First Time

Monday’s post was about the second time I crossdressed. In reverse order, today’s post is about the first time I crossdressed.

I was 12-years-old in 1963 and became fascinated with female impersonation when I noticed weekly thumbnail-sized ads in the New York Daily News for 82 Club. Each ad depicting  a glamorous showgirl accompanied by the caption “Who’s No Lady?”

The 82 Club showgirls were female impersonators and I was amazed that a male could emulate a glamorous female! I was so impressed that I began clipping the 82 Club ads out of the newspaper each week and hiding them behind the Washington Senators in the box containing my baseball card collection. 

One thing led to another and one afternoon when I was home alone, I went into my parent’s bedroom and opened the drawer of my mother’s bureau where she stored her nylon stockings. (This was in the days before pantyhose and seamless stockings were popular, so her nylons had seams.)

I carefully slipped a stocking up each of my hairless legs (those were the days!) and straightened the seams. When I was done, I opened my mother’s closet door to admire myself in the full-length mirror mounted on the inside of the door.

I liked what I saw: a pair of legs that looked just like a pair of woman’s legs! Then I realized that I could do even better. 

Inside the closet were stacks of shoeboxes containing my mother's shoes. I carefully looked through the boxes for a pair of high heel pumps. When I found a pair (with a three-inch heel), I slipped them on and revisited the full-length mirror.

Not only did I see a pair of woman’s legs in the mirror, but they were now a shapely pair of woman’s legs! I proved to myself that that a male really could emulate a female.

I quickly, but carefully removed the shoes and stockings and returned them to their proper place before my family returned home. And I assure you that would not be the last time I would visit my mother's bureau, closet and full-length mirror.

Wearing Max Mara

Femulating professionally at 82 Club.

Or Sox

Wearing Farm Rio

Richard Lane and Edward Brophy femulating in the 1946 film Girl on the Spot.

Second Time

After donning my mother’s nylon stockings and high heel shoes and discovering that I was able to emulate the shapely legs of a woman, I just had to push the envelope further. The next time I was home free to explore my mother’s wardrobe, I repeated my first time, that is, I slipped on a pair of her nylon stockings and high heel shoes.

I was well aware of the options available to women of the early 1960s to keep their nylons up and their seams straight. In my mother’s case, she used the garters that were attached to a girdle. I found her stash of girdles in a drawer of her bureau and had to choose from a variety of styles: open bottom, panty brief, long leg panty, high-waisted panty and high-waisted long-leg panty. I figured I needed all the help I could get, so I selected a high-waisted long-leg panty model.

I unzipped and unclasped the girdle, stepped into it and tugged it up over my legs, hips and waist. When I was finished squeezing into it, I closed its clasps and zipper with some difficulty. When I was done it felt like half of my torso was in the grips of a rubber vise.

After I attended to the nylons – straightening their seams and attaching them to the garters of the girdle – I swung open the closet door, viewed myself in the full-length mirror and concluded that the picture was incomplete.

The girdle had redistributed my “baby fat.” As a result, my waist was narrower and my hips were wider, but above the waistband of the girdle, a ring of displaced fat encircled my body and ruined the picture.

I was sure I knew how to fix it – it was time for my first bra!

My mother had a small selection of bras to choose from and they were all similar in style and size, so I randomly grabbed one and tried to figure out how to put it on.

I struggled unsuccessfully to close the bra’s clasps while wearing the bra with its cups in front. So, I slipped the straps off my shoulders, twisted the bra around with the clasps in front of me, closed the clasps, twisted the bra back around and slipped the straps over my shoulders – and that’s the way I have been putting on a bra ever since.

After adjusting the straps of the bra, I was astonished that my breasts nearly filled the cups of the bra! My “boy boobs,” which were the object of ridicule by my peers, now had a safe place to call “home.”

And when I revisited the full-length mirror, the picture was now complete; there was the body of a shapely woman in the mirror’s reflection.

By the way, recalling my second time crossdressing, I realized that the event occurred in 1964 – 60 years ago. 

