Dina’s Diner 6/26/23

Dina’s Diner 6/26/23

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A few years ago I wrote about Womanless Beauty Pageants that were prevalent in some parts of the country. Based on the sparse details I could uncover, Womanless Beauty Pageants were usually organized by high schools and middle schools presumably as a fundraising event. The pageant contestants were boy students who would be dressed in gowns, wigs, sometimes high heels, also sometimes lipgloss or eye makeup to enhance their feminine appearance.

A Womanless Pageant contestant.

Internet photo sites like Pinterest and Flickr have many photos snapped at the events. It was difficult to find any actual reporting about the events. Some of the photos showed the boy contestants with family members, other contestants dressed up, and occasionally girlfriends at the pageant events.

For whatever reason, there haven’t been any new photos of the pageants posted for several years. The same photos keep popping up on Pinterest user feeds now. The presumption is that the pageants are a thing of the past.

That comes as no surprise to me given the conservative drift in some parts of the country. The interesting thing about the pageants is that they seem to have occurred in Bible Belt areas of the South and Midwest. It always seemed like an anomaly that the more conservative regions would be having drag pageants for school-age boys on public property and supported by parents and the communities.

So you can imagine that with the strident rise of anti-LGBTQ, anti-drag sentiments the pageants would be banished from the school calendars and probably erased from the collective memory of those communities nowadays. By the way, it was clear from the photos that the pageants were something of a burlesque of silliness and were not promoting or even referencing any gender or sexual identities by the participants.

The sad part is that some of the past participants in the Womanless Beauty Pageants may now be part of the anti-drag, anti-LGBTQ sentiments in their conservative communities. If anything the pageants show that drag or vamping around in a comical pageant is not ‘grooming’ and the participants (most likely) went on with their lives as straight young men.

Someday when this anti-drag, anti-’woke’ small minded nonsense runs its course, maybe fun, positive community traditions like Womanless Beauty Pageants will return.


The Huffington Post online news and culture site had an article in their Queer Voices section headlined The Hidden Cost of Finding Queer Community. It appeared on the site June 9, 2023 as part of a series on financial issues for LGBTQ folks.

The author, Ian Kumamoto, mentions that — unlike hetero people — LGBTQ people are not surrounded by other queer folk at work, in their apartment buildings, in stores and restaurants, etc. unless they go out and find places where other queer people hang out. Ian writes, “Anytime I’ve wanted to be around other queer people, even in a city like New York, I’ve had to make a concerted effort to do so. More often than not, that means spending money — sometimes a lot of it — to go out to the club or bar.”

He also points out that LGBTQ people who grow up in small towns or conservative areas often want to migrate to cities like New York or San Francisco to be part of a gay community and that involves quite large investments in moving, housing, and other living expenses.

Trans woman Solar Rodriguez told Ian that she “often had to travel [from the Bronx] to Brooklyn, which is known for its more inclusive queer scene, in order to attend parties and events that were welcoming to trans people. Because those events often happened late at night, she would have to take Ubers to increase her own safety. This meant charges of upwards of $120 round trip — and that’s not including any of the drinks or entrance fees she’d have to pay at the parties themselves.”

Ms. Rodriguez also said that “she feels a pressure to look “a certain way” so that she’s respected and not misgendered. This usually involves makeup, a pricey wig and an outfit that affirms her gender identity. “For me, when I go into a community, I want to be seen and accepted,” she tells me. “When you look good, you feel good.””

To someone on the outside, it may seem like somewhat frivolous concerns: spending on nightclubbing, or cosmetics, or Ubers. But a financial planner who works with queer clients tries to “help them make intentional choices around spending. Every dollar you spend is a tradeoff for the energy you spend to earn it,” she says. “If someone finds that their clothing and makeup is essential to their identity, then that must be a highly valued expense. I would suggest finding tradeoffs in other areas where they could cut costs or put energy towards increasing their income.””

I think we have somewhat the same issues in the crossdressing community. Aside from the obvious clothing, cosmetics, and wig expenses, finding community with other crossdressers can be expensive. Inexpensive support groups are virtually non-existent anymore. Even gay bars have dwindled over the past decade or two, narrowing nearby opportunities for many crossdressers to get out in a public venue. Events like Angela Gardner’s Laptop Lounge in the Philadelphia suburbs are few and far between. [Editor’s Note: The Laptop Lounge is currently on hiatus due to low attendance.] What is left are some larger convention-style gatherings like Diva Las Vegas or The Keystone Conference, and maybe others I’m not aware of. But those require the admission cost, hotel rooms, travel expenses, and incidental costs during the event.

There are thousands of crossdressers on internet sites trying to connect or at least see other crossdressers on photo sites, etc. There is a psychic cost to isolation — a point brought up in the HuffPost article too. One must evaluate the social opportunities available and then balance out the financial equation of going out or attending an event versus the psychic cost of NOT connecting with others. Over time, that psychic cost of isolation could outweigh the financial aspect.


