My extra late halloween post.

My Halloween Costume

• Top: Maurices
• Skirt: Torrid
• Petticoat: Torrid (here)
• "Knee" High socks: We Love Colors (here)
• Shoes: Payless (here)
• Other shoes: Gabriella Rocha via Zappos(here)

My Wife's Halloween Costume

• Top: JC Penney
• Skirt: Hot Topic
• Tights: JC Penney
• Shoes: Payless (here)

We decided that our costume this year would be "twin" school girls. Since the party was going to involve a lot of dancing, my wife and I chose to wear identical flats. On Saturday, my wife was going to wear a different costume (I guess that one will just roll over to next year), and I was going to wear a nice pair of Mary Jane style heels with this costume. I'm glad I took both pairs of shoes for the pictures, because I really like the heels and I've been saving them back from the blog for this costume.

Earlier this year, my wife and I found a really cool hair salon from a friend's recommendation, unfortunately after our one and only visit, we found when booking another appointment that our totally awesome hair stylist no longer worked there. Instead of asking for a different stylist, we just did what most people do when presented with a frustrating low priority task: procrastinate until its a high priority. We ended up not booking another appointment until last week. We had both arrived at the point of really needing a haircut and I had a brilliant idea.

Brilliant ideas are a scary thing right? Thankfully this brilliant idea didn't involve Nair, and turned out much better. We booked our hair appointment the day of the party we attended. When booking the appointment, I asked if it was okay for us to come in costume. They said yes. Emboldened, I sheepishly asked if it was okay for me to come in crossdressed in costume. Silence. Oops was the thought that flashed in my mind. Followed by getting put on hold. Apparently, that request prompted her to ask her superviser. But she said that was also okay.

Fast forward to the day of the party. We arrived at the hair salon, and the stylists later said they were impressed with my confidence. I didn't point out that sudden moves, loud noises, or even a stiff breeze would have revealed how thin my confidence truly was. I was aware that some of the customers in the salon were staring a hole in me. Thankfully it was a fairly light crowd that afternoon. We lucked out with our new stylists. They were awesome, and just like the first visit, the real shocker turned out to be that I'm straight. The stylist had neighbors and friends that are drag queens, so crossdressing was no big deal to her. We mostly ended up talking about clothes and shopping. The stylists did an awesome job with our hair, and we were both extremely pleased.

After the hair appointment, we had some time before the party for pictures in an obscure nearby park. Since this really is a special post, and because I was exceptionally happy with my makeup and hair, I cropped the pictures a little higher (um, we also forgot to get a few planned shots in all the excitement, and yes, my amazing wife took all the pictures, except the ones of her, I took those). Since I've discussed hair removal before, some notes on these pictures: I just shaved really good with a new blade, and then we used concealer, and covered it with a powder foundation. This actually worked great, but the concealer showed through in some pictures later in the night when we used the flash. The problem is partially that I don't like full coverage foundation, and we've had trouble matching my skin tone as well. It kinda gets expensive to keep trying different foundations too.

We ended up getting there a bit early, and the first batch of attendees were mostly not in costume. That did change as the night went on, but it was still surprisingly light on people in costume. We didn't know anyone at the party. Honestly, it was probably easier that way. However, I was not the only guy in a skirt. There was a guy who seemed to fit the comedian category, and there were a couple of guys in kilts (Seems like I missed a category in my previous post).

While we were sitting out a song and watching other people dance, I was approached by a guy who asked me to dance. At first I thought it was just someone being silly and I said, "Noooo". Feeling a little awkward, my wife did jump up and agree to dance with him. He seemed a little off put, so my wife later reported the conversation something like this:
Wife: "Oh, don't worry, you just surprised him."
Guy: "Him?"
Wife: "Yeah."
Guy: "Uh... that's a pretty good costume" trailing into nervous laughter.

One woman forgot that it was costume night and asked if we were dressed for a sorority function. Another guy was teaching some dance lessons and asked if we "ladies" wanted to join the lesson. We declined. One woman told me, "You make a convincing girl". It was becoming clear that while not everyone was fooled, that some people really did think I was a female.

