that I understand your soul! That if you are to be my servant, you’ll be my kind of servant, not your kind. My slave. That I’ll possess you absolutely. And I mean for life!”
She paused. Was she talking about marriage? No, not exactly. Now I felt genuinely frightened. But so deliciously! She said she’d go even further than I’d dreamed! Was she serious? I really couldn’t tell. But that’s the way this game had to be played! She had such a marvelous instinct for it! I was so absolutely convinced she fully meant everything she said!
In the stories I’d read, whenever a sex-slave accepts his status, his Lady padlocks a leather collar around his neck, engraved with her name. Something like that. I waited for Kate to suggest something like that. And that’s what she did next!
“Now Annie, you know that sissies owned by their Ladies always agree to wear some kind of symbol of their servitude. It’s always more or less permanent, not easily removed. I want you to wear my symbol every hour of every day, at work, at home, in the shower, in bed, everywhere.”
I was positively enraptured! Just as I’d always hoped! Sweet juices rose into my distended prick! In my extreme crouch, squeezed between my pelvis and my thighs, it was perilously close to exploding, and in buckets! I had to distract myself! I tried paying not-too-close attention to Kate’s words, but it was hard.
I’d been dreaming of this moment much of my life! Would Kate now fasten a dog collar around my neck? Wrap leather thongs around my genitals? Lock a chastity tube onto my cock? I was trembling!
“Now Annie, you are going to wear a special pledge to me that’s unmistakable! So you’ll never forget who owns you, and how I own you, and for what! I know you still have to function in the real world, so it won’t be too visible to the casual eye. In most circumstances you’ll be able to hide it. It won’t be part of the way the world sees you, or how you think they see you. Not unless I tell you to reveal it, as I probably will soon, not right away. So for now it’ll be something just between us, and of course anyone I may choose to tell about it. You’ll feel too ashamed to tell anyone about it at first, I’m sure, too humiliated. Until you’ve re-centered your identity and become what I want you to be. Then you’ll feel proud of it, and then I know you’ll want to display it openly.”
Mysterious! Not some kind of cock-binder? A very thin slave collar to wear under button-down dress shirts at the office? An ear ring in a pierced ear? She seems to expect I’ll wear it all the time. Well, all right, clearly she doesn’t mean to disgrace me with anything obvious, some massive restraint on my neck or my ankle that would raise embarrassing questions. She wasn’t cruel. I felt utterly devoted to Kate at that moment. She knew my needs, and I knew she wouldn’t betray them!
“Once again, Andy! ‘Andy’ for the last time. Think of this as the most crucial moment of your life! It is for me too, because whether you know it or not, and I’m sure you don’t, you here on your face with your ass in the air in absolute surrender to me happens to be just perfect for me! It solves a big problem I’ve had for some time! So! Andy, do you accept my guidance in all things from now on. As you would put it, will you obey me as your Domme, or Mistress, or Dominatrix, or Lady, whatever you call such women? As your owner? Do you offer me your most precious gift, your absolute obedience? Whether or not I choose to care, or even seem grateful? Am I the one person you will love, honor, and obey, and have and hold in sickness and health for as long as you live?”
Was she marrying me? Was she agreeing to marry me? No, but I was delighted anyhow. In her mind I was marrying her! That’s half of it!
Now she was silent, waiting patiently for my answer. All this only an hour or two after she’d walked into my study and discovered my secret fantasy life! What other sexual games could she conceive for next weekend, or whenever we both became weary of this one, I wondered. What an incredible woman!
“Yes, Ma’am,” I remembered to say despite my excitement. “Yes, Ms. Katherine. Yes, my Lady! I do!”
“I heard you, but this is important, so I want to ask you yet again. And to warn you yet again. For the third and final time, Andy. I have in mind some things you may love in fantasy but not like in reality at all. Not until you become the creature of *my* fantasy. Are you willing?”
Pain? Torture? I hoped not. Fabulous tests of endurance, of my devotion to her, of my ability to hold up under enormous hardships for her sweet sake? I’d love that! I loved her!
“Yes, Ms. Katherine, I am willing!” I finally managed to say it! I never felt more excited in my life! My heart pounded! I was near fainting! “Please! Whatever you wish!”
And suddenly a rich joy rose up unbidden and uncontrollable from deep in my groin into the base of my prick! I couldn’t help it! I felt a ravishing tension rise up in my bowels and become a rainbow glow, and suffuse itself through all of that part of me thrust closest to her, filling my thighs with exquisite bliss. My ass clenched and quivered over and over, and then a glory spilled out into a rapturous spurt after spurt of hot cum squirting all over my belly and chest and even in splats into my mouth, crammed as it now was with yarn from the shag rug! My penis was so squeezed so tight now between my thighs that I couldn’t feel its spasmodic throbbing, but I felt my body go incandescent! The entire lower part of me went into orgasm!
Which may be why I felt nothing at all from Kate at that moment. I expected her to fasten the collar, or attach a lasso to my balls and lead me away for binding.
She did no such thing. In fact she didn’t even know I’d just enjoyed the greatest climax of my life. As the glow subsided I realized that the whole grand process had been hidden in the deep folds of my belly and thighs, and my cum wasn’t evident anywhere just yet.
She merely resumed speaking. But this time I heard a note of elation in her voice, even though she was trying to maintain the same controlled tone she’d used earlier. Not casual, though a touch negligent. Firm, the voice a Mistress should use when speaking to her servant. But now it also sounded exultant.
“Annie, there is no going back now. You’re already changing! The two pricks you just felt in your rear end were two intramuscular injections to help get the process under way the moment I had your fully informed consent, tape recorded and repeated three times.”
