Chrossdressmas, Parts 4 & 5: Plans, Trans & Outcomobiles

I’m not even going to pretend that’s a good post title.

I totally and completely apologize for not posting this sooner. I don’t even have a good excuse for the delay. Yes, Hurricane Sandy has taken its toll in my area, but where I live hasn’t been hit very hard, and tomorrow will be my third consecutive day with work cancelled. Instead of dressing up, writing or doing anything productive I marathoned the remaining Doctor Who episodes I had yet to see. That’s all finished, though, so without further adieu…

Welcome to parts four and five of my Halloween/Crossdressing feature. This is the penultimate and ultimate post, as I’ve decided to combine the two due to my tardiness in posting, and the common thread that runs between both parts. In part four I write about my plans for unveiling my crossdressing on Halloween, and in part five I will discuss how it all actually went down.

Part 4: Coming Out On Halloween


End of the Night

Every year my girlfriend and I throw a Halloween party. If you’ve read some of my previous posts, you already know that this would be my third consecutive year crossdressing. The first two times no one takes you seriously, especially if you don’t do it very well. The third time, you’re faced with a choice – no one thinks a three-times crossdresser is joking, so if you’re going to do it, you should do it well. Otherwise, your secret is out to everyone, and you’re also not impressing anyone.

This year, I put a lot of effort into my costume, or rather, my new lifestyle in general. If people had questions, I would answer them all seriously.

First, give them a choice: Do you want the P.C. answer or do you want the serious/blunt answer? This comes into play with questions like, “What did you do with your penis?” or “Can I touch your breasts?” I also assumed people would ask the same questions most others face when they come out. The “Are you gay?” and “Do you want a sex change” fare. Those I would answer quickly and honestly.

At one point I dabbled in writing up a quick one page crossdressing FAQ that I could share with anyone who had questions. I decided against this, as it made it obviously that the issue was clearly something I was nervous about, and had put a lot of thought into. At a party you’re holding, it’s always better to play things casually, even if that’s not how you feel on the inside.

In this aspect, I also decided that I would not broach the subject myself. The point of the party is to have  a party, not to serve as a coming out. If people don’t ask me what I am or why I’m dressed up, I won’t bring it up either. Crossdressing for the third party in a row or not, it’s still Halloween. Maybe it’s just a strange kink, better left unexplained.

So my policy would boil down to:

  1. No ask? Don’t tell.
  2. Honesty when asked for, otherwise brush over the unimportant details.
  3. Play it cool.

Following these three rules would hopefully lead to a peaceful, fun, and freeing night. And if they don’t work – when in doubt? There was alcohol.

Part 5: The Party


Another shot

So how did it all happen? In a word, uneventful.

This years part, for lack of a better word, was small. In the past, parties have had around fifteen people, which is a good amount considering the size of our apartment. Due to weather, health, other parties and an ill-timed Aimee Mann/Ted Leo concert, this year’s party only had half the number of guests as usual, and was therefore more of an intimate gathering than usual.

This did not hinder me, though. My costume worked as planned, plus a few extra pieces of tape and safety pins. Of the guests that did come, two of them already knew about my crossdressing, and the rest simply did not ask. That is to say, they did not ask why I was dressed up. When asked what my costume was, I replied, “A crossdresser on Halloween” and left it at that. I figured that left things open to interpretation or further questions if curious, but apparently my answer was good enough.

I think it was pretty clear that a good deal of effort had been put into the costume – for example, I didn’t just happen to have size twelve boots laying around, or a high-quality wig. If people had any questions, they were all kept to themselves, and short of complementing my costume, no one had anything else to say about it. It was nice to hear from some of the girls, however, that I was pulling off a dress that they couldn’t.

In terms of costume itself, I was very happy with how it came out. I wish I had some more time to spend on my make up. I also want to give props to my girlfriend, who did an excellent job on my eye make up. I’m going to have to ask her for tips on how to replicate that look in the future.

