"Jack and Jill" is a novel in ten chapters averaging 30k each about a fictional crossdresser like you or me in fact or fantasy or remote curiosity, or else why have you read this far, and how he or she became the person who is narrating the story. It's mostly TG and femdom, with forced or tricked or cajoled feminization, but of course also m/f and m/m and f/f in various u.c. and l.c. combinations, and also some d/s, and other such alphabetical stuff. Humiliation, yes, and mental but not physical bondage. There is no pain, and no magic or incest or bestiality or pedophilia or snuff, and no characters below the age of consent, so if these things turn you on, or if you're yourself below whatever age is lawful, this isn't for you.
You'd find this story boring, anyhow. The characters aren't always in the sack with each other, not always. The main character believes, as many adults do, that we are reasoning creatures who can understand and cope with our predicaments by thinking them through. Not so, but such people do a lot of thinking aloud, explaining themselves, and that's part of the fun. They keep being surprised when events or other people's schemes cross them up and mess their minds.
It's fiction, but any resemblance to actual persons or events you have known, though accidental, is deliberate. A fiction that doesn't resemble any of the worlds we inhabit, or any of the imaginary worlds that inhabit us, isn't worth reading. It wouldn't even be imaginable.
Jack and Jill
by Vickie Tern
I live alone. Oh, I've got a few girlfriends, and they fuss and worry over me sometimes, and sometimes they arrange dates for me and we go out together, and sometimes I arrange my own dates. But dates are always a problem. I don't know which gender to ask out. I look like a girl and I dress like a girl, and I live like one, and I work like one, as a kind of secretary-typist-administrative-girl-Friday who doesn't mind solving her boss's computer programming problems for him when he's stuck. And by now I even act like a girl, and swing my hips when I feel real good, and let my hands fly all over when I'm excited, and squeal with my girlfriends when we're thrilled, and call things "just precious" and "darling" and all that. But I'm not a girl. I'm a man who's been feminized, by his former wife, if you can believe it, because I wasn't man enough for her. People call me Jane, but my name used to be Jack. And I still like girls, and inside my pantyhose I still have the basic equipment for coping with them, though it doesn't work too well these days.
My problem is, how many girls want to date a man who has breasts and delicate manners and wears dresses and loves to talk about girl things? Even the lesbians are turned off when they find out I'm not a proper transexual woman, but a normal heterosexual male who has always loved crossdressing and who happens now to live in a mostly female body. And how many guys want to go out with a guy who may look like a girl, but hasn't got a pussy and isn't gay? Oh I'll blow them, because what else can I do to please men if they're not into buttfucking, but there's not much in it for me sucking on other guys' dicks or getting my ass plowed (well, there's a little something, I do like it, my wife saw to that). But sooner or later guys catch on that I'm not hot for them, and sooner or later they don't come back. So I'm sort of caught in the middle.
Probably I should go the rest of the way and have surgery and become a proper woman and live a normal life. Or maybe I should go back to being a man, if I can. A few more shots and cuts either way might send me either way, I suspect.
But the problem is, I like looking like a woman. No, that's not true. I absolutely adore looking like a woman! I always have. The most wonderful thing I see when I wake up each morning is my mirror. I just love seeing a pretty face and a well-turned feminine figure looking back at me (see? -- "I absolutely adore," "I just love"—my femme talk turns on when I'm turned on, and just thinking about my mirror turns me on!). I love feeling pretty—there's such a marvelous glow to it! On the other hand, I don't want to BE a woman. I can pretend, and even fool myself sometimes. For some things, like feeling soft and warm and cuddly and loving with someone, being a woman is just lovely. But for most things I feel like a man, not a woman. Besides, if I actually were a woman and I felt like one and dressed like one routinely, where would be the thrill? Would I still feel deliciously excited each morning when I put on a dress and step out knowing I look pretty, my whole body feeling perky and blissful and privileged? Probably not. Probably, I'd just feel normal, like any woman wearing any dress anywhere.
I'm a transvestite. I love looking feminine, and I love the way it feels to look feminine. I guess I was born one, and I'll certainly die one. And that's where the problem started, how I got to be where I am right now. I love wearing women's clothes, and I can't help myself, and I don't really want to help myself. And now I live in them. I've got what I wanted, or what my wife wanted for me. I'm permanently cross-dressed.
I crossdressed sometimes when I was a kid. I loved the feel of a bra tugging on my chest, or a slip or a dress swishing on my legs. My mother and sister never found out I was in and out of their clothes, but it wouldn't have mattered to me if they had. I was hooked. I got a paper route to help support my habit, to buy my own girls' clothes. Once I rode out at first light wearing a blouse and skirt, cycling furiously with my heart pounding and throwing papers at doorways at top speed, scurrying to get back before anyone woke up and saw me. I felt terrific about it at first, really high. But then I started to think about the chance I had just taken and I started shaking and couldn't stop! What I had just done terrified me!
After that I went deep into the closet, ashamed that I wanted to look like a girl, and afraid to be found out when I did look like a girl. Like most cross-dressers I got disgusted with myself and quit, a few times, but then I'd start up again. When I finished college I wore skirts and dresses all the time when I got home from work, all around my apartment. I felt so right in them, so ...together. But I never dared wear them outside. If someone were to look hard at me when I was outside trying to pass I knew I'd feel embarrassed, then humiliated, and then I'd panic and run, or come apart some other way. Then everyone would look hard at me.
When I first met Jill I had just quit again, and it was just as well. Jill was never a woman to think a cross-dressing husband kinda cute. In those days, sexually, as far as I could tell, she was not given to experiments or kinks of any sort. She wanted a husband she could respect, a friend, one not too demanding. Sex for her had to be strictly penises and vaginas, and that's what she called them, not even oral. And sex for her was an occasional recreation, not a kind of marvelous and crucial compulsory behavior. She's a very good-looking woman, a lawyer, tall and slender, with a decisive manner that keeps her clients confident that she knows what she's doing. When we decided to move in together I thought I would stay quit. We got along well. We liked being with each other. At first she thought that my name being "Jack" and hers "Jill" was just too cute for words, that we couldn't possibly be compatible. But she weathered the kidding from friends and associates, and we found that we were able to get on, pretty much.
I respected her a lot, and she admired the way I did my work. We could talk about anything, and she'd listen to me carefully. Then she'd ask a few questions. Then she'd let some time pass, and finally she'd deliver her own views as if she were a judge presenting a final opinion. After that the question, if there was any, was settled and not open for discussion. Usually we agreed, so I didn't mind that the final decisions affecting both of us were usually hers. I got to assume that was the way things should be, and I liked the way she ran our lives. It saved me a lot of hassle. I think she was the one who decided one day that it was time we were married, and I certainly didn't disagree. By then I depended on her self-confident self-assurance, and looked to it for guidance. I thought this was love.
Once I tried to tell her about transgendered people, people like me, trying to lead up to a confession that I had once been one of them (and, I guess I hoped secretly, might be one of them again some day). I thought I was being casual enough, but she turned the topic off abruptly. She muttered words like "sick" and "perverse," and looked at me closely. She then asked me in her attorney's voice why I had raised the subject. A pang of fear sliced into me, and I said quickly that a client had joked about it, that's all, and as soon as I could I left the room to settle down, my heart still pounding furiously, still terrified. A narrow escape. So my pleasure in wearing girls' clothes stayed underground, hidden even from me. After a while I thought there wasn't any. Which is why I didn't tell her anything before we got married.
I began dressing again during our honeymoon. I know this doesn't sound like a great compliment to Jill's sexual attractiveness, and I mean no disrespect. But desire for a woman and desire to look like a woman were very nearly the same thing for me. And back then Jill was—well—deliberate in her lovemaking. Most of the kinds of love people like she found "distasteful." She loved being in charge, controlling events and controlling her feelings about them. If it wasn't cuddling, and it wasn't vaginal intercourse, she didn't care for it, and she made that known whenever I'd try to roam further with her. I knew from when we started living together that she was severely inhibited, and I hoped she'd loosen up in time. But it didn't matter. I needed her, and I had come to depend on her, and she seemed to care about me. I would marry her again, even now, despite everything she did to me. Maybe because of everything, in a way. But not for the sex when we first got married.
I still remember the morning in the hotel when she asked me to hand her a white, delicately embroidered slip from her bureau drawer. I picked it up and started toward the bed to hand it to her, and felt the most delicious "THWANG!" as my belly rose up in joy at the feel of the lovely thing in my hand, and my prick rose up too. Before I knew what I was doing I had unfolded it and held it fitted in front of me, admiring the lace across the hemline. "Very funny!" she said, as she took it away. Then when she noticed my aroused state, she asked, amused "Why, Jack, what can you have in mind?" I certainly didn't tell her what I really had in mind, but one thing leads to another, and it was easy to distract her.
That afternoon I stopped at a lingerie store and bought myself a slip just like hers, and later that afternoon I hid it in our hotel room in the back of our closet, so it would seem to have been forgotten by some previous guest if she found it. She never did, and that was the beginning of the stash that has since become my proper wardrobe. The next morning while she was off having her hair done I put on one of her brassieres and then my slip. It all felt so exquisite that I threw a golf shirt and slacks on over them, and feeling delicate and dainty and sweetly feminine, I went back to the lingerie store to buy my own bra. I bought two, because I couldn't decide which was more "me," a satin underwire, or a stunning lacy whisper of a bra I just loved at first sight. Barely married, I was at it again, and absolutely delighted to be at it again.
For a few years Jill never knew. As a lawyer she was very hard working, and tough and devious I was told, and I could believe it. She left the house every morning at eight and returned every evening at six, often later when there was a big case brewing. I was then an electronic systems designer, mostly computing systems. I wasn't the cleverest one around, but I was precise and reliable, with fantastic speed when I was writing up or solving problems, and that was my edge. My client list kept growing because my programs always worked, and were always installed on time. I kept a small office for consulting and for storing the stock modules and menus I custom assembled for each client. But until Jill found my clothes and demanded to know what they were, I did a lot of my work at home, dressed and made up like the beautiful woman I wanted to imagine myself, enjoying myself immensely. Then I'd modem or fax it in.
