My Halloween at Work En Femme

Every October, I thought about going to work crossdressed on Halloween. But thinking about it and actually doing it are two very different things.

Then one October, Human Resources announced that it would hold a costume contest on Halloween, with a major prize offered as an enticement. I didn’t need one. The opportunity to go to work en femme was enticement enough!

I already had everything necessary for an “office girl drag” costume. Actually, I had enough clothing for several office girl costumes, so all I had to do was decide which one to wear.

It never occurred to me to dress less than authentically so that the civilians wouldn’t become suspicious. On Halloween morning, I got up early and did my best to look like a genuine office girl. I wore a black-print, knee-length, short-sleeved sheath dress; tan pantyhose; a bra, waist cincher and panty girdle; black pointed-toe pumps with 3½-inch heels; an auburn wig; jewelry; full makeup; and a black handbag.

My wife looked me over, gave me a thumbs-up and sent me on my way.

When I arrived at work, I parked the car but hesitated before getting out. Finally, I put on my big-girl panties, stepped out of the car and entered the building.

Our receptionist and a woman from Human Resources greeted me in the lobby. Instead of buzzing old Stanley through the security door, the receptionist looked at me and asked, “May I help you?”

They didn’t recognize me until I revealed my identity. Then they began gushing over my costume!

I went upstairs to my cubicle. Because I had arrived early, few people were around to see me. One of my best friends at work was among the handful of employees who usually arrived before I did, so I went to her cubicle, stuck my head around the corner and said, “Trick or treat.”

She was floored!

After regaining her composure, she began calling me “Stella” and insisted on escorting me around to visit the other early birds. Our first stop was her boss, who had been with the company for about six months. I didn’t work directly with him, but his cubicle was only three spaces away from mine, and we crossed paths every day.

My friend pushed me into his cubicle, and he had no clue who I was. At first, he assumed I was a new female employee. Then my friend blew my cover.

“Don’t you recognize him?”

He didn’t—not until I explained that I was the guy who worked three cubicles away.

And that was the way it went all day.

In an office filled with Halloween costumes, my height was a clue. Most people read me as a man in drag, but they couldn’t figure out which man until I showed them the photograph on my security card. On the other hand, a surprising number of people didn’t read me at all—including some with whom I worked regularly.

By midmorning, word had spread that there was a guy in drag upstairs, and a procession of onlookers began marching to my cubicle to check me out. No other men appeared in drag. In fact, only a handful of men wore costumes of any kind. The women had much more Halloween spirit, with approximately 25 of them arriving in costume.

In general, the women loved my outfit. Some were amazed that I had shaved my legs and arms. Others complimented my makeup, and several asked, “Did your wife do your makeup?”

“No, I did it myself,” I replied, which caused even more amazement.

A few people suggested that I quit my job and become a professional female impersonator. One woman said I had made her day, then returned to my cubicle three times, bringing two or three new onlookers with her on each visit.

A pretty administrator remarked, “You look better than most women I know.”

That made my day!

A few women gave me knowing looks, as though they suspected I looked too good for this to be my first time. But I didn’t care.

Shortly after arriving at work, my pantyhose began running like crazy. I don’t know whether they were defective or I had been careless, but by 10 o’clock, I had three runs that were growing larger by the minute. I wanted to look my best, so I slipped out of the building and drove to a nearby CVS to buy another pair.

This was where the day became even more interesting.

I parked the car and walked into the store, passing several people who paid no attention to me. To avoid causing a commotion, I approached the first saleswoman I saw and explained that I had gotten a run in the pantyhose I was wearing with my Halloween costume and needed a replacement pair.

“Hosiery is in aisle eight, Ma’am,” she replied, apparently unfazed by my mention of a costume.

Evidently, I wasn’t going to cause a commotion.

I went to aisle eight, selected a pair—only $1.99—and returned to the register. The same saleswoman rang up my purchase without displaying the slightest suspicion.

Here is the remarkable part: I never used a feminine voice. I spoke in my normal voice, which is admittedly soft-spoken but definitely male. Apparently, the saleswoman’s eyes convinced her that I was a woman, regardless of what clues her ears might have been receiving.

