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Early Christmas Shopping at Ann Taylor

Once or twice a year, I will have an experience as a girl where I come away so elated that I barely have words. Getting my first pedicure at the day spa was one such experience, and finding/buying an Elle dress that I had my heart set was another. Well, this morning I had perhaps the funnest shopping experience ever when crossdressed as a girl.

Over the summer, I introduced a dear friend of mine, Karen, and I posted a few updates where Karen visited me during the summer and we went shopping, went to a concert, and then had dinner on two nights among other things. Karen is one of my very special friends, and when she found out that I would have some girl time at the start of November, she innocently asked me, "Would you like your Christmas present early?" I had a good idea what the gift would be and knowing that I likely won't have girl time the weeks immediately surrounding Christmas, I told her that I'd love an early gift.  As a result, Karen presented me with a gift card from Ann Taylor, the brand that Karen and I both adore.

I wanted to make this shopping trip special, and so I took the morning off from work so I could drive to the outlets and spend the morning shopping at Ann Taylor.  As for my outfit, I decided to keep it as simple as possible, so I wore a pink and white striped tee from American Outfitters that I bought when shopping for my Minnie Mouse costume, and then I paired that with some simple blue jeans from Old Navy that I rolled up at the cuffs.  I did wear nude pantyhose beneath my jeans just because, and then I was also happy to wear the new white canvas shoes that Danielle bought me last week when she acted as my Sugar Daddy.

It was a little bit late in the year to wear this particular outfit, but I just couldn't resist, and so I drove to the outlets in my tee shirt and jeans with a jacket prepared in the car just in case. When I arrived at the outlets located in a ski resort town, I knew that I would need that jacket as soon as I opened my car door. I mean, I would have been fine scooting into Ann Taylor with just the tee shirt, but any other girl would have worn a jacket, so I pulled my guy running jacket on over my outfit and headed for the door.

My plan was to arrive at Ann Taylor as close to the morning opening as possible, and as I entered the store, it was clear that I was the first customer. A sales lady quickly came over welcoming me to the store, and I informed her that I would just like to browse for a bit. Due to Karen's generosity, I knew I had $100 to spend in the store, and so I scoured every inch of it looking for great buys and items that would work with my wardrobe.

After about 10 minutes, I had accumulated a few tops that I wanted to try on, and the sales lady came back asking me if I wanted to try them on. I told her that I did, and so she asked for my name and said that she would prepare a fitting room for me. She also said, "By the way, my name's Carrie." That is actually the first time that has ever happened to me where they've reserved a fitting room for me, and I didn't know that women's stores had a such a practice. Carrie took the items from me, and then she would check back every few minutes to see if there was anything else she could take to the fitting room.

I probably spent close to an hour going through all of the inventory on the sales floor, and when I was ready, I told Carrie that I was ready for the fitting room. She took me in and there on the outside of fitting room #1 was the name Lisa. My goodness, I don't know when I've ever been happier, and as I entered the fitting room, all of the items with hangars we were neatly hung up, and the sweaters and tops that didn't have hangers were neatly folded on a small table. Carrie told me that she would be back to check on me in a few minutes, and so with all of the cute clothing there ready for me, it was time to go to work.

The first item I tried on was a black skirt. For some reason, I feel as if I need a few dressier skirts, and so I found this skirt on the clearance racks. The skirt was a size 10, and I loved the look of it, but I definitely needed a size 8. When Carrie came back to check on me, I handed her the skirt and asked if there was a smaller size. She came back a few minutes later informing me that there wasn't, and so I didn't buy the skirt.


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