Jack and Jill
by Vickie Tern
Well, our honeymoon period was the happiest of my life. Whatever Jill may have done to me, she gave me those weeks, and I will always love her for them. Not that there weren't many other happy weeks that followed, some deliriously happy. But they weren't quite the same. That first night after Marianne and Carl transformed me, and the next morning, and during the weeks that followed, I thought Jill had accepted me completely for what I was or had become, a man who played out his feminine nature as a woman, who loved playing at being a woman. And she had accepted it, in a way. That was the key to our reawakened passion in our marriage, our newfound love for each other. What I didn't realize in my delight with this new state of things, was that in any relationship like the one we'd reached, Jill was still going to determine and control things.
And Jill had decided for herself what kind of a woman I was, and what was best for me. She was determined to see that I got it whether I wanted it or not. She loved me as Jane the woman, and respected the residual man who wanted to be more of a woman, but she had only contempt for the man in me who still wanted to remain a man. She wanted no part of Jack. So she decided to overwhelm Jack by force-feeding fulfillment of my feminine desires, as she preferred to think of them. In fact, she remained as devious as ever, sharing herself freely with Jane, and hiding from Jack anything that might spook him. Some things she hid from Jane too.
Her strategy required that she sweep me along on a wave of enthusiasm she always seemed to believe I shared, playing eagerly with her new girlfriend and wife, freely exploring with me her own previously suppressed desires, exulting in any new signs that I was a woman in a new way. Or so it seemed. She was delighted that her crossdressing husband was no longer ashamed of himself, and had become her feminine companion and lover. I was in seventh heaven because I thought that now I could play out whatever my gender fantasies either way at will. But my seventh heaven was a fool's paradise—things were already out of my hands.
I didn't see it until later, but Jill was moving to eliminate my masculinity altogether, as fast as she could. She had in mind that I do womanly things with and without her until they became habitual. That included shopping, and trips to the beauty salon, and so forth. But she had in mind much more. I thought Carl had taught me all I needed to learn about being a woman sexually. But it seems my wife had decided my body should be much more female. That was what had so delighted her when I returned from my love tryst with Carl, no longer ashamed to be a transvestite, my mind apparently already gone all the way toward becoming a female. She knew that I really wanted to be a woman, not just look and feel like one at times, transexual, not merely a transvestite, whatever I thought I wanted, and she knew that transexual women, once they are women, prefer sex with men, because they are after all women, whatever they think they want (and in fact, most continue to prefer women). She knew what was best for me. I didn't.
So she never discussed these complicated matters with me, convinced that Jack the wimp in me was alive and ready to balk at anything unaccustomed. She just did it, step by step. And I went along. I was so thrilled to explore my newfound womanhood with her, and by her apparent delight in every step I took, that I didn't even notice where she was taking me. When I finally did notice, there was no returning. In fact it's only by an odd coincidence that I'm not a full scale post-op transexual woman right now, the way she was moving me along. But we'll get to that.
As she had said, I was a busy girl that day. A few days after we remarried as woman and wife, I begun to go out dressed only as a woman, by myself, or with Jill to restaurants, or to concerts where we sometimes even encountered friends who regretted that Jack was out of town so frequently. Any outing became routine, and apart from making sure I was dressed appropriately I gave going out no further thought.
But this particular day was not routine. Breakfast was a single glass of diet supplement and a cup of black coffee, and then I went back up and teased my hair into little curls the way Marianne had showed me, and dabbed on a bit of scent, and put on a touch of mascara and lipstick, and clicked my purse shut, feeling very good, quite satisfied with what I saw in the mirror. Jill wasn't. Not yet.
I realized that right away, when we walked into a downtown beauty salon and were ushered directly into a private booth, where a young woman inspected my face closely and then asked Jill if she should begin immediately. "Begin what?" I asked? Jill nodded, and the woman told me "This will feel like a series of pin pricks, dear, but it will make things much easier for you later on. Just think of each pin prick as a hair you'll never have to shave again. If we do this three times a week, in six months your skin will be just lovely." I realized that she was talking about electrolysis, and sure enough, for the next two hours the hairs on my neck were electrocuted so they could never grow back. I didn't want to break the spell brought on by our apparent mutuality of mind, so I asked Jill very mildly, when I'd been stabbed and burnt for about a half-hour, what I should do with a permanently smooth, hairless face if I should want to dress like a man again. She replied without even looking up from her magazine, "Why, the same thing you're doing now, dear, wear makeup to look whatever way you like."
I could think of no answer to that. I later found an answer: women wearing makeup look like women, while men wearing makeup look like men in makeup. But by them my face was as smooth as any woman's, and like any woman I was using face powder regularly to reduce the shine on my cheeks and nose, reaching frequently for my compact whenever I was away from the house, without even thinking about it. By then nothing could ever grow me a new beard or moustache—the follicles simply weren't there any more.
Next we stopped at a store off the main part of our largest mall, tucked in a corner, in a former natural food store. It was now an upscale Sex Shoppe. Jill had several purchases clearly in mind, and she picked them out unhesitatingly. One was a double ended dildo with a realistic, fat, veined, eight inch cock on each end, meant to be worn by a woman and designed to give reciprocal pleasure. Another was an enormous single dildo, a monster rubber prick at least ten inches long, maybe a foot, at least three inches thick, with huge balls at one end. I thought it was a joke, and wondered aloud to Jill what the rest of him must look like. But she only flashed me a quick smile and returned to scanning the shelves. Next she took down a set of butt plugs, four or five of them, each longer and thicker than the next with the biggest one thicker than even the rubber prick. Each, I noticed, was bulbous in front and had a flange in back to keep it from slipping into the large intestine and disappearing altogether. Jill was quite pleased to find these last items. Then she located a peculiar device, made of plastic tubing with what seemed to be a heavy rubber balloon at one end; she explained it was an ultimate enema, one that closed off the anus until there was no doubt the bowels were being cleared of all unwanted substances. "These are all to help you get ready darling," she said. "For what?" I asked, still a bit worried especially by that monster fake prick. "Why for the men in your life," she said, beaming reassuringly.
I thought she was joking, and replied that she was all the men I wanted, and all the women too. She looked pleased at the compliment, and didn't reply. But when we left the store she handed me the smallest of the butt plugs and a tube of jelly. "Here you are darling," she said, "I know you'll want to get started right away. I'll be in that corset shop ahead there. You can leave your tampon in place for now." And she was gone.
I barely remembered to enter the Ladies' Room, not the Gents, and then I settled down in a stall to insert the device in what was plainly going to be, for future reference, my pussy. Despite her advice I took out my tampon, greased everything carefully, and also my rear end, and then pushed, but it wouldn't press in. I pushed harder. Nothing. It was much thicker than a tampon, and that's what I was accustomed to poking into myself.. Here was a problem right at the outset, the outset of what I had no idea.
I began to let my mind drift back to how Carl had done it. I remembered that lovely fuck, his hands lifting me up and letting me back down gently, with my ass rising and falling over his prick rhythmically over and over until magically, he was in me and I was surrounding him, and I began pumping him. I set up a similar rhythm with the butt plug, and I must have eased off my sphincter muscle a little because in a minute it slipped in and stopped at the flange. I stood up, gripping the plug with my anal muscle as if it were the choicest cock in town, realized there was no way it could come out, and relaxed. I felt incredibly stretched and full, much more than with a tampon. It was very...satisfying, I realized. Before I left the ladies' room I paused to retouch my lipstick and powder my nose and cheeks, and as I walked past various stores to rejoin Jill I realized I was now a lady in another new sense too. I could see in successive reflections in store windows that with the butt plug up my rear I held my torso very straight, leaning slightly forward. Then, with each step my hips and rear end undulated exaggeratedly from side to side, and when I tried to restrain the motion my whole walk became provocatively sinuous. My wife watched my progress down the mall and into the next store with a delighted grin.
"My dear, you are the sexiest thing in the mall," she said. I made no reply, but in fact felt rather pleased myself. "Now," she said, "we're here to buy you some better breast forms and a waist cincher, and I'm here as your friend for you to consult while you do the purchasing. Tell the saleslady something about a double mastectomy and let her do the rest. Remember to use your most feminine voice."
I approached the counter, glad that I'd just powdered my nose and especially the reddened area where my beard had been electrocuted, and for the first time I tried to speak like a woman to a strange woman. "Uh, Miss, I think I need to see a mastectomy bra, um, a double mastectomy." I sounded like a flute, but the salewoman never wavered. "Yes ma'am," she replied. A half-hour later I had chosen a lovely full bra with silicone forms shaping me from my breastbone to my armpits, with a hint of a nipple visible even through my shirt, C-cups we had decided. They felt very different from the bra fillers I'd used before, much heavier, and they jiggled a little of their own weight. I liked them.
I commented to Jill in a low voice that ever since I was fourteen with my first bra, I'd disliked stuffing the cups, because a really good bra could gather up my pectoral muscles and fatty tissue, and reshape them, and thrust them forward so that my nipples became incredibly sensitive at the tips of my breasts, utterly erotic, the way they had felt this morning. But not with stuffing covering them up. I told her that the main pleasure of a bra for me was the feel of my extended nipples rubbing on blouses and suits. These breast forms feel strange and nice, I said, but they do cover my nipples so I couldn't feel them.