And so time goes.

Wearing Bebe

Frederick Weller femulating in television’s In Plain Sight.

High on Heels

Wearing Bebe

Paolo Ballesteros femulating in the 2016 Filipino film Die Beautiful.

Notes from the Changing Room

Let me preface this with the fact that I am a large person. Until late 2017, I weighed 215 pounds to go along with my 6-foot 2-inch height. I dropped 30 pounds in 2017, so I am still a large person at 185 pounds. My height more than the weight kept me closeted for a very long time, but when I finally began exploring my female persona in public, I found that my size was not a deal breaker. 

Using the changing room en femme was easy. Using the changing room en homme was just as easy. I lost count how many times I used the changing rooms in Fashion Bug, Dress Barn, Fashion to Figure, Torrid and Macy’s to try on womenswear during a lunch hour while disguised as a male.

I can recall only one “negative” experience. It occurred a very long time ago. Shopping for a girdle en homme in JCPenney, when I asked to try it on, the saleswoman insisted that I use the men’s changing room. Not a big deal, but that was the only changing room experience that I can come up with that had any negativity.

The layout of the dearly departed local Dress Barns had changing rooms scattered around the perimeter of the sales floor. They also had a changing room area in the back of the store. The first few times I visited Dress Barn en homme, I was sent to the back-of-the-store changing room. But as I became a regular customer and the sales staff knew me by name (both male and en femme names), I was invited to use the more public perimeter changing rooms, which was delightful when I was en femme because it gave me the opportunity to exit the changing room and view whatever I was trying on in the three-way full-length mirrors outside the changing room. And doing so invited the sales staff and even customers to comment on what I was wearing. The sales staff usually liked what I was wearing (to make a sale), but when a stranger says they liked what I was wearing, it was a home run and that’s where I went with my new dress.

And so it goes.

Wearing Ann Taylor

Nadia Russo

It was terrifying!

“It was terrifying!” were the words of a novice femulator after she used a woman’s changing room to try on clothes for the first time. 

Been there, done that. It should be a pleasant experience not a terrifying experience, but just like anything else, practice makes perfect and after a few visits to the changing room, you won’t think twice about it. However, here are some tips I use to make sure that the experience is pleasant. 

👠 If a store associate is available when going to the changing room to try on your finds, play dumb and ask where the changing rooms are located (even if you know). I do this whenever possible for insurance purposes, that is, if somebody complains about a dude in the lady’s changing room, the dude can say that’s where the store associate told me to go.

👠 Take as many outfits as possible to try on when you go to the changing room. Some stores limit the number you can take in, some don’t, but in any case, go for the max in order to minimize the number of times you have to change your street clothes.

👠 Shop at smaller women’s clothing stores rather than big department stores. You won’t get a lot of hands-on assistance in large department stores, however, you usually will get assistance in smaller women’s clothing stores. For example, when you are ready to try on your finds, an associate will “start” a changing room for you (your very own queendom) and sometimes they will even put a sign on the door reserving that room for you with your femme name emblazoned on the sign. And if something is the wrong size, the associate will fetch another size to try on saving you the trouble of getting back into your street clothes to do the fetching yourself.

👠 In smaller stores, savvy associates will size you up and recommend clothing for you to try on. This has happened to me more than once and I ended up trying clothing on that looked great on me, but I would have never given a second look if the sales associate had not made the suggestion.

👠 Speaking of street clothes, wear an outfit that you can strip off and put back on easily. I own a sweater dress that has a full-length zipper in front, which is perfect for quick undressing/dressing. Jumpsuits also work well, but skirt suits don’t.

👠 The associates want to sell, so if they compliment you on what you try on, take the compliment with a grain of salt. If you go shopping with a friend, your friend’s compliments may not be any more valuable than the store associate’s because your friend may not want to hurt your feelings. So here is a way I get an independent appraisal of what I am trying on… I step out of the dressing room on the pretense of viewing myself in the full-length mirrors usually hung throughout the store. My goal is for another customer to see me while I am doing this. If they gush over what I am wearing, it is a bingo! Whenever I have done this, other customers always check me out while I am checking me out and if they like what they see, they let me know.

