Chapter 1: The File on Lee

I was pretty tired when I got to Nancy’s. Long day with the little darlings (that’s undergraduates to the uninitiated), including some of those sessions where the pretty little defenseless undergrad girl tries the old Higher Grades Through Salt Water trick. Tears, that is. I hate that. I hear that they’ve nicknamed me “Old Stoneface,” because I freeze up and turn sour when the faucets start to leak. Anyway, I was definitely in the mood for a little sympathy.

“Nance?” I called, as I entered. And I owed her an apology for being late. I could smell food from the kitchen; we had an agreement that we wouldn’t fall into the stereotypical male-female chore division, and tonight was my night to cook (So why was I supposed to be cooking at her house, and why did we spend 90% of our time together there? After all, she’d end up cleaning up any long-term messes, and by default keeping the place up. I can hear you sneering. Well, there was a reason. Basically, I’m a slob, and she hated it so much that she’d either have to clean it up, or suffer. She refused to do either, so except for rare occasions when I got active and cleaned things up, we stayed at her house).

“There’s some stuff for you on the couch!” she called back, cheerily. Sounded cheerful to me, anyway. I felt warmed a little; she sometimes bought things for me, totally spur of the moment.

I stopped cold when I saw what was on the couch, though. A pink satin little girl’s party dress, the kind with puffy sleeves and big white satin floppy bows on the skirt. My heart stopped beating for a moment, until I realized that it couldn’t be for me. She didn’t know, after all; she couldn’t know. She must have bought it for herself. Not really her style, of course. I noticed matching shoes, little pink patent-leather flats, with white bows, and relaxed. She was doing a Little Bo-Peep costume, or something. Not my concern. Whatever she meant for me must be somewhere else on the couch.

So I stepped closer, and spotted it. There were some packages and stuff, but they obviously went with the dress. The stuff for me must be the stack of paper. It was enormous, too — at least a ream there, I guessed. I picked up the top sheet, and my heart stopped again. I guess maybe it shouldn’t have started after the first time.

I was still standing there, in shock, with the sweat pouring down my face and my gut feeling as if someone had rudely used it for batting practice, when her voice, behind me, snapped me out of it. “Are you going to change for dinner?” she paused, and added, sarcastically, “Amy?”

I blinked, letting the pain wash over me, and turned to face her. Gods, she was crying! “I, uh, can explain,” I began, nervously, but let it trail off. What was there to explain?

She’d asked to use my computer that day, to do some project involving graphics for her company. My computer wasn’t ideally suited for graphics, but it was better than hers was. However, the graphics programs all ran under Windows. Windows is a bitch for security. Judging from the stack of paper, she’d printed out the contents of the datapersonalstoriesporn subdirectory. Which would explain the dress, alas. The stories weren’t really porn, but most of them did feature a boy or a man wearing an outfit like the one laying in front of me. I glanced back at the couch. Yup. The other packages were panties and stockings. Probably pink nylon with ruffles and white lace, respectively.

That tableau held for perhaps three minutes, her crying softly, me staring alternately at her, the couch, and the printout of the first page of one of my stories. She broke it finally. “Well?” she prompted.

My mind raced briefly, testing and discarding dozens of explanations. But ... really, what was the point of denying it? I shrugged, letting the old emotional armor settle into place. I smiled, sardonically. “I guess there isn’t an explanation,” I said.

Silence. “You don’t trust me,” she accused.

“Of course I... !” Pause. “Umm. No, I guess not.” Pause again, and an olive branch: “I hate it. I mean, I hate me when I do it. How could you not? So, uhh, I tried to stop, and ... umm, write it out.”

“Cross-dress, you mean,” she elaborated. A bit unnecessarily, to my mind. That was what we were talking about already, right? “You like to dress up and look like a girl.” She was taking this too calmly. I was a little worried. Sensitive position, as a professor, you understand, and junior faculty is not notoriously immune to being fired on moral grounds. They’d dress it up, of course, call it something else. I shrugged again, looking away from her. “You want somebody to dress you up and treat you like a little girl,” she continued, remorselessly.

