I'm not a big fan of cross-dressing, frankly. There was a time in my life when Halloween just wasn't over until I'd seen a dozen men in various unfortunate female costumes. (Really, there's nothing quite as grand as an extremely hairy man dressed like Madonna in her conical bra phase, or an extremely dorky man dressed like Princess Leia, or - and this one still sends shudders down my spine - a six-foot-tall, three-hundred-pound man dressed like a female toddler, and visibly enjoying it far more than one would expect. No wonder I used intoxicants so much back then.)
But, as with every other thing under the sun, there are fan fiction authors that can make me read cross-dressing stories and like it. What follows is a list of such authors, and I suppose you could see it as either a hall of fame or a hall of shame. I'm inclined to the former point of view, actually, because these stories are damn good.
Best FF That Proves That the Phrase "Double Dog Dare" Never Really Loses Its Potency with Certain Kinds of Men. And, When You Think About It, Doesn't That Explain a Lot About the State of the World Today? A Dare's a Dare, by Speranza, aka cesperanza. Due South, Benton Fraser/Ray Kowalski. Cross-dressing is inevitable in this fandom, since it's canonical. Yes, for reasons probably best kept dark, the screenwriters decided that they really, really wanted to see Paul Gross in drag. On national television. And they got their way. In the process, incidentally, they discovered a concept that has the status of Archetypal Plot Device in comics fandom and canon: cross-dressing for justice. (Wouldn't the world be a better place if all canon authors took their cues from the D.C. Universe? Well, no, it'd be a totally insane place. But it'd sure have a lot of hypothetically straight men cross-dressing and hanging out in gay bars and necking and wearing purple Spandex bodysuits in public.) Fraser did his stint of noble transvestitism in the Real Ray Vecchio days, but when a man has worn a dress once in the interests of justice, well, what's to stop him from wearing it again on behalf of a friend? And don't say sanity, because Fraser's never had much of that. Plus, it'd be a total shame to let the dress just go to waste. Thank god Speranza didn't let that happen.
Best FF That Proves That Density-Control Is Not, as I Once Believed, a Lame Superpower. At Least, Not If You're Female and Minim Calibre Is Right About One of the Most Practical, Underwear-Related Uses of Said Power. Untitled, by minim_calibre. D.C. Universe, Grace Choi/Anissa Pierce. I refuse to apologize for having two DCU (motto: "Suppliers of the good crack since 1935") stories in this set. Didn't I just explain that the DCU (other motto: "Proud to be perverting another generation of socially inept adolescent males") is the Ol' Kentucky Home of cross-dressing? Plus, people really seem to want to put the Outsiders in drag, and I'm not the kind of person who can resist a trend. Well, actually, I can and do - anyone who has seen my wardrobe can attest to this - except when it involves well-written smut. (I am Porngirl! My secret powers include locating and analyzing sexually explicit materials; my not-so-secret weakness is my total susceptibility to good smut. I tell you, many's the time the universe has been destroyed because I was distracted at a critical moment by Spike blowing Xander in the library at Sunnydale High.) The truth is, this isn't exactly cross-dressing; it's more, um, cross-gender-role-dressing, or something. But I didn't think the boys should have all the fun, so I'm putting it in here. And no one can stop me from doing so, for I am Porngirl. Fear me.
Best FF That Teaches a Very Important Lesson to Young Adolescents. Namely, That You Should Probably Not Trust Your Friends. At Least, Not When They're Trying to Get You Into Partial Drag. A Wolf in Girl's Underwear, by musesfool. Harry Potter, Marauders-era, Remus Lupin/Sirius Black. Well, actually, it's sort of Remus Lupin/other Marauders, but mostly Sirius. Poor Remus. His friends are such a bad influence. (Well, they were; they're all dead now. Um. Moving back to more light-hearted topics.) In this story, it's double-plus poor Remus, because he has one of the more embarrassing first kisses in the universe. Even mine, which put me in mind of a mating squid, occurred in a place so public that I couldn't recoil and gag as I was naturally inclined to do, and therefore put me off kissing for years, wasn't this bad.* I wasn't wearing inappropriate underwear at the time, for one thing. (Bonus Seventeen-style tip for the as-yet-unkissed out there: never underestimate the importance of situationally appropriate undergarments in these situations. Pretty bras make all the difference! And they go on the girl(s) in the kissing duo, assuming a girl is present.) But there's an advantage Remus has in this story: his first kiss comes from someone who can actually kiss. Turns out that makes all the difference.
Best FF That Teaches a Very Important Lesson to Working Adults. Namely, That You Should Not Place Fetish Gear Purchases on Your Business Expense Report. Unless, of Course, You Can Get Away with It, or Get Hot Sex out of It. Spanky Pants, by derryderrydown. D.C. Universe, Roy Harper/Dick Grayson. You know, the title really says all that needs to be said about this story; I don't feel I can contribute a lot. But neither can I shut up - like I've ever able to keep quiet about great writing - so I'll just blather on for a bit, and we can all pretend that what I said was interesting. Deal? So. Cheerleader outfit. Arsenal. Nightwing. It sounds like it should be totally horrifying, and I admit that the mental image this story gave me has certainly scarred me for life. But it's so worth it, because this is just hysterical. And there's bonuses, too. For one thing, this story is educational. In addition to the above-mentioned lesson in business, we learn about Batclan communication styles, the importance of exploring one's sexual fetishes in supportive company, and the real reason cheerleader championships are broadcast on TV. (Assuming they are. But they aren't, are they?)
* Though it was, thinking back on it, fairly close. Did I mention that the guy in question had glue-like spit that mere toothbrushing could not defeat? Or that his apparent goal was to put his tongue into my esophagus? Or that I ended up with his makeup smeared all over my face? Or that pictures of this event appeared in a newsletter later sent to my parents? Or that I was 12 and the guy was 16, which facts were mentioned in the caption in the newsletter, thus provoking some fascinating discussions on the homefront? Yeah. Not the best experience ever, right there.