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..