I often hesitate with decisions because of what others may think. In most cases that is not a reason to hold back. The best part is once I figured this out, each new “tougher” decision became easier to make.

Before 2011 I didn’t do anything much different than when I was growing up. I was always interested and curious about what it would be like to dress as a girl, but for the most part not interested enough to do more than putting on some undergarment and fantasizing. But in August of 2011 I had my home to myself for a few months and I went totally crazy. The first step was going shopping.

Breaking Imaginary Barriers

I don’t remember what was the trigger, probably the knowledge that I would be alone for a few months compounded by years of curiosity, but I made the decision to crossdress. I wanted to get anything that would temporarily transform me as much as physically possible. I wanted it all. I wanted a wardrobe, I wanted to shape my body with a narrow waist, wider hips, breasts, I wanted long hair, makeup… I wanted to learn to transform myself. Mind you that I didn’t have anything at that point. No wardrobe, no experience, and was an overweight guy.

One of the very first things I did was go to the second hand store to get myself some outfits. Oh, wow! These were some of the most powerful moments of my life. The challenge was that I had a number of imaginary barriers that at first made it hard for me to go shopping.

I was going in the store, terrified of being recognized as I browsed the ladies section. At the same time the excitement was out of this world. Just imagining a pretty girl wearing some of things I was browsing I’d get excited and aroused.

Choosing what to purchase was tough. I didn’t have the courage to go to the fitting rooms to try anything, so I was sizing things by eye. I didn’t have a sense of style (not that I have one now, but back then it was null) so I had no clue what would go with what. When I got to the till I was overcompensating my concerns by acting up as if I was waiting for my girlfriend, as everything in my basket was female attire. Even with all that hesitation and apprehension I managed to get through and bought myself a few outfits.

I had done it!!! I had gone in, browsed, chosen some things, went through the till, paid for them, and got home “safely”.

Can you imagine my excitement? The excitement was twofold. The immediate excitement was that I had gotten a few things to put on and try out. At the moment this excitement felt larger and stronger than the second excitement. The second and more powerful, life lasting excitement was that I had overcome my fears to go buy something on my own, in person, at a store. My fears were about being recognized, stigmatized, rejected, and probably even mistreated. It was a huge barrier that I had knocked out.

Next, The Fitting Rooms

In my first shopping rounds I got things that didn’t fit me or that I simply didn’t like, so I had an excuse to go back to the store to return them. It’s not that I really needed an excuse, though. I was so thrilled with the first purchases that going back wouldn’t take me long. This time I really wanted to try things out before buying them. But I was still terrified of being recognized. Just browsing was exhilarating, but going to the fitting rooms to try something out? Ok, that was a higher level of concern and excitement at the same time.

As I browsed I felt like everyone was looking at me. I had a sensation that people were staring and judging me. In hindsight there was absolutely no or little reason for my worries, though. No one really cared, and that’s if they actually noticed, but at the moment I wasn’t seeing it like that. I felt the opposite; I had this big barrier in my mind.

I had already a selection of things to try in my basket and now the hardest part was the fitting rooms. The store that I went to is a busy one. Often there’s a short line for the fitting rooms. I managed to brush off my worries and queued up. Again, I felt that people in the line were analyzing my basket full of female things, but I just kept minding my business and focused on the instructions of the girl working the fitting rooms. Finally got to the front of the line, the girl asked me how many items I had, and showed me to a vacant stall. Still shaking, I went in and tried what I had selected. At this point the worst had already passed. No one said anything mean to me, no one stared, or at least I didn’t notice. I was in, trying things out. I would imagine someone outside in the line seeing the guy going in, taking his steel toe shoes off, hairy legs, and sliding in a dress. Most likely it was my imagination, but as I thought of that I laughed to/at/with myself because that’s exactly what I was doing.

From my selection some things didn’t fit, others I didn’t like or were too expensive, so I had to return a few and keep others. When I left the fitting room I gave the employee back the things I didn’t want, but as nervous as I was as a guy giving back a few dresses, skirts and blouses… nothing happened. The employee didn’t miss a beat and of course no one said or did anything. I had just done it again! I had just knocked off another major barrier. Another very important step forward. From that moment on I was able to go to the fitting rooms whenever I went shopping.

A few months after these initial shopping trips I graduated from the second hand store to brand stores on high street. After that I was able to go in as a guy and actually ask for help from the sales girls.


A few days after I had started building my wardrobe I went and got a pair of breastforms (prosthetic silicone breasts). I drove down to a warehouse that distributes them online, got fitted, and purchased them. Just as going to the second hand store, it was a terrifying experience and super exhilarating at the same time. Terrifying because someone else, the sales lady, was going to see this guy buying silicon boobs. And exhilarating because I wanted to see how they’d look on me.

To make the long story short, I was driving back home after getting the breastforms just thinking to myself what the heck had I just done. Breastforms are not cheap, and I had just spent all this money on something that felt like an exaggeration. I felt guilt. But on the other hand the excitement to get home and try them was overwhelming. As I was having these conflicting ideas, I also thought to myself “well, you did it… What about a wig?” So before I got home I stopped at a wig store that I had already seen and got my very first wig!

Each new step was a conquest. Each time the feeling was the same, but the target had moved up. First brushing off any concerns to go buy the breastforms, and once on a roll getting the first of many wigs.


The process repeated itself pretty much for every new experience, and they were happening fast in those days in late 2011. The next one was buying makeup. If you don’t know about makeup, which I didn’t know anything at the time, it’s an incredibly large and complex world of brands, styles, kinds, colours, marketing and social engineering all mixed up in what we call makeup.

Naturally this was another overwhelming topic for me with the same set of barriers, but I went in like before. First I went to a self serve store where I’d pickup a couple of things like eye shadow and the all important lipstick. Again, I felt everyone was looking at me. Like at the second hand store the first few times, I’d overcompensate by pretending to be waiting for my girlfriend, which now I think it got me more attention, but at the moment that was the mechanism I found worked for me.

If I could talk to myself back in 2011 I’d tell myself to just go in, put a straight face, don’t say anything more than the basic purchase interactions. That way you’ll draw less attention.

And just like with the clothing, later I graduated from the self serve store to makeup stores on high street and at one point going in as a guy asking for help from the sales girls.

A Foundation

At the time I didn’t think much about these steps and their importance. They were never considered part of a transition or a larger plan. They were the natural progression of while having fun getting better at crossdressing.

I did acknowledge these first few steps were removing barriers. I now figure that the excitement was oh, so much stronger than the worries and uneasiness I had. So that excitement was the true force behind my will power to overcome any fear I may have had; to overcome those imaginary barriers I had created for myself.

As a friend told me a few months ago, there’s no second time without the first one.

Now I know and cherish that knocking down these barriers was the foundation, not only to what I have accomplished, but rather to now knowing that most barriers I have are of my own creation. As such, it’s actually not that difficult for me to break these barriers down. It still takes willpower and often some thinking, but I now manage to resolve my doubts and desires much quicker than before.

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