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Description

...Okay, so I feel like I should probably explain this? Yeah.

This is a part of a Tyler headcanon I have, and because of Lindsay's role I couldn't imagine picking a better day to post stuff for it than on Lyler Day.
(warnings for some mild? transphobia/homophobia)
~ ~ ~ ~ ~ ~ ~ ~

Somewhere along the line (and after talking with other people), I've developed the headcanon that Tyler likes women's clothing/jewelry. Not as a sexual thing or as a gender identity crisis. He just...likes them. Thinks they're really pretty.

When he was a kid, he used to watch his mom pick out her outfits for nights out with his dad or big parties. She let him pick out what jewelry she would wear for the night, and he'd watch her put on her makeup and see how different she'd act with a nice dress on and all the shiny, pretty bracelets and necklaces and stuff.

Every once in awhile, he'd sneak into his parents room and try on some of her jewelry, or maybe try to clonk around in a pair of heels, pretending to be as cool and pretty as his mom ...until he got caught wearing one of her long skirts like a dress.

His parents weren't happy. The basically drilled into his head that he was a boy, and because he was a boy he had to do boy things. Good, normal boys liked girls who wore nice dresses; they didn't want to wear them. And of course, Tyler was a boy wasn't he? He wasn't a girl who wanted to wear makeup and dresses, wasn't he?

Of course not.

After that, Tyler wasn't allowed to help his mom pick out jewelry. The box went into the closet, which now had a lock on it. He was pushed into sports, and he did love to play! The fact that it was tough sports that girls supposedly didn't play only made it better, because heck yeah Tyler was a boy, and he'd prove it!

And that's pretty much how it went up until Total Drama. Tyler showed his stuff on the show and proved his manliness; he even got an amazing, smoking-hot girlfriend! Sure Lindsay wasn't the smartest girl, but she was definitely the sweetest.

She also had the biggest walk-in closet, and the most amazing clothing Tyler had ever seen. Dozens of shoes, an entire dresser of jewelry...But Tyler was a guy, and they didn't care about that stuff unless it was on a girl. So he only peeked at her stuff when Lindsay was deciding what to wear for a date, helping her to decide. If he happened to keep looking at stuff while she changed it was no big deal; he was keeping busy to distract himself...

It was on one of these occasions that Tyler came across a new outfit in her wardrobe; it was gorgeous, soft silks with a wrap around shirt and a flowy swishy skirt...that was way too big for Lindsay to wear. That's when Lindsay gushes that the top was totally Tyler's color, and that the cut would be great for his broad chest, and he stops breathing for a few seconds.

He never could say no to Lindsay; he sure as hell tried though, going through everything his parents used to say, about how boys should never wear girl's clothes and any man who did was either gay or a pervert. Lindsay was unusually quiet throughout his rant, which got more panicked as he realized he kept looking at the outfit she was holding...

And then Lindsay suddenly asked if he thought she was a boy when she wore pants, and it stunned him silent. She kept going, thinking it was stupid how it was totally fine for girls to wear nice jeans and cool suits and stuff, but boys can't even look at a pretty dress on a hanger, never mind try it on. Wearing pretty clothes can make people so happy, and telling someone they can't wear it...it just seemed so mean!

That when it clicked for Tyler that the outfit was too big for her, but it would be the perfect fit for him.

Lindsay had looked for and bought an outfit especially for him, because he couldn't try on any of the stuff he looked at in her closet all the time, and she thought it made him sad. She wanted him to be happy.

He never could say no to Lindsay. Which is why he finally took the skirt and top from her and went to change, even when it felt like his stomach and heart were spinning around in a teacup ride as he did it, and thought his face was matching the burgundy color of the top when he finally pulled himself out of Lindsay's bathroom as she made a barely-stopped squealy noise and helped him put on her braided bracelet and necklace he'd looked at at least a dozen times before.

And then she dragged him over to her full-body mirror to look at himself.

He looked pretty. He felt pretty.

He also felt wrong because he felt pretty, but Lindsay was right there holding his hand and smiling at him like...well, like how he probably looked at her whenever she did something amazing.

God, he loved her.