I returned to the office, changed my pantyhose and waited for the results of the costume contest. Many people had told me they planned to vote for me, and I guess they did because I won.

I thought three or four costumes were better than mine, but perhaps having the nerve to wear what I wore provided the little something extra that pushed me over the top.

I had the time of my life. I wished the day would never end, but of course it did.

What remained were many wonderful memories of my first day at work en femme—and the knowledge that thinking about doing it had finally become actually doing it.

Wearing Boston Proper

Gary Busey femulating in the 1998 film Rough Draft.

No Party? No Problem!

Stana at Websterbank on Halloween

Halloween is often recommended as the perfect occasion for making your first public appearance en femme. Costume parties provide a convenient excuse to dress, and if anyone recognizes you, you can always claim that you are simply getting into the spirit of the holiday.

But what if you have no party to attend?

Who says you need one?

Instead of sitting home waiting for an invitation that may never arrive, put on your favorite outfit, apply your makeup, grab your handbag and go out among the civilians. Halloween itself is the event and the whole world is the party.

You do not have to wear a costume. In fact, I suggest dressing as the woman you want to be rather than as a comic exaggeration of one. Wear something attractive and appropriate for wherever you plan to go. You can visit a shopping mall, browse a department store, stop for coffee, enjoy dinner at a restaurant or take in a movie. Even a simple trip to the pharmacy can become a memorable adventure when it is your first time out en femme.

Halloween provides a little extra protection for the nervous beginner. People are accustomed to seeing unusual clothing, elaborate makeup and unexpected characters. If someone reads you, they will probably assume that your feminine presentation is your Halloween costume—and then continue with whatever they were doing.

Meanwhile, you get to experience something much more meaningful than attending a costume party. You get to walk through the real world as a woman.

At a party, everyone may stare because costumes are the evening’s entertainment. Out among the civilians, most people are too busy shopping, eating, talking or looking at their phones to pay much attention to you. You may discover that the frightening reactions you imagined never happen. The sales associate may call you “Ma’am.” Someone may hold a door for you. Another woman may compliment your dress, shoes or handbag.

You might even forget that you are supposed to be nervous.

If this is your first outing, make it easy on yourself. Choose a familiar, well-lit place where other people will be around. Go during daylight or early evening, know where you will park and avoid areas that become rowdy later at night. If possible, invite a supportive friend to accompany you. Most importantly, dress appropriately for your destination and behave as though you belong there because you do.

You need not spend the entire evening out. Promise yourself that you will walk through one store or order one cup of coffee. Once you have accomplished that, you can go home feeling victorious. Of course, you may feel so comfortable that one stop becomes two, and two stops become an entire evening.

Halloween may give you the excuse to open the door, but you must be the one willing to walk through it.

So, if no invitation arrives this Halloween, do not be disappointed. Create your own celebration. Get dressed, go out and mingle with the civilians.

The best Halloween party may be the one happening everywhere.

Wearing Cynthia Rowley

Michel Serrault en femme in the French film La Cage aux Folles.

Halloween En Femme: The Good and the Bad

For many crossdressers, Halloween is the unofficial national holiday of crossdressing. It is the one day of the year when a man can wear a dress, heels, makeup and a wig in public without offering much of an explanation.

That makes a Halloween party an inviting place for a first public appearance en femme. However, Halloween has both advantages and disadvantages for the would-be femulator.

The Good

The greatest advantage is the ready-made excuse. If someone asks why you are dressed as a woman, the answer is obvious: “It’s Halloween.”

That excuse can provide enough courage to get a closeted crossdresser out the door for the first time. You can walk into a party wearing the outfit you have dreamed about wearing in public while telling yourself (and everyone else) that it is only a costume.

Halloween parties are also usually relaxed occasions. People expect unusual clothing, exaggerated makeup and characters who do not look the way they normally look. If your wig slips, your voice falters or you walk awkwardly in your heels, nobody is likely to care. Imperfection is part of the fun.

You may also discover that people react much more positively than you expected. Women may compliment your dress, makeup or legs. They may ask where you bought your shoes or offer to adjust your hair. Men may hold doors, offer you a seat or treat you differently simply because of the way you are presenting yourself.