Jill listened attentively, and nodded. For once she sounded serious, sincere, not merely enthusiastic, when she said, "Then darling, we especially want to get to our next stop. We'll put off getting you your waist cincher, and some other things you need. We'll go right now."
Out from the mall and back to the car, with me feeling jiggly and top heavy in front and stretched out in back the whole time. Jill drove directly to a professional building a few miles away, and we entered the office of a woman doctor who called herself an Endocrinologist. As we waited for the receptionist to announce us I drew back a little worried.
"Jill, what do you have in mind? Are you thinking about hormones for me? I don't need hormones. I like who I am. That's how I want to be."
Jill smiled sweetly at me, and took my hands in both of hers, and began speaking, never letting go her grip on me, her eyes never wavering from mine. "Dear, dear, darling Jane. I know how you feel. I know just what you're feeling now. I know how you want to be. I'm a woman like you, remember. We love each other. We would do anything for each other. This is what I'm doing for you, and it's what you're doing for me. We're here so you can begin to persuade your body of what your mind already knows, that you want to be a woman, much more of a woman than you are. Isn't that so?"
"Don't be afraid darling. Your own body has always produced female hormones as well as male. You may have been washed in them in the womb, and that may be why you have these urges to let your femininity espress itself by wearing women's clothes. Remember, that's what you told me. Now this doctor will restore your hormonal balance of mind and body, so you can be more of what you want. With just a little more estrogen, you'll become a lot more shapely. You'll fit your clothes better. You'll have hips you can sway when you walk. Best of all, you'll have your own breasts. Your very own! You won't ever need to cover up that delicious feeling in your nipples. Your nipples will lead the way wherever you go! Your own body will fill a C cup, even a D cup if you want! Jane, do you want your own breasts, or do you want to go through life envying everyone else's?"
Jill paused and looked at me steadily, waiting for a reply. "I'd love to have my own breasts," I blurted out. It was true! Not everything else that went with them, of course.
"I know you do," Jill said. "I know what you want. And if you don't like any of what happens, everything is reversible. You just stop taking your pills and everything ends up the way it was. But understand me! If you don't have the courage to be what you want to be, I can't respect you. It would mean you're still too much Jack, still too afraid to be yourself to be anyone at all. Well, I won't live with Jack. I've tried it. It didn't work!"
The receptionist returned. "The doctor will see you now."
I stood up, suddenly aware that I was wearing a skirt and lipstick and mascara, that my hair was curly, my ears pierced, and my eyebrows plucked, that my chest was pushed out in front and my ass waggled when I walked, and that my pussy was stretched and filled by a butt plug, and that with all this I was worried that I might become too female. It was ridiculous. What could I say? I had to embrace the inevitable. "Jill," I said. "I want to be your girlfriend, or your lover, or your wife, or however you'll have me. You're right. It's just that all this is so new, and it's happening so quickly! Please help me!"
Jill took my face in her two hands, right there in the reception room, and leaned forward and kissed me. "Don't worry, darling" she said, looking me fondly in the eyes. I thought we must look very strange to the receptionist, two women kissing, but she just stood by the door to the inner office and waited for us.
We went in and sat down. Jill pulled a stack of papers from her portfolio and handed them to the doctor, a slim and rather pretty blonde with oversized horn rim glasses and a way of looking directly at you when she talked or you answered. She looked them over, then looked at me. "I see you're dressing full time now, Jill.. For how long have you been doing this?"
"Ever since I can remember," I said in a small voice, reminding myself to try my "lady voice" next time. Then I realized she meant how long have I been wearing women's clothes exclusively. A month, maybe more, is what I tried to say, but nothing came out.
She went on. "You've had proper counselling for the required amount of time?" Jill nodded, and I sat there. "And on careful reflection, do you really and truly want this?"
Jill turned and looked at me as I sat without speaking. Her gaze seemed to grow more severe as I struggled to say something. "I do," I blurted out into the silence. The answer sounded strangely familiar.
"All right then, dear. I have your blood workups here. They're fine." I wondered what she was talking about, and then realized Jill must have turned in some old medical records of mine in order to move things along. But I had no objection. "You know," she glanced at her papers, "You're very fortunate, Jane. Most women who take a step like this lose their spouses. Divorce is almost inevitable. But your wife is the most supportive I've ever known. In fact, because you have such a favorable domestic environment I'm going to recommend a new kind of regimen to you, one that will accomplish what you wish in perhaps half the time. It's a combination of shots, pills, and an implant, all at once. It's pretty high-powered. Your wife here will be necessary to the process, because during the first week or so you may feel moody or nauseous, until your system adjusts. It'll be a little like morning sickness, a hormone bath washing through your entire body, changing everything at once. But no matter how you feel, once started you must continue with it, the pills and the shots and periodically an implant renewal. The second week you may feel the same, but the body adjusts and reactions begin to level off. Some women begin to feel very horny at this stage, and experience a kind of farewell burst of energy from their penises, before they begin to shrink and lose their sexual function. After a month or two you'll find your erections are no longer as hard, and eventually erections disappear altogether, at least while the hormone bath treatment continues. You'll find you can still climax, but it will be dry, more like a woman's spasms in orgasm, not at all unpleasant I'm told."
She paused to look closely at how I was taking this news, saw no reaction, and continued. "Your nipples will swell up, and you'll see changes in your skin, and some of your body fat will redistribute, onto your hips and your tush I'm afraid. But we can't all look like Barbie, can we? The third month you'll feel wonderful, there's a kind of hormone-induced euphoria, and you'll also begin to see real breasts of your own growing. After that I think you'll love seeing your progress, and so will Jill here. In about six months you'll have completed your girlhood puberty, so to speak, and we'll put you on a sustaining dosage as a woman. Shall we begin?"
I felt uneasy, but Jill took my hand, and I held onto it tightly, and said nothing. "Please," she said, "lift your skirt and lower your panties, so I can inject some fairly heavy intramuscular doses. These are in a time release formula, two weeks worth of shots all at once. Jill can do them afterward if she watches me closely today. It's very simple. Bend over." I did. "A little closer, please." I pushed my rear end way out, until it felt like a whore's bottom thrust out at a customer for convenient fucking. I felt her needle enter one buttock, then pause. Then the other. "Now, dear, your belly. We'll want to place the implant in fatty tissue." She made a quick incision, placed a waxy rectangle under a fold of skin, deftly taped it up, and placed another tape on top. "There," she said, "I'll bet that scarcely hurt at all!" Then she handed Jill some bottles of pills and some packages of syringes and some prescriptions for more, and turned to me and said, "I only wish I could do more for you, Jane. But with these hormones you'll do it all for yourself. You'll love being a woman, trust me. None of us would have it any other way. But I'm sure you already know that."
"I know," I replied. I looked at Jill with an almost child-like sense of helplessness, and she smiled reassuringly at me, and I tried to smile back. I guess I'm being a good girl, I told myself to try to cheer myself up. But this was all moving very fast, and I couldn't catch up. In fact from then on I was always a little disoriented. Jill kept increasing the pace and hauling me along, faster and faster. Trying to be a good girl, I never found a quiet moment when I could decide for myself whether I wanted to be a good, or a girl. All that had been settled for me.
Jill took me back home instead of back to the mall, because I was already beginning to feel a little queasy. She tucked me into bed, and I slept though the afternoon, getting up only to use the bathroom, and to take out my butt-plug and put in a fresh tampon, then to replace the butt-plug. That evening she got into bed with me, and held my prick, and I moaned a little and hugged her, and she jacked me off into her hand. I never got hard, but I did come, and she held the handful of cum up to my face for me to lick. I kissed her, and swallowed it, and licked her palms and fingers clean, and kissed her again. Then I slept through the next day and evening. Jill gave me some pills to swallow and jacked me off again, soft, and I came again, but this time nothing came out, just a slight oozing.
But the next morning when I woke up I felt fine. Jill had already gone to her office, but I showered, and shaved my legs and changed my tampon again, and cleaned my butt plug (by now it was slipping right in, no problem), and dressed in a blouse and skirt and went for my electrolysis session wearing my new mastectomy bra. When Jill came home from the office I had dinner on the table. The hormones continued to pour into me, but I had gotten accustomed to them.
Marianne called, and I went back to her salon in the motel and had a pedicure, and she finished my nails, and retouched my hair, and called my pierced ears healed and hung a gold hoop in each. When I revisited her two weeks later so she could re-curl my hair where it was growing out, she noticed that my skin was smoother and my butt seemed rounder. I told her to stop teasing me, but I looked closely, and it was true. She saw I liked it, grinned, and amused, waggled her own rear end at me. I waggled mine back at her, still seated, and we both laughed. It was fun being one of the girls!
