Skip to content

Lingering Waitress

I decided to have an outing during lunch.  I changed into a black skirt, a dark top, and heels.  I went to a restaurant.  There were no customers in the dining room.  I walked up to the counter and asked if I should seat myself.  The waitress was on the phone with a customer.  She nodded.  I seated myself.  The waitress, a young, polite, seemingly normal girl, came to my table and took my order as it usually is done.

When the waitress brought me my drink, she tried to start a conversation with me.  She seemed to be fumbling for words.  She excused herself at one point to take care of something in the back.  When she returned from the back, she delivered my food.  She took my cup to refill it.  I decided to give her something to talk about since she seemed to want to talk.  I asked her why she was not in school.  She told me her whole story about how she is in high school, but she is doing her schooling at home.  I ate half of my meal while we talked.  Eventually, I asked her to go fill up my cup that she had been holding.  She brought me my drink and then she talked to me only briefly.

At one point, someone from the back of the kitchen came to the counter to visit with the waitress.  I wondered if the waitress told the staff in the back there was a dude in a skirt in the restaurant and this person was visiting the front to get a look.

As the time approached a more traditional lunch time, other customers started arriving.  The waitress became busy.  I finished up my meal.  I came up to the counter to pay.  The person from the back left the counter area and visited the drink area.  From the drink area, the person was (conveniently) able to get a good look at me at the counter.  I paid my bill and we said our good-byes and I left.

Not wanting to stop being dressed pretty, I stopped in at an ice cream shop that I occasionally have visited while dressed.  The owner was there, like usual.  She ended up chatting with me while I ate my ice cream.  It was like I was nothing unusual.

Now, have you ever had a waitress or other similar person linger around you while you were crossdressed?  The girl mentioned that she had some social trouble in school and that was what led her to do her schooling from home.  Perhaps she was more alternative than she appeared.  She never did anything inappropriate or “forward”.  She just wanted to talk to me.  Once, I experienced having two young girls try to speak a few words to me.  However, they did not try to start a conversation.  I am curious to know what this means.  It is interesting.

Fancy Japanese Restaurant

I took a lunchtime outing recently.  I went to a fancy Japanese restuaurant and ate lunch.  I had been driving down the road while crossdressed, looking for somewhere to eat lunch.  I saw a new restaurant that had one vehicle in the parking lot.  It looked safer than anywhere else.  I was wearing a knee-length denim skirt, an orange top, a navy blue cardigan, off black pantyhose, and flats.  As always, I was a man from the neck up.

I walked in.  The waitress saw me and walked up to me.  She seated me and took my order.  Later she filled my cup, etc.  The waitress never paid my outfit any attention.  I never saw her even give me an up-down-up look.  I have heard it said that Japanese people are more accustomed to crossdressing than other cultures.  Her behavior suggests that it is the truth.

A group of four men arrived and were seated near the booth where I was seated.  They looked like engineers.  When they came in, I uncrossed my legs so that my foot was not sticking out of the booth.  I slid in a little deeper into the booth so that my bottom half was not easily visible.  One of the men did look toward my feet before I had moved.  His eyes lingered for a moment while he was getting seated.  Then he never looked again.  None of them looked my way.  Eventually, I paid my bill and placed some extra money on the table for a tip.  Then, I stood up and walked past their table.  I did not look back as I walked to the door.  They were talking and eating.  It is possible that no one looked at me.  The table did not become silent as I turned the corner and walked away out of sight.

I declare that I will have achieved something important when being crossdressed around a group of men no longer makes me uncomfortable.

Minor Outings

I once would not have said that going anywhere out in public during the day while crossdressed was a “minor outing”.  However, all of my recent outings are, to me, minor.  In the past few months, I have not had any “major outings”.  I have only left work during lunch, dressed up, and gone to a couple restaurants or to my barber shop.  I have worn the same clothes that I have worn previously, and gone to the same places that I have visited previously.  I think these outings are minor because I am accustomed to going to these locations.

There is a danger here.  If I were seen by someone who knows me, the same consequences would result from a “minor outing” as a “major outing”.  When it comes to security, there are no “minor outings”.

OK, enough philosophy.  Here are some things I have done:

I have gone on my monthly barber shop visits.  I had grown my hair and beard for a few months during the summer for a drama.  Once I was done with that, I had it all cut off and returned to going to the barber shop.  My barber, a lady, will acknowledge my outfit by saying something is pretty, but then it really is not a topic.  It is minor to her too.  It is not awkward for her to mention it and it is not common for it to be discussed.  Basically, it is a normal relationship.  How is this not a MAJOR thing!?!

