The Drive of your life

[Helen_Highwater]

So this is doing things back to front as it started with a post about what, once out and about, gave you the greatest confidence boost, it then being followed by this which asked about some of your early sorties out.

So now I’d like to talk about that which I suspect the vast majority of us have done in our earliest exploits, namely, the drive in the car while dressed.
My earliest forays (30’ish years ago) involved me going out the house in drab after dark, driving somewhere quiet, a country road layby, changing and then driving around for an hour or so. This then altered to finding somewhere to stop, again a quiet country lane, and getting out.

I can remember being so scared just walking around the car. Out, around the car, back in desperately trying to walk slowly and not like an Olympic road walker. I learned to listen out/watch for the distant headlights of any approaching cars, counting the seconds before they came into view. I then would walk away from the car, counting the time it took, stopping a second or two short of the time for any approaching car and then turn back. That morphed into walking away then just standing there, ears and eyes on full alert for that approaching vehicle. On more than one occasion the walk back turned into a decidedly unladylike sprint!

I found a layby that was a big loop way from the road. I’d park at the midpoint, walk along the layby onto the road, along the road to the other end of the layby and back to the car. Best I can describe it is like walking around a capital D. I guess the total distance was 150-200m. Seemed like miles at the time. Still, it’s was much further than I’d ever walked in heels constrained within the four walls of the house.

Next step was finding a post box and parking a distance away. Then I’d walk, trying to look as natural as I could to the box, either post a letter for real or, just pretend and then walk back. Putting drinks cans into supermarket recycling bins was another ploy. Again park a short distance away and walk to and from the bins. This last one was perhaps the very start of mixing with the muggles.

What I wore at that time were items “rescued” from the charity bags my SO would sort out from time to time. Not surprisingly they weren’t the best fit as while my SO is fairly tall there’s still that difference. Shoes were the hardest thing. My SO being several sizes smaller than me meant a lot of squeezing and discomfort. Looking back there must have been some real fashion disasters! This was pre internet and years before I bought my own clothes.

I guess these adventures were a measure of the need so many feel to get out and express ourselves more fully.

Things such as these were my early staple for getting out there and sustained me for some time and could have remained so. What changed was getting the opportunity to go away alone for 7 days and be free to dress. But that’s for a different story.

So here’s the question. Is this you? Do Helen’s earliest adventures chime with you? Were you someone for whom the drive dressed was your first tentative moments out the house and in the muggle world? If you’ve yet to go out that front door, is this something you see yourself doing, your first baby steps?

And just to round things off, I did have one big disaster. I used to use balloons filled with wallpaper paste as forms. Being a gel they behaved more like real tissue as opposed to just water. Anyway on one of the occasions I needed to sprint back to the car, everything was in motion and one of the forms burst! Trust me, trying to get wallpaper paste off you not to mention the dress and avoiding getting it all over the seats is no easy matter. No pain, no gain eh!

[Lana Mae]

I started with the car ride prior to owning a wig!
My transformation was next! Rented a basement apartment from the person doing my transformation! I was en femme for 24/4! I went to Asheville wig shopping but it was very rushed!
A mall run with a make over at MAC counter! First outing by myself! Realization that everyone is in their own world!
Out getting gas!
Grocery shopping and then grocery shopping and getting gas!
Of course, at the counselor!
Oh, so great...to church! Feels so good!
And the beat goes on...
Hugs Lana Mae

[Lisa Roberts]

I thought I was the only one who did this!!! The need to just “get out” was/is so strong sometimes. I love to drive EnFemme. Stopping to shop, get gas or potty break in places so far from home is very satisfying.
Lace and Smiles,
Lisa!

[sarah_hillcrest]

Yeah for me it was just last Fall, Drive to a nearby trail and get out for a walk.

[Sidney]

LOL, not out driving at first. Had a fear of accidently braking a law and getting stopped by the police. Or even worse an accident.

I've stated before with mustache no passing for me. Skinny jeans, bra small forms, kinfolk of nutral female t or blouse, sock less tennis shoes or wedges. Shorts a little above mid thigh.

We live in a very upscale apartment complex on the first floor. In the evenings I'd venture out with trash to dumpster about 400 feet from our unit. Would fetch mail at bos about 300 feet away. Terrified walking past other units and parking lot. Later when passing people just stereo saying high and got a high back and a lot of iles.