I was browsing around the internet recently and came across a blog post titled From A Bewhiskered Crossdresser. It was written by Geena Kirkland and it appeared on the site CrossdresserHeaven.com on June 3, 2023.

Conchita Wurst

Facial hair is an issue for many crossdressers who don’t wish to shed their beard or mustache which is part of their masculine identity. Geena is one such case and some of the commenters to her blog post were in the same situation. It may even be more prevalent than in the past because the stubbly look, if not a full beard, is now a common look for men.

Like a lot of crossdressers who have facial hair, Geena dressed but did not do makeup or wigs. She writes, “Although I was still bearded, I was greatly enjoying the feeling of dressing feminine, and took digital photos with my face cropped out.” She went on to say that Covid face-masking gave her enough cover to venture out en femme to parks and even in a store at least once.

Geena writes then of an interesting revelation. “In January of 2022 I got grudging approval to clean off the beard. I did it in stages over a few days, leading up to the moment of truth. For the first time in over 40 years I saw my clean shaven face, and was horrified! I saw a weak chin, turkey neck, and the beginning of jowls!” And it turns out that the new freedom to dress as a more natural looking Geena was disappointing because she was not proficient with cosmetics. Some time later, she met a crossdressing friend who helped her with makeup but now she was left with another dilemma. She didn’t like the way she looked as a man without the beard she had for decades. It’s always something, right?

Geena’s solution — and at least one commenter to her post echoed this as well — was to shave maybe once or twice a year with some cover story to family and friends and use that brief window to fully realize the en femme experience.

Conchita Wurst, who won one of the Eurovision singing contests several years ago is perhaps the most famous crossdresser/drag artist with facial hair. On her it actually looks pretty sexy, I admit to myself and (now) the world. Some of the male makeup influencers on Instagram sport facial hair, usually that stubbly beard look that is popular with the younger set. But as something of a traditionalist/old fogey, I definitely prefer the shaven, cosmeticized face for crossdressing purposes. Care to change my mind?


Taylor Swift

The Taylor Swift Eras Tour recently played Pittsburgh, Pa. and (perhaps like all her event venues) it was quite the happening all over town. One of the restaurateurs in downtown near the stadium that Taylor sold out said it was a better crowd dollar-wise than a Steelers game day. Besides the 73,000 in the stadium, a lot of people showed up outside the stadium to listen and take in the overall vibe. Swift also attracts a family friendly crowd so lots of moms and dads were there with their daughters adding to the civic celebratory atmosphere.

I don’t count myself as a Taylor Swift fan. But I have admired how she’s grown into a now-33 year old beauty and, yes, sex symbol. I had to look at a Wikipedia entry to read more of her history. She started out as a teen sensation doing mostly country music. Then she crossed over into mainstream pop and became a true sensation with multiple awards of almost every type on her mantle now. She writes her own songs and actually plays multiple instruments which is always impressive to me. But I never thought of her as a sex symbol until very recently.

The lesson for all of us who are beyond the tween or twentyish age group is that some age helps in the beauty department. In Taylor’s case, it seems like she has filled out a little (or maybe quite a lot) from the tall (5’11” they say) and thin build she carried for most of her celebrity years. Now with a softer appearing face and much softer and curvy build, the stage makeup and spangly bodysuits and tights have pushed her to va-va-voom territory. Not being a big fan of popular music, the one thing I always like about contemporary female singers is the stage costuming. What crossdresser wouldn’t like to come out in front of seventy-three thousand fans in a rhinestone leotard, fishnet tights, and silver stilettos?

Pop stardom dreams die hard, I guess. But my point here is that you may look better now with a little more meat on your bones (if not an entire extra bolar roast), than you did when you were just an ingenue. Let’s keep telling ourselves that, ‘kay?


I saw a posting on Reddit.com that featured models body painted as shoes. I think I’ve seen this before but I’m not sure. As you can see with the photo here, it is hard at first glance to see that the object is not an actual high heeled shoe.

Not a shoe?

The original Reddit post was removed for reasons unknown but there are some videos of a few models painted as high heel shoe designs. And some videos showing how the models get into the poses required to create the optical illusion. It’s quite interesting to see how they did it.

The trick of the artwork is the 3D effect of painting in the shadow and depth of the inner shoe walls to ‘fool’ the eye and camouflaging the body within the design. Only after you’ve seen it a few times can you discern the model’s head and arms within the ‘shoe.’ It’s a lot like those 3D sidewalk chalk art designs that appear to be crevices or wavy sections in the walkways.

The artist is Johannes Stotter, a famous body painter from northern Italy. He described his his process to the website (fittingly) named Italian Shoes.

Anyway, since crossdressers generally love shoes — especially high heeled shoes — which design would you prefer or wish to model as?

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Category: Transgender Fun & Entertainment


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