At the other end of the fax was my secretary Darlene. Darlene was no computer whiz, and no great brain either. But she knew the alphabet, and she could be trusted to file any papers marked up with one of its twenty-six letters, then to find them again and fax them out to the house when I asked for them. She also impressed the hell out of clients who came in to see me, and that was why I kept her on after I found she couldn't do much else. She didn't need to. There she sat in the reception area all day long, being gorgeous and fixing her makeup and tucking in her curls, and answering the phone in a bedroom voice so sultry people would think at first that they'd reached some 900 number somewhere else. Her voice and appearance could seduce anyone into being a client. I'd talk to Darlene a few times each day, and I'd see her a few times each week when I went in to the office, and if it had been any more frequent I'd certainly have gotten the hots for her myself, and maybe what happened wouldn't have happened, at least not the way it did. Jill wasn't happy that my secretary was such a Barbie doll, but she knew that Darlene was just right for what I asked of her, namely not much, and that she was even better for what I didn't ask of her, namely to keep clients eager to call the firm with repeat business. She knew that I never saw much of her, because I was mostly home. So that was no problem.
We settled into a routine. Breakfast with Jill, mostly just coffee and toast or a roll, me unshaven and in jogging clothes as if ready to hit the old streets. Then as soon as Jill left for the day I'd shave twice and change into a pretty outfit from the skin on out, bra, panties and stockings with garter belt or girdle or maybe a pair of pantyhose, slip, skirt and blouse or maybe a dress, or maybe a suit, or a slack suit, and pumps, strappy heels, flats, or sandals, depending on the season and my moods. I loved starting to dress by whim, in a mid-calf full skirt or a slutty mini, and then matching everything else to that first random desire, so by the end of the process I was dressed for the day, wearing appropriate jewelry and settled in to work feeling elegant and tasteful, my ensemble different each time. My hair is full and I let it grow to cover my ears, so I could brush it back when I went out as a man, and I could blow-dry it into a page boy to look feminine as soon as Jill left the house, or even curl it when I wanted to take the time.
Since I was home more than Jill and my time was more flexible, I did most of the shopping. Sometimes I took to dawdling in the supermarket at high risk, I thought, wearing women's shirts and pants, loafers and "natural" (that is, invisible) lipstick, and with a feeling of enormous risk maybe a touch of eye makeup. Beneath this undetectable femininity—not even androgynous, I realize now—I wore wonderfully seductive bras and panties and slips and teddies that would have reduced a cave man to paralytic gibberish if he'd seen them on a cave woman. Once I dared fate by wearing a flowered shirt that buttoned the wrong way, living on the edge I thought. But I lost my nerve and never unbuttoned my jacket to show it.
I never dared to go further, to appear in a skirt, or in unambiguous makeup, because I was so terribly ashamed of this delightful compulsion. To be found out would be devastating I thought, an embarrassment I could never live down. My manhood was at stake. For a man to look like a girl was demeaning, ridiculous. I shared the world's view that an effeminate man is contemptible, a clown, a sissy, a fruit, a joke, fit target for any insults. Even behind closed doors and drawn shades at home I felt dangerously at risk. There was a twinge of anxiety most of the time I was dressed, even at home, and I kept my oversized jogging outfit on a chair as emergency cover gear if the doorbell should suddenly ring. But I loved every minute of it. I adored that image in the mirror, posing and primping. Nothing was too good for her!
I also loved every minute I spent shopping for more clothes. When I finished an important piece of work I'd reward myself with a special treat. Dressed like a man, I'd carry into the store a slip of paper with my sizes written on it, and I would seem to consult it as I pawed through rack after rack of beautiful skirts and bodyshirts and dresses, looking for the one item I simply had to have. I hoped all the salegirls would assume I was buying for someone else, and I consulted my paper frequently, as if women's sizes were obscure and beyong comprehension. As if this persuaded them. As if they cared. But I could not risk seeming to be what I was, even to strangers. I was a man. To dress like a woman was to be no man, to be less than nothing.
All this gear grew in bulk, and soon occupied the closets and drawers of my workroom and of another spare bedroom in our oversized house, places where Jill never went. But it happened finally. One day when I was at the office Jill came home early, wondering whether a spare bedroom might make a home office for her weekends. She looked in on mine, and at the size of its closet, and at everything in the closet, and then she looked at closets and bureau drawers in the other rooms. Lawyers are careful and thorough, and by the time I got home she had located my whole extensive collection. She had also reached an exact understanding of everything. She had concluded that while she was at work I was keeping a variety of women in the house during the day, a slut who wore leather minis and tight tubes and cutoffs, a businesswoman who wore severe suits, a housewife whose tastes ran to sundresses and flowered prints, and from all the drawers billowing with sexy lingerie, a whole whorehouse full of high class call girls.
When I got home my life ended, my life as it had been up to that moment, anyhow. In a tight voice she demanded to know who these bitches were, and how I dared bring them under her roof. Incoherent, humiliated, mortified, hysterical with fear, tearful and stammering, for the next two solid hours I desperately tried to persuade her of everything I had been trying to hide from her ever since our honeymoon, the unacceptable truth about me. I pointed out that all of the clothes and shoes were of one size, mine. All that proved to her was that my taste in the women I brought home was self-absorbed and narcissistic, and she said that from my behavior in bed she'd suspected as much. I tried to convince her that no women would ever consent to leave so much clothing here. Too vague an argument for a legal mind to accept. Desperate and red-faced, I finally stripped off my jacket, shirt, tie and pants to display show her that even at that moment I was wearing a matched embroidered slip, bra, and panties, all in the same size as the clothing she'd found, a variant matched in brand name as well as size by other brands and sets and styles and shades and colors of the other garments hidden in my closets and dresser drawers. She was horrified to stare at my body clad in its delicate lacy harness, and for once she was speechless, as traumatized in her way as I was. Only then did she begin to believe it was possible the stuff was mine.
So she sat me down and cross-examined me, relentlessly. When, how, bought where? She kept returning to Why, and I had no real answer. What finally persuaded her was my high marks on a tough quiz she herself set and judged. Men never know anything about women's styles, she was convinced, and she never hesitated to say it when I'd recommend that she wear something I thought becoming to her. But I'd spent a lot of time trying to look nice, even elegant, and I'd shopped with an eye toward completing different outfits, and I'd kept up with the fashion magazines despite my envy of all the beautiful women who populated them. I did have reasonably good taste! She sat down and said, for example. "Those red three inch heeled pumps! What would you wear with those?" And I hauled out of a drawer the black pullover sweater I'd worn with them, and from the closet in the room next door a matching red full skirt; then I pearl-dived into my earring box and found a perfect pair of dramatic coordinated black and red clip-on hoops. Or she'd say "That blue and gold cocktail dress with the slit to the waist, if it isn't higher—what stockings go with it?" and I came up with them, and "Is there a purse also?" and I came up with a darling little matching clutch bag I'd found in an opportunity shop one day, not believing my luck! Little by little she began to believe I had spent more time on my outfits than on my computer programming. Maybe I had.
She took due note as I folded each sweater carefully before putting it back, and settled each blouse neatly on its hanger before hanging it away -- obviously I knew and cared for each article the way she cared for hers. She knew that in male mode I was a slob, my pants and jackets ending up wherever I tossed them. I knew she was persuaded when she came out with "That silver miniskirt—that's for a teenager looking to get laid! How dare you wear such a thing at your age?" I showed her the ruffled blouse that kept me looking demure above if a little slutty below.
Then her interrogation went on to its next phase. "I don't see any outer garments. Where do you keep them?" she asked. I told her there were none, that I never dared walk out even into the back yard when I was dressed. She was astonished, and unexpectedly, angered by that answer. "You don't flounce about outside in those things?" she asked, "Why not? Are you ashamed of your perversion? Are you ashamed someone might think you're a woman, or something else equally demeaning?" I told her I was strictly a closet TV, terrified of being found out, that my manliness would be compromised if it were known. "It isn't compromised by the fact that you do it?" she asked. Then, again, "Why do you do it?" I told her I didn't know myself, but that I had always wanted to do it, that it was sometimes pleasantly erotic and always deeply satisfying, and that it was a kind of compulsion, maybe inborn. I started to tell her about the way it allowed me to express my feminine side, and how gender and sex are different things, gender being in the mind, and all that, but she wanted to hear no part of it. I compared it to homosexuality, another gender orientation people don't choose but discover in themselves.
That started a new round of ferocious questioning. "Oh, Jack? Do you get together with other perverts, and do twisted things with each other?" She sounded as if she couldn't even imagine what those things were. I assured her that gays and transvestites were altogether different, that gays are attracted to people of the same sex but transvestites are so strongly attracted to the opposite sex they want to look like them. I told her there were hundreds of thousands of transvstites like me though I personally knew none of them, and that no one knew about me except me, and now she knew. "Why do you want to be a woman?" she asked again narrowly. I assured her I didn't, but that I loved looking like one, and that when I looked beautiful, all my desires focussed all the more on real women. On her, I added quickly. She was not convinced, but continued, "If you like to look like a woman, why don't you want to be a woman? Why don't you want other people to know? Why do you hide it from me, your own wife? It's disgusting, but is it so shameful?" I assured her it was, or I thought it was, and she glared at me. Then she was silent. I awaited her verdict.
"I see," she said. Then she said cryptically, "Everything fits!" And then she sat silent again. Ominously silent.