We live all the way at the back of the complex and our patio has about 100 feet of grass and then woods for miles, very private. A few people walk their dog early in the morning, late afternoon and evening. Remember one morning I fixed my coffee about mid morning and went and sat on our.patio to enjoy the quiet, folks at work and kids in school. LOL, I remember this like yesterday. We have a railing and flowers around the patio and no one could see me unless they were right up to the railing. I was wearing panties, big girl boobs and bra and a knee length semi sheer pink nightgown. Was relaxing when I hear someone say "high neighboor. Husband and wife from up stairs walking their dog. Too late they were right their staring down. They talked for 10 or so minutes. Wife started to come out saw neighbors and said I'll be out in a bit. Lord I didn't know what to do or say. When they left wife came out with a robe and I just chuckled and said that's kind of late. Have talked to them since in drab and there nice. The other wife is always smiling while we talk. Would have loved to have heard the conversation when they went back inside that first day. Like I said she is super friendle. Hummm, maybe he's wearing panties and nightgown now.

Glad I b don't care what people think anymore. I think there more than a few here that have figured me out now but no problem at all.

[kimdl93]

I always seem to be an outlier. Driving came after I've begun venturing out in my neighborhood for walks....but not long after. I believe my first drive 'en femme" took me to the mall near my home!

[chris80]

When travelling home from the Rotherham Beaumont weekend I would drive back dressed. Leaving the hotel at 4pm light, in November darkness the neighbours would be unaware as I arrived home. I used to do as every girl does and go for a final pee before getting into the car. I was exceeding glad on one occasion 4 years ago as the motorway came to a halt for an hour while some poor lady had been badly injured in a crash and I think she died on the way to hospital. As time passed many men in their cars ran across the carriageway to the edge of the road and disappeared down the bank to relieve themselves. The ladies in the cars would have had to cross their legs and smile for an hour. I was so glad not to have to dive across the road in my skirt. Moral-- en femme have a pee at every opportunity.

[JeanTG]

First time I drove dressed was to visit my therapist while dressed. I've been out dressed a couple of times (meaning not just driving, but shopping, walking about town). But dressing is on ice for now and is likely to be so for a while.

When I drove to the therapists, while I was on the freeway I had a panic moment when I saw a car coming up behind me that was identical to that of a friend of mine. Turned out to be someone else when he passed me. And now I'm "out" to that friend and almost all my significant friends so I don't have to worry.

[Cwest862]

I ventured out driving for the first time earlier this week. I had to run to the ATM to pay the workman the next day and didn't see any point in changing clothes. It was 9 or 10 p.m. but there was still a thrill to it.

[cdinmd206]

My first time was at Halloween when I dressed in a maids outfit complete with stockings and garters that were quite evident under the short maids outfit. I had forgot to fill the car up with qas and wife said we will just stop along the way and get gas. We pulled into the stop and go and I thought the wife as going to get out and pump the gas and use a credit card. She looked at me and said this was your idea so get your panty covered ass out and take care of filling the car with gas. Besides the maid outfit I was wearing a very long blond wig that just said "Hey look at me".
I got out and while filling the car another car pulled up on other side of island and 3 teenage girls got out. They looked over, laughed and said nice Halloween outfit. Straight faced I said no this is what I always wear. They asked if I was serious. I could not resist it and said yes, again with straight face. Things sort of deteriorated after that.

[DIANEF]

First time I left my house and was in public view was when I needed something I'd left in my car. I'd parked on the road which is about 6 meters from my front door, ( my son's car was on the driveway), it was dusk and I thought, s.d it, I'm going for it, and I did. I live in a cul-de-sac and could hear people passing the entrance to it, and to my surprise it didn't bother me at all. Then I did the night time drive thing a few times, then daylight, then increasingly long walks away from the car. I've gone from a few tentative steps to spending an hour in the city center, but I still have a lot more to do.
Love the story about the wallpaper paste boobs Helen!

[Millisense]

Helen your posts are so evocative and well-written, you bring back so many memories that not just chime but ring out!

My first outsides were walking late at night in my neighborhood from about age 13 in full dresses or sometimes in lingerie, also learning to listen for cars like you (thanks for the reminder of that!), scout out hiding places in case one came. (no streetlights where I grew up, so little worries neighbors seeing me)

My first drive out was aged 17 in summer 1978 in a black skirt, black lacy full-slip and matching bra. I wore heels as well -- you reminded me of the "squeezing" into them, lol, I had totally forgotten that! I wore a regular t-shirt as it was daytime and wanted to look normal from chest up. I brought jeans as well that I had worn out of the house, but I slipped them off and put the skirt on at a stop sign, not leaving the driver's seat to do so.
After a while driving around town on a crowded shopping street, at a stoplight, I put the car in neutral and slipped the skirt off, just to be naughty, I was going to put the jeans on later. But when putting the car back in gear, I got confused with the heels on and hit the gas instead of the brake, and rear-ended a little yellow MGB in front of me, causing a fair amount of damage. The woman driving the MGB got out and was obviously angry, but when she got to my window and saw me fumbling in the lacy slip trying desperately to get my jeans on, it visibly shocked her, and it helped diffuse the situation I believe. The police came, etc. but I was back in guy mode by then. At least no wallpaper paste was involved

I didn't drive dressed again until last month.

