Dinner and a haircut.

My outfit

• Dress: Asos (buy)
• Belt: Torrid (previously)
• Cardigan: Maurices (previously)
• Tights: JC Penney
• Boots: Nine West

My Wife's Outfit

• Top: Kohl's
• Skinny Jeans: Torrid
• Pumps: Nine West

The month of January was a bit of a rollercoaster, it had some major ups, and some frustrating downs, but mostly a lot of things to take up a lot of time. Hopefully my schedule will calm down for a bit. But this post is about a very big personal up for me. And since I said I would do Fabulous in February as organized by Hope and Melissa, I think this post will work into that quite well.

Early in January, I lucked into finding a seller on Craigslist who first had shoes in my size, and then clothes, and posted about that. For my second visit, I actually went dressed up, without my wife accompanying me, to see a person I didn't really know that well. That was a big deal for me, and a positive experience to be accepted by people in a situation like that. I'm sure I will post some outfits with the clothes I bought soon, but it turns out that was actually a good warm-up for the next weekend.

Our last haircuts were at Halloween, and we went in costume to get that haircut, and so I always had that to fall back on if anyone said anything. This time, however, there was nothing to hide behind. I dressed how I wanted, and thankfully, the hair salon we use is pretty cool like that. In hindsight, its hard to see why I was nervous, one of the stylists had a beard that went quite well with his dress. My stylist did a wonderful job on my hair, and that was a great start to the evening. And the outdoor pictures are at the park we've used several times before after the trip to the salon.

Next, we met up with two other female friends for dinner at an Asian fusion restaurant. I'll freely admit I was pretty nervous at this point, but I felt good about how I looked. We waited in the car until one of the friends arrived, and then headed in to get a table. Even though it was early, we ended up having to wait for a table, even after our other friend joined us. Dinner was good, and the waiter didn't say anything if he noticed.

Dinner ended up being a wonderful success. Ironically, the biggest shock of the evening was nothing. I felt pretty normal, and no one seemed to notice at all. We both enjoyed ourselves, got haircuts we were happy with, and had a fun dinner with some of our friends. I'm definitely looking forward to our next outing. I'm not sure when it will be, but the confidence boost I've gotten from my supportive friends and from all the wonderful support I've gotten from commenters and other bloggers.

And on that note, as part of Hope and Melissa's challenge, I'm supposed to list three positives about myself:

1. I'm honest. It's not always easy, and it doesn't always make getting along with other people easier, but I find it very difficult to deceive or maintain deceptions.
2. Crossdressing. I spent a good portion of my life feeling like crossdressing was the worst thing that had ever happened to me. I still have plenty of down days. Whether this is a "lifestyle", a "hobby", or whatever, this is something I have never quite been able to "not" do. But this is part of who I am, and its not going away, and now I'm trying to enjoy and make it a positive, constructive part of my life.
3. I like my legs. It's probably my number one physical feature that gets comments here, and I don't think anyone had ever said anything about my legs before I started openly wearing skirts. And I admit I can't always see it myself, but I do like my legs, and I will say that here.

And with that, I hope I'll get back to a regular schedule and finding out what I've missed on everyone's wonderful blogs. And of course, my awesome wife took most of the pictures in today's post.

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.

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.

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. :)

The Puffy Shirt.

• Top: Torrid
• Blue Tank Top: Maurices
• Vest: Maurices (here)
• Skinny Jeans: Torrid (previously)
• Boots: Torrid
• Dark Pink Flower: Maurices
• Book: Amazon

Okay, I'm excited about today's post. First: The weather finally started turning, and this is my outfit from Wednesday, and Boots! Yes, my first outfit with boots for the season, yay! :) I also just have to say something about the vest. I have wanted a vest for ages, and my wife and I went to Maurices a few days ago for a completely different reason, and I saw this vest, and well, how could I leave it there? It even has this really cute blue and gray plaid lining. When I got home I realized it would go perfect with this shirt, and you will be seeing this combo again.

I am also participating in Melissa's (from the amazing A Working Mom's Closet) Blogging for Breast Cancer aWEARness challenge. I won't be participating for the whole month because I just don't have that much pink in my wardrobe, and I also have a few days planned where I'm pretty sure I won't be wearing pink later in the month. The flower really is a dark pink, and my "pink" piece for the day. We had some discussion on how best to wear it, and my wife finally suggested the ponytail, and I think it works great there.

And yes, I'm outside. We went to a local park for these pictures. It was a very secluded park until we showed up, and then I guess everyone decided they needed to go for a walk or something. I'm glad I had a book to bury my face in. :) We ended up taking a lot of pictures, and we had some difficulty cutting it down, so I apologize for posting 5 pictures! And of course, my patient wife took the pictures today.

Spring into Fall.