Soon I was taking my pills regularly, and my shots, and had graduated to the next size of butt plug, and my erections had returned. The next month or so our lovemaking was very much like those first weeks after my arrival home from the motel, my first weeks as a real woman, as Jill called them. We overwhelmed each other with our lovemaking, and neither of us seemed to get enough. My breasts became so deliciously erogenous that Jill's bare tongue on my nipple could get me to do anything she wanted, and her fingers on my both nipples could bring me to orgasm without her having to touch me anywhere else. I got incredibly horny one night, and humped her three times before my erection went down. Then when she asked me to I sucked all of the cum back out of her, along with her other juices, and tried again. For the moment, no go. She got out the double dildo and told me to lie on my back with my legs spread out high in the air, my pussy wide open to her. I lay there gleeful and eager, half out of my mind I suppose, but desperately impatient to feel that cock thrust inside me. Then she lubricated me and humped me with it, and we both came yet again, shrieking, her body falling over me and her breasts flopping in and out of my mouth while I sucked at them as best I could. She was doing it yet again when I fell asleep, from sheer exhaustion, the double dildo still plunged in my ass.
The next day I came back from giving myself my nightly enema, my vaginal douche Jill called it, to find I had graduated to the next-to-largest butt plug, and soon after to the largest, which had a vibrator in it. Once that butt plug became my anal jewelry, so to speak, Jill would smile devilishly at me after dinner, reach under my skirt, pat my fanny, switch on the vibrator, and tell me she'd join me upstairs in ten minutes, or a half-hour. Or maybe she'd say nothing at all. I'd run up and change into a pretty negligee and wait for her, or if she said nothing I'd go into the living room and try to read or watch television. But I could never concentrate with that vibrator going. After a while I would cum without anyone touching my prick, just sitting there, and then again after a while I would cum again. By this time she had me wearing a condom whenever the vibrator was on. When finally Jill joined me in bed and switched the vibrator off the condom was half full and I was half-crazed. Then she'd give it to me to drink down.
Little by little my cum became less and less plentiful, and after a few more months there was hardly enough to lubricate Jill or me to receive a dildo. After we had fucked and I was licking her out the flavor was almost all hers. One morning while I was licking and sucking at her, I felt and tasted a sudden surge of warm liquid, and as I sucked it up and swallowed it there was more, not slick but watery, and then there was even more. I slurped and swallowed it repeatedly, as fast as I could, but still some of it ran out of my mouth. I looked up at Jill from between her legs, and she looked down at me with an impish half-smile on her face, and I understood. I opened wide and pressed my upper lips against her mound and my lower lips as far down as I could reach, and sealed off the area as best I could. When she saw I was ready she peed a full stream directly into my mouth, and I tongued it into my throat as fast as I could swallow it, and it kept coming, and I nearly choked with the effort to swallow it all. But finally, I did. It was wonderful. I felt I was swallowing her most intimate, most feminine interior fluid and making it mine, making her me. When I told her that, she never again rose from our bed to urinate. No matter what the time of night or morning, all she had to do was take my head in her two hands and kiss me, then begin to move my face down her body, and I would know. I would press my head into her crotch, and eagerly drink everything she could squeeze out of herself. "My dearest little toilet," she called me when she wanted to reward me. I loved it.
Some of our nights or mornings together were reserved for pussy training, as Jill called it. First I would go to the bathroom and clear out my lower colon with the super enema, inserting the whole contraption, sealing my opening by blowing air into the balloon-like bladder, then forcing a quart or more of water into me, to be held until Jill judged the time sufficient and told me I could release it. I would then let the air out of the anal seal, and remove the enema, and my lower intestine would gush out everything, and I was ready for her. Plentiful jelly was supplied, and Jill then strapped the double-dildo into her cunt and slid the other side into mine, then rode my ass until the pressure in her pussy got overwhelming and she came, or sometimes the both of us came together. It was a little like the vibrating butt plug, because strange feelings were stimulated inside me, not in my penis, and I was beginning to enjoy them more and more. I even began to prefer them as months went by and my erections got increasingly unreliable.
Some time into the fourth month of my hormone bath Jill brought out a new butt plug, the biggest I had ever seen, the size of a fist at its widest diameter and the thickness of a wrist at its base where it narrowed down. A few weeks later I was easily slipping it in and out of my pussy. Then one night Jill brought out that monstrous rubber prick and told me to get on all fours, my rear end high in the air. I did. She worked it into me, and I took the thing up my ass with tears in my eyes and an unspeakable joy in my heart. My butt was stretched utterly full, bursting, and I thrust back against that huge dildo in spasms, bucking like an animal in heat and making throaty, high pitched, whining noises. The following day was the first she fist-fucked me. This felt utterly glorious, and rendered me helpless. Jill obviously loved seeing and feeling me reduced to a slab of whimpering meat wrapped around her arm, because for the next few months she did it frequently, almost on whim. By then my sphincter wouldn't seal up my anus any more, and I wore tampons and panty-liners all of the time. I was "pussy trained."
Jill gave away Jack's clothes soon after my hormone treatments began. "Oh Jane," she said to me while we were lying together one morning, "I hate your pants. And you look so cute in a skirt. Let's give away all of your boy things, even your girly boy things. I want to feel you're always open to me." So we did, cute shorts, harem pants, slacks, even pantyhose. My panties became the only barrier between my asshole and her whims whenever she had a mind to shove something into me. But I had to wear them. Between the enemas and the size of my opening, I trickled whenever I was exposed. Even so, she wanted access to me whenever she was home, so when I heard her car in the driveway, I took out my tampons and butt plug, inserted a pantyliner in my crotch, and waited to see what she might do. It was peculiar, sitting with my legs crossed and waiting for her to enter the house, feeling both ladylike and sluttish. wondering what the evening had in store.
What happened during those six months was, knowing I was still somehow a man, I became a woman. Not much during the first few weeks, of course, when I was getting accustomed to that massive dose of hormones. I did lose the ten pounds Jill had prescribed, and my dress size went down to a twelve, and gradually I filled out my wardrobe, sometimes with Jill's help and sometimes by myself. I returned to the Doctor for checkups or additional shots in the butt, and my ass and my hips filled out, and my waist narrowed, and my breasts grew until by the fifth month I no longer needed breastforms and they went into a bottom drawer. The electrolysis was completed, and my face looked like a baby girl's. Marianne changed my hair style and piled curls especially on the crown and back of my head and down one side, and she and Jill and I all agreed I looked cute as could be. I adored it.
I fucked Jill as best I could while I could, but toward the end there were no more erections, and that was that. I tried to make it up to her by avid sucking on her pussy, and I was eager to become her toilet on call. But now it was the double dildo that linked us together. One night I discovered that Jill could also use that monster rubber penis, not just me. I was slurping and fingering her when she asked me to get it and lubricate it. I took the tube of jelly, and she said, "No, with your mouth." So I did. It was like old times, licking up a vein on the underside, and trying to suck the head into my mouth. It wasn't Carl, and I had no feeling for it, but it was huge! Jill had me lie on my back with the thing poking up between my legs just below my crotch, where my own prick just lay there like a deflated balloon. Then she mounted me and positioned it under her, and we made love the way Carl had made love to me the first time, only this time I got to watch her climb on top of me while I was on my back.
I played with her titties, and kissed them, and took her waist in both hands as Carl had taken mine, and started her rhythmic movement up and down. Once Jill could feel the tip pressing against her pussy, she lifted and lowered herself over and over, and gradually sank down onto it. When she finally had most of it inside her, she settled between my legs, and then with the full length shoved into her it seems she just sat there, unable to move. I realized she was in a kind of fugue, a pre-orgasmic suspension in time, maybe not even conscious. So I took the flange in both hands and started to work it in and out of her. She went up like a skyrocket, writhing and arching her back and stretching out her arms to the ceiling, and screaming, over and over until gradually she subsided. When I took that huge thing out of her it was like assisting at a birth. She was covered with sweat, and exhausted. She smiled weakly at me in gratitude, then fell sound asleep. But six months into my hormone treatment that rubber telephone pole had become our common lover. She would use it on me, and then I'd use it on her, and we'd both enjoy paroxysms of pleasure from it.
Those six months she worked days at her law practice and nights and mornings with me, while my body was transforming before her eyes. One morning she watched me putting a bra on by leaning way forward, so my breasts could fall into the cups and be contained by them before I straightened up and pulled the straps into position.
"You're a real woman, Jane," she said with surprise in her voice.
"What did you expect?" I asked her as I adjusted my bra and reached for a slip. "I've been drowning in hormones for a long time now, as if there were no tomorrow. Is there a tomorrow?" What I meant was, when would I be woman enough for her to put me on a smaller sustaining dose, so I could begin to see if any of my old male reflexes had survived her shock treatment. I was especially interested in whether I could get an erection again.
"Yes, dear. There is a tomorrow. You look just lovely." She said it half-abstractedly, as if her mind had turned somewhere else and was thinking through something different. For five minutes she stood by her dresser staring into the middle distance, while I slipped into my dress, and stockings and garterbelt, and pumps, and combed out my curls and touched up my face. She didn't seem to notice. "Jill, are you there?" I asked, waving my hand in front of her face. "I'm going out now to the hairdresser. You're going to be late for work."
