His First Prom Dress

This was the alternate story I submitted to the ‘Awake’ project. Copyright 2011, Brian Katcher, do not repost without permission.

I looked at the pixilated bimbo on my computer screen, with her blond hair, long legs, and cartoonish chest. I would have done just about anything to get into her skirt. And her bra. And her panties.

And her shoes. And those cute earrings.

Realizing that my thoughts had once again entered dangerous territory, I began rhythmically tapping the space bar with my forehead.

Why me? Why me? Why me?

Now don’t get me wrong. In the highly unlikely event of internet girl ripping off her clothes in front of me, I would have jumped on top of her in a second. I was a sixteen-year-old dude, first and foremost. It’s just that I would have asked to try on her clothes afterwards. And maybe have her do my hair and makeup.

Why me?

Everyone has their fetishes, I guess. That’s what the web is for. Sure, you can instantly play chess with a South African researcher at an Antarctic lab, but the real reason the net was developed was pornography. Once people realized they no longer had to receive mail in plain brown envelopes, everyone got online.

I flicked off Miss January and sifted through the many websites that I didn’t dare bookmark. I figured being a teen cross dresser was about halfway on the pervert scale. Below guys who were into really fat chicks and amputees, but above the furverts and people who like to be peed on.

Why couldn’t I be normal and like to watch chicks spanking each other or something? I mean, I did like that, but…

Realizing I wasn’t going to work through my mental demons this afternoon, I spent a lonely hour googling things like ‘wedding dresses for men’, ‘makeup tips for cross dressers’ and ‘The Hulk vs. Godzilla’ (I do have other interests, you know).

“Jordan, boy, where are you?” I heard my dad bellow from upstairs. I quickly repeated the usual drill of purging the browser history. My parents weren’t terribly swift when it came to computers, but I think even they would be suspicious of training bra sites showing up in the auto complete.

“Down here, Dad.”

Dad and I had a lot in common. We’d both served in the military, both had been football heroes, and both drive cool cars. I did those things online, of course, but hey, bonding is bonding.

“You’re inside?” asked my father, grabbing a beer from the rec room fridge. “It’s beautiful out there. Finally warming up.”

“I’ve seen the outdoors. Overrated.”

Dad shook his head and smiled. My two older brothers were enjoying full football scholarships at Missouri State, so dad wasn’t too disappointed in his computer geek son. Actually, since we were now the only guys in the house, we’d gotten closer. Started talking more, hanging out.

“Hey, Dad?”

“Yeah?” He’d been about to turn on the TV (so much for the beautiful day), but paused.

“Um…nothing. Never mind.” I retreated to my room.

It’s funny, if I was gay, I think I could have told my parents. And I think they would have been able to handle it, even dad. People don’t really make a big deal out of that anymore.

But that was the kicker. I wasn’t a homosexual. The thought of kissing a guy turned me off so much, I wondered how girls managed to do it.

So I hunkered down, alone and embarrassed with my strange thoughts.

Damn it, can’t a guy just be pretty once in a while? Is that so wrong?


Eileen Fraces was an alternate cheerleader at my high school. Pretty, but not gorgeous, she’d kind of attached herself to me last year when she realized I’d let her copy my homework. Sometimes we’d hang out in the commons before school, so she could ‘check her answers.’

“None of this makes any sense!” she wailed, flipping through some tome from English class. “Why couldn’t anyone back then speak like a normal person?”

I leaned back in my chair, attempting to balance a pencil on the ridge of my nose. Eileen was actually smarter than she gave herself credit for. Sometimes I thought about asking her out, but decided to avoid that disaster. What if she said yes?

She stared at her book with a pout. “I mean, what the hell does this mean? ‘Uncle Misha was sent away for a long rest among the pines.’ So was he was camping or what? Hunting?”

The pencil rolled back across my forehead and clattered to the floor. “It’s a polite way of saying he was in a mental asylum.”

She threw down the book in disgust. “Then why don’t they just say that?”

“The same reason celebrities say they’re being treated for exhaustion. Yeah, they get exhausted right up their noses.” I returned to my pencil balancing attempt.

Eileen snorted. “Jordan, you have a hole in your shirt.”

Not big news, I paid little attention to my drab, male clothes. “Where?”

“Right in the armpit. You boys, I swear you’d all wear potato sacks if you could.”

No, I’d wear something cute and lacy.

“Well, Eileen, maybe you can loan me some of your things.” I said it without really thinking, figuring she’d assume I was being dumb.

“Hmmm…I might just have some things in your size, Jordan.”

I nearly jammed the pencil into my eye. Was she…serious? She was smirking at me, but not laughing. I was determined to play it straight.

“What, like your cheerleading uniform?” There was a faint buzzing noise in my ears.

Eileen continued to smirk. “You don’t have the figure for it. But I have a couple of outfits you might look good in.”

I folded my arms so she couldn’t smell my sweat through the hole. “Oh?” It was all I could trust myself to say.

“Couple of dresses, some blouses, maybe a skirt or two. Think I could get you to shave your legs?”

Everything in my universe vanished, from the dozens of kids milling around the commons to the pencil cracking in my tightened fist. Surely, surely, she couldn’t mean it.

“Sure…I’d, uh, shave. You know, if you think I need to.” Keep it light, Jordan, don’t say anything that can’t be taken for a joke.

Eileen cocked her head. “And then I could do your makeup. I’d make you look so cute.”

Yes, yes, yes! Oh, God, Eileen, I’ve waited years for someone to help me! Thank you!

Instead, I smiled. “So…Saturday?”

Eileen stared at me for a long moment, an unreadable expression on her face. Eternity came and went as I waited for her to answer.

Sure, Jordan. C’mon over. I can’t wait for you to try on my things.

The warning bell rang and Eileen’s cute face broke into a smile. “Jordan, you really crack me up. See you later.”

“Yeah! Ha, ha! See ya!”



At home after school, I simultaneously led my Marauders & Mages army into battle, while scanning through the ‘misses’ section of an online catalog. The encounter with Eileen that morning had really brought me down. Of course, she thought I was just kidding around. Why wouldn’t she? What the hell kind of guy wants to dress like a chick?

I fired a lightening bomb at an opposing paladin, then checked to see if they carried that pleated skirt in blue. I thought it might hide my hips.

God, which of my two fantasy worlds was the least realistic? I could never buy my own pretty things. It would be kind of hard to explain if my parents came across some extra large panties in my dresser. I’d have to wait until college…no, I’d have a roommate then. Christ, I’d be an old man of twenty-two before I could safely dress up.