The pictures that I have, unfortunately are from the end of the night, after people had left. I think the costume overall looked a little bit better earlier, but c’est la vie. There’s always next year. All in all, I’d consider it a successful and uneventful night of crossdressing.

Do I wish I had “come out” more clearly? Maybe. I think, though, that I got the point across and would consider it safe to say that more people know now than did a few days ago.


So where do I go from here? Halloween parties aren’t for another year. As a crossdresser, I’ve been looking forward to Halloween since July. Here a few things I hope to look forward to that are not Halloween in the coming months.

  • Going out in public – for real – not just walking around the block. I want to go to a bar with my friends. I will do this. It is new #1 goal. It will happen before the end of the year. Hopefully.
  • New Years – I’ve always wanted to dress up for New Years. I don’t know where this year’s New Years party will be, but depending on the location, and who throws the party, it’s definitely an option.
  • Telling more people – there are more friends that I would like to tell, and eventually my parents.
  • Just getting better at crossdressing in general. In one of my first ever posts I likened crossdressing to a sport. In this case, there’s always room for improvement, and I can think of hundreds of ways I’d like to get better.

I will save elaboration on all of these for other posts. Don’t want to stray too far here. I will say, it was a lot of fun writing about Halloween. Next year, I don’t think there will be any multi-part feature – that’s kind of a once in a lifetime thing. As for next year’s Halloween? I eagerly await it.

Happy Chrossdressmas!


More Pics on Flickr

Hello all! I know, I’m past due for an update, and the last two parts of my Crossdressing on Halloween post collection. They’ll come soon. A bit exhausted right now, from running a 10 mile race yesterday, and hosting a Halloween party. There are way more pictures on Flickr for mutual contacts – you add me, I’ll add you ASAP.

For now, though, I’m going to sit back, eat some pizza and enjoy the fact that inclement weather has closed my school for tomorrow. The only people that want school closed more than the students? The teachers.

Enjoy your Halloweekend, all!


Chrossdressmas, Part 3: *Some Assembly Required

This is the third part of my Chrossdressmas series, which goes into way too much detail about my love affair with Halloween, as a crossdresser. The first two parts of the series deal with my past experiences on Halloween, and what Halloween means to me as a crossdresser. With the third installment, I will discuss this year’s Halloween costume and how it came to be. Let’s begin.



She’s more muscular than I am

As I mentioned in an earlier post, I began thinking about Halloween in July, as soon as I came out of the crossdressing closet. Within a week of telling my girlfriend I had a folder in my bookmarks that was filled with a number of different crossdressing ideas.

My first plan was Supergirl – one of the few female superheros with long sleeves. This costume could be put together pretty easily, but wasn’t very do-it-yourself, which is something I prefer in a Halloween costume. I still like the idea of a Supergirl costume, but I decided it wouldn’t work this year. Now that I was out, I wanted to do something that could show off how successfully I could do it. (This is debatable, opinions to yourself please.)

Costume: Dress

6pm Dress

Nice, but not curvy enough.

I moved on from Supergirl to simply “classy Halloween dress.” I knew I wanted it to focus on the colors black and orange, and I also wanted it to show off some of my curves. I narrowed it down to three different dresses, and eventually purchased a dress from The dress, pictured left, arrived, and was quite nice, but in the end I decided it didn’t do enough for my end. If it’s Halloween I’m going for wow.

From here, I moved onto to American Apparel, which I now known is known for selling clothes that fit better on trendy hipsters. I am not a trendy hipster. I did however, purchase a dress from them, that was revealing and showed off curves. I loved the plunging neckline in the back and front. (Note – the dress I purchased was in black, not sure what color that link actually goes to…) The only problem with the dress? With my breastforms, the bra is necessary and it shows quite obviously along the back. I’d met with failure once more.

Fortunately, American Apparel has a very similar dress, which I posted a picture of earlier from their site. The is short, black, with a plunging v-neck and a high back. It’s just a bit longer than the original American Apparel dress and it looks like this.

