Penny's Believe It Or Not

By Penny from Edinburgh 

Facing three years in prison, a young con man goes on the run. To avoid being caught by the police, he disguises himself as a woman. Because he bears a strong resemblance to his sister, he is able to use her identity and ID card. As time passes, he medically transitions.

Eight years later, the authorities finally catch up with him—or perhaps I should say her—after discovering that the sister’s credit card is being used locally while she is out of the country.

It sounds like a plot from Fictionmania, BigCloset or some other trans-fiction website, but according to a report by Turkey’s Dunya News, it actually happened in Istanbul.

Of course, most plots on trans-fiction sites are complete nonsense, but a few have actually played out in real life.

John “Virginia” Bone

I came across several examples while browsing old press clippings at the Digital Transgender Archive. These particular stories are British because that is the part of the archive on which I focused, but I am sure it contains many similar reports from the United States and elsewhere.

I found two stories about young men who dragged up and won conventional beauty contests. In 1968, John Bone got all glammed up as Virginia and was crowned Essex University’s Charity Queen. The following year, 17-year-old Harry Blathwayt won the beauty competition at the Horning Regatta in the English county of Norfolk and became Miss Horning.

“Head Made Boy Dress as a Girl,” reported the News of the World in 1968. The reason for the punishment? The 12-year-old boy’s hair was too long!

The boy was mortified, and his father removed him from the school. I suspect more than a few readers of this blog are thinking, “If only it had been me.”

The rather more upmarket Daily Telegraph reported in 1985: “Handbag Attack by Sex-Change Actress Over PC’s ‘He’ Jibe.”

The actress in question was April Ashley, one of the earliest Britons to undergo gender-confirmation surgery. She had been one of the parties in the 1970 English legal case Corbett v Corbett, which ruled that a person could not legally change sex. On that basis, her marriage to the Honourable Arthur Corbett was annulled. It would be many years before legislation overturned the effects of that decision.

In 2013, Rupert Murdoch’s famously sensationalist Sun newspaper ran the headline “Sex-Swop Doc in Stag-Gore Horror” after a red deer stag attacked scientist Dr. Kate Stone. This report did not come from the Digital Transgender Archive.

Stone subsequently complained that publishing her transgender status was an intrusion because it was irrelevant to the story. However, it may have been relevant in an unexpected way: It was suggested that the stag singled her out because she was the tallest member of her walking group.

My favorite transgender newspaper clipping, however, has to be the 1985 story of Dean—later Dena—Steers, a young preoperative transsexual who was taking hormones and always wore women’s clothing.

Dena was arrested for using the ladies’ restroom. Then, while out on bail for that offense, she was arrested again—this time for using the men’s restroom!

Sometimes truth really is stranger than trans-fiction.

Wearing Boston Proper

Femulating in Mount Enterprise, Texas in 1981

Womanly Yours

Is Crossdressing Becoming More Popular?

Or Just More Visible?

Every so often, someone will ask, usually with a raised eyebrow and a tone somewhere between curiosity and concern, whether crossdressing is suddenly “on the rise,” particularly among younger men.

It’s a fair question. Walk through certain corners of social media, browse fashion editorials, or spend ten minutes people-watching in the right urban neighborhood, and it can feel like something has shifted. The old lines, once thick, permanent, and aggressively enforced, now look faint, negotiable, even optional.

But before declaring a full-blown trend, it’s worth slowing down. What we’re witnessing is not quite what it seems. Because the real story isn’t that crossdressing has exploded. It’s that the silence around it has.

For decades, men who wore feminine clothing existed in a kind of cultural shadow. Some did it privately, some occasionally, some as part of a deeper identity, and some simply because they liked how it looked or felt. What they shared was not necessarily motivation, but invisibility. Social cost kept things quiet. You didn’t see it because people made sure you didn’t.

That pressure hasn’t vanished, but it has weakened. And when pressure eases, visibility rises.

Younger men, in particular, are growing up in a different atmosphere. They’ve inherited a culture where gender rules are no longer handed down as commandments but offered more like suggestions. Try this. Don’t try that. See what fits. Ignore what doesn’t.

That doesn’t mean they’re all crossdressing. Far from it. Most aren’t. But more of them are willing to experiment... once, occasionally, or in specific contexts without assuming it defines their entire identity. A skirt might be a fashion choice. Makeup might be aesthetic. Presentation might be fluid, situational, or even playful.

And that’s where the confusion creeps in.

We tend to collapse everything into one category: crossdressing, identity, lifestyle, orientation, as if they’re interchangeable. They’re not. A young man trying on a different presentation for a night out is not necessarily making a broader statement about who he is. He may be. Or he may just be trying something on, in the most literal sense.

