My name is Ruby and I have been crossdressing since a few years but only inside the house. I always fantasized about going out in public as a woman but I was just too scared. I just love watching videos of crossdressers in public and I always wondered how wonderful it must feel to be outside and the thrill of being seen by other people.
Finally I decided it was time for me to step outside because the urge was just getting bigger and bigger. I planned to go on a short drive and get some takeaway food. So, one evening I got myself ready nicely, put on my favorite striped maxi dress, a blonde hair wig, heels, white ear-rings and light makeup. I had dressed so many times before but I could feel a lot more excitement while dressing up this time. I thought I looked good enough to blend in but I was still very nervous.
I lived in a quiet neighborhood and the roads aren’t that busy. But I was still scared if any of the neighbors would recognize me. So, I knew I had to make it a quick leave from the house. I took the keys of my car and again checked myself in the mirror to see if I looked fine. I was nervous to my core and I wasn’t sure how I was going to react if someone saw me.
I took a handbag with me and then opened the door. I must admit, I had never been so nervous my whole life. I stepped outside and I could feel my legs shaking. I locked the house door, put the keys in my handbag and start walking towards the car. I had a quick look around and I saw a couple walking towards my direction. I panicked and I went back into my apartment and I was shaking like a leaf. It was a close encounter and the sheer thrill of it gave me a huge high.
For few minutes, I tried to calm down and give it a second try. I peeked through the window to see if the streets were clear this time. I didn’t see anyone around so I hurried to get out again. I locked the door and went straight towards my car & got inside. As I was inside the car, I felt a little sense of comfort but I was still pretty nervous. I started the car and drove off the block.
As I was driving, I could feel such a rush going through my body, it was remarkable. I felt like each of my senses were heightened and everything was so vivid. The feel of the dress on my body, the smell of makeup & perfume I had on, my hair blowing slightly by the wind and the feel of heels on my feet. It was just amazing. I didn’t want the moment to end.
I reached the place to get some takeout food. It is usually filled with very few people. I was hoping no one would be there but when I reached the parking, I saw few cars parked there. I was deciding whether on not to go inside then I remembered another takeaway place few blocks away which was usually empty around evening time. I decided to try that place and see if I could get lucky and not find too many people.
I drove off again and arrived at the next takeaway place. I could only see one car parked and that boosted my confidence. While getting out of the car, I could feel my heart starting to beat faster again. I slowly walked towards the entrance.
As I entered there were about 2 guys and a couple waiting for their food. There was no one at the counter so I had to wait. I got anxious a bit but I kept my cool. As I stood at the counter I observed everyone was looking at their phones not caring who was around them.
Then a pretty young lady came to the counter to take my order. She obviously noted something and she looked at me from head to toe. I felt like I had never been observed so closely by someone and for so long , so it was exciting. She handed me the menu and asked what I wanted.
I looked over the menu and pointed to an item, hoping I didn’t have to talk. She nodded and told me to wait 5 minutes. I was relieved not to speak. She went in and I took out my phone and pretended to be busy. It felt like hours until my order arrived. Then I paid and left. I got into the car and drove back home.
After I reached my place, I quickly rushed inside the house. I could feel a sense of accomplishment and confidence in myself. It was quite adventurous and so much fun. I felt happy that my first time was quite nice.
The things I remember quite vividly is how different women’s clothes feel when you are out there. Although I had done a lot of in house crossdressing before, putting it all together and being out there is a different thing. The heels change your walk and posture, the fabric of dress feels different, bra straps that slide down, purse dangling around, Make-up on your face. It is no wonder that women’s things are honestly high maintenance than men. But I should not complain, it is the life I chose.
Submitted by Ruby