My First Time

For decades now I have been crossdressing in private. In the last couple of years my desire to take a little bit of this feminine flair out into the world has been increasing. I was going through my clothes the other night and I noticed how much I liked wearing women’s jeans. Moreover, I realized that certain designs were not that far off from the men’s pants I was already wearing. Suddenly, wearing the perfect pair of women’s jeans seemed like a nice blend of masculine and feminine.

There was a slight catch. Because I acquired most of my women’s clothes surreptitiously from strangers (craigslist, ebay, etc), I didn’t get to try any of it on ahead of time. So while I have a huge collection of clothes (more womens than mens, truth be told), not all the pants fit as well as I would like. Accordingly, I knew that to be comfortable for everyday use I couldn’t shop blindly and hope for a good fit. I would have to go the conventional shopping route.

I had a pair of men’s jeans from American Eagle that fit me well. Based on that and the selection I saw online, I decided to give them a shot. Once there, I quickly settled on a pair of their Artist bootcut low rise jeans in an x-long, cuz “I gots legs for dayz yo!” I was curious to try the Boyfriend jeans in a more straight leg, but that style may be discontinued as I could not find it in the store.

I went for the dark color version of the jeans to help hide the masculine shape of my legs just a little bit more. The jeans were a good fit. The stretchy Artist jean fit snugly through my hips and upper legs and then relaxed around my knee and gently flared at the cuff. I was initially concerned that the flare was too much but once I put on my shoes that concern diminished. The bootcut flare on this style pants may still be a bit on the large side for my liking but I decided to go with it. 

Admittedly, one of my chief concerns was how my butt would look in them. I have a rather flat posterior and so my butt really gets lost in most of the sloppy fitting guys’ jeans – happily, it looks better than it ever has. I’m not creating anything I don’t have, I’m not about to pad anything, but it definitely helps me show off a bit. 

As curves are concerned, the front of the pants does showcase more than what folks with penises are probably used to. It’s not extreme, it’s just that we aren’t accustomed to seeing our form showing through (a trend that I would love to see reversed). The pants have enough compression to keep anything from being a spectacle. This aspect of jean fit does mean that the type of underwear I wear matters much more. I’ll touch on this in my next article but suffice it to say that the tighter you can bundle everything together the better the fit looks.

Now that I had found my pair of pants the only thing left to do was put them on and go outside. During my first wearing I was a little self-conscious but not because of anything I noticed from other people. It was just a reticence based on the fear of what could happen. Truthfully, if people were looking at me, I didn’t notice. I honestly didn’t even feel like I was making a scene. I was just being me. 

That last part is important because I have noticed that I am happier that I now wear these types of pants. They say (i.e. studies have shown) that people who have traits which cross the (artificial) gender divide have higher self-esteem than those who rigidly conform to it. My experience reinforces this finding. Living more authentically for me brings me joy, staying hidden does not.

After multiple outings in these new jeans I love them more each time I go out. There are differences based on what I’m used to with guys pants, that is inevitable. I am noticing more and more how they give me a feminine look, more than I had anticipated. However, I have come to love this as well. 

I have always been shamed for my thin body by other men. It used to bother me that I wouldn’t be perceived as masculine. Now, I thank my lucky stars that I didn’t end up with the compacted muscular frame I wanted as a kid. My tall lanky build lends itself well to my desired style of dress. I enjoy seeing clothes hug my body and accentuate the thin form that I have come to love. It’s all very wonderful to experience.

At this moment, I am wondering how to maintain my blend of clothes come summer (jeans are too hot in warm weather). I’m currently exploring women’s shirts to wear with my guy shorts as well as looking for a few styles of womens shorts to pair with some of my more form fitting shirts. This is an exciting new frontier for me and as few people seem to talk about this type of thing I plan on detailing my experiences here as I go along my cute, little, merry, crossdressing way.

Until next time, join me in obliterating those gender boundaries my beauties.

Footnote:

I have resorted to generic terms of men and women, masculine and feminine, for the sake of clarity. However, make no mistake that if these labels don’t fit you, then trust me when I say that I see you, you sexy gender trail blazing thang you (I really don’t talk like this, lol). I am also aware of the argument that there are not women’s clothes or men’s clothes, but just clothes that anyone can wear. I find validity in this viewpoint. However, for me there is a distinct appeal to wearing something that I know is designed for women. I also enjoy referring to it in that way. I feel sexy wearing “women’s” clothes. Doing so allows me a rejection of masculinity that feels more complete than wearing gender neutral clothes would.