She looked up at me and beamed broadly, suddenly back in time present. "The hairdresser, wonderful!" she said. "You make yourself pretty for me, darling, and wait up for me. But don't wait dinner. I'm going to be a little late tonight."
I was sitting up in bed reading when I heard her come in, wearing my prettiest satin nightgown. I loved the way the tips of my filled out breasts and enlarged nipples rubbed against the material—my nipples were by now in a permanent state of erection, it seemed, even when my penis had forgotten how. It was nearly midnight. I sat watching the door to our bedroom and listened while she came up the stairs slowly, as if tired. The poor dear. When she came into the bedroom she looked tired, too, but there was something strange. She also looked a bit flushed, even excited, and she was still carrying her purse instead of leaving it on the hall table downstairs. She looked at me, and smiled, and leaned back against the door, and her smile grew wider, a kind of cat about to eat the canary smile..
"What is it, Jill?" I asked as I set my book aside?
"I have something for you," she said.
"Really, what?" I asked.
"Wait till I get in bed with you, and turn out the light. It's a kind of surprise."
"Oh?" I made room for her while she undressed quickly, and slid in next to me naked, without stopping to put on a nightie. She left her purse on the night table, right at hand.
"Now lie back and close your eyes," she said with a delicious smile. And she leaned over to kiss me, so very sweetly and softly that I closed my eyes without thinking, and then left them that way. "Do you know what you haven't tasted lately?" she asked. I thought it through quickly. Not her cunt, which I still sucked passionately whenever she needed to pee, and which I always sucked as the main way we made love now that my prick could no longer perform. "Open your mouth." I did, eyes still shut, face turned up on the pillow, aware that I had put lipstick on just before getting into bed so I'd be pretty for her, hoping she thought I was pretty as she leaned over me. "This!" she said as if she were entrancing me in a magic spell.
I felt a thick, warm, viscous substance drip onto my lower lip, and I reached to taste it with the tip of my tongue. It was a little sweet and a little salty, like Gatorade, and at first I didn't recognize it. Then on an exhale I caught the faintest hint of laundry bleach, and suddenly I knew. My eyes flew open. I saw in the gloom that Jill was suspending a condom upside down over my mouth, and at that moment about a teaspoon of pale cloudy substance a little like mucous glopped out of it and into my mouth and onto my lips.
"Swallow it, dear," she said. I had no choice. I swallowed, feeling bewildered, and annoyed, and sensing a spark of anger surging somewhere underneath. What was she doing? Was this a practical joke? Again she leaned over and kissed me, with infinite sweetness, and again her lips lingered. I waited for her to break off so I could cry out "Whose is that?! Where did you get it?!" But her lips stayed grazing mine, and she began murmering to me.
"My dearest, dearest Jane, tonight we are celebrating together the start of another stage in your transformation. You are real woman. I saw that when you were putting on your bra this morning, so gracefully, so naturally, with your pretty tits held up in the cups of your pretty brassiere. I am so proud of you! You look so feminine now, and I know that you are making yourself as pretty as you can for me, and I love you for it. You are so much a woman now that I can't possibly think of you as my husband. You aren't anyone's husband any more. And I'm not your wife. The only part of your masculinity that remains doesn't matter. It doesn't get erections, and it doesn't make cum. When you were my husband you made love to me with your prick like a man, and when you were my wife you drank up your own cum afterward like a woman. But no more. We're past that. Now you are my dearest girlfriend. We love each other. We share everything with each other. Don't we?"
She paused as if waiting for an answer. I started to murmer back at her "Yes, but...," but all I could get out was the first word, and she began again.
"Yes, everything. You are almost everything a woman should be. In fact your hormone bath treatment can end any day now, whenever you wish. It's now up to you. It could have ended with your last checkup, you remember, when you went from a B cup to a C cup? But then I still wasn't sure you were the woman you should be, so I told the doctor you needed more time to find and use your new desires, to feel how strong they are, before she put you on a sustaining dosage. That's what we are going to do now, Jane my love."
I was puzzled, but I did have a dark suspicion. "What are we going to do now, Jill dear?" I asked as gently as I could.
"Why my darling, we are going to explore the marvelous world of men. You and I together. Each night we are going to make love to men, each of us. We've already begun. What we've just shared is a man's sperm. Doesn't it taste marvelous? As a woman I know you love it. You'll want to put it inside you every way you can. The urge can be overwhelming, and I want you to let it grow into a powerful force. To yield to it, and yet remain a lady, that is the true test of your womanliness. I'm going to help you, my love. I'm going to share this wonderful voyage with you."
I began to feel frightened. "But Jill, I don't want men. I want you! That's why I've done all these things all of these months. That's why I've let you do these things to me."
"Darling," Jill resumed, and she began to caress one of my nipples with her finger, and I began to melt into the bed. She kept talking. "Everything I've done is what you wanted me to do. When I married you I thought I married a man, but you were really a woman without the courage to be yourself, only a man who liked to sneak around in women's clothing. Well, I changed all that, didn't I dear? And Carl." She started to suckle on one of my tits, and I went into ecstasy. "Carl found a humiliated and intimidated transvestite, and in one night he changed her into a proud and passionate woman. Do you remember how you felt when you arrived home? You were completely feminine in mind and spirit. Now you're also a woman in body, very nearly. It's time for you to enjoy the most sublime experiences a woman can have. Our marriage is over now, Jane. It has done its work. Now we're going to make love to men. Many men. You say you want me. You have me. And this is what I want you to do for me! And for yourself. You will, won't you darling!"
And with this she fell to kissing and tongueing and licking my nipples, first one and then the other, until I nearly fainted. "Oh yes!" I cried out impulsively as her tongue lifted me toward heaven. "Yes! Yes!" And then and there I came, in a glorious orgasm, all inside of me somewhere, my shrunken penis and balls taking no part but the mound behind them tensing into excruciating anguish and then pulsing out as pure joy in wave after wave of magnificent feeling, washing through every part of me. "Ooohhhh," I cried out, "Ooooohh, Ahhhh, Jilllll, Ooohh, Yesss!"
"I thought so," Jill said, lifting her head. "Then we won't ever discuss this again. Don't worry, sweetheart, I'll make all of the arrangements. Here, love, enjoy this for now. Suck on it, until we find you something nicer to suck."
And she tucked the used condom into my mouth. Whose condom? Whose cum was I sucking? How did Jill come by this condom filled with some man's spunk? Where was she earlier tonight? Jill, my wife? My ex-wife, now my best girlfriend? My best girl friend, who brought home to share with me the taste of some fuck or suck she'd had earlier this evening. Now she wanted us to double date, so I could fuck or suck for myself? Did she see this time coming? Is this why she was feeding me my own cum all those weeks, when I still had any? Is this why she was stretching my asshole, until it could take any prick as easily as if it were a cunt, and would feel like a cunt to any prick? My own prick was now useless to her, and to myself as well. There was nothing I could say. My mouth was full of thin latex coated with globs of someone else's jism. I rolled it over and over on my tongue, extracting and tasting and swallowing every last drop.
Jack and Jill
I must say about Jill, it didn't take her long to put me through her crash program in "womanhood." What she had in mind for me was that I develop the habits and tastes and reflexes of a twenty dollar whore, to make me into a promiscuous slut as quickly as possible.
She did it in a few quick thrusts, each one justified with her usual enthusiasm and backed by her iron will, and I was so bewildered and trusting I went along with each, and did whatever she asked. It never occurred to me that her notion of womanhood for me could be called peculiarly narrow, that she herself didn't really subscribe to it, nor any woman we had ever known. It may be she wanted to drown out the last of my masculinity, any residual shame I still felt that I was a woman, by making me behave shamelessly, by getting Jane to fuck and suck anything in pants so relentlessly that Jack could find no place to hide. It may be that she was simply being vindictive, degrading me for her own amusement. But she could certainly be persuasive! She had already pushed me further than I meant ever to go, especially with the hormone bath that had turned me—not altogether unwillingly—into a girl with a prick. I was in unknown territory. I had no choice but to trust that she knew better than I did what I needed to do next. She was never in doubt.
For a few weeks she called me nearly every night to warn me she'd be home late from the office, and that I should be prepared to meet her at the front door. I did as she asked. Night after night, her car arrived, her footsteps clicked up the walk, her key opened the door, she rushed past me, and she slouched down on the couch with her knees spread apart, and said "Jane, you slut, clean me, suck me out!"
And that first night and all those following, that's what I did. It was obvious that just before coming home she was finding some way to get herself laid over and over. Her panties were usually in her purse. When I knelt and lifted her skirt, her pussy hairs were always matted with somthing sticky, and when I began to lick her slit, gobs of semen would squeeze or trickle out. She was filled with cum, overflowing with it. It was often the same person, but often different men—after three or four days nursing all that cum from her cunt I could taste the difference. A few times she came home with a three or four man orgy in her, different flavors overflowing from different depths of her cunt, and I was half the night cleaning her out. She always assumed that I was addicted to the stuff, because real women were, and that she couldn't supply it and I couldn't slurp it fast enough. So I acted as if I were. This doubled her pleasures, I assumed, first when she was getting herself laid somewhere, and then at home, while I was lapping and licking her out, and she'd come repeatedly on my mouth. I wanted to please her, and I still couldn't raise a decent erection for her, so I tried to be grateful that she was sharing her men with me, and that our oral sex with me was passionate, at least on my part.
