On Explicit Femininity

As I have recounted in previous posts, my first real foray into crossdressing was in my sister’s closet as a child. The closet of a high school girl was filled with boundless options for a young boy trying to escape into the world of the feminine: mini-skirts and sundresses, bracelets and necklaces, skinny jeans and short shorts. My goal in crossdressing was to, for a fleeting moment, put myself in the role of one of the girls in my class.

Despite the multitude of options at my disposal, I always found myself trying on the skirts and dresses. In fact, I never once chose my sister’s short shorts or skinny jeans despite the fact that all the girls around me were wearing them. Looking back years later, this puzzled me at first: you would think that in my moments of being a high school girl, I would want to wear precisely what all the other girls around me were wearing. Why did I never choose to wear the skinny jeans or the jean shorts?

In the ensuing years, I have realized that in my fantasies of being a woman I am drawn to those things that are uniquely and distinctly feminine. Both women and men wear jeans; while the styles differ significantly, jeans were still within our society's bounds of "men’s clothing" and weren’t far enough away from what I normally wore to allow me to fulfill the fantasy sufficiently. However, in our culture dresses and skirts are worn exclusively by women. As a man, I wear jeans all the time; but when I was wearing a dress, there was no question that I was wearing something that was societally forbidden to me as a man.

I have found that the things I enjoyed wearing the most, and subsequently enjoy photoshopping myself wearing the most, were the clothes and accessories that were most exclusively feminine. In 2018, some men wear diamond studs in their ears, but chandelier earrings and hoops are the realm of women. Men wear chain necklaces and some may even wear charms, but only women in our society wear pearls. By this same principle, when I am photoshopping myself as a woman, I prefer heels to flats. I always choose that which is most distinctively and explicitly feminine.

Now that my preferred method of living out my dreams of being a woman is through photoshop, this has at least somewhat softened. Now that I can actually physically see myself as a beautiful blonde with a blowout and an impeccable manicure, the fact that I’m wearing skintight white jeans rather than a sundress or diamond studs rather than hoops, has stopped bothering me as much. 

Still, I think the key is that in any of the pictures, the picture is explicitly and unquestionably feminine. I spend 100% of my actual life as a man; in my dream world, there’s no need for half measures.

My Modern Alternative to Crossdressing

I still remember the first time in middle school I tried on one of my sister’s dresses. I snuck into her room while my parents were out at work and my siblings were away with friends. I remember the rush I felt with the soft touch of a lacy thong, the cool sheer of black tights encasing my legs, and the free-flowing feel of walking in a skirt. My heart leaped into my chest when I saw myself in the mirror.

For the next several years, being alone in the house meant a brief glimpse into what it might be like to be a girl. I grew to know intimately the feel of miniskirts and sundresses, tights and fishnets, the taste of lipstick and the smell of nail polish. Throughout middle school and high school, time alone at home was a release for my pent-up desire to experience the feminine.

Then, I went to college.

In college, I lived in a dorm and had no access to women’s clothing. More than anything I feared (and still fear) discovery, so buying women’s clothes was out of the question, especially since I had a roommate. I still continued to fantasize about being a woman, but suddenly I had no outlet.

For a long time, I tried to fight the urge, but since opportunities were so few and far between when they came up I had trouble resisting. Once, I went to a friend's house in college and I stayed in his sister's room who was away. Despite the fear of getting caught, I couldn't resist, late at night when everyone else was asleep, trying on my friend's sister's clothes. The feel of her pearls around my neck and her cocktail dress on my body was incredible. I knew the consequences would be disastrous if someone heard, but the thought of being a woman clad in stockings and a dress overrode all my self control. Still, I knew I needed a new outlet. 

It was in college, without any access to women’s clothing, that I discovered an outlet that even a few years ago would never have been possible.

I discovered some new tools: a laptop all my own, Facebook, the entire Internet's worth of pictures, and most importantly, Photoshop. 

Instead of seeking out women’s clothes, I would find pictures of friends and acquaintances on Facebook dressed for weddings or cocktail parties, and with increasing skill photoshop in my own face. I found pictures online of galas and balls, creating photos of myself as a debutante, dressed to the nines, with an engagement ring on my finger and a man on my arm. I searched for pictures on fashion sites and department stores so I could create images of myself wearing the cutest dresses, and photoshop myself into the mix of a group of women.

While Photoshop did not provide me with the physical sensation of wearing women’s clothing, it gave me much that physical crossdressing could never achieve. First, it allowed me to see myself in a woman’s body. When I would try on my sister’s clothes as a child, it was always readily apparent that I was a man trying on women’s clothes and not truly actually becoming a woman. Try as I might to stuff a bra with tissue, it always looked off. I could not get rid of my broad shoulders or my five o’clock shadow. Indeed, as I grew older I couldn’t fit into much of the clothing at all. Shoes, in particular, were always an issue and I could never try on heels.

Photoshop allowed me to actually visualize myself as a woman. I could physically see myself with long blonde hair, wearing hoop earrings, 5-inch stilettos, or a bikini top, and it looks realistic. It also completely opened up access to whatever clothing I could possibly want: while physically crossdressing, I could only try on what was in front of me, and even then only if it fit. With Photoshop, I was literally only limited by the photos I could find. I could never have dreamed of trying on a Gucci dress or wearing a Chanel bag in real life; with Photoshop, I could wear even more than a woman with an unlimited budget at Saks: I just had to find the right photo.

