Stepping Out
Today Stephanie stepped out into the big wide world for the first time.
But that’s not actually true! Way before Stephanie,35 years ago, I did venture out in a green knit dress and a pair of green suede 2-inch heels. I had no wig, makeup, or bra. When I say I “ventured out” what I mean is that I went for a very late night drive, I didn’t go anywhere, I didn’t stop anywhere, and I was back home within 20 minutes. During those minutes out I experienced so many different feelings, if you look up Exhilaration in a thesaurus, it’s all of them! Of course, I also went through all the “What Ifs” and “Maybes.” I did it, though.
I woke up this morning knowing that I was going to go out as Stephanie, and to do so in Broad daylight! I planned it like a military campaign; I knew what I was going to wear, where I was going to go, the time I would leave the house, and I had checked the weather and the morning traffic reports. I was ready.
07:30 (excitement level 5/10 – Nerves level LOW)
As soon as my wife and son left home for work I started my preparations. I started with a bath, shave and moisturise. I remembered needing to swap the cars around! Why? Because my neighbour works from home (in the front of her house) so I needed my car in a place safe from prying eyes.
08:30 (excitement level 8/10 Nerves level MED)
I sorted out my clothes (Jeans, t-shirt, coat, tan ankle boots, wig, etc.) and accessories (just my watch and rings.) I wanted to keep this trip as simple as I could. Once everything was sorted, I got dressed and did my makeup. I kept it light with just enough foundation to fill the cracks…lol. A single brush of mascara, a hint of eye shadow, and a bit of mid-tone lipstick (not too dark and not too pink). I popped on my wig and boots and headed downstairs. One final look in the mirror, fiddled with my hair, checked the back door was locked, gathered up my keys, coat and wallet, checked my hair again (more fiddling), and Now I was ready.
09:30 (excitement level 10/10 Nerves level HIGH)
I took a deep breath and (at last) stepped out the door as calmly as I could. I got into my car. So far so good. I was out of the drive and on my way. To say it felt a little strange would be an understatement. To begin with, my boots have a heel; that took a little getting used to. My breasts were nicely bisected by my seatbelt, and of course, there was this lady who kept looking back at me in my rearview mirror…lol. The plan was to take my first venture out at Windsor Great Park, due to it being only a 30 minute, easy drive. It has a good (free) carpark and some lovely walks winding their way between some of the oldest Oak trees in Britain. If you have time, they will take you right up to Windsor Castle (the Queen of England’s residence).
The drive was uneventful; yes, I got nervous a few times when waiting at lights because I feared that people would clock me! At one point, a van pulled up beside me and I knew he could look right into my car! I don’t know if he did as my eyes were locked in on the lights opposite willing them to turn green. I arrived at the carpark and found a space to park.
10:00 (excitement level 10/10 Nerves level MED)
Stepping out of the car, the first thing was taking a deep breath, I had done it! I had finally found the willpower to leave my house and venture out as Stephanie. I have to admit; I got a wee bit emotional; I could hardly believe what I had achieved, but here I (Stephanie) was standing in a carpark in Windsor. WOW is all I can remember saying at the time. I gathered up my coat, locked the car, and found a suitable path (there are paths everywhere.) I hadn’t seen anyone yet, though there were a few cars dotted around the carpark. I assumed they probably belonged to dog walkers.
I walked for around 30/40 minutes. After 10 minutes or so, I found a bench to sit on and just enjoyed the moment. The weather was gorgeous, a little mist, but the sun had broken through and started to warm things up a little. As I sat there, a couple walking their dogs passed by, (they were the first people I had seen) but stayed 30 yds away. They didn’t pay me any attention. Instead of feeling nervous, I actually got a bit of a thrill.
I continued along the path some more before turning around and heading back to the carpark. I noticed a couple of other cars had arrived, and just as I was about to get into my car another car pulled in and parked near to me. The lady driver gave me a lovely smile and a wave, which of course I reciprocated. This was the first time Stephanie had made contact with anyone! I was on cloud nine.
11:00 (excitement level 9/10 Nerves level LOW)
The drive home was uneventful; I wasn’t worried about other drivers, in fact, I really started to relax even though I was still on a high after my walk. Instead of taking the normal route home, I decided to drive via my hometown, which means driving down the high street which is normally quite slow. I’m not sure if this was bravery or bravado? I just did it and enjoyed every minute. I arrived home safe and sound, parked up, and went into the house.
11:30 (excitement level 10/10 Nerves level VERY LOW)
I had done it! I had achieved my 2021 New Year’s resolution. It may have been a simple, relatively safe walk in the park, but I will never forget the day when Stephanie became a real person in the world and not one hidden deep away in a closet.
I’m now planning my second outing (the where and when yet to be decided…
More Articles by Stephanie Aston
- Dreams Can Come True (pt2)
- Dreams Can Come True (pt1)
- Best Coffee Ever
- Standing By The Open Door And Ready To Step Right Out!
- Thank You Crossdresser Heaven
Stephanie Aston
Latest posts by Stephanie Aston (see all)
- Dreams Can Come True (pt2) - May 26, 2023
- Dreams Can Come True (pt1) - May 19, 2023
- Best Coffee Ever - March 21, 2022
- Stepping Out - October 28, 2021
- Standing By The Open Door And Ready To Step Right Out! - February 15, 2020
Congratulations, Stephanie! You did such a wonderful job of conveying the details of your adventure. I felt like I was there with you. 2021 has also been my year of venturing out during the day for the first time and I can relate with everything you said. It’s nice to know that others are sharing in the experience. Here’s to more adventures!
Hi Marie
Thank you so much for your lovely comments on my article I’m really pleased you enjoyed it. I found the whole experience fantastic and a bit scary at times but I’m chuffed that I have taken my first steps out and can’t wait for my next adventure.
of course I must also congratulate you on your adventures . I would love to hear more about how it was for you and where you went?
love Stephanie xx
Thank you, Stephanie. Here is the article I wrote after my first daytime outing ever. That was back in May of this year. I’ve been out a few other times since then. It was a very powerful and emotional experience for me. As it sounds like it was for you too.
https://www.crossdresserheaven.com/my-first-femme-vacation-part-1/
Congratulations Stephanie! What a lovely adventure. The first time out carries with it so many different emotions. I’m so happy for you that everything went well. Can’t wait to hear about your next outing!
Hi Sarah
Thank you so much, I still can’t quite believe I actually did it I’m know planning my next outing which I think will be a trip to a local department store for a bit of window shopping and if I’m feeling brave to actually pop in. Not sure sure when that will be yet but I’ll definitely post something when I do.
Really appreciate you reading and commenting on my article.
Take Care
Stephanie ❤️
Hi Stephanie
Not as brave as you. But after reading your outing I walked down the driveway to bring trash bin in full Charlotte felt nervous but wonderful.
Hi Charlotte
Well done you : ) I’m really pleased my article helped you find the courage to step over the threshold.
I really appreciate you taking the time to read my article and for your lovely comment.
take care
love Stephanie ❤️
Your article was inspiration to me
Hugs Charlotte