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Growing up my high school had a womanless pageant every year. I participated all three years I could. I had been dressing for years in my mom’s things but the chance to wear clothes from a girl my age was a wonderful experience.
The first year the girl who helped me was a cheerleader. Her and her best friend dressed me up at her house for the trial run. The highlight for me was getting to wear her cheer uniform. They laughed and giggled the whole couple hours I was there. They settled on a simple navy crushed velvet dress. The event was kind of a blur hard to enjoy it when your trying not to enjoy it too much.
The second year was fun my neighbor dressed me that year. She was in my class since kindergarten and we were good friends she also dressed me my senior year. I wore a white dress with little flowers all over it. This was a similar experience to the year before.
The last year was when the big event happened. My mom decided I need a more formal dress since it was my last time…. or was it? She called around and found a few prom dresses for me. There was a green off the shoulder dress. It was cute but I barely fit. There was a blue long halter dress. I liked it but showed my shoulders too much. The winner was a multi colored sequined dress. It had a higher neckline so no cleavage issues and was just above the knee. All three were in my closet for a week needless to say I tried them on every night after everyone else was asleep.
My mom and my neighbor had planned to do a dry run the Thursday before the big day after work and school. Being a senior I got out at lunch. So I went home and of course had to try everything before they got to see it. I borrowed some of my mom’s panties and the longline bra they had decided would need. I stuffed with some of my mom’s knee highs and put on some of her pantyhose. I slipped on the sparkly heels I had borrowed from my neighbor she had worn in a pageant. I was fitting the wig my mom had gotten me when I heard a car door. I looked out and my mom was walking to the house . No time to change so I just meet her in the living room. She was shocked but took it in stride. She had gotten off early and had gone to the grocery store. She had me go to the car and unload them and put them away. She then checked me out. She made some adjustments and called the neighbor who came right over they proceeded to do my makeup and added some costume jewelry. This was 2 in the afternoon. The neighbor left and my mom had me help her cook dinner and talked I felt like a daughter. She made me stay dressed till my dad got home at 5. My little brother thought it was hilarious.
After dinner it got interesting. My mom helped me take off the makeup and put everything in a bag for the next day. She then helped me undress. The look on her face when she unzipped me and saw I was wearing her panties was priceless. She told me to put them in the laundry after I showered. I put everything else in the bag and hung the dress back up. I showered and returned to my room to find my mother waiting to talk.
She started by telling me she enjoyed our girl day but that it was a one time thing. Dont get any ideas. She then told me it was wrong to wear her panties and not to do that again. She didnt go into too much detail but I understood she didn’t approve of my actions. But at the same time she let me off easy. I think she knew I had been wearing her things for years.
All in all it was a memorable day the pageant wasn’t much to talk about my then girlfriend couldn’t believe I wore a prom dress and all but told me this was the reason we wouldn’t last. Me and my mom never have talked about that day but she loves to tell everyone now how pretty I was those pageants. My wife knows and we have talked about it. She thinks my mom knows that I still dress. Maybe one day I will come out to her about it.
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