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I had the house all to myself, decided to apply make up, still learning. Put on a skirt and a tank top sweater, all borrowed from my SO. I had bought a pair of 3” heels and a wig, to that point I had never even walk out to the front porch, too scared, as it got dark knowing nobody was coming home, I made a brave decision to go out, managed some courage, opened the garage door from the house, looked out to make sure my neighbors were not somewhere in their kitchen looking over to my driveway, ran as fast i could to my car and drove off. I went to a semi empty parking lot, a combination of offices and a few restaurants, decided to take a walk out in front of a dental office, as I was walking under the lights, I saw my reflection on the window, OMG what a feeling! Wondering if anyone else has had this experience. I still get excited but not like that anymore, I just enjoy being a lady.
I had to get my boat from the marina which was a 5 mile drive away. I was already wearing panties and a bra so I slipped into some jeans and a tee, freshened my lipstick and drove to the marina, got the boat trailer, went to the dock and loaded the boat. Just as I was securing the boat to the trailer a truck and trailer pulled in to unload. I finished my task, smiled at the driver and left. Exhilarating!
My first "real outing" was a long time ago now in the early 1980s.when I was early 20s I was lucky enough to have enough privacy to often spend a day or so 100% femme , I was pretty good with the make up and hair , my look ranged from trendy 80s girl to a little more mature.
One thing that always bugged me was the fact that circumstances prevented me shaving my legs. Id picked up some gorgeous sheer nude stockings a few days prior and as ever been saddened by the mess of hair that was visible. That morning I just thought what the hell , went in the bath and shaved .
I prepared myself and loved the leg look . Sufficiently emboldened hair , make up done and a suitable business winter outfit and outer coat ( courtesy of my mothers work wardrobe ) off I went for a walk around the park .
I was buzzing . That wasn't my first time out , I'd gone out dressed in my teens (I can tell the story if anyone is interested ) but it was my first time as a visible presentable woman.
My first time out was a long time ago. The feelings range from exhilaration to deep fear of being clocked or accosted. The fear was not enough to stop me and I continued to do it. My confidence grew over the years to the point where now it is becoming more my norm and I am out multiple days per week doing my everyday things.
It wasn’t my first time out but my best time is when I finally went got out during the day. So many times it was at night. I always felt like I was hiding myself, which was true. I had a weekend to myself and a different car that know one would recognize. It was a beautiful warm day. I spent a lot of time on my makeup. I wore a dress and low heels. It was something that didn’t make me stand out but made me feel feminine. I wore sunglasses and always felt very passable with those on. I just felt so confident that day. I drove around the country side for a while. Then drove to the nearest bigger town where know one would know me. Walked around in the shopping district. I was just the most relaxing wonderful day. Just wish I could have more of them.
My first outing was unusual. I was just starting a trip which included a flight to visit friends down south who know and support my CDing. Best ticket prices were available by flying out from a nearby city, and the evening before my flight was contemporaneous with a gathering of a CD support group in that city. So I made a reservation at a nearby hotel, packed up drab me and Charlotte's things, and set out.
As soon as I got to the hotel, I showered, shaved, and primped. I did an OK job with my makeup. I have no memory of how I dressed, other than wearing 2 1/2 heels. (It wasn't the best idea to drive for the first time in heels in an unfamiliar city.) After some trepidation I stepped out of my hotel room and into the hallway. It was empty. I rushed to the elevator. Also empty. When the elevator door opened to the lobby, I surprised myself by emerging without further hesitation. I walk across the lobby, noticed by the young lady who checked drab me in, and a well-dress gentleman who looked at me with mild curiosity. The parking structure was a very short walk from the hotel entrance. There were a few small groups of people chatting amongst themselves, starting their Friday evenings just as I was. I got in my car and drove to the gathering.
Once I arrived at the restaurant, I had a sudden pang of nervousness. This wasn't the first rodeo for hostess of the gathering. though. She foresaw I might have trouble getting out of my car, and gave me her phone number so that I might ask her to escort me. I did and she did. She deftly put me at ease.
Dinner was very nice. I had several enjoyable conversations with the folks there, including the very loquacious and charming wife of the organizer. After dinner, the hostess invited me to join her at a bar near my hotel, and we sat and talked for hours. I received a complement on my appearance from some passing young ladies while there.
All of Charlotte's things were in checked baggage for the flight. I assumed my breast forms would arouse immediate suspicion under X-ray and just resigned myself that my things would be sorted through by security. I was surprised to find I was rather ambivalent about the prospect.
I'm sorry to say that when I arrived at my friends' home, I didn't have the nerve to get dressed as Charlotte. No one pressured me during the visit, but upon my return home, they both asked me why I chose to not present as a woman. I told them I was worried it would be a burden to our friendship. I was quickly put in my place as being foolish, and they requested a visit with Charlotte on my next visit.
