Hair and makeup.

• Top: Maurices
• City Shorts: Maurices
• Boots: Payless (previously)
• Pantyhose: Just My Size via Walmart
• Necklace: Maurices (previously)
• Bracelet: Torrid (previously)

I felt really great in this outfit, but there are some things I'm not sure about. This button down is a little on the bulky side bordering on too big, but it can be cinched with the ribbon in the middle. I have seriously thought about removing that ribbon because I'm just not sure about it (As you can see, my bow tying skills are also a bit off as well...). If removed the ribbon would also be a pain to thread back through the fabric "loop" that contains it. I always enjoy everyone's feedback on my outfits, so definitely tell me what you think about this one!

In the previous post, Pamela from the awesome blog Call Me Ishmael asked a question: how long does it take wifey to do your hair and make up every time you take pictures and post? The answer is that it really depends. I normally wear my hair in a ponytail, and if I'm changing in the afternoon or evening and just going to wear one outfit and stay in, I'll just brush out my hair, but I do play around sometimes and try to fix my hair myself. I really want to be able to do these things for myself. (I also definitely intend to corner my stylist next time I get my hair cut and beg for lessons!) Likewise with the makeup. I want to learn how to do it myself. But most of the time for pictures I just brush out my hair and don't wear makeup (including the pictures in this post).

If we're going to go out though, I usually ask my wife to do my hair and makeup since she does a much better job than I do. I hope to get to the point where I feel comfortable doing it myself when I go out, but on the other hand, my wife does enjoy playing with makeup, so its not too much of a struggle to get her to help out there.

For makeup it normally takes about 15 minutes total. I start by shaving, and that takes maybe 5 minutes and then I take a break to let my face air dry. I should add that recently I have also experimented with using an epilator on my beard as well, but I still have to shave to get the hairs it misses. Fortunately, this experiment with hair removal went better than my last big adventure, I won't say its the most pleasant thing I've done though, but strangely enough it seems to irritate my face less than shaving (especially past the initial usage). I think I must have fairly sensitive skin. Anyway, with that done, we apply concealer for red spots/beard coverage, then use a loose powder foundation, blush, eye liner, eye shadow, mascara, and lip gloss. I could probably get away with less work on facial hair removal if I would use a heavier coverage foundation, but I don't really like any of the ones we've tried, and its been really difficult to match my skin tone on the heavier coverage too.

Hair takes a lot longer. Usually about an hour I think. I have fine, thick, straight hair, so it tends to take some work to get it to hold a curl. The last time my wife curled it in layers and used a spray gel before curling, and then hairsprayed it all when she was done. Its been tricky for my wife to figure out how to style my hair since her hair has a lot more natural curl.

And while this is not exactly what was asked, I do think I should add that the real time sink in getting ready is hair removal. Shaving my legs, chest, face, and armpits, plus using the epilator and tweezing just takes a while. I probably spend 4-6 hours a week on hair removal. So to go out for the evening like this post, I probably spend about 2 hours before getting ready, with my wife helping for about half of that time.

And of course my beautiful wife took the pictures for this post.

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. :)