I always did harbor a fantasy that someone like Eileen would volunteer to help me. Invite me over, dress me up, and then we could smear our respective makeup. Hell, it wouldn’t even have to be someone young and cute. Maybe an older woman who could help me dress like the daughter she never had. My own mother, God bless her, was a size two, so I never even attempted to ‘borrow’ her things.

The problem was, you can’t exactly suggest that to anyone. The incident with Eileen was just a repeat of the same brief conversation I’d been having for years now.

Me: Cute dress. Can I borrow it sometime?

She: Ha, ha, ha!

End scene

An incoming message from one of my opponents flashed on the screen.

Fishbone: Dude, wheres ur head at? u just lost 3 footsoldiers and a pikeman

Fe Man: sorry…bzy day

Fishbone: I hear ya. Today…

As Fishbone, a local guy I’d talked with many times but had never met, blathered on about his school day, I clicked away from the battlefield and began searching my other interest. I never expected to get a hit for ‘free makeover services for guys’ but I could dream, right? Right?

Fishbone: And then she tells me she wont go 2 the dance with me cuz she cant afford a dress. Can u believe it? No 1 duz that expensive dress shiz anymore. Last year one chick made a dress out of duct tape and this year some girl wants to find a guy to wear the dress instead. But i tried telling that to Jen and she was all like…

Most people would have missed it. Most guys would have ignored it. Me, I reread the line, just to make sure I hadn’t misunderstood.

some girl wants to find a guy to wear the dress instead

Fe man: What did you say about a guy wearing a dress?

Fishbone: Some junior chick from my chem class. Says she’ll only go to prom if her date agrees to wear the dress or something. WTF?

My sweaty hands trembled as I typed.

Fe man: Did she say why?

Fishbone: No

Damn, damn, damn! How could I explain to this virtual friend that he was possibly holding the key to my happiness, without revealing that happiness for me involved women’s fashion?

Fe man: Did she find a date?

For a horrible, horrible second, Fishbone’s status switched to ‘offline.’ I figured he’d been disconnected, and would have totally forgotten about this conversation when we next talked. But five seconds later, he was back.

Fishbone: Dont think she has a date. Y? U interested?

My heart’s dearest wish, accidentally dropped into my lap by some metal head gamer. Yes, I was interested.

Fe man: Sounds like a laugh. Give her my e-mail, will ya?

We chatted a bit more, and he signed off. I stared at the decimated remains of my once proud army, my head swimming. Why, why had I been so glib? Why hadn’t I told Fishbone that I desperately needed to contact this strange girl immediately? Instead, I made it sound like some vague joke.

Why? Because you’d rather live your life in slacks and sneakers than have anyone, even a stranger, find out about your desire to dress up like a woman. That’s the hard truth.


It was worse than waiting for Arrowhawk V to come out. Worse than when the Doomslayer game release was delayed. The school day dragged even slower than usual. I was short with Eileen. I was tardy to three classes because I was in the library checking my e-mail. Once, I nearly fell out of my chair when I found a message from Fishbone, only to realize it was some stupid forwarded video clip.

This is what I get from placing my dreams in the hands of a guy named Fishbone. If he hadn’t forgotten my request, the girl would probably just ignore what would sound like a desperate plea for a date. And I’d spend the next two weeks checking my e-mail every fifteen minutes, waiting for something that would never come.

That night, I sequestered myself in the downstairs rec room ‘doing homework’ at the computer. I think my parents realized this was just an excuse to waste time online, though as long as I kept my grades up and didn’t start wearing a trench coat, they never stopped me. Morosely, I checked my e-mail again.

And there it was. An e-mail from riotgrrl95.

Hey, Jordan. Steve gave me your address today. Why don’t you IM me? My name’s Andrea.

I’d received a thousand messages like this, but I was almost certain this wasn’t from a spambot. Fishbone’s real name was Steve, after all. I logged on to the chat program and found her online.

Fe man: Andrea?

Riotgrrl95: Is this Jordan?

Fe man: Yes

Okay, so she was a real person. That’s always a good start.

Riotgrrl95: Steve said u were looking for a date and willing to do something crazy.

I heard my mom’s voice at the top of the stairs, and for a terrible moment I thought she was going to come down, to interrupt the moment I had fantasized about for years. But she was talking to my dad, and her voice faded as she passed by. I made a fist to steel my hand, then typed before I lost the nerve.

Fe man: Like wear a dress?

She didn’t answer for a bit, but the program said ‘Ritogrrl95 is typing’ so she hadn’t abandoned me. It gave me plenty of time to second guess myself. Like what if that idiot Fishbone had misunderstood Andrea, and I’d just asked a stranger to try on her clothes?

Riotgrrl95: A dress…4 a start

I remembered this old sitcom, where a guy jokingly asked his girlfriend if she’d be into having a threesome, only to have her shockingly accept. I suddenly knew how he felt.

Fe man: I’d love to. Dress me any way you like. Makeup, jewelry, shoes, anything goes.

I then deleted the whole message without sending it, and replaced it with

Fe man: Why?

Riotgrrl95: Kind of complicated. U in St. Christopher?

My God, was she going to invite me over?

Fe man: Yes

Riotgrrl95: Meet me at the mall food court this sat at 4. We can talk. I’m tall, black hair.

Fe man: OK

Riotgrrl95 has signed off.


I arrived at the mall before two, grabbed a soda and a table, and proceeded to stare down every woman under thirty whose hair was darker than platinum blonde. I’m sure I creeped out more than one shopper. At around 3:30, a couple of guys I knew wandered by and talked to me for five agonizing minutes before leaving.

The closer I came to zero hour, the more nervous I became. On the one hand, I pictured a teenage Miss January showing up laden with dresses for me to try on. Not very likely of course. Probably just some girl who wanted to freak out a conservative principal by bringing a date in a dress. Or someone who just wanted to have a laugh. Or maybe this was some kind of cruel prank. I mean, I’d never met Fishbone in real life. What if he thought I was some kind of pervert (like I actually was) and was setting me up for some public humiliation? Or what if the girl told someone I knew that I was planning to dress in her clothes…


Her voice was amazingly calming, sweet and assertive at the same time. As for her appearance, well, the kindest adjective was ‘striking.’ Very tall, with short, curly, black hair. She wasn’t fat, but had a rather blocky, rectangular figure. She was dressed in jeans and a sweatshirt that gave her a frumpy appearance.

At the same time, she had an incredible face. Not a beautiful one, God had been very generous when he passed out chins, ears and noses. But her smile, which included her deep brown eyes, instantly quelled my pounding heart and sweaty pits.

“You must be Andrea,” I said suavely, trying to stand. I banged my knees on the underside of the table and nearly dumped my Coke in my lap.

She cranked up the grin. “Let me grab a drink.” As she walked to the Orange Julius stand, I decided that this was already going better than 90% of the dates I’d had. I wondered if I should bring up the previous forbidden topic, or just let things progress naturally.

