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My Recent Crossdressing in Public Experience

Author: Miss Samantha Pink

I woke up and just had an incredible urge to dress how I always wanted as a woman. It was so overwhelming and strong that I had no control over it, so I embraced it and went with the flow.

After sorting myself out but still in my boring male drab, I picked out a nice white bra, simple white top, underwear to match. Then a black figure hugging mini skirt to emphasis my curvy hips and slender waist with womanly bottom. Then some nude tights showing off my slender, shapely legs and my little cute 3 inch heeled boots. I wasn’t going to wear any makeup or my wig this time. Inside me something was telling me just to wear the clothes and be myself, a male dressed as a woman in public and don’t care what people say. I was super nervous at the thought of everyone seeing the real me, because I can normally hide my face behind my makeup and wig. This was different this was way out of my comfort zone. I pushed any negative thoughts out of my head and tried to forget about the fear and what people seeing me would say. I had a nice girly bag for all my stuff and it all fit in there nice ready to put on before heading out. I would put in on in my car in a secluded parking area away from prying eyes.

Heading to the car I decided to.go near my favourite supermarket and go in there fully dressed as a woman but without makeup or a wig. As I drove my nervousness started to creep back and become much more stronger and nearly made me lose concentration when I was driving. I pulled over in my car and composed myself saying that no matter ever I wear people will always judge me, so just be brave and wear what makes your mind inside comfortable, making yourself feel happy on the outside.

Once I was more calmer I drove to a lay-by near the supermarket. It was a place I had been to before and knew that no one goes by there and I would not be disturbed getting fully dressed in my female clothing.

I got out of my car and put a towel down on the ground by the driver’s side of my car. I had parked my car side on so if anyone did Walk past I had some time to get into my car and hid myself from view. I opened my driver’s car door and got in and started to undress. I have a small car but I have did what I done many times before so I’m used to getting changed into clothing in a small space. Today I was going to be braver for once as I knew it was secluded were I was parked, or so I thought.

I took all my male clothing off and was completely naked in my car with the driver’s door open and the comfy towel on the ground next to me to stand on. I got out, it was cold but it was a lovely feeling standing in just my birthday suit and feeling so alive and liberating. I had pulled the girly bag with me when I got out so it was within reach on my driver’s seat and standing there fully naked and shaking now because it was cold outside, I unzipped it to show all my female clothing ready to put on. I was so engrossed with the experience that I didn’t know a guy was right in front of me watching me with a big smile on his face. When I looked up and seen him I let out a massive girly scream and jumped into my car, wishing the ground would swallow me up. He came over and said don’t be frightened I like what I see and smiled even more. I gingerly looked at him and said I’m sorry that I’m naked and I hope your not offended. He said that he liked what he saw and had seen what was in my bag through my car window and would love to watch me put it all on if that would be alright. I stared to calm down and think things through and my female mind told me to go for it and you might get a treat at the end.

I said to him that is alright sir and with that I got out of my car and stood fully naked in front of him on my towel and carried on getting dressed up. He was complimenting my bum and legs and said that they were cute and I said thank you as I put on my underwear which he really liked. I was calming down a bit and he didn’t seem to be a threat to me and I liked what he said to me which was an unexpected surprise to my whole experience. He said he absolutely loved my legs when I slipped on my nude tights a leg at a time and I thanked him for his lovely comments about me. I put on my bra and noticed that my nipples were extra hard and sensitive, might be because it is cold or because a total stranger is standing there watching me totally dress up as a woman before his eye and is loving every minute of it. I put on my top and skirt and he liked those even more saying that I did have a very cute and pert bottom. I was loving this even more with him watching me and said to him that I’m sorry for screaming like a girl when I seen you but I didn’t expect anyone to be there and he frightened me. He said that he seen my car there before and wanted to approach me because he liked what he saw but didn’t know how I would react. He said he walks by all the time every morning and happened to notice my car, which was a nice surprise for him and he so wanted to say hello and say how lovely I looked. I thought were I parked a few time was secluded but obviously not. I was fully dressed and he said I looked lovely and was I not going to wear a nice wig and makeup but I said not today as I want to go to the shops as the real me and just be happy. Very brave you are said the guy and I thanked him and said that I have a nice treat for him being so nice to me and told him to get into the back seat of my car. He asked me why and said get in and close your eyes. He got in and I got in the other side and adjusted myself so my sexy sheer tights were close to him and told him in my best girly vice to pull down his pants. He couldn’t wait and pulled them straight down with his eyes still closed. I rubbed my tights against his legs and his little penis got super hard and I licked it all over and he came into my mouth in seconds and he groaned and was loving the experience. I told him to open his eyes and I was smiling at him and I gave him a big kiss on his lips and said thank you for helping me get dressed and loving what you seen.


I was going to go to the supermarket but after he left I had to go back home to get freshened up and hopefully I will meet him again but will be fully dressed next time and we could do so much more things together and maybe he would like to come shopping with me beside him and buy me something nice to wear and I give him more treats.

Related articles:

My First Makeup Experience 

My First Crossdressing Experience in Public – Part 1

My First Crossdressing Experience in Public – Part 2

My First Crossdressing Experience in Public – Part 3

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