Then we sort of double dated for a while. That is, we went together to a bar where, she said, men and women were usually available to each other. She instructed me to dress for it. The first night I put on a brief silver mini sheath with spaghetti straps and a hemline just below the curve of my ass, and crotchless panties. The panties were always a risk, because I douched or did an enema just before we went out, so with my loose asshole I was often damp down below. When I mentioned this to Jill she was delighted, and added a little bath oil to my douche fluids, so I would seem so hot I was already lubricating down my leg. For these outings four or five inch heels and net stockings were routine, and I slathered on the eye makeup and lipstick. When I saw myself in the mirror I would have given myself a hard on if I'd been able to have one. The first night Jill settled into a booth with a blond man named Sam she seemed to know from somewhere else. They sometimes disappeared somewhere, and then reappeared with Jill's hair mussed a bit, and disappeared again, then just seemed to sit quietly together and talk. I wondered if Sam's was some of the cum I had eaten out of her. I sat at the bar, watched this man with my wife (because that's how I still thought of her even though she'd decided we were now only girlfriends), and turned away a few men who offered me drinks. Jill motioned me over.
"Is something wrong, honey?" she asked.
"I don't know, I said. Oh, Jill, I think I'm a little bit jealous. We were married for so long. And now Sam has you, and I..."
"And you're a woman who can have any man in this place, Jane. And that's what you need! To be well-fucked! Then you won't think about silly things any more!"
She instructed me to sit at the bar and agree to do anything anyone proposed, so I could sample all the variations there were and gradually get to know what I liked. I would explain to them that my pussy was unavailable because of the time of month, but that I would swallow every drop of their sperm because I could never drink enough of it, and that I loved taking it in the ass (as indeed I did by then, if the invader was Jill's dildos or Jill's fist and wrist).
So I sat there, and in the next two hours I was served five drinks and finished three of them, and I gave three blow jobs—one of them right there at the bar, by the wall, partly covered by a man's jacket. And I was butt fucked four times, once rather sweetly by a very nice man who clasped my tits and hugged me to him and gently rolled his penis round and round in my buttocks, and kissed by neck. That was lovely. Another time by the same man twice, who didn't even slow down after his first climax, but rode my ass on to a second. I went home leaking all over my beautiful dress, and Jill reminded me to take condoms and tampons to the bar when we returned the next night, and a butt plug to close the door when I was ready to stand up and go home. So I did, and I spent most of that next evening groping and sucking and grinding my ass into any number of men. I really lost count. I set up in a booth in a back room, and Jill and Sam looked in on me sometimes, and Jill smiled encouragingly whenever I came up for air and headed back to the bar to pick up another stud, or she winked at me as if I were having a good time. I didn't want to disappoint her, so I winked back. But I felt a little cheap.
By the second week word had gotten around that there was this girl in this bar who gave head and cunt as if there were no tomorrow, and there was practically a line out the door of men trying to get in to buy me a drink. Jill mostly just sat there, though sometimes she took Sam home with her afterward and they disappeared into what became again our former bedroom. The fourth week Jill and Sam really did set me up as a whore. They rented a nearby motel room, and signed up all of my regular bar customers on the half-hour, and they told their friends. I lay on the bed all night with my butt up in the air getting reamed, and my breasts getting groped, or my clients sat on the bed while I knelt and cocksucked whatever came into my mouth. Those weeks I saw a lot of pricks, all shapes and sizes and flavors and fittings, and a lot of odd behavior in the men attached to them too. But it all became routine. My mind wandered. Fucking and sucking from dusk to dawn seven days a week, after a few weeks there are no surprises left.
In fact I was swallowing so much semen each night that I began to gain weight, and some of my clothes no longer fit me properly. This amused Jill, who joked that this was a funny way to be look pregnant, but for me it was serious. I loved my size twelve dresses, even though they required that I diet all the time. "Jill," I finally asked her after the sixth week on my back or my knees servicing fifteen or twenty pricks each night, "Am I a woman yet? This isn't me. I'm a one-woman woman. Or if you insist on it I'm a one man woman. But not this. Can't I at least develop a relationship with some one person, the kind you have with Sam? I loved being with Carl. I'm beginning to remember even Tom fondly. Can't I just be a woman with a boyfriend?" I started to cry. "I want to be loved!" And then I broke down and couldn't stop.
Jill took me in her arms and held me close, for the first time in a long time it seemed. "Darling, darling Jane," she cried out. "A boyfriend! Yes, we will certainly look for one. But you have had to learn for yourself what the past weeks have taught you. Now you know that physical relationships are only just that, that your feelings and desires must be involved or all the sex in the world is meaningless. Isn't it? A woman needs romance, a companion for her heart, and she can give her body most lovingly only to the man who has already captured her heart. We'll find you such a man, dear!" It sounded specious to me, Jill moralizing about true love after she had converted me into a hooker, but I didn't care. I needed somebody to love me.
The next night Jill invited me on a threesome with her friend Sam, dinner and a movie. I dressed as carefully as if Sam were my own date, and I must say our conversation sparkled all through dinner. I had finally learned to control my flute-like femme voice, and to gesture in a flip, loose wristed feminine way, and I was happy and animated and felt marvelous. I must also confess, I liked Sam, and wanted him to like me in case he and Jill should ever fall out. I flirted shamelessly, and it felt wonderful.
From then on I went out only on proper dates. Sometimes I dated friends of Sam and sometimes men I met shopping or doing errands. If we came to sex, and it usually did, it was because we both wanted to, though I was always flying the rag as far as they were concerned, and needed to be taken from behind or with my legs on their shoulders. These men were always far nicer than the ones in the bar or in the motel. I would blow them gently, and they were considerate of my feelings, and were amused by things I said, or thought me cute, and some of them felt protective of me, and some I just loved to fold in my arms while they suckled sweetly on me like little babies.
I told Jill how I felt about them, how I appreciated being treated decently, not just used, and how my heart swelled up when I thought about one or another sometimes, how pleased I felt when I saw them at the door. Jill nodded, and hugged me, and we had another good cry. It was true, she said, men could be so awful but they could also be so marvelous. They felt so beautiful. This may be what Jill wanted me to know about men, I thought. Now I could look forward to meeting more of them. And I did, quite a few, though I never got really serious with any the way Jill seemed to be with Sam.
When I brought men home we used my room, and when Sam stayed over with Jill they used the room we'd formerly shared together when we were married. As the memory of that marriage faded out of our relationship we became more and more like sisters, and we looked more and more for privacy from each other. Sometimes we could hear each other making love, but not usually. We respected each other by closing our doors. One morning Jill forgot, or Sam forgot after visiting the bathroom. And this brought on another radical turn in my life.
We had double dated, me with a current boy friend, nothing serious, though he had the knack of kissing my body as if he were worshipping me, and I felt exalted whenever we were together. We had spent the night as couples do, and the next morning I let him out the front door with a tender kiss and a promise to call soon.
On my way back to my room to wash up, I passed my former bedroom with Jill. The door was ajar, and I could hear quiet, serious murmering just inside. I paused. Jill and Sam were talking, Their voices sounded strange. Not strange, exactly, but relaxed, intimate, serious yet casual. I realized that Jill had not spoken to me like that since that moment in our marriage when she first found out I crossdressed, and we had ceased to be a loving couple. With Sam Jill seemed natural, easy, friendly, companionable. Everything she had been saying to me sounded made up, overly enthusiastic, or forced by comparison.
"Then when will you tell him?" Sam's voice asked.
"Her." Jill replied. "Her. Her legal change of name and sex just went through last week. I haven't told her that yet either. She needs to sign the final papers. Then I'll tell her."
"Do you think she'll make any trouble? She's dumb, but she's not stupid."
"She hasn't so far. But I'm not worried. She gave me her power of attorney long ago. And she gave me her word she'd do anything I asked her to do, unconditionally. Remember, when all this started, right after we first met and made love? I told you I had an effeminate husband back home who'd slept with his secretary, and that he was paralyzed with guilt, and that I'd put him into the deep freeze until I could decide what I wanted to do with him? I was ready to divorce him then and marry you, Sam, but you agreed that first we should thaw him out and have some fun with him? He agreed then to follow every order I gave him, and he's been true to his word. Or lately, she's been true to hers. At every step we've had no problem talking her into going along with whatever I've had in mind." Jill paused, then went on in a reminiscent frame of mind. "Sucking all that semen out of me for weeks, just to get her used to the taste so she wouldn't balk when we really put her to work! I'll never figure out where you collected it all each day."
"I've got friends who owed me favors," Sam said, "And jerking off into a bottle seemed to them an easy enough way for them to pay me off. Anyhow, a lot of that stuff was mine, remember, and I didn't need a gravy baster to put it where your so-called husband found it."