I couldn't stand it. I said, "So now you believe me?," and she glanced at me with enough contempt to wither a rainforest, then glanced away again, and said nothing. She was convinced. I had been moved in her mind from her frying pan into her fire, from a mass adulterer to a pitiable, self-confessed drag queen, a hypocrite sexist wimp filled with fear and self-loathing.
It was my night to serve dinner, and she sat through it frowning, deliberately not looking anywhere I might catch her eye, chewing slowly, saying nothing. As I poured the coffee she suddenly looked up and said, "All right! Here's how it is! I married a man, not a woman, and not an imitation man and not an imitation woman. I don't care what your fantasies are like, or why, or what your so-called inborn compulsions are like or why. I think you can stop, and you should stop, and you will stop. From now on the only women's clothes in this house will be mine. The only person wearing women's clothes in this house will be me. You will be a man, and you will dress like one. You will act like a man. Or else I will leave you, and I won't mind telling all of our friends why I'm leaving you." She paused. "Coward!" she spit out.
I hoped this was her final pronouncement, so we could begin to discuss things more calmly. But then she added, "No talk! No explanations! No pleading! I want promises from you first thing in the morning, Jack, my so-called husband Jack, or I move out." She then went straight into our bedroom and slammed the door. I decided I had better spend the night in a guest bedroom.
No opportunity to talk, and no appeal. No way to ask even obvious things, like was there was a deadline for moving my dresses out, or where I should put them, or did she mean I should throw them out. Before this I had seen her ruthless decisiveness, the way she would speak her mind by uttering an ultimatum. But those dealt with trivial things, like whether pizza or other such unhealthy foods should be allowed into the house, or whether people who make porn movies should serve long jail terms. She could be sharing, and lively, and fun, and she could usually talk me into anything. But she could also switch on her lawyer mode, as heavy and unyielding as cast iron, and then I was afraid to dare to want anything she didn't want. This night would determine the end of our marriage or its continuation on her terms. And for me, life outside our marriage had become unthinkable.
I couldn't sleep. Then the next day I folded, or rather, I came apart. I promised to do everything she asked, and that I wouldn't do the things she hadn't asked, or rather, that I would stop dressing at home, and that I would clear everything out of my closets, all the women's clothing, that is, not the men's. I told her that as far as women's clothing was concerned, from now on she could wear the pants in the family, and then I apologized that I wasn't being sarcastic when I put it that way. I told her I loved her, that she was the center of my life. I started to cry, then I couldn't stop crying. She nodded, looking a little sour, and I was still blubbering when she left for work without a word.
That same day, I got a stack of boxes from a transfer and removal company, made trip after trip, and brought all of my clothes to the office. When I showed up in the reception area with the first box Darlene raised her beautifully plucked eyebrows, checked her lipstick, and asked what all of this was about. I told her Jill asked me to store a lot of boxes here, figuring Darlene wouldn't have a followup question. She didn't. I stacked them out of the way, against the wall in the large utility room where we kept the xerox, the coffee maker, and the office supplies
Within a month I was back at it, this time at the office. I took to coming in early on weekdays, every day, opening a box of lingerie and putting on panties, slips, teddies, stockings, and bras under my business suits, so I could feel them hugging and tugging at me all day long, then undressing and stowing them again after Darlene had left for the day. I had the Reception area of the office mirrored, which made it look bigger, and pleased Darlene because now she could see herself from her desk by looking in any direction. Saturday or Sunday I'd plead heavy overwork to Jill and head for the office, and then I'd spend the day in a specially treasured dress or pants suit, or just pass the time changing from outfit to outfit, admiring myself a little wistfully in each, then trying the next.
Jill's mood seemed different after my unconditional surrender, or maybe it was how she felt about me that changed, along with her idea of who she had married. Obviously I was no longer her Prince Charming, but some kind of would-be excuse for an imitation woman or an imitation gay man, neither one nor the other. We fixed dinners for each other as we had in the past, but instead of saying appreciative things when I put in extra effort or she especially liked something, she'd say "Well, at least this one came out all right, for once." Or if a dish wasn't to her liking, then she'd say, "If you can't do it properly, why do you try to do it at all?" When her turn to cook came around, as often as not she'd pick up takeout on the way home from work. She did not wish to serve me.
In bed she behaved the same way. She was never an enthusiastic lover, as I've explained, but now Jill ...well...was not even affectionate. When I would put an arm around her as we settled in to sleep, instead of snuggling in at me she just lay there, and if I began to caress her she'd say "Didn't we do this already this month?" or "I'd rather sleep, but if you have to, try to pay attention to my needs for once." After a while I quit trying. She didn't seem to mind. But at work, whenever I stepped into a pair of hi-cut nylon panties I would get all the more excited, and after a while whenever I was dressed I would masturbate like a teenager. On weekends at the office, when I saw my mirrored image in an exquisite white chiffon summer dress, I could hardly keep my hands off myself, and I didn't.
I wondered if talk of separation or a divorce was in order, but I realized I shouldn't raise the topic -- she'd simply say "You'd like that, wouldn't you!", and leave me all the more aware that she would rather continue to punish me for not being the person she had thought I was. There was a breach of contract here, and I had penalties to pay. We had our circles of friends, and we went to parties and dinners with them, and Jill never let on there was a problem. As a lawyer and as a woman, she hated to lose, and she wouldn't quit with me even after she was convinced she had married a world class loser. And I realized I didn't want to lose her. She wasn't fun, but her certainty strengthened me. I didn't want to live on my own any more. I needed her. I wondered whether the feminine in me was responding to the masculine in her, but I couldn't think that one through, and I decided finally that she'd get over her resentment if I waited her out.
Then something odd happened. Darlene looked disturbed one afternoon as I came through the outer office, wrestling through things in her purse, and opening and closing her lower drawers as if looking for something. "Something missing?" I asked her. "Not exactly," she said. She hesitated. "Uh, you don't happen to keep any tampons with your bras and skirts and things in the utility room, do you?" I was shocked, and said nothing. I replayed her words in my head unbelievingly. "Oh, never mind," she said, "I'll check next door and see if Vera or any of the other girls has any to spare." She started to get up. My hair still stood up, and I felt struck in the stomach. I had to answer something, so I said carefully, "No, why do you ask?" Mistake right off. Better if I wasn't supposed to know what "Jill" had put in those boxes. Darlene was still looking for her purse when she replied absent-mindedly, "Oh, I've run out, and I thought maybe when you got dressed up in those cute outfits you also put in a tampon. My brother did. I better go see if Vera can help me." She got up, went out, and headed down the corridor.
I went back into my office, and sat down with my mind roiled and running half-crazed. She knew! But she didn't seem to care that she knew! I had been hiding from her for months. But to Darlene, my dreadful secret was no more than a possible source for tampons in an emergency. What was my next move? Should I seem not to understand what she had said? And if I didn't understand, should I let it pass, or should I go back out there and ask her to explain it? Should I deny that I ever "dressed up" in those clothes? I couldn't, because I didn't know how she knew. Maybe somehow she'd seen me and there was no way I could lie about it. Here was my worst nightmare come true a second time, my ultimate humiliation known at the office as well as at home. And it meant nothing at all to her.
I decided to take my cue from her, and without confessing anything to ask her about her brother, as if none of this was a big deal or even a little one. I waited until I heard her come back, and a little apprehensive, I stood up and started over toward her reception area. Somehow I felt that my life was about to change. It was a little exciting. I told myself to calm down.
Jack and Jill
by Vickie Tern
®FF6¯ I stood in the doorway. "Darlene, would you come into my office for a moment," I asked. She picked up her Steno book and headed toward me, with a questioning look when she saw I was a little distracted. I shut the door as she came in and she looked even more puzzled—the outer office was empty, shut the door against who? Then I went back behind my desk and sat down, and she settled into her usual chair when taking dictation, and I folded my hands on the desk and leaned forward, trying to look only casually concerned. "Um, uh, you know ...," I began, "Ah, tell me about your brother."
She looked alarmed. "Why, is he in trouble again? He promised my mother that he wouldn't...."
"No, no," I broke in. "I'm sure he's fine. I mean, tell me about his putting on women's...er...clothing. Didn't you say he did that."
Darlene looked relieved. "Why yes, he did. He does, I mean. I mean he's a woman now, so why shouldn't he? She!"
I was bewildered. "Your brother is a woman?"
"Why yes," she was puzzled I should ask. "Hormones and operations and everything." Light dawned in her eyes. "That's how he had a place to put a tampon," she said helpfully. "Or she has a place to put one, now. But when she was still my brother and not my sister, he would put one in his other place anyhow just so he could feel more comfortable when he wore his women's things. That's why I thought maybe you did too." Darlene obviously thought she had now cleared up all the mysteries.
"Uh, Darlene," I said, looking out the window as if not much interested in my next question or her answer to it, "Why do you think those are my clothes in the ... uh...coffee room?"
"Why, aren't they? Your wife is going to miss them if they're not. Why else do you keep them here? Why not just give them away if they're hers and she doesn't want them? Besides," she said, and she smiled reminiscently, "they fit you beautifully. You look darling in some of them."
"You've seen me wearing those...uh...clothes, Darlene?" I asked in the gentlest and steadiest voice I could manage, though I was now beginning to feel, well, strange.
"O yes," her enthusiasm picked up. "A few times I'd come by the office on the weekend to pick up something, and there you were in your office, or looking at yourself in the mirrors in the reception area, wearing the sweetest things. You looked just dear. Well, you never noticed, and you were so busy I thought I shouldn't disturb you, so I didn't." She looked thoughtful and a bit troubled now. "I've also seen you change into panties and bras and things in the morning, when you got in before me. But I get in pretty early. Tell me," she continued, "I've always been curious. Why don't you put your panties and underthings on at home before you come in? Don't you wake up in time?"
I decided that only the truth would serve. This whole conversation was already touched by lunacy. I needed to keep it real. "My wife doesn't like to see me wearing women's clothes, Darlene." I tried to suppress a note of sadness. "She told me to take them out of the house. That's why I brought them here. That's why I get dressed in them here."