The Final Dress

This Is It

So at the moment, less than a week before my Halloween party this is the dress I’ve settled on. Plans can still change, though. I still like the 6pm dress, and if it wasn’t for the back of the first American Apparel dress, that would be my choice. I do have an invisible strap bra, but it doesn’t work very well with my breastforms and it isn’t very supportive. I’ve still got time to figure things out, though.

Costume: Belt

The costume, of course, needs some black and orange, and what better way to include some orange than with a waist cinching belt?

Finding a decent orange belt has not been easy. I’ve gone through three different belts, and finally the third belt is the one I’ve settled on.


Not Orange Snakes

The first belt has a bit of an orange and white weave, and just didn’t feel right. It looks a little bit too springy, and it didn’t close very strongly. A cheap belt off of ebay, and ultimately a mistake. The second belt is too short and too skinny – also very cheaply made.

The third belt is essentially a larger version of the second belt. I didn’t want a skinny belt – I didn’t like the way it looked. This ended up being the right call, as the thicker belt looks much better with the dress. In addition, it fits much better. It’s crazy how different sizing a belt for myself en homme and en femme can be.

Costume: Shoes

Just like everything else, my shoes for this costume has gone through phases. This one will probably come down to a decision on the day of the Halloween party.

The first shoes I ever bought myself were cute little Mary Janes from Payless. I thought this would be functional, and also an option for Halloween. This is still the case, but this was all before my mini-obsession with boots. The next option is my calf-high black boots. These look good with just about anything, and love the idea of a short dress and high boots. These are probably my top choice right around now. I also purchased my first pair of heels as an option for the costume…. but I also realize heels are extremely uncomfortable, even if they’re considered the comfortable heels.

All Shoes

All Shoes

No matter which decision I make, I’m pretty confident they’ll look alright.

Costume: Jewlery

For necklace, I think I’ll be wearing a cute black choker that belongs to my girlfriend. For earrings? Check this out:


Trick or Treat

The earrings are from Ashla Designs on etsy. Do note – I ordered the earrings as clip-ons and they were sent as regular earrings. I contacted the maker, and she’s sending me replacements, and an extra pair of clip-ons to apologize for the inconvenience. Once the replacements arrive, I will have no problem giving etsy and Ashla Designs my vote of confidence (and high seller marks.) Very good customer service, and awesome looking earrings. Win-win.

I also have an orange flower hair-clip from Claire’s that I’m excited about trying out. Forgot to snap a picture of it – sorry!

Costume: Make-Up

Orange lipstick, dark eye-shadow. I considered finding a place to get my make-up done professionally, but I can’t find anything extremely local, or anything fairly cheap. I’ll do the make-up myself, or perhaps get a friend to help me out. We’ll see.

Everything else for the make-up will be pretty typical. I’m going to get a professional shave a few hours before hand, so hopefully I’ll be able to more successfully hide any stubble.


That about sums up my costume. Finished pictures will obviously be posted next weekend after the party. I’m excited to try everything out all once… I’m also very nervous about dressing up around a lot of people who have never seen me dressed up before. I’ll go into much more detail with that next week, though, as part four of my Halloween expose is about my non-dressing plans for Halloween. This will talk much more in-depth about who I will probably be coming out to, how I’m going to do it, and how ridiculously nervous I am.

All in the name of crossdressing!

Now, though, it’s time to try out my new wig. Wearing it en homme I just look like a confuses samurai.



