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I Went Swing Dancing In A Skirt

April 4, 2014


While I was on a trip, I did a bit of crossdressing. Before I started my trip, I went to work for a few hours. Mid-day, I went to the airport. On the first leg of my flight, I flew in the men’s clothes I went to work in. At the first layover, I changed into rather androgynous women’s clothes. I wore a white T-shirt, a white collared shirt partially buttoned, black ladies slacks with somewhat flared legs, nude pantyhose, and white Keds. The pants were long enough that they went to my shoes, so my ankles were not showing. In fact, my ankles barely showed when I sat down. If I could get up the nerve, I planned on putting on a skirt when I got to my gate.

When I changed into the outfit I just described, I was in the men’s room. The attendant working the men’s room came my way as I came out of the stall. He gave me some towels and wiped the counter. He looked down at my white shoes under black pants and then pushed out his lip. He asked if I was wearing part of a business suit. I said no. He said I looked sharp. He liked the white shoes with the black pants. His comment was positive, but he was my first person to encounter and he immediately noticed my outfit. Not a good sign! After that, almost no one else ever paid my outfit any attention. His attention left me slightly uneasy. Being uneasy at the start of a crossdressing outing is rather common for me.

I never got up the nerve to change into my skirt at the gate. The last time I flew to that destination airport, I came upon someone I knew pretty well at the luggage carousel. That has made me wary of flying into that airport en femme.

At my destination, I walked to the bus stop to wait for the shuttle bus to the rental car facility. A man who was also waiting watched me walk by. He gave me a look up and down. He did not seem threatening, but he did not seem to approve. He noticed. On the shuttle bus, I realized I was sitting near him in plain site. He paid me no attention on the shuttle bus.

When I got to the rental car facility, I completed my processing for the car. Then I went to the restroom and put on my skirt. There were not many people on that side of the facility and no one was in the restroom. I was not too nervous. I walked out into the garage and the attendant talked to me through the window. Then he walked out to help me. He talked with me a long time. I do not think he noticed what I was wearing until he separated from me. My confidence mounted.

I got in my car, drove to the hotel, and checked in while wearing a skirt. “Disapproving man” from the shuttle bus was at the counter too. He was staying in my hotel. I kept my bags between us so he could not see me. I do not think the hotel clerks saw my outfit before I approached the counter. They had been looking down.

I went into the hotel store. The attendant was a young international man. He took his quick glance down when I walked in. After that, he only looked me in the eye when I was talking to him. He had time to look at me while I was getting some laundry soap and seeing what else they had. He talked to me quite a bit when I came over to pay.

I changed into a deep red top, a black button up jacket/shirt, a multi-colored, knee length skirt, black hose, black heels. I went down to the hotel lobby for supper. Some people saw me, but I saw no sign of them telling the people at their table to look at me. It seems that I am not much of a spectacle here. I was seated on an empty side of the restaurant. No one could see me. The waitress served me and chatted with me normally.

I left there and went ballroom dancing in the city. I got out of my car, and started walking down the sidewalk. A man was walking toward me. He came to a complete stop and would not approach me. I was still walking toward him. I turned to cross the street. He kept looking at me like I was dangerous. I greeted him, “Good Evening”, and crossed the street. As I approached the ballroom entrance, a man who was standing outside smoking greeted me and welcomed me.

Inside, I found that most of the attendees were young. Many of the people I danced with were visiting the place for the first time. There was a long lesson where the girls rotated around the circle of men. Every girl treated me with politeness and respect. No one refused to dance with me during the lesson in spite of my skirt. By the end of the lesson, I had danced almost with every girl taking the lesson. I did not detect that anyone was uncomfortable or ashamed of dancing with me during the practice. A couple girls did seem more reserved. Later, during the open dance during the night, they danced with me and still seemed just as reserved. Normally, my outfit was not mentioned. One girl walked by me when I first arrived at the ballroom and told me that I looked very nice tonight. When I complimented some girls on their outfits, they complimented me back. Other girls just said “thank you”. I *might* have been fishing for a compliment.  One girl said to me when we started dancing, “I’ll be honest with you.  I’m a little jealous about your legs.”  That was nice of her to say, but she was pretty enough to never rightly be jealous of me!!

By the way, I danced in flats, not the heels I wore into the place.

At one point, I went into the men’s room to wipe my brow. I had worked up a sweat dancing. I walked in and discovered that another man was at the sink. I went to the other sink and rinsed my face and checked my hair. He seemed to react to my presence. I describe his reaction as, “Now what do I do?” I just did what I came to do like normal. I said, “Hello,” and he responded politely. I asked him if he came there often. He answered. Then he finished and left. I did not use the toilet, in case you are wondering.

