The Evolution

Gentleman's Quarterly, April 2022

Boys' Day Out

A 21st Century Moment:

Middle-aged housewives getting their hair done in a beauty salon (from a BBC television documentary about the "new masculinity" in the Post-Patriarchal Era).

Suits Me Fine

Call me "Jamie."

It is not my real name; it’s the name I go by when I dress up like a boy.

I dress like a boy because I am a crossdresser. I prefer male clothing to female clothing. In addition, I try to act like a boy. I want to be masculine, not feminine.

I want to be able to go out in society and pass as a male, but my female characteristics are difficult to disguise, so passing is a tough goal to achieve. I will keep on trying to improve my presentation because I know it can be done.

Many crossdressers have websites where they display photos of themselves crossdressed and many of the photos are very convincing. These females look just like boys, so I know passing is possible. I may not be able to fool all of the people all of the time, but it would be nice if I could fool some of the people some of the time.

Also, there are websites that provide information on how to pass as a male. They describe how to walk, talk, and act like a boy; how to style your hair to look like a boy; what undergarments to wear to achieve a male form; etc., etc. There are also online stores that cater to crossdressers where you can buy everything you need to "express your masculine side."

My crossdressing started around the age of puberty. I don't know where the idea came from; it just popped in my head while I was in the bathroom getting ready to take a shower and there was one of Dad's suits hanging on the shower curtain rod.

That pinstriped suit called my name and I could not resist trying it on. It fit me like a glove. I felt so masculine wearing it and I could not take my eyes off myself preening in the full-length mirror mounted on the bathroom door.

Suddenly, I felt very guilty and was worried that I might be caught, so I slipped out of the suit as quickly as possible, hung it back on its hangar, and took a cold shower.

Since then, I dress in my Dad's and brother's clothes whenever I am home alone.

I prefer my brother's clothes because he is only two years older than I, so he dresses like a boy my age dresses, whereas my Dad's clothes are more adult, i.e., clothing that an adult male wears.

But Dad's wardrobe includes items that my brother's wardrobe does not, so when I dress, I borrow items from both my Dad and my brother. For example, my brother has no suits, whereas Dad has six suits and I guess after that first crossdressing experience in the bathroom, I have a thing for suits.

My favorite suit is one Dad wears when he and Mom go out to a fancy restaurant or to a dinner party. I like it because it has a more youthful look than his other suits, which are more conservative, i.e., the kinds of suits you wear to the office or to church.

Dad claims that that suit is a "shun-el knock-off," whatever that means? The fabric of the suit is a rosy pink boucle with blue undertones. It has a cropped jacket with four buttons and four pockets and a pencil skirt that’s 20 inches long.

Dad also has a matching pair of pink pumps with a 4-inch stiletto heel; he looks so masculine in that outfit! And, wow, my Dad has great legs; he sure shows them off in that suit with its skirt about four inches above his knees, wearing nude pantyhose perched on those 4-inch pumps.

Dad is a beautiful male. He is a platinum blonde and always looks great no matter what hairdo he wears. His makeup skills are excellent, too, with huge eyes and full pouty lips.

I try to emulate Dad when I crossdress. And sometimes when I do my makeup just so, I look a lot like him.

The Happy Homemaker, 2045

As the mid 21st century mark approached, the Post-Patriarchal male was completely domesticated, respectfully subservient, and accepted his status as the "weaker sex."

Young adult males in 2045 represented the second generation of the modern males and were fully acclimated to that role because they grew up under the matriarchy and knew no other way.

As a result, modern male fashion was not the anathema to the second generation as it was to previous generations. They not only accepted, but they adored the "new masculine" attire, hairstyles, makeup, etc. and they happily acquiesced to their role serving the females.

(The accompanying photos were part of a fashion spread that appeared in the April 2045 issue of Good Housekeeping. It featured film actor Sonnia Suchere modeling wifely attire of the day. Miss Suchere had recently won an Oscar for his portrayal of Sugar Kane Kowalczyk in the remake of Some Like It Hot.) 

Working Boy Fashions, Circa 2028

A July 2028 Glamour magazine fashion spread, "Working Boy Chic," represented the styles worn by working boys (secretaries, receptionists, schoolteachers, etc.) in the late 2020's. Although many males clung to female-influenced short hairdos, some trendy boys began wearing longer masculine coiffures.

Masculine Do

A Breck Boy

By the end of the 2030s, boys were sporting very masculine hairdos in a vast array of lengths, styles, and colors. Meanwhile, most women preferred short cropped haircuts.