Brian is all smiles as he takes a picture wearing his sisters new gown for the spring formal. It was Saturday morning and he had the house to himself for the day so he proceeded to do what any 14-year-old boy would do. Brian made a beeline to his sisters room and immediately striped of his shorts, underwear and shirt. Knowing his sisters wardrobe probably better than her, he already knew what bra and panties he wanted to wear. After slipping on the light blue low-rise nylon panties he reached into the back of the draw for his favorite bra. It is not fancy or anything, but rather a plain white bra with a small pink bow between the lightly padded cups. Although technically it is his sisters first bra, in actuality it was his first. He remembers vividly the day 3 years ago his mom brought it home from JC Penny for his sister. She was 12 and wanted no part in wearing a bra, so there it sat unworn on top of her dresser. After 2 days Brian couldn’t take it any longer, walking by her room and seeing it there begging to be worn. Finally he gave in and when no one was around he snatched it up and scurried to the bathroom. He studied it carefully then slowly put it on. Brian was amazed how it looked, he couldn’t take his eyes off that pink bow, and he found himself tracing the lines of the cups as they fit so nicely on his chest. When looking down at his chest he loved how the cups seem to give him a small bust line, and looking in mirror in profile seemed to confirm it, Brian now had “little boobies”. A term his mother had used when talking to his sister about the bra. When he heard his sister come up the stairs he stripped off the bra and hid it in the back of the vanity. For the next two weeks Brian wore “his” bra every chance he could, even got brave enough to wear it to bed one night. Then one morning as he came down stairs he heard is mother asking about the bra. His sister said she hadn’t seen it and assumed that she had returned it because she wasn’t going to wear it. His mother said she never touched it. Brain was in a panic, he quickly returned upstairs and pulled the bra from its hiding place and slipped into his sisters room and dropped it behind her dresser. Nothing more was said and a few weeks later he noticed his sister was finally wearing “his” bra. What a thrill it was to know he wore it first. As his sister got older that bra made it’s way to the back of the draw and is now only worn by Brian.
Once Brian finished reminiscing about the bra he pulled out panty hose and sat down on the bed to put them on. Once he smoothed them up his legs he went right to the make-up then started on his shoulder length hair. Anxious to get into the dress Brian just pulled back his hair, clipped it and pulled a few strands forward. Now onto the main event he thought… the most beautiful dress he ever saw…
Brian stood in his sisters room shaking as he took it off the hanger. He stepped into it, pulled it up, put his arms through the shoulder straps and let it settle across his chest. With some twisting and wriggling he managed to zip it up and couldn’t believe how wonderful it felt to wear the dress. He twirled and danced in front of the mirror and no matter how hard he looked he couldn’t find a trace Brian anywhere. While walking across the room in his stocking feet he thought, shoes, I need shoes. He tried his sisters, but nothing seemed to fit. A quick trip to moms room and he was wearing silver sandals with a small heel. Not bad he though as he made his way back down the hall in heels for the first time. After a photo session Brian decided to stay dressed for a few more hours, he headed downstairs to the family room to watch TV. Later on, with the family due back soon Brian headed upstairs to get changed. After kicking off the heels he went to unzip the dress and that’s when he realized he couldn’t reach the zipper! Once again he twisted and wriggled, but to no avail. He tried everything, even a clothes hanger to hook the zipper, but it was no good. Next he tried to just slip out of it, but it was too snug. The clock was ticking and mom and sis would be home soon. As panic set in, Brian realized he was stuck, stuck in his sisters’ new dress. Then it happened, he heard voices down stairs and ran to the bathroom and locked the door, his heart racing faster than ever. His mom called his name and through the door he gave a wimper of “I’m going in the shower”. Then he heard his sister come up and go into her room. He waited with his ear to the door to hear her leave, but all he heard was his sister opening her closet and dresser draws as if she was changing her clothes then soft foot steps getting closer to the bathroom. A gentle knock at the door and his sister said “Brian make sure you hang my dress up before you shower I don’t want it wrinkled”. Now Brian was not only panicked, but confused as well. And all he could say was “I can’t unzip it” then he realized he just told his sister he was wearing it. So when she said let her help he just opened the door and let her in. To his surprise she wasn’t mad and even complimented him on his hair and make-up…
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