Marching Orders

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Josh always feared getting caught, but the urge to cross dress was simply stronger. There would be other urges before the day ended and Josh would no longer fear getting caught.

 
Marching Orders

By Mary Beth Sanford

 


 

Memorial day and the parade! It was today! Josh jumped out of bed and nearly fell moving to the calendar on his desk. It was today. His clock said six, his landlady had mentioned dressing at six thirty so they could leave the house by seven thirty.

The parade actually started at nine but that extra time, she had noted, would give them a chance for breakfast. Josh looked at the dress and slip on the back of his door and smiled. He shivered some as he picked up the ruffled bloomers he'd wear under it. Those he held for a moment as he looked over at his cute little girlish Mary Janes.

Another shiver at the shoes and panties. Only those watching him would see the bloomers ruffles and ribbon bows or his shoes because of his petticoats. He was almost faint as he made his way to the bathroom. Josh was playing the role of his landlady's granddaughter today. The water grew hot quickly and bubbled as he poured the bath beads in.

"The rest of that outfit is where that slip was!" His landlady had said catching him stepping into the petticoat. It had fallen from the hanger that held it while Josh was cleaning the attic. It took a few long minutes to decide to try it on and both feet were already inside the waist when he'd been caught.

His landlady had laughed but only slightly so as she had him bring the slip up to his waist. It wouldn't do not wearing panties she'd said moving to the closet. Little Bow Peep's panties she'd noted handing them to Josh as he stood there. The dress, once it was on, was very short but then again Josh, at eighteen, was ten years older than the owner had been.

She would fix that she'd noted as she had him sit to try the shoes on. They were a little snug but those too fit and before long she was tying his bonnet on. His feeble protest that he wasn't into such things brought another laugh since he was already trying on one of those things when he'd been caught.

The rest of that day was spent in trying on the rest of her nieces costumes and play outfits. It wasn't until the afternoon that Josh understood what "she would fix that" had meant when she showed him the diaper and plastic pants. Her granddaughter was a bed wetter and now, it seemed, so was Josh.

Josh looked down at his diaper and plastic pants as the tub filled. He'd been wearing those at night since that day and smiled at that. He wasn't into diapers and plastic panties either he mumbled as he slowed the flow of water and stepped out of his wet diaper and baby pants.

Josh wasn't into any of the things he'd begun doing a month ago, but his landlady was. She, he discovered loved all of those things and more when he was in them and from that day forward he was in one thing or another. Turns out her mother's mother loved dressing her son as a girl and so did her mother. So it was only natural that Josh's landlady would enjoy the same things.

Unfortunately Josh's landlady had only girls and while putting girls into fancy dresses was wonderful it was nothing compared to dressing boys up. Josh's landlady had loved dressing her brother up and a lot of that because he didn't. Josh, when she caught him, started protesting in that same way and that was as big a turn-on as her dressing him.

Fortunately for Josh his landlady knew exactly what it was that made a lot of boys dress as girls. She started showing him some of the advantages of cooperating with the baby oil and powder. Josh closed his eyes then and only opened them when he stood for his slip and dress. The diaper and those plastic pants now his. Everything was his since he was the niece now.

"You started your bath?" Josh's landlady asked from the other side of the door.

"Yes ma'am!" Josh said picking up the lavender razor for his legs.

"OK, call me when you need to be dried and diapered!" His landlady said.

"Yes ma'am." Josh answered with a mischievous smile.

Hugs
Mary Beth



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