For someone making a first appearance en femme, those little moments can be thrilling and educational. They may demonstrate that the fears keeping you in the closet were greater than the actual risks outside it.

Halloween also offers an opportunity to test your presentation. You can learn whether your shoes remain comfortable after several hours, whether your makeup survives a warm and crowded room and whether your outfit allows you to sit, walk and socialize gracefully.

Best of all, Halloween may provide your first taste of being accepted as a woman in a public setting. That experience can supply the confidence needed to venture out again when there is no Halloween costume to hide behind.

The Bad

The same costume excuse that makes Halloween comfortable can also work against you.

If you make too much of an effort, friends may wonder how you became so skilled at applying makeup, walking in heels and putting together a coordinated outfit. A borrowed dress, crooked wig and hairy legs suggest a joke. A perfectly fitted dress, polished nails, pierced ears and practiced feminine mannerisms may suggest that this is not your first rodeo.

You may receive questions such as, “Where did you learn to do your makeup?” or “How did you know your dress size?” Be prepared with answers or be prepared to smile mysteriously.

Another disadvantage is that some people assume a man dressed as a woman must be performing comedy. They may expect exaggerated gestures, a falsetto voice or behavior copied from a bad drag routine. If your goal is to present as an ordinary woman, being treated as the evening’s joke can be disappointing.

Alcohol can make matters worse. Someone who begins the evening with harmless teasing may become louder, more intrusive or less respectful after several drinks. A party guest may touch your wig, tug at your clothing or ask personal questions that would never be asked of a woman.

Photographs are another consideration. At a Halloween party, everyone has a phone, and party pictures can quickly appear online. Before attending, decide whether you are comfortable being photographed en femme and whether those pictures might be seen by relatives, neighbors or coworkers who do not know about your crossdressing.

There is also the temptation to overdo everything. Because it is Halloween, a crossdresser may choose the shortest skirt, highest heels, largest breasts and heaviest makeup available. That can be fun if an outrageous costume is the objective, but it does not teach much about presenting as a woman in everyday life.

Finally, the end of the evening can be bittersweet. After several happy hours en femme, removing the makeup and returning to male clothing may feel more difficult than expected. Halloween can open a door that you may not be eager to close again.

Making It a Treat

If you plan to attend a Halloween party en femme, decide beforehand what you want from the experience. Do you want to create an amusing costume, make a glamorous entrance or find out how it feels to socialize as a woman?

Dress for that goal, but also dress appropriately for the party. Wear shoes you can walk in, clothing you can sit in and makeup that will last. Arrange safe transportation, limit your alcohol and think twice before consenting to photographs.

Most importantly, enjoy yourself.

Halloween offers something rare: permission to try a different presentation without making a public declaration about who you are. For many crossdressers, it is the first step from the safety of the closet into the civilian population.

The Halloween excuse may get you through the door, but the confidence you gain can remain long after the jack-o’-lanterns have disappeared.

And if everyone tells you that you make a very convincing woman, just smile and say, “Beginner’s luck.”

Wearing Ann Taylor

Nick Kroll

Stuff 135: Thrifting

By JJ Atwell

Inexpensive Shopping

Have you ever gone thrift-store shopping for your girl self? I see two big attractions: the thrill of the hunt and the huge potential savings.

I was recently introduced to thrifting by the wife of a good CD friend, and I’m hooked! As an aside, this is one of the unexpected benefits of belonging to a local crossdressing group: you get to learn from others—not just other CDs, but their partners, too.

Thrill of the Hunt

When I was little, I used to accompany my dad on our weekly runs to the dump. This was long before sanitary landfills and transfer stations. Dumps were where people brought trash and things they no longer needed or wanted. It wasn’t uncommon for us to come home with something someone else had discarded but that we decided we could use. Remember the saying, “One man’s trash is another man’s treasure”? We found treasures.

At a thrift store, you’re searching for a crossdresser’s treasure, but the hunt can be a little messy. You may be confronted by row after row of clothing arranged roughly by type and size—and every item is one of a kind. Where do you start?

At Goodwill, first look for the sign identifying the current sale color. Items with tags of that color are half off the marked price, making them a double bargain.

