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Best Store Clerks Ever!

May 18, 2012

This post jumps forward several years.

Having children significantly decreased my opportunities for going out.  I also purged and stopped dressing for over two years.  During those two years, I started struggling with temptations to do other things (nothing illegal) which were less desirable than dressing to me.  Eventually, I started back shopping and dressing.  However, there are no notable stories to tell about this time period.

I suppose I should explain purging before I continue.  Crossdressers have a tendency to dislike what they do.  Occasionally we quit.  We throw away/sell all of our feminine clothes and stop dressing.  Eventually, in my case, I will start back dressing because it never left my mind.

One day I went shopping.  It was my first shopping trip in a long time.  I had such a good time it was hard for me to believe it!  Halloween was coming and I decided I would go try to find a skirt that I could wear.  I am normally satisfied with wearing pantyhose with my men’s clothes or with women’s clothes that could pass for men’s clothes.  Sometimes I wear pantyhose with shorts.  I have even worn a skirt in public on a few occasions.  Being able to feel my legs rub together is outstanding!  I went to the store dressed as a man in my work clothes.  In the car I took off my men’s socks and shoes and put on my somewhat androgynous women’s shoes.  I was already wearing black pantyhose.

I shopped around this one discount store and I started looking for a blouse that I could covertly wear as a man.  I finally asked a clerk for some help.  I told her that I liked to wear girls’ clothing and what I was shopping for.  She was immediately understanding and happy to help.  Eventually, she went to get some help from her manager.  Then the manager came.  I bashfully told her thank you for being understanding.  She told me that it was nothing.  I asked if she had very many men who shopped for themselves and she said she had a few.  One became a friend of hers and they would sometimes go out shopping together.  She was having fun helping me look through the clothes.

After a little while, I went into the dressing rooms to try on what I had.  The manager went back to the front.  I put on the skirt that I had picked out and the only blouse that seemed to fit.  I gathered up my nerve and walked out of my dressing room.  I peeked around the corner and slipped into the store.  The manager saw me and started coming my way.  I met her in the middle of the store wearing nothing but women’s clothes!

We talked for a few minutes.  She said things like, “That skirt fits you great!”, “Don’t women’s clothes feel great!”, and “If I was a guy, I know I would wear women’s clothes.”  We spent a lot of time just talking girls’ clothes!  Apparently, she is really driven by clothes and fashion.  She seemed excited and to be authentically enjoying herself.  Eventually, I relaxed and said that I would love it if she would go with me to browse the dresses.  She brightened up and said OK.  I was still in the skirt.  We went to the dress section while I tried to make sure no customers saw me.  (In particular there was one guy in the store with his wife.)

We looked at a few things.  Nothing great.  Then, I noticed that the man and wife went into the dressing area and lingered.  She was trying on jackets/blazers in front of the three-way mirror.  It was right by my dressing room.  I am wearing a skirt and had I selected a dress to try on, but those people were still there in my way!  I waited a little while for them to leave the dressing room, but the woman was trying on several outfits and coming out to the 3-way mirror.  I finally determined to walk right back to my dressing room and walk past them.  Well, they noticed.  They looked right at me.  I saw her looking down at my hosed feet under the door.  She did not notice that I could see her from over the door.

I changed out of the skirt and put on the dress.  I was ready to go out of the dressing room but they were still there.  I did it.  I walked out of the dressing room, looked both of them in the eye and said, “pardon me” and went out into the store.  I stood around talking with two and sometimes three clerks for 10-15 minutes.  We talked about clothes, and they made cracks about the manager’s odd clothing obsessions.  It felt so great!  A couple other customers saw me.  I was kind of far from home, so I felt safe.

I hated to stop, but I eventually did need to go back to work.  I was there for an hour and a half, I think.  I bought the skirt and a shirt.  As I was leaving, they all told me goodbye and to please come back.  I have gone shopping and tried on clothes before, but it has never been this good!  I wonder if they were being nice because they were being honest, or if it was really all about cheesing me over to get me to buy stuff.  I say that because one of the things that the manager said looked good was something I will describe as “awkward 1980’s school teacher.”

I started getting the craving to one day put on my skirt and go to the store dressed that way.  I also started thinking about asking the manager if could come and volunteer and work for an hour some Friday while dressed.

Several days later, I went back to the store to shop some more.  While I was there I tried on several more tops and I put on a skirt.  I was wearing nude hose and heels.  I walked around the store some and I was seen by two customers.  I even spoke to one of them while dressed this way.  I think this store might be bad for me!

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From → True Stories

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  1. Volunteering While Crossdressed « joeypress

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