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My First Halloween As A Girl – Part 1 – Shopping

April 15, 2012

I decided that I wanted to dress up for Halloween.  In those days, I did not feel like I could ever go out dressed in women’s clothes without presenting myself as a woman.  I have only had on makeup on one occasion before this.  (I’m sure I have put on some lipstick, or blush, or eye make-up a couple times as a teenager, but never a full make over.  I don’t count those.)  The one time before this was the only other time I have gone out in public dressed in a dress.

Shopping.  I had to go get an outfit.  I started visiting stores and sheepishly looking for something that I could wear.

Store 1: I went to a town “far enough” away from home.  I was shopping around the large place and an older woman asked me if she could help me.  I told her I was shopping for myself for Halloween.  She was very understanding and helped me find a couple dresses to try on.  I barely came out of the dressing room but I would let her see the outfits.  I was scared to death.  She acted like I was being silly.  Eventually, I tried on a sweater dress with a long matching jacket.  It was beautiful.  It hid my V shaped figure.  It was over $50.00 and was way over my budget.

I loved the dress.  I said I wished I had some shoes to wear with it.  She told me to go look at the shoes.  I was hesitant, but she said, “No one cares what you’re doing.”  There was another customer over 100 feet away in the store.  They were not paying my side of the store any attention.  I ended up walking around the store in a dress and pantyhose for a several minutes.  I went over to the shoes and found some that were too small, but I walked around in them some.  They were low heels.  Another older lady who worked there came out and the first lady explained that I was working on a Halloween costume.  The second lady was very complimentary.  She said my figure looked great and that women many would be jealous of my legs and figure.

As much as I wanted it, I did not buy the dress.  It was too expensive.  But I could have hugged those two clerks.  They gave me a lot of confidence and relieved a lot of my fears.  (This all happened in a sleepy little conservative country town.)

Store 2: Eventually, I went to a small after-market clothing store.  This store sold clothes that were returned to Chadwicks, or other mail-order store, discontinued items, etc.  They had high quality clothes that were at excellent prices.  I took a couple dresses into the dressing room.  When I came out, I hung the dresses on the “No rack” for the store people to return to the shelves.  One of the clerks, a 22 year old saw me and asked with a sneaky/playful smile, “Were you trying on a dress?”  I told her I was shopping for something for Halloween.

She started helping me.  I tried on something and opened the dressing room door.  I told her I put on pantyhose already.  She looked into my dressing room because I way too scared to come out.  Back and forth we went picking out clothes.  I never came out of the dressing room dressed.  She took me over to the bra rack and measured me right there in the store.  She tried to talk me into having enormous breasts.  I just wanted proportional body parts.  No one noticed me or paid me any attention.  She and I were having fun dress shopping.  She was great (and pretty).  She wanted me to try some old lady dress.  She laughed.  She really liked that one.

Eventually, we found a dress that had a long matching jacket, kind of like the earlier dress except this one was not a sweater dress.  I put on the dress and waited for the clerk to be free.  I had peeked out of the dressing room a few times and saw her still helping someone else.  Then, without warning, the door opened.  There I was in the dressing room in my dress.  And, there outside was a 40ish year old woman wanting to use my dressing room.  I think the shock on both of our faces was priceless!  She apologized and closed the door.  I said, “Happy Halloween!”

The clerk saw me and liked the dress.  I bought it.  Eventually, I bought some affordable heels at Payless.  I still had the wig from my previous outing a few years before.  Now, I was ready for Halloween.

Go read part 2


From → True Stories

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