The main event turned out to be the costume contest judging. They asked the girls to line up so they could "strut their stuff". Quite reasonably, I thought, not every girl wanted to "strut their stuff" and so there were some holdouts hiding in the audience. The girls in line started cajoling their peers to get in line too, most of them eventually acquiesced. Finally, they started calling out to me.

At first, I thought it was a joke, I really did. But it was apparent that at least some of them were serious. I finally told them that I was a guy in front of everyone, and after a bit of pause one of them pointed out that I was in a "very confusing state". After that, I decided a low profile was best and didn't join in the men's line. Honestly though, I was also hoping that if we were going to be judged that it would be for a "ensemble" costume since my wife and I went together. I also found it interesting that several of the guys who got in line were not in costumes, unlike the women's line. The comedian crossdresser ended up placing second, and in strutting his stuff, did some comedic overplaying of femininity, and that's not something I was interested in doing, so ultimately, I'm glad I didn't participate in the contest.

I certainly take it as a compliment that some people thought I was a female, and I even admit that I enjoyed it. I want to point out though, that even if I were go out on a "regular" night dressed to the nines, being counted as a girl is not my goal. In conversations with my wife, I mentioned that I felt that I was getting stared at a lot. My wife pointed out that it felt more like being out with one of her female friends from college, in particular, the way males were looking us over. On a lighter note, I have never danced in a skirt, that part was also lot of fun. The spinning was one of my favorite parts! A lot of the people who did figure it out were extremely cool about it. The night ended up being a lot of fun, and this year ended up being a lot different than last year.

A quick update.

First I just want to thank everyone for their incredible responses to the previous two posts! I really appreciated everyone's willingness to share their own hair removal horror stories in the comments on Almost one year ago... and I'm glad everyone enjoyed the humor in A Public Service Announcement: Crossdressers and Halloween. So check out those posts if you haven't already. I really enjoyed writing them and putting them together, and I have to thank my awesome wife for her help taking the pictures and reading drafts, and another friend who also helped with the editing.

This week has been crazy busy for us, and in addition to Halloween parties, and getting ready for Halloween parties, we have had some last minute non-Halloween events added to our social calendar too. And of course, you know, our jobs were still in the mix too. So this has put me behind on reading and commenting on blogs, but I fully intend to catch up, and I just wanted to say why I've been a bit absent from blogs this week! Our last party is tomorrow, and I hope to get a write-up of all the excitement plus pictures done either late Sunday or sometime on Monday.

Halloween has turned into a big deal for me because its partially become a holiday about legitimizing playing dress up. Having this blog has made it even more fun than last year for me as well. The end result is that I can go outside and not get asked a lot of questions. Er, that's not exactly true, I do get asked questions, but most of them have been pretty good natured. But I did want to share this article a friend saw a few days ago and forwarded to me: Can a boy be a princess for Halloween? Its actually a bit personal, because it rhymes with some of my own experiences. I asked my parents if I could go as a female cartoon character for Halloween once (I was closer to 10, although I don't remember exactly what age I was...). Unlike the kids parents, mine said no, and I didn't bring it up again. I picked another costume easily enough, but it did hurt. And their reasoning was similar to the some of the worries those parents expressed: They felt I would get picked on even more than normal (I was most often on the receiving end of bullying growing up already...). I think that was actually the last Halloween I went trick or treating though. My other costume wasn't a "success". The few costumes I've pulled together in adulthood haven't been a "success" either. Actually, the first costume I've felt good about since was my costume last year.

To this day, my parents still don't know about my interests expressed on this blog, and I intend to keep it that way. I'm pretty sure it wouldn't go well, and I don't want to find out. That's also why I don't want to say what character I wanted to go as, so please don't ask about that. And hey, if I ever find a suitable version of that costume (and I haven't!), I promise you I will be wearing it the next Halloween, and if I'm still doing this blog, I will post it here!

One last point. Several readers have mentioned wanting to hear from my wife. My wife is actively involved in this blog, and usually reads all the comments and posts in addition to taking the pictures, and proofreading drafts. This is one of our "together" activities as a couple, even if I'm often the more enthusiastic participant. I have asked her about doing a post on the blog, and its something I think she is willing to do, but it will have to wait at least a few weeks due to real life.

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.