A Surprising Gift
And so, that weekend and the next week was filled with more of the same. Tyler would wake up, piece together an outfit from Sarah’s closet, and spend his day eagerly awaiting his Aunt’s return. Then together the two of them would have girl talk time, where she’d educate Tyler on some new piece of women’s fashion. As time went on Tyler was becoming an expert on women’s wear, and Sarah was more than happy to play the role of womanly mentor.
It was not lost on Sarah that to the outward observer, the whole situation was quite strange. If dressing him up in her clothes wasn't bad enough, he was also wearing her underwear. But Sarah could not deny the joy both had found sharing in their exploration of femininity. Having spent her life with such a large focus on work she had become quite lonely, and never had the opportunity to raise the daughter she always dreamed of. So to be able to pour her efforts into raising Tyler was scratching her maternal itch.
While she knew what she was getting out of their little arrangement, Sarah was not quite sure what Tyler was after. She had her suspicions of course, his parents had been too busy fighting for the past few years to pay him any attention, and here comes bubbly Aunt Sarah to lavish him with attention. She was sure it must be nice to finally be the center of attention from a parental figure after so long of neglect. In addition to that, he was a hormonal teenage boy who was being exposed to a beautiful woman. Sarah wasn’t blind, she saw the way he looked at her sometimes, the way he blushed. She wasn’t going to scold him for being attracted to her, so long as he continued to be respectful.
While either of those reasons may have been enough to convince Sarah as to why Tyler had become compliant with wearing Sarah’s clothes, she had a nagging thought in the back of her mind. What if he was transgender? What if he’d struggled with his gender identity his whole life and Sarah had finally given him an outlet? To better understand her suspicions she did a little research on transgender youths, to see if Tyler fit any of the signs. It was hard for her to tell based on her research. But while she was searching the web she did find some great websites about how to wear women’s clothing as a man.
One thing she found particularly interesting were breast forms. She thought perhaps this might give her an opportunity to kill two birds with one stone. Sarah had wanted to get Tyler a gift for being such a good sport with the whole situation, and get to the bottom of his gender identity. Perhaps breast forms could accomplish both, she thought. So after a quick order on amazon, she had her conversation gift on its way.
She had them shipped to her work so that Tyler would not discover them. She took a peek at them inside the box once they arrived and Sarah could not help but giggle. They looked pretty real; felt pretty real too as it turned out. While they certainly made her smile, she wasn’t sure what Tyler would think when he got them. She spent the rest of her day eagerly awaiting her return home.
When her moment finally came she walked through the door and found Tyler wearing a green dress and getting things ready in the kitchen. She kept her cool, and proceeded through the night as normal. After eating dinner with Tyler she told him to stay seated because she had a gift for him. She excitedly pranced over to her bag and pulled out the box, and handed it to Tyler.
“What’s this?” He confusingly asked.
“Look Tyler, I’ve been having a lot of fun doing this whole girl thing with you so I thought I’d get you something as a little thank you.” Sarah said with a smile
“Thanks, but you didn’t have to do that” Tyler said while blushing.
“Don’t thank me yet, it’s a…..unique gift.” Sarah responded pensively.
Tyler ripped open his gift, only to be met with the sight of two realistic nipples pointing up in his direction. After a single chuckle, he said “oh wow…… um are these like fake boobs?”
“Yeah these are breastforms, they fit inside of bra cups to give you the feeling of natural breasts” Sarah nervously explained
Given that he seemed to have never seen breastforms before, some of Sarah’s questions were being answered for her. If he didn't recognize breastforms he hasn't done much research on crossdressing or transgenderism. This also meant that Tyler’s crossdressing journey thus far had largely been to appease Sarah. Somehow this was worse than Tyler having suffered with gender nonconformity all his life, now was she forcing it onto him? Tyler’s next response eased her worries a little.
“Wow, they’re heavy, these are kinda cool” Tyler said while picking up a form.
“I ordered C-cups, big, but not huge, figured I’d give you the full experience” Sarah said nervously.
