I have a few fun stories about me dressing up so let's call this an episode of Real Adventures In Crossdressing. This is a true account and I'm telling you up front it does not end up Penthouse Forum style so just relax and enjoy.
Back in March of 2006, I had been growing my hair out for a while and decided it was time to have some fun with it. It was March and I was also getting close to one of my twice a year Becky weekends. I decided I would try to convince a hairstylist to do something girly with my hair as a goof.
I picked a tiny salon near my house and set up an appointment on a Thursday afternoon. I sat in my car for about five minutes gathering my courage and working on my story before heading in. For any closet dressers out there you are probably very familiar with this. Spending time walking past a Victoria's Secret with your stomach in knots waiting for just the right time to go in. Thinking what if someone I know sees me or what if the salesgirl suspects I am shopping for myself. Thankfully, I'm more courageous now but it was one of those I feelings like I was doing something wrong. Anyways...
Once I'd gathered my courage to go in the salon the place was basically empty, and my stylist came up and introduced herself. She was a cute little 5'3" blonde who I was guessing was in her lower 30's. She asked if I was just here for a haircut and I decided to try my luck. I told her my "story" about how my friends wife kept bugging me about my long hair and wondered when I was going to get a permanent or braids or something. I was supposed to help him drywall later that day and wanted to surprise his wife by showing up with a girls haircut. She had a confused look on her face but said ok. She wanted to know if I had anything in mind and I told her she was the expert and to do what she thought best. She thought curls would be too old lady and suggested I have my hair frosted.
As I settled in she started mixing the hair color and explained the process. Never having had my hair dyed before, I was actually interested. We talked and I explained how I would just be getting it cut again tomorrow trying to make my backstory feasible. Eventually we just started making small talk. She asked where I lived and and where I grew up, that sort of thing. When I told her what high school I had attended she said, "Me too." She asked what year I graduated and it turns out the random stylist I found to give me a girls haircut was in my graduating class. I no longer lived in the city where we went to high school together, neither did she, nor was the salon in the same city. Random dumb luck. Exactly the kind of thing a closet crossdresser fears. Does she know my friends? Will she tell someone who knows someone I do? Luckily my graduating class was about seven hundred people. We asked several of the, "Did you know Tom? No?" "Did you know Kelly?" type of questions. We had run with different crowds and didn't seem to have had any classes together.
After she had about a hundred of those little tinfoil squares in my hair and brushed every other layer in hair color she put me under the dryer for about fifteen minutes. When I was done she made a big show about the big reveal and turned me away from the mirror. Of course, there was a mirror on the other wall but I need glasses to see far things anyways. Still, I closed my eyes wanting the surprise as much as she did. She took the foil out and turned me back towards her mirror. I was a little shocked not having been blonde before. It hadn't been styled yet but it was definitely blonde.
She spent quite a bit of time putting in some product and blowdrying plenty of body into it. I paid close attention to what she was doing because I would need to do the same thing over the course of the weekend. In the end, the back and top were very full. She set aside some bangs to pull forward and curl under. The photo shows my attempt the next day to get the same style she had done at the salon. As she finished up and we walked to the front of the salon she said she was glad I agreed to the frosting. Then she said and I quote, "This way you look like a proper young lady." Which was pretty cool and funny. If only she knew how appropriate her comment was.
I did see her again at our high school reunion about five months later. The haircut never came up, she was about three sheets to the wind and my parents had just passed away. She was very kind and told me she was sorry to hear about my parents. So I hadn't seen this girl in twenty years and here I had seen her twice in five months and the first time I had asked her to make my hair look like a girls. It just goes to show you, no matter how safe you think you are being, be ready for anything.
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