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Going Out to Eat Crossdressed

November 7, 2012

I had to go to work on a Saturday.  I took some clothes with me.  I decided to go to a Mexican restaurant that is 45 minutes away from my home.  I got to the restaurant at 3PM.  There were almost no cars in the parking lot.  I put on my skirt and took off my pants.  I put on some black flats.  I kept on my long sleeved, mens, collared, pull-over shirt.  My skirt has a beige, brown, and black pattern (Normally, I just wear black or solid colors).  As usual, I had no makeup or wig.  I was just a man in femme clothes.

I sucked up my courage and got out of my car.  I walked up to the building and peeked in the window.  The restaurant was almost empty.  I went in.  There were two male servers sitting at a table putting silverware into napkins.  They both glanced my way and I got the “up and down glance”.  One seated me in a booth.  A table of three women was the only populated table in my half of the restaurant.  They never paid me any attention. I sat down in my booth, crossed my legs and waited.

I felt like my waiter seemed a bit nervous interacting with me.  He was professional and kind.  The other waiter walked past my table a couple times and I looked up to see him looking at my lower half.  He quickly shifted his glance to my face.  Other times, he could have walked past my table, but he did not.  My food came and I ate.  I noticed my hands were shaky.  I never saw any staff from the kitchen come out and glance my way or walk by my table for a look.  I relaxed, eventually.  Another customer came into the restaurant.  He sat a few booths behind mine and talked on the phone.

When I finished my meal, I got up to pay.  A family was about to come in which made me want to stay in my seat.  However, the table of women were leaving, so I got up to go too.  I got in line behind the woman who was paying and waited my turn.  The family came in and was seated.  Then I paid and left.  It was practically a non-event.

Next, I went to a clothing store where I recently bought the skirt I was wearing.  It was VERY busy.  I sat in the car a long time.  This location is closer to my home than I normally would allow myself to have an outing.  I finally stood up and walked into the building.  There were customers spread all over among the racks.  I hurriedly walked in between the clothing racks.  Then I weaved away from other customers.  I stopped in a safe place and caught my breath.  No one paid me any attention.

The girl who sold me the skirt saw me and I beckoned to her.  She came over and said, “I like it.  I like the shoes.  They were a good choice.”  We talked briefly and I told her about the restaurant.  She said, “That must have been scary.”  I had this conversation with her while a female customer was shopping on the same row as us.  The SA had to go deal with some customers at the register.  I relaxed and did some shopping.  I found a brown blouse that looked like it might go with the skirt.  I went to the changing rooms and tried it on.  It looked so good, I pulled the price tag off and got out the cash to pay for it.  I was going to wear it out of the store!

When I was ready to leave the changing room, there was a mother and a daughter standing in front of the 3-way mirror.  The daughter had been trying on even gowns.  I contemplated waiting.  But, I opened my door and stepped out and said, “Wow, it’s beautiful!”  They both said thank you.  Then the mother took a look at my skirt.  I did not linger.  I never saw the daughter look my way.  I walked up to the cash register and paid my friendly SA.  I do not know who saw me, but I did it.

Later, at work, I was the only person there.  I had been there for a couple hours.  It was getting late and I started thinking that I could go get my skirt and put it on.  Eventually I did it.  I worked for several hours at my job in a skirt.  Copy machines make some noises that can terrify a crossdresser in such a situation!!

After work, I went to a somewhat classy 24-hour restaurant (not Waffle House).  I was still wearing my skirt.  Again, this was too close to home.  I could see in the restaurant because it was dark outside.  I saw no one I knew.  I went in.  The hostess looked down suddenly and saw my skirt and did not lose composure in any way.  A couple male servers were loitering there.  They looked at me and then walked back toward the kitchen.  The hostess seated me.  I never saw anyone from the kitchen come out to see me.

I ordered my food and could never tell if my server ever noticed my outfit.  Later some teenagers came in.  That was stressful.  One girl looked toward my feet as she walked by.  I noticed no other sign of recognition.  I finished my meal and I got up and walked to the cash register.  The teenagers would have been able to see my back as I walked away.  I did not have any small bills for a tip, and I was NOT going to go back to the table where the teenagers and their camera phones were!

I paid for my food while a couple sat in the lobby behind me.  I spoke to the hostess and mentioned that I was nervous.  She said, “Why?”  I said, “Because I am in a skirt.”  She said, “So?”  I mentioned the teenagers to her and asked her to please put my tip on my table.  She did and I left.

That was it.  Almost no one reacted in any way other than glancing down.  I live in a somewhat highly populated part of the world, but it is sufficiently conservative to have a reputation locally.  However, people are decent and they looked at something unusual and then treated me with respect.  The end.  …and I’m loving it!


From → True Stories

One Comment
  1. Some people have commented that they are concerned with living in a conservative area. I find that there is more tolerance and acceptance among folks who have conservative or libertarian view than those who espouse liberalism. Most conservatives have a live and let live attitude. You do not bother them or take their money or demean their values and they will afford you the same. Many on the left feel a sense of superiority and want the government to impose their values on others.


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