limited crossdressing opportunities

Crossdresser Shopping Trip with a New Friend
Sami’s Week

I got to do something last week that I never thought I could do in this rural part of America! No, it wasn’t tipping over a cow, nor was it waiting to pass a slow-moving tractor. No, my friends, it was better than that! I was going on a crossdresser shopping trip with a nearby crossdressing friend.

Sometimes Things Don’t Go As Planned

My new friend does not get to dress often, so when the opportunity presented itself, she was ready! She wanted me to teach her some of my makeup tricks. Unfortunately, I consider myself only a novice when it comes to applying makeup, let alone teaching someone else how to apply makeup in as unskilled a way as myself.

I later thought about something I am pretty good at doing: nail polish. So we set a date to dress en femme, meet at her house about 30 miles away, and try our hand at sharing a skill.

The morning of the lesson, however, I thought of a possibly better idea. I knew my friend did not have much of a casual clothing assortment. I thought this would be a good opportunity for us to go on a crossdresser shopping trip to a town about an hour away. By having clothes that would blend in better, we may someday be able to go somewhere together and not stand out too much. So we decided to change our plans.

Our Crossdresser Shopping Trip

Crossdresser Shopping Trip

Yes, this picture shows how beautiful and carefree we wanted to be during our crossdressing shopping trip. However, neither of us are comfortable shopping locally while en femme. We decided to present as men who are shopping during the holiday season.

We wanted to get the most bang for our buck, so we started our crossdresser shopping trip at Goodwill. I wanted to pick up a pair of old jeans so that I could work on my house without ruining my nice jeans. My friend wanted to look at dresses and shoes, especially boots. She didn’t have any luck, but I found three pairs of jeans to try. I had to get an attendant to unlock a dressing room. Two pairs were too tight, but the third pair was right on the money! Better yet, it was only $1.99. It is perfect for painting!

Even though the store had several other people shopping, we didn’t have any rude looks while two guys were rummaging through the women’s section. This is exactly the experience I have had in other second-hand stores. Everybody is too interested in searching for a great deal to care who else is there.

The Case of the Hovering Saleswomen

My friend was really interested in boots, so we decided to try Payless Shoe Source next. This place has a good choice of bigger shoes, and their prices are reasonable. The only problem is that we were the only customers in the store, and there were three saleswomen. They were overly “helpful” in that they would return about once a minute to see whether we needed help. The best help would have been for them to leave us alone!

Since I am not in the market for shoes, I tried distracting the saleswomen for a while, allowing my friend to take a look at the offerings. In the end, though, the “helpfulness” was too much. We decided to move on to a more welcoming place.

As we drove to the next store, I explained my theory that I thought we might have had better luck at Payless had we been dressed en femme. I’d be interested in reading comments from others who shop at Payless. Are the salespeople normally aggressive when you shop en femme? Leave your comments below.

Will She Succeed?

So far my friend wasn’t having success. I suggested we continue our crossdressing shopping trip at Ross Dress for Less. Although I have found them to have a good choice of reasonably priced offerings, they have a “gatekeeper” at the dressing rooms, so that person gets to see everything one is going to try. I understand they do it to cut shoplifting, but it does cause discomfort for this crossdresser.

My friend decided to look at shoes and dresses again. Deciding just to pass time looking at the racks. I found a jacket I liked. I don’t have any women’s jackets yet and have kept an eye out. The price was still too high, so I passed on it.

Moving to the blouse rack. I was looking for something that was solid and long-sleeved. I found something that I wasn’t too crazy about but decided to try it on anyway. By now my friend wanted to get my advice on a dress. She didn’t want to try it on in the store, so she wasn’t too sure whether it had a good chance of fitting. My advice was that it looked good and would fit, so she decided to buy it.

I then showed my friend what I was considering trying for fit. I said she could watch the gatekeeper’s reaction while I was taking the blouse to the fitting room. As I have experienced at Ross in the past, the interaction was one of indifference. She directed me to the men’s fitting rooms. My friend later reported that she didn’t see any problems with the employee’s reaction either.

Blue Velvet BlouseI decided to buy the blouse, blue velvet with a zipper in front. I also picked up some pretty hair scrunchies, and we proceeded to checkout with no strange looks from anybody.

Sami’s Final Thoughts

Even though we didn’t shop en femme, I thought this crossdresser shopping trip was good for both of us. Nothing bad happened, and at worst we were only irritated by the salespeople at Payless. We didn’t see anybody we knew despite the larger than normal crowds. I think there is a decent chance we’ll eventually work up the nerve to┬átry again while dressed.

I also suggest that if you don’t want to try clothing in the store, be sure to take a look at the store’s return policy. You’ll have to keep any tags or packaging materials in the event you need to return something.

During the drive back, we decided we did want to give en femme shopping a try at some towns about 2-3 hours away. Our chances of seeing someone we know would be very small then. I think that would help build our confidence.

As I said in an earlier article about facing our fears, doing things that feel uncomfortable help one grow and become more confident. This crossdresser shopping trip definitely helped with that. I think both of us enjoyed the excursion.

xoxoxo Sami

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Sami has been a part-time crossdresser for about 5 years. Although she still has a lot to learn herself, she is enjoying teaching new crossdressers tips that will hopefully help them on their adventure.

Besides enjoying her time with her family and working as a web developer, Sami loves to travel, make home improvements, and create jewelry in her spare time.

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