What’s more, Photoshop allowed me to visualize some of the social parts of being a woman. As I have mentioned, part of the fantasy of being a woman is engaging in feminine activities. For example: I could never actually be a bridesmaid in real life, nor try on a bridesmaid dress without great difficulty. With Photoshop, I can actually see myself in a gown, with my hair done up and decked out in diamonds, in line smiling with the other bridesmaids, or see myself at my sorority formal, with all my sorority sisters smiling with their arms around me.

I have also mentioned that I have sexual fantasies involving me having sex as a woman. Yes, Photoshop can be an outlet for that as well. While I could physically never have sex with a man as a woman, with the whole Internet’s worth of pictures at my disposal I could see what I might look like if I could. I have photoshopped myself on my knees pulling my hair back in preparation for oral sex, or in the act of being penetrated, or being eaten out. These are all things that I could never actually experience (since I have absolutely zero interest in having sex with men as a man). Indeed, a key component of the photo is my distinct femininity. It has to be crystal clear from the picture that the person in the picture is woman-me and not male-me, otherwise I find the very idea of the picture viscerally repulsive (long hair is a must, and manicured hands or jewelry are helpful too… analyzing this point will likely be the subject of a future post). Photoshop allows me to have a visual representation of the actual transformation into a woman and to engage in those feminine acts, even if only visually.

At this point, I am married to an incredibly fashionable woman with a huge closet, yet never have attempted to wear her clothes. Photoshop has essentially completely replaced physical crossdressing as my outlet for seeing myself living the feminine. What’s more, photoshopped pictures are just files: they don’t require sneaking around or hiding clothes to keep them a secret. Photoshop, with all its advantages, has become my 21st century outlet to the world of femininity..

An Introduction

I am a heterosexual cis-man, happily married to the woman of my dreams.

A small voice at the back of my mind dreams of being a woman. I love my life as a cis-man and have zero interest in transition. This is my story.

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I am incredibly privileged to lead a very happy life with few complaints. I am happily married to the woman of my dreams, work in a field I love, have a nurturing family, and am financially stable. By all rights, there is nothing wrong with my life.

I also have a secret that I have been concealing since I was young. Nobody in my life knows or suspects. For all intents and purposes, to the world it doesn't exist.

There is a small but undeniable part of my mind that dreams of experiencing the world as a woman.

This part of me has existed as long as I can remember. One of my earliest memories is of sneaking into my mother’s room to try on her jewelry; I was so young that I didn't yet realize that you need holes in your ears for earrings to fit. Throughout childhood the trappings and role of the feminine intrigued me.

However, I never felt like a girl trapped in a boy’s body. I loved my life as a boy, and enjoyed many stereotypically male activities: I played and watched lots of sports and devoured sci-fi and fantasy novels. I was never jealous of my female friends’ dolls or clothes. I never hated my penis or my body; I never at any point felt like I was born the wrong gender.

However, I always harbored a latent desire to, just for a few hours at a time, put on makeup and a dress and gossip or shop with the girls in my class. I never felt excluded per se, but wished that I could seamlessly transition between the boys playing tackle football in the mud and the girls trying on new skirts at Abercrombie. 

What is interesting is that filling the societal female role was most intriguing to me. In my fantasies, I was never a girl just in the privacy of my home; I was a girl out with a group of other girls, fitting seamlessly into the group.

These fantasies evolved throughout adolescence as I grew and matured. Like my other heterosexual male friends, I fantasized often about hooking up with girls in my school, or actresses on TV. However, in addition to these fantasies, I fantasized too about hooking up AS a woman.

I have never felt any attraction to men. I am a heterosexual man, and when I imagine myself engaging sexual activity with other people, I exclusively imagine having sex with women. 

However, in these fantasies where I am a woman, I am not myself; I am a different person, and that person is a heterosexual woman. The men in these fantasies are nameless and faceless; they were merely vehicles to expression of my female sexuality. 

There is a large body of literature defining a man's desire to live a female experience: the very controversial idea of “autogynephilia” coined by Blanchard, or the notion of “crossdreaming.” While I prefer the term “crossdreaming,” I find some of Blanchard’s categorizations useful for the purposes of understanding my own fantasies and desires.

Blanchard breaks down the desire for a man to engage in the feminine into four categories:

• Transvestic: the desire to wear women’s apparel. Personally, I often fantasize about wearing dresses and skirts, walking in heels, and wearing jewelry and makeup
• Anatomic: the desire to have breasts and a vagina
• Physiologic: the desire to have feminine body functions, such as menstruation or lactation. Personally, this does not apply to me in any significant way
• Behavioral: the desire to participate in stereotypically feminine behavior. I personally find it useful to break this category down into two parts:
• Sexual: the desire to engage in sexual activity as a woman
• Asexual: the desire to engage in stereotypically feminine behavior as a woman outside the bedroom. Personally, this manifests as fantasizing about being a bridesmaid, going shopping or getting manicures with girlfriends, or being in a sorority

I don’t yet know how to precisely define myself. I hope to use this space to further explore these feelings and fantasies and add to the conversation. Please feel free to comment on any of my posts, with either questions or comments: this will help me provide more material to explore these feelings and further define what it means to have these fantasies.