  • Taking a walk around the block, dressed, with your girlfriend, is the most wonderful feeling in the world.
  • Crossdressing is more competitive than I thought before I started – every time I think I’ve done a good job with something, I see someone else has done it waaaay better.
  • Payless UGG knock-offs are awesome and comfortable. And look great with leggings.
  • I have a new lace-front wig coming in the mail soon. Not quite sure how it works, but I’m hoping it has more styling options than my current wig. Does anyone know if it’s possible for a human-blend wig to get split ends?
  • Halloween costume is coming together nicely. Going to need some gorrila tape to keep some articles of clothing in place. Expect a pictorial Halloween costume themed post this weekend.
  • I took a great picture tonight, that I wish I could post unblurred – the below will have to do, though. The clear photo, and more, can be found on Flickr. (Contacts only – add me and I’ll add you.)
  • Number of propositions received since I started crossdressing: 3.
  • Number of propositions received in over twenty-five years of male form: 0 (not including girlfriend or exes.)
New Necklace

If you squint, it looks kind of clear.

A few more days until the weekend! Looking forward to a relaxing weekend of crossdressing, football and pizza.

The Sometimes Mommy

I don’t have children, but when I do, I know that my crossdressing is definitely going to be a hot button issue.

Now is not the time for me to make any decisions about what role crossdressing will have in my or my children’s life when the issue arises. That doesn’t stop me from thinking about it from time to time, though, and today I had an idea.

There are a number of books for children with one parent, no parents, or same-sex parents, but I don’t think there are any for kids with crossdressing parent(s). That’s where this comes in:

The Sometimes Mommy

The Sometimes Mommy

The Sometimes Mommy is a children’s book I will one day write that will help children understand why their father crossdresses. It will deal with issues such as the child’s involvement in the crossdressing, the role the parent has when crossdressing, and how children can (should they choose) explain their parents crossdressing to other people.

Obviously I haven’t written the book yet, but when I do, expect it to be a huge hit. There will probably be a number of en femme book signings, day time talk show interviews and an adult companion-book. This will spin-off into a TV show (sitcom or children’s cartoon), coffee table book, and eventually a movie starring some as-of-yet-not-casted SNL pretty boy who is now trying to make it in the movie business. (The film will probably flop, but I will clash with the director over creative differences.)

Pat Robertson, if he is still alive, will condemn me to hell. Upon his death, it will be revealed that he was a closted crossdresser.

In all seriousness, should I be blogging X number of years from now, I’ll probably write ad nauseum about the subject. For now, you’ll just have to settle with a clip-art cover of The Sometimes Mommy.

A Family Affair

In a comment in an earlier post Randa Lane briefly referred to the fact that no one in her family knew that she was a crossdresser. I’ve always given thought to finally talking about my hobby with my family, but before her comment I hadn’t considered writing about it.

Here’s a brief summary of my family, before I go into the specifics about how I think each would react if I told them.

Abstract: My nuclear family consists of five members, including myself. My mother and father are both in their early fifties. My father grew up outside of New York City, and my mother grew up on Long Island, in the same town my family now lives and where I grew up. I have a younger brother who is almost done with his undergraduate degree, and a younger sister who is now beginning to look at colleges for herself.

My family is very middle class – my father is self-employed and works in the communications business, and my mother is an office manager in a doctor’s office. Politically, I think it safe to say that my family is left leaning all-around. Socially, my entire family is in favor of gay marriage, despite the fact that my parents are still slightly skeeved out by it. My parents can be a bit backwards about things – they like to consider themselves socially progressive, but would probably get upset if a black family moved on to their block. My brother and sister are both in favor of gay marriage and don’t really care about race. My brother and his friends still throw the term “gay” around pretty freely as a derogatory term, but I think my brother knows that it’s wrong, only doing it to sound cool.

The topic of crossdressing hasn’t, as far as I know, come up in terms of my family.  I don’t think there’s a history of it, and if my father or brother have ever experimented, it’d be news to me. Whether or not they know about me – I have my paranoid suspicions – but I think I covered that briefly in a much earlier post.

