Many Halloweens Ago

By Carollyn Olson

Other Captain & Tennille Emulators 

Unlike many crossdressers, Halloween has never been one of my favorite “holidays.” 

It’s not that I don’t enjoy the children knocking on the front door for “trick or treat” candy because I like seeing the little ones in costume, especially when a boy is dressed as a girl. What I don’t like is when men dress as women once a year and flaunt themselves in an embarrassing way, which is negative to the crossdressing community and all we strive and stand for the other 364 days a year. Is this understandable?

About 30 years ago when I was basically a less experienced crossdresser, I had the opportunity to do a costume exchange with my loving wife for a good friend's combination Halloween and birthday party. 

A few months earlier, my spouse and I had dressed as the popular singing duo Captain & Tennille at a company convention/theme night. It was her idea to “blow our friends’ minds” by reversing roles for the Halloween/birthday dinner party.

When my wife asked me if I was interested in switching roles, I “manly” shrugged it off, but mentally embraced the opportunity. “Let me think about it,” I said, not sure if she was serious, but knowing I would be agreeable in a couple of days.

Going to a party en femme was exciting. I had been out-and-about many times, but this was different. In my mind I began to prepare for the “big night.” What would I wear, where would I buy shoes, makeup, finger nails, jewelry, etc? Remember, I had been crossdressing for about 10 years unbeknownst to my spouse. I had plenty of clothes in a storage locker, but I could never tell he, so I wasn’t going to wear any of my femme wardrobe. I would start from scratch.

After agreeing to make the Halloween switch, we first worked on her costume: a captain’s hat I had worn at the company outing, a striped blue and white shirt, blue blazer, white pants and tennis shoes. I wanted her outfit to be perfect and she looked great, especially when her flowing blonde hair was stuffed under the captain’s hat. Then we went to work on mine.

Since we wore the same size dresses, she asked me to try on her undergarments, hose, red sweater dress and shoulder-length blonde wig. Everything fit perfectly. All I needed was a pair of heels and I knew where to go – Payless Shoes. A few days after the fitting, I returned home with black Mary Jane heels to complement the dress. I also bought clip-on earrings and press-on French tip nails. I was all set to make my Halloween debut.

The night before the party, my spouse insisted I shave my legs, which I did without hesitation. She suggested that we do a costume “dry run” to which I had little objection. Within an hour she had applied my makeup, I had dressed and was parading around the house in heels. She was amazed how good I looked, my mannerisms and how well I walked in 2-1/2–inch heels. If she only knew!

The afternoon of the big day, I started preparing about four hours before we had to leave. I wanted to be perfect and really surprise our friends. After shaving and showering, my spouse did an extra special application of my makeup. I proceeded to dress, making sure I added a little padding for my hips and my bra. My spouse combed out her wig so it would fall precisely on my shoulders. She handed me a matching red purse packed with makeup and said, “You look amazing, but I don’t want you to make a habit of this.”

My 20-ish daughter was also preparing for a Halloween party and she was aware of our party plans. I knocked on her bedroom door and when she opened the door she screamed in amazement. 

“I can’t believe you are my father,” she said. “You look so good as a woman.” 

We shared a good laugh as she had me twirl around and observed me walking in heels across the family room. I picked up our white kitten, which was following me step-by-step and my daughter took a couple of pictures for our photo album.   

I was a bit nervous when I drove the 20 minutes to the party and faked even more nervousness (for the sake of my spouse) as we walked to the front door. I actually felt comfortable and anxious for my friends to meet “Brandi,” the name my wife had given me. We were welcomed by the son of the host, who was a perfect match for Eddie Munster. 

As we walked in, we were greeted by our friend John, who was dressed as a monk. He was shocked at how great I looked and immediately wanted to take photos. Being a dirty old priest, he attempted to grab my breast, but I slapped his hand and told him to act like a gentleman. We had a good laugh as the camera clicked.

