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.

Horny Hometown

They say you can never go back. Sometimes though that isn’t true. 

I’m from a small town in the middle of nowhere Illinois. When I was a child I had a crush on a fellow classmate. He didn’t know it at the time. What I didn’t know is that he also had a crush on me.

Once we were out of school, I would occasionally bump into him at the store. I would say hello, hoping he would say anything back. It never really happened. Crushes can be weird that way. 

Twenty five years later we discovered our mutual interest and discussed possibly meeting up to fulfill some part of our desire. 

The thing I didn’t mention about this small town is that it is somewhat incestous. Through social media I watch people bounce from person to person, classmate to classmate; married to one and then another. It’s like a game of romantic musical chairs and when the music stops for the final time you die with the one you’re next to. 

I often wonder if anyone imagines potential romantic partners existing outside of that two mile square radius. 

My crush messaged me to say that another classmate was in a bar and had just made a couple of moves on him. He seemed very excited about it all. Nothing against either of them but I suddenly became aware of the dynamic I was considering entering into.

I don’t think I am above anyone that lives there, it will always be a home, but I don’t want to become another townie fuck toy. Someone who is just a tidbit of conversational fodder consisting of “hey did you hear who so and so had sex with!” A coupling with my crush would initiate me into the familial order of the small town orgy. It’s not that the talk alone bothers me, I’m sure I’ve been a part of the gossip round table before. It’s that I don’t want to become part of the culture and what it represents. I do not want to shrink back down to fit in there. 

I realized that during my return trips, I visit the same place I was at during high school, the same place I was at when I married at 20, the same place I was at when I divorced years later, and the same place I left 900 miles behind me 8 years ago. 

Nothing there has changed, except for me.

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.

An Alternative View of Labels

Like one of the authors of the articles below I have always wondered if labels concerning human sexuality do us more harm than good. I think there are arguments for both sides and I find the interplay of ideas particularly interesting.

Here are two stories of people who though they were stalwart adherents to a particular way of being until someone special helped them discover an unexpected truth about love.

I Came Out as A Lesbian – Then Fell In Love With A Man

How My Sexuality Changed When My Husband Became My Wife

As you can see by the titles, the first story follows a traditional view of relationships while the latter has a more non-traditional story arch. I hope you enjoy them and whoever you love now or come to love in your life, I wish you the greatest happiness.

How Did Your Sexual Orientation Form?

I think for many people the premise that sexual orientation is not fixed, but can vary with stimuli, will be a difficult one to accept. However, thanks to trans folks (again) we have a wonderful new outlook on the world. Here are a couple of women who might just change the way you think.

https://broadly.vice.com/en_us/article/the-trans-women-who-become-lesbians-after-years-as-gay-men?utm_source=broadlyfbus&ncid=fcbklnkushpmg00000050

Why She Is A Slut And You Shouldn’t Care

A very short but useful article straight from the source. If you want to help her cause, stop slut-shaming when you hear it. I’m fairly easy going but I’m quick to interject my alternative view that there is nothing wrong with being more open with your body and sexuality than others may be comfortable with.

http://www.femalista.com/im-a-slut-and-100-proud-of-it-so-stop-shaming-me-already/

Famous Model Comes Out As Intersex

To be truthful I’ve never heard of Hanne Gaby Odiele, but then I live under a rock where the light of day as it concerns models cannot penetrate. I was very pleased to read this though and I know this will be the start of something great in societies throughout the world.

https://www.theguardian.com/world/2017/jan/24/model-hanne-gaby-odiele-reveals-she-is-intersex

This is proof that no matter how many ceilings we shatter there are others in the houses down the street that need demolishing as well. Being accepted as gay wasn’t the last social battle to be won, being accepted as transgendered isn’t the last frontier, and being accepted as intersex won’t be the final struggle either. We will never stop evolving as a people and as a society, nor should we.

Guys, You’re Doing Friendship Wrong

Sociologists have long known that the way we do friendship now is not the way it has always been. However, you’re not a sociologist (well not an employed one anyway) so check this out to start understanding that there is something contrary to human nature about how we do friendship then work to change that; both for your health all those other guys who just want someone to hang out with.

http://www.vice.com/en_us/read/why-men-lose-friends-in-their-20s?utm_source=vicefbusads

As I read through some of these stories it becomes obvious to me why I have tried to establish friendships with women recently.

Wait Till You See These Old Photos of Men

These photos are awesome and they will turn the very notion of what men used to be compared to what they are now on its head.

http://www.artofmanliness.com/2012/07/29/bosom-buddies-a-photo-history-of-male-affection/

Do You Dream Of Another Guy With Your Wife?

If you do apparently you’re not alone. This is one of the most prevalent fantasies that guys have and the motives behind this imagined scenario are actually quite diverse. This phenomena was a complete mystery to me so if you’re like me or if you have this fantasy and are curious to learn more about it then read on and enjoy.

https://www.psychologytoday.com/blog/evolution-the-self/201602/what-secret-male-sexual-fantasy-is-surprisingly-common

I’m making this guy week because as I look back through my saved articles many of them relate to men so I figured I would clear out the information banks and share them.