"Oh," Darlene said. She seemed satisfied with my answer, as if my wife was peculiar but entitled to her own inexplicable likes and dislikes same as everyone else. "You know," she said, still thoughtful, "this office isn't really a good place for dressing and undressing. And it's really no place at all for putting on makeup, if you're starting from scratch, because you can't clean up properly afterward. You use way too much kleenex. Sometimes on Monday morning the wastebaskets are all full."
My God! The wastebaskets! I used them without thinking!
Darlene gathered up her Steno pad and pencil, and gathered herself to stand up. "Would you mind if I suggested something?" she asked. She saw I was looking at her, mildly curious. "Why don't you bring all those boxes to my place? You could get dressed and undressed there all you want. I wouldn't mind. You wouldn't be in the way. I have an extra bedroom you can use to get dressed. I even have an extra dressing table where you can keep your makeup. It would be a lot easier for you, wouldn't it?" She waited for a reply.
"Yes, it would," I said.
"Then let me know when you'd like to bring them over. I'll clear the extra room and that can be yours." She giggled. "Not to sleep in of course. I don't think your wife would like that."
"No," I said. But Darlene was already out the door and back at her desk. I didn't know what I was saying "No" to, but it didn't seem to matter. Nobody was listening. I seemed to have said "Yes" to everything.
That evening when Darlene was leaving she stopped at the door to my office to let me know, as she always did. I thought I should say something that would show that her boss was grateful to her, and interested in her well-being. "Uh, Darlene," I said, "Uh, did you ever find a tampon?"
"Oh yes," she replied, smiling broadly. She had a terrific smile, but usually she felt too distracted to unleash it on me. Not now. I got both barrels, and felt staggered. Darlene didn't have smarts, but she had it where it mattered. And she was gorgeous! "Vera had some spares. Now I'm keeping a box in my desk, just in case. Let me know if you ever need any."
I still don't know what she meant by that last offer. Maybe nothing. But a week later I moved in with her, or my clothes did. She gave me her spare room, with its walk-in closet, and I hung everything up, and put everything in two dressers, and laid out my makeup on her extra dressing table, and got a spare key from her, and went home to fix dinner for Jill. It was my night to fix dinner. I felt wonderfully cheerful, and a little bit guilty, because I was setting up with another woman to violate an implicit understanding with my wife. But I wasn't violating the letter of the law Jill had laid down. I had never promised Jill I'd abstain from wearing my beloved women's clothes, and this arrangement with Darlene was all really very innocent. Jill ate without a word, then went in to watch the nightly news on TV. For once I didn't feel snubbed.
We settled into a routine over the next few months, Darlene and I. On weekdays I stopped by her place on my way to the office, and put on my brassiere and panties, or maybe pantyhose, or a girdle, or a slip, and then my regular shirt and tie if I was meeting a client, or an open necked shirt if I was just planning to work at the ofice, and then we'd drive in to work together. At the end of the day I'd drive her home and change back. On whatever day I told Jill I was heading for the office, Saturday or Sunday, or sometimes both, I'd go to Darlene's place and dress up in whatever felt right—a mini, or a long skirt and blouse, or a cocktail dress, and do my face and my hair, and then I'd lounge around and watch television, or fix some sandwiches for lunch, or read, or work on some client's problem, and imagine I was a lady doing all of these things, and feel very good about it. Darlene never bothered me. She slept late on weekends, for one thing. When she woke up she'd head drowsily into the kitchen, and if I was there I'd have a fresh pot of coffee ready for her. If she liked whatever I was wearing she'd compliment me on it, and sometimes make suggestions, or chat about her own wardrobe, or about similar tastes among her friends, and without ever discussing anything other than the most superficial things we got to feel quite friendly, even intimate. I felt accepted for what I was. We were like girlfriends gossiping at breakfast. When Darlene would head off to shower and dress and set out for her own day's activities, I'd feel very good about her, and very grateful. .
Which may be why I made the first of several mistakes. One morning when I was driving Darlene to work she turned suddenly toward me and said, "You know, I think you'd be prettier if your hair were a little brighter. I don't mean blonde or anything, but maybe some sun streaks. And have you ever thought about getting a perm? When you set it in rollers it would have much more body if you had a good perm down under to begin with."
I reminded Darlene that I was not free to change my hair into a specifically feminine style or color, because my wife would notice. And besides, since I was a man, many things that made women beautiful weren't appropriate for me.
This notion puzzled Darlene. "That's not true. Sun streaks look natural. And with your shape of face, wearing your hair a little fuller on the sides would be, kind of, nicer. Even sexier. Better groomed, like Faye Dunaway. Especially now that you're letting it grow out. I'll show you next weekend."
I don't know what possessed me, maybe the idea that Darlene could make me look like Faye Dunaway, but the next Sunday I was sitting in a chair with a sheet tucked and pinned around my neck while Darlene snipped and primped and toned my hair with scissors and combs and brushes and swabs, until by early afternoon she was done. She took out the rollers and combed me out, and I was gorgeous! My hair had never looked so full, and soft, and lustrous. I was delighted, really rapturous, and when Darlene finally released me so I could stand up I turned and took her by the shoulders and planted a kiss full on her lips. "You were right, Darlene! This is really beautiful! I love it!" And while I looked at my new hairdo my fingers moved up to soften a wave here and to tuck in a curl there. The gesture was instinctively feminine, I recognized at once, and I was all the more delighted by what Darlene had done.
Darlene turned soft in response, no longer matter-of-fact but strangely quiet. "Jack" she said, looking me over closely. "There's one more thing that needs to be done. Why don't you sit down again, and I'll take care of it for you."
I sat down again, and Darlene put some manicure scissors and tweezers within easy reach on a table just behind me. "Now that your hair is curved so beautiful," she said, "your eyebrows need to be shaped a little better. Your bangs don't cover them any more. Just hold still."
And to my astonishment she straddled my lap and sat down on it facing me, her legs spread wide and gripping mine on either side, her crotch rubbing directly on mine, her breasts just under my nose, her beautiful eyes studiously serious as she stared intently at my eyebrows, not quite looking into my eyes. "I think a higher arch would be more beautiful," she said. And as she reached for the tweezers behind me she tightened the grip of her thighs on mine and lifted her whole body up and forward in a single motion. Her breasts brushed my face. I should point out that we were both wearing only bras and slips, so as not to get hair clippings on our dresses. I meant to pull on some pantyhose when I finished dressing, and knowing I'd be covered by a sheet while Darlene did my hair I hadn't bothered to pull on panties. Now, with Darlene posting on my lap like a circus equestrienne riding a stallion bareback, I could feel from the heat and moisture between her legs that she also wore no panties.
In a state of shock I sat very still, and like an overgrown child she twisted back, tweezed, lifted her elbow and twisted forward, tweezed, wriggled her delicious fanny on my crotch, and tweezed yet again. Needless to say, beneath my slip I had a raging boner pressing directly into the opening of her pussy. She seemed not to notice as she studied the sculpting of slightly higher arches onto my eyebrows, and tweezed, and trimmed some of my longer eyebrow hairs with the manicure scissors, and tweezed, and finally posted herself up off my crotch again with a single squeeze of her powerful thighs, to place her instruments back on the table behind me. I didn't dare move. "There, it's done!" she said with a satisfied nod of her head. And still holding herself up, with a single swift movement of one hand she lifted the hem of my slip beneath her to my waist, and then settled herself down onto my stiff prick, now tucked deep inside her.
"Oh God!" I said.
"You really are beautiful now!" she said in reply. And as I had done with her a few minutes earlier she rested her hands on my shoulders, leaned slightly forward, and kissed me full on the lips. Then she sat back with my cock imprisoned inside her pussy by the full weight of her body, and said with a satisfied smile, "Mission accomplished!"
That day we paid no more attention to my coiffure. I buried my face in her abundant, perfumed breasts, and with both hands stroked her back and sides along her satin slip, and looked up at her face to see that she was looking down at me, her eyes half-closed, hooded under their lids, her lips apart and still slightly smiling. I rocked my pelvis slightly as if to seat myself deeper inside her, and felt the base of my prick snug up tight against her. She was deliciously wet and warm, and I as I rocked back down again she lifted herself up with a squeeze of her thighs, and I slid along inside her in an excruciatingly slow progress until my tip was nearly released by her pussy lips. Then we reversed direction again, also slowly. Whatever her horsemanship, she rode me superbly, slowly spurring me from a walk to a trot to a canter to a full gallop in which we were each shrieking, bound violently together in a single rhythm, each unaware that the other was making a sound, both of us out of our minds. Finally I exploded, and spent what seemed buckets inside her, while she crushed my face into her chest and arched her own face back, toward the ceiling, screaming "AaaaaaHHHHH!" with her eyes tight shut, her pussy squeezing and squeezing me over and over in spasms out of control, until finally we both subsided and collapsed onto each other, dripping with sweat.
As I softened I began to leak out of her onto my crotch, but she made no move to dismount. The afterglow went on, and we sat quietly in each others' arms. Finally she opened her eyes and looked at me and said, "That was very nice. Do you think your wife will mind?"
"What do you mean?" I asked, stalling for time and in fact wondering why she felt she should ask that question.
"I mean, your having sex with a lesbian. Doesn't that make her one in a way too, all three of us being women?"
I was baffled, but tried not to let on. "Darlene, you're a lesbian?"
"Why yes, Jack, I thought you knew. Some boys I know are friends, but I don't have any boyfriends. To really enjoy myself I have girlfriends. Always. Ever since I can remember." She hugged me, rather sweetly. "Now you're my favorite girlfriend. You're very nice. You don't even need a rubber penis the way my other girlfriends do."
"No, I guess I don't." We were back in Darlene's own world. I tried a new tack. "Uh, Darlene, you do know that I'm not really a woman."
