Summer

I can't really remember exactly where my fascination with female things began. My first memory of it is from when I was about six years old, wearing one of my sister's dresses. My parents-who were both very old-school Conservatives and Christians-caught me, and needless to say, they were horrified. It's not something I care to revisit in any detail, not only because it was a traumatizing experience, but because anyone who's been dressing for any length of time likely has had one just like it. No need to keep beating a dead horse.

What I do know is that it wasn't anything sexual with me. Not at that age. I just liked the pretty, feminine things. They spoke to me; they felt right in a way that my boring pants and shirts just didn't. I didn't understand anything beyond that, but what six-year-old has ever been a philosopher? Even Socrates was six once.

But I digress. The real point of this story, and my transition into adulthood, was the summer I turned 19. My..'hobby,' shall we say, had only progressed since my tentative foray into the universe of lace and chiffon, and I was now almost fully immersed in it. Full outfits, stuffed bra, the works. I didn't have a wig, but I'd grown my hair so long that I didn't need one.

It wasn't perfect, though. I was still closeted to every single person in my life, and I had plans to stay that way for the foreseeable future. But I shouldn't make it sound like I was unhappy with the situation. In truth, I preferred it that way. The idea of being open about all of this, everyone knowing this intimate secret about me, was mortifying. I'd never been comfortable being the center of attention, and admitting that I liked to wear women's clothes would be tantamount to prancing out on stage in a ballerina costume in front of everyone. I just couldn't do it.

But the world is a strange place. It has ways of moving life forward, mechanisms that we mere mortals rarely have any control over. In July of 2006, in the little suburb which my family called home, one of these mechanisms took the form of my divorced neighbor Philip.

Before we get into the real nitty-gritty, let me describe myself. My name is Jordan. I'm pretty much average in every way. I'm 5'9", with straight, light brown hair. I wasn't especially effeminate, but my body did have enough feminine curves that my girly clothes looked good with very little extra work on my part. All in all, I was fairly blessed as far as my physical appearance went.

Philip, though-Philip was all man. He was in his late twenties, and managed a highly successful construction company. He was tall, over six feet, and well-muscled. Not bulky, but lean. His hair was as black as midnight, and he always seemed to have a five o' clock shadow. I wasn't attracted to him-I was straight-but the man practically oozed testosterone from every pore in his body. I really felt like a girl when I compared myself to alpha males like Philip.

I'd been enjoying the summer, three months of leisure before I headed off to college. Both of my parents worked, so I was alone in the house most days. Which is heaven to a closeted crossdresser, as many of you know. I pranced around the house in all kinds of girly outfits, just doing normal things. Even cooking or washing the dishes was exciting when I did it in a frilly blouse and miniskirt. If I hadn't tucked myself back, there would have been a very unladylike bulge in the front of my skirt.

The days passed like this for a little while, with me being en femme as often as I possibly could. I went through every outfit in my considerable collection at least twice, experimenting with different combinations-this top and that skirt, this one with these jeans, etc.

Every once in a while I would go next door and hang out with Philip. Despite the age difference, he and I had a lot in common. We would just sit around for hours, sometimes watching his big screen TV, sometimes playing video games, and always drinking. Just regular guy stuff, except that he was almost ten years older than me.

But that all changed in mid-July, about six weeks into summer vacation. Philip and I were parked on his couch as usual, beers in hand, while some football game or another played on the TV. I didn't care much for football, but I knew it well enough to be able to follow the game, and I didn't want to be rude since it was his house. So I just grinned and bore it.

When the halftime buzzer sounded, Philip muted the TV and turned to look at me.

"You know, you're not as covert as you think you are."

I blinked. "What are you talking about?"

He smirked, a sly look that I didn't like flickering across his face.

"You know, I just happened to glance in through your living room window yesterday, and I saw something interesting. Any guesses what that might be?"

I was stricken, and I knew it showed on my face. But I'd stayed hidden this long by being careful, so I decided to let him say it first. There was always the possibility he was bluffing, or just talking shit like guys do. "No," I said, putting what I hoped was an indifferent expression on my face. "How should I know what you saw? And if it was my mom undressing, I don't wanna hear it."

He laughed. "No, it was a lot better than that. It was so good, in fact, that I took pictures. You know, to preserve the moment forever."

