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.

7 thoughts 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

  2. Hi. Nice website, came across it by accident. I do not consider myself a crossdresser (not that I am against it, actually I have no problems with it), but I do wear gals clothing as a guy at times. Since I was a teen I have worn gals shoes, mostly flat sandals, until about 25 years ago. That is when I made the jump to wearing gals heels and never looked back. I regularly wear heels, love it and have never had any “issues.” Gals sandals are just so much nicer than boring guy shoes. To compliment the heels, I paint my toenails and wear gals “jeans” quite often as well. Even though they are gals jeans, the pants do look “unisex” and are amazingly comfortable. So, am I a crossdresser? Maybe? Partially? I dunno, and really I don’t care, it is something that I do and enjoy. Not sure why and maybe never will find out and that’s OK with me. Have fun. sf
    t cate

    1. Thank you for your comments and story. I have also been wearing gal sandals and jeans in public a lot more lately. I agree that both are more comfortable and definitely more fun.

      As far as being a crossdresser, I would consider you to be one. The definition is one who wears clothes normally worn only by the opposite gender. So wearing jeans, sandals and heels, in itself, is crossdressing, even if you aren’t wearing other items such as dresses. I guess that if wearing women’s sandals by men becomes more mainstream, those sandals would no longer be considered crossdressing.

    2. Just do you, no need to worry about labels, At this juncture.
      Feminine attire is just better. The way it caresses the body It’s just a wonderful experience.

  3. I’ve been a crossdresser since I was about 16/17 out of curiosity at 1st & your write ups has given me food for thought especially this 1 on confidence, as I am naturally shy my predicament is I’d love to go out dressed for 1 or 2 reasons really, the odd thing is that when I’m wearing a miniskirt & high heels, I feel like I’m a totally person, I feel much happier & less anxious with my inner feelings as I have very feminine thoughts but lack the confidence to step out of the door, I was once caught by my older brother wearing a little black dress & 4″ black patent stilettos with my hair done in a very feminine style which I have purposely grown more than shoulder length, I’d even gone to the bother of putting on false eyelashes & painted false nails matching the colour of my lipstick, after he’d stopped laughing he actually paid me a huge compliment by saying he would try & get a mate of his to take me out one night as 4some with his girlfriend if it would help me after I’d told him why I cross-dressed as it would fun if he didn’t tell his mate I was a guy in a dress, but sadly I’m still waiting, he said he been watching me for while & had seen me in my black lace top stockings & sexy lingerie whilst sat at my mother’s dressing table doing my makeup & he actually said I was just like his girlfriend getting ready as she always did her makeup whilst sat in her lingerie, I told him zipping & unzipping my dress was the awkward bit not having a guy to do it for me & he just laughed & anyhow I think I’ve rambled on enough & thanks again

    1. Dear; Rachel sweetie. I don’t not even a little bit consider your comment ramblings. It was very lovely to read. I admire your strength & courage I too am very shy especially when it comes to these matters, I need guidance myself. ⚧ I wish I had a family member or somebody close that I trusted such as your brother to help me along the way.. 🌈💜👌🏻

  4. By the way; certain Items / garments that are linked with femininity today where originally invented for men to wear a long time ago. Stilettos = Were meant to aid in the riding of a horse & tights= was utilized in military service.
    just to name a couple🏳️‍⚧️🆗
    I am really enjoying reading this website💜‼️ Thank you Sami!

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