Crazy About Crossdressing

 

Are You a Sissy?

What Is a Sissy?

“Sissy” is one of those words whose meaning depends a great deal on who is saying it—and how.

Spoken by a playground bully, it is an insult. Adopted by an adult describing himself, it can be an expression of identity. Used between consenting adults in a private relationship, it can have an erotic meaning.

Same word. Very different intentions.

For many of us growing up, “sissy” was a warning about the boundaries of boyhood. Cry too easily, dislike sports, enjoy pretty things, or hold your hands the “wrong” way, and someone might apply the label. The message was simple: boys were supposed to avoid anything associated with girls.

And being compared to a girl was supposed to be embarrassing.

That raises a question: what, exactly, was so terrible about being feminine?

From an Insult to a Chosen Label

Some adults have reclaimed “sissy,” using it affectionately or proudly to describe their femininity. They may enjoy dresses, lace, makeup, elaborate hairstyles, or an especially frilly presentation. The word can give them a way to embrace qualities they were once told to hide.

Others want nothing to do with it. They remember the humiliation attached to the word and have no interest in welcoming it back into their lives.

Both reactions deserve respect. Reclaiming a label for yourself does not give you permission to apply it to someone else.

Is a Sissy a Crossdresser?

A person might identify as both, but the words are not interchangeable.

Crossdressing describes wearing clothing associated with another gender. It does not automatically tell us anything about someone’s personality, sexual orientation, gender identity, or preferred role in a relationship.

Likewise, a man can be feminine without wearing a dress. And a man wearing a dress may be assertive, practical, outspoken, and entirely uninterested in being called a sissy.

A pencil skirt does not come with a compulsory personality.

The Adult Meaning

In some adult communities, “sissy” has a sexual meaning associated with feminization, submission, or consensual role-playing. That is one use of the word, but it should not be projected onto everyone who enjoys feminine clothing.

For many crossdressers, dressing is about comfort, self-expression, beauty, or the pleasure of going about ordinary life en femme. Buying lipstick is not an invitation for strangers to make assumptions about what happens in the bedroom.

Nor does femininity itself imply submission. Anyone who has known a determined woman should already understand that.

Who Gets to Decide?

Ultimately, the most useful question is not, “Does that person qualify as a sissy?”

It is, “How does that person wish to be described?”

If someone embraces the word, respect that choice. If someone dislikes it, respect that, too. When you do not know, a person’s name usually works beautifully.

We spend enough time having other people tell us what our clothes supposedly mean. We deserve room to explain ourselves.

And if enjoying a pretty dress once made a boy a “sissy,” perhaps the problem was never the boy—or the dress.

Wearing Boston Proper

Rich Little (right) femulating on television's The ABC Comedy Hour in 1972.

Still Getting a Leg Up

There is a little irony in the hosiery drawer: many women were delighted to stop wearing pantyhose, while plenty of crossdressers are delighted to put them on.

What explains the difference? How can the same garment be an unwelcome nuisance to one person and the finishing touch to another?

Perhaps it depends on what putting it on means.

For generations, hosiery was part of the price of being properly dressed as a woman. A skirt or dress called for stockings or pantyhose. Bare legs could look unfinished—or so the rules went.

Then the rules loosened. Trousers became everyday wear, offices became more casual, and bare legs became acceptable. Women could finally decide whether hosiery was worth the trouble.

And there is trouble. Pantyhose can be hot. Waistbands can pinch. The crotch can head south while the waistband stays put. A perfectly good pair can become a perfectly useless pair after one encounter with a fingernail.

If you wore them every working day, the opportunity to leave them in the drawer probably felt like progress.

But consider the crossdresser who spent years wishing she could wear them.

For her, hosiery may carry none of those associations with office requirements or compulsory grooming. Instead, it may represent something long admired and, perhaps, long forbidden. Putting on a pair can be one more step toward seeing the woman she wants to present in the mirror.

The obligation and the opportunity are very different experiences.

There is also the matter of when our ideas about femininity took shape. Many of us grew up admiring women whose outfits included dresses, heels, and sheer hosiery. Those images made an impression. Fashion may have moved on, but our affection for that look did not necessarily move with it.

A skirt, pumps, and nylon-clad legs can still say “beautifully dressed” to someone who first learned that visual language decades ago.

Hosiery also does a useful job. It can soften uneven skin tone and give legs a smoother appearance. With the right shade and sheerness, it can pull an outfit together without drawing much attention to itself.

And some people simply like the feel of it. There need not be a complicated explanation for every preference. Some women love hosiery, some crossdressers dislike it, and some of us are quite willing to risk a run for the pleasure of wearing a favorite pair.

We should also be careful about the comparison we are making. A crossdresser’s photograph may show an outfit selected for a much-anticipated evening out. The woman beside us in the supermarket may be squeezing in errands after a long day. One has dressed for an occasion; the other has dressed to get things done.

