Tyler slept pretty well in his new nightgown. Sarah was right, he did have to admit “it was pretty soft”. After scrolling on his phone in bed for an hour or so he finally got out of bed and headed out of his room. When he opened his door, lying on the ground was a neatly folded dress and a note. Tyler picked up the note and read it.
Tyler,
Sorry I don’t have any clothes more appropriate for a teenage boy. I noticed you picked a blue nightgown, so I went with a blue dress as well. I hope you don’t mind it too much, I tried to pick a simple one. Thanks for keeping an open mind and indulging me.
Love, Sarah
Tyler was impressed by the penmanship; Sarah had obviously written it with care. Tyler had to admit to himself, he liked how much Aunt Sarah seemed to care about him, despite the extenuating circumstances. When he was done with the note he picked up the dress. It was fairly simple, light blue with small white dots, a v-neck and flutter sleeves. Tyler slipped off the nightgown and slipped on the dress. Other than a slightly different material they honestly didn't feel all that different to wear than the nightgown. It was breezy and did a little bit of swaying as he walked. “Another day in girl’s clothes” he thought as he let out a sigh.
Wearing a dress didn’t change his day in any way, he still had his usual schedule of video games, reading, and movies. As per usual his day didn’t get interesting until Aunt Sarah returned home from work. Tyler was walking into the kitchen when she returned home. At the sight of Tyler in the dress, Sarah smiled and walked over to Tyler and hugged him.
As she held Tyler close she said “Thank you for keeping an open mind”. When she released him she took another look at him, with a slightly puzzled look.
“What?” Tyler asked in response to Sarah’s puzzled look.
“Nothing, it's just….. That dress doesn’t look quite right on you”. Sarah responded, still visibly pondering Tyler’s appearance.
“Well yeah I’m a guy” Tyler said and chuckled.
“No it’s not that, anybody should be able to wear anything.” Said Sarah. She spent a few more seconds thinking and then said “I think it’s cause you don’t fill out the chest enough. A bra might help”
“What?!” Tyler quickly responded. At this point given that he was standing there in his Aunt’s panties and dress nothing should have surprised him. But now his Sarah wasn’t just suggesting wearing clothes to avoid being naked, she was suggesting wearing a bra to fill out his dress!
“Come on, it’ll be fun!” Sarah said as she grabbed his hand and started walking towards her bedroom.
Tyler couldn’t help but be whisked away towards the unending feminine nightmare that was Sarah’s bedroom. When they arrived, Sarah went to her dresser and rifled through it pulling out a black bra.
“Here this should help, It’s a push up with a lot of padding so it should fill out the chest of your dress a little bit better.” She said, handing it to Tyler. Before Tyler could retort with an objection Sarah asked “So what do you know about bras?”
Tyler who was planning on objecting to the whole situation pivoted to saying “Uhm, not much really”.
“So they’re for support and shaping. They can change the way a woman’s breasts look and feel on us” Sarah said proudly.
“Wow really?” Said Tyler.
“Oh yeah” responded Sarah. “Here ugh…” She said before thinking briefly. Sarah then began unbuttoning the red satin blouse she was wearing. “This is just for educational purposes”. Tyler could do nothing but sit there in disbelief as his aunt began unbuttoning her blouse in front of him. When she was finished she revealed the black and red bra she was wearing. Sarah began running her fingers over her bra as she explained: “So the straps help hold the breasts up which alleviates some pressure on our body’s as well as make the breasts a little less droopy”. Sarah then moved her fingers to the bottom band of the bra and explained “The padding in the cups helps push the breasts up and make them more pronounced”.
Tyler had to try his best to keep meeting his Aunt’s eyes as she was having a conversion with him, but he could not help but be impressed with his Aunt’s voluptuous breasts. When she was finished explaining she handed the bra to Tyler and asked him to try it out. Tyler was still in shock about the situation, he really didn’t know what to say or do. Here he was in his Aunt’s bedroom standing in her dress and panties holding a bra as she stood across from him wearing a tight pencil skirt and an open blouse with her bra covered breasts fully exposed. He was overwhelmed and sort of froze.
Sarah then said “Oh silly me, let me show you how to put it on”. She then walked behind Tyler, and unzipped his dress!
Tyler’s heart was racing. Sarah lowered the dress just enough to slip the bra straps through Tyler’s arms and connect the band in the back. She then put the dress back up and zipped it back up. Sarah then turned him and lit up with a smile.
“See that’s so much better!” Sarah cheered. She then turned Tyler and walked him over to the mirror. “The dress just look way more normal with some padding underneath don’t you think?”
Tyler still in a daze from before just responded with “Ugh yeah”.
Sarah chuckled and then kissed Tyler on the cheek. “Why don’t you head down and get ready for dinner? '' she said, and began to rebutton her blouse.
Tyler nodded and left the room. He walked out and down the stairs with the new tight feeling of a bra cradling his chest. He looked down as he walked and could see the visible curvature of what looked like women’s breasts on his chest. Tyler’s confused feminine haze lasted the rest of the night. He was fairly quiet and really only responded when Sarah talked to him. Finally at the end of the night she had him go get a new nightgown and panty set which he did and then headed off to bed.
As he laid there in bed he could not help but think of the image of Aunt Sarah standing there with her chest exposed. He found himself cracking a little bit of a smile. As he drifted off to sleep, enjoying the feeling of his nightgown brushing over his panties, he held his adoration for his Aunt close to his heart.