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.

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 🙂

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casey Hermoinedonna misteriosaPatsy JennusaithShae GuerinJackieOhNo Recent comment authors
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i remember the frist time was in bathroom was drying up after bathth when i leand up aginsth my sisters full slip hanging on the door i was in 7 heaven that was when i was three years old 77 now wish i could become a girl still in closettlove


Hi ya’ll. Just joined

Stephanie Q

I went through a lot of the same same issues buying clothes on line. Knowing your measurements and checking them against the clothing size charts is crucial.

Good that you mentioned controlling credit card spending. This is a trap for a lot of people.

skippy1965 Cynthia
Trusted Member

JEssie, Great article! Wait til you have an other 30 years as a CD as I do! LOL 🙂 Since I Work during the day I Rarely SEE the deliveries as they are dropped off but let’s just say that I keep at least two jobs secure-the FEdex Driver and the UPS driver! Shopping in person is even better but I LOVE AMazon Prime!! One other cautionary note about sizes is that EVEN IF you know your correct sizes, you need to be ESPECIALLY careful when ordering from Chinese companies as they usually have their own size charts that are… Read more »

Jenny Angelique Sanders

oh that is so true the chinese companys just want money no matter how they do it. even recently I got bambozeled again because of a app one of them had the app made it too easy to grab money for an order so now I have another dress comming that even twiggy would have to shrink to fit into. the better experence is just go out and shop spend money in american business instead of these companys.


Thanks for your article Jessie. I really enjoyed reading it. I’ve only ever ordered a few things: pair of shoes, a dress and some makeup. I find that shopping in person is the absolute best way to shop. And I do it dressed in my man clothes. In all my years shopping, I only had one checkout person give me an odd look. The best way to start shopping for female clothing is to shop just before Christmas and Valentine’s Day. Most sales people just figure you are shopping for your wife or girl friend. Even strike up conversations with… Read more »

Patty Phose
Trusted Member

I’ve been wearing stockings and pantyhose since I was 4. They were gifts and hand me downs from female family members. At 13, I began buying my own.

When I began cross dressing seriously at 18, I went to stores and thrift shops and bought my own clothes. I shop online too but I still enjoy looking for bargains in stores.


Hmm I cannot remember when I first dressed up but my sister’s room was so good to me when she was out with her friends. It became mine for an hour lolol

Carmen Andrea

I started crossdressing when I was maybe 5, I used to like applying lipstick and trying my mother’s high hill shoes, even though they were too big for me. Anyways when I was in college I used to rent a small studio apartment built in the basement of this house and that gave me the freedom to order by mail (the internet hadn’t been invented just yet). When women’s clothing started arriving at my apartment, my landlord started to get suspicious of me. I didn’t do it a lot, however female catalogs with my name on it started to arrived… Read more »


Thank you for sharing your experience. I started dressing when I was 5 – got caught trying on my mothers slip. I too love Amazon prime. Buying clothes in person is more likely to get you exactly what you want but coming home to a box at your door and opening it feels kinda like Christmas!


I can’t wait to start sharing some of my stories on Cross Dresser Heaven.its a SafeHaven. I’m in the middle of moving right now,but will have time in two or three weeks to share.im moning to DaytonaBeachFla. I started at age 62 or so,did it for Haloween.my wife was a blessing,she went along and helped.she sold Avon so I had the help with makeup…we went to SalvationArmy for my clothes.Even with her encouragement and help I thought everyone would judge and ridicule,that is ego. Two of my favorite places to shop are JCPENNY and Sudenly Femme. My favorite person at… Read more »

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