In the end, I chickened out. We just kind of started wandering the mall, talking about nothing in particular. Andrea had a cutting sense of humor, she made a snide, hilarious comment about every hipster, yuppie, and senior citizen we passed. Her jokes put me at ease, allowing me to avoid awkward conversation. Still, I wished she’d tone down her voice, I wasn’t excited about the idea of getting into a fistfight with a stranger the first time we met.

It wasn’t until we passed in front of a shop selling formal dresses that Andrea broached the subject I’d been anticipating with sweet dread. After making sure we were not being overheard, she turned to me. “So, Jordan, why are you willing to put on a dress to go out with a tank like me?”

“You’re not a tank!” I protested, though it wasn’t a bad analogy. If she couldn’t do fifty pushups, I was mistaken.

She seemed genuinely touched, but didn’t allow me to escape from answering. “A guy as cute as you could probably wrangle a date on his own. So why would you agree to this?”

I took a moment to consider what she’d said. Odds are, I probably could have gotten someone to go out with me, Eileen, or someone else I sort of knew. But I had no desire to rent a tux and spend an evening awkwardly staring at a girl I had little in common with.

“Why, exactly, do you want your date to wear a dress?” There. I threw the question back at her.

Andrea didn’t flinch from the question. “I don’t have what you’d call a perfect figure, Jordan.” She shook her head before I could think of an appropriate lie. “Seriously, I don’t look like the girls in the ads. And I don’t want to spend a Saturday night stuffing myself into a too-small, very expensive gown, just so I can sit around and not have anyone ask me to dance. So I decided that if I ever was going to show up to one of those things, I wouldn’t be the one looking awkward.”

It kind of made sense. With her stocky figure and angular features, there probably weren’t a lot of guys lined up to ask her out. And getting all dressed up to go to a dance alone probably wasn’t a lot of fun for her. But if her date was in the dress, no one would notice that she wasn’t prom queen material.

“So what about you, Jordan? Why would you consider getting pretty? I can’t flatter myself that it’s because Steve said I was a living centerfold.”

After hanging out with Andrea for half an hour, I think I would have agreed to go to a dance with her in our regular clothes. There was something about her that put me at ease. But there was no way in hell I would pass up my one chance to go strapless.

“Ah, you know how it is. Dances are lame. I thought this would be a fun way to, I dunno, sock it to the man.” Sheesh, what a cliché.

She looked at me for a long moment, and for a second I thought sure that she’d seen right through me. She knew that my willingness to dress like a girl had nothing to do with social commentary. But then she smiled, at least with her eyes.

“Excellent. Want to come over to my house tomorrow? I’ll need to measure you.”

“Yeah, sure.”

She squeezed my hand. “I’ll e-mail you the directions.” She began to walk off, then stopped. “Maybe we’ll do a practice run, see how you look in some of my clothes. Would you be up for that?”


“I’ll take that as a yes.” She strolled off, not looking back.

Twenty minutes later, I remembered to move.


I sat in my family car, parked in front of Andrea’s house, gripping the steering wheel. My folks had believed me when I said I was going to the Fantasy Shop to play Battletech. They’d long since given up trying to keep track of the many RPGs, board games and LARP sessions I competed in. It was easy to make an excuse.

Why wasn’t I going in? I mean, a girl had actually offered to dress me up in women’s clothes! Hadn’t I dreamed and fantasized about this for years?

True, she wasn’t great looking. And she obviously thought I was just some guy who liked to do silly and unusual things. But that was close enough. So why was I still in the car?

Maybe because I feared nothing could possibly live up to my expectations. Andrea’s plan of taking me to a dance in a dress was just social commentary, after all. She’d probably just find the silliest, gaudiest dress at Goodwill for me to try on, and that would be it.

Somehow, the idea of campy drag was worse than having nothing at all. I didn’t want to deliberately look ridiculous. Still, an opportunity like this would never come again. I locked the car and rang the bell.

Andrea met me with her crippling smile. “I was afraid you weren’t going to come.” Just for a moment, a shadow passed over her face, as if this was a regular date, and she expected me to stand her up.

The moment passed, and she led me inside. I noticed that she was wearing a baggy sweat suit. She apparently never gave her clothes a lot of thought. Once again, I had my doubts about her ability to make me look good in hose and heels.

“So do you mind if I measure you? Have you try on a couple of things?”

“Sure!” Mentally, I kicked my own butt. This was supposed to be something I was doing as a joke. I should have complained a little.

Andrea didn’t seem to think me strange, and motioned me to follow her to her room.

“Um, no one else is home, right?” I sure didn’t need to meet her dad, while I was dressed in his daughter’s clothes.

She laughed. “Don’t worry. I just live with my mom. She’s at tennis. No one will interrupt us.” She gave me a sly wink. What did that mean? Was she planning more than a game of dress up? Would that really be such a bad thing?

Andrea’s room…I would have thought a twelve year old boy lived there. No vanity, no frilly sheets, and incredibly messy. She knew I was coming over, but hadn’t bothered to pick up. That didn’t sound like any girl I knew, though to be fair, this was the first time I’d been in a girl’s bedroom since second grade.

What attracted my attention the most, however, was the pile of feminine clothes, carelessly tossed on the unmade bed. Skirts, blouses, cute tops. And since Andrea was a large woman, I knew they’d fit. I froze in the doorway, waiting to compose myself.

Andrea pushed pass me and picked up something from the pile. It was a longish skirt, something more for winter than the spring. She stared at it like it was a discarded porno magazine she’d found in the park. “Personally, I never much cared for stuff like this. I mean, why would a girl not want to just wear pants? Seriously? Who’d want to walk around in heels? You have no idea how hard that is on your ankles. You guys are lucky, no one ever expects you to dress up like a doll.”

Lucky? Lucky? You girls are the ones who are lucky! What I wouldn’t give to have the sort of wardrobe selection you all have! Why can’t I wear something silky every now and then? Why can’t I be the one hogging the sink to put on makeup? Not every day, just once in a while.

I drug my thoughts back to the situation at hand. “Aren’t those your clothes?”

Andrea dropped the skirt on the floor. “My mom buys me this crap. Wants me to look like a little lady.” She shook her head in disgust.

I glanced around the room, mentally searching for a pair of sandals and a copy of Women’s Golf Magazine. Then again, I was probably just being paranoid. Andrea was clearly just a girl who liked being her own person. I had other things on my mind at the moment.

“So…” Was I actually going to say it? What this actually going to happen? “Should I try something on?”

“Hold on there, cowboy. I have to measure you first. Hands over your head.”

