I’ve written one other article on this site but posted on several forums. Many of you know that I go to work En femme on a fairly regular basis. I teach in a very open department and so coming into the office in a skirt and heels hardly causes a stir. People asked a few questions, were accepting, and things went back to normal. I’m so blessed with the opportunity to experiment in a place where people are accepting and kind. I know not everyone here has that, and I try not to take it for granted.

This semester, I’ve been assigned a course called “Critical Analysis of Social Diversity.” I’ve previously taught this course in different formats, but never in anything other than my “normal” male wardrobe. I’ve thought and dreamed about teaching as Sarah frequently, maybe in a lesson about gender, for example, but it never seemed like the right time. For whatever reason, I decided that this would be that time. This semester, Fall 2023, I decided to dress up for my students.

I planned to do this at the beginning of the semester for a couple of reasons. Probably the biggest motivation was that I knew that once I “broke the ice” so to speak, I’d feel freer to dress up for class whenever I wanted to for the rest of the term. Beyond that, I thought it would make an excellent object lesson. I’d considered using photos but felt like it would be disingenuous to use images of others. It would be more effective and honest if students saw me taking risks like this, rather than posting an image of someone else and discussing them as if we were examining a bug under a microscope. I wanted this to be authentic, and I wanted students to know that anything I spoke afterwards came from a place of personal understanding and investment. I hoped it would make it real and make them better able to listen to everything that came later.

As you might imagine, the weeks leading up to that fateful lecture were filled with a variety of thoughts. How would the students respond? Would they hate me? Feel creeped out? Maybe they would be angry. Is this right or wrong? My university services a fairly rural, conservative population and you never know what students will come to class with. It isn’t that I’m worried about what they think of me as much, but what kept me from dressing up in the past was my fear that some students might be shut down or pushed away. Often, the students I want to reach the most are the most sensitive to breaking certain boundaries. You need to meet people where they are if you want to share anything meaningful, let alone challenging. Crossing gender boundaries is NOT where many in my community are at.

Visit Transgender Heaven

One of the fun, but vexing, parts of this experience was trying to decide what outfit to wear. I finally settled on a light blue button-up professional blouse, a high-waisted gray pencil skirt, and a pair of beige high heels. I wore shapewear to create some nice curves and donned my normal brunette wig. I saw this as classy, professional, and it’s also one of my favorite outfits. Business styles nearly always work well for me. I will add that this was only the second day of class, so the students had only seen me once, so most of them didn’t know me very well. A couple of them had taken other classes with me, but only ever saw me in drab.

As often happens when preparing for an outing En femme, the buildup to the moment you walk out the door is worse than the event itself. But by the time I was ready to go, I was excited and looking forward to the day. I drove to work, went to my office, and began preparing for my lecture. When the time came to leave my office, my excitement had all but conquered my fear. The nerves I felt were good nerves. Scary, but fun, too. I had to walk about 400 yards across campus, to the building where the classroom was, which added to the fun and also allowed me the pleasure of hearing my heels clicking on the sidewalk.

Dressing up that day centered on an activity I designed to give the students a direct experience with their own responses to diversity and deviance (for clarity, deviance within sociology doesn’t mean criminal, just unusual). At the beginning of class, I passed out 3×5 inch note cards. At the top of one side of the card their instructions were to write, “My thoughts” followed by 1, 2, 3, 4, 5. I asked them to write the very first thing that came into their minds when they saw their male professor dressed like a woman. After that, they were told to flip the card over and write, “Other’s thoughts” and make the same numbered list with how they think others might have thought or responded.

I gave the students about 10–15 minutes to do this and then collected their cards. I told them I would compile their responses and that would form the basis for our discussion on Friday. They were told not to put their names on the cards because I wanted them to feel comfortable being as honest as possible with their responses.

Crossdresser Superstore

I received 39 cards back out of 44 students; (I don’t know if the others didn’t participate or if they were absent). Only one of them said they felt uncomfortable and didn’t like the situation. Generally, the responses were overwhelmingly positive. Lots of students said I looked great. Many of them said I really “slayed” it that day. LOL. I had to ask the grad student I share office space with what “slay” meant. Apparently, it’s really good. Many said that I looked better in the outfit than they would have, and I got some nice comments on my calves. Apparently, I looked so good that many students wondered at first if I was a new teacher or a sub, or if they were in the wrong class. One student emailed me later and wondered if I had taught that day. He said he looked through the classroom window and didn’t see me lecturing, so he thought something had changed.

After the students handed their cards back in, I gave them the chance to ask questions about me and my outfit. They asked the usual things you might expect. How do people respond? When did you start dressing up? Are you trans? What pronouns should we use? I told a funny story about a couple who was probably trying to steal my phone but seemed to like my dress. Lots of people said on their cards they were confused about whether or not my hair was real; (it’s the wig you’ll see in all my pictures) and so people asked about that, too. The first thing anyone asked was where I found heels in my size. After giving the students a chance to satisfy their curiosity, I shifted into a regular lecture about the nature of society and culture that would help set the stage for future discussions. I took my heels off, afraid that walking back and forth and writing on the board in 5-inch spikes might lead to a broken ankle and an unflattering fall. So, this was also the first time I ever lectured barefoot. I’m glad it was a carpeted classroom. To me, there’s something really sexy about a well-dressed woman taking her heels off for a break or to walk across a lawn. I don’t know how my students felt, but it definitely added to the fun for me.