I spotted Howard across the room. He had his back to me, so I walked quietly up to him and tapped him on his shoulder. He turned around and I placed a big, wet kiss right on his lips. When he realized the woman who kissed him was me, he yelled an obscenity and ran off to the bathroom to clean off his lips. Everybody laughed.

My appearance as Brandi was the hit of the party. Before the night was over, I had won the best legs contest and many of the men tried to walk in my heels. Drinking alcohol and trying to walk in heels for the first time is not the best idea and one could imagine the results. Anne, the classy, lovely-looking lady, who was the runner-up in the legs contest whispered to me:, “You deserved to win. Your legs are much nicer than mine.”

My spouse chided me throughout the night for being vain. And why not? I was constantly checking my makeup and reapplying my mascara and lipstick in the bathroom. I wanted to look the best I could. 

We departed for home some time after midnight. Since it was colder than usual for a late October evening, the car windows began to fog up. I safely stopped the car at the side of the road and retrieved the squeegee from the trunk. As I was leaning across the hood of the car to reach the windshield with my dress riding up my thighs, a police officer pulled up and rolled down his window. 

“Is everything OK, Miss?” he asked. 

I informed him my windows were fogging up and I wanted to make sure I could see where I was going. 

“Good idea,” he responded. “Drive safely.” 

He turned on his flashing lights and accelerated on to the thoroughfare. I would never know if he turned on the lights for me or had an emergency call.

When we returned home, I poured my wife into bed (too many Long Island iced teas). Still on a high and not wanting to change, I decided to try on a few of my wife’s other outfits. I felt so femme as I wore some of her fancy and casual longer and shorter dresses. 

Finally, exhausted after 12 hours in heels, I fell into bed at 4 AM completely satisfied and on Cloud 9 after a night I will never forget.

So, what’s your Halloween story? I’d love to read it and share it with my readers. And don’t forget to send along a photo or two from your holiday in heels. 

Boys too can cut a pretty figure in this beautiful dress from Eloquii. 

Alex Saxon femulating on television’s Ray Donovan (2013 and 2015)
Thank-you, Gina, for tipping me off about this femulation.

Don’t Miss Miss

Miss is a new French film with the following plot (according to IMDb): “A young man seeking his sexual identity decides to take part in the Miss France beauty pageant.”

Sounds interesting from a femulator’s perspective, but to sweeten the pot, Alexandre Wetter plays the young man in question and he is absolutely gorgeous. So gorgeous that he is a male womenswear model, who I have featured in the Femulator slot about a half-dozen times.

A picture is worth a thousand words, so take a look at the images I captured from the film and I think you will agree that Alexandre’s femulation is not to be missed.

You can be a superhero when you wear this cape dress from Venus.

Alexandre Wetter femulating in the 2020 French film Miss.
You can view the trailer for the film on YouTube.

Someday Funnies

The other guys will know you mean business when you show up at the office in this skirt suit from Madeleine.

Wojciech Pokora femulated in this 1973 Polish film titled Poszukiwany, poszukiwana (Man-Woman Wanted). You can view trailers and an excerpt from the film here.

Reviewing Jessica

Glamour Boutique sent me a wig to try out and review: specifically an Estetica Designs synthetic wig called “Jessica” in light brown with golden blonde highlights (R12/26H). This is a shoulder length cut with soft spiral curls and straight bangs (approximately 4.5 inches front, 8 inches crown, 6.5 inches sides and 11 inches nape).

The wig’s cap size was average. I usually shy away from wigs with average size caps because my head is as voluptuous as the rest of me and average size caps have a bad habit of not staying put on my head. This was not the case with Jessica. Its cap size was a perfect fit for my head size and I did not have to use the wig’s adjustable straps to tighten the fit. After wearing Jessica for a few hours, I did not experience any wig headaches or other pain that sometimes occur with a new wig that has not been broken in yet. 