• Top: Maurices
• Skirt: Maurices
• Flower Headband: Maurices
• Wedges: Payless

First, I have to say thank you to everyone for their response to yesterday's post! I definitely have some more fun ideas to try that incorporate more "menswear" into the blog in the future, now I just need those ideas to work out! And of course, as always I love questions to answers.

It finally feels like fall here, albeit a dreary rainy day type of fall, but I was unprepared with my pictures. So for today, you get something more springlike. I think I've been coming down with something for the past few days too, which probably means I put this together to protest dreary days and feeling sick! We'll go with that explanation. I may have to skip out on a post tomorrow but if I do, I'll be back on Thursday. I hope everyone is having a great day with as much fall as they can handle! And of course, my delightful wife took the pictures for today!

Under My Umbrella-ella-ella.

• Cami: Maurices (here)
• Hoodie: Maurices
• Skirt: Old Navy
• Rain boots: Payless (here)
• Bag: Target
• Umbrella: Crabtree & Evelyn
• Ribbon: from a spool of ribbon bought at Walmart

I don't always follow trends, but I do get inspired by them because cute trendy stuff shows up in stores. Well, okay, style blogging is changing that for me a little bit, but that's not my point. Some trends, like rain boots, end up making me want them all the more because I can't find something that works for me (well, in this case, by "work", I mean "fit"). So finally, I found this pair in my size, and *cough* 4 *cough* pairs of shoes later, my rain boots were safely in the mail. And the next day, I see this post by Kendi, and well, I thought "That's a pretty cute outfit and my boots will be here soon, I should try something like that!", but ultimately, the real credit for this outfit is a friend of mine who posted a complaint on Facebook a few days later. She was musing about the trend of all the people wearing rain boots with shorts and skirts, and pointing out that the water will just trickle down your legs into your boots. And I thought, "Hey, I was just thinking about wearing a something like that myself!" So for my friend, who I know is reading this post, I just want you to know, it was raining pretty hard, and I didn't get a single drop of water in my boots!

And yes, I'm outside!!! I do go out sometimes, this is actually my second trip outside since I started this blog (other trip is here even though I ended up not getting pictures outside). This is from yesterday: my wife had a surprise day off work, so we decided to do some shopping and meet up with some friends. I noted, to my surprising and unusual delight, that the weather report called for rain, so I was all about doing a quick change to get these pictures. And if nothing else, I promise I'll try to go outside again on Groundhog day to see if I see my shadow.

Okay, so yesterday Meli22 who is super cool and runs the totally rocking blog The Daily Insanity of a Fashion Addict asked some questions. And I have answers!

Is that your real hair, a wig, etc? How do you wear your hair when dressed this way vs. how do you wear your hair daily? Yes, this is my real hair you're seeing. I grew it out several years ago for many reasons, and one of them did include my interest in fashion. I didn't really accept this part of myself at the time, but hey, I was making progress. I almost always wear my hair up in a ponytail when I'm not dressed like this (also, I usually go without the ribbon too). In fact, this is one of the few times I've had my hair up for an outfit like this. A few months ago, in the search for a new hairdresser, I finally worked up the courage to ask for a slightly more interesting hair cut and got some layering put in, but alas, our most excellent hairdresser has found another job and left no forwarding address, so now I have to be courageous again. For special occasions, my wife helps me style my hair with a curling iron and other magical hair products (I'm still learning when it comes to hair and makeup!)

Okay, wow, if you're still here, I really appreciate it! Long post. Now no one will ask any more questions! Ack. Well, for the brave, ask away, I will still try to answer them! Okay, its also Friday (yay!), so I hope everyone has an absolutely wonderful weekend, and no rain (unless you want rain! I got my rain boots picture, so now its okay to be sunny with a slight chill so I can break out my other boots, tights I bought yesterday and everything else!). I'll be back with another post on Tuesday! And of course, my lovely (and patiently getting rained on) wife took the pictures (Hey, she got a box of chocolates too!).

French Friday

• Dress: Target
• Belt: Torrid
• Shoes: Rack Room
• Bag: Maurices
• Beret: a military surplus store(old)

A couple of weeks ago my wife and I went shopping with some friends, and one of our friends spotted this dress. I tried it on, and it was perfect! I haven't had a chance to wear it until today. I already had the perfect shoes(this pair is a wee bit tight though, I may have to give them up), and when I was putting it together, I remembered this beret I bought several years ago at an old military surplus store. I'm pretty sure the guy thought I was weird for wanting a beret, but I think it looks fab with this outfit. The glasses are just for style, but I bought them on the cheap from an online store to see how they looked the last time I replaced my prescription glasses(I normally wear contacts) and thought they would make a good accessory even if they didn't work out. I ended up with a different prescription pair but I thought this pair really added to this outfit. My wonderful wife was the photographer.