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. Β 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.Β 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.

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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! 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!”

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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.


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Jessie K

I'm a 22 Year old crossdresser who started when I was 3, trying on my mom's heels when she wasn't around. I was instantly hooked and have been crossdressing since. I'd love to share some experiences πŸ™‚

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Charliene Gaudiosi
6 years ago

I started the same way, when I was 5.
I bought my first pair of heels when I was around 20. Now I am 47 married with 2 teenage sons and trying to crossdress part time but it’s not easy.


Jill Murphy
Jill Murphy
5 years ago

Hi Jesse, Great story, it is unbelievably difficult to buy in person at first but as you will find out nobody really cares these days, I am still very nervous when I shop and sometimes go around the aisles for ages before I get the courage to go and get the thing I actually want. I am living with my SO of 39 years who knows I like to dress but she does not want to participate in any way apart from buying me the occasional pair of knickers, so I mainly dress when I am travelling for work, which… Read more Β»

Jo Jo Sweet
Active Member
1 year ago

Hi Jessie, I am so glad you had a good experience on your first time out. I want to go into a shoe shop and try on some heels on the shop floor while wearing my tights and showing off my painted toenails. If I ever will ? we will see.xx

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