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.

Nature Day 3


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…


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Stephanie Aston

31/01/2022 update
 I’ve been crossdressing on and off most of my life but in 2018 finally came to my senses and accepted that there is a very special part of me that could no longer be restrained, that year Stephanie was born, gained an identity and joined CDH. Since then I have grown as a person and blossomed as a woman. In 2020 I finally came out to my wife, at the time it was very stressful but she has accepted that Stephanie is a real part of me. Both of my children (25 & 22) also know about Stephanie and took the news very well. Unfortunately COVID cost me my job so I now class myself as early retired but the up side of this is that I now have more opportunities to be Stephanie. During COVID I managed to lose over 45lbs in weight which has really made a difference to my (and Stephanie’s) health and well-being though over the last few months I’ve put a few pounds back on so have now joined a gym to rectify that ASAP. In 2021 I took my first ever steps out into the world with a walk in a park (please read my article) and I’m planning on more adventures this year gently expanding my horizon’s and building my confidence. 4th Feb 2022 update…. Went out shopping as Stephanie for the fist time and it was glorious……. 13th March update…… Today my wife and children met Stephanie in person for the very first time. Everything went brilliantly and they had nothing but love and praise for Stephanie. It has truly been a monumental day : ) April update…… I have now told my Mum and Dad all about Stephanie and they took the news well, if anything they were more curious than shocked. I’ve also told an ex work colleague and close friend, he was surprised but is also very supportive. He has said he would like to met Stephanie some day! May 1st. Today I told my two brothers about Stephanie! and all went well and both have offered love and support. Also today my wife told her mum about Stephanie. I’m pleased to announce that All went very well . 27th May. Today I met up with my long term CDH friend Andrea who I have know since joining here 4 years ago. There were so many firsts achieved this weekend such as the first time I have met another CD’r as Stephanie, the first time I’ve been on an overnight stay as Stephanie, the first time I’ve sat in a bar and had drinks as Stephanie, the first time I’ve eaten in a restaurant as Stephanie, the first time I’ve had photos taken with another CD’r, the first time someone else has taken a photo of Stephanie. Thank you Andrea for a lovely weekend. I love all styles and fashions but the more feminine the better, my preference’s are dresses but I’m starting to love skirts as much and I love both midi or mini lengths. I’m told by some of my girlfriends here that I have a fabulous eye for fashion and style which is very flattering. I’m always happy to chat but prefer messages as I’m rubbish at the chat rooms due to my dyslexia lol. Please feel free to PM me a msg anytime. Love you All, take care and wishing you a very happy 2022 
Stephanie xx

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Marie Chandler
Trusted Member
2 years ago

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!

Marie Chandler
Trusted Member
2 years ago

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.

Sarah Kanter
Trusted Member
2 years ago

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!

Charlotte Walker
2 years ago

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.

Charlotte Walker
2 years ago

Your article was inspiration to me
Hugs Charlotte

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