What problems did you experience when you first dressed?

I am a Halloween dresser when i first dressed as an adult for work (we was encouraged to dress up).I walked to the car and realized I have no pockets where is my wallet going to go or my car keys when I get out?I decided to lock them in the office no biggie when i got to work another problem hit me.What am I going to do with the store keys I usually put them in my pockets or strap them on my belt but no pockets or belt.Couple years later I dressed again for work and was wearing thigh high boots.I thought no problem carring my wallet and fone I will stick them down in my boots like I have seen in movies.After a few steps my fone slid on down my boot and my wallet fell out so I being a super genius that I am. I took my money and card out of my wallet and put them inside my boot and left the wallet in the car.My money and card slid all way down to my foot and my fone was stuck in the other boot.Next time I dressed I bought a purse.

It's not limited to when first dressing. When I go for a drive, anytime, I always carry a single key which opens the car doors, trunk and the ignition. I also carry a second set along with keys to the house and mailbox. As a dad I had to bail my daughter out too many times with key locked in the car.....no keyless entry way back. When I go out for a drive and stroll en femme with nowhere to carry the set of keys I carry them around my neck on a chain which hangs down into my dress. I carry my skinny wallet in my bra.

Brandie,
Very simple solution but yourself a handbag/purse . For any girl out and about it's a MUST HAVE !

On the odd occasions I go out in drab I really miss mine .

As for problems when I first dressed , I have to think back 60 years !!

It is always critical to make sure you have certain items like ID , keys, cell phone, money, etc before leaving home. I do not carry anything unnecessary so that caused me to goof up. I parked in a lot that only accepted credit card payment to exit and I only brought cash. I left my ATM and credit cards at home. I was going to have to use Uber to go 20 min home and back again just to get a credit card and that was late at night. Fortunately the Uber driver let my pay her cash and used her card to get me out so I gave her a big tip. Gotta think of everything for sure before you head out.

Sandi

When I first dressed, I wasn't very good at it. Lousy wig, lousy hip padding, lousy makeup, etc. I imagine that would be true of all crossdressers. I've spent a lot of money, but I've got the right stuff now and look much better.

I always carry a handbag because it makes getting "the walk" easier. I don't often see women in the street wearing clothes without pockets and no handbag - it looks odd. One of my earliest times out dressed was staying in a hotel as Susan. I had booked as Susan and changed in a B&B the night before. As I had only been out a couple of times this was very scary. I actually tried to convince the hotel I was a woman and by the end of my four-night stay it was clear I had failed in this but they were too polite to say anything. When I came clean, they said I had been so shy I had not been making eye contact and they found this quite difficult to deal with - the crossdressing was fine. I went back to that hotel (which is now closed) many times and got to know the staff. So my big mistake was trying to pass. Once you realise you don't you have much more fun. The staff gave me lots of compliments about my outfits and one of them said "You have better legs than me, you bitch" then she apologised for talking to a customer like that - I just thought it was funny.

Buying unflattering dresses. Yeah, try everything on before you buy, but I was too shy back then. I ended up with a lot of gunny sacks and dresses that hung open at the top to show my bra. Live and learn.

When I would first go out I would always carry a change of drab clothes in case something happened to the car.
One time I was going away for the weekend and wouldn't you know it, the car broke down and had to be towed. Here I was on the Interstate with no where to change. It seemed everyone wanted to help this damsel in distress. First a passerby stops, then the State Trooper. Having survived those interactions I just said WTF and waited for the tow. A young man came, was so polite and respectful, talked all the way to my house and never once said anything about my attire. Dropped the car in the driveway and I gave him a nice tip for his courtesy.
I no longer carry that change of clothes.

Mostly getting the sizes right. I never try things on in store, so I did get it wrong a few times. Nowadays, I can eyeball fem clothing as well as male.

Combining pieces into outfits was another one, but that kind of problem eliminates itself for the most part once one gets a decent wardrobe.

I was upset that my Mom’s things were a little big on me.

A couple travel related incidents come to mind. I?ve made several crosscountry trips up the I 35 corridor en femme. Once, just north of Muskogee, the distributor cap cracked on my vehicle. It managed to limp its way into a GM dealership I spotted just a few hundred yards up the road. The staff there were totally courteous and helpful.

A second incident occurred while I was pulling a U Haul trailer through Wichita KS. A tire on the trailer blew out. Again, I was en femme. I called the company and they arranged for someone to replace the flat and I was on my way. Again, total courtesy and helpfulness.

