Young Crossdresser Stories

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Young Crossdresser Stories
Featuring the fabulous and stunning Theona Staind from Romagna, Italy as our CoverGirl of the ...
▶ Femme name: Alana Grant ▶ Location: Peru ▶ How long you have been crossdressing ...
▶ Femme Name: Kristy ▶ Location: Louisville, Kentucky. ▶ How long you have been crossdressing : ...
Charming crossdresser Sylvia Greene shares with us her 5 most favorite outfits & style ideas. Outfit ...
Since childhood, I was always fascinated by women’s clothing. I used to secretly put on my step mother’s dress s and liked feeling pretty and girly. I tried to stop those urges but it only grew bigger.
As time went by, I started to sneak into my step mother’s room more often. I tried on her outfits, her makeup and shoes. So, every time I was going to be alone in the house, I would simply dress up. I started to buy outfits, lingerie, hair wigs from online stores and kept everything hidden in my closet.
One day my whole family was going on a trip to one of our relatives. I somehow managed to stay behind, saying I have a few tasks to finish. It was a great opportunity to take the whole house to myself. So my parents left and I was so excited to get dressed. I really wanted to wear a full make-up from head to toe and spend as much time as a girl.



I started getting ready without wasting time. I started with makeup, then undergarments and a pink bodycon dress that I recently brought in. I finished my transformation with a blonde wig, pantyhose and high heels. It was surprising to see my reflection in the mirror as a girl. I thought I looked cute.
After I was ready, I walked around the house in my new outfit. It felt really great. I took so many photos and videos that I did not understand how time passed. My parents were only coming back the next day, so I still had time to spend as a girl.
I had been out to the backyard several times dressed before, but it was only for a short time.
I walked into my backyard, feeling a little nervous if my neighbors saw it. So I looked around until I was comfortable. After confirming, I set up the camera and started shooting.



I noticed there was a boy looking after me from the neighbor’s house. I didn’t know how long he stayed there. I immediately panicked. My heartbeat got faster and faster. But I still tried not to overreact. I simply and slowly entered the house.
I was terrified that my cross-dressing secret would be exposed and my family would find out.
Soon the boy rang the bell and entered the house and kissed me. I was now a boy’s girlfriend.
Awesome story. I actually kind of liked that you ended the story with saying that you’d become his girlfriend and let the reader’s imagination fill in the rest of the story after you two disappear behind the closed door to experience intimacy in private. Loved it!
I loved it when he kissed me. It opened up a new world for me. Not only was I dressed as a girl, but now I was loved by a sweet little boy. Oh, what I could do for him! Mmmmmmm . . . . . .
Miss Roxanne Lanyon
I hope you DID do it for him. And he do it to you… Uh, for you.
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Best crossdressing stories shared by different crossdressers from around the world.

Featuring the fabulous and stunning Theona Staind from Romagna, Italy as our CoverGirl of the ...
▶ Femme name: Alana Grant ▶ Location: Peru ▶ How long you have been crossdressing ...
▶ Femme Name: Kristy ▶ Location: Louisville, Kentucky. ▶ How long you have been crossdressing : ...
Charming crossdresser Sylvia Greene shares with us her 5 most favorite outfits & style ideas. Outfit ...
My name is Daniel and I have been crossdressing since I was 15 years old. The first time I crossdressed was when I wore my mom’s dress and since then there was no turning back. I just fell in love with feminine outfits and getting dolled up. I started to dress in secret, wearing my mom’s clothes but slowly I lost interest in her clothes and wanted to wear cute dresses & outfits that girls around my age would wear.
As I grew a little older, my interest in ladies hosiery and undergarments grew quite a lot and I started to buy my own outfits online. I got obsessed with short dresses, sheer pantyhose, high heels and of course Makeup.
It was just me and my mom in the house and when she was away at work, I would just get dressed and take photos and videos of myself, walk around the house and do something girly. It felt so wonderful to release my feminine energy. I started to order a lot of things online like hair wigs, makeup and outfits. Eventually my collection of feminine stuffs grew quite big. I would keep all the stuffs hidden in my closet and locked it every time I went out.



As time passed, I began to dress up frequently, almost everyday. I started to experiment a lot with my looks. It did take some time to get good with makeup and watching tutorials in YouTube helped a lot. Now, I really wanted to step out in public as a girl and feel what its like to be outside. I began to fantasize about it more and more but I was also scared if my neighbors or people I knew, would recognize me and make fun of me.
My neighborhood had a lot of houses and to step out as a girl wouldn’t be so easy. So, I just tried to keep my crossdressing thing inside the house but the urge to go out was getting really intense, I couldn’t resist it anymore. Finally, I decided to go out of the house the next day, maybe up to the gas station and come back.
So the next day, after mom left for work. I took a shower, shaved and dressed in my favorite padded bra and lace panty, nude sheer pantyhose, a lovely white mini dress and 2 inch black heels. Then I applied some makeup. I kept it simple because I didn’t want to attract too much attention. I put on my favorite long black hair wig and a few accessories to wear – a clip on earrings and a simple locket.
I looked at myself in the mirror and I felt such a rush just looking at myself. My heart was racing and I could feel butterflies in my stomach. I started to get quite nervous about the situation, even though I had planned it in my head a thousand time. I peaked through the front window to see if there were people around. There were some neighbors hanging in their front deck and that made me even more nervous about stepping out.
I had to walk out the front door, to the garage , get into my car and drive off but it was going to take a lot of courage than I expected. I really felt very conscious about my appearance and the outfit that I was wearing. I must have looked into the mirror a hundred times to see if all my makeup and outfit was in place.