Then, to my horror, he presented a stack of glossy 3"X5" photographs, clearly taken through my living room window, of me in an array of outfits. Most of the ones I had, in fact, giving the lie to his claim that he'd just happened to see me. This was obviously planned, long-term surveillance, which made me extremely nervous about his intentions. You don't go to this much trouble just to fuck with someone.

I flushed deeply, and I couldn't speak. I wished to all the gods that ever were that I could disappear on the spot. Then, when I looked at the growing smirk on his face, the one that promised me I was in for some bad times ahead, my paralysis broke. I got to my feet and turned to leave.

Philip's strong hand gripped my wrist tightly before I could go two steps, and forced me to turn back to him. When my eyes met his, the smirk was fading to a much more neutral expression, which eased my mind somewhat.

"It's not really that big a deal, man," he consoled me. "Lots of guys do this. They just lie about it, so it seems like this freaky, forbidden thing. But you don't have to be so afraid of it."

"I know what people would think if they knew," I replied quietly. "I know I shouldn't care, but I just can't live my life with this shit hanging over my head. Once people know, it'll be the only thing they think about when they look at me. When people talk about me, the first thing they'll say to describe me will be something like 'the guy who dresses like a girl.' I love doing this, it's a part of me, but I don't want it to be the only part that matters."

Philip was silent for a moment, considering this while he looked me over. I could feel a strange tension building in the room, but whether it was coming from him, from me, or both of us I couldn't say.

"You can't have it both ways forever," he finally said, his tone weary but firm. "If you wanna keep doing this, it's gonna come out one way or another eventually. You've got to decide what's more important. The dressing up, or other people's opinions of you."

"I know," I said miserably. "But I just can't. It's not gonna last forever, but I want to enjoy it, just like this, for as long as I can."

"I guess I can respect that," Philip allowed, his brows knitting together in concern. "But it's not a good idea to keep this all bottled up. When you do that, it comes out on its own in ways you won't expect. Don't you think it would be better to let it out yourself, on your own terms, so maybe you can keep it from completely destroying your life?"

He saw the panicked look on my face at even the possibility of coming out, and cut me off before I could speak.

"I'm not saying you should tell everyone. Not all at once, anyway. Just, maybe, let it out with me. Do what you do at your house when you dress up, but over here instead."

I could see where he was going with this, and I immediately shook my head. "Look, man, I appreciate the offer, but that would be a little too weird for me. You know, since we hang out and all."

Philip frowned and leaned forward in earnest. "I thought you might say that. That's what the pictures are for."

He spread them out on the couch in front of him, giving me a better look at each of them. I gazed across the glossy photos, feeling both uneasy and aroused at seeing myself dressed from someone else's perspective. I also had a sinking feeling that I knew what he was going to say next.

"I didn't want to have to do this, but you're so repressed that you're making yourself fucking miserable. I want to help you here, even if I have to force you into it. So here's the deal."

He leaned forward, and pulled on my wrist until I sat on his couch facing him. "You're gonna come over here at eight o' clock tomorrow morning, and bring all your girly shit. I'm off work tomorrow, so we'll have all day."

I looked at him warily. He was so confident and dominant that it completely disarmed me. It sounded like the fact that I might disobey hadn't even occurred to him. "All day to do what, exactly?"

"Whatever I want. Whatever I can think of for you to do. It doesn't matter now. What matters is that if you're not here at eight sharp, these pictures get emailed to everyone you know."

I yanked my arm free and leapt to my feet. "Seriously?" I demanded, shooting him a withering glare. "You're fucking blackmailing me? Really?"

"I'm helping you," he insisted, standing to face me. "Why do you think I did all this? I know you, Jordan. I know you need this, but I also knew you wouldn't do it willingly. Some guys just like to put on panties and jerk off, but I saw right away that you weren't one of those guys. You won't be satisfied until you're all woman, and part of being a woman is being with a man. Not just sexually, but in other ways, too. I want you to experience the whole package here with me this summer. I want you to be my new girlfriend, at least until you leave for college. And I know you want that, too, even if you won't admit it."

I was trembling now. From terror, or excitement, I was afraid to ask. Philip was looking at me differently now, and now that I thought about it, I realized that he'd been looking at me like that for a while and I just hadn't made the connection. He was looking at me like he had the cheerleaders in the game, or any other hot girl that came on TV. It was desire I saw in his eyes, desire for me. Or more accurately, the woman inside me.