My Summer With Aunt Sarah Chapter 2

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

An Excellent "Lost Bet" Crossdressing Comic

 Hello There,

    I was browsing reddit yesterday and stumbled up this excellent comic featuring crossdressing. The comic is by artist Agreeable_Swim_6551, who has a Patreon where you can see more of their fantastic art. The comic features a young man at a Halloween party who has lost a bet and been forced to crossdress. Loosing a bet and being forced to crossdress is a one of the most common story threads about forced crossdressing; and this comic does it exceptionally well. 

    Wasn't that so cute!! As soon as I read that comic I knew I had to feature it on my blog! Finding that special someone who is accepting of your desire to dress femininely is always the dream! Jake is quite the lucky girl!

Click here for the "Adult" bonus panel.

-Carly

My Summer With Aunt Sarah Chapter 1

Sarah worked Monday through Friday at her law firm and wouldn’t get home until around 7. So Tyler spent most of his days lounging around the house. He spent his first week playing video games online, reading, or watching the occasional movie. When Sarah got home from work the two would eat dinner together, watch some television and then Sarah would head off to bed for the night. When the weekend finally arrived Sarah spent her time exercising, tidying the house, doing lawn work, and most importantly relaxing. But given that she had Tyler staying with her, on Sunday they went out to see a movie and get some lunch. Once Monday returned Tyler got back to his normal routine of lounging.

That night while Sarah started her nightly ritual of showering, pampering herself, and choosing her outfit for the next day, Tyler did a load of laundry. Being that he’d only brought a little over a weeks worth of clothes he was out of clean clothes to wear and needed to run everything through the washer. Sarah had a fancy washer/dryer combo with all sorts of confusing features. Tyler did his best to navigate them and ran his clothes for a cycle while he showered. When he returned to take his clothes he was in for quite a shock. He immediately noticed that something was wrong, all his clothes seem to have shrunk in size. After trying them on his suspicions were confirmed nothing fit anymore. To not potentially walk in on her, Tyler texted Sarah his problem so she could come down and look at the washer to determine what was wrong. Of course he was a little embarrassed that he was standing in her laundry room with nothing more than a towel on, but what was he going to do. 

Sarah came down in a pink satin bathrobe with a distraught look on her face and said “They could not have all shrunk?” 

“Look, they did!” Tyler said in an annoyed and distressed tone. 

Sarah looked at the washer and said, “I’m so sorry, I should've told you how to use this stupid thing. You’ve got it turned up way too high”.

“Well I guess I can just sleep naked tonight” Tyler said with a sigh.

“Absolutely not!” Sarah responded. “I’m not having your naked body all over my clean bed sheets”.

“Well what do you want me to do? I don’t have any clothes that fit right now?!” Tyler exclaimed, obviously annoyed with the situation.

“Well….” Sarah said trying to think of a solution. “I have work the next four days, after that I’ll buy you new clothes. In the meantime you can just borrow some of mine”

“Yours?!” Tyler exclaimed 

“Look it’ll only be for a few days, and I won’t tell anyone” Sarah said sweetly. “I just don’t want you to be nude for a whole week.”

Tyler was visibly not a fan of the idea, but he couldn’t help but recognize that Sarah was just trying to help remedy the situation. Tyler also knew there was no way that she was going to accept him being naked around her nice clean house. So at last Tyler agreed and Sarah took him up to her room.

“Sorry I don’t really have a lot of boyish stuff in here, but I’ll let you choose what you want to wear.” Sarah said, gesturing towards her vast walk in closet of clothing.

Tyler, looking completely lost as to where to begin, asked Sarah “Do you have like a t-shirt and shorts I could just wear?” 

“Not really” Sarah said with a pondering look on her face. “Here these are kinda like shorts” Sarah said fishing out a pair of white nylon pettipants. She then headed over to a hanger with a bunch of camisoles on it and pulled of a black one. “This is about as casual a top as I have, just ignore the lace trim on the top”.

Tyler took both items from Sarah, said thanks in a downtrodden tone and went to leave her room.

“Hang on” Sarah said. “You can’t sleep in those without underwear on!” 

“What?!” Tyler exclaimed as he turned back towards her.

“I don’t want your boy bits all over my nice clothes. My panty drawer is over there, go pick something out!”

Tyler was tired and feeling defeated, so he walked over to the panty drawer and opened it. There were rows and rows of neatly folded panties of every color and material imaginable. He quickly grabbed the simplest black pair he could see and went to leave. Just as we was walking out he felt a hand on his shoulder.

“Thanks for being a good sport about all this, I’m sorry I can be a little anal about trying to keep things clean” Said Sarah as she hugged him. “Alright then go on, off to bed. And don’t you dare sleep naked in there” Sarah said with a sort of half joking tone.

Tyler quickly headed off to his room. He placed the clothes down on the bed and took his towel off. He sighed and picked up the panties. Unfolding them revealed the Victoria’s Secret logo on the front. He couldn’t help but cringe at the sight of it. Sighing in defeat again, he slipped them on. To his surprise they were actually quite soft and comfortable. Continuing this trend, so too were the pettipants. The smooth nylon material felt nice brushing against his legs and panties. Lastly he slipped the camisole on. Sarah was right he did have to try and ignore the fact that there was flowery lace trim now running along his chest. Tyler tried his best to not think about any of it and got into bed for the night. He hoped now just for a good night of sleep

Prologue<----->Chapter 2

Getting Some Crushing News...

Hello There,

    I figured I'd update you all with something going on in my personal life. I've been hit with a massive financial set back, basically costing me tens of thousands of dollars in the next year and a half. It is going to be a massive struggle to get through this period but I'm determined to do so. 

    That being said almost all activities that require financial support are put on hold, that includes girl time unfortunately. I won't be able to afford new outfits, wigs, costumes, make-up or accessories any time soon. I'm pretty crushed about the situation honestly. 

    I'm hopeful that this financial hardship may lead to a new opportunity to make more money however, so once I'm over this hill hopefully I'll be investing even more money into Carly's lifestyle. In the meantime content will continue on this blog, and I'm sure I'll still be getting dressed up every now and then. Thank you all for bearing with me during this difficult time.

-Carly