When I was in high school, Stacy was my best friend and we were really close. We used to share everything and hang out a lot. One day at school, we got an assignment to write an essay on gender and society. Stacy asked me if we could work on it together and I said sure.
So, after school, we met in her house and started working on the assignment. As we were discussing about gender, Stacy suddenly asked me if I ever thought about what its like to be a girl or dressing up as a girl. I told her not really but joked I wouldn’t mind looking hot as some girls do.
She asked me if I wanted to experience being a girl for sometime? I was startled by her question and asked her how. Stacy replied she could give me a makeover and dress me up as a girl. I was surprised and nervous when she said that and replied I didn’t want to because it was a silly idea.
I could see the spark in Stacy’s eye. She was now fixed on giving me a makeover. She told me it was going to be quick and fun. She also promised she wouldn’t tell anyone of this. I told it was weird and I might feel very silly afterwards. She assured me that it was going to be a great experience and I would surely enjoy it. Finally after a lot of convincing, I agreed her giving me a makeover.
I was having a mixed feeling about what was going to happen next. Stacy was already super excited about the idea of dressing me as a girl. I really didn’t know what to expect. Stacy went to her closet and picked out a bunch of her makeup stuff. My face got red when I saw her picking out a red padded bra and panties from her drawer.
I told her there was no way I was wearing her underwear, it would be too embarrassing. But Stacy was already set to give me a full makeover. She told me the bra and panties were new and she hadn’t worn them yet . I tried once more to stop her but Stacy wasn’t taking no for answer and I realized I should probably get this over with sooner.
Stacy started first with Makeup. She made me sit in her chair and started applying all these makeup products on me. It felt so strange to me but at the same time I was feeling excited to see the end result. It took her around 30 minutes to finish with the makeup as I sat there with my eyes closed. To be honest, it was quite relaxing than I expected. When I saw myself in the mirror, I couldn’t believe how different my face looked, especially my eyes. Stacy was smiling watching my reaction in the mirror.
She told me she had a wig from last year Halloween when she went out as Wonder Woman. She took out a box from under her bed and got out the wig. Stacy then combed the black wig gently and asked me to stay still. She brushed all of my hair backwards first and then placed the wig over my head. Stacy screamed with joy and told me to look in the mirror.
When I looked into the mirror, I blushed so hard. It was really shocking to see that I looked completely like a girl now. I was really shocked. I couldn’t even look at myself without blushing. I told her it was too weird and told her to take off the wig. She said not until I dress up first. Then she told me to take off my shirt. I took off my shirt and she put on the bra on me and my cheeks went red.
She adjusted the straps of the bra and put on some napkins inside the cups of the bra to make it look like I had real boobies. The straps of the bra was giving me a tingling sensation and everything was so tight around my chest. The bra was padded and seeing myself with curves was really shocking.
Then she handed me the panties and a black mini dress, and told me to go change in the bathroom. I told her I wasn’t sure if I could do it. But Stacy already had her mind made up and she took me to the bathroom and closed the door from outside.
I started undressing myself. Then, I picked up the panties. I could feel my heart beat getting faster. I was going to wear panties for the first time like the bra I was wearing for the first time too. My body was shaking as I pulled the panties up. The fabric felt so soft and I couldn’t resist to check it out with my hands. I looked into the mirror and I couldn’t stop looking at myself. It was so weird but I looked pretty hot and it was turning me on somehow.
I was a boy few minutes ago and now looking at myself, I couldn’t believe how much I looked like a girl. I was wearing girl’s undergarments and it was such a different sensation. Stacy knocked on the door and told me why I was taking so long. Her voice brought me back to reality and I said be right out.
I put on the black mini dress. I loved how the fabric of the dress felt on my body. I looked at the mirror to check out the final look and I was still in awe that I could really look so beautiful as a girl. I felt like a complete different person and didn’t know how to react with all the new sensation I was feeling in my body and mind. Stacy yelled me to come out. I couldn’t believe I was going to let Stacy see me all dressed up.
I opened the door nervously and came out. Stacy screamed looking at me. “You look amazing! I love it!” she yelled. That made me even more nervous and I blushed hard. She gave me a hug and asked me how I felt being a girl. I was too dazed to answer. Then she started taking pics while I was telling her not to take any. She was giggling and taking more pics as I was trying to take away her phone.
Then all of sudden, the door opened and it was Stacy’s mom. She looked at both of us and then looked at me. “Hi girls, what are you upto? Who is this young lady?” she asked Stacy. Stacy looked at me and laughed. I was so terrified while Stacy was enjoying all this.
“Can’t you guess who this is?” Stacy asked her mom.
Her mom gave me a confused stare and I couldn’t even look her in the face.
“No, I don’t think I have met her before.” Stacy’s mom answered.
“It’s George!!” Stacy replied with a big smile.
“WHAT? ” Stacy’s mom was pretty surprised as well. “No way! Is that really you George?”
I nodded. I was so embarrassed now that Stacy’s mom also saw me like this.
Stacy told her mom about how she gave me a full makeover. Standing there while Stacy and her mom were talking and checking me out was so awkward.
“Isn’t he so beautiful as a girl mom?” Stacy asked her mom.
“Wow… he actually is. I would have no idea if I meet him on the streets like this. Well, looks like you have a new girlfriend Stacy!” Her mom joked and she gave me a wink. I tried to smile back.
“I am going to the market to grab some groceries. You gals be nice okay?” Stacy’s mom said as she left the room.
I was a bit relieved after her mom was gone. Stacy asked me if I would like to go out for a short walk dressed. I had enough surprises for that day and I said I wanted to change back. I changed back to my clothes and Stacy helped me remove the makeup.
I couldn’t stop thinking how crazy the whole experience was while I walked back home. When I got home and was changing my clothes, I realized I forgot to take off the panties and was wearing them the whole time. I couldn’t stop smiling thinking about what just happened. I called Stacy and told her. She had a big laugh too and told me to keep the panties. Dressing as a girl was certainly an experience that changed my life forever.
Now 6 years later I enjoy dressing up and going out as a woman.
Submitted by George