If you enter the store looking for a particular type of garment, you can head straight for that section. For example, perhaps you want a pair of casual, wide-leg pants, which is what JJ was seeking on a recent visit. Just go to the women’s pants section and search through the size you need. Then scan the racks to see whether any colors or patterns catch your eye. I managed to find four pairs of wide-leg pants that fit perfectly.

Found something? Great! But wait—is it the right size? Does it have any imperfections, such as excessive wear, stains or other marks? Examine it carefully before placing it in your cart.

Speaking of size, your local thrift store may not have a dressing room. If it doesn’t, you’ll need to be good at judging how something will fit just by looking at it. Try holding the garment against yourself to see whether the length is right and the waist looks as though it will fit.

Savings

While you’re there, be sure to look at items that may not be on your shopping list. You might be surprised by what you find. Perhaps you weren’t specifically looking for a prom dress—but what if that prom dress costs only $10? Or how about a sequined top with a matching scarf for $7?

You’ll probably leave the store with things you never expected to buy when you walked in. Prices are excellent, and you can find some wonderful pieces that coordinate with clothes already in your wardrobe. A recent thrift-store excursion added eleven items to JJ’s closet for only $80. Even if a few of them don’t quite work out, that’s still a bargain.

Bonus

Thrift shopping offers another bonus: you get to observe lots of bargain-hunting women—and possibly other CDs—in their native habitat. Between that experience and the savings, it’s a BOGO!

On one thrifting excursion, I visited three different shops with two other members of my local group and their significant others. While browsing, it occurred to me that our situation might be unusual: there we were, three crossdressers in the same store.

Then another thought occurred to me: were there only three?

Yes, there were three of us for sure—but how many other CDs were shopping there at the same time? I feel fairly certain that we crossed paths with at least one. I’m equally certain that we weren’t the only CDs ever to visit a thrift store.

I’ll Be Back

I’ll be back with more Stuff in the next installment. Comments are welcome either here on the blog or by email at Jenn6nov at-sign gmail dot com. JJ is always looking for more Stuff, so let me know what you would like to read about.

Wearing Shein

Lena from Australia

I have no words

“You’re a guy!”

Most civilians are too busy with their own lives to pay much attention to us. Occasionally, however, someone will recognize that the attractive woman passing by was not assigned female at birth—and decide to announce the discovery.

“You’re a man!”

“Is that a guy?”

“Why are you dressed like a woman?”

Being called out can be startling, embarrassing and even frightening, especially the first time it happens. Your immediate reaction may be to panic, argue or flee. Usually, the best response is much simpler: remain calm, assess the situation and refuse to let a stranger ruin your day.

Consider the Source

Not every comment is intended to be cruel. Some people are genuinely curious, surprised or socially clumsy. Others are showing off for their friends or trying to provoke a reaction.

Before responding, consider the tone, the surroundings and the number of people involved. One puzzled shopper in a department store is very different from a loud group outside a bar at midnight.

If the situation feels threatening, forget about clever responses. Move toward a well-lit, populated place, enter a business, contact security or call for help. Your safety is more important than proving a point.

Do Not Provide the Entertainment

A heckler usually wants a reaction. Becoming angry or visibly upset gives that person exactly what was wanted. Instead, take a breath, stand tall and continue behaving like the lady you presented to the world that morning.

A calm “Yes—and?” can bring the confrontation to an abrupt end. So can “Thank you for noticing,” “I’m happy with how I look” or a pleasant smile followed by walking away.

Silence is also a response. You are not required to explain yourself to every stranger who asks a personal question.

Own the Moment

There is no shame in being a crossdresser. If someone announces that you are wearing women’s clothing, that person has merely stated the obvious. You already knew what you put on before leaving home.

A confident response changes the balance of the encounter. Instead of acting as though you have been caught doing something wrong, behave as though the other person has made an unnecessarily rude observation.

Depending on the circumstances, you might say:

• These are my clothes.

• I dress to please myself.

• You noticed. Is there anything else?

• I didn’t realize there would be a quiz.

• My wife likes this outfit, too.

• And you felt the need to announce that because…?