My Father

I don’t think my father is the first person I’d tell, but I’ll go in descending age order. My father considers himself a staunch democrat and considers himself accepting of almost anything not inhumane. One of his best friends growing up came out of the closet in college, and my father has remained close with him his entire life. He was actually named my godfather, although over the years we’ve never kept in great touch. In terms of LGBT issues, I would consider my father fairly ignorant, but mostly open-minded. He doesn’t know much about the issues, but if it tugs on his heartstrings (and most things do) he’ll be a champion of your cause. He’s a compassionate, thoughtful individual who desires only to include others in the things he does, and to a fault expects him to be included in what others do.

It’s this bigheartedness that makes me think that he would be the more accepting of my parents – but I don’t think it would come without a number of questions. For one, he would certainly ask the same questions most people do. Does this mean your gay? Do you want a sex change? The usual line of questioning when you come out to someone as a crossdresser. I would answer him honestly, and his questions would probably consider. He’d be interested in my history – how and when I started, why I do it, etc. and I’d be completely honest with him. I have a policy of not lying to my parents (or most people in general) as lies are generally difficult to keep track of, and honesty builds stronger bonds, creating mutual trust. Honesty is just easier.

(I realize the hypocrisy here, of maintaining a policy of honesty, but keeping my crossdressing secret. I think of this more as lying by omission. No one’s ever asked me if I was a crossdresser, so I never bring it up.)

The problem with my father would be his sharing. He likes to talk. To everyone. I’m sure he’d know someone who knows someone who knows another crossdresser and would immediately want to share with them. And everyone on Facebook. It would just slip into conversation, casually, perhaps without him even realizing it. I know he would promise to keep it a secret, but I don’t know if he could keep that promise.

I have to consider an alternative, though. My brother is, as far as I know, straight, but has never been with a girl. I’ve discussed with my dad the possibility that my brother could be gay, and it is always met adamantly with a “no.” As if that’s not even an option. I know my father would love my brother and myself, unconditionally, but I could see my crossdressing as something difficult for him to accept initially, and perhaps over time. I don’t think anything, though, could ever sever our strong relationship.

My Mother

I would tell my mother before I told anyone else. This, despite the fact that I think she would be less accepting than my dad. The reason for this is because my mother has always been easier to talk to. Our time together has always lent itself to more in depth and personal conversations. Growing up when I had problems with relationships, I would go to my father. When I had problems with myself, I would talk to my mother.

Despite my father’s ambitious outward compassion, I think it is my mom who actually spends more time in serious though about other people – especially her children. When it comes to her kids, my mom has never put herself first.

I think if I told my mom, she would try to remain open-minded, and ask similar questions that my dad would. I think she would have more in depth questions that string together, with more specifics in terms of how it affected me growing up, and how it affects me now. I think she’d be more interested in how far I take crossdressing, and is more likely to ask to see pictures than my father.

Despite this open-mindedness, and line of questioning, I don’t know if she would be accepting. My mother likes to consider herself socially liberal, and understands why I and my father are, but she grew up in a slightly more conservative household, and sometimes has difficult accepting lifestyles that differ from her own. In another life, where my mom did not grow up on Long Island, I could see her as an activist for women’s causes, and even other minority groups. Instead, though, she champions the causes of her children, and friends who have been wronged, even if ever so slightly. She knows how to fight, and more importantly how to win a fight. I digress.

My mother would ask, and she would listen, but in the end – I just don’t know. When given the option to attend my gay godfather’s wedding my mother scoffed, “I don’t want to see two men kiss.” Strange words from a woman who supports gay marriage. Now, I know being gay is different than being a crossdresser, but despite this, they’re two lifestyles that are linked in terms of social rights and if my mom can’t get behind two men kissing, could she understand one’s desire to wear women’s clothing? And how would she react to the fact that this all began with her clothing. If she asked, I, once again would not lie. My mom is a social creature, and would probably want to discuss this with her friends, getting their opinions. I think this would be a terrible idea, as her friends are far more close-minded than she is. She might also want to see a psychiatrist, to get a professional open. I would suggest this to her, and she would probably be open to it.

