After such an eventful evening the night before, Tyler slept very well. He woke up with a strange feeling of butterflies in his stomach, probably from the excitement of the night before. He got out of bed only to find another pile of clothes outside his room, this time with an added bra. He would have expected that he’d let out a sigh, but he found himself picking up the feminine wear without hesitation and heading back into his room.
Tyler laid out the dress and bra out on his bed. The bra Sarah had picked out was the one Tyler had briefly worn the night before. After staring at his outfit for the day briefly he slipped his nightgown off and picked up the bra. He did his best to put it on like Sarah had shown him, and once it was on he looked down at his now bra covered chest. He couldn’t help himself, he slowly raised his hands and squeezed the cups of his bra as though there were breasts that lie within.
After a twinge of satisfaction from the bra squeeze, Tyler turned to the bed to pick up the dress. It was a similar length to the day before however this dress was sleeveless, and the pattern was predominantly black with pink dots. He slipped it over himself and zipped it up on the side. Looking down the curvature created by the bra was very noticeable. Looking in the mirror it looked like he had breasts! He couldn’t deny his aunt’s point however, the dress probably wouldn’t have looked as good without the bra underneath it.
Tyler once again went through his day like normal, video games, television, reading, but he found himself constantly looking down at his enlarged chest. He didn’t hate how it looked. He liked breasts and now he had a pair he could look at wherever he went. It was quite the novel experience for him. Tyler also had to admit that he was excited to see Aunt Sarah’s reaction when she got home and found that he had indeed worn the bra.
Eventually the time came and Sarah came home from work. Tyler was on the couch playing a game on his phone when she walked in. The way her face lit up from excitement when she saw him wearing the bra was extremely evident.
“You wore it!” She excitedly proclaimed.
“Yup!” Tyler called back to her. “I figured I might as well”
“That’s so exciting! Doesn’t it make the dress look so much better?” Sarah asked as she put her handbag down.
“Yeah I mean, I guess it looks more natural” Tyler shrugged. Hiding the fact that he didn’t hate his experience all day.
Sarah lit up again with excitement. “That’s great, I’m glad I could teach you something new!” she said.
“Yeah, thanks for that” Tyler said. He then went to say something else but Sarah cut him off.
Sarah gasped “Should we learn something else new tonight?!”
Tyler’s heart immediately began racing, what did Sarah mean? Another lesson like when she showed off her breasts to her teenage nephew?! He didn’t know how to respond, he was both nervous and excited, what should he say? As he thought things over he looked up at Sarah who was excitingly staring at him. Her excitement was infectious and before he could really think things over he let out a “sure”.
Sarah clapped and jumped for joy proclaiming “Yay!! That’s exciting, glad you’re making the best of this situation. What do you want to learn about today?" Sarah asked as her excitement turned to intrigue.
Tyler was speechless, he didn’t know what to say, he agreed more or less on accident, he wasn't actually thinking about anything else he wanted to know. He began to panic internally, Sarah was so excited and he didn’t want to let her down. He looked to her for inspiration, she was wearing a black blazer, red satin tie neck blouse, and black pencil skirt. As his eyes continued to move down her body he locked eyes with her pantyhose and let out a question “what about those?” he asked and then lifted a finger to point at her legs.
“Pantyhose?” Sarah asked while looking down at her legs. She looked up with a beaming smile and declared “That’s a great idea!”.
Sarah walked over to Tyler and grabbed his hand, and once again began walking him to her bedroom. His heart began to race again, what will Sarah do this time, what will she make him do, why did he agree to this. Sarah’s excitement was infectious however, she practically skipped to her room, holding Tyler’s hand tightly. When they arrived Sarah had Tyler sit on the bed while she rummaged through her dresser.
“Ok pantyhose 101” Sarah said with a chuckle as she pulled out a couple pairs as a visual aid. “They're not really as prevalent as they used to be but pantyhose are worn to enhance the appearance of your legs, make em’ look smooth and polished and hide your blemishes. Some women also wear them for modesty, so their bare legs aren’t just out and about.” Sarah then handed Tyler one of the two pairs she was holding. She then continued her discussion by holding up the other pair in her hand and saying “And these are tights, pretty similar to pantyhose just with a slightly thicker material. You might wear these instead of pantyhose if you’re trying to stay warm, know you’re gonna be doing something a little more physical, or want to add a pop of color to your outfit, they come in a lot of fun colors!” She then handed the tights to Tyler so he could feel those as well.
While all the information Sarah was presenting to him was helpful he didn’t exactly know how to respond, so when Sarah looked to him for a response of some kind, he had to stop and think. He looked at the pair of tights and pantyhose in his hand and then looked back to Sarah, hoping for some spark of inspiration of what to say. He once again found it from her legs, “So which are those?” Tyler asked, gesturing to her legs, “Pantyhose or tights?”