“No!” I protested, genuinely shocked. My traitorous glands did their trick, though, and my heart raced, my mouth dried, my palms got moist, and my belly took the down elevator without warning. I had to explain this one. “No, really! I don’t, uhh, know why, and I’ve tried to stop — honest!” I emphasized as she rolled her eyes. “But it isn’t, uhh, because I want to be a, a girl!” My face felt hot. It got hotter when I realized that I was blushing.

She looked disgusted. Well, wouldn’t you have been? I would have, if I had been a girl and ... oh, never mind. “Lee,” she said, still much too calmly, “I read those stories.” I glanced at them. Not possible. Hundreds of pages. Skimmed, maybe. “The hero is always named Lee. And Amy,” she added. “He always gets forced into a dress like that, sooner or later. And likes it. Then, poof, he’s Amy for real.”

Good synopsis, my professorial side commented. I snarled at him. To Nancy, I smiled, mechanically, and replied, “Uhh, well, hardly any of them even have endings, and I was going to, uhh, turn him back, at the end. Just, you know, let him have a real experience of being a girl.” That was pretty weak, I admitted to myself. It was half-true, though. None of the stories did end, and I had always gotten stuck halfway through, looking for a conclusion that was emotionally satisfying. No, not even that — just a progression toward an ending that was emotionally satisfying. Come to think of it, most of the stories never even got to the sex-change part. A little foreshadowing, but it had only happened in two or three of them. How had she gotten the impression that it was universal?

She cleared up that little question. “Lee, dammit!” Finally a little emotion, something to understand. “I read your analysis, too!” Analysis? Oh, gods, that must mean the file called ‘anal,’ where I speculated on commonalities in the stories and possible reasons behind them. Once I knew she had read that, her earlier comment made more sense. A quote, a direct cite from that little bit of introspection. The dry-voiced little observer in my head commented that she probably hadn’t gotten the joke behind the name of the file — reference to my rather obsessive need to categorize. Christ, that damned file was written like a scholarly article!

I’d been so obsessed tracking down all those little information trails that I hadn’t answered. She had crossed her arms, was leaning against the doorframe, and the tears were streaming down her face faster. No mascara, I observed. She stifled a sob, and visibly gathered herself. Here it came, the ultimatum. “Lee, either you decide you trust me, or get out.” I must have looked puzzled. She explained the part that didn’t need explaining. “Forever.”

“I, uhh do trust you,” I told her. “And I promise I’ll stop, this time.” I actually had a plan, one that would probably work, if she didn’t stop me from doing it. It had worked once before, until somebody found out about it.

“You idiot!“ she shrieked, and sobbed some more, before controlling herself. I had taken a step closer, dropping the page, then paused, uncertain if she would accept comfort from me. “You can’t stop, you know that!” As a matter of fact, I had written something of the sort in that wretched file. I lost count of my attempts to stop before I got into grad school. She took a deep breath. “So trust me, and get dressed, or get out.”

Get... Get dressed? It took me maybe thirty seconds to figure out what she expected me to get dressed in, not because it wasn’t obvious, but because I simply refused to believe it. My fantasy come true? And then the spanking? No way! My fantasies were erotic; this was simply terrifying. And I shook my head sharply.

Another sob broke loose, and then she whirled and left. Out of my sight, she could let herself cry more freely; I heard her, from the bedroom. Doing something. I stood there, imitating a statue (except for the lack of pigeons, but I felt I’d been shat upon altogether sufficiently already). She came back with a bag, which she dropped by the front door. “G-get your d-dress and g-get out!” she said. Oh. My stuff, in the bag. I flinched when she called it ‘my’ dress, but not even the powerful yearning within me was enough to convince me to touch the damned thing.

I wanted to say something, but when she opened the door, the choice was pretty clear. Shame-faced, I slunk out, picking up the bag on the way. It occurred to me, then, with a sinking feeling, that she must have cleared her stuff out already. In anticipation. That brought it home to me: the relationship was over. I barely made it to my car before I started crying.

It cleared my head a little. It occurred to me that she had a very complete file on me, if she wished to blackmail me, or make me lose my job. Junior faculty can wear long hair, and maybe even get away with an earring (I’d waited until my first year was over before putting an earring back in, and never wore a pair, of course), but the only panty- clad faculty the administration was interested in were those that would help the Equal Opportunity statistics. Transvestic faculty were possible, I supposed, but only with tenure.