Humor can defuse an awkward encounter, but sarcasm may provoke someone who is already hostile. Read the room before delivering your best comeback.

Do Not Turn It Into a Debate

A public sidewalk, restaurant or shopping mall is rarely the place to conduct a seminar on crossdressing. You will probably not change a hostile stranger’s opinion during a two-minute confrontation.

Answer briefly if you wish, then move on. You have places to go, things to do and perhaps a sale rack waiting for you. Do not surrender the rest of your outing to someone who deserves only a few seconds of your attention.

Recover and Continue

Even when you handle the encounter perfectly, being called out may shake your confidence. Step into a restroom, café or quiet corner and give yourself a moment to regroup. Check your makeup, smooth your skirt, take a few deep breaths and remind yourself that one person’s reaction does not represent everybody.

Then continue your outing if you feel safe doing so.

Going directly home may teach your frightened mind that the stranger defeated you. Staying out—even for another fifteen minutes—can help you reclaim the experience and prove that you remain in control.

Confidence Is the Best Response

Passing perfectly is never guaranteed. Even cisgender women are occasionally mistaken for men, and civilians make all kinds of incorrect assumptions about the people around them.

The real goal is not to fool every person you encounter. It is to present yourself well, behave naturally and enjoy being the person you chose to be that day.

If someone calls you out, keep your composure, protect your safety and remember that you have as much right to occupy public space as anyone else.

Hold your head high, adjust your handbag and keep walking. The heels clicking on the pavement should be yours—not those of a crossdresser retreating in defeat.

Wearing ModCloth

Brian Charles Rooney femulating on stage in Bedbugs!!!

Why Wives Encourage Husbands to Crossdress

When people discover that a wife encourages her husband to crossdress, they often assume there must be some strange explanation. In reality, her reasons may be quite ordinary: love, curiosity, companionship—and perhaps the pleasure of seeing her husband in a pencil skirt and heels.

Every wife is different, of course, but here are a few reasons she might encourage her husband to explore his feminine side.

She Knows It Makes Him Happy

This may be the simplest explanation. She understands that crossdressing is important to him and sees how much happier, calmer, and more confident he becomes when he is dressed.

A loving spouse usually wants her partner to be happy. If slipping into a dress puts a smile on his face and does no harm, she may see no reason to discourage it. She might even help him make time for it.

She Appreciates His Honesty

A husband who shares his crossdressing with his wife is trusting her with a very personal part of himself. Once she gets past the initial surprise, she may appreciate that honesty.

Encouraging him can be her way of saying, “You don’t have to hide this from me.”

That acceptance can strengthen a marriage. Instead of crossdressing becoming a secret that separates them, it becomes something they can discuss openly and negotiate together.

She Enjoys His Feminine Side

Some wives discover that their husbands are more relaxed, affectionate, communicative, or attentive when dressed. His feminine presentation may allow qualities that are normally hidden beneath masculine expectations to come forward.

She may enjoy spending time with this softer version of her husband. He is still the same person, but perhaps he is more willing to talk about feelings, notice fashion, accompany her shopping, or understand how long it takes to get ready.

She Likes How He Looks

Let us not overlook the obvious: she may think he looks good.

Perhaps he has beautiful legs, a slender figure, or a natural sense of style. With the right dress, wig, makeup, and heels, he may be surprisingly attractive. His wife might take pride in helping him improve his appearance—and enjoy the reactions when they go out together.

Some women simply like pretty men.

It Gives Them Something to Share

Crossdressing can become a shared interest. They can shop together, exchange fashion advice, experiment with makeup, visit salons, or plan special outings.

A wife who once shopped alone may suddenly have an enthusiastic companion. Unlike many husbands, he may understand why one needs several pairs of black pumps or why a handbag should coordinate with an outfit rather than merely carry things.

For some couples, getting dressed together becomes part of the fun.

She Enjoys Being His Stylist

A wife may see possibilities in her husband that he cannot yet see himself. She knows which colors flatter him, which skirt suits his figure, and which hairstyle softens his face.

Helping him develop his feminine image can become a creative project. She may enjoy teaching him about clothing, makeup, jewelry, posture, and presentation. Before long, she may be selecting outfits that are more adventurous than anything he would have chosen for himself.