I felt the blood rush to my head as Andrea measured my hips, stomach, and chest. It was unnecessary, I already knew I had a perfect 26-25-26 figure. But to have a girl actually measuring me for my own dress…it was almost exactly how I’d fantasized it. If Andrea were built like Miss January and wearing a bikini, it would have been dead on.

All too soon she took her hands off of me. “Okay, I’ve been dying to see this. Why don’t you go in the bathroom and try these on?” She handed me a random skirt and blouse, two items that did not remotely match. I knew better than to bring this to her attention.

When I realized that panties were not going to be part of today’s agenda, I retired to the bathroom. Removing my jeans and shirt, I held the skirt up. For nearly my entire life, I’d ached for this moment. Within seconds, the soft fabric hung around my knees. A gentle draft of air from the register blew up between my legs. No rough denim, no constricting pant legs. Just free and breezy and so natural! Maybe she’d let me borrow this, so I could ‘practice.’

I pulled the poofy white blouse on next, struggling a bit with the unfamiliar, wrong-sided buttons. It was too tight around the stomach, too loose around the chest, and contrasted glaringly with my skirt. But who cared! It felt so soft, so airy, so right. So very right.

“How’s it going in there?” Andrea called. Ecstatic over the chance to shamelessly parade around in a pretty outfit, I joined her in her room. I cringed, inwardly, when I realized she’d already put away the other clothes. I guess I wouldn’t be trying anything else on today.

Andrea let out a wolf whistle when she saw me. “Nice, very nice.” Turn around. I gave her a little spin. “Doesn’t fit quite right, but that’s not what you’ll be wearing. Sit down.”

I seated myself at her desk. Another guy might have been silly and flamboyant, or extra masculine for effect. I simply straightened my skirt, gently sat, crossed my legs, and lay my hands on my knee. I’d been able to practice this, at least.

“Wow, Jordan, you move like a girl. When you want to!” she quickly added. I shrugged.

“Could I get you to shave your legs for the big night?” she asked.

I would have loved to have gone to the dance with my legs silky smooth, but I couldn’t risk my parents noticing. “Sorry.” God, was I ever sorry.

“Didn’t think so. So…” She looked at the floor. “The dance is Saturday after next. Will you be my date?” If I wasn’t mistaken, her ears turned just a little red.

“Of course.” She must have thought I really hated dressing like this. Or maybe that I didn’t want to be seen with her.

“Great!” There was that smile again. A dangerous smile. A smile that could make a guy do some strange things…especially if he already wanted to.

“So, um, about my, er, about the dress…”

She shook her head. “Don’t worry about that, I’ll take care of it. Just show up here around six. I’ll make sure my mom is gone.”

But the dress! I had a thousand suggestions, a million ideas! And what about my hair? Makeup? Shoes? Jewelry?

“Yeah, okay. Anything I need to do?”

“Just take a bath. And shave. You can’t be all stubbly.”

I rubbed my hand over my sparse chin whiskers. I’d always felt unmanly because I couldn’t grow a full beard, though I wasn’t sure if that was a good thing or not.

I stood. “Well, I guess, I’ll see you then.” Unless you’d like to do my nails.

“Yeah. But, um…”

“Yes?” I asked, hopefully.

“Well, my mom called, she’s going to be pretty late. Do you have anywhere you need to be?”

“Not for hours.” Could I be that lucky?

“Would you like to hang out for a while? Play some video games or something?”

Damn. Oh well, that’s what I did with most of my time anyway. And Andrea was much better company than…well, a lot of people.

“Sure. Sounds like fun.”

I ended up staying for three hours, playing on the computer, eating snacks, and getting beat at ping pong.

I never asked to change out of Andrea’s clothes, and she never suggested it.


A few days after Andrea dressed me up, I lay back on my bed, happily remembering the experience. The skirt. The dress. Walking like a girl. Andrea dragging me into the shower.

Okay, maybe I edited the events (and Andrea’s looks) in my mind, but what of it? I’d actually got to dress in comfortable clothes. No one could ever take that away from me. God, life was good.

I picked up the phone and called Andrea.

“Hey, Jordan!” She sounded delighted to hear from me.

“Hey, Andrea. Listen. I…I can’t go to the dance with you.”

“Oh!” Her happiness deflated.

“I mean, wearing your clothes. I’d still like to go with you.”

That was the problem. I’d been so psyched up about wearing a dress, I hadn’t stopped to think that I’d be wearing the dress in public. At a local high school. Where people I knew might see me.

And much as I wanted to dress up more than anything, much as I longed to let Andrea make me pretty for the big night, I just couldn’t do it. I called myself a pervert enough in my mind. I didn’t need a bunch of other people joining in.

The line was silent for a moment. “Feeling a little scared, Jordan?” Her voice was calm, not angry or mocking.

“I’m feeling a lot scared, Andrea. Let’s just go together. You’ll look fine.”

I would have looked so pretty. I would have been so happy.

“Jordan, let’s get together. Meet me at City Park, by the fountain. We have to talk.”

She hung up.


It wasn’t easy for me to get to use the car, but I wrangled it. I sat on a bench, waiting for my date. How could I explain to her that I had no problem with the dress. She could give me a makeover every day of the week, if only no one would know. What if this got around my school? What if my parents found out? Jesus.

She soon joined me. She was decked out in a heavy trench coat, even though it wasn’t that cold out. We sat there for a few minutes, not speaking. With the silence and her coat, I felt like we should be exchanging secret files in a folded newspaper.

“Jordan,” she said eventually, “I can’t say I’d blame you if you didn’t want to do this. And the last thing I want is for you to be uncomfortable.”

“It’s not that.” I wished I could explain exactly what ‘it’ was.

“Then listen. Jordan, I’d really like to go to this dance.”

“Then let’s go!” I interjected. “I can get a tux and…” The sad look on her face cut me off. Good thing, I sure as hell didn’t want to rent a tux.

“Jordan, I’d love to go with you. But…maybe you don’t understand how girls are. These dances, we’re supposed to spend months getting ready. Hair, makeup, shoes, clothes, everything.”

I closed my eyes, fantasizing.

“But if I did all that, I’d still just look like a dumpy, unattractive girl. It would just drive home how ugly I am.”


“Let me finish.”

I glared at her. “I’ll be damned if I will. What the hell’s your problem? I happen to think you’re good looking.” Good being a bit of a stretch.

“Jordan, I know you mean well.”

“Shut up! I’ve known you less than a week, and I’m sick of how little you think of yourself. You think I couldn’t get another date?”

She smiled a little. “Of course you could.”

Yeah, but not one who’d let me wear the dress. “But I want to go with you. And if it takes me wearing a dress, then damn it, I will!” Did someone step in something around here? I was certain she’d see through my excuses.

