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. 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.
Congratulations !!!! The hurdles will only get lower and lower for you . The best part is with the hurdles getting lower you can wear higher heels and eventually there will be none . I wish you all the best and Happiness along your new journey .
Congrats Jessie! I remember my first time going out and was amazed that there were no thunderbolts raining down from above,the ground didn’t swallow me up and there were no angry villagers with pitchforks chasing me. May you have many more normal uneventful evenings out where you can simply enjoy being you!
Cyn
Congrats Jessie! This us truly a step towards a whole world if shopping, trying on clothes and shoes, and building confidence in just being yourself. Enjoy the new opportunities that unfold.
Jessie congrats on your stepping out and buying a new pair of boots that you like.
Like some of the other comments here I think that Payless stores have quite a variety of larger size women’s shoes and boots
I’ve been to Payless stores and have never been questioned about anything I’ve been looking at or buying
I’ve been to their stores as a male and dressed up as a female.
Either way it was a good experience without any questions.
Good luck in your future purchases
Congratulations Jessie!! That is a great step! Now I give you the next challenge: go to a store a say to the salesperson that it is for you! I did it twice last week, in drab, in the open. Both saleswomen giggled at first but were super helpful and professional. They want to sell, no matter to whom. What i learned through expensive trial and error is that you have to try them on at the store. Again super congratulations!!!
Nicole
I have been buying my own clothes since age 13. I have been out in drab and dressed, no one cares or notices. The only embarrassment is you and what you think people see. I am now 65 and conclude shoppers around you only see what they want to. If you dress age appropriatel and dress to blend in you will be ok, so don’t fear.
So proud for you! Also surprised you had the nerve to bring them to the fitting room on your first time buying. I’ve been buying women’s clothes in person for almost two years but would never dream of trying anything on. That takes bal-, I mean, ovaries. Thanks for sharing!
High heels and sensuously beautiful legs in pantyhose go together with lingerie and other sensuously sexy pretty attire. The feeling of being in my pantyhose and high heels is a great way to be able to be myself and relax. I have been wearing my pantyhose and high heels for years. I have now become quite adept at walking in 6 inch high heels easily. The feeling of being in my pantyhose is so comfortable and I am now wearing my pantyhose and high heels everyday.
Something similar happened with me 2 days ago. I have bought many women clothes during my last 6 years but never in a proper clothes shop, always in sex-shop where for some reasons I feel myself more confident than in other places. I kept saying to myself that the guys and women working there are working in the sex product industry and that they probably see a guy like me who buy women “clothes" like something pretty mundane. But I always dreamt of having high heels shoes. And it is not something you can quickly buy, you need to try… Read more »
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