The last time I went to the barber shop, there was an employee there I had never met.  She was the weekend employee who was there during the week to fill in for someone.  I was just a man in a skirt.  She talked to me like normal and never reacted to my clothes.  When it was time to wash my hair, she did it.  Near the end of my visit, I thanked her for being so understanding.  She said she did not care.  This was not patronizing.  I suppose it was like piercings or tattoos.  My crossdressing was just some feature of a otherwise normal person.

I have gone out for lunch while crossdressed.  I have gone to the same restaurant a few times.  That is always stressful because, until I walk in, there is a mystery of who is going to be in the dining area.  Also, having to walk across the room in order to fill my drink is stressful when there is a table of construction workers or some other type of laborers.  They have never treated me any worse than “white-collar” workers, such as bankers.  However, those men cause me stress.

One somewhat unusual thing I did recently was I went shopping for myself and openly telling the clerk it was for me.  I went to the ladies’ underwear section in a store and told the clerk who came up to help, “I am a crossdresser and I am looking for underwear with a wider crotch.  She helped me as though it was an ordinary event.  I think it was roughly an ordinary event for me too.  I asked her if she had a lot of male customers.  She said no.  It was not common for men to shop from her, but she did not react any differently to me.  When I did this, it was not frightening.

Attended a Class in a Skirt #5

I attended my final sewing class.  I am sad.  I discovered that all day long on class days I would look forward so very much to going to class.  I would remind myself throughout the day that I get to wear something pretty in X hours.  It was like the last day before Christmas break at school.  This time I wore my orange maxi skirt with a black, acetate top and an unbuttoned, white, collared shirt over it.  I wore nude pantyhose and my strappy, black flats.  I was a man in a [pretty] skirt.

Let me interrupt my story here to say something.  I have a collection of maxi skirts that I wear in the summer while I have leg hair.  I wore four different skirts to the first four classes.  However, this week I wore a skirt that I previously have worn to class.  This is a clear sign that I should get rid of any skirt I have not worn.  If I would prefer to re-wear a previous skirt than wear one of the remaining ones, then I probably will never wear them.  I do not like them enough to keep them!  Thank you for your patience.  Now, back to the story…

I was the third person to arrive for class.  The door was locked.  As I approached the ladies waiting in the hallway, one of them, “the experienced sewer,” greeted me.  After I said hello, the other lady, “the thrift store owner,” said hello.  I thought it was nice that the experienced sewer greeted me without me saying something first.  Later, she asked me how my Father’s Day was.  We stood in the hall and talked while waiting.

When we were let into the classroom by the teacher, we all started working.  There was very little talking.  The woman who sat to my left asked me for help a few times.  I did my best to help, but sometimes I did not understand the instructions on her pattern any better than she did.  The fact that she turned to me, a man in a skirt, for help was encouraging.  She never acted like she found me creepy or anything.  I think she trusted my ability.

At one point, I realized that I was walking around the room doing what I needed to do and I was paying my outfit no attention.  I was completely at ease!  How beautiful it felt to realize that!

I noticed that when my teacher helped me today, she did not appear to be apprehensive.  She seemed apprehensive during a previous class.  I believe it was due to me wearing a skirt that day that was identical to hers other than the color.

I finished sewing the item I was working on.  I tried to decide whether to leave early or to start another project.  Then I remembered that I had a dress that is too big in the hips that I wanted to take in.  I marked the dress for sewing.  My teacher came over and gave me advice.  There was no awkwardness about the fact that she was teaching me how to alter my dress.

By the time I had sewn both sides of the dress, it was time for class to end.  I packed up my stuff and said goodnight.  Since it was the last night, I told the group good-bye and thank you for being so nice to me.  I did not know what to expect when I came to class.  I said that I do not always dress like this.  I told them how this was the first time I have ever done something where I would get to know people and possibly make friends.  In retrospect, I suppose the small group meeting I attended at a sort of religious organization might have also been a chance for me to make friends… but this was clearly a different and more interactive experience.

They responded very politely.  The thrift store owner invited me to pay her store a visit.  The teacher said that if I had any more questions about my project to feel free to contact her and ask.

And that’s it.  A man in obvious women’s clothes can take a sewing class with a group of ladies and not be harassed, rejected, ignored, or anything negative.  I suppose it is possible that I could have been spoken poorly of when I was not present.  But by the end, after they had enough opportunities to to get to know me, I hope that they did not have anything too harsh to say about me.  I suppose every experience like this will be unique.  I should expect the best and the worst.

