Almost one year ago...

• Costume: Torrid
• Knee High Tights: Torrid
• Pumps: Torrid

Last year, we were invited to a Halloween party some friends were hosting, and I finally took the opportunity to explain to my friends my interest in crossdressing. These were not the very first friends I had told, but they were among the first. I decided I was going to take advantage of that Halloween party to go out and enjoy myself and properly dress up. Prior to that party I had never worn makeup, and never allowed any pictures to be taken of me while I was dressed up. And I hadn't really been outside properly either. It was a night of many firsts for me and my wife, and ultimately it was a lot of fun, and I realized how awesome some of my friends really are. But it almost didn't happen. And so today, I wanted to tell that story. With time, distance, and a happy ending it's lot easier to laugh at now.

I've heard it said that good judgment comes from experience, and experience comes from bad judgment. This post is about bad judgment.

We decided that for my costume, we would try to do the best possible job we could, and that included makeup. Now, I just want to add that at this point, I had never worn makeup before, and while I do wear it on occasion now, my wife usually does my makeup for me (although I am learning to do my own makeup), and it's not my favorite aspect of dressing up. But I have to say, I love what it can do for my pictures. Oh... right... I crop them all before posting, er, so everyone will just have to trust me on this one. ;) Anyway, so the single biggest "problem" I have with makeup is actually one that I suspect is less common: Facial hair. A 5 o'clock shadow is not usually the effect I'm going for, whether I'm dressed in a masculine or feminine manner, but it's definitely more frustrating for some of my feminine outfits. I have no ill will toward facial hair or body hair in general, on anyone, I just have a preference for less of it on me at times.

Enter bad judgment. Having previously experimented with waxing one leg (Yes, one leg. We ran out of strips, and I ended up shaving the other leg for two months to "even" things out...), I decided that waxing my face would be a brilliant idea.

Now, some part of my brain did have some concerns with this plan. The chief concern was that my facial hair wouldn't be long enough. So I started growing a beard just before Halloween to solve that problem. I also had visions of waxing gone awry and creating an ill placed, and very unfortunate bald spot on my head. And so the day before the party came, and we were in the bathroom, and my wife had applied the wax and placed the first strip on my face, and pulled... (Frankly, I think my wife enjoys this part too much...)

If our neighbors heard anything, they never said anything to us. I think the worst though, was that not a single hair came out. Not one. While the pain was unpleasant, Everything Was Still Okay. I had a Plan B.

Enter more bad judgment. It was now the next morning, I had already cut my leg shaving and I was starting to panic about the timing and how things were going. After a quick trip to the store, we bought a bottle of Nair. After reading and rereading the directions several times, I applied it to my face.

About 10 minutes later, I was washing it off. My face was burning. A lot. Did I mention the smell? Also the burning?

In addition to the "5 o'clock shadow", my face was now bright red and in intense pain. I was hiding in the bathroom, crying in the bathtub, telling my wife to call our friends and say we weren't coming. My wife called our friends, and after passing the phone around and talking about it all, our friends were pretty understanding about it all and had some suggestions and reassurances. So after the phone call and some time to calm down, we resumed getting ready.

I finally broke down and shaved my face with a razor. I have had razor burn before, but this was a whole other level of burn. This was the most unpleasant shave I have ever had. I didn't think shaving could go so wrong. But it was finally done, and I was relatively clean shaven and very red faced (but hey, as everyone told me that day, "that's what makeup is for..."). Also, did I mention the burning? Okay. I just wanted to make sure.

We ended up going to the party and having a great time, and I was even okay with several people taking pictures of me and my wife in our costumes. (Uh, now about tagging them on Facebook... that's a different matter...)

