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I Got Bored During An Outing

November 14, 2012

I arranged with my wife and set up a day to go out of town and crossdress.  I took the day off of work and went to a town an hour or two away from home.  I wore a skirt, short heels, and a blouse.  I have never worn skirts with patterns before this season, so I felt daring, yet comfortable.

I started off kind of late, so I did not eat breakfast out.  I had tried to make arrangements to volunteer all day at a place, but I did not have time to go through their application process for volunteering.  I went to the place and there were a LOT of cars.  I debated about whether I wanted to go in or not and eventually went in.  I only saw two people while I was there.  But I said my “Hello” and saw the place I might come back and volunteer.  I felt no awkwardness on their part due to my attire.

After that, I had only a couple stops scheduled.  I planned on going to one store where I could buy some hose.  Then I went on an unscheduled trip to a Dress Barn because I love that store.  After that, I went to a barber shop and had a hair cut (tentatively planned).  By this point in my day, my nervousness had diminished.  I had stopped worrying about people seeing me.  I did not look around to see if customers could see me.  The woman who cut my hair was very talkative about my clothes, etc.  I changed the subject because I did not want to talk about it any more.

Normally, the thrill of being in public while dressed in feminine clothes is significant.  I have spent my time on previous outings just walking around the mall and going to stores, but with no purpose.  This time, I did not feel the same way.  I did want to be out among people, but I was not interested in going places where I had no purpose.  I went to the mall and almost did not go in.  I just did not have any significant purpose to go there.  Going in seemed boring and pointless.  I did go in because I would like to find some nice slacks that are long enough for my unusually tall frame (compared to a woman).  I did not stay very long.  I was disinterested.  I did not pay any attention to other customers or whether they were looking at me.  I even walked through the makeup/fragrance section.  I am normally intimidated by the stares of the “catty”, pretty girls who work there.  I know my clothes are somewhat tacky and from second-hand shops.  I also know that I am a guy in a skirt… those girls make me feel inadequate and self-conscious.  However, this time, I walked right through the middle of them and even stopped to ask a tall girl where she buys her pants.  (She said

I decided to go to the hosiery section of a fancier anchor store in the mall.  I went there in order to ask about black pantyhose.  I cannot seem to find any that I think look nice.  The sales associate seemed like she had never had a crossdressing customer before.  I told her what I wanted and we walked over to the rack.  She seemed unsure how to talk to me and oblivious about why a man would dress like a woman. She asked me at one point what my wife thought of me going out dressed.  I tried to explain how I started out as a kid petting anything silky.  I told her how I eventually tried on silky feminine stuff.  I told her that my wife does not like it, but she tolerates it.  The sales associate changed during this conversation.  Before I left, she smiled at me and said, “You have a great personality.”  Now, I do not know why she said that, or if she is correct, but I felt like it was a very decent thing to say to me…  On second thought, that is what people say about their less unattractive friends when they are setting them up on a blind date…  hmmm…  Maybe I should not appreciate it.  🙂

I left the mall and went to lunch.  I went to a nice restaurant with a waiter.  It was a non-event.  No one cares what I wear.  What I mean is most people take an initial look at my clothes and then look me in the eye and, if possible, they might sneak a second look at my outfit.  But they do not react otherwise.  The other people around me in the restaurant never even took the second look.  I tried to get the waiter’s attention at one point, but failed.  A lady at another table (who had an easy view of all of me) asked me to tell him that she needed lemons if I got his attention later.  I was just another guy in the restaurant.

After that, I went to a big-box office store.  There were only ~25 year old men working there.  I did not care.  I bought what I had planned to go in for.  I talked briefly with the guy who took my money.  Then I left.

After that, I started driving toward home.  I stopped at a big shoe store on the way.  I wanted some casual ladies’ shoes, but they did not have them in my size.  I decided to go to the men’s section and get me some athletic shoes.  I shopped around and tried on some shoes and then went to the dress shoes.  I eventually bought the athletic shoes.

I visited one more store on my way home because I just did not want to stop being dressed.  “Just a little bit more.”

Later that evening, my wife, who was uncomfortable about me going out yet still consented, asked me what I did on my outing.  She patiently listened to what I have listed here.  She asked me what I wore.  She later told me she loved me.  She is trying so hard to remain a relevant member of the conversation.  I tried to communicate to her previously that this has always been part of my life and I assume it will not go away.  I have told her several times that I do not like keeping secrets from her.  She is trying to create an environment where I will not feel like keeping secrets.  It is hard for her, but she is trying and it warms my heart.  She does not realize it, but this was the first time I have ever had anyone who was not a stranger that I could talk to about my crossdressing.  I love her no matter what.


From → True Stories

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