Jessica weighs in at 3,.7 ounces and its capless design makes it comfortable, lightweight and cool to wear. After wearing Jessica for a few hours, I did not experience any wig headaches or other pain that sometimes occur with a new wig that has not been broken in yet.

This style wig is a big departure from the shorter wigs I normally wear. I selected Jessica because I thought it was time for a change and I am very happy with my choice. It looks beautiful and I think it makes me look a little younger!

Just like this gender-fluid model, you too can rock this floral embroidered mesh dress from Boston Proper.

Enrique Herrera femulated in yet another film version of Charley’s Aunt. This one from Mexico in 1938 titled La tia de ls muchachas (The Girls Aunt). You can view the entire film on YouTube.

Boys and Gender Fluidity

Hollywood celebrities have become “way more experimental and accepting when it comes to parenting and letting children make their own choices” regarding the clothes they wear. The image above depicts just two examples, film stars Charlize Theron and Naomi Watts out and about with their sons. (Follow this link to read about other celebrities whose children are gender fluid in the way they dress.

Which reminds me of boys who femulate Disney princesses and boys who femulate mommies. 

I attended a public co-ed grammar school starting in kindergarten in the fall of 1956. My kindergarten class had two female teachers ― one middle-aged and one twenty-something.

For play time, the class of about 30 students was divided into five unisex groups. Each group took turns each day playing in different play areas: sandbox, toy blocks, art, play house, etc.

When it was my group's turn to play house, us boys played at being mommies, never daddies.

Some of the male mommies donned frilly aprons and “cooked” in the play kitchen, while other male mommies tended to the babies ― bottle-feeding Betsy Wetsy dolls and changing their diapers after they wet. When Betsy was dry, male mommies could push their babies around the classroom in doll carriages.

In addition to the frilly aprons, there was a toy box containing pocketbooks, high heels, lady’s hats and adult-sized dresses. There were not enough items to completely outfit each mommy, so we would select just an item or two for our femulations. (I usually tried to get a pocketbook and a pair of high heels.)

None of the male mommies rebelled at being feminized and some of us really got into it by affecting “female” characteristics, such as speaking in a higher pitch and using female mannerisms.

Initially, I felt embarrassed playing a mommy, but it did not seem to bother the other boys, so I played along like a girl with the rest of the boys. 

And so it goes.

Slip into this bodycon floral print velvet dress from Venus and you're set to steal the show from the other boys at this year’s Thanksgiving festivities.

Long-time Femulate reader and contributor, Aunty Marlena, invites you to visit her womanless photo collection on flickr. 

Third Time’s a Charm

Over the years, I went to work en femme on Halloween seven times. The first two times, my company invited us to wear costumes to celebrate the holiday and participate in costume contests. 

The third time, there was no invitation. I simply decided to show up at work in “office girl drag” and enjoy the day at work as a woman. And that third time was probably my best Halloween en femme at work experience because no one was expecting it and I fooled most of my co-workers with my femulation.

For example, when my boss arrived at work that day, I made a bee-line to her cubicle, saying “Happy Halloween” as I entered.

She looked up with a confused expression and it took about a half minute before she recognized me. She was ecstatic. She checked me out and gushed over my appearance.

“He shaved his legs.”

“He even did his nails.”

“I hate him – he looks better than me.”

She took my photo and e-mailed it to some of our colleagues in our other facility. And throughout the morning, she brought people to my cubicle to show me off.

I never saw her act like this before. She was enjoying my femulation as much as I was.

My boss also suggested I play a trick on our president’s administrative assistant, so when she showed up, I went into her office and said, “I am the new receptionist and you are supposed to train me.”

She was completely fooled. She said that no one had informed her of my training, but she was ready to have at it.

I felt a little sorry forever her, so before it went any farther, I asked, “Do you know who I am?”

She shook her head “no,” so I confessed and she was absolutely floored! She confessed that she really had no idea who I was nor that I was a male.

