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
Good for you Stephanie, the first step is the deepest, like you we await your next adventute.
Olivia
Hi Olivia
Thank you . I’m so pleased I’ve got that first step done and I’m already looking forward to my next venture out. I’ll be sure to let everyone know all about it
Thanks again for reading my article.
love Stephanie ❤️
Exhilarating, that is the perfect term for You’re experience! So happy for you!! I Love how you’re confidence grew along the way and I’m sure the smile and wave really helped, Relaxing you and giving you that push for the drive home which was really cool!!:):) Enjoy The Next Adventure Stephanie.. Thank You for Sharing
Hi Jill
Thank you So much for your lovely comments.
As soon as I saw you comment starting with “Exhilarating” I smiled, that is exactly how I felt and I still do when I think back to that day. I can’t wait for my next venture out.
I really appreciate you taking the time to read and comment on my article.
Have a lovely weekend.
Stephanie ❤️
Have a Wonderful Day Stephani!
Wow! I love this piece, Stephanie. I felt like I was living every moment with you. So wonderful and uplifting to read. Thank you.
Hi Becky
I’m so pleased you enjoyed my article, I have to admit I was on a high for a couple of days after my little adventure.
I really appreciate you taking the time to add your comments
Hoping you have a lovely weekend
love Stephanie ❤️
Well done Stephanie!! The first time out is so exciting and full of emotions. You have taken the first step into a bigger world. I wish you luck on your next adventure out as Stephanie.
Sarah
Hi Sarah
Thank you so much for your lovely comments, I’m certainly looking forward to going out again as soon as I can, I’m hoping to stay a little more local so I can be out more rather than being in the car so much
have a fab weekend.
love Stephanie ❤️
Thank you so much for sharing this with us all, pretty lady!!!
Thanks Michelle I’ll catchup with you a bit later
love Stephanie ❤️❤️
That is a beautiful story, expertly narrated and awe inspiring, I myself am still working up the courage to go back out in public for the first time after a bad experience many years ago, back then youth was on my side so it didn’t take any effort to cross dress just pick out some clothes put on eyeliner a fun lip color and an eye shadow to match and away I’d go, until one day I went to a public event and got harassed and publicly humiliated by some jerk I figured would be sympathetic considering they were lgbtq+,… Read more »
Hi Amiliah Thank you for your lovely comments on my article. Your story fills me with sadness and I can feel your frustrations in your writing for not being able to express your true self. I spent nearly 50 years in denial and fear of being found out but finally came out to my wife (of 35 years) a year or so ago and although she accepts Stephanie is a real part of me she does not want to meet her in person which I do sadly understand. I see you have only just joined CDH which is wonderful and… Read more »
Thank you my dear it means a lot to me and my wife acknowledges that I have a different sexuality and that Amiliah is a part of me but and can exist in the world but not in any association with her or any proximity to her or my children.
Fantastic! It’s just like that on the 1st time for most of us I’m sure. As we do it more often however it really becomes so easy you don’t have the nerves but maybe some excitement. It’s so natural for me now I almost get excited dressing up as a guy!
Hi Susan
Thank you so much for reading my article and sending me your Comments, I really am hoping it gets easier, my main worry is that I stand out as I’m 6’ tall! I guess only time (and outings) will tell.
have a great week
love Stephanie ❤️
Hi Stephanie what a lovely adventure and now you have one behind you I am sure will be many more and each one will become so much easier just like any lady out and about carrying on her normal life, I wish I could do the same but for me a secret underdresser ,I do enjoy being out knowing what I have on .underneath Michelle xx
Hi Michelle
I’m so pleased you enjoyed my article and I’m hoping it won’t be to long before I have an opportunity to get out again.
We all have different levels of Crossdressing due to many reasons but the main thing is to enjoy, embrace and stay safe.
hope you have a great week and thank you again for your comments.
love Stephanie ❤️
Exhilarating and liberating, isn’t it?
Hi Dani
It certainly was and I can’t wait until the next time
Love Stephanie ❤️
you for the great story.
Hi Melissa
Thank you so much for reading and commenting on my article
Love Stephanie ❤️