How I started Crossdressing and Fell in Love with It !

I had a very normal childhood as a boy. I was quite active, played games with my friends and fooled around a lot. I have been quite skinny since I was young but that didn’t stop me from playing sports. I was really good at basketball.

After I moved out from my parent’s house to start my college years, life was great. I had good friends and a cute girlfriend. I was really into rock music and I started growing my hair long. I also joined a band as a singer and we would play at a local pub on the weekends. It was pretty fun.



I also used to work in a departmental store part time and one day as I was stacking up some items on the self. A lady came up to me and asked me ” Excuse me miss, can you tell me where I can find some tissues?” I was confused and a bit embarrassed. Did she think I was a girl? I had my hair in a pony tail, maybe that was why she took me for a girl. I told her I was actually a guy and showed her the section where she could find some tissues.

She apologized realizing her mistake and complimented me that I had pretty eyes and lovely hair. “You look so pretty my dear, I really thought you were actually a beautiful girl.” Those words struck with me the whole day and made me wonder if I really looked feminine. I was too embarrassed to tell this to my girlfriend or friends.



A few weeks later, I broke with my girlfriend. I found her cheating on me with some other guy in my college. As days went by, I was sad and lonely. I didn’t feel like doing anything else so just stayed back in my apartment after college and played video games all night. One day as I was going through my closet, I found some clothes of my ex-girlfriend. She used to stay over  at my place quite often when we were together, so she would bring some of her clothes and put them in my closet. I completely forgot about it.

I took out the clothes and there was a bra, two panties, one white top, a denim skirt and a yellow mini dress. I was confused what to do with them now. Suddenly I remembered the incident at work where a lady confused me for a girl. Would I really look like a girl if I dressed as one? I decided to give it a go.



I don’t know why but I didn’t hesitated at all. I got undressed and first put on the bra and panties. I had some trouble putting on the bra but it did fit me and so did the panty. The fabric was so soft and it felt pretty good. It was getting more exciting now.

Then I put on the yellow mini dress and let my hair down. I had shaved that morning and when I saw myself in the mirror, I was shocked. I did look like a girl. The transformation was pretty convincing and I felt a strange feeling of satisfaction.



By natural instinct, I twirled around in the dress and tried some girly poses in-front of the mirror. It was weird but I really enjoyed it. I felt quite girly at that moment and wondered if that’s how girls felt wearing cute dresses and outfits. I walked around my apartment in my new form and it was so exciting and fun. It was a complete new sensation for my mind and body.

Later that day, I went on the internet and did some research. Then I found out about crossdressing and crossdressers. I was pretty curious about it. I must have spent so many hours that evening checking out videos after videos of crossdressers and male to female transformation clips. It was all so appealing to me somehow. I knew my life was going to be different now and Sophia was born.



Next few days, I was glued to my laptop, looking at beautiful crossdressers and reading male to female transformation stories. I was hooked. I had no idea guys could look so beautiful as girls and there were even crossdressing services that offered makeover services to guys. It all seemed so interesting to me and my curiosity to try new things grew even more.

I started searching for crossdressing tips and brought myself some makeup, pantyhose and high heels. Since I live alone, it was easier to experiment with new things and I enjoy the privacy. When I wore pantyhose for the first time, it felt so good and it was the same with high heels, they felt so amazing to wear and made my legs look so sexy. I was completely addicted to them. Over the next few weeks, I order more clothes, lingerie, makeup products, hair wig and a pair of breastforms. It was a game changer.



I started crossdressing more frequently and I would spent more time dressed as a girl when I was in my apartment. I really enjoyed playing the girl and expressing my feminine side. It made me more relaxed. I would spent hours getting ready and taking photos and videos of myself. I began to understand that there was no turning back for me.

Slowly with practice, I  started getting better at makeup and my transformation looked much better. I was also getting much better at styling myself and trying out different looks. Whenever I cross-dressed, I wanted to look as feminine and passable as possible. I realized it took so much effort and time. But I loved every bit of it.



Now, my closet is full of women clothes – skirts, dresses, lingerie, cute tops, leggings, high heels and also a cabinet full of makeup too. With all these pretty things, it so much fun to transform myself into Sophia. I love picking an outfit, getting myself ready, doing my makeup and after my  transformation taking a lot of photos and videos of myself to post in social media. I love it and its feel really good.

Through the internet, I have made many crossdresser friends and joined many crossdressing groups. Its nice to share my crossdressing experience with others who are like me. There are still so many things I want to do as a crossdresser like going out in public in daytime, shopping all day in my girl mode, hanging out with my crossdresser friends at a bar or some restaurant, dating a girl who will accept my crossdressing etc. For now, I am happy with the person that I am and crossdressing has helped me so much to take care of myself and give my life a new perspective.

Submitted by Sophia