Instead, she smiled. “Thank you, Jordan. Just one night. If everyone’s looking at you, I’ll feel less self-conscious. I’ll never ask you to do this again, I swear.”


“Are you sure no one will think I’m…fruity?”

“No, I’ll build you up as Captain Macho. Guy in a dress, that’s always funny.”

Double damn.

“And we won’t get kicked out by your principal?”

“Nah, they’re all into the whole LBGTMNOP alphabet at my school. They won’t make waves.”

“You know I’d only do this for you.”

She touched my cheek. “You’re a special guy, Jordan.”

Impulsively, I put my arm around her, and we sat like that for a long time. It was nice.

I wondered what her real motivation for my crossdressing was. I found it hard to believe that was the only way she’d feel comfortable at the dance. But I didn’t press. What if she asked for my real motivation?


Since the sixth grade, my parents had been badgering me to ask someone to a dance. And now that I actually had a date, I had to tell them I was going to an all night ‘Lord of the Rings’ marathon at the Fantasy Shop. That was the great thing about being a nerd, your parents never checked up on you.

I parked my car and grabbed my small bag of toiletries. There were no cars in front of Andrea’s house. With confidence and dread, I knocked on her door.

“Jordan!” She seemed happily surprised to see me, like she expected me to ditch her on the night of the dance. She was wearing a heavy white bathrobe, apparently just out of the shower. “Please, come in.”

Her half-nudity momentarily distracted me from my fantasies about my dress. Even though we’d agreed to meet rather early so we could get ready together, I was still being invited into the house of an unclothed woman. Chunky or not, this was an intriguing development.

“Well, Mom’s out of town, so we have the place to ourselves. Are you ready to see your gown?”

I’ve been ready for sixteen years. “Yeah, sure.” It took all my self-control to follow her, instead of bolting for her room.

It was lovely. Now we’re not talking supermodel lovely, or Cinderella fairy godmother lovely. It was clearly something from a second hand store, and had probably been some sort of stage costume originally. But I didn’t care.

It was laid out on Andrea’s unmade bed. Light blue, with poofy sleeves and an floor length skirt. To me, it glistened and shone. I wanted to grab it, clutch it to my chest, and twirl. I wanted to plant a kiss on Andrea’s lips to thank her. Instead, I just laughed.

“Nice. I hope you didn’t spend a lot.”

She gave me a shove, which nearly toppled me over. “Do you know how hard it is to shop for someone with your size? Plus I couldn’t get anything with a plunging neckline.”

I fought the urge to go over and finger the soft material. “I guess I don’t have the boobies for that. Speaking of which, how am I going to fill out the front?”

“I got some powerful hormones. You wouldn’t mind growing a nice pair of C cups for me, would you?” She smiled her devilish smile.

“Uh…” The room suddenly grew very warm.

“Oh, lighten up, I’m just joking!” she said, smiling at my discomfort.

A joke. Of course. There were no real hormones that powerful. But just for a moment there, I wondered how far we were both willing to go.

“Actually, Jordan, I do have something for you. Check it out.” She held up something that appeared to be a padded bra. “It’s for women who’ve had mastectomies. I think it’ll work. Here, take your shirt off.”

Play it cool, Jordan. Just take your shirt off. Just like at the pool. Perfectly natural. Your date just wants to help you with your bra. Your date, in her bathrobe.

With my top off, it was suddenly very chilly in the house. I shivered with the cold and with excitement.

Andrea stood behind me, helping me get my arms through the straps. She then clasped the back and adjusted the cups over my chest. Let’s just say it was a good thing she wasn’t standing in front of me at the moment.

“Is that too tight?”

“No. It feels good. Real good.”

Her large, soft hands slowly slid from the bra, and only my stomach. For a few seconds she held my belly, her warm breath in my ear. Suddenly, she broke away.

“Great!” she squeaked. “You look great.”

“So can we get on with it?” I growled, trying to get my breathing back under control.

“Maybe I don’t want to hurry. Maybe I want to keep you like this,” she said with her evil smile.

My eye gave an involuntary twitch. What was she suggesting? I’d never been past first base with a girl. Andrea wasn’t exactly a head turner, but she was nice…

“Oh, don’t look so panicked. I’m just messing with you.”

“Oh,” I said, not a little let down.

“Now, in order to fit into your dress, I need you to wear this.” She held up something that looked like a restraining device for mental patients.

“A girdle?”

“Something like that. You don’t exactly have an hourglass figure, honey. Hands over head.” She then yanked and tugged until I felt like my ribs were bent into all kinds of strange shapes.

“Aren’t you going overboard?” I gasped.

“Please. You’re lucky you don’t have my figure.” She finally fastened the clasps. Then, she patted her wide belly. “Not exactly a Barbie doll type,” she sighed.

“You look fine.”

While I had always suspected making myself pretty would be hard, I certainly hadn’t thought it would be this uncomfortable.

“What now?” I asked, my voice cracking.

She roughly pinched my cheek. “Time to make up that cute little face of yours.”

Looking back, I think she may have been trying to get a rise out of me, just to see how far I would be willing to go with the illusion. At the time, I was too excited and nervous to think about it.

Andrea took me to the bathroom and began to primp and powder my face. She kept having to search for things. I doubted she ever wore makeup herself, and was probably using her mother’s.

She refused to let me see myself in the mirror while she worked.

After a while, we began to chat about other things. It was almost as if I weren’t sitting there in my bra getting a makeover from a teenage girl.

“You have nice features,” said Andrea, as she brushed on mascara.

“Um, thanks?”

“Don’t take it wrong. I just wish I had your cheekbones. And your height. Please don’t be offended.”

“I’m not, believe me.”

For a second, I thought I’d said too much, but Andrea didn’t pause. “I think we’re finished here. No, no mirror yet. You have to see the complete package. Why don’t I get your gown?”

I was too nervous to answer, so I just nodded. Andrea led me back to her

room, where she held up my blue and silky dream.

I didn’t really have time to examine it before she was helping me into it. It was poofy and soft (as a teenage boy, even one with interests like mine, I didn’t know the proper terms for describing it). The shoulders were puffy and, while it was full in the front, it plunged in the back.

“This will show off your cute figure,” said Andrea, zipping me up. “I wanted to get something strapless, but I don’t think you’d have shaved your armpits.”

At that point I would have done anything.

“So can I see now?” I tried to sound bored, but the longing in my

voice was that of a child on Christmas morning.

“In a second, beautiful. A couple of more things. Look.”

Much to my surprise, she had bought me a wig. On closer inspection it was just a cheap Halloween type thing, but the long brown strands covered up my own short hair. Andrea pinned it in place and gave it a quick brushing.