Then I noticed the neighbors were going inside their house and this was my shot. I took a big breathe, tried to relax my body and stepped outside. As soon as I stepped outside, I felt like the lights were so bright like I was walking on a stage. I was really conscious about every step I took, like it was happening in slow motion. I was too shy to look around so I walked straight to the garage, just focusing straight. Then I unlocked the car’s door, my heart pounding all the time.
As I get into the driver’s seat, I feel a little secure. The glasses of my car isn’t tinted so I was still fully exposed and I could feel it. I looked around and some people were walking down the street. I waited a while for them to pass, then started the car and finally left for the gas station.
I knew I had to get out of my neighborhood as fast as possible because I didn’t wanted to be recognized by someone. It was nerve rattling experience. I finally managed to get out of the neighborhood without seeing any familiar faces. Slowly, I start feeling a little comfortable and finally get time to acknowledge myself as a girl in the moment. As I drove around the streets, it felt like everyone I passed was just staring at me.
Every time I saw people, my heart would just start beating faster. Finally, I reach the gas station and there were many cars than I had expected. I thought a for second if I should just head back but I noticed the car was really low on gas, so I had to fill the fuel anyway. I then drove the car inside the gas station and joined the queue. I start getting more conscious again. I take out my phone and open the camera to look around because I was to afraid to look around.