"Well, yes, I guess so, in a way. But you're so much like my brother, and he loved to pretend he was a woman, and it turned out he wasn't pretending. And you love to pretend that you're a woman. And now look at you."
"Well, I can't look at me, exactly," I said.
"Here," Darlene said. She reached over my shoulders again to the little table behind me and picked up a hand mirror lying there, and leaned back to show me my face reflected in it. My heart rose up and sank down, in both directions together it felt like. There over each of my mascaraed eyes was a thin, high, aristocratic arch of an eyebrow in such a delicately feminine curve that I felt a new erection begin just from looking at them. At the same time I realized that there was no way for me to disguise those fine traceries over each eye so they would look masculine when I got home. With my hair teased out to frame my cheeks and my eyebrows plucked I had a woman's face.
"Oh, God!" I said again.
"Jack," Darlene said. "What's your real name?"
"I want to call you by your girl name. I'd feel better about what we're doing. Don't you have one?"
"Yes, I do Darlene. Ever since I was a little kid, and got hooked by my first bra, I've liked to think that a girl named Jane lives inside me and is using me to dress herself. I'm Jane."
"That's so nice. Jane. Does your wife ever make love to Jane?"
"No, Darlene. No way."
"Well, then," Darlene said. "I guess there's no problem."
Again I didn't ask her what she meant. I guess I didn't want to know. She sighed and snuggled down onto me again, and I began to grow harder under her, and soon I was inside her again.
Well, the rest of that afternoon, and early into the evening, I never did finish getting dressed. Darlene and I made love. When we were exhausted by our second session with Darlene astride my lap, she suggested that we go to bed together and make love properly. This time I understood her. "You mean like girlfriends," I suggested, and she agreed. By this time my pecker was slack, and I was willing to try anything that didn't require a hard on. It turns out that's what Darlene had in mind too. First she ran a tub, perfumed, and we both slipped in giggling, glued to each other. We fondled and stroked each other's slick bodies, and Darlene's fingers found my asshole under water, tracing the clamped, puckered opening. We began to grow passionate, stood up, and dried each other off slowly, exquisitely slowly. Then we each of us fixed our hair and put on our makeup carefully, each of us anxious to look pretty for the other. I slipped into my most delicate nightgown—one I'd never worn to bed before, because I'd never been able to wear a nightgown at night. Then once we were snug together, lying on our sides, facing each other and smiling, the world turned radiant. Our hands reached out to each others' bodies, and we looked into each others' eyes, and smiled, and caressed each other, and closed our eyes only to moan softly, and then open them again. I touched Darlene's nipples and she reached for my penis, and we softly fondled each other, until we each came yet again! Then we reached even greater intimacy with out mouths and fingers.
Darlene and I tried anything and everything, one after another, and everything we did was wonderful. The key to Darlene's enjoyment of her lesbian relationship with me was gentleness. Her mouth was soft, and her tongue, and so was mine as we tasted and teased and tickled each other, and licked, and kissed, and sucked, and probed. I went down on her in an act of loving devotion, and sucked and tongued her as sweetly as I knew how, and she bent over my soft dildo clit, as she called it, and licked and stroked it with her lips. When it was time for me to leave, just after dark, when my plucked eyebrows might go unnoticed, Darlene and I hugged each other goodbye with respect and affection and gratitude and appreciation.
But not with love. We two girls, as Darlene thought of us, were having fun being girls together. For Darlene it was no more complicated than that. On Monday when I stopped in as usual to change to my bra and panties and take Darlene to work, her only conversation, as always in the car, had to do with a sitcom on TV. On Saturday we were passionate girlfriends again, and I was in heaven. Darlene seemed altogether content that I was the girl with the dildo, though she was sometimes concerned that I kissed and licked her pussy and also fucked it, while she couldn't exactly reciprocate in kind with me, and had to settle for kissing and licking my dildo clit or my anal opening. Another time she asked me why I got nervous whenever she suggested we go out, maybe, for dinner and a movie. I told her my hips were already too heavy, and I was trying to lose weight. She thought I was slim enough, but understood how a girl feels about her figure.
There was no problem when I got home that first night. Jill was already asleep, and the next morning when I woke I could hear she she was finishing her coffee and heading out the door. I headed for the bathroom, and saw I was fortunate she hadn't seen me. My hair was beautifully puffed out, with large stray curls tumbling here and there and falling behind my ears, and my brows were plucked delicately high, amused, inquiring, slightly surprised, slightly disdainful, unmistakeably dainty and feminine. I realized I had no makeup to cover them with, not even an eyebrow pencil, and decided that today I had better find a theatrical specialty store before Jill got home. At least glued-on male eyebrows weren't on her list of proscribed contraband.
When I took a shower I discovered another problem. Darlene had given me a "Body-Perm", a light permanent wave to help form and hold the large curls of hair she thought my face required. When those curls were set with large rollers, each hair lay neatly against the next. But now, stepping out of the shower, I saw my wet hair was sinuously waved, hanging down in cascading ringlets. It didn't straighten when it dried, and I thought I was going to have to pay the ultimate penalty for my indulgence of Darlene, and get the permed part cut off. But I wet it again, and a blow-dryer and careful brushing brought it to an approximation of its former appearance. Close enough, anyhow. I would have to be careful never to let Jill see me with my hair wet.
I found just the right hairpieces for my eyebrows, and attached them with spirit gum, trimmed them back, and decided they would do. That night was my turn to cook. I brought home prepared food from the supermarket, heated it, and served it. I realized then that I was safe enough. She never seemed to bother to look at me as she ate, and when she got up from the table I noticed she looked away, as if I were still some kind of embarrassment to her.
But there were things for her to notice without my knowing it, I realized later. My bubble baths with Darlene left a faint perfume on my skin, and then on my bedsheets, and it was three or four weeks before I noticed. I began drowning the scent with an aftershave, and Jill commented on my peculiar, sudden dedication to perfumed smells, hardly ever used earlier. My stage eyebrows were a problem when I slept. Once she found one near the kitchen doorway and called me. I immediately declared it a caterpillar, and stomped on it before scooping it out of her sight. But first I instinctively felt to see if one was missing from my brow, and she may have noticed that off gesture.
Once, Darlene mentioned offhand that Jill sometimes called my office on weekends when I was supposed to be working there, and getting no answer left a message on Voicemail. I checked each week after that, and found that more often that not Jill was indeed checking up on me. Thereafter I called the Voicemail service from Darlene's house every few hours, each week. If there was a message from Jill I immediately called her back with a variety of excuses why I hadn't picked up the first time.
But what really set Jill on the trail of her errant husband was the oldest of all evidences of infidelities, lipstick on a shirt collar. That it was my lipstick, from pulling on my shirt over my head before I removed my makeup, didn't matter at all. If she had confronted me with it, I might finally have gone on the attack, and asked her angrily what a man with a frigid and sullen wife and a compulsion to crossdress should be expected to do. I had already begun fantasying myself married to Darlene, becoming her mindless girlfriend for life, and the sexual advantages didn't seem that bad seeing that Jill and I were no longer companionable in any other ways. My life might have been different, if I'd done that. But Jill may have sensed this, because she found the shirt in the laundry and still she said nothing.
Months went by. All those months of blissfully transgressive, transgendered heaven may be more than anyone deserves, but I had that much happiness as Darlene's in-house girl friend. I'll always have it. I'll never forget it. But it ended.
One Friday afternoon Darlene's concept of me collided with Jill's. Darlene called home when I was out, and got our phone answerer, and left a business message for me. Then she called back and left a message for Jane apologizing that she had borrowed one of my dresses and stained it, and was very sorry, but it was ready at the cleaners if I wanted to pick it up on the way over tomorrow, and she'd lend me one of hers any time in repayment, she thinks she has a few that would fit with just a little less padding in my brassiere. Then she phoned again, and left a message for Jack to be sure to erase that message for Jane, because she shouldn't have left it on Jack's answerer. Jill picked up all three of these messages from her office, I learned later, then left them for me to hear when I got home. I erased them in a panic. But Jill seemed no different that evening, so I relaxed.
The next morning I was at Darlene's, my hair piled high and curly on my head, wearing long dangly earrings because Darlene loved to feel them between her legs, and they were clipons so there was no danger they might tear my earlobes if she squeezed her thighs too tight, and I was also wearing the sweetest little Teddy, with my lipstick smudged from nibbling on Darlene's nipples, and with Darlene's lipstick smudged all over my face, when the doorbell chimed and then, because Darlene had left the door unlocked for me, Jill walked in. She didn't say a word. She looked at me and lifted a camera, and flashed a picture of me, and then another, and then one of Darlene, and then she walked to a corner of the room and took one of the two of us together, and then another, and then she went back out through the door and closed it behind her.
Darlene and I looked at each other. I knew she would say something silly, wondering whether her hair was combed nicely for those pictures, or wondering what they were for, or why Jill didn't stay for coffee, so I just went over and held Darlene, and hugged her, and kissed her, and looked at her tenderly, and kissed her again. It was very sad. It was over.
Jack and Jill
by Vickie Tern
Jill never did say anything about her discovery of my little tryst with Darlene, and I never saw those pictures she took either, and she never referred to them again. She didn't have to. I knew she would use them ruthlessly any time it suited her purposes. She knew what I most feared about my crossdressing was exposure, and she knew I knew she knew, so nothing needed to be said. I spent that night in a motel, and spent Sunday at the office hoping for a phone call and dreading one if it came, though none did. Again at the motel Sunday night, and again at the office on Monday, with only business calls. Darlene, miraculously, had worked out that I wasn't going to be stopping by her place to change my underthings any more, nor to drive her to work, but she was otherwise her usual sweet, simple self, untouched by my domestic catastrophe.