What’s new is not the behavior itself. It’s the permission.

Of course, it’s not universal. Geography still matters. So do family, workplace, and social circles. In some places, the old rules remain firmly in place, and stepping outside them still carries real consequences. Even where acceptance is higher, there’s often an unspoken line between what is “edgy but acceptable” and what crosses into discomfort.

So no, we’re not looking at a tidal wave of young men abandoning traditional dress overnight. What we are seeing is something quieter and, in its own way, more significant.

A gradual loosening. A willingness to question what used to be unquestionable. A shift from “never” to “maybe,” and in some cases, to “why not?”

And once that shift happens, even a small number of visible examples can feel like a cultural surge. But it isn’t a surge. It’s a reveal. The men were always there. They’re just harder to ignore now.

And so it goes.

Wearing Alice + Olivia

John Hurt femulating in the 1975 British film The Naked Civil Servant.

In Touch

It started, as these things often do, with something small and entirely deniable.

“Just curiosity,” said Frank, holding up a tube of tinted lip balm in the pharmacy aisle like it was evidence in a trial. “Practical, really. Winter dryness.”

His wife, Carol, didn’t even look up from comparing two brands of moisturizer. “Of course. Hydration is important.”

That was a Tuesday.

By Friday, Frank had “accidentally” discovered that Carol’s cardigan was “surprisingly comfortable.” By Sunday, he had opinions about fabric drape. And by the following week, he was standing in front of the bedroom mirror, turning slightly to the left and then the right, asking a question no man in his bowling league had ever asked out loud:

“Does this color wash me out?”

Carol, to her credit, adapted quickly. Some spouses resist change. Carol organized it.

“Well,” she said, arms folded, evaluating him with the same calm authority she once used to choose kitchen appliances, “if you’re going to do this, we’re going to do it properly.”

That was how Frank found himself booked for a “consultation.”

---

The salon had a name that suggested both luxury and inevitability: Refinement.

Inside, a row of men, formerly known as guys, sat in plush chairs, each at a different stage of what could only be described as… progress.

One was having his eyebrows shaped with the solemn intensity of a sculptor restoring a Renaissance statue. Another was being fitted for something that involved boning, lacing, and a level of commitment Frank had not anticipated.

Frank swallowed. “I thought maybe we’d start with… a scarf.”

Carol smiled. “We are starting with a scarf.”

Two hours later, Frank emerged with a softly layered haircut, a light application of makeup, and a scarf tied in a way that suggested he had opinions about art galleries.

He looked… good.

Annoyingly good.

---

The shift spread faster than anyone expected.

At the office, it began with small changes. A bit of moisturizer here. A neater haircut there. Then came the cardigans. Then the shoes.

Within a month, Casual Friday had been replaced by what HR cautiously called “Expressive Presentation Day.”

Frank, now frequently referred to by Carol as “Frances, when he’s making an effort,” found himself mentoring younger men.

“You’re rushing it,” he told Kevin from accounting, who had shown up in a dress that clearly had not been chosen with his proportions in mind. “You need structure. And better shoes. Those are… optimistic.”

Kevin nodded solemnly. “I thought the heels were the point.”

“They are,” Frank said. “But not like that.”

---

Meanwhile, the women adapted in their own way.

Carol bought three new pantsuits. Not because she needed them, but because she enjoyed the symbolism.

At social gatherings, the dynamic had shifted so completely that no one even mentioned it anymore.

Wives stood in small, confident clusters, discussing careers, investments, and travel plans.

Their husbands, now softer, neater, more… considered, stood nearby, comparing fabrics, adjusting accessories, and occasionally asking each other, in hushed but earnest tones:

“Be honest. Is this too much?”

---

The real turning point came at a neighborhood party.

Frank arrived in a tailored skirt suit, understated but precise, with a small brooch Carol had insisted on.

As he stepped into the room, there was a brief pause… the kind that used to happen when someone broke a social rule.

But now?

A nod.

A smile.

A quiet, collective acknowledgment: Yes. That works.

Carol slipped her arm through his. “You clean up well.”

Frank exhaled, just slightly. “I was going for… put together.”

“You succeeded.”

Across the room, Kevin from accounting was explaining pleats to someone who looked deeply overwhelmed.

Progress.

---

Later that evening, as they walked home, Frank adjusted his scarf against the cool air.

“You know,” he said, “I didn’t expect it to feel like this.”

“Like what?”

He thought for a moment.

“Like I’ve been underdressed my whole life.”

Carol laughed, not unkindly. “Most of you were.”

He glanced at her. “And you’re okay with all this?”