I'm happy to report that on a subsequent visit, I was Charlotte for a time and they were very pleased to meet her. I received very encouraging feedback on this second visit, including fashion advice and complements on my lipstick game. Sigh.
In my 20s was the first time I went out anywhere. Late, late at night, under cover of darkness, during the midnight time period. A walk around the area, and if there was a car approaching, I would turn my back and walk the other way so if they saw me, it would be my back. These were crude days for me in how I was presenting myself so I never dared go out in daylight or any waking hours. That eventually came however calculated that was over the years. And I used COVID to my advantage as the first daytime trip — keeping distance from people.
The time I consider "first time" was not until 2022. I was on a cross country road trip, and out in California. "Now or never" I thought as I left San Francisco for Monterey. My intent was I would dress and makeup in hotel, pack up and check out as a woman. On arrival in Monterery I would find the proverbial "shady spot" clean off makeup as best as I could, change clothes, before checkign into the hotel there.
I ended up arriving in Monterey and just drove to the hotel. I thought... "what are you doing..." but something propelled and compelled me forward. It was like this had to happen. I got out of the car, went to the front desk, and gave my information for my reserved room. The woman behind the desk did not blink. She was as perfectly kind as any other stop I had on my trip. She even went out of her way, and gave me an upgraded room, and was nothing short of lovely. I was blown away.
I felt like for the next days in Monterey I was "locked in." i couldn't change back. I spent those next 2 full days in and out of restaurants, downtown and driving the 17 mile drop in and out of the car to see sights as a woman. Interacting with some people to. It was amazing.
At one point as I was driving down towards San Simeon, I got out to see another gorgeous overlook and no one happened to be there. The road was even quiet. I just blurted out "this is what my life was always supposed to be. I am and should be a woman." It was amazing.
A few more times along the way I presented as a woman out in public and it was nothing short of amazing and made me feel complete as a person. It changed me significantly for the better.
I was in grade 5, so that would have made me 11 years old. I was home from school for some reason and my mother was a teacher and at work. I had already tried on some of her clothes and lipstick - I know now that she knew I was into her stuff - but her shoes were all staring at me. I wondered...and stepped into a pair of her flats, they fit me perfectly! Hmm, My hair was already fairly long, a Beatle Cut, and I was a bit young to worry about boobs. I always had a baby face, didn't shave yet and puberty was still down the road. So I slipped on one of her skirts and a sweater, stepped into the black flats, and went outside. As I recall, it was a mix of excitement along with taking a deep breath, and smiling about finally being able to present myself as the girl I always felt I was.
There many, very many more, occasions where I went out dressed as the woman I knew I was!
Hugs girls,
Ms. Lauren M
My first time out of the house was about 10 years ago for a walk one evening. As I walked up the road I felt a strange release of inner tension and strong feeling of freedom...
The very first time out of the house I had to be in 7th or 8th grade. I had on my sisters knee length denim dress and black tights. I managed to squeeze into a pair of her flats. I went out in the backyard. No one saw me as far as I know.
The next time I was outside was 2003 for Halloween. My wife thought it would be a good idea for me to go out dressed. She had a friend come over and do my makeup. I wore a black stretchy dress with silver sparkles, black tights, thigh high boots with a mabey 2 inch heel and a bra and panty set from Victoria Secret that was my wifes. The set didn't fit her but she said it was meant for a special occasion and my outing was special enough. I remember the bra was a bit too small for me and was uncomfortable but the wife said something along the lines of "now you know what us women go through".
I slept in my makeup and I was up the next morning super early doing a paper route. I wasn't dressed as Missy but I knew the chances of someone seeing me was almost 0. Well, theres a reason I dont play the lottery very much because I delivered several papers to an old folks home, and the night desk guy was there. Normally hes never there when I come by. He looked at me and I knew by his grin he noticed the makeup. Whatever I thought.
Other than a few other times dressing while doing the paper route thats about it for any outside Missy adventures. I'm mostly wearing lingerie or tights/pantyhose under my regular clothes.
Over 40 years ago now. Lovely underwear with slightly padded bra with socks. Chords, cream colour, with block boots. Blouse covered with a denim jacket. Light pink lippy and I had long hair then. Its dark but I went for a stroll. Not sure I was so brave as in the New Romantic era in the UK it was a common sight. Liberating though.
Congrats for having the courage to do it as many of us are not that brave.
you are a good example to follow. 😘
My very first time outdoors and fully dressed was one winters evening when I was 16 so around 1979 I didn't have many items of my own but at that age but I was an identical size to my mum . She was a stylish lady with great taste . A lot of her wardrobe was from a place English girls will possibly recall, Country Casuals , Barbour and M&S filling in. I think if anything accelerated my dressing it was what I got up to around this time.
