I didn’t expect it to go this far with my cross-dressing. Really, I didn’t. It started with something small—just a little experiment to see if people would actually give more attention to me. Not Tyler, the guy I show the world, but Tina, the version of myself I only allowed to exist in private. Tina, with her confident smile, beautiful hair, curvy feminine figure, extrovert nature, and clothes that made me feel a lot more alive and free.
I am an average looking guy, I am just 5 feet tall and have a petite body. I have been an introvert since childhood and I did have hard times talking and connecting with other people around me I was alone most of the time and that led to me to cross-dress at one point. I tried on my mother’s party dress and high heels just out of curiosity. Everything changed after that. I fell in love with crossdressing and started to enjoy expressing my feminine side. I would cross-dress occasionally and keep everything to myself till I finished school.
When I started college, I stopped cross-dressing for a while. I was mostly occupied with taking classes and work. I found a lovely girl at college who after some time became my girlfriend. I was happy and doing good. But things took an unexpected turn and my girlfriend broke up with me. I was pretty hurt, lonely, and depressed. We were in a relationship for more than 2 years and it really got me down. I started skipping classes and work. I was in a really bad shape physically and mentally.
One day as I was going through my wardrobe, I found a dress that belonged to my ex-girlfriend now. Something triggered inside my head and I just wanted to put on the dress so badly. I instantly dropped all my clothes and put on the dress. Wow, the sensation was incredible. It was a black bodycon dress without sleeves and I didn’t imagined it to hug my body so perfectly.
I went to check in the mirror and my body looked so feminine and pretty! I was hooked with how I looked and felt. I must have spent hours that day just looking at myself in the mirror and admiring my feminine self.
After that, I started to cross-dress a lot and it helped me to cope with my loneliness. I started buying new dresses, makeup, wigs, lingerie, and shoes. I wanted to look and feel as feminine as possible.
Gradually, I would spend almost all of my time as Tina inside my apartment. But as weeks went by, I started feeling lonely and separated from the rest of the world again. I felt like a trapped bird inside a cage. But at the same time, I didn’t have courage to venture out in public because of the fear of getting caught.
Then, one night as I was scrolling through social media, I saw a crossdresser who was streaming Live on TikTok and interacting with other people. There were so many live comments from other crossdressers and admirers. Then it hit me, I could just connect to the outside world virtually while staying in the comforts of my apartment. The idea of exposing myself as a woman online to the rest of the world felt incredibly exciting. I could finally connect with people like me and maybe even find love.
I decided to build new social media profiles as Tina. For the next few days, I spent hours and hours engaging in social media platforms and also started posting my cross-dressing photos and videos. At first, there was barely any interaction from other people. But I kept posting daily, joining groups, sending invites, whatever it took to connect with other people.
Then one morning, as I was scrolling through my social media, I was shocked to see that one of my cross-dressing video was getting a lot of views and my account was blowing up with so many followers. I was so happy and excited at first but I started getting nervous with how fast things were picking up. It was getting too much attention.
At that point, I feared that people that knew me might see the video and I could easily get exposed. I started to panic and deleted all my photos and videos from social media. I got really terrified.
For few weeks I didn’t dress up at all. My desire to dress up was overshadowed by my fear of being exposed and humiliated by people I know. It was quite a frightening experience that took me some time to recover. Then one night as I was cleaning things on my laptop, I stumbled upon a video of me cross-dressing and in the video I saw how much fun I was having. I realized this was who I am and I would never be happy by suppressing my feminine urges.
I went back on social media and this time I started to post more discreetly and connect with limited people only. Then one day, I get this request from another crossdresser, Natasha and her profile looked great.
We connected and started sharing stuffs together. She was a closet crossdresser too and so was I. As we started getting closer and more comfortable talking with each other, I asked her where she lived and it turns out she lived only half an hour drive away from where I lived. I was shocked and I told her about it. No surprise, she was equally shocked. What were the chances for this to happen? We both laughed with excitement. We could do many things together now.
Natasha asked me if I would be interested to meet her and maybe dress up together. I was excited but also nervous to answer that question. I told her I would think about it.
That evening, I put on a cute red summer dress and black sheer pantyhose, got myself fully glammed, and planned to take a lot of videos. As I was shooting a video, I get a call from Natasha. She wanted to know a few things about the new lace wig I had just brought online. I gave her the info and we talked for a long time without even realizing. It was nice talking to Natasha while I was fully dressed. It felt like two girlfriends talking to each other!
After I hung up, I realized that it was lovely to finally have someone to talk to and Natasha was amazing. It would indeed be really nice to hang out together in person and share moments as Tina. I knew there wasn’t going to be another opportunity like this where I could actually meet with another crossdresser.
I decide to meet Natasha. When I told her I was also interested to hang out with her, Natasha was quite thrilled. We decided to meet at her place and dress up. She lived alone as well. We picked Saturday afternoon to meet up. I was so eager and anxious!
I was talking with Natasha every day now and we knew a lot about one another. We were really becoming good friends. We planned very carefully what we should do when we meet and I wanted everything to be perfect.
As the day came and I left the house with a bag full of my feminine things in my car, my heart was beating faster than usual. I couldn’t believe I was really going to do it. The drive went by so fast because there were so many things going in my head at that moment.
As I reached Natasha’s house, she was waiting for me outside dressed in her normal male clothes. He looked more handsome in real. He greeted me with a smile and I didn’t feel nervous anymore…
Stay tuned for part two…
Submitted by Tina