I have found that the community that I live in is fairly kind to me.  I live in a fairly conservative part of my country.  Also, I have traveled around and have done a lot of my longer-term dressing on trips.  Everywhere I have gone, I have received similar treatment.  I guess I should say as a disclaimer that I have always tried to behave respectfully and normally as possible.  I dress conservatively and usually in rather plain outfits.  All of my skirts hang to just above my knees or are longer.  I normally wear flats.  I do not want to look like a stereotype.  I want to look like what I am, a forty-something, married, parent of young children.

Attended a Class in a Skirt #4

I attended my fourth sewing class while dressed pretty.  This time I wore my multicolored, green, silky skirt with a brown top.  I wore nude pantyhose and black flats.  I think the shoes do not look perfect with the outfit.  I chose not to wear my nude heels with this outfit to class because those heels are too tall.  I already cannot cross my legs under the tables in the classroom.

I came in, said, “Hi,” to those present, and went to work.  No one talks in class.  It is such a quiet room.  Things are said, but not for long and not very loudly.  It is like a library.  I will try to talk to people, but no significant conversations result from my attempts.

I accomplished a lot in class today.  I finished everything for which I had a pattern.  I completed a second item that I was making up as I went.  I put on the second item and I used my phone as a mirror so I could get a look at myself.  I put down my phone.  The woman in the row behind me offered to take my picture and had her phone in position.  She was going to take my picture and then send it to me.  I declined.

A few moments later, after I took off the item, I asked her if she would take my picture with my camera.  She accepted.  We tried a few locations before we found a backdrop that was not white.  The white tunic that I made for a costume was blending into the white walls in the room.  While I was getting ready for her to take my picture, a second woman stood up and got her camera/phone ready to take my picture for me.  I asked the second woman not to take my picture.

Later, I said to the second potential photographer that I do not dress like this all the time and I try to control what pictures exist of me dressed up.


So, I have a picture from this class.  I also have a conspiracy theory.  These two women both wanted to take my picture “for me”.  I thought, “What if they are offering to take my picture and send me a copy because they actually want to take a picture of this skirt guy to show to their families who have been hearing stories about me.”

When class was over, I cleaned up my things and waved good-bye the last two classmates who remained.  They smiled or waved.  They were in the middle of a conversation with the teacher.  The teacher did not turn to tell me good-bye.  The teacher was talking when I departed.  So, maybe that does not mean anything.  She had spoken with me more casually during class than on the previous week.

I went back to that Cracker Barrel from last week.  I put on my nude heels for this.  The restaurant was a lot busier than on my previous visit.  I was uncomfortable.  I walked across the front walkway of the store on the outside.  I glanced into the many windows in order to see if there were any customers who knew me.  None of the roughly twenty customers looked familiar.  I went in.  There were approximately fifteen people in the store area.  I tried to browse far away from the crowd while waiting for them to leave.  An employee walked by me to check on me.  She spoke kindly to me and walked on.

I browsed some more and then went to the employee who was visiting with two other female employees who were working on a store display.  I asked if the woman I hoped to speak to was working.  She was not.  During my previous visit, an employee stopped and told me that she once had a neighbor who wore skirts and had a beard.  I was hoping to ask her about him and to hear about another guy like me.  One of the ladies working on the display had spoken with me last week.  She told me it was nice to see me again.  They complimented me on my skirt.  The first employee talked to me the most.  She seemed patronizing.

I have found that I get a few slightly different reactions.  People do not say these things, but their behavior and words imply these:

  1. “You are not welcome here.” (I do not like you or respect you.)
  2. “You have as much a right to be here as the other people, but I’m not excited about it.” (I do not like you, but I respect you.)
  3. “You are welcome here.” (I do not care.  I respect you.)
  4. “You are welcome here because we accept all kinds.  Even people like you.” (It is so good that I am here for you,  you poor little thing.  The last half of that could be translated to the Southeastern American phrase, “Bless your heart!”)

This employee was a #4.  Normally, the public is #2 or #3.  Most employees communicate #2 to me.  I have not experienced #4 in a long time.

Eventually, the crowd diminished and I collected the candy that I wanted to purchase.  Another employee saw me and said it was good to see me again.  She was the employee at the cash register who took my money on the previous visit.  I made this trip’s purchase and walked to my car.  The group of older people who were in the store were now in their cars.  I looked over and saw the driver of one car giving me a long stare.  I think they had seen me in the store.  They seemed to be looking in my direction often when I was inside.  In retrospect, I should have waved at her as I crossed the parking lot.  I, however,was walking in heels and was too consumed with trying to do it well to think about waving.  Some things just take more focus than others…

Attended a Class in a Skirt #3

I attended my third class while dressed pretty.  This time, I wore a black and white striped skirt, black pantyhose, flats, a red top, and a black cardigan.  From the neck up, I am a man.