He thought he was merely buying a blouse. She was planning a complete makeover.

She Is Curious

A wife may simply wonder how far the transformation can go. What would he look like with professionally applied makeup? Could he walk gracefully in heels? Would strangers recognize him? Could the two of them go shopping or have dinner together as girlfriends?

Curiosity can turn reluctant tolerance into enthusiastic participation—especially when the results exceed expectations.

It Can Bring Them Closer

Sharing something unconventional requires trust, patience, and communication. Couples who discuss crossdressing honestly may learn more about each other’s fears, desires, and boundaries.

That does not mean the wife must approve of everything or participate every time. Encouragement works best when both partners remain comfortable and neither feels pressured. He should not expect unlimited acceptance, and she should not push him farther than he wishes to go.

Crossdressing should be something they explore together, not something either spouse uses to control the other.

She Loves the Whole Person

Ultimately, a wife may encourage her husband because she understands that his feminine side is not a rival competing for her affection. It is one part of the person she married.

She may not have expected to share her closet, makeup mirror, or favorite shoe store with her husband. Nevertheless, life occasionally presents unexpected additions to the marriage.

Sometimes that addition is wearing a skirt, carrying a handbag, and asking, “Do these heels work with this dress?”

And sometimes his wife smiles and replies, “They will after we find you the right earrings.”

Wearing Boston Proper

Femulating in the Wolf Alice music video for Moaning Lisa Smile.
Click here to view this video on YouTube.

Stuff 134: Caught

By JJ Atwell

Uh-Oh!

A fellow Femulate reader, Tia, wrote to suggest that some crossdressers secretly want to get caught. I had never considered that before. It seems to me that most of us go to great lengths to avoid getting caught. But the more I thought about her proposition, the more it seemed like a good subject for Stuff.

Please understand that I have never tried to get caught, so these are simply my musings.

Forcing “The Talk”

I wonder whether those who secretly want to get caught see it as a way to finally broach the subject with their friends or perhaps their significant other. If you are in the closet but wish you could talk about your crossdressing with someone, finding the right time to bring it up can certainly be difficult. Maybe some people need that extra push to start the conversation.

I’m not sure getting caught is a good way to introduce the subject, though. It seems to me that you would be starting off on the wrong foot—or stiletto.

My advice, for whatever it’s worth, is not to use this method to initiate “the talk.” Instead, find a quiet time when it’s just the two of you and begin a general conversation to get the words flowing.

During that conversation, perhaps mention that you have always found society’s gender roles interesting. Tell her that you admire the way she dresses and that you appreciate her femininity. Be careful not to make her feel that she is not “woman enough.” That may provide a springboard into the subject of crossdressing and why it interests you.

Or it may not. It really depends on the dynamics of your relationship. No, there are no easy answers here.

Loving Danger

Perhaps the desire to get caught is motivated by pure adrenaline—the same thing that makes roller coasters so thrilling. Some people thrive on that kind of excitement. Could the risk of being discovered provide a similar jolt?

Since I’m not that kind of thrill-seeker, I’m probably not the right person to comment further. But I would love to hear from readers who see it that way. You can leave a comment or email me using the contact information below.

Being “Forced”?

I also wondered whether some people want to “suffer the consequences” of getting caught. Perhaps those consequences might include being forced to remain dressed—or being told to wear something even more feminine.

By being “forced” to dress, they can sidestep the guilt that many crossdressers experience. They can rationalize that someone else is making them do it. That way, they are simply being good partners by complying with another person’s wishes.

These are merely possibilities that occurred to me as I contemplated the subject. I really don’t know the answers, but perhaps you have some thoughts to share.

I’ll Be Back

No, that’s not me getting caught in the picture at the top of the page. I had “the talk” with my wife long before we were married. The image was created by ChatGPT using a simple prompt.

As always, comments are welcome either here on the blog or by email at Jenn6nov at-sign gmail dot com.

JJ is always looking for more Stuff, so if there is something you would like to read about, please let me know!

Wearing Ann Taylor

Womanless beauty pageant contestant in Camdenton, Missouri, circa 1967