For a few more months after Jill discovered me with Darlene nothing happened. Oh things changed at home all right. On Monday I came home from work feeling seedy from too many days in the same clothes, and found our bedroom door had a new lock on it—now it was her bedroom door. Without forcing the issue, that night I slept once again in the spare bedroom. A day later I asked her to let me in long enough to get my suits and shirts and socks out, and she shouted furiously "No! Wear your dresses, you freak!." It seemed better not to ask a second time, so I bought a few new men's jackets and pants and things, just enough to get by until things took shape or settled back down. Meanwhile Darlene gave notice that she was leaving town to work for another company, and had enjoyed working for me, and had enjoyed getting to know Jane, and that I should collect my things from her place. So I did. I couldn't bring myself to throw them out but I certainly couldn't start wearing them again either. So I boxed them and put them into the garage. Time passed.
Jill had nothing to say to me. We lived like strangers bedded down in the same motel, each without knowledge of the other. I tried starting up conversations and she stared at me impassively. I cooked a terrific dinner one evening, and the smells saturated the house by the time she got home, but when I asked her when I should serve it she just said "Whenever you want—I'm going out!" Then she went out. I came home once to the smell of something cooking, went eagerly into the kitchen, and found only empty pans in the sink—Jill had prepared and eaten her own dinner, then left for the evening. Soon we were both eating most of our meals out, me by myself, Jill with different women friends in different restaurants, I learned from time to time through the grapevine, and I wondered what that grapevine might not be telling me.
I wondered especially what she was telling her friends, and what they were telling her. When I called a few, they seemed to know no more than that I'd hurt Jill terribly and that no apology could possibly make amends, at best only time could heal things. One asked if I had hit her, and when I replied "No, nothing like that, I couldn't do that" she just replied "No, I didn't think so, you're such a wuss." I took due note that I'd lost that round either way. They all advised me that the storm would pass, to wait it out .
We did see each other at breakfast. Then Jill often looked directly at me, as if I were some kind of problem she'd have to get around to fixing one of these days, or couldn't quite figure how to fix yet. I usually avoided looking at her. Plainly she didn't yet know what she wanted to do, and didn't want to feel rushed into any decisions, and I took that as a good sign. After maybe ten or twelve weeks of this silent treatment, one evening we found we were sharing the living room as if we were together instead of each of us home alone, and I asked her if we could talk. She just said, "If you want, I won't stop you." So I took a deep breath, and with my life hanging on it I began.
I told her I was devastated, and would do nearly anything if we could resume our marriage. I told her that my crossdressing was harmless in itself, and a compulsion I couldn't resist. I pointed out that in a sense her absolute prohibition of it at home had forced me to the office and then into the arms of that bimbo. I told her I wasn't doing it now, but that sooner or later I was bound to resume it, I had purged and binged too many times not to know that. I begged her forgiveness. I offered to absorb any revenge or punishment she wanted to inflict upon me, and to meet any conditions she might set if only she would end her long silence. Any. I told her I loved her. I told her I was terribly sorry for having been unfaithful to her. I went down on my knees, and I started to cry.
She listened to all this with her face expressionless, looking at me the whole time. Then when I was on the floor sobbing, apparently done, she said merely, "I heard you. I'll let you know." Then she turned back to the book in her lap and dismissed my existence.
Two days leter we met at breakfast, and just before she left for work, already wearing her coat and with her briefcase in hand, she paused at the kitchen door and said, "Are you ready to listen?" I nodded, speechless. "Ok," she said, "I've thought about this. I've talked to a lot of people about it, and I've gotten advice, and I've looked at a lot of options, and I've worked out what I want for me, and what I want for you, and what I want for us, and I know now that there is a way we can both of us have what we want, even if it isn't what we thought we wanted. It's the only way, and I'm not going to tell you what it is. What I'm telling you now is what I want for you now. That's all that concerns you, and that's all you're going to hear." I nodded again, still afraid to say a word.
She went on. "You're right in one respect. When I forbid you to wear women's clothing around me I was asking too much from you. You can't help it. It's like an addiction you're born with, and you can't be blamed for that. I thought I was marrying one kind of man, and I found I'd married another. It disgusts me to see my own husband parading around thinking he looks like a woman, but I can control my disgust, and I can change the way I feel about your...addiction. I know how to do that, now. And I will. I'm going to let you dress like a princess or like a whore at home, again, since you must. But only when it suits my purposes. And my purposes are mine."
"But nothing drove you to have an affair with that floosie. You violated our marriage with her. You gave in to easy temptation, and for that you owe me, and owe me dear, and for that you're going to pay me. Don't assume you're forgiven, or that there aren't punishments in store. I have plans for you. You have a way to go, and you're only just beginning. You said you'd do anything and agree to anything if I'd resume with you, and I mean to hold you to it. Anything."
I nodded, afraid to hear what she was going to say next, but eager to hear it.
"From now on you do not put on women's clothes, or makeup, or airs,
unless I tell you you can. It may be a week, or a month, or six months before I tell you you can do it, but you will control yourself. Trust me, the time will come. But you'll do it when I say so, not when you want to. If it happens that when I say you can, you don't feel like it any longer, I won't complain. Then we can be together again the way we were, or the way I thought we were, maybe. But that's too much to hope for. From now on, you will be a woman when I tell you to be a woman, and only when I tell you. Is that clear?"
I nodded again, a slowly rising joy beginning to replace my fears. In a way this sounded like a fulfillment of my wildest fantasy, that my wife might participate with me, and guide me, even order me to dress up. What she then said confirmed it.
"When you next want to be a woman, and I want you to be one, you will do what I tell you. I will make suggestions about what to wear and how, and what's suitable and what isn't, and what I want you to do when you're dressed, and where I think you fall short. You may think that being female is a game. I don't. If you're going to do it, you are going to do it right. Any time I suggest anything, you will cancel any notions you may have concocted for yourself, and you will agree with me, and you will be happy that you agree with me, and you will thank your lucky stars that you agree with me, because I'm right and you're not. My suggestions are absolute commands as far as you're concerned. And you will never hesitate to think of them that way, no matter how odd any of them may sound to you. Is that clear? "
I nodded, my eyes beginning to fill.
"There are some real obstacles ahead for you, and I'm going to enjoy watching you trying to deal with them. You said you'd meet any conditions and I mean to hold you to that promise. Now do you agree to everything I've said? Absolutely, unconditionally, nothing held back?"
I nodded. For some reason I was feeling a small stirring in my loins, listening to her speak of hidden plans for me.
"Then here's the key to our bedroom. That cheap sport jacket you've been wearing to work for the past month is a joke. Put on something that looks decent. The Harris Tweed is nice."
I nodded, not believing my ears. My exile from our bedroom was over?
But not quite. Not just yet. "Take the rest of your men's clothes into your room. You aren't going to wear any other kinds of clothes for the time being, so you might as well wear decent ones. Then lock the bedroom again and leave the key for me on the front hall table. I may be in late again tonight."
I heard her.
"And those women's clothes you've got packed up in the garage. Bring them into your room too. I'll want to look them over some time, to see what we've got to work with."
I heard her.
"And let your lease at your office expire. You are through working, for now. Maybe for good. Pass your clients on to someone else. I want you where I know you are twenty-four hours a day. I'll be the breadwinner who goes to work in the morning, and you can be the housewife who takes care of the house. I'll have full charge of the money and you'll have full charge of household matters." She looked sly for a moment. "Maybe some day I'll let you be the housewife who looks pretty for me when I come home from work, but don't get your hopes up."
There was a lump in my throat. I just stared at her and nodded.
"And dear, you remember that dinner you cooked up a couple of months ago when you were feeling guilty, and you hoped you could buy me off or that I'd let you off easy, and you found I wanted no part of you? I can tell you now that it smelled delicious. If you can fix it again for tomorrow evening, I'll pick up a decent wine to go with it, and I think we can begin to enjoy being with each other again. I do still love you, and there are many things about you I admire. But don't think for a moment that this is going to be easy for you."
And with that last remark she disappeared through the door and was gone.
More weeks went by, and we gradually resumed our old relationship, except that I was still locked out of our bedroom, and some nights she went out without a word to me, and I didn't dare ask her where when she came back, not too late usually, maybe by midnight or a little later. I no longer dressed up, and she said nothing more about it. I would stand wistfully in front of my closetful of pretty things, looking at them not daring to touch them. One day she told me that I could set out my cosmetics on my dressing table, but not use any, so I did, no questions asked. Then another week passed with nothing more said.
One evening she laid out a new arrangement for us. She told me she was giving me a green light for whatever I wanted to wear, women's clothes or men's, but with an absolute condition I must obey absolutely. It was this. In any one 24 hour period, from eight a.m. to eight a.m. the following morning, I could wear the clothing appropriate to either gender, either male or female, whichever I chose. Whatever gender I was imitating when she left the house just after eight each day, she said, was my gender for the day and for the evening. If I was in a peignoir for breakfast and I had to go shopping that day, then I would wear a dress to go shopping or I wouldn't go shopping at all. If she left me in men's pants, she wanted to see me in pants when she returned—not necessarily the same ones, of course. If we were going out together to visit friends that night, I had better know it when I woke up that morning, because at eight a. m. we would both know what kinds of clothes I would be wearing that night. So I had better begin planning ahead. Unisex clothes were out, she said. I would have to choose who I was, each day, Jack or Jane. And then hope the house didn't catch fire, to force me into the street wearing a minidress or a tutu.
I thought this was just wonderful, and it was! The first morning I woke early and bathed and slipped on my prettiest silk dress, and did my hair, and made myself up carefully, and went down to prepare breakfast for the two of us. I was so excited! I primped and fussed, and when Jill came down I couldn't quite contain my shy pleasure. She looked me over.
"Not bad," she said, amused at my eager modesty. "Maybe you'll be worth the trouble. Are you going somewhere after I leave for work?"
"Oh, no," I reassured her hastily. "Not in a dress. I wouldn't dare."