Then the turn came for the car ahead of me. A lady got off from the car and I was nervous she would stare but she just minded her own business. When my turn arrived, I stepped out of the car, my heart was beating pretty fast. It felt like everyone had their eyes on me. I was standing over in full view of anyone to see.
I take a quick glance around and start filling the gas inside car. I noticed my hands were shaking quite a lot but I tried to calm down. After I was done, I took out my mobile and scanned the QR code to make the payment. It was 5 minutes for the whole thing to happen but it felt like 5 hours. I hopped in my car and drove off. I felt really great to be out in public like that. I knew I was going to be doing a lot more of this in the days ahead.
I got back to my house. Luckily the streets were quite empty and I just parked the car straight in the garage. Then I went to the front door, now a little more relaxed, opened the lock and stepped inside. I had a big smile on my face and I was so happy. What an amazing day it turned out to be. I had never experienced such excitement in my life. I went back to my room, sat down on the bed and tried to visualize my time outside. It was an amazing feminine experience and the I could feel the sensation all over my body. This was my first time out of the house and I loved it.
First time is always hard , its gets easier and you realise almost no one cares
That’s the biggest obstacle,realizing that nobody really cares..Let them stare if they want
Great experience, congratulations!! I remember my first time out. I got make-up from a professional, and he encourage me to go to a night club, at the LGTB friendly part of San Antonio. I used a short black dress, 3″ black shoes, and a blonde wig. My legs were nice and smooth. I just felt so cute and beautiful. I was so self confident that I was surprised!! I danced a lot, and had a great time!!
Wonderful I envie you for your courage
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(Author's note: I am writing this at the age of 27, on Monday 26th March, 2018. While it might seem to be a far-fetched account, what you read is true. Everything happened. While I try to write an unbiased entry of my life, some of what I have written might sound biased. I shall leave you, the reader, to make up your own mind.) -X- It started when I was eleven years old, my fascination for girl's clothing and crossdressing that is. I remember watching my older sister Katie walk around in skirts, dresses, blouses, all clothing that was infinitely better than anything I wore. It looked nicer, and when I hugged Katie, her clothes felt nicer against my skin, a lot nicer. There were times when I was left on my own in the house; my parents were either at work or out for the afternoon, and my sister was visiting her friends. I had freedom of the house, and since my fascination started, I had only wanted to do one thing: try on my sister's clothing. Many would have found it weird, an eleven year old boy wanting to try on girls clothing. I didn't really care at the time, I didn't know what kind of effects it would have on my future. At the time, when life seemed simple, I only saw it to be innocent curiosity that drove me to try on my sister's clothes. I didn't have any idea about the culture that followed it, I didn't know that men and women dressed in clothing of the opposite gender as a lifestyle choice, I would find that out much later in my life. When I entered my sister's room, I had an idea of what it would be like. Pink, filled with girly things ranging from dolls to make up to posters of boy bands and actors. I was definitely mistaken. At the time my sister was sixteen and going through her GCSE's. Her room was painted a cream colour, very few posters decorated the walls, shelves were filled with books and not dolls, and she had a large wardrobe up against the wall. That was my first port of call. I opened it up, and was stunned to see everything hanging up so neatly. My sister was a bit of a neat freak, everything was out of place, and it was rumoured that she could see from first glance whether or not something was out of place. I always believed that Katie had some sort of second sight for these things. It was proved right when I was first caught by her. Coincidently, it was also the same day I started trying on girl's clothing. When my parents and Katie had gone out, leaving me alone, I went into her room, and opened up Katie's wardrobe. I was instantly drawn to the dresses. She had a ankle length purple dress with straps. Now on Katie, it would have went down to her ankles, but when I tried it on, it went down to the floor, and even bunched up leaving a small tail of fabric. It didn't matter to me at the time; I simply stripped to my underwear and slipped the dress on over me. It didn't even need to unbutton the back of the dress. I looked at myself in the mirror that was placed on the inside of the door. My green eyes staring at the figure in the oversized dress. I felt the satin against my skin, and I liked it. I still looked like a little boy trying on adult clothes though, I had short brown hair back then, my parents choosing my hair cuts and how I looked for my time at school. I was going to take the dress and hang it back up to try on another item of my sister's clothing when I heard the door open. Someone stepped inside, and I was unaware who it was until I Katie shout up to me. "Rain! I'm home." she called out to me. I guess you are wondering about my name. Yes, I am called Rain. My full name is Rain Alexander Edmonds. My sister is Katie Elizabeth Edmonds and my mother and father are called Rebecca and John Edmonds respectively. I don't know why my parents named me Rain, it wasn't to do with the weather, I was born on Saturday October 20th, 1990, and according to my parents and sister it was a sweltering hot day so how Rain came into the conversation is a mystery. Anyway, back to the story. When I found that my sister returned; the first thing that went through my mind was a close resemblance of the words "oh crap" ran through my mind. I still hadn't changed out of Katie's dress and my clothes were strewn over the floor. I was going to be found and instantly my mind told me to hide. I immediately jumped into the wardrobe, and closed the door behind me. I remember that exact feeling when I was hiding from my sister. My heart was pounding, it felt like it was going to burst from my chest in a similar style to the Alien Quadrilogy. It would have solved some problems though, first off I would have been dead, and I wouldn't have to face my sister's wrath when she found I had tried on her clothes. She probably would have tried to resurrect my body and then kill me all over again for it. "Rain, where are you?" I could hear Katie from outside the room, and I hoped she would think I was somewhere else. This was the moment I found my sister really did have a second sight. I overheard her muttering that she had shut the door to the bedroom before she left, and I foolishly left it open. She knew I would be in her room, and the fact that my clothes were left out for all to see didn't help that. "Come on Rain, I know you are in here. If you don't come out until the count of five then I will be forced to tell mum and dad." she stated with a calm and methodical voice. Katie didn't raise her tone, she didn't have to. Knowing that Katie would tell our parents that I had been hiding in her room was really the only contributing factor of actually giving myself up. That and if I had continued to hide in her wardrobe, any chance of denying it would be useless considering I had left my clothes out. She started counting down, and I knew it was now or face the wrath of my parents. They would never have understood it back then, but it was likely that they had taken it down to a phase in growing up. The old 'curiosity killed the cat' saying. They would have forgotten it, and just told me never to do it again. I didn't even know how my sister would have reacted, but it didn't matter. I had to come clean and so, I pushed open the door to the wardrobe, and shuffled out into plain sight of my sister. For a moment Katie was quiet, she just stared at me. I was expecting her to start shouting and screaming at me, ordering me out of the dress and to get changed. I was definitely wrong. Katie hugged me. She stepped forward and wrapped her arms around me, a smile was on her face. I was dumbfounded, awestruck, amazed that I wasn't deaf from the screaming and shouting that I had originally expected. She in fact explained to me that she had really wanted a little sister instead of a brother. I didn't understand it at the time, but if I did fully take into account the words back then I might have been offended, but I knew she still loved me. Katie told me she was happy having a little brother, and when she saw me wear her dress, she actually liked it. Sure she was a bit annoyed that I tried her dress on without asking, but she didn't let it overshadow the clear fact we had just come closer together. I explained to her my reasons, why I was wearing her dress and hiding from her. The fact that I liked the look and feel of girl's clothing, and was curious to try something on. Katie asked me if I liked it, and I said yes. I truly did like wearing Katie's dress, and I told her that I wanted to try more clothes on. What she did next definitely surprised me. She took the dress off me and hung it up, instructing me to get changed into my previous clothes. When I was finished, Katie told me to follow her down to the basement. Now at the time when I was eleven years old, I had in fact been scared of the basement. My grandfather told me stories of monsters in the basement, and I'm ashamed to say that I believed him to that point. It turned out that our parents had kept boxes of old clothes going back the years. Every outfit of value and importance was sitting in the cases. My first football kit. Katie's first ballet outfit. Both mine and Katie's school uniforms from school. Our parents had the odd habit of sorting things out into boxes with the ages written on, and it actually h
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