Thinking we were done, I started to get up, but Andrea effortlessly pushed me back down. “Be patient, gorgeous.” She clipped a bracelet around my wrist. “It’s too bad your ears aren’t pierced. But here.” She snapped two plastic earrings to my lobes.

“Now are we finished?” I tried to pass off my excitement as restlessness.

“Yeah. There’s a full-length mirror in my mom’s room. Let’s go.”

Andrea didn’t turn on the lights until I was standing right in front

of it.

I wish I could say that I now looked like a complete girl, who no one would recognize, but that wasn’t true. A cheap wig and an amateur makeup job can’t instantly transform anyone. I wouldn’t pass under close inspection. But my God–

I was pretty! I was truly pretty. A pretty boy, but pretty nonetheless! My big eyes stared nervously from behind painted lashes. My lips and cheeks were a delicate red. My puny arms looked more in place coming out of the dark blue dress sleeves than they ever did in a suit jacket.

I looked at my benefactress. “What do you think?” she asked.

“Wow!” I couldn’t bother to hide how impressed I was. “You certainly did a number on me!”

“You don’t think it’s too much? We could lose the wig if you want.”

I waved a finger at her. “Now don’t you go backing out! Hey, we’re running out of time. Um, when are you going to put your dress on?”

“Tell you what. You wait here; I’ll go in my room and get ready. Unless you’d like to help me get dressed–my God, it was a joke!”

I’d really have to start covering my surprise better. I’d almost said yes.

Andrea winked at me over her shoulder and left me alone with the mirror. For the next twenty minutes I posed in front of my reflection. I practiced giggling, flipping my hair, and girlishly twirling. A new wig, more makeup practice, clothes of my own…I began to think about when it came time to leave home in two years. What sort of life would I choose?

I guess I’d lost track of time. As I fluttered my eyelids at the mirror, I noticed Andrea was watching me from the doorway. I was about to try to explain I was just playing around, when I noticed how she was dressed.

She was wearing a tux! Not a cheap one, either, a real, fitted tux, with a tie, vest, and jacket.

“What do you think, honey?” she asked me.

“You look so…” what should I say? Pretty? Attractive?

“You look really handsome.”

Andrea’s face cracked into a smile and I knew I’d said the right thing. “I can’t wait to get you on the dance floor,” she said. “Are you about ready?”

“What about my shoes?”

Andrea sighed. “I couldn’t find much in your size. The dress will cover up your sneakers. Besides, I don’t think you should risk you falling off your heels this first time.”

“Okay.” I pulled on my shoes, not stopping to think what she meant by ‘first time.’

Andrea loaned me one of her purses to keep my wallet and keys in. As she locked the front door, she stopped. “Oh, I forgot something. Wait here.”

She ducked inside, and quickly returned. She was holding a plastic box with a corsage inside. Wordlessly, she clipped it to my wrist.

I couldn’t remember the last time I’d been so touched. “Thank you,” was all I could say.

“Just a little something for a pretty girl.” She cocked an eyebrow, waiting for me to be offended. She’d have to wait a long time.

We walked to Andrea’s car and she opened the door for me. She then demonstrated how to smooth my dress and sit down so it wouldn’t ride up my legs. We were off.

It took us about half an hour to get to her high school. On the way, she gave me pointers about watching my makeup, about how not to sit with my legs open, and a few tips on how to hold myself when I walked.

“So are you nervous?” she asked.


“Don’t be. People will think this is funny. We’ll have fun.”

“As long as I’m with you.”

Andrea chuckled and I giggled.

When we pulled up to her school, I lost my nerve again. What the hell did I think I was about to do? Waltz into a high school dance all decked out in a gown and makeup, and no one would think I was a big weirdo? Had I lost my mind?

Andrea noticed my near panic.

“You okay, Jordan?”

I looked miserably at her. “No, not really.”

She looked at the steering wheel. “We don’t have to do it.”

“I want to. I mean, I want to go to the dance with you. I just don’t know if I can do it like this.”

Andrea cocked her head. “See those three girls over there?” She indicated a group of young women, talking near the entrance. “They’re friends of mine. Why don’t we go say hi? If you don’t like how they react, we’ll go back.”

“Okay.” I picked up the purse, and let Andrea open the door for me.

It took a lot of nerve for me to take Andrea’s arm and walk with her up to the school. Andrea’s friends didn’t stop talking until we were right next to them. Then, they looked at Andrea, not me.

“Andrea!” squealed one of them. “Why are you dressed like that? And who is–OHMYGOD!”

The three girls all took one look at me and broke into laughter. But the weird thing was, it wasn’t mocking laughter. It was as if I’d just told a hilarious joke that it had taken them a couple of seconds to get.

Finally, one of the girls, a petite blonde, caught her breath. “Sorry to crack up like that, but we didn’t realize–oh, wow! You’re gorgeous!”

I knew I should have passed that off as sarcasm. I should have assumed she was joking. But to have a strange young woman describe me as gorgeous–I’d waited a lot of years for that.

Andrea began introductions. “This is Dawn, Jodi, and Heidi.”

“Pleased to meet you, ladies,” I said, smiling shyly.

Heidi, the blonde, wiped a tear from her eye. “Andrea, when you said your date was going to wear the gown, I thought you were kidding. Where did you two meet?”

“At the gym. Jordan was doing some bench presses and asked me to spot him.”

I smiled inside. She was making in clear that I didn’t do this sort of thing for fun.

“C’mon, let’s go inside.”

Heidi chatted as Andrea and I walked with her. “You look so cute in that dress! Is it yours?”

I felt it was time to assert my manliness. “What do you think?” I asked, with affected anger.

“Oh, I guess not. But you look good in it. Wish my boyfriend would let me make him over.”

Maybe you should ask him. You might be surprised.

“So what’s your name?” asked Heidi, as we reached the door.


“That’ll never do.” She turned to Andrea. “Andrea, what’s your girlfriend’s name?”

Andrea laughed her booming laugh. “I guess we’ll call her Julie.”

“In that case,” I shot back “you’re Andy.”

The principal, who was taking tickets, gave us a weird look when Andrea presented our passes. He seemed about to say something, but changed his mind. A far cry from my principal, Dr. Bailey, who once refused to let a student into a dance because he was wearing sneakers.

As Andrea led us through the decorated gym to a table, I noticed many heads turning towards us, first at Andrea in her tux, then at me in my dress. Why should that be? Could it be they recognized Andrea easily, but it took them a couple of seconds to realize I was really a guy?

Andrea and I had a seat, and Heidi sat opposite us. She immediately started touching up her makeup. On a whim, I borrowed her compact when she was finished and fixed mine as well. Both girls laughed.