She considered the question, then gave a small, satisfied nod.

“Oh, I’m more than okay with it,” she said. “I’ve been waiting years for you all to catch up.”

Frank looked down at his high heels, good shoes, he now knew, and then back up the street, where a few other couples walked ahead, the silhouettes just slightly different than they used to be.

“Funny,” he said. “All it took was getting in touch with our feminine side.”

Carol squeezed his arm.

“And a little guidance,” she said.

Wearing Boston Proper

John Hansen (center) femulating in the 1970 film The Christine Jorgensen Story.

Downsides of Crossdressing

Pammy asked, “Are there any downsides to crossdressing?”

If you’re asking honestly, then yes, there are downsides. It’s better to look at them clearly rather than pretend it’s all upside. Whether those downsides matter depends on the individual, the situation, and how it’s handled.

Here are the areas where things can get complicated:

Social consequences are the biggest factor. While attitudes have improved, negative reactions still exist especially in more conservative environments. In some workplaces or communities, being “outed” can create real problems. Partners, friends, or family members may struggle to understand or accept it. It may not be fair, but it is reality. You have to decide how much visibility you’re willing to risk.

Relationships can also be affected. Crossdressing can introduce confusion, insecurity, or mismatched expectations between partners. One person may see it as occasional expression, while the other sees it as something much more significant. Secrecy tends to make things worse if it’s hidden, it often damages trust. The hard truth: avoiding honesty early on usually leads to bigger problems later.

Emotional patterns are another area to watch. For some, it’s not always harmless fun. Cycles of enjoyment followed by guilt can develop. There can be a tendency toward escalation, that is, needing “more” over time to achieve the same satisfaction. Others may experience uncertainty about what it means for their identity. This is where self-awareness matters. If it starts controlling you instead of the other way around, that’s a red flag.

Financial cost is easy to underestimate. Clothing, shoes, wigs, and makeup add up quickly. Maintaining multiple wardrobes can become expensive, and trial-and-error purchases often mean wasted money. Without discipline, it turns into a quiet but persistent drain.

Safety concerns depend heavily on where and how you present. Public harassment, uncomfortable confrontations, or vulnerability in unfamiliar environments are real risks. Online exposure can also lead to ridicule or doxxing. Situational awareness isn’t optional—it’s necessary.

Time and energy can become significant. Grooming, dressing, and makeup take effort. Add in planning, logistics, or secrecy, and it can consume more mental space than expected. Like any hobby, it can crowd out other priorities if left unchecked.

For some, but not everyone, it can become habit-forming or compulsive, especially if it’s tied to stress relief. If it starts to feel like something you have to do rather than something you choose to do, that’s worth paying attention to.

Bottom line: crossdressing itself isn’t inherently bad. The downsides come from how it fits into your life, how honest you are about it, and whether you’re in control of it…or it’s in control of you.

If you keep it intentional, grounded, and integrated with the rest of your life, most of these risks can be managed. But if it becomes secretive, compulsive, or starts colliding with your relationships and responsibilities, that’s when the real costs show up.

Wearing Boston Proper

Bruce Watson femulating in an episode of television’s Charlie's Angels, 1981.

Dressing for the Weekend

Men Being woMenly

Choices

We make choices everyday.

(Boxers, briefs or panties? Yogurt or bagel? Bra or bra-less? Regular or decaf?)

Some choices are more important than others and some have long-term ramifications.

(Should I be a doctor, a lawyer or a fire chief? Should I marry her, him or it?)

Sometimes our choices backfire. Sometimes our choices are just plain wrong and we suffer the consequences, but we are still free to choose whatever we want.

So why can’t we choose our gender?

Despite all the scientific evidence to the contrary, the anti-transgender crowd claims that transgender folks choose to be transgender just like the anti-gay crowd claims that gay folks choose to be gay. And according to those crowds, making those choices is wrong.

I am naturally feminine. My feminine speech and mannerisms are a bad fit in boy mode, but in girl mode, they are a perfect fit.

I could man up and never wear a dress again, but I chose not to impersonate a male. So, yes, I made a choice to live authentically and not fit in with the boys.

But what if I was not transgender?

What if I was a guy with no gender issues, who carefully weighed all the options and decided that living my life as a woman was preferable to living my life as a man. And as a result, chose to live life as a woman.

What's wrong with that?

I say, “Absolutely nothing.”

It is just another choice. Admittedly, it is a big choice with a lot of long-term ramifications, but humans make important choices everyday. That’s why God gave us intelligence and free will ― so that we can make choices ― like choosing our gender.

Wearing Bebe

Patrick Walshe McBride femulating on British television’s Shakespeare & Hathaway: Private Investigators.