Sonic Drive-In at Night

First Crossdressing Outing Before Diva Las Vegas – Sami’s Week

Well, it’s Friday the 8th of July. I’ve already registered for Diva Las Vegas, happening in October. I haven’t really crossdressed for a couple of years, and definitely not out in the open. How am I going to start getting ready for time out with others at Diva Las Vegas? Read about my first crossdressing outing in preparation for Diva Las Vegas.

Getting ready for Diva Las Vegas

My last article explained about signing up for Diva Las Vegas and what I have been doing prior to that. Since I’ve decided to attend Diva Las Vegas this coming October, I’ve realized that I am out of practice with my crossdressing skills. Sure, I’ve been crossdressing in the comfort of my own home, but that alone isn’t going to cut it. After all, just wearing a skirt and blouse without wearing a wig or makeup isn’t in the spirit of the event.

I’ve got some serious practice to do in order to get ready! What better way to do it by going on a Friday night outing?

Fearful woman looking out the door
Will the neighbors see me crossdressing?

Fear of the neighbors seeing me

I live in a complex of condominiums, similar to a large apartment complex. Because of this community of families, I no longer have the luxury of sliding into my car while in the garage. Rather, I am in open view when walking to my vehicle, a necessity for getting to the daytime Diva Las Vegas activities.

I have decided that the best way to become comfortable with doing this is taking a gradual approach. First I want only to get to my car, trying my best to do it when it is unlikely others are out. This means it is going to be after dark when I give it a try.

Feeling a little rusty

Since I am out of practice, I know it is going to take a lot of time to get ready. I need to…

  • Shape my bushy eyebrows
  • Have a really close shave
  • Apply enough makeup to give some semblance of looking like a woman
  • Choose an outfit
  • Attach and style my wig
  • And get the nerve to go out that door!

Taking a Few Selfies

It took me a little while because I don’t yet have a routine set. However, I think I did fairly well for being so out of practice.

Speaking of being out of practice, I’m no expert at taking selfies. I usually use a camera attached to a tripod, but this time it was just my phone. I don’t think I did too badly with the phone or the makeup. What do you think for someone who is out of practice?

Sami’s Comeback

Now That Wasn’t So Bad

It’s finally dark, and it’s time to try getting to my car unnoticed. I’ve decided to go to Sonic Drive-In, first because a strawberry shake sounds good for calming the nerves. I also get to face a carhop face-to-face, so it is going to help with overcoming fear. It should be a quick safe, and fun outing.

It took two attempts for me to make it to the car. During the first I was starting to lock my door when I started feeling really uneasy. Was it women’s intuition? I returned inside. Seconds later the family next door came bursting out of their place.

Whew! What a relief that I was right! My heart sure was pounding!

I decided to wait another half hour. This time I was successful in driving to Sonic, ordering my food, and eating it in my car. The carhop was as nice as I expected, so it was a good outing.

What Did I Learn?

From start to finish, I accomplished my first crossdressing goal of 2022 in about 5 hours or so. What did I learn from my experience?

  • I still have a lot of fear to overcome before Diva Las Vegas in October, but I am glad I took the first step.
  • I think a lot of other crossdressers can relate to the terrifying fear of being discovered doing something that much of society either frowns upon or finds to be strange.
  • Even becoming fully competent with makeup or fixing my hair won’t make me pass as a woman in many cases, but I will feel better about myself once I get better at it. I’d like preparation to be a fun and skillful experience rather than the hours-long chore it is now.
  • Most importantly, I am proud of myself for following through with my plan, rather than cowering in fear all night. It does become easier with each practice.

xoxoxo Sami

p.s., Here are some of my other popular Sami’s Week posts. Enjoy!


What did you think about this article? What would it be like for you to attend a big event like Diva Las Vegas?  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.

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