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My First Skirted Outing

May 3, 2012

There is a store where I would often go when I have an outing.  It is an hour from where I was living.  I would go there in shorts and pantyhose and shop.  On one visit, I bought a skirt.  It was a short, sassy black skirt.  It was made of a spandex material, but it was not snug on me.  It had built in shorts.  It was cute, but I feel like it was too short.  Crossdressers should avoid short skirts, in my opinion.  (I think men should avoid short shorter than their knees too.)

I bought this skirt and started getting the urge to wear it home.  I asked the clerk if I may put it on after buying it.  And that’s what I did.  It was SO hard to walk out of the store wearing it.  It was night.  It took a moment for me to build up enough determination.  I walked out of the store, in my skirt, but as a man.  I was in public in all women’s clothes, wearing a skirt!  It was a major milestone to me.  It was a non-event.  I believe no-one saw me.  It kind of looked like shorts.

After that day, I started getting the craving to wear a different skirt and black hose, and go back to that store to shop.  Then, I would wear the same hose with shorts and go to the mall.

I went to the “strip mall” where the store was.  I was wearing a white blouse, black knee-length skirt, black pantyhose, and black dress flats.  No make up or wig.  I was a man in a skirt.  I found a parking space near the store.  I was rather scared.  I waited for the coast to be clear, but people just kept coming.  People take an incredible amount of time getting out of their car.  People took forever leaving once they were in their car!  Finally, I open my door, the coast was clear, I lift out my leg, then the car behind me started honking.  Its freaking alarm just went off.  Every one of the stores had people peeking out the doors and windows and seeing me sitting in my car that was in the direction of the honking.  I thought, “Great, they’re gonna call the police on me.”  They did not.

Finally, the coast was clear and I went for it.  I got in the store with no one seeming to see me.  There was a clerk by the door.  She greeted me like normal.  I told her I was so nervous and she acted like she did not understand why.  I shopped there for over an hour.  A couple customers saw me.  I tried on a lot of outfits.  The clerks offered me a couple of nice things.

When it was time to leave, I was bold enough to leave there and walked down to the shoe store.  There were some people around.  One car in a parking space had people in it.  They looked at me with distraught looks with their mouths hanging open.  I went into the shoe store not knowing if there would be customers.  I went in and decided to just go for it.  There were several customers who had a chance to see me, but I do not think they ever noticed.  People are largely inattentive, I believe.  They had nothing I liked in my size, so I left.

I decided I would attempt the mall, not in shorts as I previously fantasized, but in my skirt.  This mall was far enough from my home, that I did not expect to see anyone I know.  I found a parking space, but it was not close to the building.  I saw by the door that there was a man and two women  talking. I thought,  “If I’m gonna do this, I gotta do it!”  I got out of my car and proceeded toward the door.  The man looked my way when I was visible to him.  Then the woman beside him looked my way.  Then she turned right back to the others and kept talking.  He seemed to not look my way.  They kept talking as I walked up to about 15 feet way from them.  I looked at their reflections in the door and no one appeared to be looking at me.  I went in and glanced back.  The man was looking my way.  I could not see if either of the others ever looked.

I entered the mall into an anchor store.  I found it was crowded.  I walked into the racks for cover.  I navigated my way through the store staying between racks of clothes.  Since I avoided aisles, no one could see me.  When I did cross aisles, I could see no one paying me any attention.  I was invisible.  I found my way to the entrance to the main mall.  I really wanted to walk the mall in my skirt.  I was on the second floor.  I decided I would take a short walk into the main mall area and then walk right back.  I waited until the coast is clear.  I waited and waited.  Finally, I decided I would go for it.

I walk out of the anchor store into the mall.  This part of the mall is rather deserted.  It was not a great place to place a store.  There was nothing to hide behind.  I felt like I was so exposed.  There were no distractions to draw attention away from me.  A lady was cleaning glass where I was walking.  She never looked at me.  I got to my planned turn around point and felt emboldened.  I decided to go a little further.  Then I went a little farther.  Soon, I was walking where people were standing in the doors of their stores and could see me.  People would take their first look at me, and then they would look away.  They were trying not to stare. I was an oddity, but I was being treated with reasonable respect!

The farther I walked, the more crowded it got.   Soon, I was walking between people who are standing by the store they work at and people working in the little kiosks in the middle of the mall.  (There were not many kiosks on the second floor).  I walked into the next anchor store.  I looked and saw a clerk in a jewelry store looking my way and talking to her peer who then leaned to see around a display to see me.  I got up some nerve and then walked out of that anchor store.

I decided to walk the entire mall.  I got bold enough to pass people who were walking slower than me.  I stopped in a store along the way and the clerk was helpful and disregarded my clothes.

I made it to the other end of the mall.  I walked around a little and decided to find the makeup desk.  I was going to ask about how one goes about getting a makeover.  (I do not care about being a girl, I just like the clothes.  But at this point in my life, I figured I had to dress as a girl with makeup to get away with it.  Remember this was my first skirted outing.)  Well, I had to use an escalator.  That was scary.  I found the makeup desk.  I talked to this extremely nice lady.  She kept asking me about what I use to cover my whisker shadow, what foundation I use, what powder…  I do not wear makeup.  I do not have answers to these questions.  She finally talked me into sitting in her chair and she demonstrated some foundation on me in a couple shades.  It was wonderful to be treated so considerately when my whole life I felt like I would be an outcast if anyone knew!

I thanked her and headed back toward the mall area.  I was on the first floor.  I thought, I’ll walk back on the downstairs portion of the mall.  (Bad idea.)  The first floor of a mall is CROWDED!  There are tons of kiosks in the middle of the mall with clerks everywhere.  Customers were all over.  There was less room to walk, so I was passing people going both directions within inches of one another.  There were more popular stores on the first floor.  I passed the Lady Foot Locker and the clerks were by the door.  One rudely laughed out loud at me.  One person gave me a rather disapproving look.

I returned to my store of origin.  I made my way back up the escalator.  I went back to my car and went home… successful.  Granted, I probably have done enough damage to my heart that I will die at 40, but it was quite the experience!

During my trip, I made eye contact with several people. Many looked away, so as not to stare.  I think it would be more polite to say “hi” to the crossdressed person just like anyone else.  One girl during this outing kept eye contact and smiled.  No telling if it was a friendly smile or a humorous one.  But it was not mean.  Once I read on a crossdressers forum where people were discussing whether it is inappropriate to approach another crossdresser you see in the wild.  If you go up and say, “I crossdress too!” you are saying, “You totally do not pass!”  I recommend, go up and say, “I like that <garment>, it is cute!”  Then you can drop in that you wear one that is similar or whatever, if you want to confess your crossdressing.

During my outing, I stopped and talked to a few clerks in the mall.  Every one was completely normal with me.  They acted like I should know my business about the products I was interested in.  I asked most of them if they got lots of men.  I figured the answer was yes because they seemed so natural.  Most said no.  In fact, they all seemed to say that the only men they get are shopping for their wives (this was frequently followed with “…at least I think they were.”)

Here is a picture of me in the first store with a sales person:

Let me add one more thing.  I talked to this sales person a good bit.  She was not disturbed by my odd clothing interests.  She was kind and helpful.  After discussing how I just love to wear women’s clothes, but I don’t want to be a girl, she said that she thought she would prefer that her husband craved dressing up instead of what he was attracted to.  She did not elaborate.  I have also heard my wife say that she would rather I be this way than a list of other ways.  Of course, she would rather I be just like she perceives her father to be instead of this way.

Have a great day!

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From → True Stories

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