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A day of firsts, seconds and thirds..
On a recent trip to a different city, I packed a little extra stuff in my luggage hoping to get an opportunity to dress. I had also been reading on the experiences of others here on shopping in the stores. So I also had that on my mind but I wasn't sure. I had planned to check in my baggage but realized that it would fit in the carry on at the airport. Now I had a few items of clothing and basic makeup which would typically not be there in a man's luggage but I decided to own up to it and not spend additional money to check in the baggage. As luck would have it, my baggage was selected for hands on screening because of a large tub of moisturizer which could hold more than 3 ounces. To find it in the luggage, the elderly lady saw the bras, inserts and a couple of items of makeup. She was so professional about it as it was usual for men to carry these items in their luggage. Anyways, once she found the moisturizer, she opened it to see that the container was almost empty and put everything back in the baggage and wished a happy journey.
Well, after checking in to the hotel, my first trip was to the nearby mall to buy stockings and boots. The boots I found were low ankle boots which could pass on as men's boot if I wore it with my jeans after the trip. I bought a wig which was easy to find as halloween is around the corner. The SA at the checkout probably put two and two together, stared at me momentarily but didn't say anything. She didn't look very friendly anyways.
I waited until evening to step out to the nearby Dress Barn. I wore women's boot cut jeans over the stockings with the new boots, women's turtleneck over bra and short sleeve t-shirt and wore a women's trench coat without buttoning it and the belt hanging on its sides. I was presenting rather as androgynous without makeup or a wig but with a cute women's hat and gloves (it was near freezing outside). It was also obvious that a woman would notice me wearing women's clothes but guys wouldn't care if I passed them by.
I parked in front of the store. It was a weekday so the store seemed pretty empty. I waited for a few minutes to calm my nerves and walked in. The door chime made me nervous but then again I reminded myself to calm myself down. The SA greeted me and asked if she could help. I said I was looking for a particular dress I saw online. She said that they probably didn't have any matching the description I gave. I asked if I could just look around at the dresses. She asked me to find her if I needed help and I said sure. I found two sweater dresses that I liked and when the SA came around, she asked me if I had found anything. I said I like these two holding them up. She asked if I would like to try them on and I responded, "Can I?", with a subtle surprise. She said, "Absolutely!", and walked me to the dressing room at the back of the store. The two other women in the store were browsing earlier but had left by then. The SA assured me that I was the only customer in the store and I could even come out to look at myself in the larger mirror if I wanted to. While I was trying on the dresses, the SA asked me if everything was alright and if I would like a different size or something different.
After trying on the two dresses, I made my pick and walked out with her to the checkout counter. In the meantime, another customer came in to pick up the dress she had asked the store to hold for her, the SA politely asked her to wait until she checked me out. The SA quickly changed her tone and said while I signed the receipt, "Sir, I hope your wife would love this dress for a birthday gift. She can always exchange it for a different size if the fit is an issue." I thanked her and left.
It was my first experience trying on something at a store before buying it and I loved every minute of it. I have bought several women's clothes both for my SO and myself but this was an entirely new and a pleasant experience for me.
(...to be continued)