In the end, like my father, I think my mother would love me unconditionally. I could murder someone, and the love would be there. Besides, what’s a few bras between mother and son?

My Brother

My brother would probably be the last person told. To be honest, I’m not sure if there would ever be a purpose in him knowing, other than no longer wanting to lie by omission. My brother is a mysterious creature. He didn’t do too well in school, but I don’t blame him, as he worked hard despite a learning disability. He’s in college now, which may or may not be a mistake, but I think in the end it will do him a world of good.

You see, I think there are two sides to my brother. My true brother, and the person my brother projects. When you talk to him one on one, he is inquisitive, open-minded and even sometimes insightful. When he’s with his friends, however, he becomes “just another one of the guys” prone to wearing wife-beaters, drinking shitty beer, and saying and doing stupid things. It’s this conflicted personality that I think has led to my brother being friends with many fraternity members, but not actually joining one himself. I hoped that with age he would become more “true brother” but so far, nothing.

(Fair warning – my idea of “true brother” might just be one I project on to him – the brother I wish he was, not the brother he actually is. That’s a post for another blog, one that doesn’t actually exist.)

Moving on, I reiterate, I don’t think telling my brother would accomplish anything. His response would most likely be in the form of lack thereof. He’d probably shrug and ask why I told him. He’d probably then do some research, but never actually confront me about it again. My brother and I have enough distance in age, that conversations about girls, sex and all those other brotherly things, never actually occur between us. I try to talk to him, but he doesn’t like to share his personal life with me.

I do know this – my brother has certainly become more liberal in college, and most definitely supports gay marriage. I don’t think he really knows anyone who is gay, but he understands that there’s no point in keeping someone from being happy. He’s not going out of his way to support gay rights, but he would certainly never do anything intentional to hinder them. If my brother ever finds out I am a crossdresser, it’s because everyone else in my family knows, and then, hey – why not?

My Sister

My sister is in High School and is definitely the most open-minded of my siblings. She’s popular, but a free spirit. She knows where she stands on social issues, and isn’t going to be swayed by anyone. She’s strong in her liberal convictions, but ignorant of their history and their importance. I don’t think any of this is uncommon amongst high school students.

The age gap between myself and my sister has created a relationship that is actually very strong. I like to consider myself a good big brother, and she looks up to me. I don’t think telling her while she is in high school is a very good idea, though. High school students cannot keep secrets. I don’t think she’s mature enough to understand why someone crossdresses, and she’s very liable to take my crossdressing the wrong way. Interpret it as me being gay, or wanting a sex change, despite the fact that both these things are untrue. High schoolers have a way of jumping to conclusions. If, however, I did  tell her now, I’m sure she not only be accepting, but also an eager participant, wanting to know more about it, especially the physical dress-up aspects.

When she’s in college is another story. Give her a few years, and I think she could mature enough to handle the situation. This is all supposition, though, so we’ll see where she is in a few years. Like my brother, I think college will be good for her. Either way, if she ever knows, my parents will both already know, and it also won’t be for another few years. Finding out your big brother is a crossdresser is not only a bizarre burden to place upon a stressed high schooler, but also an unnecessary one.


So there it is. Writing this has forced me to give more thought to when and if I’ll tell my parents. And I think it’s more a matter of when. I think it’s important to be honest with them, and I think the broadening of their horizons will ultimately be good for them. It’s also important to me that I’m accepted by the people I care about. But isn’t that the case with everyone about everything?

Chrossdressmas, Part 2: The Meaning of Chrossdressmas

This is the second part of my Chrossdressmass series, which analyzes my relationship with Halloween as a crossdresser. The first part of the series catalogs my earlier, less successful forays into crossdressing on Halloween and can be found here. Part 2 will follow what exactly Halloween means to me as a crossdresser, and what I think it can mean to other crossdressers. After rereading some of my earlier posts, I think I should warn: I’ve gotten awfully assumptive these days.