It didn’t occur to me until I got home that Nancy had been wearing a black silk blouse and miniskirt, and wearing high heels. Not that I understood it, then; I thought it was another taunt, a reminder of how the standard “accepting woman” of my stories was always dressed when they met. It wasn’t her style. She might even have bought it that very day.

When I got home, I discovered that she hadn’t taken her stuff away. Oddly, though, she’d found my stash of stuff — which was pretty pitiful, except for the lingerie, which was, umm, extensive — and mixed it with hers in her side of the dresser. It had been there before we’d met; I’d had it hidden for the eight months we’d been together. It took me a while to disentangle my stuff from hers. I had to do that. I’d promised myself that I would never touch her stuff, except to take her out of it, and I’d kept that promise. It hadn’t been easy; she was pretty damned sexy, and just her clothes could push all my buttons. She tended toward Indian print skirts, pants, and casual blouses, but she had some really killer outfits, and after she had realized my weakness for sexy lingerie, she’d indulged me by equipping herself with some.

I didn’t bag her stuff up, though. I bagged mine up again. I still ... hoped, you see. Then I laid down on my futon and cried and cried and cried.

Well, the hope got dashed over the course of the next week. I gave her a whole day to calm down, then called her up. It was an awkward conversation. Once we got past the preliminaries, she asked me if I was willing to trust her, and when I asked, clarified that that still meant wearing the damned ridiculous dress. Now, I admit I desperately wanted that dress, wanted to wear it, wanted to play at being Amy for real ... but I was not going to admit it. I look stupid in a dress. I mean, really ridiculous. Hairy legs, knobbly knees, big hands and feet. The mustache doesn’t help much either. Or the nose, I guess. So I refused, of course. I mean, I knew that she would never be interested in me sexually if she once saw me dressed, and I had my pride. The dregs of it, anyway. And what she wanted, I thought, was to try to humiliate me, to make me stop. I asked if I could have the stories back. She said no. But I could have the dress. We were both crying when we said goodbye.

I tried again two days later. It might have been the exact same conversation. We were both locked into our positions, and couldn’t budge out of them. I wasn’t going to be a party to my own humiliation. I didn’t tell her that, but I did say that I had stopped. The only thing she asked to that, was whether I had carried out a purge of my clothing, and she strictly forbade it. Anyway, she refused to return my papers again, and we were both crying, again, and we said goodbye, again. Except she added, “Lee, don’t call me until you’re ready to trust me.” Which meant, ready to be humiliated, I understood. The last thing she whispered I wasn’t sure I’d heard, for months. “I still love you.”

I worried about her concern for a purge all weekend. The only thing I could think of was that she planned on exposing me, and wanted that for evidence. Well, I could get around that — I’ve got lots of experience, lots of dodges. I found a self-storage warehouse place, and dumped a box full of clothes and cosmetics into a five-by-five. I wrote a careful note, basically, “I’d really like to have the printout,” put it with all her stuff, and dropped it off at her house one day when she wasn’t home. Left the key on top. I suppose I could have searched for it, but that would really have been a betrayal of trust, and I shied from it. I had to take her things back, because I was getting tempted to wear them. I admit, I sort of hoped she would give me the dress when she gave me the printout, but when the dress turned up, alone (well, with the accessories, but without the printout), I realized that I didn’t really want it. No, that’s not right, either. I realized that I wanted it too much. I put it all in the mail to her. And then hoped she’d mail it back. But she didn’t.

A pair of months passed, and I spent Halloween at home, with the lights out, pretending there was nobody there — and in boy clothes. We were coming up on the end of the semester. I’d been feeling truly wretched. Other girlfriends had found out; I used to tell them myself, in my college years. In grad school, though, one had broken up with me, using that for an excuse, and my armor had gotten a lot thicker. She had claimed that I would eventually become a transsexual, and I suppose I had been in reaction against that ever since, refusing to admit that, at some deep level, I did want to be a girl. It was a hard thing to figure out, anyway, since I knew, quite clearly, that I also liked being a boy, that I loved sex, and that I was a pretty good lover.

