Hey guys! If you've read Be Careful What You Wish For, you're gonna want to read this too. And if you haven't that's fine, but you can if you wish and I encourage you to :) This started out as a silly thing to help me vent about some of my own confusions, but then it turned into a potential Leo love interest! I wasn't sure who I wanted to be Leo's girl, but then this came to mind and became the perfect fit! I especially like it cause Leo's my favorite and she's the most like me, hehe.

I'm sorry if you think this is just a whole lot of complaining, I don't think it's like that it's more just trying to understand the character, ya know? and I feel like a lot of people go through this crap in the high school years.

I'm excited to bring Cassidy into BCWYWF in the near future, and for those of you who have read it, this little one-shot doesn't mean that I'm ditching that story! This is just the first weekend I've had in forever to actually sit and write. Sorry about that :/ Also, if you were expecting some Leo/Cass action right off the bat, I'm gonna have to disappoint you. We're not ready for that yet. But in the future? you'll see!

Whew, sorry for all the explaining! On with the story! and remember to review and tell me what you think!

Oh, and I don't own TMNT or NYC or any addresses in said city.


Cassidy was sick of feeling confused and conflicted all the time. Sure, teenage years weren't supposed to be easy, but the past year had proved that fact was an understatement.
Cass sighed and rubbed a shaking hand over her face. It was Friday afternoon, and as usual, she was at home lying on her bed. Fridays were her off days. No practice, and homework could be left for Sunday. She could catch up on TV, sleep, and eat whatever she wanted.
Sometimes she had to babysit, and sometimes the twins would come over, but not tonight.
For the 10,000th time, Cassidy asked herself a humiliating question.

You're a 16 year old girl; don't you have some social gathering you could go to? A party? Anything?
The even more humiliating answer was no.
Always no.

She had learnt to accept this, and even embrace it, not wanting to mingle with her peers anyway. Cassidy always felt like a mom around people her age, always the moral compass, never understanding how her fellow teens could be so materialistic, unsympathetic, and clueless.

Cassidy didn't belong in this generation.

What her peers didn't understand, and few had ever witnessed, was Cassidy's extreme fun side. Though she never did, Cassidy could party with the best of them. Not the drunk, high, illegal kind of partying, but the let loose, silly dancing, loud singing, be yourself kind of partying.

But not this year. Fear of awkward situations had caused her to pull back into her own shell, only showing small parts of her real self to the public.
So, another night of ice cream, cartoons, and superhero movies. Not so bad, right? Cassidy dropped her head into her pillow, moaning in anger and defeat. Thus was her life.

A vibration against her hip brought Cass back into reality. A text? Cassidy ran though the list of possible contacts in her mind.

Mrs. Tiller, Erin, Elana, Coach Mac...
In the small amount of texts she received, these where the people most likely to be the sender.

But when she lifted the screen to eye level, none of those names flashed before her. The one that did was extremely unexpected, and she could feel the butterflies fluttering in her stomach as she read the name. Her face grew warm and she immediately squashed the silly feeling inside of her.

New Message from Leonardo

With a shaking hand and a wandering mind, Cass opened the text.

Leonardo: Everything alright?

She held her breath. She knew Leo too well to know he had to be watching her to ask this. He was playing around, but in true Leonardo fashion, could probably tell that something was indeed wrong with her.

But why had he come in the first place? She hadn't seen him in months, as was customary during the school year. Very rarely did she see or hear from her strange friend other than the holidays and summer vacation.

Cassidy swung her legs over the side of the bed and reached to pull the curtains back from her window.
Expecting to see the blue masked boy- erhm, turtle- crouched on the rooftop of the enclosed porch outside her window; she was surprised and slightly depressed when nothing but deserted shingles met her eyes.

Thoroughly confused, Cassidy turned around and sat back onto her bed. Her thumbs flew across the keyboard of her phone.

Me: Where are you? How did you know?

Cass didn't have to wait long for his reply.

Leonardo: 100 Acre wood. And I just know- ninja?

Cassidy rolled her eyes. Of course, the fact that Leo is a ninja justified any questionable act. But she was happy to know he was hanging out in their old woods. But why? And why today? She typed back;

Me: Feeling nostalgic?