“Both injections are long term. One will really sissify you as rapidly as medicine knows how. It will pump estrogen estradiol and progesterone and certain androgen suppressants into your body for the next two weeks. Then after we evaluate your body’s response to the dosage we’ll implant patches in you so the process can continue and finish without anyone giving it further thought. It will give you a girl’s way of thinking and feeling, and many characteristics of a girl’s body. You’re going to be a girl in your body, not just in your mind.”
“The other shot was a tranquilizer-sedative, the kind we give to patients undergoing minor surgical procedures. I want to keep you mellowed out for the next few days, peaceably asleep, because I want you to remember this initiation with joy, with no associated pain or soreness. When you awaken, you’ll be fitted with your pledge to me, my symbol of ownership. I’ve just arranged it with Claire, and she’ll be here shortly to help me fit it properly. For now only you will know it’s there, though you’ll never be able to forget it’s there. Until you want everyone to know, and that will be much sooner than you imagine.”
“Annie, you are a dear! You’ll know soon enough how very dear you are to me! When you wake up.” Then she added, “Poor sweetie, you never did get to lick my pussy clean. Well, it’ll be here, and you’ll have lots of opportunities.”
I remember she said all that, and that it felt increasingly good that she was saying all those things. What was her “symbol”? Maybe body piercings? Maybe a ring in my “frenum,” whatever that was? Despite all that talk about shots and changing and all, everything she said was deeply satisfying, and I felt utterly content as I rolled over onto my side on the shag rug, asleep.
The next morning I opened my eyes. No! The calendar clock on our night table said I’d been asleep for three days! So three mornings later I woke up to sunshine flooding the room.
“There you are, Annie honey!” Kate said, drawing back the last curtain. Now the light seemed nearly blinding. “I’m on call now and I’ve just been called, but I’ll be
back to see how you’re getting on in about two hours. Today is the first day of the rest of your life, honey, and believe me, that’s not a cliche. You’ll lead a very different life from now on. Just lie there and rest. Your incisions are practically healed already, and you’ve been completely depillated, and now there’s nothing much for you to do but enjoy discovering the new you.”
She came over and stood over me. Gradually I remembered. Kate. She’d found out I was into humiliation fantasies, loss of masculinity and so on, caught me reading files in Sissify.Com. And she’d taken over, she owned me. I stared up at her, still unable to find words to speak. The weekend was over? That must have been some scene, I thought! Where was I while we played it out? Then I remembered that talk about tranquilizers, and sedatives, and not feeling sore.
“Ah, I see you’re with us again. Lie still a little longer. Remember, you’re mine now, and you are not to put anything of mine at risk. I want you to discover how I own you all by yourself, and when you do I want you to just lie there and do nothing but think about what it means. You pledged yourself to me, remember.”
I lifted my arms to inspect them, and finding nothing, reached down toward my crotch.
“No, there are no tattoos, and nothing fastened down there either. And no body parts missing. And nothing buckled or embossed or inscribed or punctured or pierced. What you’re wearing is implanted, its now part of you. What I want for you. In time they will become what you want. Understood?”
She left, closing the door gently. I lay there for a moment to gather more of my wits. Then I rolled over to climb out of bed.
I saw I was wearing one of her frilly nighties with puffed out sleeves. She had a few, though mostly she wore oversized T-Shirts to bed. My own PJ’s were all in the wash? This nightgown was left over from some feminization game we’d played while I was zonked, I guessed. My arms were hairless, absolutely smooth! My legs felt that way too! Well, I hoped she’d enjoyed the game! I felt sorry it was probably over.
Still leaning on one elbow and raised up, I felt a sort of pulling on my torso, as if something were hanging from me. A fold of the nightgown? No. Flesh that had been spread out across my chest while I lay on my back was now hanging down heavily from me in the form of two heavy pouches tipped with nipples, the nipples distended and brushing against the bed. Breasts. They were breasts.
My breasts! Large ones! Two of them! I stared unbelieving and abruptly put my legs over the side of the bed and sat up. Then I just sat there! With my shoulders slumped forward they sagged, though my skin was just firm enough to support them. Through the neckline of Kate’s nightgown I could see their curves — they were soft, hanging breasts! I pulled my shoulders back, and they became ripe, rounded globes jutting away from me, their areolas and nipples like small brown teacups projecting outward. I reached to heft one. Heavy! My fingers touched one of my nipples and a delicious tingle shot through me, spreading down to my crotch. I touched the other nipple. The same! O God, it felt so good! But I was a man! These were a woman’s breasts! This wasn’t one of my fantasies! Maybe one of Kate’s, but not mine! Well yes, having breasts had been one of my fantasies, but not in reality! Kate wasn’t playing just for the weekend! Had she tried to warn me of that?
She had! These were these the badges of my servitude. Kate meant to disintegrate my manhood, to really change me into a female. So it seemed. She’d said as much, I vaguely recalled. And I’d been so eager to submit to her! Now, by daylight it didn’t seem to be as good an idea. I glanced down further, and felt momentarily reassured that my cock and balls were still there.
I picked up a breast in each hand and then dropped them. They each jounced once, then hung there. Implants. Huge. Part of me. They were there all right. But they weren’t mine. I was theirs. And they belonged to Kate. She wanted me to take care of them for her. I held each in my hands again, gently this time, and stroked their nipples again with my thumbs. The most delectable feeling rose up in my groin, deep, sultry, luscious, as erotic as if my penis were being squeezed and stroked. Yet it stayed soft. I just sat there and caressed my new self with my thumbs. It felt good!
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.
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.”
“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.
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’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 onhis 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.