Returning to my cubicle, I heard the voice of a female co-worker who I had known for 16 years, so I paid her a visit.

“Happy Halloween,” I said as she looked up without any sign of recognition, then she recognized me. After she stopped gushing over me, she said that when she first saw me, she thought I was a former co-worker woman. She said the resemblance was striking.

At 10 AM, I had to attend a meeting (a “gemba”) concerning a new product. I walked into the middle of ten engineers standing in a circular fashion for the gemba, said “Happy Halloween” and they all smiled and took my appearance in stride. A couple of the guys admitted afterword that until they heard my voice, they had no idea who I was.

Another friend asked if he could take my photo sitting in his cubicle. I gladly agreed, he took it with his smart phoneand sent it to his wife claiming I was his new administrator.

After his wife learned the truth, she replied, “OMG!!!!!!! That is soooooo funny! He looks really good as a woman. I don't want her sitting in your cubicle.”

Five co-workers took my photo throughout the day and graciously e-mailed me copies. One co-worker said he was “speechless,” then added, “You missed your calling... you should have been a female impersonator.”

During lunch, I drove to the nearby Lowe’s home improvement store to get a replacement part for a piece of plumbing that failed after the storm the day before. I had no trepidation about going to Lowe’s and I found my trip very revealing.

Whenever I go to Lowe’s or Home Depot in male mode, I have to find and ask a store employee when I need help. Today, I had a male Lowe’s employee practically at my beck and call. When he saw me looking lost in the plumbing department, he asked what I needed and directed me to the exact location where the part was displayed. After I found what I needed, he came over and compared it to the old part I had brought along to make sure I got the right part.

That’s the power of a short skirt and high heels!   

Speaking of high heels, I wore them all day long (over 9 hours) and my feet felt fine. I guess sitting about two-thirds of the day helped. I did bring flats just in case, but I only put them on when I drove home.

I returned to work, ate lunch and felt tired; the 4:15 AM wakeup was beginning to take its toll.

I visited the two women in Human Resources who knew that I am transgender. The HR woman, who is approximately my age, was enthusiastic and said I looked “great,” while the 30-something HR woman acted as if nothing was unusual and said nothing about my appearance.

Another female co-worker I have known forever stopped by my cubicle in the afternoon and said I looked “sparkling.” She also commented that I looked better than she ever did even when she went to the prom. She wondered if anyone at work had busted “my chops” and I happily admitted that no one had.

Except for folks stopping by to look and/or take photos, the afternoon was quieter than the morning. Overall, I had a great day at work en femme. Not a discouraging word was heard; instead, I received a lot of compliments.

Next morning, my boss saw me and remarked, “Thank, God, you're dressed normal today.”

I responded, “What's normal?”

So, what’s your Halloween story? I’d love to read it and share it with my readers. And don’t forget to send along a photo or two from your holiday in heels.     

A very professional-looking ensemble from Venus for boys who work in an office.

.

Ms. Ross Erin and Mr. Patrick Holbert posing for their wedding invitation.
You can read all about it here.

Pants 10, Skirts 0

By Gina V

Back in the late 70’s, if myself and/or my chums ever had occasion to hear Billy Joel’s “It’s Still Rock and Roll to Me” on the radio, upon the hearing the line “a bright orange pair of pants” we could not suppress a schoolboy snigger. At the time “pants” was not another way to describe trousers for us Brits, but rather referred to what laid beneath. 

Not only was it acutely embarrassing for most to mention one’s unmentionables back then anyway, but the male vogue (for want of a better term) of that era was Y-fronts – which were somewhat unflattering to put it mildly!

It took a while for the word to enter our vernacular in the manner Americans used it. Probably (and not coincidentally) at a point where women were starting to wear trousers as often as they did skirts and dresses. And as such, the definition of “pants” implied they were a fashion option, as opposed to the traditional stuffy old things that men had no choice in wearing.