This likely stems from the fact that I am exploring the identity of being genderfluid and with that the recognition that I sometimes feel a little more masculine and sometimes a little more feminine and never fully one or the other. For this reason, I’m starting to hedge on calling what I do crossdressing. Until I come up with a better term then this description will awkwardly suffice.

Article soundtrack: Every Time I Die – Post-boredom. Every Time I Die – Ebolarama. PUP – Totally Fine. Bayside – Strangest Faces.

You’re Woke And It’s A Huge Problem

Woke was a term that when I first heard it, I thought it was a novel way to describe oneself. By the second time I came across it, the word had already soured. I realized quickly that it would be a self congratulatory term and as liberals we do too much of that as it is. 

Perhaps the biggest challenge to any group but most certainly the liberal/left is to check your ego at the door. We like to think that our views (or perhaps our belonging to a disenfranchised group) put us above others, that we are somehow better than whatever out group we have established. The truth is, most of us are still jerks that live a very unexamined life. If that sentence pisses you off then you need to keep reading more than anyone else. 

We hide behind labels. If we are woke, feminist, liberal, and egalitarian then we can’t be sexist, racist or transphobic. We make those who are outwardly racist/sexist/queer phobic evil and so we must be by opposition, automatically good. 

If being critical of racism, sexism and heteronormativity makes you feel good about yourself then I assure you that you are doing it wrong. Why do you feel good about affording people a basic level of decency? It is because you have positioned yourself against your so-called villains that you seem so accomplished and enlightened. 

Casting ourselves as heroes shuts down our critical thought. This is why women and people of color (though by no means exempt from my criticism) lament the emotional labor they have to expend on their supposed allies and sometimes ask for spaces which exclude us. 

We are still sexist. We expect certain physical or personality traits from out partners (you must be this tall/short and masculine/feminine to ride). The idea of what male and female is has been deeply embedded in the ways we think and act. We think we choose our partners freely but that is no closer to being true than it was 50 years ago. Sure we can marry a wider breadth of people than we could then, but our stereotypes still remain as to how people must look and who they can be in relation to us.  

We have more diverse friends now but how many of those friends serve to make you feel good. I have a friend who talks about being the token black guy among his liberal friends and as much as I’d like to assure him that this isn’t true I know there is an element of truth to it. Likewise, as a queer man, who cross dresses occasionally, I watch liberal women’s faces light up when they tell me they would gladly go out on the town with me in drag. What a story that would be for them and it’s a great way to get your “woke card” stamped. 

Our privilege (ie: ignorance) surfaces when we ask someone to speak for all people of their identification or sexual persuasion. It happens when we occupy the spaces of feminists or people of color and feel resentful that our opinions aren’t weighted to the degree we are used to. It happens when we use others to atone for our “social justice sins” by hogging the spotlight for ourselves and our woes. We want to be good but not at the expense of others noticing how good we are. We languish in our selfish habits. 

Essentially, we rely on others to do the work that we should damn well be doing ourselves. No one is asking you to break down and ask forgiveness from the group (i.e. representation of the other). They are asking you to listen, then take responsibility and put your words where your mouth is. You have to do your own work. The information is out there if you look for it. I hate this term but I’m going to use it, “google it!” Alternatively, ask people what might benefit you to read or watch and then actually do it. 

For instance, I’ve been reading work by trans folks/people in an attempt to understand them as much as I can. It’s shocking how much I thought I was being an ally and yet I was still making so many assumptions that could hurt them and their cause. It’s hard to learn we are wrong but it’s absolutely necessary. Moreover, learning there may not be a correct way to view certain things, like gender, can be exciting and humbling all at once. It’s not always fun work but it’s work that needs done. 

While you’re taking in new information be so honest with yourself that you’d rather not. Then be honest even more because I guarantee you that no matter how much work you do there is still more to be done. Your job of self growth ends when you do. And for god (that I don’t believe in) sake, drop the fucking self-congratulatory labels.

Biphobia & Orlando: Am I gay enough to grieve

So this woman wrote a wonderful article exploring the competing feelings that she experienced as a bisexual after the Pulse night club massacre. It’s about a two minute read and well worth your time.

https://medium.com/@elledowd/biphobia-and-the-pulse-massacre-add1dd9b27be#.a2fz3vk6n

By contrast: for me this was the first time I felt gay enough. The knot I had in my stomach for the two days after told me that every fiber of my being belonged to the queer community.