Me (A semi-outed heterosexual MTF crossdresser)

Crossdressing has meant a number of different things to me over the past few years. The past two years when I crossdressed on Halloween I did so as a joke. At least, that was the spoken explanation. To myself, a then closeted crossdresser I looked at the day as an opportunity to express myself in public physically, but not mentally.

Halloween is all about costumes and glamour. It’s the day where everyone wants to dress up and appear as something they are not. Except as a crossdresser this is really how I feel almost every day. There isn’t a day that goes by where I don’t wonder how I would look in a pair of boots, or in a certain dress. Most days, before coming out, figuring out just wasn’t an option. Halloween served as a built-in pressure release for closeted crossdressers so that once, every year, they could express themselves and nobody would think anything of it.

In terms of my relationship with my girlfriend, crossdressing on Halloween also served as a way to test borders and boundaries. I used Halloween to gauge my girlfriend’s reaction to crossdressing. I will admit, it’s tough to discern the difference between accepting crossdressing and accepting crossdressing as a joke, but there was certainly the possibility of an overwhelmingly negative reaction. When I crossdressed the past two years, my costumes were met with a mix of eye-rolling and genuine help in terms of creating the costume. Not a negative word was spoken, and this certainly made it more okay for me to come out when I eventually did this past summer.

Now crossdressing on Halloween means something entirely different to me. It’s a year later, and at the time that this is being written, not including myself, six other people know I am a crossdresser. This Halloween I plan to increase that number significantly. As I’m going to be myself (Justine) for Halloween this year, combined with the fact that it’s my third year spending Halloween in a dress, it’s about time that people stopped getting the hint, and had the information handed to them on a silver platter.

Anyone who attends my annual Halloween party this year will leave knowing that I crossdress. I’m not exactly sure how I’m going to about it yet, but I have a few ideas that I will go into more depth about in Part 4 of the series later this month.    I’m not sure if Halloween, while dressed, is the perfect time to come out, but I at least it’s a semi-controllable situation that I know has an end point.

You (a closeted crossdresser)

This part is easy. Do what I did! Have fun with Halloween. Use it as an opportunity to test some waters, and enjoy yourself. If you’re going to remain in the closet, you might as well crossdress on the one day that you’re actually “allowed” to. What’s the worst that could happen?

You (an outed or semi-outed crossdresser)

Push the borders of crossdressing of your crossdressing. Do something you normally wouldn’t. This year I’ve got myself a low-cut dress, which is quite revealing. I’m looking into getting my eyebrows threaded, something I normally wouldn’t do, and I’m also going to get to have nails for the first time. I’m also going to begin to do some research as to whether or not there are any small stores around my neighborhood that will help out with makeup, under the guise that I’m “jokingly” doing it for Halloween. I’ll have more information on all that later, though.

I think Halloween works great for out crossdressers, simply because it’s Halloween – you’re supposed to do something crazy and fun. In Part 1 I discussed  the question of whether not simply crossdressing in your regular clothes constitutes a costume or not. After even more consideration, I think that it really depends on where you are in your stages of crossdressing. For me, it’s still new and not a lot of people know – so in a way, Justine is just a costume to most. Next year, however, I’m definitely going to go the traditional costume crossdressed route so that it’s not male me dressing up as Justine for Halloween, but Justine dressing up in costume. If that makes any sense.


Okay – this post wasn’t as organized as I originally hoped. I don’t know if I was short of things to say, or my brain just wasn’t in the right place for writing at the moment. Regardless, I hope everyone who reads this can take something from it, and have a terrific Halloween that is meaningful for them. I’m exactly two weeks away from the date of my Halloween party and will probably post the next two installments on the next two Saturdays. Part 5 will be an after-Halloween post with pictures and a summary of the party.

I’m dressed right now in a short woolen dress with panty hose and I’m happy with how I look. This makes me kind of anxious to go for a walk outside. It’s still light, though, so we’ll see in a few hours.