Building Crossdressing Confidence

Building Crossdressing Confidence

I spend time daily reading the online forums on In my opinion, I think the participants fall into two categories: those who are confident with their crossdressing, and those who are not. I think most participants are those who are less confident. The site is a terrific resource for building crossdressing confidence, because those who are insecure can learn so much from the advice of those who have become at ease with their crossdressing.

Building Crossdressing Confidence One Errand at a Time

One of the recent ideas I really like is going on short errands. This is one I do myself, and it really does work! If building crossdressing confidence is something you want to pursue, I suggest you continue reading and give it a try yourself.

The question raised concerned the lack of purpose the crossdresser felt. She no longer sees a need to crossdress because all she does is sit in the house. The responses were as varied as are the crossdressers who write on the site.

I like the idea of doing errands for building crossdresser confidence, so I suggested:

“I agree with the others. Once the thrill isn’t there, the best thing to do is whatever you would be doing anyway. All you have to do is decide what gender you are going to present when you do it.”

Building Crossdressing Confidence One Step at a TimeBuilding Crossdressing Confidence One Step at a Time

I think many crossdressers agree that the hardest step into the wide world is the first one. For the most part, the prospect of somebody, anybody, seeing us in an outfit terrifies us. Here are a few tips for taking those first steps.

  • People are less likely to notice you when you are driving and not walking, simply because the vehicle is hiding most of what you are wearing, and most others are not peering into other people’s cars.
  • Going out at night makes it harder for others to see you.
  • To become more comfortable, take it slow. You can try going out partially dressed. For example, you can try wearing just some women’s shoes, such as flats, or women’s jeans. That way you can become more comfortable with something that doesn’t stand out as much, before you become more bold.

One of Sami’s First Times Out

My not-so-new heeled sandals for my first walks

One of the first things I did to get out the door was to wear a new pair of heeled sandals on an hour-long walk around the area. Scared, I left near dusk to keep myself as invisible as possible.

Other than making the mistake of wearing new shoes on such a long walk, it was a fun experience. I even had a college-aged female runner approach me in a well-lit section of the walk. To my amazement, nothing happened during this! It was a great experience that really boosted my confidence.

Feeling a Little Braver?

As your confidence rises, either slowly or quickly, you can start doing other errands. Here are a few I have done myself. For those of you who are feeling braver, give these a try during daytime rather than at night. I have done all of these without a problem.

  • Drop mail in a drive-thru drop box.
  • Fuel your vehicle.
  • Order food in a drive thru.
  • Do yard work in less noticable clothing.
  • Wear women’s jeans while shopping.
  • Take women’s jeans to the men’s dressing room to try for size.
  • Shop in a crowded mall while wearing women’s flats.

How Will You Build Your Confidence as a Crossdresser?

I am a strong proponent of the Power of One, which is doing one thing every day, either  related to crossdressing or not,  to grow as a person. What is something you can do today that will help you build your confidence?

xoxoxo Sami

What is something you’d like to try as a crossdresser? Do you have any hints to pass along to others?  Leave a comment.

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Posted by Sami

Sami has been a part-time crossdresser for about 5 years. Although she still has a lot to learn herself, she is enjoying teaching new crossdressers tips that will hopefully help them on their adventure.
Besides enjoying her time with her family and working as a web developer, Sami loves to travel, make home improvements, and create jewelry in her spare time.
Read more about Sami by clicking her name.

One thought on “Building Crossdressing Confidence”

  1. I forced myself to build confidence last 2 weekends gradually trying different outfits more feminine to be able to dress as I quests you could say trans woman with typical male clothes at veterans affairs when I went to work Monday my nerves were telling me not to go with breast forms but I did later in week wore womans outfit yesterday

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