Since then, I have learned more about how to cover a 5 o'clock shadow, and hopefully my makeup this year will be the best it has ever been. (Again thanks to my wife's abilities, certainly not my own...) And there will be lots of pictures, and I will post about everything we do later this week. But for today, I thought everyone would enjoy seeing last year's costume, my first feminine costume, and even the first pictures of me wearing women's clothing ever, and have a good laugh at my story of bad judgment. This year, I plan on making ALL NEW mistakes. :)

A Public Service Announcement: Crossdressers and Halloween

In this edition of our award winning documentary series on Halloween, we will be discussing the elusive straight male crossdresser in his natural habitat. This is one of our many, many documentaries on Halloween, so please take a moment to consider checking out some of our other award nominated productions, Vampires: Traditional or Sparkly, a field guide for the novice, A Dog Whisperer's Guide to Housebreaking your Werewolf Roommate, A plea for brains: Am I a Zombie or just drunk? Does it even matter?. And don't forget our famous expose, Rainbow Pooping Unicorns and Skittles: An Inconvenient Truth.

Now, as many people are aware Halloween is a time when the creatures of myths and legends take to the streets. Most of them are harmless and merely taking the opportunity to socialize the one time of year no will notice. In this guide, we will be discussing the many types of straight male crossdressers that might be encountered on Halloween. As you will see, the straight male crossdresser can often be found hiding where you least expect.

Types of Straight Male Crossdressers

The Superhero - Let's face it, this crossdresser is subtle and suave. Going as the manliest of manly costumes... that requires tights? His secret is safe, since no one will question Superman, but he has subtly and deftly taken the opportunity to combine his interest in women's clothing with a costume no one will question.

The Gambler - This type of crossdresser takes comfort in the well worn genre/plot trope of the bet-gone-wrong. Stories of bets or actual elaborate bets will be concocted by this crossdresser to be lost, granting him the cover of plausible deniability. And since he is a sporting chap, he will be "forced" to indulge in crossdressing. Hey, he lost the bet, its only "fair" that he pay up.

The Comedian - This crossdresser may be quite skilled in the application of makeup and the selection of clothing, but for the sake of Halloween, attires himself in the "dude in a dress" stereotype and does a horrible job, with clownish makeup, ill-fitting clothes, and badly placed balloon cleavage. After all, he's so bad at it, he couldn't possibly enjoy it, and hey, its all for the gag, right? Right? RIGHT?

The Sexist Poser - Taking his cue from Briar Rabbit, this crossdresser's sexist statements about women's clothing is really a facade. It's his way of saying "don't through me in the briar patch". He will continue to push his unwitting female collaborators until he succeeds in creating a "It takes a real man to wear a skirt" moment, in which his taunting and snarky comments give rise to the challenge that he don women's clothing to "prove his manhood".

Rocky - Horror Picture Show of course. This crossdresser uses the cult popularity of this movie to crossdress in the manner of its hero, Dr. Frank-N-Furter, and thus disguise his true intent. One must be careful however, since this category overlaps with Space Aliens who are visiting from Transsexual, Transylvania. Please see our documentary on extraterrestrial, Long Distance Dialing Plans and the Andromeda Galaxy, for more details.

The Winner - This crossdresser takes no prisoners for Halloween and just goes out in his finest feminine fashion. This crossdresser will frequently seek out costume contests, as the prize money and competitive aspect provide cover for his fitted clothes, nicely done hair, and expert makeup. However, a quick calculation of the costume cost will frequently reveal that the prize money is a tiny fraction of the expenses he has incurred. If challenged, this crossdresser may resort to vague speeches about a "job well done", and "anything worth doing is worth doing right" and wander off muttering a litany of excuses until he can find conversants who are less inquisitive about his attire.

Possibly Confused for a Crossdresser

Bank Robbers - Despite their predilection for using pantyhose as a mask or even donning drag to confuse the hidden cameras, bank robbers are not known, in general, to enjoy crossdressing anymore than they are likely to be former heads of state.

Drag Queens - Drag queens are, at their core, performance artists, and predominantly homosexual. While the occasional straight drag queen, and even the ever elusive female drag queen are known to be encountered, drag queens are very likely providing you with a creative form of entertainment, celebrity impersonation, and poking good natured fun at social norms of gendered behavior.

Eighties Hair Metal Bands - These are not crossdressers. Currently, they are an unclassified specimen, which after a rise to prominence in the eighties and sudden mass extinction event have recently seen a recurrent rise in their numbers. This specimen is also known to destroy hotel rooms. Just enjoy their music and don't ask too many questions and everything should be fine.