My First Dress Up: Danii Is a Lucky Girl!

Several years ago, my wife and I were watching a movie… forgot the name, but the lead actor played a crossdresser role. I casually said that I had always wanted to try that, try dressing up in woman’s clothes.

My wife never said a word, but after the movie she went to her wardrobe and put a dress, skirt and blouse, panties on the bed.

I asked if we were going out.

She said, “No. Try this on.”

I hesitated and she said, “You want to try it, so go ahead.”

Still hesitating, she said, “Dan. How long have you been wanting to try this? I would like to see you in my dress.”

So, without further prompting, I stripped down, put on her panties… and, what a RUSH!… then the dress.

Asked how it felt, I admitted it excited me.

“Tomorrow we’re going to get you a wig.” she said.

I blushed with excitement.

“A wig?” I asked.

“Yes and shoes… you need shoes.”

I objected, asking why.

“So you can dress up for me. You’d like that.” she noted, “Yes, because you would like it, I want to see you happy.”

Every crossdresser want-to-be should have such support!

Well, true to her words, the very next day we hit a wig shop on Oakland Park Blvd, I don’t believe it’s there anymore. I wanted her to pick one out she liked, but she said, “Your wig. Your look. You have to pick it out.”

I narrowed it down to three and tried each one on. I went by the smile on her face as I picked out my new wig. Then, we went to the Faith Farm thrift store and she helped me pick out my first wardrobe.

The shoes were harder to find, but we finally found a pair of sandals at a discount shoe store.

I’ll never forget the thrill of that first shopping spree!

Headed home we stopped by her sisters house. It was curious that she grabbed the bags of my things, but she had some too and I guessed she wanted to show her sister her stuff.

No. Once inside, she told her sister that I was going to show off my new cloths.

Oh hell no!

But, my wife explained to her sister we had watched a movie and as a result I thought I’d like to try dressing up.

Her sister as cool as she was simply said “OK”.

So, off the the bed room I went, and tried the first outfit on, showed it off, then the second and finally, the third.


I wasn’t even nervous. To the contrary, I was as excited as a little boy at Christmas!

I stayed dressed while we chatted. Her sister disappeared to her room a few minutes and came back with a handful of makeup. Adding to the wig, it was awesome. I was PRETTIER than I ever imagined I could look.

The two sisters bantered back and forth about how good I looked, and how making me up, made up for them never having Barbie dolls.

I was included in the conversation which became a girls night.

That was the beginning of Danii.

My very first time dressed up, made up, feeling my fem side emerge, being one of the girls…

It was wonderful!

My wife insisted I drive home the long way in my new look. Another rush being seen by other drivers, some teenage kid gave me the eye at a red light.

I found a new world.

Since then, my wife has passed away, and her sister moved north.

Luckily my niece and daughter have stepped in and continue to be my support. They both acknowledge and accept Danii, help with female tips, hang out with me.

Danii is a lucky girl!

By Danii

I have been dressing for almost 20, out for 12, not a kinky desire but who I am, I have a strong Fem side the emerges when I pretty up. I began as a sub, bottom. Recently became a switch enjoying the top, dom roll as well. I'm seeking friends. The Belles has been a great find. Although I came out prior,  Ava is filling a roll CD's need to come out.

7 thoughts on “My First Dress Up: Danii Is a Lucky Girl!

  • Danii

    I blush seing my story out to the public but then I blushed the first time that I went out in public. Guess it’s ok for a girl to blush. Hugs to all. Danii

  • Ava Durga

    Thanks for sharing your story, Danii. You’re a lucky girl, indeed!

  • BeccaCOQ

    That’s a great blog Danii. It’s so nice hearing about significant others being so welcoming. You truly are a lucky gurl. 🙂

  • Suzanne

    Great story and you are so lucky to have had such support. Enjoy

  • Jan Stevens

    Loves your story. I dont have any support to wear my lingerie. I will tell you girls my story too..

    • Ava Durga

      We’ll look forward to hearing your own stories!

  • Svetlana Brewski

    Lovely story! Good for you. Sorry that your wife passed away … but for your daughter and niece to support you —— how awesome is that! Good for you! You go girl!

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