Had a couple of car related issues myself back in the early days but the worst happened around 1987. My mum, dad and I were staying at a hotel just outside London. I had a room to myself for the first time and had taken with me my stash of female clothes (mostly borrowed from my older sister). I really wanted to venture outside the hotel but didn't want to pass through the hotel reception so I concocted a plan that involved changing in our car which was parked out the front of the hotel and then going for a walk up the street and back. To get the car unlocked I'd asked my dad for the keys earlier in the evening and said I'd left a magazine in the back seat. Later that night I sneaked out to now unlocked car with my supply of female clothes, changed and put on my make up. When the coast was clear I got out the car and shut the door only then realizing I'd locked it. My drab clothes were in the car along with my hotel room key and I couldn't get to them! In a state of panic I walked up the road en femme, desperately trying to figure out what to do. For about an hour I hid behind some bushes next to the hotel and then climbed over the perimeter fence to see if there was an unlocked back entrance. There wasn't. At one point I was contemplating breaking the car window but realized I had no choice but to head back into the hotel, dressed as I was and ask the night manager for a spare key to get into my room. Thankfully he was an older guy. God knows what he must've thought when he saw me walk in. Putting on my best female voice I explained that I'd left my key in my room. Unfortunately he had no spare key to give me so I had to follow him up the stairs to my room where I was let in. I didn't get any sleep that night. We were checking out of the hotel the next morning and I had to get to the car ahead of my dad and retrieve all my clothing. Quick thinking kicked in - I headed along to my folks room as early as possible and asked my dad for the keys once again, using the same excuse that I'd left something in the car that I needed to pack. I raced down to the car, grabbed my stuff from the previous night and returned to my room. The night manager was still at the front desk as the day time staff were showing up. I'm not sure if he recognized me. I always wondered if they had CCTV footage of my grand entrance. Since then I've ALWAYS been careful about locking the car when I'm out and making sure I have a supply of drab clothing in the back just in case disaster strikes.

Patience got it ...
Sizing is the worst, still is to an extent.
Takes time to find what really fits. There is NO standard in clothing, men's or women's. everyone uses their own reference and shoes are the worst. Each brand has their own "lasts" which are the forms to which they make their shoes and they are all different. Some run narrow (Steve Madden), some true (Clarks), some run wide. I found that it much easier to find a brand of clothing or shoes that you like, find your size and stay with that brand, then you can just buy off the rack and be fairly certain it will fit as you like it to.
Sometimes brands will even change as my wife saw. One brand used to be 14-16 and 18-20 then suddenly they are marked 12-14 and 16-18 and they don't fit the same.
This to me is the most frustrating thing to go through when you begin and just want an outfit or two and don't want to break the bank. All that buy, try, return is horrible till you find your sizes.

My mum finding out. I loved to try on her nightdress when I was five years old for reasons I never understood at the time.

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Originally Posted by Teresa

Brandie,
Very simple solution but yourself a handbag/purse . For any girl out and about it's a MUST HAVE !

On the odd occasions I go out in drab I really miss mine .

As for problems when I first dressed , I have to think back 60 years !!

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Simple solution for you Teresa just carry your purse with you on that odd occasion. I bring mine all the time. Funny to was when I was asked to leave it at the front of the store. That was partly because I have a mini backpack style bag.

My wife pointed out that I wore dresses that were way too old for me.

I first started dressing in middle school so my main anxiety was about my parents finding out. I know I never replaced my mom?s unmentionables in the same place as she had them but she never said anything and still hasn?t to this day. She had to notice that after I moved out everything stayed in the same place in her drawers but nothing was ever said.

First full day out in public? Wore a way too short sexy dress, and wig was also too small. Was shouted about, watched, was asked by a man with children to give them a car battery jump start, because i was parked next to them. He told his kids not to look. I was the only possibilty to jump start him, and i said sure, and got his car started, but it was stressful for him, and his family. I was truly dressed as a hooker though. Too much pink fog.

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Rachel Wcat, Wow, what a lot of drama there!! I can see why you had no sleep after that, and then having to do more adjusting in the morning! That reminds me of when i locked myself out of a motel room, in 2010, all dolled up on the third floor in a short tight dress. I sighed for a minute, then realized i had to go down three floors to the busy front desk, and ask for another key. I took off my high heels, decided i could walk much faster in hosed feet, took the elevator down, and in front of many children and parents went and told the desk people what happened. They gave a key, and i went to the elevator again, went up to the third floor, got off, was looked at at by a few men, walked fast to my door, grabbed my heels and dodged into my room. Good thing i had a wig on, but i know i was outed.

Fastening the back clasp on garter belts haunts me to this day...and there has been many days. My body will NOT twist that far!

There is a huge difference between finding clothing that is my size and finding clothing that fits my size. Luckily, I saved a lot of money by learning this lesson through thrift store purchases.

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Originally Posted by lingerieLiz

My wife pointed out that I wore dresses that were way too old for me.

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Were the clothes old or just old fashioned? How did you go about changing?

Thank you, Cheryl, btw.

The main problem I had when I started dressing was making sure I put everything back the way my mother left it so she wouldn't know I was wearing her things again...

OMG! Like I have no place for my wallet and keys now. I guess I will have to get a purse.

Shoes.... need I say more.

Figuring out sizes.

Puttning my mothers clothes back in her closet without ger noticing it... Long time ago.

Also later on buying clothes and shoes. I was very shy as a kid. I remember one time I was shopping for a pair of high heels in my teen years. Traveled to The other end of my town. Got into the mall looking for stores.
Got into a shoestore quickly scanning for the most feminin shoes. Found them. Then got in line at the cashiers, heart pounding, money in my hand.
The cashiers, a girl maybe around 20 years old grabbed my shoes and said "well honey thoose are very high heels can you manage them?"
I just mumbled something and handed over the cash. Got the merch and hurried out... How could she know was in my head, my head was spinning. Lucky me there was nobody I knew lurking around. And I did manage thoose high heels.

Everytime buying female stuff got me high. It was scary but so exciting. Like a rollercoster. Sometimes dissapointment getting home and nothing fit.
I have bought tons of clothes not fitting. Still happens but nowdays I'll send it back.

I was not so advanced that makeup was my a-game but later on internet and Youtube fixed that.