I was using an old technique to avoid cross-dressing, one I’d pioneered in college. It depended on the fact that I smoked. Basically, it was aversion therapy. I waited until I felt the familiar signals — sweaty palms, dry mouth, empty stomach, racing heart, and a fixation on pink, soft, and lacy. Then I went and got the one pair of panties I had left in the house, and put them on. And put out a cigarette. On my arm. Or sometimes my leg. The pain was ... extreme. In college, a friend’s girlfriend had learned what I was doing (I told her, proud of myself for having figured out how to stop), and she had had a fit. She was angry with me for hurting myself, not for dressing up. This was the same woman who had been angry with me, when I told her that I liked wearing women’s clothes, because I stole them. On the other hand, the one time that she had taken me shopping, she had made me pay at the register, refusing to take my money and do it for me, so I knew that she didn’t really approve.

But I finally stopped, and put the last pair in storage. I’d discovered myself contemplating the idea of putting the cigarette out elsewhere. And had also been contemplating filling a hypodermic needle (I had them from when I had visited a third world country, in order to not get an injection from a dirty needle) with air and ending the pain. I still hurt every time I walked by a place that had been ‘ours,’ and I was paying less attention to my courses than I should have been. The semester ended, and I found out how much less, from the student evaluations.

The day after I got the evals, after much soul-searching, I went and took everything back out of storage. I needed it, needed the release, in order to concentrate on my job. About half of it, unfortunately, had been ruined; it turned out that the warehouse I had chosen had water and insect problems. Some of the clothes were hopelessly stained, and much of my makeup had turned into puddles of goo. So I had a sort of purge, if not a voluntary one. About a week before Christmas, the day before leaving for my parents’ house, I went shopping. Christmas had always been a pretty good time for me, since a man buying women’s clothes was actually common, at that time of year.

I ran into her in the drugstore. I had gathered some foundation and blush, and had just picked an assortment of eyeshadow, when Nancy’s voice, behind me, remarked, “Those really aren’t your colors, Lee.”

I choked, looking around frantically, but no one else appeared to be within earshot. She’d gotten close to me because I always kept my eyes fixed firmly on the merchandise, avoiding the knowing looks of the other — inevitably female — customers. “It’s not for me,” I lied automatically. And blushed. Her face, which had been open and amused, went closed and cautious. Hurt? I don’t know. “It’s for my sister,” I added. I did have a sister. “Christmas present,” I mumbled.

“I see,” she said, coldly. “Do you know what colors she prefers? What does she look like? Green eyes, brown, curly hair, high cheekbones?” She raised a sarcastic eyebrow.

“No,” I replied, softly, feeling as if someone had taken a knife to my gut. “You’ve seen her pictures. Sort of dirty blonde, brown eyes. I don’t know about cheekbones, I never noticed.” I was looking down. I didn’t want her to see how much it hurt.

“Oh,” she replied, sounding disconcerted. I still didn’t look up. She released the basket I was holding, and I glanced up, quickly, to see that she had a puzzled, worried look. I gave her the famous mechanical smile, and walked away.

She was right, I decided at home. They weren’t my colors. At least I hadn’t got any mascara; the tears would have made it run.

I got back from my parents around the second of January. It had been the usual hideous Christmas, with inappropriate gifts and the required oohing and ahhing. I was as guilty as anyone else, of course, but that only made it worse. The only bright point was my sister’s baby, who got things she really did like, and enjoyed them quite openly. I almost asked my sister for makeup advice, but ... what did it matter? Nobody was ever going to see me in makeup. And if it made me look ridiculous, well, that would go well with the rest of my outfit, right?

There was a gift waiting for me. From Nancy. Two sets of makeup, one for a blonde, one for a green-eyed brunette. Or brunet. Also a little booklet of beauty tips. The note: “I’m sorry I misinterpreted ... if I did. Here’s something that should be more appropriate for your sister. And some for your friend, Amy. Merry Christmas. Love, Nancy.”

