Weird title, right? I assure you, it makes sense. I had stuck to online shopping throughout the years because I was way too nervous to step out and buy clothes in real life. It just seemed very daunting and I wasn’t ready for that step. Â So, for years, I ordered through various websites.
About 3 weeks ago, I thought about getting a new pair of shoes. My old pair were worn out, and I felt like they weren’t really working with my outfits. I started browsing sites for stores near my area, when I remembered that there was a Target only 2 miles away. Target sold shoes. Why not go?
I had to really convince myself to go. I was browsing CDH and constantly saw stories about the first time buying items in person. I thought about it, and eventually decided- I was going to go, and I was going to make buy these in person. I collected my money and planned everything out. It was the middle of the week, so I wouldn’t have time then. I would go on the weekend. I would have plenty of time. However, tragedy struck. That weekend, I got sick, and couldn’t leave my house. So, my trip was postponed.
I didn’t even plan on going, actually. My mom was going out with friends and wouldn’t be back until late. My brother would be going out with friends until late. Everything just fell into place- I had 3 hours all to myself. I was sitting in the chat talking about this when I decided to go. So I grabbed my money and decided to walk- it was a nice night, and an hour long walk would be fine. So I started the trek.
I wasn’t dressed for the occasion. I was in boy mode- with the exception of underdressing panties. It took about 30 minutes to get there, but I was in no rush. I had plenty of time to enjoy the night. When I finally got to the store, I thought “ok, just act natural. If anyone says anything, I’m…I’m….buying a birthday present! For..my mom! Yeah, it’s my mom’s birthday soon, so I’m getting her a present. That sounds good, that’s believable.” I made my way to the women’s shoe section. I didn’t instantly dive into the aisles, despite them all being empty. There were a lot of shoppers nearby that I didn’t want “looking” at me. I walked around the aisles a few times, looking at the different sizes, looking for mine. As soon as I saw it, I walked in, instantly picked up the box, and walked to the fitting rooms.
I remember walking towards the fitting rooms. I was carrying my box, and just acting as if it was natural. One of the biggest pieces of advice I was given was to be confident. I kept my head high, and walked normally. It’s normal to see a guy just grab a pair of woman’s shoes, I told myself. And no one even turned a head or anything.
I got into the dressing room and took off my shoes, and opened the box. It was like Christmas! 3 inch ankle boots, black, with a zipper on the side. I stared at them for a second in awe. I grabbed them and put them on, stood around for a bit, walked, and sat back down. Surprisingly, they fit perfectly and felt perfect. I took them off and put them back into the box, and put on my regular shoes. Now for the hardest part- actually buying them
I walked to an almost empty register. The man in front of me had a lot of items, but he was already paying, so I had almost no wait. I walked up and all of a sudden, a man and his daughter went in front of me and talked to the cashier. The man was giving him a lot of questions about where things were, and the cashier looked fairly confused. I was happy to let the man ask his questions, because it gave me a little bit of extra time to thing “oh wow, I’m really doing it. I’m in person!”
The man left with his daughter and the cashier turned to me. I handed him the box and he started working on his computer. He was a little shaken up from the man’s numerous questions. To be honest, I don’t even think he noticed what I was buying. He just put the box in a plastic bag and took my money. There was no one behind me looking at me weird, the cashier wasn’t phased, and no one gave me any questions of why I was buying what I was buying. In fact, it went very smoothly.
I utterly felt shocked that absolutely nothing happened. I thanked the cashier, took my bag, and left. I walked back to my house- still no one home. I crept upstairs to my room, making sure no one was there and I was alone. If I was caught with a bag, there would most definitely be a question or too-and not one I could answer with “oh, you see, it’s my moms birthday”.
Luckily, I was alone in the house. I opened up the box. I had done it. The shoes were with me, they were mine, and I was there in person for the experience.
I’d honestly like to thank you all for the support and giving me the confidence to do something like this. While it isn’t hard doing the action, the hard part is getting yourself to do the action. I’m proud that I was able to have an experience like this.