When I arrived to class, a lot of the class was already there.  When the teacher walked in, I was near the door.  I noticed her take a quick sideways glance at my skirt.  Then I realized that she was wearing a gray and white skirt with the same stripes as my skirt.  We were wearing roughly the same skirt.  I felt like the teacher might have expressed some apprehension when she helped throughout the evening.  I wondered if us wearing similar skirts was bothering her.  I felt bad about it.  She looks way better in a skirt than I do.

Beyond that, I was just a member of the class.  Nothing interesting happened.  People did not pay my clothes any attention.  Some talked to me like normal.  I learned some and put it to use.

After class, I walked out into the hallway.  My hands were rather full, but I turned to close the door to the classroom.  A janitor was in the hallway walking toward me.  He made some obvious glances at my clothes.  I said hello to him and he replied appropriately.  I shut the door and walked down the hall.  He was walking in the same direction.  When I came to the exterior door, I said good-bye.  He was polite and responded wished me the same.  He seemed a bit surprised or amazed at what he had seen, but he did not seem hateful.

I went to a Cracker Barrel restaurant on my way home to get some candy.  I also went because I did not want to stop being dressed pretty in public.  Cracker Barrel restaurants have a store in the entrance area/lobby for customers to browse while they wait to be seated.  They have old timey candies, etc.  There were very few customers in the restaurant.  Therefore there were about six to eight employees in the store area restocking the displays.  They all happened to be female.

I walked in and I received several obvious looks.  After their first glances, about half of the ladies did not react to me more.  The other half took a few more obvious looks when I was near.  The girl at the cash register was very natural and conversational with me.

I made my purchase and started to leave.  Then, I remembered something I wanted.  I asked another employee if they had what I wanted (a money pouch to replace what I normally carry).  She had me follow her to where they might be.  They did not have what I was looking for.  I thanked her and started walking toward the exit again.

As I approached the exit, I passed two female employees who were working on a display.  The older one spoke to me and said, “You’re not from <a specific town>, are you?”  She had an accent.  She was not from my country.  I was not from the town she asked about.  She said she used to have a neighbor in that town who liked to wear skirts.  She said he always had a beard.  I wish I had spoken with her more about this neighbor.  Maybe I will go back.

I stopped at a gas station to buy some milk to go with my candy.  Store keeper was listening music that sounded to me to be from the Middle East.  He looked Middle Eastern as well.  He spoke politely to me and treated me normally.

I ate my candy as I drove home.  When I changed out of my clothes, I was very pleased to find that my shirt was not sweaty.  I was very relaxed this evening.

Attended Class in a Skirt #2

I went to my second class while dressed pretty.  I was wearing a long, black ankle-length skirt.  I also wore off-black pantyhose and my black flats with straps.  On top, I wore a lightweight, orange blouse and a white, collared shirt as a cardigan.  Otherwise, I looked like a man.

I arrived about twenty minutes early to class.  Another classmate was sitting in her car, eating.  We waved to each other as I walked into the building.  I was the first person in class.  A few others arrived together shortly later.  I asked the people near me, “What is your project?”  They showed me their patterns and I shared mine with them.  I detected no awkwardness in them.

I felt more apprehension today, but it quickly faded when I arrived to class.  Everyone arrived, including the teacher and class started.  The teacher had us all come up to her table to watch what her demonstration.  I was standing with the others from the back rows of the classroom.  The front row people stayed seated.  I felt a over exposed.  I was standing where everyone could look at me.  However, I never saw anyone sneak any glances at me.  I relaxed.

Then we started working on our projects.  I had to stand a lot while I worked.  I did a lot of bending over my table.  I was aware that the ladies behind me had a view of my backside when I bent over.  I made sure that my shirt was pulled down to cover my waistband.  I felt distracted because I did not want them to see any lines indicating what I wore underneath.  Eventually, I gave up on that.  Hopefully the did not pay me any attention.

The time for class to end passed.  We all kept working.  Every few minutes, a student would leave.  If I said good-bye they would reply.  I wanted to ask the teacher a question before I did any cutting.  I did not want to go home and do anything that I might want her input on.  She came to my desk and started talking to me about my options.  While she was talking to me, the three other remaining students left.  The teacher and I were the only ones who remained.  (This was not on purpose.)  She did not seem to be at all uncomfortable to be alone with me.  I finished up and she and I left together.  While we walked down the hall, we talked about some non-class topics, such as family and work.

We went to our respective cars and departed.  It was completely normal, decent evening.