“Hello, ladies.” A young man appeared at our table. He was everything I was not: tall, lantern-jawed, and muscular. He laid a hand on Heidi’s shoulder, indicating she was his date. “Nice tux, Andrea. And you are?” He was looking at me oddly. He probably assumed I was a guy, but wouldn’t want to make the huge mistake of asking, in case.

Heidi patted her date’s hand. “Drew, honey, this is Andrea’s boyfriend, Julie.”

“Girlfriend,” corrected Andrea.

Since when was I either?

Drew looked astounded, then shrugged. “Pleased to meet you, ‘Julie.'” He shook my hand, but delicately.

The four of us fell to talking and I began to relax. I’d almost forget the role I’d assumed that night, but someone would always remind me. People walking by would stop and stare, and usually laugh and point. Not cruelly, though. I got several wolf whistles and crude comments from guys.

“People here are sure understanding. I was afraid I’d get beaten up.”

“Don’t be dumb. They think we’re being silly. Why would that make them mad?”

After a bit, couples began to dance. Andrea stood up and extended her hand to me.

“Shall we?”

“I don’t know…”

“C’mon, I’ll lead.”

Andrea took me to the edge of the gymnasium and wrapped her arms around my waist, masculine style. I reached up and locked my hands around her neck, the way women dance. The difference in our heights caused my face to press up against Andrea’s chest.

I was never much of a dancer, but Andrea kept me in line. She helped me move to the music swirled me around the floor. When the DJ put on a faster song, she even twirled me a time or two.

If I had thought we’d be the center of attention, I was wrong. The other couples were concerned about themselves, not some drag act. With most of the other girls worried about their dresses, and most of the guys worried about getting their dates out of their dresses, it left little time to worry about Andrea and myself.

Of course, many teens couldn’t help staring at us now and again. The bolder students would sometimes shout out comments. “Nice legs, baby!” hollered someone. “Show me your tits!” hollered another guy. A teacher immediately got on his case.

I felt gentle tap on my shoulder. Andrea’s friend Dawn, a pretty, dark skinned girl, was standing behind me with her date. “Can we cut in?”

Andrea shrugged, and allowed Dawn’s date to lead her in a slow dance.

Awkwardly, Dawn and joined hands on one side, and placed our other hand on each other’s shoulder. Neither of us had the gumption to lead, so we sort of swayed awkwardly.

“I can’t get over how cute you two look,” said Dawn.

“Thank you. You look nice yourself.”

Dawn smiled. “So how long have you two been dating?”

“Not long. This is really only our second real date. I can’t believe I let her talk me into doing this.”

Dawn leaned in conspiratorially. “Andrea’s an old friend. She’s a great person, but she’s nervous around guys. She doesn’t think she’s pretty. I bet she wanted to ask you on a regular dance but was too afraid you wouldn’t want to.”

I could have told Dawn that we only met because I’d agreed to wear the dress, but I didn’t. “I don’t know that she likes me like that.”

“Well, you may have to be more aggressive. I mean, if you like her. Andrea’s the type of girl who’d challenge a guy to a tennis match when what she really wants is to ask him out. So do you like her?”

“I barely know her. But she is nice.” Very nice, actually.

“Well,” Dawn smiled. “If it doesn’t work out, you can just be one of the girls.”

“Yeah, yeah.”

“We could all go shopping together, do each other’s hair, trade clothes,” teased Dawn.

I wished she wasn’t joking, the prospect seemed wonderful to me. Instead, I tried to kid. “I don’t think I’m your size.”

“Maybe we’ll chip in and get you a tummy tuck.”

“What, no boob job?”

This pleasant conversation was interrupted by Heidi who wanted a turn with me on the dance floor. Heidi voiced Dawn’s concerns. She felt that Andrea was using this drag dance as an excuse to ask a guy out.

Though I didn’t say it, I wasn’t so convinced. Andrea had put a lot of work into both our costumes. I mean, if this was all just a joke, why didn’t she get me a dress out of the bargain basement somewhere?

When the next song ended, Andrea and her friends excused themselves to powder their noses.

“Are you coming, Julie?” asked Andrea, with her mocking devil’s smile.

“I’ll pass.” Soon the girls were gone and I stood alone near the dance floor.

As I waited for Andrea and her friends, I felt a tap at my arm. It was a boy of about fifteen, blonde and skinny, who was looking at me with suspicion.

“Ironman?” he asked, unexpectedly.

It took me a second to connect that with my online handle. There was only one person who’d know me as that. “Fishbone?” I asked.

“Holy shit, it is you! I wasn’t sure if you were serious about this or not. So you’re here with Andrea?”

“Yeah. It’s weird, but fun too.”

“Holy shit!” he repeated. “I can’t believe you went through with this.”

“Do me a favor, Steve. Don’t mention this online.” I didn’t want this story to get around, even electronically.

“Sure thing, dude. I mean, yes ma’am!” He laughed.

“Could you do me one more favor?”

He backed up. “You’re not going to asked me to dance, are you?”

“No, wise ass. I have to go to the bathroom.”

He stared at me for a second. “Are you going to go to the girls’ room?”

“Of course not. But I don’t want to wander into the men’s room like this.”

“Follow me.”

Steve, aka Fishbone, led me down a darkened hall, deeper into the school. We turned a corner and he pointed to another restroom. “You should be safe in here. See ya round.” He shook his head and was gone.

I slipped into a stall and attempted to pee without wetting my pretty dress. If I ever did this again, I thought, I’d have to ask Andrea how girls managed.

Did this again. As I washed my hands I looked at the face in the mirror and wondered. How could I do this again? Homecoming was six months away. Andrea might be interested. Maybe she’d be willing to doll me up now and then. There was just one problem. I’d have to tell her I enjoyed playing Julie.

I touched up my makeup again with the compact I’d borrowed. I didn’t look half bad. When I went to college in two years, maybe I could meet some people who’d help me dress like this.

My musings were interrupted by a shadow behind me. It was a boy, decked out in a tux. He was very handsome, solidly built, with dark wavy hair, tan skin, and five o’clock shadow. He was staring at me in a way that didn’t make me feel exactly comfortable.

I turned and faced him. “Hello.”

“Hello, yourself. You’re Andrea’s date, right?”

“Word gets around.” I picked up my things and prepared to leave.

“What’s your name?” the boy asked.

“Jordan. Guess you can call me Julie tonight.” Why did I say that? If this guy’s got a problem with me, I shouldn’t act like I’m enjoying myself.

“My name’s Pete. Listen—” he looked at his shoes. “You look real pretty.”

“Thank you.” Was he joking around? He didn’t seem to be.

“No, I mean that.” He looked up at me. “You look really pretty. Really beautiful.” There was a sincerity in his eyes that made me realize he was serious.

