Dreams Can Come True

When I joined Crossdresser Heaven four years ago, one of my very first friends was Andrea Raven. Andrea took me under her wing, and we have remained friends ever since. n the summer of 2019, we discussed the possibility of me venturing out in public for the very first time. Andrea offered a lot of advice and support, but more importantly, she never pushed and left it up to me to decide when I was ready to take this huge step. Unfortunately, COVID happened, and all plans were off which may have been for the best.

Earlier this year, in a catch-up email the topic of getting together popped up. At this point, I knew I was ready to venture out as I had already been out twice as Stephanie to a local department store. Andrea suggested that going out dinner and drinks would be a perfect start and ideal for my first ever public outing. She suggested a hotel that was close to a restaurant she thought would be appropriate.

After we had agreed the date and hotel, I set about making my booking. We had decided it would be best to arrive in drab and then change into more feminine attire. The very thought I would be drinking, eating and sleeping as Stephanie was making my hands tremble and my heart pound! The moment I hit send, making our rendezvous a reality was completely exhilarating. I sent Andrea an email confirming my reservation and soon got a reply that she had also secured her room. We were now all set, all we had to do was wait two months.

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Fourteen Sleeps to go

Two months flew by and before I knew it there were only a couple of weeks to go. I was getting very excited and began to focus on the trip and asking some serious girl questions -what to wear? what accessories to take? what to carry my makeup in? and what handbag would be best? All these decisions felt so alien. As a guy, I’m so used to just throwing stuff in a case just before I go.

I decided that my priority was to be as comfortable as possible. After some careful consideration, I decided that my striped skirt and black top would be ideal for drinks as it was smart and classy but also casual and comfy. I chose my burgundy wrap dress for dinner since it is my favorite dress so I would feel very pretty, but it’s also a lovely length that comes just on the knee. For breakfast, I decided to go very casual with jeans and a black top. Now I had to decide what shoes to wear, as the weather is now warmer, I decided that my nude kitten heel sandals with all three outfits would be perfect.

Two Sleeps to go

With a couple of days to go the excitement was growing again as it had when I had booked the hotel. I decided to spend the afternoon trying on my chosen outfits just to be sure. This of course was a lot of fun as well as being a very practical exercise since it also helped me decide what makeup I would be taking. For my nails (toes and fingers) I opted for a light pink color that would work best with all three outfits and lastly, I selected a lipstick called Neutral Rose that I would give me a more natural understated look.

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One Sleep to go

Today was all about getting the last things together before packing. The first task was to give my favorite wig a wash and condition. Next, I went through my makeup to ensure I had everything I needed. I realized I needed a makeup bag for makeup and accessories. I quickly found just the right thing on Amazon. I chose simple accessories – a couple of rings, a simple gold pendant, and a lady’s gold watch.

No Sleeps

After a better-than-expected night’s sleep, I was up early to start getting everything packed. I really loved doing this, getting out my outfits, folding them carefully, packing my makeup, wig, brush, panties, toiletries, jewelry, perfume, bras, and shoes. I checked the time it was three hours before I needed to leave, so I had a relaxing, hot bath with my favorite scented candle to help me relax. I

When I finished my bath, I had about an hour before I needed to leave. That hour seemed like days!! Eventually, the time came to start my one-and-a-half-hour drive north and after a very uneventful drive, I arrived at the hotel.

After checking in I went up to my room and sent Andrea a text just to let her know I had arrived OK. I asked Andrea if she could come to my room when we were both ready so we could go to the bar together. This would also be the first time we had met each other in person.

So, here I was in a hotel room with all of Stephanie’s things hung up or neatly arranged on shelves. There was not a sign of my male self anywhere. I stood there for 10 minutes just thinking about what had been and what was to come. I was very excited but a little apprehensive. I had come so far on this journey and all of a sudden, I was here, it was real, and I was about to transform myself into Stephanie and finally walk into a public bar for a drink with my good friend Andrea.

At Last!!


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Fiona Black
Trusted Member
10 months ago

The anticipation and excitement as you approach what you know will be a very feminine occasion is wonderful to experience, isn’t it? You look lovely, a very attractive woman. I can’t wait to read part 2.

Last edited 10 months ago by Fiona Black
Marie Chandler
Trusted Member
10 months ago

What a wonderful story. I’m so happy you two finally got to meet in person. Looking forward to hearing the rest.

Amy Myers
Noble Member
10 months ago

That was a lovely story and what a first out! I’d say you did it in style. Thank you for sharing it with us!
I’m sure there will be many more outings for you in the future.

Trusted Member
10 months ago

A true rite of passage for any cd! I’m looking forward to hearing the rest of it Stephanie.

Kim Rose
Active Member
10 months ago

I enjoyed reading that Stephanie! Hope to one day be as brave as you…. And if it makes me half as happy as you always look then I’ll be a luck lady!

Am looking forward to part 2! 🙂

Julia Navarro
10 months ago

Wow! Awesome story honey! Can’t wait to read part 2. I would love to have an story like yours one day!

Angela Crosse
Trusted Member
10 months ago

What a heartwarming, feelgood story. Great to hear you got to make the big leap in your feminine life. Here’s hoping part 2 arrives soon. xxx

Camryn Occasionnel
Active Member
10 months ago

What a wonderful story! This is exactly how I visualized my first-time-out would be. And what a lovely photo to memorialize the big event for all time!!

Looking forward to Part 2!

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