I was 13 when I first started fully dressing up. I was also 13 when I first thought of ordering my own clothes, that would be mine and only mine. Unfortunately, I was only 13, so I had no job or money to order clothes with. Nor did I have a credit card to order these clothes on, and I wasn’t going to ask my parents (I wasn’t out to them yet). So, my dream of ordering clothes stayed that-a dream.

I had just turned 18 when I got a credit card. My first thought was “I can order anything I want!” Then, I realized that I really could.

I ran over a few roadblocks when I actually started to order, however. I was horribly mistaken with the size of women’s clothing, so I had to spend time learning what shoe size I was, dress size, how big this had to be, how long that had to be, etc.

I do remember the excitement of seeing the first thing I ordered- a box with my name on it, just sitting out the door when I came home from my job at the time. I brought it into my room and opened the box up, and there it was- a black shirt I could honestly say was mine.

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It became a bit more of problem when more boxes came and I had to hide it from my family. Sneaking into my room with a box looks fairly suspicious and especially when someone found the boxes first. I had come home to find a box on my table with my name on it. I panicked and thought “Did anyone open it? Who brought it inside? Do they know?”

I eventually ordered enough things where the delivery man knew our house, and every time I answered the door it was the same thing, “Oh I guess my mom ordered some clothes, thank you,” then closed the door and rush to my room in excitement.

I kept one of the boxes that the clothes kept in for my makeup, which also started coming in. I ordered from various websites and made sure to always order things that weren’t too expensive, and after that big rush of clothes and ordering, I laid low for a bit and enjoyed my clothes.

I haven’t ordered that much since then, but my most recent order was some black leggings about a month ago. I found them on a website and instantly knew I needed to get them. They came in and wow! They were great.

The biggest lesson I learned from shopping online is to watch your spending. If I ever bought something from a store, I would probably use paper money just to make the money seem more “real.” After my first big buy, I needed to work for a while to earn that money back. It’s just one of the things I need to remind myself, before I get carried away buying too many shoes.

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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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Shae Guerin
Shae Guerin
6 years ago

I shop in person and try things on, whether in boy or girl mode. Store staff is always positive and helpful. Consignment stores love us! But if you’re unwilling to try on what you want, you can always remember sizing: hold a skirt, underthings, whatever of yours that fits, in one hand, and draw the other end up your arm. That’s your size, and now you just match up what you find in the store. Eventually you’ll learn what works.

Patsy Jennusaith
6 years ago

Are you serious?! You ordered clothing that came to your location when you where still living with your parents? Oh my gosh! Don’t worry, I’m not being condescending, I’m impressed. I have packages come to my door to. I have roommates but it’s easier to get roommates to mind their own business than family members, especially parents. Although I have a made-up story about what I ordered each time a package comes just in case they ask but they never do because roommates tend to respect each other’s privacy, and mind their own business. Even then I don’t order too… Read more Β»

donna misteriosa
6 years ago

I recall the first time (around 8yrs old) I wore my mother’s girdle and pantyhose, the excitement, look and feel was amazing, been hooked ever since. Back then there was no internet/online shopping, only the Sears catalogue. I did not need a credit card when placing an order, I just paid cash when picking up my purchases at the Sears counter. Catalogue shopping made it a little easier to shop, however there was still the hurtle of phoning in my order and having to speak with the female order person. My heart was racing when I placed my first order.… Read more Β»

casey Hermoine
6 years ago

JC Penney and Walmart both have store pickup. You order online and pickup at the store.
You are right about the sizing, especially at Walmart. I have learned to order a XXL instead of an XL etc.

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