She figured she had the right to a smart-ass remark if he was going to play games.

His reply:

Leonardo: Something like that. Remember, 6 years ago?

That question had her stumped. 6 years ago? What in the world was he saying?

Me: Not exactly. You stopping by?

Leonardo: Of course.

Cassidy threw her phone beside her, into the duvet. From 100 Acre wood (yes, they had named the woods in Central Park after the forest in Winnie the Pooh) to her house was only a 15 minute walk, or in Leo's case, an 8 minute run. That gave her just enough time to contemplate what Leo meant by "6 years ago".

She opened her window to prepare for her friend's arrival. The breeze that moved into the room smelled perfect, like the start of summer. It was painfully familiar. Like the day she separated from Erin and Elana and wound up in the sewers on her own. When she had met the brothers. That was the summer she turned 10... Cassidy's eyes went wide. 6 years ago. She met the turtles 6 years ago.

Cassidy really couldn't believe it… It didn't seem like 6 years had passed. That day was still fresh in her mind.


"Lana, stop worrying! Think positive for once!"

"I am being positive! Erin, I'm just not sure about this area... Couldn't we have an adventure and still stick to 100 Acre wood?"

Erin and Cass shared a sidelong glance, communicating their exasperation over Elana's nervousness. They both knew when she let go; she could have just as much fun as they did. If only she was more carefree.

Cassidy, always the bridge between the conflicting twins, gave a loud whoop and pointed the front tire of her bike down West 82nd Street, where the outskirts of Central Park met the city. She had convinced her adventuresome best friends to accompany her on the "adventure of a lifetime". (Really just a bike ride to a large, made-to-look-pretty creek and sewer gate in the Park) But in Cassidy's 10 year old mind, it was the entrance to the Chamber of Secrets. (Harry Potter ruled their lives)

So the girls picked up their homemade wands, hopped on their Nimbus 2001's (bikes), and rode like the wind. Upon their arrival, the girls ditched their broomsticks on a hilltop and made their way down to the creek.

"Wands at the ready, girls." Cassidy whispered in an obviously practiced British accent back to her friends.

Each girl muttered, "Lumos", and imagined her wand tip glowing. Slowly, the three young witches crept closer and closer to the sewer grate, which stood towering above them at the end of the creek bed. Cassidy was the first to reach the jail cell door-like structure, and the first to see that the creek continued on the other side of the barred wall.

"This must be it! And look, I reckon we can shimmy right through those bars!"

"No, no, Cass. The Chamber can only open by a Parselmouth!"Elana said; she was finally getting into the game.

Cassidy smiled back at her friend. "Of course you're right Lana, good thing we've got a Parselmouth right here." She jabbed her thumb into her chest.

Lana and Erin pushed Cass forward, silently urging her to speak in the snake language. Cassidy produced a weak rendition of the hissing sound she had heard her hero say so many times before. Lana and Erin provided the sound effects of the bars magically moving away, and then slipped in between the un-moved bars.

Cassidy was so excited to find the "Chamber" that she shimmied through the bars and took off running through the shallow water. The twins were much faster than her, and she knew they could follow her splashing footsteps. She didn't hear the girls calling for her, or notice they were no longer next to or behind her. Her splashing and panting drowned out their voices.

Some minutes later, when Cassidy finally put the brakes on her run, she found she was utterly alone. And the tunnel was really really dark. In reality, her wand tip wasn't glowing.

"Okay, no big deal, just turn around and go back Cass…"

Cassidy had to speak aloud to herself, silence made her extremely uncomfortable. Thankfully, her eyes had adjusted a little to the darkness and she waded her way back in the direction she thought she had come from.

She hadn't been walking for more than a few minutes when she came across a split in the tunnel. Which one had she come from? And why hadn't she paid attention? Her feet where numb from the cold water and her hand had splinters in it from gripping her wooden wand so tightly. The urge to scream and cry worked its way up inside of her, but Cassidy swallowed the lump in her throat and pushed the hysteria down. She was going to find her way out of here. She was going to find her friends, and make sure they were okay. She had gotten them and herself into this mess.

And now she was going to get out of it.