After class, a couple of students came up to me to ask questions about the class website and other usual, completely normal student things. I then hurried back across campus to our department building where I sat through a really boring meeting with my colleagues. After finishing up the day I went home and did my normal routine. 

The next day I compiled the results and then prepared a lecture based on those experiences and exploring the way that we respond to difference. That lecture went well too. We’ll see how the rest of the semester goes, and how they respond to future outfits, but for now, I count it a win.


More Articles by Sarah Kanter

View all articles by Sarah Kanter
The following two tabs change content below.

Sarah Kanter

I’m Sarah, and I’m a newbie. I’ve tried things on sporadically (and secretly) over the years, but only last year decided to jump into dressing up “for real.” I finally bought some clothing of my own and a wig and ventured out for a walk around the campus where I work at night. I don’t have to tell you all how much fun it was. Soon after, I was going regularly to the office (in the evening) and grocery shopping en femme. For those of you worried about going out for the first time, if you dress up with a little bit of class, no one seems to care. It’s almost disappointing how little people actually notice. I’m an endurance athlete though, so I pass pretty well as a tall, strong woman. My spouse is great, but not a fan. We talked about my desire to dress as soon as we were married, but she wasn’t keen on the idea. My first real outing came while she was travelling for a few weeks, and I talked openly about it with her when she came back. I don’t think you should ever hide things from your spouse. She wasn’t thrilled about it, so I told her I’d keep it to myself. A bit more about me: I’m 38 years old and I’ve always been interested in women’s clothing. As a little kid at the pool I thought one piece swimming suits looked way more fun than baggy shorts and I’ve always liked dresses. While dresses and swimsuits are my favorite I look best in skirts and blouses. I am definitely not transgender. I like being a guy and I view dressing up as just another interest among many. It’s certainly different than skiing or fishing or my love of old 4×4’s, but it isn’t any more important to my identity. I think I like cross dressing because I like women. Women are beautiful and it’s fun to look pretty (my artistic side comes into play here). The deviance also makes it fun. I think if it was normal for guys to wear evening gowns, I wouldn’t be that interested in them. There’s an element of disguise that’s intriguing too. Like when a super hero in a comic book puts on their mask, something special happens. Knowing you have this other, secret side adds something. All the best,

Latest posts by Sarah Kanter (see all)

5 3 votes
Article Rating
Inline Feedbacks
View all comments
DeeAnn Hopings
6 months ago

The employer from which I retired had a policy related to dressing. If one was in the process of transitioning, it was perfectly fine to dress as your target gender. However, what wasn’t OK was to go back and forth between modes. Basically it was a one way trip.

DeeAnn Hopings
6 months ago
Reply to  Sarah Kanter

My guess would be that in a business setting it would be confusing. It amounts to “Who are you today? How should I address you?”. I suspect that many would find it confusing. It might also draw backlash from conservatives. No, make that probably.

Venus Envy
6 months ago

Look for Ciera Cremins, I think it’s spelled, in New Zealand. Crossdressing full time and teaches in much the same area as you. And the emotions of coming to work and class as a woman are, not surprisingly, very similar to yours. She has published at least 2 books. I have read “Man Made Woman". She addresses gender roles not only as artificial, but also a result of capitalism and the patriarchy. It’s a very coherent and congruent thesis. There are several book tour interviews available on line. I’ve felt the rigid expectations of the patriarchy all my life, and… Read more »

Bianca Everdene
Trusted Member
6 months ago

Thank you so much for sharing your experience Sarah. So happy it went well for you, and you can now express this wonderful side of yourself more freely. Another positive story to reinforce our community’s journey to fully integrate into society. I wish I could emulate your story. Unfortunately in nursing I work overwhelmingly with elderly patients from previous generations with outdated views on gender norms and stereotypes. Plus gotta wear scrubs, minimal make up, no jewellery except stud earrings, a wig would be a no no, and can you imagine me clicking down the ward in heels! A profession… Read more »

Alice Black
Active Member
6 months ago

I like your article, Sarah. You are very brave. I work a telecommute job and I do not even have the nerve to cross dress in that setting. The camera supposedly is always off unless I turn it on at meetings. But I always wonder if camera can be on and somebody is watching me from there. Maybe I am paranoid. Just want to keep working – need the $ even though I am past retirement age. Also, I am old fashioned and have always felt I had dress professionally at work. I would wear a shirt and tie to… Read more »

Rochelle Mills
Active Member
6 months ago

Sarah. thank you for sharing your engaging, slice of life story. I always love reading examples of CDs/trans who explore their inner women in public or at work. Breaking through the initial trepidation opens the doors to fantastic experiences, conversations, and friendships. Also love your writing style–have a wonderful semester!

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?