Description

...Okay, so I feel like I should probably explain this? Yeah.

This is a part of a Tyler headcanon I have, and because of Lindsay's role I couldn't imagine picking a better day to post stuff for it than on Lyler Day.
(warnings for some mild? transphobia/homophobia)
~ ~ ~ ~ ~ ~ ~ ~

Somewhere along the line (and after talking with other people), I've developed the headcanon that Tyler likes women's clothing/jewelry. Not as a sexual thing or as a gender identity crisis. He just...likes them. Thinks they're really pretty.

When he was a kid, he used to watch his mom pick out her outfits for nights out with his dad or big parties. She let him pick out what jewelry she would wear for the night, and he'd watch her put on her makeup and see how different she'd act with a nice dress on and all the shiny, pretty bracelets and necklaces and stuff.

Every once in awhile, he'd sneak into his parents room and try on some of her jewelry, or maybe try to clonk around in a pair of heels, pretending to be as cool and pretty as his mom ...until he got caught wearing one of her long skirts like a dress.

His parents weren't happy. The basically drilled into his head that he was a boy, and because he was a boy he had to do boy things. Good, normal boys liked girls who wore nice dresses; they didn't want to wear them. And of course, Tyler was a boy wasn't he? He wasn't a girl who wanted to wear makeup and dresses, wasn't he?

Of course not.

After that, Tyler wasn't allowed to help his mom pick out jewelry. The box went into the closet, which now had a lock on it. He was pushed into sports, and he did love to play! The fact that it was tough sports that girls supposedly didn't play only made it better, because heck yeah Tyler was a boy, and he'd prove it!

And that's pretty much how it went up until Total Drama. Tyler showed his stuff on the show and proved his manliness; he even got an amazing, smoking-hot girlfriend! Sure Lindsay wasn't the smartest girl, but she was definitely the sweetest.

She also had the biggest walk-in closet, and the most amazing clothing Tyler had ever seen. Dozens of shoes, an entire dresser of jewelry...But Tyler was a guy, and they didn't care about that stuff unless it was on a girl. So he only peeked at her stuff when Lindsay was deciding what to wear for a date, helping her to decide. If he happened to keep looking at stuff while she changed it was no big deal; he was keeping busy to distract himself...

It was on one of these occasions that Tyler came across a new outfit in her wardrobe; it was gorgeous, soft silks with a wrap around shirt and a flowy swishy skirt...that was way too big for Lindsay to wear. That's when Lindsay gushes that the top was totally Tyler's color, and that the cut would be great for his broad chest, and he stops breathing for a few seconds.

He never could say no to Lindsay; he sure as hell tried though, going through everything his parents used to say, about how boys should never wear girl's clothes and any man who did was either gay or a pervert. Lindsay was unusually quiet throughout his rant, which got more panicked as he realized he kept looking at the outfit she was holding...

And then Lindsay suddenly asked if he thought she was a boy when she wore pants, and it stunned him silent. She kept going, thinking it was stupid how it was totally fine for girls to wear nice jeans and cool suits and stuff, but boys can't even look at a pretty dress on a hanger, never mind try it on. Wearing pretty clothes can make people so happy, and telling someone they can't wear it...it just seemed so mean!

That when it clicked for Tyler that the outfit was too big for her, but it would be the perfect fit for him.

Lindsay had looked for and bought an outfit especially for him, because he couldn't try on any of the stuff he looked at in her closet all the time, and she thought it made him sad. She wanted him to be happy.

He never could say no to Lindsay. Which is why he finally took the skirt and top from her and went to change, even when it felt like his stomach and heart were spinning around in a teacup ride as he did it, and thought his face was matching the burgundy color of the top when he finally pulled himself out of Lindsay's bathroom as she made a barely-stopped squealy noise and helped him put on her braided bracelet and necklace he'd looked at at least a dozen times before.

And then she dragged him over to her full-body mirror to look at himself.

He looked pretty. He felt pretty.

He also felt wrong because he felt pretty, but Lindsay was right there holding his hand and smiling at him like...well, like how he probably looked at her whenever she did something amazing.

God, he loved her.