“I didn’t even know they made something like this. Thanks Sarah!” Tyler said with an inquisitive smile, still intently looking at the form he was holding.
“You’re welcome sweety” Sarah let out with a relieved breath. She then followed up with “We’ll don’t just sit there staring at them, go try them on! You can grab one of my t-shirt bras without any padding”.
Tyler agreed and headed up stairs towards Sarah's room. Although going into Sarah’s bedroom to grab some clothes to wear was old news, the fact that he had something new to try had him a little giddy. Sarah had shown him all the different bra types and knew exactly what he was looking for. He took out a plain black t-shirt bra, took his dress and push-up bra off, and then slipped his new t-shirt bra on. Then came the big moment, he put his new breastforms in, one cup at a time, and wow they were heavy! He then couldn’t resist, he reached up and gave them a squeeze; much more natural feeling than a push-up bra! Feeling pretty satisfied with his new experience he walked over to the bed to get his dress back on, and his breasts jiggled as he walked! It was crazy how unique the experience was for him! Once he put his dress back on he couldn’t help but notice how much larger (and more natural his breasts looked in the dress). He cracked a little smile and groped himself again.
Then as he stood there, false breasts in hand, body clad in layers of feminine garments, Tyler’s smile faded. His joy was replaced by unease. Why was he feeling these feelings, what was happening to him? Here he was standing in his aunt’s bedroom, wearing her clothes, AND false breasts, and he was smiling? Tyler's thoughts began to race, everything in him was telling him that this was wrong. Yet for some reason he cracked that smile, he had been having fun the past week. Why?
When he got back downstairs he was met with a question by Sarah, “so what do you think, they certainly look good!”
“It’s ugh, crazy how different they feel than just the push up!” Tyler said staring down at his chest.
“Well that’s good, do you like wearing them?” Sarah asked.
“I…. I think so. They’re kinda their own experience.” Tyler said, rationalizing to himself.
“Well, I’m glad you like them” Sarah said proudly.
Sarah’s fears of an inappropriate gift having been lifted she continued on with her night. Despite this she kept getting glimpses of Tyler where he seemed off. He seemed almost unnerved at times. Deep within the depths of his own mind. Maybe she was wrong, maybe she crossed a line after all. Her anxiety at the situation was becoming too high, she had to investigate.
Finally Sarah asked again “ So you’re sure you like them, the falsies I mean, you just seem a little quiet”.
“Yeah!” Tyler responded looking down at his chest with a smile. “I really like them. It’s just” and then he paused, and as if it was with great difficulty finally said “I’ve been thinking……I think…………. I think I like being a girl”.
They both sat in silence for a moment after Tyler’s declaration. Sarah understood now why Tyler seemed unnerved; he was almost certainly feeling a lot of new things about himself. Sarah was worried the breast forms might stir up preexisting feelings, she didn’t foresee the forms creating new ones within Tyler. She knew he was probably in a vulnerable mental state and chose her next words as carefully as she could.
“Oh well..... that’s good” She said at last, with a reassuring smile. “You’re welcome to be a girl as much as you want while you’re here with me”
“Thanks Sarah” Tyler said, cracking a smile.
“You know, there’s more to being a woman than just wearing our clothes, if you like I could always teach you some more things, about being a girl, if you want”.
“I think I’d like that……. I guess it’s like you said, you always wanted a daughter.” Tyler said bashfully.
Sarah became overcome with emotion. She went to Tyler and embraced him. After holding him she gave him a kiss on the cheek and then grabbed him to get a better look at her new “Daughter”.
“You know Tyler isn’t exactly the most feminine name” Sarah said with a sly smile. “What about…… Taylor? That’s a little more befitting of a girl?
“Oh ok” Tyler said with a little grin. “I can be Taylor”.
Sarah giggled and said “You’ve got a lot to learn about being a girl Taylor, but don’t worry, mumsy’s a good teacher”
Taylor also let out a little giggle and said “Thanks, uh….. mommy.”
Chapter 5<--------> To be continued