Tyler spent the next day lounging around the house in his new outfit, trying to to think about the fact that he, a boy, was not only wearing women’s clothing, but women’s clothing worn by his Aunt. The day really seemed to drag. Some small part of him hoped that when Sarah came home from work she’d have some new clothes for him to wear. When at long last she did return from work, she returned empty handed.
“Pajamas all day?” Sarah jokingly asked when she walked in.
“I didn’t know what else to wear” Tyler proclaimed defensively.
“I guess my closet can be a little overwhelming” Sarah said with some sympathy in her voice. “Look while I make dinner, why don’t you go get clean and put something new on to sleep in tonight.”
Tyler begrudgingly agreed, and headed upstairs to shower. After he was finished he wrapped himself in a towel and headed into Sarah’s closet. He intended on wearing another pair of pettipants since they were so similar to shorts, but to his disappointment there were no more where Sarah had gotten the last ones. He went down stairs to ask Sarah where he could find more.
When he got down stairs wearing his towel he asked Sarah, “Where kind I find more of the white shorts?”
Sarah cracked a smile and said “We really gotta stop with the whole asking me questions while you’re wearing only a towel.”
“Sorry” Tyler said while he blushed.
“It’s fine” Sarah said as she chuckled. “Sorry kid, I only have one pair of those. You’ll probably need to pick out a nightgown to sleep in”
“Nightgown?” Tyler exclaimed. "You can't be serious?"
“Yeah, guys used to wear them all the time” Sarah said. “They’re in the back left of my closet, pick anyone you want. Oh and please don’t forget to wear some fresh underwear too”
Tyler was dumbfounded, but really couldn’t think of what else to say, or any other alternatives. He turned to head back up to Sarah’s closet and found her collection of nightgowns. They were many colors and lengths. Tyler flipped through all the long feminine nightgowns to try and find the least feminine one. He picked a long blue one in a similar material to the pettipants. To his disappointment it had embroidered flowers along the neckline but he liked that it seemed the least overtly feminine. When he went back to the panty drawer he lingered a bit longer to look at all of the options. There was a cornucopia of colors and materials all laid out before him, and although his instinct was to choose something plain, something drove him to branch out a little. He chose a style similar to the last pair he wore but this time in a shade of blue that matched his new nightgown.
Tyler slipped on his panties and like last time was impressed by how soft they felt. He then went and put the nightgown on over himself. In addition to the soft nylon material feeling good bruising past his panties, Tyler was impressed how it actually felt pretty good covering his whole body. He found himself slowly rubbing his hands over his chest to enjoy the sensation. When he saw himself in the mirror however he came to his senses. “He was wearing a nightgown! It was so embarrassing!” Tyler thought to himself. He headed back downstairs in a huff.
“You went with the Miss Elaine, cute!” Exclaimed Sarah as Tyler marched down the stairs.
“Not really” responded Tyler as he sat down at the dinner table.
“Sorry it’s not your cup of tea” Sarah said as she carried over their dinner. “But you gotta admit, it’s pretty soft right?!”
“Yeah I guess so” sighed Tyler as he looked down at the blue frock he was wearing.
As Sarah walked around Tyler to sit at the table she jostled his hair and said, “Come on, it’s not so bad”.
After Sarah sat at the table the two began to eat their dinner and make small talk. After dinner they watched some television and then eventually Sarah headed off to bed. Before she left however she turned and as if she had one last thing to say.
“Hey look, I’d rather you not spend the whole day lounging around in my sleepwear. I’ll try to find something simple in my closet for you to change into in the morning, okay?”
Tyler wasn't quite sure how to respond. He slipped out an “I guess that's fine?”
Before Tyler could think of any follow up questions, Sarah responded with a quick “sounds good, have a good night!”
Chapter 1<----->Chapter 3