Jessie,
Good for you for taking the step (no pun intended) in your purchase of new shoes.
Your experience was well written and thank you for sharing
That was so sweet. I have found a Payless store were the sales girls are very helpful in finding the perfect shoes for me. I’m running out of space in my closet. From pumps to 4″ heels they all give me that high heel high. Enjoy your new shoes! Kim
Yes Kim Payless is a great place to buy shoes. I bought my first pair of heels there this past summer plus a pair of open toe sandals. wore the sandals out on my first ever time being out in public. the staff at payless are great and eager to help you regardless who is buying the shoes male or female. that was also my first time going out and purchasing shoes for my self.
I remember that feeling of buying the first pair of heels still get it after all these years
Jessie,
I can understand your butterflies. I am still a bag full of feelings each time that I shop. I wish that I could buy shoes off the rack. Unfortunately, I am a size 12 or 13 which is not readily available in stores. I wish thee the best.
Mac
I’ve been wearing stockings and pantyhose since I was 4. At 13 I began buying my own. I didn’t have any fears or reservations about it. There was a sales lady at the local store who used to help me when I came in even though I knew what I wanted. I bought a lot of pantyhose. She asked me if I would like to join the hosiery club. I would either get discounts or after buying so many pairs I would get one pair free. Sounded like a good idea so I joined. When I began cross dressing seriously… Read more »
Your stronger than I could ever hope to be, I envy your life
Good job Jessie! I have always been to scared to buy my girl things in public but stories like yours give me more confidence. I did go to Walgreen’s the other day in male mode and bought two pair of panty hose. Nobody paid any attention and the cashier (lady) rang them up like it was no big deal. She didn’t know me so I thought to myself what does it matter if she know they were for me. I am a size 12 like MacKenzie so very difficult to find in regular women’s shoe stores so I must buy… Read more »
Angela, you might ant to try Lane Bryant, Torrid & Catherine’s, they all carry 11 & 12 sizes and the shoes & boots are usually W in width, I get a kick out of shopping there as the girls know who I am shopping for. They also let me try on the boots _ I’m a boot nut- and shoes to make sure they don’t have to swap later, they have lately, let me try on the dresses and other clothes and I have gotten brave enough to go ask them for their opinions, wonderful
Hey Jessica!
Thanks for the tip, I will try those stores! Went to Kohl’s yesterday, asked the sales girl where the dresses and skirts were. She knew immediately they were for me. She kind of followed me around and pointed out skirts, etc. to me. I had the courage to not care what anyone thought. Ended up with 2 pair of panties, 2 pair of tights, a bra, 2 skirts, 1 top and a necklace. Went to the fitting room and tried it all on before I purchased. A GREAT feeling!! Thanks again for the tip!
Hugs and kisses, Angela
Payless is great for larger sizes. Jesse – what you will find out is that the sales people really don’t care, and I think for a lot of them a CD is a nice change of pace for their day. It has to get boring to work in sales and any “different" customer has to make the job a little more interesting. I have gone shopping en femme or in guy mode, and have tried on shoes and dresses as both. I have never had a problem. You are right that if you carry yourself with confidence people will respond… Read more »
Lovely story and good on you! I can SO empathize. Despite my odd journey of the YT “drag makeover" being followed with my being good naturedly, but utterly unexpectedly, “outed" on my FIRST “girl’s night out" on my boy mode FB page? I understand those jitters for anyone. Despite my transvestism being one of the worst kept secrets of the western world, it took me a few years to become casual about it. There’s a lot of mental game that one has been taught as a man throughout the years that must be ignored or unlearned. We all know it’s… Read more »
Love that you stepped out Jessie. I have found that Ross sometimes has a good selection of size 11 and 12 shoes and they fairly priced too. I have bought a couple of heels from there and no one really cares.
Jesse, thank you for sharing your experience. The more I learn about how these things went for others, the more courage I am gaining (I think).
Hugs, ~Sylvia Schmidt~