I worried at that note, and the package, for days. Why was that comma there, after the word ‘friend?’ Sending the makeup off to my sister was an easy decision. A good one, too, it turns out; she sent a letter back a week later effusively thanking Nancy (I’d told her who it was from). When I nerved myself to try the other, I discovered that she had been right. The mustache looked more out of place than ever, but in a bad light, if I put my hand over my mouth and upper lip, I might have passed for a woman with absolutely no skill in putting on makeup. I’d gotten a pretty nice haircut at home, too, more feminine than I had let myself wear it when Nancy and I had been together — just bangs in front, but that made an incredible difference from pulling it all straight back in the usual ugly guy’s style.

Once I’d used the makeup, I had to keep it. So I told myself. I also found a present for Nancy, one that I agonized over for longer than I had spent on all the presents for my family. I had to find something that wasn’t trivial, but that also wasn’t super expensive; I didn’t want her to feel uncomfortable about the cost. It had to be appropriate — personal — without being intimate. I finally settled on a soft leather over-the-shoulder handbag, one as casual as she usually was, but as quality. I figured she wouldn’t know how expensive it was. Hey, it may be obvious to any idiot that women know the prices of things that they usually have to buy, but I’m not an ordinary idiot, okay? I included a copy of my sister’s letter, too.

Classes had just started when I got a note from Nancy. “Lee, the bag is beautiful! But you spent much too much! Let me make it up to you: I’ll buy you dinner. Give me a call. Love, Nancy.”

I was in an absolute panic when I finally placed the call. But the chemistry had somehow changed; she teased me fondly, friendlily, and demanded that I let her buy me dinner and take me to a movie. I agreed, of course, hoping that something would start up again.

We went on a Friday night. In her car, with her driving. Not so astonishing, it was, as she pointed out, her treat, and we’d always shared those kinds of tasks before. She gave me a slight panic, early on, when I asked where we were going, and she replied, “Trust me.” I was very restrained all through dinner, wondering if she was going to demand that I prove my trust, and wondering if I would refuse, if she presented me with the dress again — she was wholly desirable, that night, and wearing the perfume I had given her, long ago. At the movie, she was very affectionately aggressive, her hands teasing me at odd moments, but fending off, gently, my attempts to return her caresses.

By the time we were in the car, I was confused, and a bit unsettled as well. Were we together again? I’ve never been good at reading the signals. She drove me home, parked the car, and leaned over to kiss me. I thought, for a moment, that I was going to come in my pants; I’d missed that so badly, the softness of her lips, the sweetness of her mouth. She broke the kiss, and I sighed, licking my lips.

She giggled. “I love the way you do that,” she whispered, and my heart leapt into my throat.

I managed to open my eyes, and surreptitiously cleared the tears from the corners. Hers seemed unnaturally bright as well. I hesitated, fearing the ‘no,’ that was sure to come, but managed to force the words out — they had to turn sideways and slither past my heart, which was still blocking things up. “Will ... would you like to come inside?”

She smiled, and I thought my heart would break. But then she asked, “Did you like the makeup I gave you, Amy-Lee?” Something crept into her eyes as she whispered the question.

I know that my eyes probably reflected abject fear. I was trying to figure out what hers were saying, there with the dim light from the streetlamps, and caught in a struggle between fear and desire. I’d never thanked her properly, she was hinting, or so I thought, and I’d lied to her and hadn’t trusted her. Could I trust her even enough to tell her that I liked her gift? “Yes,” I croaked, answering my question and hers.

She kissed me again, and the release of tension was enough to let me decide what I’d seen in her eyes. Fear. Fear of being hurt, of being lied to, again, probably. This time, when she broke the kiss, she laid her head on my shoulder, and her fingertip followed the tip of my tongue. It was an old trick of hers; she’d always been fascinated with the fact that I savored her kisses so much that I had to lick them all up when they were over. “Will ... Can you show me, if I come in?” she asked, in an oddly thick voice.

That question was more or less equivalent to a handful of speed. My poor, abused heart, that had just spent several minutes crowded into my throat, and then brittle as glass, took off like an Olympic sprinter. It didn’t have far to go, really. Nancy had always had it in her keeping; it fled there, where it had always been well-treated. I made an absurd little whimpering sound, and squeaked, “Y-yes.”

