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.

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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).

EnFemme Style

 

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…

EnFemme

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Juliette Parfois
Lady
Active Member
2 years ago

Well done Stephanie! A great story well told. It might have been low-risk but your adrenaline levels will have been in the red! Your story is full of encouragement for those of us still to take that large step out. Make use of the momentum you’ve got going. I look forward to hearing how your journey progresses, how much more risk you’ll build into Stephanie’s next outdoor adventure!

Alicen Thairms
Lady
Active Member
2 years ago

Congrats on your first trip out; wishing you many more enjoyable outings.

My first outing in the day was on a cold winters day five years ago, a twenty minute drive for a walk by the sea. Since then I’ve been out regularly, if I haven’t time to drive anywhere I go for a walk nearby. Going out has become the main part of my crossdressing sessions.

Emily
Lady
Active Member
2 years ago

Well done you! The first time is always the hardest. With experience comes confidence. The world now belongs to Stephanie! Have fun!

Angela Booth
Member
Trusted Member
2 years ago

And there you are! No one noticed the lady walking and driving her car. Well done to you and I hope the next one is as good.

Beth Green
Lady
Member
2 years ago

Wonderful! Stephanie is out in the big world! There is no stopping you now. Your experience will give you the tools to succeed on further adventures out and about. You go girl!
Beth

Brielle
Lady
Trusted Member
2 years ago

Hi Stephanie! I am so proud of you, GF! My first time out it was after midnight and I didn’t get out of my car while driving around the town I lived in. The most adventurous thing was driving up one exit on the freeway nearby and back.

You are a better woman than I (giggle!)

Raquel Smith
Member
Raquel Smith
2 years ago

Oh, the horrible scenarios we can imagine before that first outing. Yes, Murphy and his damned law, are always lurking around the corner, but it seems fate usually protects us from him and most crossdressers have a wonderful first time.

Great story, Stephanie. I look forward to hearing about your next walk, and your next, and then your trips to the store, and your visits to restaurants, etc.

I wish all the rest of you could experience it.

Much love,
Raquel

Cassie Jayson
Duchess
Trusted Member
2 years ago

Thanks for sharing your story Stephanie. The fear of going out and then the excitement when you actually do it is like nothing other. I know the first few time out for me was going to a nearby rest stop, getting out to read at a picnic table. I wanted to be seen, but only at a distance. Now a year and half latter I am going into the local mall and doing some shopping. I know some here prefer the self check outs, but I prefer a human cashier – a lot of technology I don’t like and don’t… Read more »

Rozalyne Richards' class='avatar avatar-64 photo' height='64' width='64' />
Member
Rozalyne Richards
2 years ago

Well done Stephanie, like you I’ve only been out on late night drive’s, no one can see you in the dark, about a couple of months ago though i managed to go for a walk around my housing estate in broad daylight, it was about 2-30 in the afternoon, I let Roz out of the closet and took her for a walk,
I was nervous all the way round and just kept looking round to see if anyone was looking at me, I’m not sure when I’ll be able to do it again,
Hugs Roz X

Michelle Last
Lady
Active Member
2 years ago

That’s wonderful. I know that was so exhilarating for you. The couple of times that I had stepped out on the front porch (after dark) fully dressed was an amazing feeling. I’m happy that you took the leap.

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