"No, you didn't," Jill said affectionately. "Anyhow, there she was, already agreeing to anything, even begging me to piss on her. So how could I not? Then she actually let us turn her into a human scumbag! Whoring for weeks or months! I told you she would! You still haven't paid me the ten dollars you owe me for that one. But she did it! She really is still the old Jack with tits, isn't she, still the wimp I can talk into doing anything! And to think I once married him!"
Some of Jill's professional enthusiasm now entered her tone of voice. "What say, Sam, will you take on another ten dollars that I can get her to cut her balls off? I'm sure I can do it. I know I can! Twenty dollars if I get her to beg me to let her do it, OK? I'll make that my parting gift to her, that she herself pleads with me to cut off all chance of ever becoming a man again. Not that Jack ever was much of a man. He doesn't know it, but even now his impotence is still reversible. Partially reversible, anyhow."
"Well look, Jill," Sam said, his voice persuasive in its turn. "OK, you married an asshole, and you've fucked him up the ass, which is what assholes deserve. I even fucked him up the ass, one of those nights in the motel, and he never even bothered to notice! Stupid shit! OK. We've both had lots of fun by now. We've turned his mouth and ass into garbage cans. He waddles around all day in high heels. He's a man with bags hanging off his chest who can't get it up any more. You could probably get him to hang by his thumbs all day in a closet, waiting for you to come home. I don't doubt it. He's so fucked up now he's too easy! Quit playing with him. Forget about castration. Get him to sign the papers, and we'll be done with him. He's not a bad guy, for a queer! He does give good head."
"You ... animal! How would you know?" Jill's voice turned almost musical, and I realized she was talking to Sam with deep affection. I felt jealous, and deeply sad, all at once.
"Hey!" Sam said laughing. It sounded as if she was groping him somewhere ticklish. "No, seriously, can you tell him soon that you're through with him? I want us to be married! I really do. It's been how long now, over a year you've been putting me off just so you could play these mindfucking control games with your husband? At least by now he should be an ex-husband! So he wasn't the man you thought you married? So what? I am! There's nothing pansy about me, and you know it! Dump him and let's get our lives in gear.
"When the papers are finalized, love. Only another few days. When Jack becomes Jane on paper, our marriage is annulled. A legal woman can't be married to a legal woman in this State. But there's been lots to do. I've only just finished transferring the balance of his property to my name, including that huge inheritance from his uncle that he doesn't even know about. The dumb prick!"
"He isn't a prick any more, Jill. He's hardly even got one, thanks to you." Sam started to snicker, amused by his recollections. "You've had your fun. Remember when he limped and flounced out of his car with his sore ass the morning after he first got fucked, and you praised his grand conversion to womanhood, and you practically told him what you were going to do to reduce him to whimpering jelly, and he bought it all?" Jill began to chuckle at this. "And remember the way you described it, his sorrowful sad eyes big as dinnerplates when you got him to stick his butt way out in the air for the doctor, to get it so loaded with hormones that he couldn't see straight for days, and still can't think straight? That mean-tempered lawyer in you really found someone you could fuck over more thoroughly than anyone anywhere has ever been fucked over before, and you couldn't resist! Your own husband! And he collaborated with you at every turn! Stupid shit!" Now the two of them sounded like an old married couple sharing old jokes.
There was a pause. Then Sam asked, "After he signs those papers, do you mean to kick him into the streets to sell his ass for rent money?"
"No, I'm not that mean," Jill answered Sam in a teasing tone. "I'll leave him a little something for his lipsticks and panties and tampons and things, his little necessities." She giggled. "He's a grown girl. He'll be grateful, you watch. Are you sure you don't want to bet twenty I can't get him to plead with me to cut off his balls in token of our undying love? On his knees? I'll make it tougher. I'll throw in his prick too. And I'll make the appointment with the surgeon right now, cut it all off one week from today, and I guarantee you he'll go like a lamb to the slaughter with tears of gratitude pouring out of his eyes and ruining his mascara. A bet?" Sam stayed silent.
She giggled some more, and then turned serious again. "There's no problem with him earning some kind of a living. All he wants is to keep himself in pantyhose. He can always go back to computing I suppose. Of course by now he might prefer to earn his living selling blow jobs. Imagine, swallowing so much sperm he was gaining weight! Can you believe it even now? Maybe we should set him up in a one-girl call-girl business, and collect a management fee for our trouble. I'm sure I could talk him into that. But how would you know that he gives good head?" Her voice became muffled, and the bedsprings squeaked a little, and Sam gave a small groan, and didn't answer.
I stepped away as quietly as I could, and went back downstairs to the kitchen. I was still in my pink lace wraparound, and as I reached for the coffee pot it fell open, and my breasts were exposed. They sagged a little, but they were pert enough. I kind of liked the way they stuck out. They weren't bags at all! They were mine! I was kind of glad to have them. I glanced at my reflection in the mirror by the back door, and I liked what I saw. Even in the morning, fresh out of bed, I wasn't too bad looking—in fact, I thought, I'm sort of cute. I loved the way Marianne was doing my hair these days. I repressed an urge to go back upstairs and fix my makeup before anyone else came down. Instead I sat down with a cup of coffee, and began to think. A half hour later the coffee was cold, and I still hadn't drunk any of it.
Jill and Sam came downstairs. Jill winked at me in her conspiratorial way while Sam was occupied splitting an English Muffin, and I remembered that as far as she was concerned, the two of us were now girlfriends who each took pleasure in the hunks of meat we brought home. I smiled at her. She smiled back. Then I smiled at Sam. "Sam," I said to him. He looked up. "Last night was just wonderful. A marvellous surprise! We should do it again."
Sam looked a little startled and bewildered, and glanced at Jill quickly before turning back to me. I had wanted to shake him up a little, and I did. "I guess we could arrange another double date, Jane," he said, recovering as best he could. He glanced at Jill again.
"Just what I'd like! How's this Friday night, sixish, for drinks and things before we go out for dinner?"
"Fine," Sam said. "OK with you, Jill? Can you take care of it? Can you have everything ready for Jane by then?" I understood what he was really asking her, and I wondered how many clues like this I had been ignoring. Maybe hundreds.
"Six this Friday is good," Jill said. "I'll be ready. Then Saturday we can do what we've been planning the way we've planned it."
They didn't mind talking about running off together under my very nose! "Oh," I said, "Just one more thing. Bring a friend. Maybe someone who owes you a favor?"
"Sure," Sam said, a little uncertain. He looked at Jill again.
Jill looked back steadily. "Didn't you tell me you about a guy who was a professional football player until a few years ago, a big bruiser you just took into your firm?" Jill asked. "Why don't you ask him?" I heard her. She was proposing that Sam find a big-prick stud to stretch out my asshole one last time, so I'd sign the papers and the two of them could get their future under way.
Sam relaxed. "Good idea," he said. "He hardly knows anyone in this town. You'll like him, Jane."
"Wonderful!" I said. "Then it's settled. I'll see you then, Sam. I've got to go fix my hair." And I left them to their breakfast.
That Friday Jill came home from her office a little late. I was entertaining Sam and his friend in the living room. I had just served them drinks, and was telling them a bawdy story when she came in the back way and called out "Jane, are you there?"
"Yes, honey," I called back. "The boys are here too."
"Hi, guys," she shouted. "I'll be with you in a minute. I'm all ready for our big night—I changed at the office. Jane, can we talk for just a second?"
I walked into the kitchen, and Jill stared at me. I was wearing a bright red dress with a princess neckline cut so low my cleavage was fully visible, and my upper breast curves hung out practically to the nipples. The dress was one I had bought when I was still developing my bust and my fanny, and it was a little tight on me. The overall effect was of a girl about to bust her buttons, or of a well-packed sausage spilling over at each end. Just the right amount of sexy vulgarity. And it had done just what I wanted it to do. Sam had taken one look and turned away, a little ashamed that he'd brought a business associate over to date such a broad. But his associate Art had bugged out his eyes and then couldn't take them off me. He still couldn't speak straight. He was well set up for his role in the evenings proceedings. He had one thing only on his mind.
"Jane, are you sure about that dress?"
"I think it's fine, dear. What did you want to tell me?"
"Oh, nothing important," she said. She gestured at a half-dozen papers she had spread out on the kitchen table so that mainly, only their signature lines were visible. "Some things you still need to sign, leftover from Jack's business. Let's get them out of the way, and then have some fun with our fellas." She handed me a pen.
"I'll sign them, Jill. Don't worry. I've given it a lot of thought. You've done so much for me, and I am grateful to you. I love you, I guess, still, despite everything. We were once married, and I suppose legally we still are. For now." Jill looked up at me sharply. "But first you have to do something for me."
Jill was bewildered, but reached to regain the initiative. "What are you talking about? Of course we love each other. What is it you want me to do?"
"Sam's friend in there is named Art, and he's about 300 pounds of solid muscle and gristle. From the bulge in his pants—that's why I wore this dress, honey—about 100 pounds of him is hanging between his knees."
Jill interrupted with routine enthusiasm. "Oh, how wonderful for you darling! He's ...."
"No, Jill," I interrupted. "Just listen. For once, just listen. I'll sign those papers. I'll sign them the moment I see something."