"No, I suppose not," said Jill. "But aren't you a little overdressed for just breakfast when you aren't going anywhere?"
"I wanted to look nice," I said, a little disappointed in her reaction. "For you."
"For me," she replied. "Well, I suppose you need to express your feminine side, as you say. But try to dress appropriately. That dress is more suitable for tonight, for dinner. Are we eating out?"
I knew she was teasing me, or maybe needling me, and said nothing.
"Jack," she said, "Or, Jane, since today you're Jane. Something else. That dress does a lot for your figure, but you have to help it. You have no waistline. You look too chunky, too much like a man in a dress, or like some middle-aged woman who's let herself go. You need to nip in at the waist, at least a little. For now, from now on you're on a diet. Toast and black coffee for breakfast, a small cottage cheese salad for lunch, no more, starve yourself all day, and eat half of whatever you were planning to serve yourself for dinner. Decide on a regimen and stick with it. From now on. Whether you're dressing as a man or a woman. The discipline will be good for you. Go hungry all day." She paused. "And anyhow, you obviously like to shop. I want you into size 14 by the end of next month, and when you reach size 12 I'll let you replace your wardrobe. Not until then. Understood?"
I understood. She wanted moment by moment control over me, and any time I felt like snacking during the day, she wanted me to be reminded that she was in control and I had better not. I nodded.
Mostly, when I knew I could stay at home all day and evening I fixed breakfast for her in a blouse and denim skirt or the like, looking as neat as I could, with just a touch of eye makeup and wearing a subdued shade of lipstick, and my hair done simply. Jill would come down, glance at me, say nothing, comment on the weather, or the morning headline, or ask my plans while she was having breakfast, and then leave for work. She never seemed to notice what I was wearing, or how I looked. At dinner time when she came home from work I was happy to greet her in an afternoon dress, or a coctail dress, or if we were having something special that night, with candlelight, I would put on a long gown and more dramatic makeup and put my hair up for her. I was still dressing for my own satisfaction, of course, but more and more I was dressing for her. I wanted her to admire me, to want me, to love me. But Jill never seemed to notice. She would praise my dinners, and admire the canlelight. But she seemed stone blind to my appearance.
I finally became a size twelve, and began buying new things. But always as a man. I became a familiar figure in stores all over the city and suburbs, buying dresses and lingerie "for my wife" as if she were too feeble to shop for herself. I don't know who I fooled. Some saleswomen would tease me, I realized later, by asking me friendly ambiguous questions like, "Are these for your pleasure or hers" while wrapping and charging some intimate items. I was too embarrassed to pick up on their comments and kid back with them. But for a while, when Jill saw me wearing men's clothes at breakfast she could assume accurately that looking male was not uppermost on my mind.
Twice I had a problem. Once I forgot we were expected for dinner at an friend's house and I began the day in a housedress. When Jill saw me, she said simply, "Is tonight's dinner party the place where, finally, you mean to show the world that you're a transvestite? Or do you think you can pass as a woman when we're expected to show up as a couple? Be sure you have a dinner gown that won't disgrace us in your closet, or you'll have to shop for one this afternoon. I don't think you own anything appropriate at the moment, and I'm certainly not lending you anything of mine." I spent the day hiding in the house terrified, wondering what was the least painful way I could injure myself badly enough to decline the dinner invitation. I was bailed out only by the dinner's last-minute cancellation, because the host had the mumps! Jill noticed that I was a wreck when she got home. I told her about my utter terror at being found out, and what I had been prepared to do to myself. She merely smiled a little grimly and said nothing.
Another time I was wearing skin-tight jeans and a T-shirt tight enough to show my bra and my breastforms when I saw we had run out of charcoal for the barbecued chicken Jill knew I'd planned. Without thinking I left the house dressed as I was and got into the car, and was halfway there before I realized I couldn't pass as either a man or a woman. So I drove further, to a place a half-hour out of town that sold bags of charcoal, sneaked to a far corner, hugged a bag of charcoal to my chest, threw some dollars at a puzzled employee, and fled back to my car. A day later, wearing men's clothes, I bought an oversized woman's sweatshirt to wear if that should ever happen again. Jill allowed that it was not a unisex sweatshirt, because it had small flowers all over it, and said she'd like to see me go out some time at least wearing flowers, if I had the guts. She was only mildly amused when I told her how I had bought the charcoal while my bra was visible. She then asked if I had ever bought myself a topcoat of some kind, and a purse, for when I meant to go out, and I answered "No, what for?" She merely smiled.
Now and then she would make a suggestion, and I took them as commands. Very early on she told me to let my hair grow out, for example, and she showed me how to use a barrette to hold it back when I was in femme mode. She asked me to practice a "lady voice," and then insisted I use it on all appropriate days—which as it turned out, meant most days. She corrected my occasional lapses of taste, my wearing at the same time two different patterned prints with clashing colors, and I tuned my eye accordingly. Once she told me to do something about my nails, so I went to a unisex salon and had them trimmed, and shaped, and given two coats of clear gloss. Another time she told me to pluck back my eyebrows, "the way they were when you were carrying on with Darlene." I said I thought she hadn't noticed, and she gave me a contemptuous glance and turned away. I was very uneasy the first few times I went out with thin brows arched high over my face, but no one seemed to notice, and after a while I began pencilling their shape even higher on days when I was Jane. When I was in femme mode she insisted I walk, move, and sit like a lady, and after a while her constant correction of me became occasional, and finally unnecessary. In fact, when I sometimes made some effeminate gesture while in male clothes, she'd call my attention to it with sarcastic comments like "Do that again. Your boyfriends will love it."
Then one Friday late afternoon I was vacuuming in the living room when Jill came home a bit early, glanced to see that I was wearing a short cotton skirt and halter top, and went into the kitchen. When I put away the vacuum I saw that she was setting the dining room table for three, using our good silver and good set of dishes. A terrible fright struck the pit of my stomach. I clasped my hands behind me to stop them from shaking.
"What's up?" I asked her in my feminine voice. "Is someone coming for dinner tonight?"
"Yes dear. We have a new Associate at the office, unmarried, not yet settled into town, still living in a motel as a matter of fact. He's been eating out all this time, and he tells me no one has invited him yet for dinner or to meet people. I'd like you to put on your prettiest dress and look especially nice tonight for him."
To be dressed like a woman in front of a stranger! I was petrified! "Jill," I said, "No! I'd feel humiliated. I couldn't possibly. And besides, ...."
Jill cut me off. "Jane," she said stenly, "That's who you are today, Jane. That was your choice this morning. You are already humiliated, in my eyes, and those are the only eyes you need to worry about. You've been making a big deal over your so-called compulsion to dress like a girl. It has almost cost us our marriage. It cost you your dignity and your honor, and it led you to violate your marriage vows, and it cost me my trust in you. Now I'm allowing it, right? You haven't heard a peep from me when I come home night after night and find you're wearing a peignoir, or a silk dress, or a tailored suit, with your hair up in rollers or your face all tarted up. For you it's been a delightful game, titillating and safe! You never dare to go out and risk being seen. You're so afraid of discovery you've never asked me to go out with you to cover for you."
I started to protest I'd never dare ask her, but she cut me off. "Well, now's the time for you to take a nice, safe risk. Stay at home and be a lady and enjoy our dinner guest in your own home."
I felt a little scathed by this argument. She was right. She'd paid most of the cost of my crossdressing until now. "But what if he reads me? What if he comes expecting to see your husband, and sees a husband in drag?"
She dismissed it. "He won't," she said. "I told him my husband was out of town, and that I was having a dear friend over for dinner, and that he'd be welcome to join us, and that maybe he'd like to meet her. That's who he'll see. My dear friend Jane. Let's see if you can pass at least in your own home, this place where you've minced and pranced around hundreds of times. Let's see if you can manage to be a woman in your own home in front of a total stranger who'll come thinking that's what you are and won't see anything else!"
"But why?" I asked. "Why now, in front of a man I've never met?" The question sounded odd even to me—would I rather it be a man who knew me? "Why not ask a woman I've never met, if you want other people to see me?" I was reaching for any arguments I could find. If a woman saw I was a fraud I'd feel embarrassed, but if a man saw through me I'd feel destroyed!
"Jack,"—and now her voice took on an edge—"Do it! You want to be Jane, then BE Jane! You'd never fool a woman at close range—she'd nail you as soon as she looked at you, certainly as soon as you moved. But men never notice how women really look, and how they behave! YOU've never noticed! You wear dresses and lipstick, but you're not at all feminine in the important ways. You still have a lot to learn! You do this and I'll teach you a few things you don't know. I promise! Trust me!" She sounded exasperated and also a little threatening.
Then she smiled, half to herself, and her voice softened. "Here's the truth, Jack, or Jane, or whoever I'm talking to. This little hobby of yours has cost me a lot of grief, but I've accepted it. You've cheated on me, and maybe I drove you to that woman and maybe I didn't—I'm still working that out. But I won't live with a husband who's chicken-hearted as well as deceitful. I won't live with a closet queen! You want to dress like a woman, do it! You do it, but do it right! Tonight your real education begins. You are going to be a woman in the presence of a man who thinks you're a woman, and you are going to show me that you have the courage to do it! You may not know it, but that's what you want! Go upstairs and get dressed, Jane dear, and be sure you look pretty when you come down! He'll be here in another hour."
I had no option, not if I wanted to retrieve our marriage. I had to accept her challenge. I had always imagined that my first public appearances would be with women who would accept me as one of their own, and shield me from exposure. I had loved the vision of me sitting with other women, and chatting, and going with them to a restaurant for lunch. But this was something else.
Even so, Jill was right, I thought. I have been a wimp. If I'd been more assertive about wanting to dress up in my own home to begin with, I wouldn't have gone to dress up with Darleen, and now Jill wouldn't be feeling betrayed. If I were more of a man I would have been more of a woman to begin with, if that's what I wanted to be. She seemed to think so. She even offered to help me be more of a woman, if I went through with this!
