Crossdressing Story: Gathering My First Cross-Dressing Supplies

Every crossdresser has a beginning to their journey.

After we go through all of the reflective thoughts that help us figure out who we are, we feel the urge to start dressing up.

But in most cases, we struggle to gather the materials for our first attempt at becoming a girl.

And, of course, it wasn’t different with me.

I did struggle but never gave up, and in the end, I felt a sensation of fulfillment.

I started by borrowing some supplies from my girlfriend and my sister, but then I grew confident and bought my stuff.

It took me a while until I could figure out all I needed, but once I did, it didn’t take long to get it.

I believe that crossdressers should share their experiences, as it makes our community grow stronger.

So here’s a story about my experience with that.

1. Coming out and dressing up for the first time

It all started with a lot of reflective thoughts a few years ago.

I had just started to date my high school sweetheart, and our relationship was getting stronger.

However, I felt something wasn’t right. I always knew that I wanted to crossdress, and I wanted to tell her that as soon as possible to avoid breaking up later.

But first, I needed to figure out who I was. Well, I turned out to find myself to be genderfluid, so I opened up to her.

I won’t get into details here, as this is not the focus of this article, but everything turned out okay.

She even encouraged me to start dressing up and did my first makeup ever.

I didn’t even have any feminine clothes back then, but looking at myself in the mirror made me feel better about myself.

So, I consider this to be my first crossdressing experience.

However, I didn’t have a supply and couldn’t do it by myself.

2. Feeling the need for more

Dressing up for the first time opened up a whole lot of new possibilities, and of course, I wanted to do it again.

My girlfriend let me borrow her makeup supplies when she was around and taught me a few basic skills as well.

She even bought me a wig, as I wasn’t comfortable with my short hair while feeling feminine.

But still, I wanted more and started to borrow my sister’s makeup as well, without her knowing.

It allowed me to practice by myself and way more often. But my experience still wasn’t complete.

I wanted to buy more stuff and dress up as a woman completely.

With that in mind, I spent hours with my girlfriend looking up some stuff that I should buy, such as shapewear, breast forms, and some clothes.

We made a huge list and managed to buy some stuff online, such as my first piece of shapewear, which was a waist cincher.

But buying stuff online takes time, making it impractical if you need a lot of different stuff.

We knew I had to go out shopping downtown as soon as possible if I wanted my stash of crossdressing supplies.

But still, I wasn’t confident enough.

3. Getting confident

It took some time, but I decided to go out and buy myself some feminine clothes and makeup supplies.

I and my girlfriend had planned on meeting and the town’s main street, near the commercial district.

Having a feminine company makes it a lot easier to build up confidence and enter stores to buy women’s items. And so I did.

We went to a few department stores, and I bought the basic stuff, such as pantyhose, wig caps, and makeup brushes.

Then I got some foundation, lipsticks, and contouring powders as well.

My girlfriend gave me an eyeliner pencil and an eyeshadow palette. But I still had to buy myself some clothes.

So we went to a few other stores that specialized in it.

I wasn’t as confident as to buy some panties, but I managed to purchase a bra, a black skirt, and a grey blouse.

It was a thrilling experience, but I calmed down along the way.

I had noticed that no one even bothered to ask me why I was purchasing women’s clothes.

All they wanted was to profit off my purchases, so there was no point in making me afraid to buy this stuff from them.

I guess most stores think like that, which is a good thing for crossdressers who want discretion.

4. Hiding everything I bought

When I got home, I was lucky there was no one around.

I got an Uber and arrived with a few bags full of stuff I had just bought.

If my parents were there, they would ask a lot of questions.

But they weren’t, so I got an old backpack and stuffed my new clothes on it.

The wig was a little more complicated, but I ended up putting it into a cardboard box to protect it.

The makeup, on the other hand, was fairly easy to hide in plain sight.

I kept it in my closet, and whenever someone asked for something, all I had to do was say it belonged to my girlfriend.

It started as a slow process until I had enough confidence to buy all I needed at once.

The support from my girlfriend was quite valuable and helped to push me into my current life as a gender-fluid crossdresser.

Thanks to her, I could go out and buy all the stuff required to gather my very first crossdressing supplies.

I use some stuff I bought back then to this date, and I consider it to be one of the most important moments in my life.

Well, I hope my story was interesting, but I would love to hear about your experience as well!

Leave a comment below and tell us about it!