"See what?" I realized that in all these years, I had never negotiated a deal with Jill, bargained so that each of us could get something we wanted. I had proposed things for the two of us, and she had accepted or rejected them. But I had never set conditions. She sensed there was something new happening here.
"What I want to see is your Sam going down on Art and blowing him until the cum drips out of the corners of his mouth, and out of his nose, and maybe out of his eyeballs and ears. And I want to see Art drilling his prick into Sam's ass. I want Sam to be wearing a bra when it happens. I want it to happen tonight, now, before we go out to dinner. I want to see you arrange for this to happen, and I want to know that's what you're doing right from the beginning. You are one of the world's great manipulators of people. I want to admire your technique."
Jill just looked at me, taking my measure. I had her full attention. I went on. "I was no match for you. I'm a wimp, and besides, I wanted to please you even when you were walking all over me. I was a nice guy. Now I'm a nice girl. I'm still easy for you. But now I want to see you humiliate someone else. Someone you admire and respect. I want to watch your future husband become a darling little cocksucker just like me. I'm sure you can arrange it. I'm sure he'll do anything for you, just as I did. Then I'll sign those papers."
Jill looked at me steadily. "Jane," she said, "There's more to you than I've credited you. How long have you known?"
"Not long. A few days. I should have known from the moment you first started working on me, but I was so eager for you to let me dress up I guess I didn't want to know. Don't misunderstand me. I don't resent what you've done to me just because you knew you could. If I hadn't wanted it too, I wouldn't have done it. I am grateful. What I'll do from here on in I don't know, but that's not your problem. Your problem is to get Sam into a bra and make him swallow Art's meat at both ends, and to get Art willing to do it. Then you'll get what you want. And I'll be satisfied. And we'll each get on with our lives."
Jane continued to look at me, her gaze unwavering. She scarcely paused for thought, and then said, "All right then, Jane dear. I understand. You want your little pound of flesh. Sam is all man, and you don't want me to marry a man who's all man. I got you to suck cock and take it up the ass whenever I snapped my fingers, so now you want Sam to do it, and every night Sam and I are together you want me to know he's done it. All right. I'll fix it. Maybe it'll take a half-hour. Not much more. I'm hungry. I want to go to dinner. Go in and refresh their drinks. Pour a lot into Art, if he's as big as you say. And send Sam in here. You don't mind if Sam knows about your little scheme, do you?"
"Oh no! It'll be more fun for me if Sam knows what knowing you is costing him. But I don't think Art should know. I want to watch you twist him around the way you did me. Besides, he looks pretty straight to me. If he thought Sam wanted to go down on him maybe he'd wipe the floor with him. Maybe he's never poked anyone's asshole. But he has to know afterward that it was Sam."
"Don't worry, I'll take care of it," Jill said. "No problem, girlie. Go wave your tits in Art's face and give him something to drink, dear darling Jane." She said "Jane" as if she were swinging a sledge-hammer at me. "Shake that shapely ass at him. Do you still keep a tampon wedged in there somewhere, princess? Does your fuckhole still stretch big enough to satisfy an elephant? Send in Sam."
Finally, I had gotten to her! I loved it!
Jack and Jill
Five minutes later I had poured Art a full tumbler of whiskey and he had emptied it down, by the simple device of telling him there was a naked lady to be seen in the bottom of the glass when he had emptied it. He chugalugged, and I stood in front of him with my breasts pulled out of their flimsy bra, so he could see me through the clear glass bottom of the tumbler. We both laughed uproariously at this little joke, and Art reached for me. "Later, hon, " I said. "After we eat," and I tucked myself back where I belonged. Art was already sweating.
Jill and Sam came back out from the kitchen, and I was delighted to see that Sam was visibly disturbed. He seemed clubbed. His shirt was a little untucked, as if he'd hastily pushed it back into his pants. So he'd agreed, and his no-titties were now in a bra. So far so good. Jill followed, watching him closely, obviously concerned for him. Sam sat down abruptly on the couch. Jill suddenly turned very bright, as if she had flicked a switch.
She went over to Art and said to him, "Hi, I'm Jill. We're going to see a lot of each other I think, at least tonight we are! Ready to begin?"
"Sure," Art said. He seemed a little confused, but willing to go along. He'd had two drinks before Jill got home, and the huge one I'd just given him was beginning to reach his brain.
"Well, Art. Before we go out to dinner, Jane and I want a little taste of things to come. Do you have anything like that?"
"Things to come? Oh, yeah, cum. I sure do, Jill. Do you wanna see it?"
Jill produced four large napkins. "Oh no, Art. Seeing's believing! That comes later! Right now Jane and I want to seat you and Sam side by side, blindfolded, and we'll be blindfolded too, and we'll go down on you guys. OK?"
Art nodded, thinking no doubt that he'd really lucked out tonight.
"Only we'll none of us know which of us is doing who. Then later on we'll find out, by the way your cocks and our mouths feel, and by whose cum tastes more familiar. It's a game. Wanna play?"
"You bet," Art said, lifting his bulk out of his chair, walking over, and settling himself in a chair next to the couch where Sam was sitting.
Jill handed me two napkins and told me to cover Sam's eyes and then mine. I went over and blindfolded Sam. Jill waited a moment, so Art could see Sam with his eyes covered, and me tieing a blindfold over my own eyes. Then she blindfolded Art. "All secure?" she asked. "Can't see a thing," Art replied.
Sam took his blindfold off and looked miserable, and I set mine aside too. "All right," Jill said, "Now none of us can see. Why don't you two men stand up and change places, or maybe not, so we won't know who's where." Sam stood up abruptly, then sat down again in place. Art stood, shuffled tentatively, felt that Sam was still where he had been, and sat down again. "Now, Jane, out with his meat. Whoever you're in front of."
"You bet," I said. I sat down on the couch to watch. Jill unzipped Art's fly, and with her long, smooth hand with their lovely tapered fingernails, she worked Art's cock out until it stood tall out of his trousers. Art could feel it was a woman's hand, and he swelled up to gigantic size. I'd seen one or two bigger, of course, and Jill and Sam had seen to it that I'd fucked bigger, quite a few times in fact. But Art was up there in competition with the best, and I saw he'd do very well for Sam's deflowering, Sam's emasculation in Jill's eyes. I grinned, and almost laughed out loud. Art's prick could have been the model for that monstrous dildo Jill and I had forced up each of us so often. It was like a baseball bat in shape and thickness, with a huge purple cock head. Sam's eyes bugged out.
"And now out with the other fella's meat," Jill said. "Is it out?" "Oh, yes," I replied. "Boy is this guy hung!" I was delighted to see this scheme of Jill's working so well.
"Now, gentlemen, the ladies want to take their pleasure. We just don't know which lady or which pleasure, that's all. From now on, no hands!" Jill stood and touched Sam on his shoulder. He slumped out of his chair and fell to his knees between Arts legs. Jill silently opened her mouth wide, hid her teeth behind her lips, and motioned to Sam to do the same. Sam fixed his eyes on her, looking pitiable. It was obvious that Jill was going to direct him through the whole exercise. This was better than my first session with Tom, when my mouth first lost its cherry, many cocks ago. My masculine pride never really did recover, and I hoped the same for Sam.
Jill licked the tip of her thumb. Sam leaned forward and touched his tongue to Art's huge cock head, right where a drop of pre-cum had appeared. She swirled her tongue around her thumb tip. Sam swirled his tongue. Art leaned back slightly, feeling pleasureably serviced. Then Jill plunged her mouth all the way around the first joint of her thumb, and up and down two or three times. Sam looked pathetically desperate, and a wild look came into his eye. He opened his mouth to its utmost and took in the whole of Art's cockhead, to just below the ridge. He looked over at Jill, and it was obvious his mouth was straining full. There was no way he could slide his head up and down. Jill signalled he should begin to suck, and while sucking hold Art's cockhead firmly in his mouth, and pump the whole shaft up and down with his head. So he did. Art's cock grew more in Sam's mouth, and it wasn't clear that Sam could ever get his mouth off it again. Jill made an exaggerated tongue motion, and somewhere in his mouth Sam did the same, still pumping. Art let out a groan.
Jill then removed her mouth from her thumb and made some elaborate licking motions up and down the whole extended thumb, and licked the joint at the base of her thumb, then up its length. So did Sam, for a while. Then Sam returned on his own to sucking Art's prick, but this time he angled his neck to take more in, far into the back of his throat. Art started twisting his hips, and soon the two of them had set up a powerful rhythm, Art fucking Sam's face in and out while Sam bobbed his head over Art's prick, like a big bird in a garden full of worms. Faster they went, until finally Art hoisted his pelvis all the way out of the chair and into Sam's face, and shouted "Now! Now! Now! Now! Swallow it, Bitch! Swallow it, Bitch! Swallow it, Bitch!" The Bitch in question did his best, but couldn't get it all. His Adam's Apple worked furiously—he swallowed over and over, but slick cloudy ooze began to come out of the corners of his mouth, just as I'd hoped. Then he lost his grip on the head of Art's cock, probably because it had gotten too slick, and the last few pulses hit him full in his face and hair. So there he was, his nose and face dripping cum, eyes tight shut, his mouth still twisted wide open as if his jaw had unhinged and he couldn't close it, his face a mask of tragedy. Jill was watching him with concern, but also with disgust. Her mouth was set rather tight.