There were not a lot of noticeable first reactions to me. After the first 15 minutes, everyone had plenty of time to see me. By then, I had almost forgotten I was crossdressed. I did not see anyone try to get my picture. I danced almost every dance. No one ever refused to dance with me. Three times, a girl approached me for a dance.  The last girl to approach me is the girl dancing with me in the picture.

One girl asked about why I was dressed. She said, “Did you want to get to swish and twirl too tonight?” One girl asked me if it was a bet. One time a guy who had given me the only negative looking reaction approached me and asked me why I was dressed and did I lose a bet. I said, “No, I am just a crossdresser.” I think he was still uncomfortable, but he kept talking to me a little. Otherwise, it did not come up.

I grew to forget how I was dressed. It was wonderful. It was delightful. It was also fun! I was a man in a skirt and I nor anyone else cared.

Near the end, I got a few pictures.

I left there and went to a Ruby Tuesday restaurant and had some desert. The hostess took a quick glance down and then right to my eyes. She did not have time to see anything well. She was completely normal with me and seated me. The male server was business as usual. Where they seated me left me in full view of the girl working as the bartender. She gave me several looks. She seemed a little shocked. I did not notice if anyone else paid me any attention other than a glance. The restaurant was not very busy at this late hour. I ate as much of the cheesecake as I could stand (about half a piece) and then I left.

I returned to my hotel and went to my room. It was so nice to be out and feel normal. I LOVE going places where I have something productive to do while dressed! The mall stinks compared to this. In fact, after this outing, I am not sure if anything will be good enough! I may have damaged all of my future outings. So far, for me, this was the Disney World of Crossdressing.

The next morning, I went down to breakfast in black flats, black hose, a blue jean skirt, and a men’s polo shirt. What do you know, but the disapproving man showed up in line behind me. He showed no sign of disapproval that I noticed. However, I did not try to see. The hostess seated me.  My table was beside a table inhabited by a different man. At one point we started talking. It was just normal conversation between two strangers in a hotel. My skirt had no impact.

I did not do any more crossdressing for the rest of the trip. I decided not to fly pretty home because I thought there was a reasonable chance I might run into a co-worker. On the plane, I was seated by a flight attendant. She was very chatty. At one point, I asked her if she had ever had a crossdresser on one of her flights. She said, “No. At least, not that I am aware of.” I told her, “We call it ‘flying pretty’ and it is a major achievement when we do it.” She continued talking to me after that normally.

In summary, I crossdressed a lot and did normal things. I wore a skirt, presented male, and was just another person. If I ever stop finding this stressful, I might just get used to this!


So, what do you think? Should I keep the black jacket closed or open? Or, would it be better if I did not wear it?


dance1 dance2 dance3 dance4 dance5


From → True Stories

  1. Very awesome. I may get the courage to wear skirts out someday. Good job! 😉

  2. Wow you have such an inspiring story! It’s amazing you have the confidence to do what you want and wear what you want. Thank you for sharing your story:)
    xo Olivia

  3. It sounds like you had a really great time once you got past your own nervousness, and seriously the girl who complimented your legs was spot on. Thanks for stopping by my site!

  4. Hi there! and thank you for your lovely comment on my blog, I am captivated by your story and your incredible strength to wear what you want to, and keep the jacket, maybe try a belt with it x x x

  5. Jim2 permalink

    It showed great courage what you did. The only thing I would suggest you do differently is to stop calling it crossdressing. When women wear pants, they don’t call it crossdressing and never did. Only the people criticizing them did. Skirts are clothes that are wonderful for everyone, and should be treated that way. After all, men all over the world wear skirts or skirt-like garments such as sarongs. I would only call it crossdressing if you were deliberately trying to look like you are a woman, and it does not sound like you are.

    • Jim2 permalink

      By the way, men wear skirts at contradances all the time. It is completely accepted. I’ve wondered if it is at all accepted at swing dances. I guess it can be, but it is still very unusual. Is that true?

      • I don’t go to many swing dances, but from what I see on the Internet, only the ladies wear skirts. I have heard about men wearing skirts at contra dances. I wonder how that got started! Thanks for visiting!

  6. Sure enjoyed this blog posting. Love the added pictures. Wish you did more with the pictures. Also I do love dancing and especially dancing backwards in heels. Have to look into the contra dancing mentioned. Have you ever danced backwards?

    • I am not familiar with “dancing backwards”. What does that mean?

      • Dancing backwards refers to dancing ballroom style in a waltz or a rumba or tango or the like. Just the way Ginger did when dancing with Fred. She had to do everything he did, only backwards and in high heels.

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