I changed into my black top and striped chiffon skirt and then applied my makeup. I decided to keep my makeup more natural and understated for my first time out. The crowning glory was donning my wig then a final brush. My transformation was complete! Staring back at me in the mirror was Stephanie. I texted Andrea that I was ready and spent the next few minutes pacing up and down in my room until there was a gentle knock on the door.

I opened the door and Andrea was standing there with a big smile on her face. She came in, we did the hello’s and Andrea asked if I was ready? I said yes and we started the short walk to the restaurant and bar – as we walked all I can remember was how good it felt to be Stephanie out in the open again.

We entered the restaurant and headed to the bar where we found a few other patrons. The bar attendant greeted us warmly, we ordered our drinks and headed to a nearby table. It felt strange that we have been friends for four years, but this was the first time we had met in person. But we felt so comfortable together and chatted like very old friends. It was fabulous!

Whilst enjoying our drinks we had a visit from a lovely waitress who Andrea already knew from a previous visit. Her name was Kate and she was so pleased to see us. When she discovered we would be eating in the restaurant that evening she insisted on reserving a table in her area especially so she could wait on us. It was SO sweet of her.

We finished our drinks and returned to our rooms to freshen up and change for dinner, our table was booked for 8pm so there was no real rush . The thrill of knowing I would soon be eating in public as Stephanie for the first time ever was starting to kick in. I changed into my burgundy dress (which I’d chosen for this special occasion), made some subtle adjustments to my makeup by adding a bit of blush to my cheeks and touching up my mascara and lipstick.

Andrea arrived and we headed to the restaurant and were greeted by another lovely member of staff. She must have been expecting us as she knew we were to be seated upstairs. She escorted us through the full restaurant to a set of stairs that led to an upper floor where our table was. This was the only moment that I felt exposed, but I kept my eyes ahead, trying not to make eye contact but by the time we had reached the stairs I was actually enjoying the attention!

The lovely Kate greeted us at the top of the stairs (making us feel very welcome), seated us, took our drink and dinner orders and allowed us to relax into our evening.

Throughout our meal we just chatted about our dressing journeys and CDH. Andrea talked about the blog she writes and her latest post about bra’s. I talked about my year including going out as Stephanie shopping for the first time, my makeup lesson and coming out to my family and friends. It was a fabulous evening just being there as our feminine selves enjoying each other’s company and stories, and Kates regular visits to our table to check if we were ok. All of these things were priceless and made the whole evening so enjoyable.

Towards the end of the evening Kate kindly took a few photos for us. It came as no surprise that we were the last ones to leave the restaurant, As we left we had such lovely goodbyes from the staff, especially the lady who had welcomed us earlier. She was also keen on inviting us back and we promised we would return sometime in the autumn. We both left felling very contented, I was just over the moon at the whole experience which was made so much better by the warmth and kindness of the restaurant staff.

After a good nights sleep I woke feeling refreshed and excited to be heading back to the restaurant for breakfast. I dressed in a casual black top paired with a pair of stretch jeans and my nude kitten heels . My makeup was minimalist with a hint of foundation, mascara and a touch of lipstick.

Andrea met me wearing a lovely silver top and floral skirt and we headed off to breakfast. After the fabulous day before I was feeling more confident and relaxed going into the restaurant, which was much quieter than it had been the previous evening. We were greeted by another lovely staff member and made our way to our table. Everything felt so normal and if anyone took any interest in us, I am not certain I would have noticed or cared.

We ordered breakfast and then went to fetch a cup of tea. I was just about to head back to our table when I heard a young couple behind me chatting. I heard her say (probably louder than she intended) “see I told you so”. This comment was obviously confirming to her partner that I WAS a Crossdresser! When I heard this comment, I turned and looked her straight in the eye and gave her my best smile. I have never seen anyone blush as quickly as she did but she did manage to return the smile. We chatted over breakfast about the previous evening and how perfect it had been and the fantastic staff. We also talked about arranging another visit later in the year and hoped to fix a date sometime in September.

After breakfast , we went outside and found a great place to take a few photos of each other before we departed. We headed back to the hotel still chatting about how fantastic our time there had been, and all of a sudden we were at my door and it was time to say our good bye’s. We said farewell with a hug and a kiss on the cheek. All that was left was to change back into drab, pack and checkout.

Without a doubt this weekend was the best one Stephanie has ever had and one which she will never forget.I must thank Andrea for making this dream come true.

More Articles by Stephanie Aston

View all articles by Stephanie AstonTags:
5 2 votes
Article Rating
Notify of
Inline Feedbacks
View all comments
Fiona Black
Trusted Member
4 months ago

Thanks for filling us in on your wonderful outing. I love reading stories about ladies who are out and about and enjoying themselves as you so obviously did!

Sarah Kanter
Trusted Member
4 months ago

What a great evening, and a great outfit!

Trusted Member
4 months ago

Such a inspirational article about two lovely ladies getting together… thanks for sharing.
I hope I can experience the same….

Angela Crosse
Trusted Member
4 months ago

Have you returned from Cloud 9 yet? Seriously, that’s a wonderful story, hope your feminine world continues to expand xxx

Kerri Smith
Active Member
4 months ago

What a wonderful article. After the last year. Of discovering my femme self, I could see me doing something similar, just need to find a girlfriend willing to be my wingwoman.

Jessica-Renee Delorme
4 months ago

Hi Stephanie,
The story of meeting with Andrea sounds absolutely delightful and magical! I have often wondered what it would feel like to meet and spend a weekend with a CD friend and your experience really gives me insight into what it could be. Thank you for sharing.

Ashley Konners
Active Member
4 months ago

Such a great experience for you both. I’d love to do something like that and have talked about this with my wife and sister in law.

Danica Daroy
Trusted Member
4 months ago

YES……… What a great article Stephanie!!!❤️ Both of them. (Pt. 1 and 2) It’s just so wonderful that you can be Stephanie and not feeling the insecurities with your family folks. Nothing better than the support from loved ones!!❤️❤️ And being able to share yourself with another CD friend, and make what I know was a fantastic experience rubbing elbows with the public. I really appreciate you sharing your experiences with all of us, and will continue to do so!! You’re very inspiring to us all Stephanie. ❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️❤️

Last edited 4 months ago by Danica Daroy
Marie Chandler
Trusted Member
4 months ago

Thanks for sharing, Stephanie. I’m so happy for you! Sounds like it was the perfect experience and there really is nothing like sharing those experiences with friends. I’ve been out solo and with friends and friends make a HUGE difference. Another successful, inspiring CDH story.

Active Member
4 months ago

Can you share Andrea’s blog?

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.