In Wonderland, Pt.1

When I was in high school I was always very camp, which was probably why almost all of my friends were girls. This was definitely why I first ended up crossdressing. I was sixteen and round one of my ‘girlfriends’ house for a few drinks on Halloween before we went to a house party nearby. I never much cared for Halloween, so just came as myself. When I came in they all sighed since I wasn’t in a costume, but dropped it fairly quickly. We sat having a few glasses of wine and waiting for the last of our group, Laura, when the doorbell rang and she arrived. Karen, whose house it was, went to the door to let her in and they both came into the dining room, Laura dressed as a bee in a yellow corset and tutu, I thought she looked beautiful. Then I noticed that she held in her hand what looked like a dress, a blue one.

The girls all grinned at me and Karen said, “We though that it was about time you started making an effort for dress up parties, so Laura brought her outfit from last year.”

“I’m fine as I am thanks,” I laughed, thinking that they were joking.

Karen took a step towards me and whispered in my ear, “I’ll give you a moment with Smith tonight.” Leila Smith was a girl that I had a huge crush on, and if anyone could give me a chance with her it was Karen. I sighed, and Laura quickly dragged me upstairs.

She told me to take off my clothes, which I did, and handed me a pink silk padded bra and a matching pair of panties. She then slid the blue dress over head, and zipped it up at the back. It almost reached my mid thigh, and felt very strange and tight on me. She brushed my shoulder length brown hair and pinned it back slight, tying a blue silk ribbon in it.

“What do I look like?” I asked her.

“You can look when we’re finished!” She replied, beginning to cover my lips in lip gloss before applying a pair of fake eyelashes and thick black eyeliner as the final touch. She then dragged me to the mirror, which I looked in. I was a brown haired Alice. The dress was blue with a white mock-apron on top, and the four suits of a deck of cards depicted on the skirt. Besides the dress, my face now looked like a girls. Not just a girl, a hot girl. I looked like a slut. 

“It’s just missing something…” Laura said. With a gasp of excitement, she went into Karen’s drawers and found me a pair of thick white tights and blue stiletto heels. I slid them over my legs and stumbled into the heels. I felt very self conscious walking back into the dining room dressed like this. They all said how pretty I looked and told me to pout so we could pose for pictures together. After the embarassment ebbed away I actually quite liked it. I felt sexy, really sexy, for the first time. And it was fun, I was getting an experience of the secret world that girls lived in and it was incredible.

The taxi came and took us to the party, which I was incredibly nervous to enter. It was okay though, as hardly anyone I knew was there, a lot of the people were older. I had been at the party for about half an hour and it was relatively uneventful, except for men whispering me and pinching my ass as they walked past. Then, Karen appeared beside me with Chris Smith, Leila’s brother. “Smith, this is my good friend Tilly,” she said. I was mortified. I tried to mouth ‘what are you doing?’ to her, but she clearly meant all along that she would get the other Smith over. 

“Hi, I’m Chris, how’s it going?” He asked me, holding out a big, strong hand.

“Hi, I’m Tilly, “I replied, hoping that the ground would swallow me up, “nice to meet you.”

He made small talk with me for about 10 fidgety minutes about what I liked to do and how I knew Karen and the like, before I interrupted him. I could see his eyes constantly flit towards my bra and was very aware of how very skantily clad I was. “Sorry Chris, I’ve actually gotta be home now, but it was nice meeting you,” I said.

He gave me his number and told me to call him, and I left to the street. I didn’t want to walk home in high heels and a dress clearly tailored towards being someones whore, but Chris did boxing in his spare time, probably knew that I wanted his sister and would’ve killed me on the spot if he had figured out who I was, or even just that I was a guy. I was so lucky he didn’t find out.

I staggered onto the street and started walking, when I felt an arm around my waist. It was Chris “I can’t let a girl like you walk home alone Tilly, come on.”

I could not believe it! I was so nervous. I couldn’t tell him to leave, so I would have to keep being quiet and polite and pretending to be Tilly. When we were on the corner of my street I told him that I didn’t want my parents to see him so he should go, and went to continue down the street, but he grabbed my hand and pulled me back. He brushed my hair, looked into my eyes and told me I was beautiful. I don’t know why but at that moment I closed my eyes and pointed my chin up, towards his, inviting him to kiss me. He did, and we made out passionately for several minutes. I was aware all the way through of my dress, my heels and the way they made my legs look and what a sissy I was being.

“Come home with me,” he whispered in my ear. Again, I don’t know why but I agreed. We headed to his house instead, I just loved the feeling of him holding me, having a big strong man protecting me and giving me affection. It was when we got to his door that I was nervous; he clearly wanted something I could not give him.

TBC 🙂