Cassidy chose the left tunnel and pushed on. She would stop every so often to listen for any sounds of life ahead of her, and called out Elana's and Erin's names every so often. Then, if by some miracle, she saw a dim glow up ahead.

But when she ran closer to the light, all she saw was a small hole in the floor and a ladder. The light was coming from wherever the light led to… somewhere underneath her.

Should she go toward this light? Could it help her? Or would it get her even more lost, even deeper into the tunnels she was trying to escape?

Her body made the decision before her mind did, and Cassidy climbed down the ladder. The rungs were sick from moisture, and more than once Cassidy's feet and hands slipped out from under her. Finally, something more solid than a thin rung of a ladder hit Cass's foot. Breathing in relief, she lowered herself down to the floor.

But the floor wasn't a floor at all. She was crouched on a larger pipe, high above the ground she could just see below her. Dim lights were placed throughout the new tunnel, showing Cass that it went on forever in both directions. She cried out as her foot slipped a bit on the pipe.

Tears that had threated to fall now ran down Cassidy's face. Her body hurt from the physical strain of keeping herself on the ladder and pipe, she had lost feeling in her toes a while ago, and she had dropped her wand while climbing the ladder. She tried to shimmy down the pipe a little, but where would she go?

So Cassidy just hugged the pipe for dear life and let her tears overtake her. She screamed for her friends, for her mother, for anyone. In the back of her mind, though, she knew no one would find her. She was hopeless.

Cassidy lost track of time, and lost her voice. Her tears had long dried on her face and her hair was coming out of her ponytail, but she couldn't release her hold on the pipe to fix it.

Using the last of her energy and voice, Cassidy tried one more time to scream for anyone who could help her.

"Help! Anyone, please, please, help me! Please…"

Cassidy had just about passed out when something grabbed her around the waist and lifted her from the pipe. She didn't even have the energy to fight back, and could only hope whoever had her was going to help her. Her throat was too raw to speak, but she could hear voices just fine.

"What is it, Mikey?" Cassidy guessed this voice belonged to a young male, because his voice had cracked on the "is".

"It's a little girl… I think? Leo, you take her."

"Mikey, it was your idea to go chasing after random voices in the sewer! You carry it!"

"Nah Leo, this ain't an "it". Knucklehead's right, she's jus' a little girl."

Someone growled and the voice called Leo spoke again. "Fine, but you know we won't be allowed to take her back to the lair. Master Splinter wouldn't like it."

"Then what d' you suggest, O Fearless One?"

"…let me see her."

Cassidy felt her body shift from one pair of small arms to another. Startled, she opened her eyes. The guy holding her wasn't exactly visible in the light, but she could see he was bald and had something around his eyes. She worked up enough energy to speak to the boy.

"Can you… please take me home…? I just want to go home…"

His voice had softened. "Where's 'home'?"

Cassidy recited the address she had memorized years ago. "225 Central Park West."

"Guys, that's on the other side of the park. We can take her there." The boy holding her now spoke to the other voices she had heard.

That was when Cassidy had passed out.


The boys had told her years later how they had taken her home, and then got in trouble with their Father for being out so late. They had come back a week after that night, to check on her and show her who they really were.

She had been in trouble with Mrs. Tiller (Elana and Erin's mom), but her own mother hadn't even been home that week. She had taken one of her "trips" to "Uncle Benny's".

Everyday Cassidy thanked God for Mrs. Tiller, her real mom through the years. Her own mother was usually too busy selling her body and her drugs to lowlifes in Queens.

She also thanked God for her four terrapin friends, who saved her from the sewers. She grew closer with the turtles over the years, so much so that she was allowed to enter their home and meet their Father, who she admired immensely. The boys would come to her when they needed a friend, and vice versa. Her holidays were often lonely because the Tillers went to Canada to be with their extended family, and her mother always found some random guy to lie with.

The turtles found this out when Cassidy was 12, they 14. Ever since, she had spent the holidays in the sewers with the boys and Master Splinter.

She had been a bit jealous when April stumbled into their lives, but it wasn't like she saw the boys everyday anyway. She soon considered April a best friend and big sister; it was nice having another female around the lair when she visited.