“Thank you. You look awfully nice, too.” Was that the right thing to say?

Pete walked a little closer to me and looked over his shoulder. “Julie, listen. Maybe we could do something sometime?” His voice cracked.

Was it true? Had this young stud just asked me out on a date? I must have been prettier than I thought.

“I dunno, Pete.” Actually, I did know. Doing this with Andrea was one thing, but going on a date with a guy was a lot further than I wanted to take this.

“C’mon Julie. We could see a movie, or have dinner, or something. I’d be fun.”

“Pete, I’m flattered, but I’m not gay.”

Instantly, I knew I’d said the wrong thing. Pete’s face darkened, then quickly molded into a grin.

“Hey, I’m not gay either, I was just messin’ with you, dude. Sheesh, you think I was serious?”

Pete smile was false, and his voice cracked. Even as he said them, he was backing out the door. It was obvious what happened. He wanted a date with me, well, with Julie, and when he was turned down he didn’t want me to think he’d been asking for real. Maybe I should have left well enough alone, but I felt it was time to mend fences.

“But if I was gay,” I said, moving forward, and touching his hand, “I’d love to go out with you.”

Pete looked like he was going to joke again, but then stopped and sort of blushed. “Honestly?”

“Handsome guy like you? Oh, yeah.” On a whim, I leaned in and kissed his cheek. I left him in the men’s room stunned, but smiling. I was smiling too.

When I returned to my table, Andrea and Heidi were sitting talking.

Andrea stood up when I arrived and pulled my chair out.

“There you are.” She turned to Heidi. “You know girls. They spend so much time in the bathroom.”

“Oh, stop it,” said Heidi. “She was probably just making herself beautiful for you.”

I hung my head and blushed. This was a little embarrassing, but at the same time, thrilling.

“Just touching up my makeup,” I admitted.

Andrea laughed and took my by the hand. We danced the next two slow numbers, with Andrea holding me tight. I felt safe. When Andrea kissed me, I gladly let her.

The rest of the evening was unremarkable. I danced with Andrea, and Heidi again. A couple of people asked to take my picture, but I demurely declined.

Soon, it was time for us to leave. We said our good-byes to Heidi and her friends, and began to pack up. I winked at Pete from across the room. He quickly smiled and ducked his head. We walked to the car.

Dawn was just getting into her date’s car. “Nice to meet you, Julie. Maybe we’ll see you around.”

I squeezed Andrea’s hand. “I’m sure you will.”

Dawn paused and motioned for Andrea to join her at the car. She whispered something into Andrea’s ear and they both laughed. Andrea then opened her car door for me and we sped off.

“What were you two talking about?” My paranoia was returning.

“Nothing.” Andrea gave me her debilitating grin.


“Okay. She said I ought to convince you to dress like that more often. Then you and I could share clothes.” Andrea was watching the road, but every so often she’d glance at me.

“Share clothes,” I chuckled. “It’d save money.”

“I doubt it. You’d probably be just like any other girl and want more things than you’d know what to do with.”

Pretending like I was joking, I picked up the thread. “Skirts, dresses, blouses—”

“High heels, pantyhose, lingerie—”

“Makeup, hair products, jewelry—”

“Bras, panties, a bikini—”

“Hold on, Andrea, I don’t think I’d fit into one of those.” Not without selling my soul, at any rate.

“Oh, I dunno.”

“What do you mean?” Gulp

“Some doses of estrogen, maybe a little plastic surgery—this time next summer I could make you into Miss Teen USA!”

My head absolutely swam. This was a joke conversation of course. But after so many years of secrecy, so many nights of denying how I felt, so many days of denying my desire to dress like a woman—it felt wonderful to talk about.

“Miss Teen USA?” I asked. “Well, you’ll have to give me lessons in deportment.”

Andrea laughed. “Not me! We’ll get Heidi to help you out. By the time we’re through with you, you’ll be turning down deals from Playboy!”

“Or accepting them!”

We both laughed, but it was strained. I wondered if I’d carried things too far, and Andrea was questioning my motivation.

We pulled up in front of her house. “Would you like to come in?”

“I think I’d better. My clothes are inside.”

“Oh, of course.” We walked to the door. “But you know, you don’t have to change right away.”

I didn’t ask why she wanted that, she didn’t question why I agreed. Soon we were sitting on her couch. Andrea had turned on the stereo and we sat in the dimly lit living room, listening.

“Are you sure your mother won’t come barging in?”

“She’s out of town.”

I shivered when Andrea put her arm around me. She was forceful. When she kissed me, her tongue went into my mouth. Her hands touched my body.

“Oh, Julie, you’re so pretty.”

“Thank you, Andy.” I stopped wondering what she was thinking. I just enjoyed the compliment.

“I mean it,” said Andrea. “You’re the prettiest girl I’ve ever met.”

“I wish,” I said without thinking.

We both pulled away and looked at each other in silence.

Finally, Andrea spoke. “Jordan, is there something you want to tell


“Is there something you want to tell me?” I came back.

Andrea smiled. “You first.”

“Andrea, please try to keep an open mind.”

Andrea kissed me. “I think I know what you’re about to say.”

She did know, didn’t she? She had me pegged right from the start. Nervously, I began. “I agreed to do this because I like dressing like a girl. I like being pretty. I like being

feminine sometimes. Don’t get me wrong, I loved being with you, but when I first called you, I was excited about the dress.”

Andrea tussled my wig. “You are so adorable! I thought maybe you were into this, but I wasn’t sure until tonight. God, you’re such a babe!”

I got goose bumps. “Really?”

“I wouldn’t go out with an ugly girl.”

“So is there something you’d like to tell me?”

“I guess it won’t come as a shock to you, but I don’t like wearing dresses. I don’t like being pretty. I want to be strong and in control. I guess when I go out; I want to be the guy.”

I touched Andrea’s cheek. “So–?”

She snuggled next to me. “So Julie, want to be my girlfriend? You’ll be my boyfriend in public, I guess, but in private, you’ll be the woman. MY woman.”

I lay my head on her shoulder. “And you’ll be my man. My boyfriend.”

“My mom’s gone every Thursday for girls’ night out with her friends. We could start buying you clothes, start getting you dressed up.”

“Oh, I’d like that. But, um, do you really think you’re the person to help me with that?”

“We can invite Heidi and Dawn.”

I felt uncomfortable. “I don’t want anyone else knowing.”

“It’s your choice, but I think you’d enjoy their help. You could really be one of the girls. They’ll teach you all about fashion, all about makeup, all about how to be girlish.”

“Let me think about it.”

“You do that, sweetie. In the mean time—” My boyfriend then shut

off the light. She held me in her strong arms, and kissed me.