Then a new thought struck me. "Wait a minute. You say you told him 'maybe he'd like to meet me'—what does that mean? You tell me to put on my prettiest dress? And to be sure I look pretty when I come down? Are you trying to fix me up with him? What if he starts coming on to me? What then?"
She got a very peculiar expression on her face, and looked at me with deliberate care, as if beginning a jury summation. "Well then Jane," she said, taking twice as long as needed to say "Jane", "If he comes on to you, then welcome to the club. That's what men do with women, don't they? That's what you did with that...Darleen of yours, didn't you. You'll just have to learn to deal with it, dear. If he's overwhelmed by your beauty and your charm and he wants to get his hands into your pants, then that will be a new feminine experience for you, won't it?" Her voice grew tighter: "You want feminine experiences, don't you?" Then abruptly, she turned away and went into the kitchen.
I went upstairs feeling uneasy but also a little elated. Finally she seemed to be thawing. Could it be that my wife was actually trying to fix me up with this new associate of hers. If so, was she trying to embarrass me, to subvert my manhood in my own eyes, the way my cross-dressing had subverted my manhood in her eyes? Maybe she did want me to feel like some queer queen flouncing around trying to attract a man, not the way I liked to think of myself, as a tastefully dressed girl chatting with other girls. Maybe she wanted to see for herself what kind of a woman I could be.
Well, if she was palming me off on him to humiliate me, it wasn't going to work. I would be friendly with him, but preoccupied. I wouldn't notice if he paid especially close attention to me. I would be pleasant, and no more than that.
Still, she was right in a way. If a man did try try to make time with me, that would be a new experience, a kind of affirmation of my femininity I could feel very pleased with. Real women enjoy that kind of reassurance all the time. My loins stirred, and I wondered what it was like to be thought attractive by a complete stranger. I wondered if I should try flirting with him. I began laying out my clothes for the evening. Some especially sexy lingerie, just for fun.
I heard Jill close the oven door and then come up, head into her room, and close her door. I called through it "How are we dressing tonight honey? You mean my prettiest dressy dress, or something more casual?" "That's my darling," she replied. "Don't push it—we're supposed to be two girls who were planning to have dinner together, with him an extra third asked at the last minute. A nice skirt, not elegant—say that black belted one that comes to mid-calf on you. Then you'll need a really attractive blouse to go with it, something that'll call attention away from ...your shape. That lovely flowered silk print, the green one? Heels. And no runs in your hosiery!"
The silk print had a bold pattern, cap sleeves, and a deep neckline. It was prim yet revealing, demure but assertive. I loved wearing it. It was me. I gathered my outfit onto the bed and began to feel optimistic. This was the first time my wife had ever praised any of clothes. Before, she had ignored them. Now she showed that she had been noticing, and that she even approved of some. All right! I would dress to please my wife, and not worry about the other man at all. I laid out a pair of medium-heeled black pumps, and went to shower.
Singing away in the shower, feeling good if a little apprehensive, I suddenly realized the blouse she wanted me to wear was short-sleeved and decollete. The hair on my arms and chest would be visible! I had to do something about that. When I dressed to please myself I could ignore such details, as did Doreen for her own obscure reasons. But this was serious. I had to look like a woman at first glance, close up, and maintain the illusion for the whole evening, or else appear ridiculous.
I had no choice. Jill had spoken, so there was no way I could switch blouses and come downstairs wearing something long sleeved and high necked. Besides, I wanted to look pretty for her! With a rueful smile but also a touch of excitement, I stepped out of the shower, reached into the medicine cabinet, took down a razor and shaving cream, and started shaving my whole body, chest, arms, and then for good measure my legs and crotch. It got to be amusing. I decided to give myself a bikini cut even though noone but me would ever see it, thinking that my French-cut panties would look far nicer without pubic hair mixed into their delicate lace edging.
Then I dressed, applied my makeup more carefully than I ever had before, especially the foundation over my beard, but also more sparingly than usual. Mousse, rollers, blow-drying, and combing out, and my hairdo was really rather flattering. I checked myself in the mirror. No raving beauty, but nice, even attractive. I noticed that Jill was already downstairs as I came down, doing things in the kitchen.
She smiled a wide, beautiful smile when she saw me. "How sweet, darling! You remembered to shave everything! That's very nice! And you look just lovely!" I was beside myself with delight. "But dear, you won't take offense if I make one little suggestion? Use a little more eye makeup. You have very nice eyes, and you'll want them to sparkle, and look mysterious, maybe even a little romantic." This puzzled me, but I decided she could still be playing her own game, to make me feel demeaned by a man's attentions, as if I dressed for other men rather than myself and now, her. Or maybe she had finally come around, and she genuinely wanted to help me become beautiful? My heart swelled up. Her tone had been gentle, not taunting, and I went back upstairs to add a little eye shadow, and then slathered on the mascara.
While batting my new, long, thick eyelashes in the mirror, it occured to me that Jill wasn't dressed the way I was dressed. We weren't exactly two girlfriends sharing a cozy evening, having dinner together. Instead, Jill had put on sheer black stockings, a short leather miniskirt I hadn't seen before, and a skin-tight, red stretch blouse with long sleeves gathered at her wrist. Her body and especially her breasts were beautifully sculpted in the fabric. She looked...sexy. The overall effect was tasteful, but still...very sexy.
"I thought we were dressing for a casual evening at home," I said when I came back downstairs, eying her up and down with much appreciation and some concern.
"Oh it is, darling," she said, her head inclined, smiling slightly. "But I want you to know right from the start, this is a very special evening for you. You won't forget it, I promise." She started to grin, skipped into a little dance step, twirled, lifted both her hands up and then out like a ballerina accepting applause, and beamed at me with unrestrained delight.
My exile had ended! Here I was, dressed and coiffed and made up, and I was the man she was dressing to attract! I reached out to embrace her, but she deflected my attempt at a kiss and just barely pressed her powdered cheek to mine, saying "Careful darling, you'll spoil our makeup!"
I LOVED it. "Our" makeup! I really did feel like a girl among girls, rapturously, and with my own wife! Together we finished setting the table, and while she looked after the last of the cooking, I set glasses and a range of drinks out on the sideboard. Now we were ready for her guest.
But not quite yet. Jill gave me a concerned look. "Dear," she said as I opened a bottle of wine to let it breath, "You're already acting like this evening's host, the way you always do. It's as if you lived here. Remember, you're supposed to be my guest tonight. an old friend who feels at home here, but still, this isn't your house. You're not supposed to know where everything is. You may give yourself away."
She paused. "I know. When he gets here it would be better if you weren't here at all. You have too many old habits, greeting people, taking their coats, and we don't want them to surface, do we?" I agreed "So," she said, "When we see him coming up the walk, you slip out the back door, cut across to the next street, then walk around the block and make a separate entry of your own. That should do it."
I wasn't too happy about going outside dressed the way I was, and told her so. I just didn't want to risk it. I never risked it even with Darlene. But she brushed aside my objections. "Oh pooh dear, you look just lovely. Very much a lady. Besides, it's dark out now. There's nothing to worry about. If anyone sees you, I'm sure they'll respect you."
I heard a car turn into the driveway. "Quick, he's here. Here, take my topcoat to cover your shoulders in case its chilly out. And you'd better carry this purse." She gave me a delighted conspiratorial grin and added, "Hurry back, dear. Don't let some stranger find you too attractive!" Then with a firm pressure stronger than I thought she could muster, she pushed me out the back door and shut it behind me. A moment later I heard a car door slam shut out front. The unexpected evening had begun!
I felt many things, all at once. Here I was out of doors finally, passing as a woman at last, though to nobody in particular. It was scary and exciting. I felt a cool breeze on my legs, and was suddenly aware that my skirt felt warm against my thighs. The air was a little chilly. I slipped Jill's topper onto my shoulders. So this is how women feel when they're outside, I thought to myself. It's rather pleasant.
Then it occurred to me. I didn't know what Jill's associate was like at all. Whatever she wanted me to do, I'd do better if I went around the side of the house and checked him over. I'd feel easier about making my own grand entrance if I knew what to expect. Was he fat, or young, or gawky, or dignified? No man had ever seen me in women's clothes, and only two women. I wanted no surprises. I need to match my feminine manner to the occasion, I said to myself, and I have no reflexes to fall back on. Better if I watch him come up the front steps and into the house. So I stepped down the driveway to the front of the house, my heels clicking, and I immediately went up onto tip-toe. Thank God these aren't really high heels, I said to myself. At least I can get them off the ground. I came around behind some bushes in front of the house, and saw our guest's back silhouetted against light from the open front door. He was very tall. Jill stood there framed in the doorway, her hand still on the doorknob, looking up at him.
He stepped forward, closed his arms around her, pulled her toward him, bent over her, and leaned into an intense kiss. She threw both her arms around his neck and kissed him back passionately, her red sleeves billowing over his shoulders, her legs planted apart and her hips thrust forward against his, as though she were trying to climb into him. Then they separated, she stepped back into the front hall, he took her hand and stepped inside, and Jill, her eyes never leaving his face, closed the door. There was nothing more to see.
I found myself still standing in our driveway, still hidden behind our bushes, wearing my nicest black skirt, a lovely flowered print blouse, respectable mid heels, a bit too much eye-makeup but still, very romantic, a purse under my arm, and my wife's topper thrown across my shoulders. Now I had to walk around the block, then return and put on my most genteel and ladylike manner and share dinner and the evening with my wife and...apparently ...her lover. I had no choice. All my other clothes were in the house where I couldn't get to them, and I was outside in a skirt being Jane, my wife's best girlfriend, and it was all arranged for me to come in and be Jane. Again, I felt a cool breeze across my legs.
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