Confessing I am a Crossdresser to My Best Friend

For years I have been a closet crossdresser, trying on girls’ clothes secretly inside my tiny apartment. Ever since I started dressing up, my desire to look as passable as possible also grew. I enjoy dressing up and love feeling girly. My friends and family have no idea.

After many months of dressing up in secret, I started feeling a bit lonely and confused. Although, I didn’t feel the need to present myself as a girl all the time, I wanted to dress more openly and explore my feminine side. But time and again, it felt wrong to crossdress. I often wondered if it was sometime that I shouldn’t be doing at all. I never shared about my crossdressing with anyone until recently I confessed about being a crossdresser to my best friend Katie. 



One evening, while me and Katie were sitting in her room talking and the conversation somehow came to crossdressing. My cheeks went red immediately and my heart began to beat faster. She was telling me how crossdressers are usually mistreated by people, and everyone has the right to dress & express their true self.

I felt like she would understand me and it was the right moment to finally tell someone about my secret. It wasn’t easy, I felt like my heart was about to explode but I knew it was now or never, so I confessed to her.

I told Katie all about my crossdressing secret and how I have been secretly dressing inside my apartment, how confused I felt sometimes, how strong the urge for me to dress feminine was sometimes, and also the desire to go out in public as a girl. I could tell from her expression that she was pretty shocked.

I was really scared about how she would react. I knew it could make her uncomfortable but Katie was very understanding and she held my hand and thanked me for sharing it with her.



She told me “I really had no clue that you were into crossdressing. I have to say I am pretty surprised. You never showed any sign of interest in girly stuffs. I guess you are quite good at hiding your secret. Anyways, I am glad that you are following your heart and I am here to support you no matter what. “.

It really felt nice to share my secret with her. I was so relieved. Katie was really curious and asked me so many questions about my crossdressing. I was happy to tell her everything. It felt great talking with her and ask for her opinions as well.

Then she asked me if I had any pictures of me as a girl and if I would be comfortable to show it to her. I was quite nervous but I decided to show her, so I opened my phone and showed her some pics. This was the first time anyone was going to see me as a girl, so I was anxious to see her reaction. When I showed her some pics, she was amazed and complimented me that I looked great.

“If I was walking down the street and you were also passing by, dressed like in your pic, I would never know its you. You look so cute as a girl.”, Katie exclaimed. I blushed and she teased me for a while.

We had quite a long chat. Katie was really supportive and even offered to take me out shopping, help me with makeup or anything else I needed help with. I asked her if she would be comfortable with me dressed in front of her and without any hesitation, she said she would be totally fine with it.



I asked her if she could help me with my makeover and if we could go out in public together someday, even for a short walk. She agreed and told me we could do something like that in the coming weekend. I really felt so fortunate to have such a wonderful friend. I felt a lot lighter after sharing my secret with her.

The next weekend, I invited Katie to my apartment. I was so excited to have her help me with my transformation. When she arrived, I showed her my collection of clothes, lingerie, heels, wigs and makeup.  She told me I had a lovely collection. She suggested if she could select the outfit for me to wear that day and I said sure.

She browsed through my collection, then picked out a pink bra and panty set, a white midi dress with ruffles, a black shoulder length wig and a pair of black heels. She told me to put them on. It was exciting to dress up for someone for the first time.

Then I went in the bathroom and got dressed. I felt very nervous to come out and let her see me. I took a deep breathe and opened the door.

When she looked at me, I blushed.

“Wow, you look so lovely in this outfit. Should I help you with makeup next?” Katie asked me.

I nodded and then she started applying makeup. I was pretty dazed and the whole experience felt incredible. We had lots of fun, we laughed , talked about fashion, and she gave me a lot of tips. It was so nice to have her company.



After the makeover, she suggested we should do some photoshoots and we did. She taught me a lot about good postures and how to pose for the camera. I learned so many new things that day.

Then we cooked together and watched a movie. It was so lovely to be dressed and do all those things with Katie. When it was time for her to go, I thanked her for everything and we hugged. She told me we could go out next time and I said I couldn’t wait.

After that day, I have been out with Katie a few times now and we even went shopping one time. It was great. Now, I feel more confident about myself and I do go out in public once in a while and it is something that I really enjoy.

Submitted by Pete