Sissy Shopping Stories

Sissy Shopping Stories

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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.
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.
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.
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 .
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.
I 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.
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 try 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.
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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.
Read more about Sami by clicking her name.
Perhaps Ross should change their motto to: Ross — cross-dress for less. BTW , Monday is markdown day at Ross. Dressed go for mere single dollars. I actually have shopped at Ross, both in ‘drab’ and in ‘drag’. NO PROBLEMS.. NOBODY CARES. One nice young lady checkout clerk at Ross asked if I was shopping for my wife, I replied NO, that I was a CROSSDRESSER. She rather amused, so I offered a photo of myself as Velma Dinkley nee the Scooby Doo cartoons…. She was impressed.
Velma is like you, age 64.5 and not bad looking.
Last Saturday, before going to our local TG-CD support group, I visited my favorite ladies consignment store, and then went to Marshalls to shop. I encountered a tall, nice looking older woman who smiled at me and issued a ‘Hi’— You look nice’. I replied ‘thank you’ and moved on. WHATTA RUSH! I have been going out for only about 18 months, in a conservative southern state, and I have had no problems what so ever. So chill, and enjoy yoursef….. Velma
Thank you, Velma, for your comments. I have been finding what you say to be true over time. There are no problems, and people, for the most part, don’t care.
I hope others reading this article are encouraged to get off the fence and try shopping in a store for themselves, regardless of whether they do so while presenting as male or female. It is definitely a thrill to do so and “live through it!”
Sami,
I have bought bra’s from Lane Bryant and Victoria Secrets for myself. The worst part was walking in and asking for help. The sales associates were very nice and helped me find the right ones for me. I have bought a few dresses and shirts in the stores but never tried anything on. That is my next adventure. I have met a person locally that is transgender and she has offered to take me shopping. I just am not quit ready yet. Soon.
I don’t know whether this will help you, but it might help you gain confidence without going en femme.
I also have not gone shopping for clothes en femme, so I understand what you are feeling. However, I have gone shopping while drab, including trying for fit. It is easiest at places that don’t have someone at the entrance to the fitting rooms. Just walk in with what you want to try.
At those shops where someone must let you into the fitting room, you might get a strange look, but usually that isn’t the case. You probably wouldn’t be the first they have seen.
I once had a younger attendant giggle out loud, but I didn’t take it as making fun of me. I think it was how she coped with something she wasn’t expecting.
My experiences may not work for you, but I think it is a good way to ease into becoming more confident without worrying whether you have perfected your look. For myself at first, it was easiest to do with blouses and women’s pants or shorts. Now I have the confidence to try anything, including dresses.
Hi, Again it ME, Velma Dinkley (remember me from ScoobyDoo cartoons?) I would recommend you try Value Village/Savers thrift store for a first shopping adventure. There are 7 V.V’s ‘in our conservative southern town’. For first time shoppers, go on MONDAY, TUESDAY–seriously SLOW retail days.
Heres a tip when shopping size: Often the size listed on the garment is not correct-that is why it is at the thrift store! As retired engineer, I have devised a method of measuring the yoke of the dress/blouse using my outstretched hand from tip of thumb to tip of pinkie. My span measures almost exactly 9inches. And the yoke width on my size is at least 18inches. If the yoke does not fit, move on the the next garment. Even if the yoke does fit, then check for bustline fit. Same works for waist size, just watch out for the wrong hip sizes.
BTW, if you have not tried ‘gurl jeans’, you just have not lived. They AINT guy jeans, and that is a GOOD thing. Gurl jeans have a built in STRETCH of lycra-spandex that really accent curves. ‘Its a good thing’.
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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.
Read more about Sami by clicking her name.

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Are you ready to go “ Down The Sissification Rabbit Hole?” Then read this…
I t can be said that sexy lingerie to a sissy is like whipped cream to strawberry shortcake. A sissy without at least one matching bra and panty set would be like an Eskimo without an igloo. The truth is that sissies and lingerie go together like… okay, okay, enough of the mediocre metaphors.
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