My sister played in an orchestra and one evening my parents , leaving moaning me behind , went to watch her play. That gave me approx 4 hours to indulge. As soon as they left the house I was straight upstairs to have a look through my mums stuff . I very quickly got "my" underwear on and can remember as if it was yesterday . a pair of my panties with a pad very wisely as it turned out , in case of leaks . A pair of nude pantyhose from my collection then one of her Playtex cross your heart bras and a panty girdle below . I felt wonderful . I can recall sitting there thinking what now .
One job I had been left to do was walk the dog so I think you may guess where this is going . I selected a full length slip , a houndstooh knee length skirt and a nice light pink silk blouse .perfect outfit for dog walking lol. I got downstairs wondering what the hell I could wear on my feet and I spotted a pair of her brown leather knee high boots . Size 7 , my size and a decent block type 2” heel . Id practised in heels by this point, but these were perfect for my planned excursion. It was then I bottled it . What on earth was I doing !!!!.
I just sat on the couch for ages my mind spinning lol then something clicked ......let's do this.
It was a cold dark evening so I grabbed one of her hooded coats and put it on leashed the dog , who wasn't at all phased by my appearance and off we went . I kept the hood up but there again so did most people out that evening and the gloves I found in the pockets were lovely .
I walked around the streets that night for about 1 1/2 hrs . The dog couldn't believe his luck and I felt so turned on and enlightened it was fantastic . For the first time I felt the winter draught around my nyloned legs. I felt the swish of the skirt in the fresh air. I felt the boots encasing my legs.. I had a vague smell of perfume from the coat . The feel of the bra and girdle.
All in all probably the most memorable and exciting venture out I have ever had . I knew who and what I was and still am and what I wanted to do about it . It was a real defining evening .
Once I got home having had absolutely no trouble and feeling high but tired I started changing back and tidying up. You know the score , searching the house , checking everything is away where it should be at least three times and more.
By the time everyone got home I was quite sad . The euphoria had passed and I wanted more but knew how difficult it would be . My parents actually commented that I looked a bit down , it was was written off as tiredness .
Needless to say I didn't sleep well that night and my dreams were , well interesting 🤔 watching.my female friends at school the next day felt so different . I knew what they were physically feeling or so I thought .
I stayed in the closet for far too many years and I often wondered if my late mother realised I had been borrowing her stuff . With hindsight I'm sure that answer is yes but I'll never know.
Sorry if it's not the salacious tale anyone expected but it is 100% true and I'm sure there's a few can relate xx
Please tell x
I had manyore outings too but none were more significant than that one . Another important one was when I was in the forces and we had a fancy dress night 😈
My first trip outside in any femme clothing was a walk in a dress around the shortest block locally, late at night last summer, to see if I could manage the heels I'd bought.
My first trip outside by daylight was a drive out, also last summer. I still had the beard then but I had a dress and jewellery on, but no wig. I stopped on a country back-road and put the roof down (always the plan, hence no wig 🙂 ) and then meandered around the empty lanes just enjoying it.
Than as I turned into one road, a van caught me up, I was sure the driver could see my bracelet and earrings, and probably realised I was in a dress with midi sleeves, I was just hoping he couldn't see the bald spot or the hair on my arms to identify me as male! The road led into a village, which turned out to have some roadworks going on, and the traffic light had just gone red 🙄 I had to just sit there what felt like forever, trying not to look at the van driver in the mirror, until it went green again. Then following slowly round the sharp bend I discovered why it had taken so long. The road crew must have been moving the cones and machinery etc. to start work on the other side of the road. But they hadn't yet laid any ramp on the side that was now open, across the trench they'd dug. So I had to sit and wait again, in full view of them all while they got to it! 😳 When I was finally able to progress, I just smiled and waved my thanks, but I'm sure I got some funny looks ... not undeserved given what I must have looked like 🙂
Eventually I found somewhere quiet to stop in a gateway that wasn't overlooked. I got out of the car and felt the breeze round my legs and the freedom of being out (at least partially) en femme, but I was still a little unsettled from the roadworks and the sun had gone in, so I didn't stay out long. Then when I got back home, I discovered my neighbour had unexpectedly come home, so I had to park the other way round in order to sneak out of the car without being in full view of their living room window. Overall, not really the experience I'd hoped for 🙁
A few weeks later when the neighbours were definitely away on a cruise, I did another drive out, and this time I went to a more remote location I'd researched, where even the only overlooking footpath went from nowhere to nowhere. So although it was right out in the open, it was about as private as it could be. Now that was the real McCoy, it was 30 degrees C with a gentle breeze and I was in a light blue floral sleeveless floaty dress. It was just complete bliss to be out in the field amid the beautiful scenery with the sun on my bare legs. If I go there again I'll take a picnic blanket with me to lie down and catch some rays 😎