Thoughts of April brought thoughts of Donatello. The two had become close this past year, and Cassidy hadn't seen as much of Donnie because of it. She didn't mind, but she missed him. She had been very close with each brother equally, and considered them all her best friends. But it was not secret that Donatello had been focusing on April this year.

Raphael, Mike, and Leonardo still texted her, but only Mikey and Leonardo had stopped by during Spring Break. She didn't think much of it; she knew Raph was a bit more secluded and guarded than the others. But she missed them all. She was really happy Leonardo was coming to see her, she realized; she had missed him the most although she had seen him most recently.

And she knew why. Ugh, she couldn't help herself for how she felt. Of course she noticed Leo's perfectly sculpted and strong body, his gorgeous eyes, and his rare, real smile. She also had loved to watch how he had grown; she wondered if he could get any taller.

Although she was undoubtedly attracted to her long-time turtle friend, she was so mixed up inside it didn't matter.

Ever since her break-up with her last boyfriend, Cassidy had been feeling… scared? No… awkward? Uncomfortable? Maybe all three. But any thought of physical intimacy made Cassidy more squeamish than a sissy girl around bugs.

The worst part was Cassidy couldn't figure out why she felt this way. At first, she thought maybe it was because of her past experiences.

Cassidy had "dated" her first boyfriend at age 12. He told her how he really loved her, and she loved the attention. She never told him that she had any feelings for him, because truthfully, she never did. She ended that relationship because she had a huge crush on his best friend.

The boy she had a crush on… well, they never dated. But he had asked her of pictures of herself, and she complied because of her silly infatuation. She never removed all of her clothes in these pictures, but they were apparently enough to make him want to. He sent her a picture of his… well his most private part. She received the text before she received the picture, and deleted the picture without looking at it. Cassidy lied back to him that she had seen it. It made her extremely uncomfortable and disappointed in herself that she would let things progress this far. She ended all ties with him, and vowed never to make mistakes like that ever again. She was worth more than that.

She dated another guy for about 5 days in 8th grade, when she had just turned 13. He was a loser, everyone told her, and so she dumped him. She never had any real feelings for him. She did have feelings for another guy, though, and he started paying attention to her only after the loser asked her out.

So she had a "thing" with this other guy now. She really liked him a lot, and was so happy when he paid her attention. She didn't care that he was a "manwhore". He wasn't like that with her!

After his practice one day, he asked her to meet him after school by a local pizza shop. She met him there, and he kissed her in the grass of Central Park. It was her first kiss; she still was wearing her braces, so she couldn't have been good at it. But a couple nights later, he asked her to sneak out and meet him again. She did, and they made out in the Park.

She was so happy, she didn't even care to worry if she was a good kisser or not. But within that next week, the guy had moved on to another girl. Cassidy was crushed.

Throughout the end of 8th grade, and the summer into freshman year, she was made fun of for the two guys she had had "things" with. She was embarrassed and sick with herself for letting this happen to her.

But only months into freshman year, most people forgot about her. And that "loser" she had dated for a couple days in 8th grade? He liked her again. Cassidy thought, what the heck, he's cute.

They dated for 7 months. They became more intimate than Cassidy had ever been. She had to stop him from completely disrobing her a couple times, and he got her bra off many a time. Cass pretended she liked it, but she really never got any pleasure out of his touches. She never felt anything deeper for him.

She was desperate to get away by month 6. An older guy had taken interest in her, and she clung to his attention. This made her boyfriend very confused and hurt, but Cassidy didn't care. She was sick of him.

Cassidy finally broke up with him.

…And not a week later, was asking for him back. The older guy was gross. She didn't really want anything to do with him either. She missed her old boyfriend. Wait, scratch that. She missed having someone close to her, someone to always talk to and say she was beautiful. She had pushed her other friends away in the process; Elana and Erin were very hurt. The turtle boys could tell something was wrong with Cassidy when she wouldn't accept their invites to the lair.

Her boyfriend took her back, and on the last day of school, they were dating again. Cassidy was leaving for a trip with Elana and Erin the next day, but they decided they'd see each other when she got back and they'd talk the entire time.

Leo also came to see her that night before she left. She couldn't help to notice how overly attentive and funny he was being. She loved it, loved having a night to catch up with her best friend.

On her trip she couldn't help but think about Leo.