Even now in our “civilized” society, a man cannot wear a garment from the waist down that doesn’t have some form of division between the legs. Despite the efforts of French fashionista Jean Paul Gaultier and English football superstar David Beckham (among others) to offer an alternative that is actually better-suited to the male physique, resistance has remained rock solid. Even 20 years on, the latter is still ridiculed for once daring to wear a sari-style skirt in public!

It is the opposite case for women now in that their traditional garb of skirts and dresses have become (other than for more formal occasions) practically extinct. As a means of proving a point, while visiting the local supermarket at dusk on a mild autumn day, I decided to note what the first 10 women I saw go inside were wearing – with the above result. What were my thoughts on that? To use an appropriate contemporary British slang word for something that is considered rubbish: pants!

One of the fascinations for me as a crossdresser has always been to wear things that have been placed out of my reach simply because of the nature of my sexual organs. As a personal protest against being condemned as a man to wear trousers for life, I resolved that whenever possible, my femme alter ego would not pull on a pair of the damned things, And yet, many of my trans-sisters now seem more than happy to don them in preference to a skirt or dress in what I assume to be an attempt to femulate the woman of today.

I am aware that pants are more practical than even the most easily-worn skirts. But other than that or being some kind of women’s liberation statement, I still don’t understand why the latter are now shunned. In fact, where I live it has gotten to the point that if you happen to see a woman under pensionable age in a skirt while out and about, you can almost bet your bottom dollar it will be a member of the local Hassidic Jewish community!

What I find particularly concerning about all this is if I ever choose to live permane,ntly as a female in this day and age, then (other than changing my religion) unless I wore a pair of pants I would stick out like a sore thumb. And ironically be more at risk from unwanted scrutiny. 

If I ever did decide to bite the bullet in that regard, then I would rather they were in styles and fabrics that had a bit of flair and style about them and as such as those black skin-tight wet-look ones that have been fashionable the last couple of years. But then I would probably attract just as much attention than if I wore a skirt or dress. If not more so!

And just to add insult to injury: most if not all those women entering the supermarket had trainers or suchlike on their feet as well. Much like the aforementioned David Beckham’s Missus (see her quote on the right of the Femulate site), my view is that “flats” are for living in – not wearing! But that’s another story.

Wearing Nine West

Marie Sunshine, a Halloween femulator

(Cross) Dressing Your Age

Personally, I think that my legs are ok, but other people have convinced me that they are more so. My mother often said I had beautiful legs (and that “you should have been a girl with legs like yours”). My wife and other cisgender women have admitted that I have nicer legs than they do. 

I am tall, so my legs are long; maybe their length causes an optical illusion making them look better than they really are. I don't know, but I am not going to argue with success. If other people are happy with my legs, then I am happy with them, too.

So, I ask myself, “Since my legs are such a great asset, why not show them off?” I usually respond by wearing skirts and dresses with short hemlines (sometimes scandalously short hemlines) and high heels that are 2, 3 or 4 inches high.

When I add 4-inch heels to my 5-foot, 14-inch stature, I standout in a crowd topping out at an Amazonian 6 and 1/2 feet! So, when I am out in that crowd, some people may think I am an Amazon or I played for the WNBA; other people may think I am a man in drag.

One rule of thumb for passing is that you should crossdress your age, i.e., if you are an XX-year-old crossdresser, you should dress like an XX-year-old cisgender woman. At my age that means long skirts and lower heels or worse. By “worse” I am referring to the fact that these days cisgender women my age dress like cisgender men! Trousers, slacks and flats, not skirts, dresses and heels, is the norm especially among women my age.

I remember dining with four other T-girls in downtown Hartford. The place was full of 20- and 30-somethings, men and women alike. Do you know how many people I saw in the restaurant wearing a skirt or a dress? Two: one of the T-girls I was dining with and me! I did not see one cisgender woman in a skirt or dress.

