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! 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.

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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 🙂

Latest posts by Jessie K (see all)

  1. Leonara 1 year ago

    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

  2. Kim 1 year ago

    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

    • Amanda Patrick 1 year ago

      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.

  3. jazmine 1 year ago

    I remember that feeling of buying the first pair of heels still get it after all these years

  4. MacKenzie Alexandra 1 year ago


    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.


  5. Patty Phose 1 year ago

    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 at 18, I bought most of my clothes. When I saw something I wanted, I bought it. It was not unusual for me to buy a dozen pairs or more of pantyhose at one time. Now it wasn’t unusual for me to buy several dresses, bras and panties in one shopping outing.

    I don’t know why I’ve never been nervous about doing this. I’ve purchased lots of clothes for girl friends and my wife. So buying for myself was just like buying for them. I have a lot more clothes than I really need but if I see those sexy shoes, pantyhose, panties and bras, or dress, I just have to have them.

    I enjoy the experience of buying them and love the experience afterwards of wearing them. Maybe it’s the enjoyment of those experiences that overwhelms any concerns someone might notice me buying a lot of women’s clothes and thing they are for me. And if they do, who cares?

    • Diane 1 year ago

      Your stronger than I could ever hope to be, I envy your life

  6. Angela 1 year ago

    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 online.
    Hugs and kisses, Angela

    • Jessica Cross 1 year ago

      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

      • Angela 1 year ago

        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

  7. 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 favorably.

    Have fun with it hon. Crossdressing is a joy!


  8. Khloe West 1 year ago

    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 an utter fright to have a man like anything femme ~ right? 😉

    I was thrifting one afternoon and had chosen a handful of lady dud’s that suited my tastes, when another woman in the same aisle said to me “you have a good eye and fashion sense. These are for you, aren’t they?” I replied in the positive and asked her what led her to that conclusion.

    She replied that she was there buying on hunches for lucky eBay reselling, fancied that she had an eye for fashion, but could “see” me wearing what I had hanging on my arm. “Out” shopping just got easier.

    Another exhilarating and terrifying moment of life that played out utterly to the good. Many of the folk in that store “know” over the years and chat me up about my purchases.

    Just this eve? Played a musical gig for a local cancer support group holiday event. Black men’s tux shirt on top, women’s red pants, gray glittery belt, and mid-calf high heeled boots on the bottom. One of the volunteers “got” the boots and loved them.

    Mix, match, and be brave! As fearful as it starts? It gets easier each time.


  9. Jayme jules 1 year ago

    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.

  10. Sylvia Schmidt 1 year ago

    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~

  11. Phreida 1 year ago

    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 .

  12. skippy1965(Cynthia) 1 year ago

    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!


  13. Lea 1 year ago

    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.

  14. Janine 1 year ago

    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

  15. Nicole Beckermann 1 year ago

    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!!!

  16. Dani 1 year ago

    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.

  17. Roxanne Hale 1 year ago

    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!

  18. Kim Cummings 1 year ago

    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.

  19. Zoée 1 year ago

    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 them on and need to understand what sizes you have…

    So the other day I was in my new one piece combination bought online, and despite the fact that it was (and still is) a very pretty combination, I felt like I needed to have proper women shoes to feel completely feminine.
    So I plan to go on a shoe shop just down the road where I lived. I spent a whole day to convince myself of going and went there the next day. When I finally left my place and enter the shop, I tried to see how many people was in the shop and seeing that there was too many people, my courage left me and I left the shop empty handed.
    But then I decided to go in it again before the shop’s closure, firmly confident of doing what I really wanted from years.
    I stood outside the shop trying to find something to say to the shop-girls knowing I would definitely need their help. In 2 minutes my plan was done ;I will say to them that I need high heels shoes for the birthday costume party of my best friends… (obviously, it was a lie).
    So I enter the shop resolute, but convinced of committing my social suicide. There were two shop girls talking to each others and one client. I went straight to the 2 shop girls and said my story looking at them straight in the eyes without any blushing of my part ( ,which I normally always do in awkward situation).
    The interesting thing was that the 2 ladies didn’t seem surprised at all and tried to help me the best they could. They were rather professional.
    Alas in the end I couldn’t find any shoes that would fit my big feet. But I didn’t let it wear me down. I asked the ladies where do you think I can get high heels shoes for my feet’s size. They answered me and told me something rather funny, one of the shop girls said “when you’ll find your high heels shoes just go and pay us a visit in them, you know, you might actually enjoyed it… there are women who wear men shoes so it wouldn’t be a big thing to see the opposite!”
    I laughed and say to them; “count on me, I will pay you a visit in it, it will train me to walk in it!
    They smiled, I left.
    here was another ordinary day for those shop-girls whose job is to just sell shoes to anybody interested in any of their articles.
    In the end, the lie I told wasn’t for them, it was for me, they couldn’t care less about the why. The worst enemy is often ourselves…
    I do not have those shoes yet, but will go tomorrow and I will pay them a visit as soon as I got them, for fun sake!

  20. Kim Cummings 12 months ago

    Wearing the best quality of your lingerie and high heels can be quite pricy. Human hair wigs are around 500.00 -1,500.00 .Synthetic wigs are less. Finding the perfect item in your size is a somewhat difficult pursuit. The Lingerie Dept at Fredericks of Hollywood and Victorias Secret is pretty costly. Goddess makes the most sensuously beautiful bras. Work with the help of the imported items from China, and the wholesale outlets.

  21. Charliene Gaudiosi 5 months 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.


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