She hugged me tightly, for a long pair of moments. I absently returned the hug — I mean, really absently. Most of me had run for shelter somewhere, and I felt weirdly detached, like in the middle of an acid trip. There and not-there. She pulled back, finally, and whispered, “Come on,” taking my hand to pull me out her side. As if she was afraid to let me get too far away. In that oddly detached mood, I let her lead me to the door, and watched as she repeated my actions from the car, surrpetitiously blotting tears from the corners of her eyes.

We went in, and she led me to the bathroom. My hands were trembling convulsively when she let go of them, and took my coat. She disappeared, and I found the makeup, still operating on autopilot. When she came back, a moment later, I had tears standing in my eyes again, because the lipstick had mostly missed my lips. I started to wipe it off with the back of my hand, feeling horribly ashamed, but she stopped me, then gently cleaned my lips and my hand with tissue. Her glance, now, seemed compassionate, and I hoped, desperately, in the part of me that was shrieking in terror, that she would let me off the hook. She did, sort of. I guess. She put the makeup on me; I just stood there, obediently.

“There!” she said, finally, turning me to face the mirror. “That wasn’t so hard, was it?”

“Yes!” I gasped, and then laughed, half-hysterically, before bringing myself under control. Her eyes looked concerned, when I caught them in the mirror, reaching up to blot the tears again.

“You’ll run your mascara,” she warned softly, and I gasped a laugh again, as she slid her arms around me from behind. I relaxed into her, and finally dared to look.

It was a more remarkable transformation than the one I had managed on my own. Well, that was predictable, I guess, she had experience with the stuff, and got the blush in the right places, and the shadow properly feathered. I stared, a bit taken aback, and then, reflexively, laid my forefingers across my mustache, hiding it. She giggled at that, and I blushed, and got fascinated by the way the blush made my face look even softer and more feminine.

The terror was receding, turning into a fear that was more controllable. It was very odd, and I didn’t really understand it. We stayed there, staring at the mirror, or at each other’s eyes in the mirror, for what seemed a very long time. Then she let out an enormous breath, and the world all came back into focus for me. It was an ordinary, mundane world, and I hadn’t died of wearing makeup in front of her. I was enormously proud of myself.

“Where’s your makeup remover?” she asked.

“My what?”

She giggled. “Okay. I know you have coconut oil. That’ll work.” She found it, and then said, “Watch me.” She started taking off her own makeup. I hesitated, then followed suit, and when I was finished, relaxed even further. I suddenly realized that I was exhausted.

“I’m beat!” I said. I caught her eyes in the mirror, again. “Are you, umm, staying?”

She looked at me, calculatingly. “I don’t have a nightie,” she said.

I blanched. Okay. Another step. Just make the words come out. “I’ll loan you one,” I answered. ‘Of mine,’ her lips shaped. I nodded, feeling the heat return to my face, and added, in a small voice, “P- please, don’t make me w-wear one.” She looked, nodded.

Now’s the time for me to claim that our emotions, after having such a workout, turned into heated passion, and we made love all night. Well, no, we didn’t. We both wanted to, I think, but my cock wasn’t willing. I finally whispered, “Sorry,” and started to move to go down on her — she was wet, and I didn’t want to leave her unsatisfied — but she stopped me, and suggested that we cuddle instead.

But she was gone in the morning, when I awoke. The only thing that convinced me it wasn’t all a dream was my nightie, with her scent still strong, laying on the side of the bed. I had a vague impression of her getting up, kissing me, and moving around looking at things and talking to me, but I sleep like death, and have been known to carry on midnight conversations on the phone without ever remembering a word of what I said.

I wasn’t quite sure what to do, so I didn’t do much of anything. She called in late afternoon.

“Hey, sweetie! When will you be free to talk?”

“Umm, I don’t know. About what?” There was a long silence. My heart returned, and slammed against my ribs. “Did we agree to something this morning? I don’t remember. Whatever. I’ll do whatever I said. I don’t remember, that’s all!” Calm, Lee, I told myself. Don’t sound so desperate! Why not? I wondered. I am desperate.