👠 For a quick self-appraisal, take a selfie or have an associate take your photo. The difference between what you “see” in a mirror and what you “see” in a photo is surprising ― trust the photo, not the mirror.

Shopping for women’s clothing is almost as much fun as wearing women’s clothing! So, you go girls and have some fun!

Wearing Gracia

Alex Newell femulating in an episode of television’s Glee.

That's What She Said

I am a big fan of Steve Carell’s version of The Office. After rewatching many episodes of the show, I started picking up clues that Steve Carell’s character, Michael Scott, might have a feminine side. So much so that I created the Michael Scott en femme images that you see above and on Sunday’s post. Anyway, here are the clues that come to mind.

Michael Scott “mistakenly” purchases a woman’s pantsuit (MISSterious brand) and wears it to work. (Season 3, Episode 19, “The Negotiation”)

Michael Scott confesses that his girlfriend, Jan, forces him to wear a schoolgirl dress when they have sex. (Season 3, Episode 22, “Women's Appreciation”)

Pam, the receptionist, states that Michael Scott identifies with Meryl Streep’s portrayal in The Devil Wears Prada. (Season 4, Episode 7, “Money Part 1”)

Michael Scott states, “Dunder Mifflin is about to be sold. But first an investment banker has to drop by and sign off on our branch. And I’m... pretty nervous about it. And I’m... making some cosmetic tweaks to help create a more appealing environment. Is that dishonest? Well, think of it this way: when you look in the mirror and you see your push-up bra and your fake eyelashes and your make-up and your press-on nails; the principles that I am applying to the office are the same ones that have made Lady Gaga a star... or any number of drag queens.” (Season 6, Episode 14, “The Banker”)

Michael Scott purchases pants from Talbot’s, a retailer of women’s clothing, and is undecided whether to return them, not because of the fit (because of the style?). (Season 7, Episode 1, “Nepotism”)

Michael Scott makes the following suggestion to co-worker Gabe: “A little cover up on your Adam's apple will make it appear smaller, which will make you look less like a transvestite. (Season 7, Episode 22, “Goodbye, Michael”)

And so it goes.

UPDATE: Another clue: Michael Scott says that he receives Victoria’s Secret catalogs at home that he claims were the subscription of the previous tenant of his apartment. (Season 6, Episode 23, “Body Language”)

Wearing Venus

Zach Woods dressed as Lady Gaga for a Halloween episode of television's The Office.

Can't Be Beat

Wearing Tory Burch

The Kinky Boots Angels on stage in Phoenix, 2014

Affirmation

How do I look?

Everyday I receive an email summarizing the postings on the crossdressing subreddit, which seems to be populated mostly by young ladies rather than old ladies (like me). They are just starting out on the remarkable road of crossdressing, but they hardly look like novice men in dresses – they already look like the young ladies they are striving to be. (“Youth is wasted...”)

Despite their drop-dead gorgeous appearance, a typical email post will ask the other members of the subreddit, “How do I look?” 

Unsure about their presentation, they are reaching out for affirmation that they are on the right path to achieve their feminine goals to be able to safely step out of the closet and experience the world en femme.. Positive emails build their confidence and out the door they go. 

Back in the day, most of my sisters could not dress to the nines and ask for feedback about our presentations before stepping out. (“Hey, Pop. How do I look in these new high heels?”) 

No, we had to gird our loins, open the door, step out into the real world and hope for the best. If people did not stare, laugh or point at you, that might be the best affirmation you could expect. Not the greatest confidence-builder, but it was something.

On the other hand, if you were called “Ma'am,” or even better “Miss,” that was our equivalent of receiving positive responses on reddit.

And so it goes.

Wearing DailyLook

Michael Scott

A Night at the Opera

 

Wearing Boston Proper

Helénia Melán and Jorge Chacón