To blend in that night, I should have worn slacks, not the short black skirt that I wore. And if I really wanted to pass that night, I should have worn flats instead of high-heeled boots, socks instead of pantyhose, a plaid shirt instead of an animal-print top, boxers instead of a panty girdle, a t-shirt instead of a bra. Also, I should have nixed the makeup and left my pocketbook, wig, and jewelry at home. Then, I would have passed easily, but as a man.

In my opinion, passing is overrated. If I have to make a choice between dressing to pass or dressing to thrill, I will choose dressing to thrill every time. Sometimes, I dress to pass, but that's no fun. For starters, when I dress to pass, I usually am not that happy with the clothing I wear. To make matters worse, when I dress to pass, I constantly worry about passing. I cannot enjoy myself out en femme. It is a real drag!

On the other hand, when I dress to thrill, I am very happy with the way I look and I can be myself because I do not worry about passing. What is interesting is that sometimes when I am dressed to thrill, I pass!

Here is one of my favorite passing-when-I-wasn't-trying stories.

Doing outreach at Southern Connecticut State University, I started the day in 3-1/2-inch stilettos, but just in case, I brought a pair of flats that I left in the car. After shopping at the mall before outreach and going to the first of two classes to do outreach, my 3-1/2-inch stilettos had to go, so I went to the car to fetch my more comfortable shoes.

As I walked through the parking lot, I saw a university dump truck parked right in front of the car. The driver was talking with another university employee standing next to the truck. Oh, damn, just what I needed, the classic transwoman nightmare, a Transwoman vs. Macho Guy Face-Off!

I was ready for the worst! Making a beeline for the car, I tried to ignore the guys, but the guy standing by the side of the truck greeted me with a very flirtatious, “Good afternoon,” while the guy in the truck smiled appreciatively and drove away.

They flirted with me! Wow – that was so unexpected!

So when I go out en femme, I am likely to dress to thrill and show off my legs rather than dress to pass. And if I do pass, then that is just an extra thrill.

Wearing Bebe

Eve, a lady in red

Someday Funnies

Wearing New York & Company

Scarlett, a femulating beauty in white

Ginger Takes on More

 Following up on “Ginger’s Take” in Tuesday’s post, I wrote to Ginger.

“Your response was revealing, but you really did not answer my question (or I worded it poorly), so let me try again. 

“What do gay guys think of girls like me? Do we amuse them? Do we disgust them? Do we impress them with out femulating skills? I ask because I found that gay guys at the few gay bars I have gone to don't seem too friendly. On the other hand, gay women seem to be more friendly.”

Ginger replied.

“Well, I'm probably not the best person to ask. I am a feminine gay man and feminine gays are a small minority in the population of gay men as a whole. Most gay men are masculine and are attracted to other masculine gay men. They don't ‘get it’ why or how gay men want to be feminine and/or why they are attracted to femininity. They don't understand why we don't transition into women. Because they don’t ‘get it’ (and because we are a small minority), they think we are freaks and resemble the homophobic image of what most gay men are like. They think we are the reason why the mainstream won’t accept and recognize gay men as part of the mainstream. We are attacked and beaten up by masculine gay men as we are by homophobic straight men. 

“Most crossdressers can’t pass, so if one goes to a gay bar they are not going to receive a warm reception. If you look like a guy wearing woman’s clothes, you (like feminine gay men) present a negative stereotype image. Most of mainstream society believes the majority of crossdressers are gay – and continue to believe it even after being informed that the vast majority are straight, married and have kids.

“There is an exception – drag queens and female impersonators are gay, but don’t crossdress when on dates with men. Crossdressing is their “job” not an expression of a need or desire to be feminine. 

“The lack of friendliness or even hostility you sense when you go into a gay bar isn’t your imagination – it’s real. Most don't like transgender people being part of the gay alphabet. ‘If a man completely transitions into becoming a woman and wants to date men, why then are they even aligned with homosexuals?’ they ask.”

Wearing Boston Proper

Australian femulator, Lena, in 1973 and 2011