Caught in Trail Maid Dress (Patreon)

(Reposting old captions here)

Hi my name is Micheal and I live in Mobile, Alabama. Here in Mobile we have a tradition of the Mobile Azalea Trail Maids who are 50 seniors who get to wear giant beautiful southern belle gowns. For as long as I can remember I've always had an interest in the girls and their gorgeous dresses. This year my sister tried out and got into the trail maids. So she got to become a trail maid and got her very own dress made. I was incredibly jealous as she got to wear and design her very own dress. One day I was home alone and incredibly bored so I walked through my house and eventually found myself in my sisters room. In the left hand corner there was a stand that had her  blue trail maid dress just sitting there. I immediately felt my heart flourish and before I knew it I had stripped right down into my underwear. I began taking the dress of the stand and setting it on the bed. Then I took the hoop skirt off and finally the pantaloons and bodice. The bed now covered in blue lace and satin. I looked down at my underwear and realized that wearing boys underwear just felt plain wrong so I took them off and traded them for a pair of frilly panties. Satisfied with my underwear I grabbed the pantaloons, pulled them over my legs and tied them off at the back. After that I grabbed the bodice and pulled it up and over my head. I caught my reflection in the mirror and realized something was missing. Taking a step over to the laundry basket I pulled out an old pair of socks and stuffed the bodice to make it appear that I had breasts. However I wasn't satisfied and found a blonde wig leftover from an old halloween costume. Next up was the hoop skirt which I put on the ground stepped into the middle and pulled it up before tying it around my waist as I had seen my sister do time and time again. Now with the hoop skirt on I noticed that I took up 8 feet in every direction. I also noticed how the hoop hypnotically swayed every time I moved. Finally it was time for the dress it self with I picked it up and tried to find the hole to put my head through after struggling for a bit I finally managed to get it down and over my head. I fluffed the dress up and made sure it sat nicely over my hoop. With the dress fully on I noticed just how much weight was around my waist but I loved every second of it. Now it was time for the finishing touches I grabbed the gauntlets and hat and put them on my hands and head with that I was officially dressed like a trail maid. I rushed over and admired how the dress made me appear to have such a small and highlight my feminine features. I felt the brush of the hoop skirt against my pantaloons everytime I took a step and loved the way the ruffles sat on my shoulders or how the bow rested on the small of my back. After striking some poses in the mirror and taking some pictures for future reference I decided to walk around the house. I loved how the hoop skirt swished and swayed with every step I took and just how dainty and pretty I felt in the dress. While dressed up time seemed to slow down and slip away so much so I didn't notice my sister come home. "What are you doing?" she asked shocked and surprised While I merely put a dainty gloved finger to my lips saying "shh, Don't tell dad"