"How can he help but want to be a woman now that his mouth has tasted cum," I said quietly to Jill. "Do you think he's ready to slurp jism twenty times a night, the way I can? Do you think he'll make a good slut?"
Art must have heard the last word or two. "She's a terrific slut," he said. "That was the best head I've had in years. Lots of girls can't handle a prick like mine. Now who was it? Jill? Jane?" He started to take off his blindfold.
Jill stopped him. "No," she said in a throaty voice. "More! I"m hot! I want more! Give it to me baby! Up the ass! Are you man enough? Here, Art, put your finger in my ass. I can't wait for you to get hard again! Oh, yeah!" She looked a little disgusted with herself, producing that cornball slut talk. But her instincts were unerring. Art bought it all, and leaned back. She produced a tube of jelly and motioned to Sam to drop his pants. He did, and his underwear, and Jill immediately saw a problem. He had the hairiest backside I have ever seen. But Jill improvised brilliantly. "Yeah, grease that place between my smooth, ripe melons," she said to Art, and loaded his forefinger with jelly, and lowered her panties, and backed over his crotch, and crouched down so he could feel her rear. He began running his hands over her cheeks, which I must say I have always admired, usually from a distance, and he started trying to insert his huge tube, which had never gone all the way down and was now re-inflating. "No, grease me up first, or a great big cock like yours'll tear up my little lovehole," she said. This information she directed pointedly to Sam, with a warning expression on her face. She filled three fingers with jelly, and beckoned to him. He understood. He backed toward her and bent way over, his face now fearful.
"I gotcha, sweetbuns, first the coming attractions, then the main event," Art said, working his jellied forefinger into Jill while caressing her smooth, ripe melons. This was far better than I'd hoped. A daisy chain of finger-fuckers! Aa Art invaded her she winced, but kept her mind on her job, which was working three fingers into Sam, whose anal opening was obviously rigid and in spasm. With her long fingernails she didn't dare force anthing. So as Art warmed to his work and began to fingerfuck Jill's hole, slow at first then faster and faster, his prick still rising toward its former glory, she slapped Sam on a hairy cheek and said "Relax, you sunofabitch, or you're surely gonna regret it!" Sam gritted his teeth, and lowered his eyebrows, and Jill got a finger into him. A minute later a second finger. She fucked him with these two for a while, and he kept his eyes closed as if he were somewhere else. Finally she got a third in, and pulled out, and regreased, and re-inserted, and worked all three into Sam as deep as she could.
"Now, baby?" Art asked. Jill obviously wanted to get Art's finger out of her butt. "Now, baby!" she replied. She stepped forward and Art lost his purchase on her. Then she deftly twisted, filled her palm with jelly and slathered it all over Art's monster cock, now fully grown again. She then took Sam by the shoulders and backed him into her former space over Art's shaft. Then she pushed Sam's hips down so his slippery anus was pressing onto the head of Art's slippery prick. "You're on your own now babe," she told Sam. "Then here I come at you," Art replied. Art grabbed Sam's hips to hold them steady, and thrust full force at the anus he could feel between the cheeks he could feel through the layers of jelly.
"AAAaaaoooOOOOOhhh!" Sam shrieked in the highest falsetto I have ever heard from any man's throat. His maidenhead had gone into memory, in a single soprano outcry! He was obviously in great pain, but physical or mental I couldn't tell. "You like it, huh?" Art replied, "Well there's more where that came from." He started pumping, and with each pump added another inch of his cock to the massive meat Sam's ass had already swallowed, until finally he was all the way in. Sam then reminded me of Jill when she had first gotten that whole massive dildo into her pussy. He crouched over Art's lap, rigid, not daring to move, impaled in a kind of catatonic stupor, while Art pumped away at him from below. I watched fascinated. Jill had trained me for months to survive what Sam was undergoing in minutes, and was feeling inside himself right now. I'd taken some monsters, and knew what could happen. Sure enough. As his pain subsided, Sam's dick started to rise, and as it got more and more erect he grasped it with one hand and started to stroke it, obviously unaware of what he was doing, because his ass also began to move back onto Art in the same rhythm Art was using on him. Sam's prostate and all those internal nerve endings squeezed deliciously against Art's meat, and betrayed him. He moved faster and faster with Art, and finally they both came together in a crescendo, Sam spurting into the air and our carpet, Art unloading deep into Sam's bowel while shouting, "Take it, bitch, Oaghh, take it, bitch, Oaghh!" over and over. Jill watched the two of them with loathing. I burst out laughing! Here was yet another man who had given up his mouth's and his asshole's virginity for the love of Jill! I wondered if we should form a club. Art's penis softened a little and he pulled it out of Sam's ass with a "POP" sound. Cum dribbled after.
Art then took off his blindfold and saw Sam's ass, and puzzled, looked around it to see Sam's face, cum from the earlier encounter still oozing from the corners of his mouth, his face and hair still sticky. "Sam!" said Art. "What're you doing there? Did you set this up? Are you a faggot? You really like eating my cock? You really wanted me to fuck you? Hey hey!" And Art grappled with this information. It was hard to tell from the numb expression on his face whether he was next going to kiss Sam or deck him. Maybe both.
Sam started to stand up, but Art held him in his crouch. "No, Sam, we're not done. Now I know you like cock, we're going to have some great old times together. Some days in that office I just have to beat off, maybe two or three times a day, just to keep my mind on my work and off the secretaries. The way harrassment cases go these days, I can't propose anything to a secretary, I bet not even marriage! But you know what I want, Sam! And all this time you wanted to give it to me! Now when I get a boner I'll know who to call to take care of me. Sam! I think this is terrific!"
A sly grin came over his face. "Tell me Sam, are you a real Queen?" Art felt through Sam's shirt and found the lines of his brassiere. "Oh, Sam, you're a queen all right!" Suddenly he looked up at Jill. "But he's your boy friend, too, isn't he. And there you were, setting things up for him. Well, that's love. I can respect that! Can we share him?"
Jill watched this whole scene white-faced, her mouth still tight. It was obvious she had not wanted to see what she had seen, nor to hear any of this. And it was obvious that despite everything she knew about duress, and rape, and victimization, Sam her all-man romantic companion and future husband was changing in her mind at that moment into one more potential pansy in pants, who got off by thrusting his asshole repeatedly onto the first cock to enter it.
Then came the capper. "Don't get up, Sam," Art said to him with just a hint of threat. "You shouldn't have tried to fool me. Now let's do it right! Here!" And Art took Sam's head in his two huge paws and turned Sam around, and forced him back onto his knees, and began to rub his face on his crotch. His monster penis hadn't lost all its erection, and Art said to the creature between his knees, "There, there, Sammie girl, suck on it. Lick it. Clean me up. It's a reasonable size now. I bet you can handle it. I bet you can deep throat all of it. Try!"
So Sam started in again, bobbing his head. Jill went into the kitchen, unable to watch. I went in with her, and sat down at the table and signed my whole former life over to her, just as I'd promised I would.
Now I was legally and officially a woman named Jane. Jack no longer existed. I'd even proved, I realized, that I could be as bitchy as the next woman if sufficiently provoked. I really was Jill's creation! And now, I realized, I didn't mind at all! Despite everything, she'd done me a favor. I freshened my makeup and said to her, "Well, Jill. You were right! That took exactly thirty-five minutes. Now if we can unplaster Sam from Art and clean him up, shall we go to dinner?"
The next week she and Sam quit their respective firms and left town together. Maybe they're still together, though whether they're each still the same gender is anyone's guess. Jill always had the balls in our relationship, and maybe in her relationship with Sam too. She didn't have to talk anyone into getting castrated. She just went ahead and did it to them in her own way!
But as far as we were concerned, Jill had the last word. I'm still pretty much the way she made me and left me. There aren't many men who want to date me, though I present well as a woman—in fact I'm rather pretty, and I know how to dress well and enjoy it, and how to satisfy men sexually. But that's still not enough. As I said when I began this whole long tale, I prefer girls. But there aren't many who want me for anything other than a friend. I have some very dear girlfriends, and I love them, and they love me, but there's no romance between us. Some feeling has returned to my penis, but that hormone bath did short-circuit my erections. I get them, sort of, but they're soft, and it's a rare girl who'll take a chance that I can get firm enough to fuck her. So instead, until I find that special someone who'll love me the way I am, I date men, and they play with my titties, and that feels as wonderful as ever, and I'm fucked.
When Jill left town she sent me a checkbook for one of our joint bank accounts with some money in it, enough to help me get by as it turned out. And she sent me a note telling me that I'm now a lot better off than when she first met me. True enough. She said she was glad she had feminized me, and hoped I didn't resent it. I don't. And she finished by asking, "No hard feelings, right?". Nope, none.
End Jack and Jill.
© 1995 by Vickie Tern
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