“Oh these? Pantyhose.” She said placing a hand on her legs. “Since I usually have to wear business formal for work I usually have to wear some type of pantyhose if my legs are exposed”
“Oh that’s kinda annoying” Tyler responded
“Oh it really doesn’t bother me” she responded while waving a hand, I kinda like wearing them, they make my legs look good, doncha think?”
Tyler was taken aback by the question, he responded by squeaking out a “yeah I guess”.
“Women used to wear them with pretty much every outfit, but like I said they’ve kinda fallen out of style. Which is a real shame if you ask me, they’re a great accessory! You can give them a try if you want.” She said pointing towards the pairs Tyler was holding.
Tyler looked down and let out an “Ugh”.
Sarah quickly responded to his confusion by saying “Oh duh, they’re not exactly easy to put on, let me show you. Be right back.”.
Sarah then walked into her bathroom and closed the door. When she returned she was holding the pair of pantyhose she was wearing earlier. Sarah then sat down on the bed next to Tyler and started explaining how to put them on.
“Ok so you’ll start by rolling up one of the legs in your hand, and then slip your foot into it. You’ll want them a little loose at the toes, and then tight on the rest of the legs. Then once you’ve got one leg most of the way up, you’ll do the other legs the same way.”
As Sarah did all of this on her own legs Tyler was mesmerized, she wasn’t wrong they made her legs look great. As she reached her upper thigh she had to hike her skirt a little revealing more of her thighs. Tyler tried to avert his gaze but found his eyes moving back to catch a glimpse of Sarah’s wonderful legs.
At last when she was finished she said “See not so bad! They can be finicky sometimes but you’ll get the hang of it! Go ahead, give it a try!”
Tyler sat motionless briefly and then looked at Sarah who was smiling and eagerly awaiting for him to begin. Tyler did like she demonstrated and began rolling up one of the legs. He then pulled up the first leg and proceeded to roll up the second leg, slip in his foot and pull it up. The sensation of the Pantyhose against his legs was certainly interesting, the soft nylon almost felt nice clad against his legs. Then came to the part where he'd have to hike up his dress to pull them up and over his waist. He turned to try and keep Sarah from seeing too much of his undercarriage, and pulled them up the rest of the way.
"What do you think?! Sarah asked.
"They ugh, don't feel too bad." Tyler responded.“That's great!” Sarah cheered. “Those are going to make your legs look way better in a dress!" she followed up.
Tyler leaned down to touch his legs and said “wow they feel so smooth”.
“They feel pretty good, don’t they?” Sarah asked.
"Yeah I guess so” Tyler responded. Internally he had to admit he didn’t hate the way they felt.
“Well feel free to enjoy them the rest of the night” Sarah said with a big smile.
“Ugh, thanks” Tyler said cracking a small confused grin.
The rest of the night proceeded like all the others, dinner, small talk, television, but throughout the whole night Sarah seemed so joyful. Tyler could tell that she really seemed to be enjoying her time with him and the whole clothing journey the two of them were on together. Sarah’s joy was infectious because Tyler found himself having a fun night also.
At last when there night came to an end they sleepily turned the TV off and headed upstairs. Without instruction Tyler found himself walking into Sarah’s and headed towards her back closet to pick out a new nightgown. While he flipped through the various items of sleepwear he heard Sarah enter the closet behind him.
“You’ve keep picking one of my Miss Elaine’s or Shadowline nightgowns, gonna be adventurous tonight and try something new?” Sarah asked
“Oh ugh, I guess I can try” Tyler said.
Tyler flipped through the rack and picked up a simple red sleeveless nightgown with black lace trim around the chest. He held it up to get Sarah’s approval and she smiled. She then ran off to her dresser and began rifling through her panty drawer. When she returned she was holding a matching pair of red and black lace panties.
“Here, these will feel great under that nightie!” She said walking up to Tyler and handing the satin panties to him. She then kissed him on the cheek and bid him farewell for the night.
Tyler walked out of Sarah’s room and heard the door close behind him. Once again he felt butterflies and was overcome with confused feelings. He walked into his room and took his dress off. Then while standing there in his underwear he caught a glimpse of himself standing there. He cracked a smile seeing himself in his bra, panties, and pantyhose; he thought he looked kinda good. Maybe sexy even. But after a moment he cast those thoughts aside and stripped naked so he could shower. When he returned he started by slipping on the panties Sarah had given him. She was quite right, they were very nice feeling to wear. He then slipped the nighty over his head, and while it was more feminine than all of the nightgowns he had been wearing, it’s not like it felt all that different to wear.
Clothes are just clothes he told himself; but once again as he walked towards the bed he caught a glimpse of himself in the mirror. This time he lingered a bit longer, and thought more about his situation. He loved the attention he’d been getting from Sarah while he’d been wearing all these clothes. Neither of his parents ever paid any attention to him, nor did they get excited to spend time with him, like Sarah had been. Additionally, Tyler had never received so much flirtatious attention from a girl before, even if it was a member of his family. Unconsciously he began running his hands down the sides of his satin nighty and thought to himself that he really didn’t hate this whole feminine situation, maybe he was even beginning to have fun.