A Word On Marriage and Divorce

Marriage

I’ll just let this story speak for itself because no matter how much I wear a dress I can never fully appreciate what women have been taught about what a marriage proposal is supposed to mean. I did find the idea that a marriage is not an accomplishment thought provoking though.

http://www.huffingtonpost.com/natalie-brooke/getting-married-is-not-an-accomplishment_b_9189828.html

 

Divorce

You should read this even if you’re happily involved with someone else. I wish I had this information earlier. This article basically talks about how divorce can be a positive thing and I totally agree. I love the idea of fighting for a marriage or a relationship, but not every battle ends as you would like.

For me my first marriage is most applicable to this article. I was chastised once by my first wife for considering divorce as one of all the possible outcomes for a relationship. She said I was preparing for divorce if I thought that. I developed a fear of bringing up ways that our relationship wasn’t functioning because of this.

To make a long story slightly less long, it’s pretty easy to see how a real or perceived inability to address relationship problems results in a non-functioning partnership, and so it was.

I went for maybe 4 or 5 years hoping that things would get better. They didn’t. One day I had an epiphany which let me see how bad things had become and I also realized that I couldn’t go on like this anymore. I was exhausted and done. Truly done. I had been trying so much by myself that I didn’t want to lift a finger for that relationship anymore. Perhaps that is horrible to say, but it was true. Once I was to that point of realization divorce was the only reasonable choice.

When I awoke the next morning after making my decision I felt so light and unencumbered. I knew divorce would turn my entire world upside down, and so it did, but it was also liberating (for both of us I imagine).

It’s for this reason that I can completely relate to what’s being said in the statements compiled in this article.

http://www.huffingtonpost.com/entry/whatever-you-do-dont-say-divorce-is-not-an-option_us_56b90119e4b01d80b24768f6?

Do You Love An Idea Or A Person?

http://elitedaily.com/dating/someone-loves-idea-you/1321834/

I can add another sign to tell if someone was in love with the idea of you or the actual you. If they use one of the reasons for their initial attraction as a reason to break up then it’s likely you were idealized to some extent.

I’m pretty sure this happened to me. I had a beautiful relationship, or I think it was, with a pretty dynamic individual for almost three years. Shortly before we started dating she told me that she had always wanted to date a bisexual man. I knew I was being fetishized to some extent and that her urge was built upon what she believed a bisexual guy would be like, but it is important to me that my partner accept my sexuality and on that front this seemed like solid ground.

Fast forward to the end and it was the primary reason given for our breakup. She accepted me being pansexual intellectually, but had a negative visceral reaction to me liking men. Identity issues are a big deal for me so for the person I cared the most about to reject me on a very fundamental level was deeply hurtful to say the least.

I struggled with this for awhile, until I read the article below and it started me thinking that maybe this is what had happened to us. The idea of dating a bisexual guy was a romanticized one. The actual experience was apparently drastically different for her and it was too much to handle.

I want to leave you with a slightly different approach to handling the reality of who a person is. For me learning the ways someone violates my expectations is one of the exciting things about getting to know them. In the television series Firefly there is a line that has always resonated with me, “It’s my estimation that every man ever got a statue made of him was one kind of sommbitch or another.” It’s about nuance and the juxtaposition of the ideal verses reality. It’s what I love about people and eventually it will be one of those things that someone loves about me.

So what about you? Has this ever happened to you and which side of the relationship were you on?

Biphobia and its Effect on Mental Health

I think this article makes some good points. One of the things that most resonated with me was when the author says, “I could not be myself until I could be all of myself at the same time.” This has been so very true in my experience. I didn’t start coming into my own until I started being out about one of my last secrets; that I was pansexual.

I’m a little lucky in that to some extent I’m kind of like her rebellious sister in that I didn’t really give a fuck what other people thought of me. Still, I can feel the pressures that she discusses in this article and I think this is an important discourse to have.

http://everydayfeminism.com/2016/01/bisexuals-mental-health/

People Don’t Know Jack About Being Bisexual

I think my title justly sums it up so read this little jewel for some examples of the lies people tell bisexuals.

Okay, I’ll give you one example. Long before I came out or had even dated a guy I stumbled onto a blog with gays and lesbians bashing bisexuals. They had been dating a same-sex person of bisexual orientation and their relationships had ended. Their bisexual partners had gone on to date another person of the opposite sex and they were being lambasted by the gay community on this site for doing so.

Um, we’re bisexual! That means that we can date a man, and if that relationship doesn’t work out then we can date a woman next if we so choose. It’s not even in the fine print, it’s yelling at you from our identity title.

http://everydayfeminism.com/2015/09/lies-tell-you-when-bisexual/