Halloween Stories

It started early in the afternoon, I removed all the hair on my legs and underarmes and shaved as well as I could. I then touched up and got the remaining stubble off and got dressed in male clothes, I had to go get something for Sylvia and then I came back. About 5 or so I went into her room and started on my face, she showed me how to apply the makeup liquid then the powder. I know now to let my face dry before putting the powder on so it doesn't get messy. I then colored my toe nails and fingernails a light purple. I let that dry and then worked on my eyes, I put eye shadow then the eye liner and then the mascara. I then put on blush and touched up areas I missed. I finished up with a reddish purple lipstick and then I asked Sylvia to leave, she put up a fuss and I told her I would take all of it off if she didn't leave so she did. I put on my corset, underwear, and black pantyhose. I brought a silvery glittery dress and put that on. I put on my black wig and black slingback pumps and checked everything again. The whole time she was wanting to come back in the room but I didn't let her. I told her I was ready and I got behind the door and she came in the room, turned around and couldn't believe her eyes. I told her I hadn't dressed fully ever. She was surprised that it would look that good, she had a few comments but most were good. I went out into the dining room and for the first time 3 people had seen me dressed as a woman. Sylvia's mom was more surprised than I expected. She said I looked really good, I would pass for a real woman. Her niece said I looked good and even walked like a woman.

Well we took pictures and most of them came out great but there were some I didn't like. After that Sylvia's niece had to go home but so she didn't have to take the bus they asked if I could take her. I said, "Dressed like this, I don't think so." They talked me into it and said it wasn't too far. Well it was pretty easy going out dressed like that when there were others around. I walked out like I belonged. I helped them get her bags in the car, a challenge in heels. I then drove off and got to 410, got on the access road and went to Highway 90. I chose a long route so I could stay out a bit longer. It was fun, I had a blast on the highway. I drove a bit more careful than my male self. I really did play out the part. I got to the interchange with 35 and merged on and continued to her exit. When we got there I helped unload her stuff too. I did like the sound of my heels on the concrete. I then got back in my car and headed back. I tried
dragging it out but I had to go to the bathroom and Sylvia was trying to get me to go to a public one. I said no, if it was outside maybe but I don't know. I chickened out. We got back home and I kissed her thanking her for helping me. She said I really did look good. We took some more pictures in 2 other dresses I took. I then took off everything wishing I didn't have to but I had to get up early to drive home for work. This was my first experience and I thought it was a good one.

Now on to Halloween of 2001.

I was on vacation from work and had taken the whole week off. On Saturday I went to the riverboat cruise in Austin. I stayed dressed and went to Sylvia's house in San Antonio and they both loved the dress I was wearing. I then went with Sylvia to Northstar Mall on Monday to have my photo's done at Glamour Shots. Halloween was on a Wednesday this year and it started out early for me. I got up about 10, shaved, and showered. I then fixed beans and eggs and after we ate, I put polish on my toe nails. I got dressed in a casual outfit and pretty much hanged around the house until about 5, then changed into a bright red dress. We went out and had dinner at Chelsea's Pub and Grill in a local mall. The waitstaff was great and the waitress even took our picture there. The only bad thing was that Sylvia fell off her wheelchair. I told her the good thing was that I was there to pick her up. We then went driving around and took some nighttime pictures that came out halfway decent. We then went home and took more pictures and I even made sound recordings of my heels on concrete. The night ended too quickly and I returned to guy mode again. I then went to my tri-ess meeting on Saturday.

 

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