In my last post I ended it by saying that this past weekend was going to be special, and boy was it ever true.  As I mentioned in my post, Gutturball, I came out to some of our friends from Mississippi.  One of these friends, L, was very interested in what I did, and had lots of questions about how I did the transformation.  Since then, L has been interested in transforming into his feminine self.  So I invited him and some friends over to have some makeovers.

We had plans for this big day for over three weeks, and I was so excited for the chance to dress in front of others (K being the only one who’s seen Katie in person), and give a friend his first transformation.  On Sunday, we invited 4 friends over, including L and his partner T, our bowling friend M and her husband W.

As soon as they arrived to out apartment, L wanted to check out my shoe collection and try on some heels.  He did well for his first time, although it didn’t help my shoes were large on him.  Then we went through my collections of wigs, as lots of questions were asked, all of which I was more than happy to answer.

L wanted to watch me get all dressed up first, but since our bathroom is not large enough for 5 people to watch someone put on makeup, I moved everything to the dinning room.  It was actually nice to have a chair to sit in and do my makeup.  It was my first time doing this in front of anyone, and in this case there were 5 people watching me.  It was a bit awkward to begin with, but after focusing on my routine, I felt more comfortable.  As I did my makeup, I began to explain my process to L, because I would be helping him with his makeup next.

After I got finished and dressed, it was time for L to get his makeup done.  I was a bit hesitant, because I’ve only been doing makeup a few times a month over the last year and a half.  Needlessly to say, I’m no makeup artist, and I’ve only done makeup on my face, which I’ve come to know how to work with.  As I got started, I had to fix a few mistakes, and kept asking the ladies in the room for their opinion for colors which would go well with L’s skin tones.

As we got closer to being finished, I could tell that he was happy with what he saw developing.  After getting into some clothes he bought the day before, and trying on a couple of wigs, we were both happy with the outcome, especially for being his first time.  He soon found out how hot the wigs can be, especially when it’s nearly 100 degrees outside.  The wig stayed on long enough for some pictures to be taken, and some big smiles to come through.

After all the makeup, shoes, food, and drinks, several hours had passed and it was time for them to go.  We all were looking forward to Sunday, and it was not disappointing.  I got a chance to be Katie in front of others (something that was easier than I thought), and helped a friend with his first transformation.  At the end of the day, we all said we needed to do this again sometime, which I’m already looking forward too. 🙂

Have a great week everyone,



About katieinthehall

I'm a rediscovered crossdresser in my early 30's looking to express my thoughts as I move through this journey of discovery.

Posted on June 25, 2012, in crossdressing, Dress up day, Family/Friends, Makeup and tagged , , , , . Bookmark the permalink. 6 Comments.

  1. Pictures or it didn’t happen! Just kidding, you gotta respect their privacy. Awesome job! You know Katie is you because being her in front of people is not acting. It’s just being you, though a more fabulous version of you. Go Katie!

  2. Thanks Ariana! That’s a really good way to look at it. I definitely didn’t feel embarrassed while getting ready, which I would normally do if a lot of people were staring at me while doing anything, especially this. I learned a lot from this event, and I think it was just the right thing to do to build that confidence a bit higher. Having several supportive friends can make a world of difference.

  3. Wow, sounds like an amazing weekend! So cool you got to help someone else learn, which sounds like it helped you learn about yourself as well. And I agree, pics or it didn’t happen lol. 🙂

  4. Sounds like the next time we do something like this, not only will we be doing makeovers but also a photo shoot. 🙂

  5. I had so much fun and you and K are the best hostesses EVER!!!!! W wants your potato salad recipe! Katie was as beautiful as ever and L looked great! Can’t wait to do this again….SOON,

  6. Thanks M! It was a blast. Next time L wants to get dressed up, we’ll come down with all the makeup and wigs, and the recipe for the potato salad.

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