Of course their choices may differ.

None of this makes pantyhose a requirement for femininity. A woman in bare legs is fully dressed, and a crossdresser need not wear hosiery to complete some imaginary checklist. The best reason to wear it is that you like how it looks and feels.

Still, I appreciate the irony.

For some women, freedom meant no longer having to wear pantyhose.

For some crossdressers, freedom meant finally being able to.

And somewhere between those two experiences is a department-store hosiery counter—and someone hoping her favorite shade has not been discontinued.

Wearing ShopBop

John Hunter, Australian female impersonator, circa 1952

What Is It About High Heels?

What is it about crossdressers and high heels?

Ask a dozen of us and you will probably get a dozen answers—although several of us may be too busy admiring your shoes to answer immediately.

For many of us, heels have an appeal that goes well beyond matching a dress. They represent femininity, glamour and something we once could only admire from a distance. Slipping into a pair can feel like finally accepting an invitation that has been sitting on the mantelpiece for years.

Then there is what they do for an outfit. A pair of pumps can give a skirt suit a polished finish. Strappy heels can make a simple dress feel ready for an evening out. And if you happen to enjoy showing off your legs, as I do, the appeal hardly requires an explanation.

Heels also make you aware of how you move. Your stride changes. You pay attention to where you place your feet. There is something rather satisfying about hearing your own heels clicking along a sidewalk—especially when, once upon a time, you wondered whether you would ever have the nerve to walk down that sidewalk en femme.

For someone who spent years dressing only at home, that sound can announce a small personal victory.

Of course, my relationship with heels comes with an obvious complication: I am six feet tall before I put them on.

Add four-inch heels and I am approaching six-foot-four. Nobody is going to mistake me for the petite woman who slipped quietly into the back of the room. I may want to blend in, but my shoes apparently have other plans.

Still, I like the look. Tall women wear heels, too, and I have never believed that enjoying a pair should require meeting a height restriction.

There can also be an emotional history tucked inside a shoebox. Perhaps pumps remind us of a stylish woman we admired, a department-store display we lingered over or the first pair we finally bought for ourselves. To someone else, they are merely shoes. To the wearer, they may carry years of anticipation.

And yes, for some crossdressers, heels have an erotic appeal. For others, the pleasure is about fashion, feminine expression or the satisfaction of seeing the person in the mirror look the way they had imagined. There is no single explanation that fits every foot.

Nor does every crossdresser love heels. Plenty prefer ballet flats, loafers, sandals or sneakers. A woman does not become less feminine when she changes into comfortable shoes, and neither do we.

I enjoy my heels, but they are not an entrance requirement for womanhood—or for a successful afternoon out.

Sometimes, though, you put on a dress, add your earrings, pick up your handbag and look in the mirror. Then you step into the right pair of pumps.

And everything comes together.

Wearing Boston Proper

Jonny Beauchamp

Happy Halloween Weekend!

Notes on Going to Work Dressed as a Woman on Halloween

I did it seven times. The last time was ten years ago—my final Halloween at work before I retired.

It still amazes me that so many of my co-workers had no idea who I was until I spoke. Even then, a few still did not put two and two together.

And when I ventured out among civilians on those Halloweens, I think most people had no idea I was a guy.

One Halloween, I went to Stop & Shop during my lunch hour to pick up a few groceries. I checked out with a cashier whose line I had been through many times before. In boy mode, she was always cool and businesslike with me. In girl mode, she was positively friendly.

On another Halloween, I went to a restaurant for lunch by myself. The waitress was friendly and professional, but she never mentioned my “costume,” even though she gushed over the costumes worn by a couple sitting nearby.

After paying my bill, she returned with my change and I asked, “How do you like my Halloween costume?”

She gave me a blank look.

“What is it?”

“I’m a guy.”

She was shocked. She had had no idea! Then she began gushing over my “costume,” telling me how much she loved my hairdo—actually a wig—and how “cute” my nails were.

That was a very happy Halloween!

Wearing Alice + Olivia

Serban Copot (center) femulating Daniela Crudu on Romanian television's Te cunosc de undeva!

Happy Halloween!

She’s Wearing My Dress!

Watching the noon news on WFSB Channel 3, I couldn’t help noticing that the newscaster was wearing the same dress I own—one I bought from Venus three years ago.

Besides enjoying the coincidence, I was surprised to see her wearing a dress that had been around for three years. I always thought people who appear on TV wore the latest fashions.

I guess not!

So, who wore it better?

Wearing Boston Proper

Irish actor and comedian Jimmy O'Dea crossdressed in character as Mrs. Biddy Mulligan during a 1943 recording of a BBC radio show.

'Tis the Season

Vacation

I am taking a vacation. See you later.

The New (Wo)men

War Stories