Training the New Administrative Assistant

My Son, the Fashionisto

My son Cameron found me in the kitchen washing the breakfast dishes and began complaining, "Daddy ― look how Mommy had me dress today!"

I looked up from the sink full of dishes to see how my spouse had outfitted our son.

A sleeveless white skater dress with elasticized waist adorned his body and white skimmers adorned his feet. White pantyhose encased his legs and his short haircut was brushed forward to give him bangs that were held in place with a white barrette. A white purse, slung over his shoulder completed the outfit.

His eyes were lightly made up ― just a touch of liner and mascara and a smudge of eyeshadow. Pink lip gloss highlighted his lips and he might have had a light touch of blush, too, but I was not sure. Either way, his makeup, as well as his whole presentation was befitting a teenager his age.

"What's the matter, Cammi? You look very pretty," I replied.

"Thank you, Daddy, but I can't go to school dressed like this," he whined.

"Why not?" I asked.

"The other boys will make fun of me," he replied.

"I don't understand why they would," was my perplexed retort.

"White ― after Labor Day!" was his anxious reply.

Husbands, Wives and Breasts

In this day and age, it seems absurd that husbands still want wives with big breasts, but they do.

With that in mind, my parents started me on a regimen of hormone supplements as I approached puberty. The purpose of the hormones was to help me achieve a state of pulchritude that would make me more attractive to the opposite sex and eventually snag me a husband.

When I began taking the supplements, I had big expectations. My budding breasts seemed to outgrow my training bra overnight and I was soon sporting a new A-cup bra. However, as all my friends moved up the bra cup alphabet, my breasts refused to grow any larger. I was stuck at an A-cup even after the doctor increased the dosage of my hormones.

As I neared my sweet sixteen birthday with nary a date in sight, Mom offered me breast implants as a birthday gift. But I was adamant that no surgeon was going to take a scalpel to my surgically virgin body, so I refused.

Although I lacked bountiful breasts, I had other attractive features including a pair of long shapely to-die-for legs. To show them off, I always wore the shortest skirts and highest heels. On a few occasions, I was sent home from school because my skirts were so short that they revealed other assets.

Nevertheless, I built my wardrobe around mini-skirts and mini-dresses hoping to attract someone who preferred well-turned ankles over well-rounded breasts.

After graduating from high school, I became a receptionist at a high-tech engineering firm where I attracted a design engineer who was an unabashed leg aficionado. We dated for six months, then she asked for my hand in marriage.

We just celebrated our fifth wedding anniversary and she still likes me to show off my legs. (She tells everyone, "He has the best legs in town.")

As her obedient and dutiful wife, I willingly comply and wear short skirts or dresses and high heels throughout my day.

On the newsstand, February 2034

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.