[Charlotte7]

Hello Helen, yes, this was me, back then, I had to get out of the house, I had to be out there, as me, showing to the world, but on my terms. I didn't wear make-up and so it was something for the winter months, when darkness was my friend. I started with driving around but, like you too, I had to get out of the car, to walk about, although in my case I quickly evolved from hanging around outside the car to walking considerable distances, so that sometimes I would be a mile or so away from the car. It was so exciting at the time and I loved it.

It was also, as for you, a long time ago, in my case about 30 years, and back then, public cross dressing wasn't really thought about by the public at large. I felt that I could hide not only cloaked in darkness, and sunk deeply into the hood of my coat, but also by doing something largely unexpected. I wouldn't have passed close inspection, of course I wouldn't but that didn't matter, what mattered was being outside. So, I wore a jacket rather than a longer coat. My thinking here was that when people saw me, and of course people would see me, they would see a person in a skirt, a person in tights, a person making, what I like to call, ladies' shoe noise, and they would think, female, because they had no reason not to. I picked where I went carefully, 20 miles and more away from home, in a different town, mostly in wide suburban streets, with pavements and streetlights, and large front gardens, with hedges and shrubs to shield the owners from prying eyes from the street, but in my case doing the same but in reverse. Sometimes I would venture out from the side roads and walk on the slightly more busy roads with a few more people around and certainly more cars. In these cases I always made sure that I had my back to the approaching traffic, so the first thing the drivers would see would be female, with nothing to contradict that first impression. Then, it was a real thrill and I loved it.

But it was only a phase that lasted a few years and I stopped. There wasn't any particular reason why I stopped, but I did. I wasn't something that I thought about it just happened and after a while it occurred to me that I hadn't been out dressed for a long time and I didn't feel the need to do it again. And I'm happy now to have it in my past, something to have done and to have enjoyed, but there now where it is, in the past.

To answer your question though, 'The Drive of my Life' I suppose the answer for this is the time I went and had a look at the Blackpool illuminations. This was memorable for two reasons, firstly the length of time that it took, to get there and back took a couple of hours and more (each way) and secondly, it took hours to drive along the promenade, and there were so many people around, probably thousands over the whole course of it. It was great fun, and a not to be forgotten day.

And I suppose that we also have to remember that this was before the age of mobile phones, certainly phones with cameras on them, and before the internet with its social media and YouTube and the like. Times were quieter then, more innocent, more private.

[alwayshave]

My first time out was to a local CD friendly bar, via cab, which was an issue in its self. At that time, living in the city I did not own a car. Since then, owning a car, I have never driven dressed, I always thought it was the most likely time for being confronted by law enforcement.

[Teresa]

Helen,
My first steps when driving were to stash a skirt and heels in the glove box of my carfor the journey to take the kids to school which was about 10 miles. I'd park up and slip into the skirt and heels to drive home . I still remember that first sight of a skirt hem across the knees and watching my feet work the pedals in heels . I still feel there is something very sexy about seeing knees in stockings with a hem line just above when driving , I loved watching my wife's legs when she drove . I progressed to fully dressing to take a drive , I had kittens the first time when I had to stop at a pedestrian crossing and people passed within feet from my bonnet looking at me waving in thanks for stopping . I also realised not to be so sharp with driving skills , I had to do a quick U turn near a fire station , some of the crews were out front and they looked in amazememt to see the quick about turn ( sorry ladies but guys do usually do it quicker and slicker !).

Even now it's become an almost every day thing I still love driving dressed , I still have to take care with getting in and out elegantly , my daughter has always pushed her seat fully back to get in and out the car I've realised why now it does make things much easier .

[GretchenM]

My first time out was on a winter night. It was about 15 to 20 degrees F, so I bundled up. Wore clip on earrings in addition to wig, makeup, etc. Walked about a mile to a restaurant area within a residential area and then along a main boulevard (Broadway) and back home. I saw about 3 people that were out walking and didn't pass anyone directly. It felt good, except for one thing. Never wear clip on earrings when it is cold, even with a warm knit hat. Those things are heat magnets and suck all of it out of your earlobes. It took a half hour before I regained feeling in my ear lobes. I have not tried a repeat performance. On cold nights I stay in.

