After another night sleeping in feminine wear, Tyler expected to find yet another outfit laid out before his door by his aunt when he opened it. Tyler prepared to wear yet another of his aunts' dresses, but to his surprise there was no outfit, only a note. Confused Tyler picked up the note and read it.
Dear Tyler,
At this point I’m sure you’re sick of having me pick out outfits for you, (although you’ve been such a good sport about it)! Since at this point you know where everything is in my closet you can go ahead and choose an outfit for yourself! Feel free to try on anything you want, the world is your oyster. I’m excited to see what you pick when I get home!!
-Aunt Sarah
XXOO
He was instantly a little overwhelmed with the prospect of having to choose a new outfit for himself. But he took a deep breath and accepted his feminine fate, and walked into his Aunt’s bedroom. After entering her closet he began rifling through the racks of dresses, and as he did so he was hit with a nagging thought: they would probably look better with a bra. He also knew that wearing one would make Sarah happy. So he slunk back to her dresser and opened the bra drawer. There were dozens neatly folded and color coordinated. He started rifling through them to find a push-up bra, to create some curvature on his chest. He ended up finding one he felt was fine, a maroon push up from Victoria’s Secret to match his red panties. He slipped his nightgown off and put on his newly found bra.
But before heading back to the closet to choose a dress, he found his gaze returning to the dresser, he could always try some of those pantyhose too he thought. So he opened the drawer he had seen Sarah open and found himself a pair of pantyhose he thought might be ok. He then went to sit on her bed and took the time to properly put them on. They felt as good as he remembered, still smooth. He ran his hands over them for a few minutes and then headed to the closet.
There were rows upon rows of dresses of every kind, color and material. He felt a little overwhelmed. As he kept moving to her closet he eventually came across the section which had all of Sarah’s business wear. There were satin blouses and blazers, pencil skirts, and business dresses. Sarah had never offered to let Tyler try any of these on before. Since she did always look so good wearing them, Tyler’s curiosity was piqued, maybe he’d look good in them too. He picked out a combo similar to what he’d seen Sarah wear before, a blue satin blouse, black blazer and black pencil skirt. The satin blouse felt amazing on his skin as he put it on. When he had the rest of the outfit on he walked to the mirror. Damn! He thought his body looked pretty good in that outfit! The pencil skirt really showed off his hips and booty!
Since he obviously couldn’t wear that outfit all day he walked back to the closet, and began disassembling his business outfit. He then returned everything he had worn to their spot in the closet and walked back towards the dresses. Tyler found a couple potential dresses, and finally picked one to wear. It was a sleeveless wine red dress. But when he tried it on he found that you could see the edges of his bra by the sleeve openings. Tyler was annoyed at this, he thought you really shouldn’t be able to see his bra underneath his clothes. So he stripped and went back to the closet. After putting the dress back he grabbed two more, just in case he didn’t like one of them again. He ended up trying both on to decide which he liked better. He looked fine in both, and in both you could not see the bra, so he wasn't sure which to choose. He figured he was already wearing one, so that one would be good enough.
When he went to return his other trial dress, a few more dresses caught his eye. “What was the harm in trying a few more” he thought. He brought three more dresses out to try on. He tried on dress after dress, and found himself enjoying this little fashion show he was having. How would they look on him, how would they feel to wear? He didn’t know why but he had the urge to keep going, dress after dress he tried on. Finally he must’ve tried on half of Sarah’s closet. Tyler didn’t know what had come over him.
While he was having his mini fashion show he, found his way over to Sarah’s dresser, and begun exploring the drawers he had never opened. Curiosity drove him to try each drawer. He found himself trying on slips, and bloomers, camisoles and swimsuits. When he arrived at the bottom drawer he found lingerie. His hands trembled slightly as he reached out towards the drawer full of lacy and silky goodness, and then proceeded to close the drawer. Another time perhaps.
Finally he’d gotten tired of the constant taking clothes off and on again. He finally settled on a long black maxi dress, with black and white zig zags on the skirt, and the underwear he’d chosen at the beginning. To his surprise it had been hours since he first entered Sarah’s room. He’d been so invested in his feminine fashion show that he didn’t realize how much time had slipped by. He had to admit to himself that he had been having fun, even if it was extremely abnormal fun.
After the extraordinary events earlier in the day, Tyler kept the rest of his day normal, and eagerly awaited Sarah’s return. When she finally did, at her first sight of him she clapped.
“You did it!’ Sarah cheered.
“Yeah I managed to pick something” Tyler responded.
“Ugh and good choice, this one is so soft, isn’t it?” Sarah asked while rubbing her hand on Tyler’s shoulder.
“Yeah, it’s pretty comfortable” Tyler responded.
“Glad you like it. But now that my weekend is finally here we can get you some new clothes tomorrow. Hope you had fun during your girl time week!” Sarah said as she took her shoes off.
“You know I kinda did” Tyler begrudgingly admitted, while cracking the tiniest of smiles.
Sarah immediately looked up with a HUGE smile on her face, “Really?!” she asked.
“I mean its certainly been interesting” Tyler bashfully responded.
“You know, buying you an entirely new wardrobe would be a lot of money, you could always just keep wearing my clothes if you wanted, I certainly have enough!” Sarah suggested.
The suggestion came as a bit of a shock for Tyler, obviously he had never considered such a thing. But he had to admit that he had fun doing his mini fashion show today, and he had been enjoying how close he’d been becoming with Sarah (which was only because of the situation he was in). At last he begrudgingly agreed.
Sarah literally jumped for joy when she found out. “That’s so fun!” she cried. “You know I always wanted a daughter” she said, kissing Tyler on the cheek.
The implications behind the comment made Tyler a little uncomfortable, but the kiss soothed worries, and had him looking forward to what new feminine fun may be on his horizon.
Chapter 4<-------->To be continued...