When she got home, she met up with her boyfriend. They had one passion-filled night, which really wasn't that passion filled. It was like any other of their times. He just liked getting under her shirt.

They both left this time, on different trips. She went to a space camp (yeah, she wanted to be an astronaut, so what?) and told all her friends there about her perfect boyfriend.

When she texted him after they both got home, he wasn't the same. Cassidy knew something was wrong. The next day, he broke up with her. She was "poisoning" his mind and spirit, leading him away from God and to desire. Good riddance, Cassidy thought. He didn't deserve me any way. He was a sort of chubby, annoying goody-two-shoes, and I never got anything out of his kisses.

So that summer went on, and into sophomore year and Cassidy told herself to not date anyone. Leonardo became more attractive still, a fact she did not miss but tried to ignore.

Cassidy followed her own rule until she started crushing on an older guy, hard. He was beyond attractive. His personality wasn't perfect, but good enough. And his family loved her. The first night they hung out, he got under her shirt. She didn't want to scare him off, so she let him touch her even though she didn't want him to. She did stop him after a bit and told him "she wasn't going to have sex with him". He said he understood, but she didn't think he really did.

The problem was that she felt more with him than she had with her ex. She let things go on for a couple months, faking that she was "ticklish" whenever he tried to get into her pants.

He was probably fed up with not getting any, and not being able to hang out for about a month, so he broke up with her.

She didn't really want things to end, but she knew she had only liked their relationship when he wasn't pressuring her to have sex. And she would have done it, if she wasn't only 15 years old. She wasn't going to be one of those girls. Elana and Erin were there for her through it all, and encouraged her to keep her virginity. They became even closer than they had been in years.

April, who she had met that year, also praised her for staying pure. She told Cassidy he wasn't worth it. Cassidy knew this was true.

The boys didn't like to get involved with her relationship problems, other than Mikey. He would frequently come over those few months after for ice cream "dates", when they would just talk and listen to their favorite albums on repeat. Leonardo almost completely ignored the fact that she had dated someone at all. He just smiled a lot more openly once he knew she was single.

Cassidy put all of her efforts into her school work and her sports. Crew (the sport she had just recently fallen in love with) became her life. She forged close relationships with her teammates and coaches, and her natural talent shown. Cassidy was in the best shape of her life, and the best girl on the team. Her school work took up the rest of her time.

Summer ran into junior year, the most stressful year of Cassidy's life. Her and Leo talked all the time, and Donnie or April tutored her whenever they could. School and Crew were her everything.

Sure, guys flirted with her and some probably liked her. But she didn't care. She wasn't putting herself out there anymore. She didn't need someone to... be intimate with. She was young and had her life ahead of her to do things like that. Plus, Cassidy wasn't lonely, she liked keeping to herself. She got enough company from the twins and her teammates.

But she really did start to like Leonardo more and more.

And although she was so attracted to him in every way, there was no way of telling him or showing him. Cassidy didn't know if it was because he was different from the other guys she had dated (he was shy and a gentleman; he would never ever make a move on her. He wouldn't show her that he liked her more than a smile and lots of attention).

Or, if it was because she was beyond scared of being physical with someone. All of her past experiences had been so fake and hadn't made her feel anything. She didn't want to take a chance on Leonardo just for them being together to not meet the level of perfection she expected. It would ruin their friendship.

Why did he have to be so goddamn attractive, and nice, and funny, and trustworthy, and moralistic, and confident, and sweetly shy…

Cassidy stood and stretched her sore muscles, shook all thoughts of an attractive Leo out of her mind, and replaced them with Leo, her best friend, with whom she could talk to about anything.

When she turned to the window, wondering why he hadn't shown yet, Cassidy didn't expect to see Leonardo lounging in her desk chair, fake-examining one of his katana.

Before she could laugh at his joke, she steeled herself and crossed her arms. He wasn't gonna get to her that easily. Cass knew he must have come in while she was stretching, and had to have looked at her as he did so. What made her ask the question she did, she had no idea.

"Enjoyed the view, did you?"

A bit startled, Leonardo looked up from his katana sheepishly. "Uh, Cass, I didn't…"

His face and tone of voice pushed the laughter out of Cassidy. He was too cute. "Of course not! