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After the first couple of outings at the mall, I lost some of the nervousness around shopping fem clothes and started actually enjoying it. So much so, that over next two-three weeks, I visited many more stores and ended up buying nearly a dozen skirts, bra and sexy panties. I had begun to get a hang of interacting with the sales women, making them comfortable in helping me. Barring just a single occasion, I had had a positive experience in every single store.
In February, I had to travel to Texas for a two week business trip. I frequently travel for work; so this was nothing new. In fact, I have been to this particular office a couple of times before during 2011. It was a routine visit to our company's factory.
While getting ready for the trip, my newly-rediscovered love for crossdressing started picking my mind. There wasn't going to be a lot of work, so I would have quite a bit of free time on hand. I also know the town a little bit , so this was a perfect opportunity to have some fun in relative anonymity away from home. For flight, I had to pack light to avoid lugging around too much stuff. So I settled for carrying just a couple of sexy panties and one padded bra. What excited me more was the thought of putting my newly learned confidence to use and going shopping while on trip. Another rather thrilling opportunity I saw was dressing up and going out to one of the night spots.
On the very first day of trip, a Monday, I wound up the work early, and left for hotel around 4.30. I quickly took a shower, put on the red lace panties and bra I had brought along. I was not carrying any skirts or fem dresses, so just put on my guy street clothes on top. I sprayed on the girly perfume I had bought specially for this trip.
The bra I wore was a 36B size, which I had carefully selected while buying. This cup size is perfect for me; as it gives just the right amount of visibility while wearing guy mode clothes. To someone passing by, or to someone not looking deliberately at me, the 'boobs' of this size bra are not be very noticeable. But, to someone I am talking to at an arm's length, the boobs would be unmistakable. I find this the best; because it lets me go around being too obvious in a crowd; while giving the slight exhibitionist thrill of showing off boobs to people I choose to talk to.
I drove to the mall and headed straight to the Victoria's Secret. I was hoping of a empty store, but also knew that that was probably unlikely. And so it turned out to be the case. There were a bunch of teenage girls hanging around there; which meant my chances of getting to try on lingerie were very slim. I walked through the store for a couple of minutes. I got a couple of usual greetings & offers to assist from the peppy young girls working there. One of them probably noticed that I was wearing a bra, and gave me a weird look. I didn't spend much time & walked out.
Walked a few stores further down the mall & lo-behold what do I find - my favorite store Soma. This one looked a bit larger than the store I had seen in Boston. This also seemed to advertise merchandise geared more towards younger women, more in line with the Victoria's secret sexier lingerie lineup.
I walked in and saw that it was a lot quieter than the Victoria's. There were two middle aged women shoppers. What was the highlight, however, was that there were not one or two,but three sales women and all of them were quite attractive. I especially noticed a short, slim blonde who was the very definition of a MILF. Probably in her early to mid forties, she had very delicate looking features. She was wearing very a tight black sweater and slacks that accentuated her tiny but well-shaped figure. She had a not so big butt; but her boobs were on a bit larger side for her small frame. Probably a D cup. Her wavy, smooth golden blonde hair swayed around as she walked. She was wearing definitely very tall-heeled shoes that clicked as she walked, but had a practiced model-like expert catwalk.
She said hello and walked over towards me. As she spoke, I knew that she had noticed my boobs. All the same, she talked in a very casual and friendly tone. She offered her help in finding anything. I was already liking her attention towards me, so I said that I would be glad if she helped and that I was looking for a few things. I told her that I was looking for something casual - a skirt or a dress; then a piece of silk or sheer nighgown, and a pair of bra and panties. I didn't mention that it was for me. I just wanted to see where the conversation went.
She started showing me a number of clothes. This Soma store is a little different than the one back in Boston; in that this one has a bigger selection of tops and skirts etc; besides the lingerie and intimates. First, she showed some casual skirts and tops. Some of the skirts were very long, some were very very short. Nothing in particular caught my eye.
Next, she led me to a different side of store and showed me some very pretty strapless, knee length dresses. Those were all very bright colored dresses, of summer look. These were quite sexy dresses; except that being strapless, they had little use for me. They would look odd over a padded bra & no boobs ! I wanted something that could cover my bra, at least partially, and give appearance of large breasts.
I decided to take the conversation to a more personal level.
I said to her, "Well, these dresses are all pretty, but I think I don't want to look at strapless ones right now."
I paused for a second, before adding, "Actually, I'm shopping for myself. I wanted something that I can wear over ..... the bra".
I smiled and waited for her to respond. She gave me the most pleasant smile I have ever seen, something of an understanding and implicit approval. It was almost as if she was saying , "Of course , I knew that." I even thought I saw her taking a quick glance at my boobs. Maybe that part was my imagination.
She said, "No problem, I can help you with that". It almost seemed like she was actually enjoying this episode and wanted to see where things went.
She walked over towards another set of dresses nearby. These were of more silkier texture, although these were strapless too, like the previous ones.