Crossdressing in a bar

I had my first experience being dressed in public !!! And it went great. The day started out by first doing a little clothes shopping with my wife. We went to a Ross’s clothing store and after picking out 10 dresses off we went to the dressing room. After trying on all of them, I finally decided on 2. A knee length black lace dress with shear sleeves (It’s the one I’m wearing in my new pic) and another knee length navy blue one with flared sleeves. Never thought shopping and trying on clothes could be so much fun.

Next we drove out to meet with a Crossdresser Makeover specialist to teach me about putting on makeup and helping me with walking in heels and so on. She also supplied me with a wig and a set of breast forms. After getting dressed and made up we took off for a night on the town (Palm Springs, CA) a very friendly city as any of you know who lives out here in Southern California.

We first went to a gay bar for a drink (which I needed) where we met a very friendly gentleman who we had a nice conversation with. The whole time nobody was looking at me in any weird way ( a big relief) The bartender even asked what we ladies would like to drink. My nervousness stopped and I was able to relax knowing that I could pass. My spirits were soaring and my confidence growing.

This was better than I ever thought.

After drinks we went for dinner (another big test) being in a crowed restaurant. And again no stares and everyone treated me like a lady. A man at the table next to ours even raised his wine glass to me. After dinner I wasn’t ready to go home, so we went to another bar and had the same great experience.

As we drove home I now had the confidence knowing that I could pass not only in a gay bar but also in a public place like a very nice restaurant. I can’t wait for my next night out as Helen. Before I end this, I have to say that I could not have done this without the love and support of my wonderful wife.

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I'm 65 and after years of dressing in private, I am finally coming out of my shell. All it took was losing over 60 lbs. and shaving my beard of 30 years. I've been out in public many times and even gone away en femme for a weekend. I am getting more and more confident every day. I am at the beginning of my journey

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Luanne Pham
4 years ago

Wonderful first time experience Helen. Just like you my first time outing was a nervous wreck experience. Thanks for sharing with us, since we all need to learn from each other experience.

4 years ago

A wonderful story Helen. That ‘first time out’ is so much easier when we have the support of someone close. I am glad that your wife is onside. What a source of great inspiration you have in her.

We look forward to hearing of further adventures.

Rosaliy Lynne
4 years ago

great story and love that it all went positively for you. That your wife is supportive is a big plus. Good luck in your future. Hope things always keep getting better for you both.

4 years ago

Excellent night out!! You seem to have done everything that worked well for you and your wife. Bering confident in your ability to “pass” in public is paramount, but it is how you feel at the end of the day. Go girl!

4 years ago

Loved the story. I know that it was a exciting time for you. Maybe now that you know that you can pass you will be able to enjoy going out a lot more.
Good luck and stay safe

4 years ago

I love first time stories.i didn’t xdress until I was 60 or 61.that time was Haloween.i said to my wife I’d like to wear a dress for the costume.i didn’t want to look like a dude in a dress,wanted to be believable.She helped,actually didn’t help but did all the preparations.Picked out a pretty blue dress,jewelry,makeup,panties,panty hose.iwore sandals that first time.some male friends didn’t recognize me,and we are sober people in wife said I changed into a nicer caring person that day after 30yrs together!!!! The next thrill was daytime dressing.i would go to my therapist dressed up once in… Read more »

Patricia Marie Allen
Patricia Marie Allen (@triciaxd)
4 years ago

OK, I’ll admit it, I’m jealous. While my wife tries, she has a hard time with anyone, even strangers know she’s married to a cross-dresser. I’ll have to write about my first time out sometime. Looking back, it was funny.

My wife is coming around. I do have a story regarding her and I going to the Oregon Aquarium with me wearing some obviously women’s clothes and make up, that I’ll have to share sometime soon.

Ashley (@sexyashley)
4 years ago

Congrats Helen! That’s such an awesome story… So happy for you!

skippy1965 Cynthia
Trusted Member
skippy1965 Cynthia (@skippy1965)
4 years ago

Congrats HElen! What a wonderful experience. CAn’t wait to hear of your SECOND time!

Samantha Jane
4 years ago

Great story Helen, thx for sharin. Sounds like a wondeful evening, and def makes me feel i am makin a good decision about movin from the Northeast. Not West coast, cause not a warm weather gal, buy Northwest. U did the right thing gettin made up for the first time, i would rather someone help so can make sure i look good. 🙂

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