[Stephanie47]

My initial adventures outside the house were taking drives at night. Thinking back to those early days (1980's) I must have been crazy. My wife has never been accepting of my desire to wear women's clothing. I can only assume my absence was noted but she just played dead when I was absent from the bedroom. I got dressed in the bathroom on the other side of the house, which was between the kids' bedrooms. Yep, bra, panty, slip, hosiery, dress, wig, and, facial makeup. I slipped out of the house. Got into the car and let it roll down the inclined driveway before starting the motor. I drove through our end of town and avoided the main drags. After a few adventures I started parking and walking through residential neighborhoods. The farthest I drove was about ten miles away. The most apprehensive adventure was having a police car roll up alongside me at a red light and give me a once over. I think back and wonder if my wife ever noticed my absence. I'm sure she did but just did the ostrich thing and stuck her head in the ground and ignored my escapades.

I also created and have mentioned here before reasons to get out of the car; the mail the letter, get a soda/pop from a machine, get a free newspaper, return library books. I no longer "sneak" out of the house. When my wife takes an overnight trip I still will go for a drive, but, the uncontrollable desire is no longer there. I'm content to be June Cleaver.

[Alice B]

My first real drive was from San Diego to Las Vegas for DLV. Left fully dressed. make up wig and all at about 6 AM. Stopped for gas and coffee at Barstow, which was full of military personnel going to work. Had no problems. Next stop at Baker for something cool to drink ans final stop for gas just oitside of Vegas. Pulled into valet parking at Paris and bell woman came up to take my bags and gave me a great compliment on my looks.

Drove all around Vegas for the next week dressed and then drove home at the end, starting at 10AM. Never had a problem. It was a great experience and a major confidence booster. Taught me that the ony thing to fear is yourself. NO one else cares

[Yukihime]

Rather than the "Drive of my Life", it'll be more accurate to call it the "Walk of my Life" 😉

My first walk was actually a two parter and took place during a trip, first to a city in East Malaysia, and the second in Peninsula Malaysia.

In East Malaysia, I miscalculated and accidentally booked my hotel across the road from the adjacent mall, and had to power walk across an overhead bridge and past an open air carpark to reach the mall. And once I was inside, my courage only lasted long enough to reach the department store and buy some panties, a slip and robe from the lingerie section, before rushing back to my room to recover. 😅 I discovered when I got back that my wig had tangled up with one of my earrings and had to be trimmed slightly.

In Peninsula Malaysia, already bolstered by my first run, I took slightly less time to get dressed and had a much more leisurely walk around the mall (which was actually adjacent this time!) and walked up to the end of the mall, bought some items from a La Senza and a supermarket, before my feet started complaining about my heels.

In both cases, I spent my time in the hotel room all dressed up, and both definitely gave me the courage to forge ahead further and start dressing in my own country, not just when overseas.

[t-girlxsophie]

I'm not a driver,I'm the one getting chauffeured about

Way back when starting out I made friends with a girl at local support group,we used to change in her car,and make the all too short journey to the meeting place

The first time travelling a long journey dressed was in the mid 2000s to Manchester,there was 5 of us in the car,mix of Cd and TS ladies and It felt amazing to be so far from home all dressed,even stopping off at service station (stayed in the car)

Of course now I'm so used to it,but it kinda has went full circle,recently as documented here,I travelled back from Manchester dressed and going into the very same services,which went without incident but felt incredible

Sophie

[Beverley Sims]

A bit of the same until I met the four girls who rented the house with me, they MADE me come out and join them, on Saturay night jaunts and also as a body guard to protect them. Then it was back to the car and a suitcase for a while till I got married.

[lingerieLiz]

I loved driving back in the late 50s and 60s. It was illegal for a guy to dress as a woman. Grew up with 2 sisters who loved to teach me how to be a girl. My mother would be hot and cold about it. It was fun to drive and see your nylon covered legs shining with the lace from your slip showing a few inches below the hem of your dress. I did learn that cancans didn't do well with steering wheels. They worked better if you were the date. I've driven cross country several times in fem.

[Sallee]

First outing I think was a 60 mile drive to a drag show in a Boston gay bar. I had to get gas on the way back WOW was that hard and exciting. The attendant pumped for you then and he had to tell me to turn the car off. I was so nervous but what a rush.
Needless to say things have progressed since then.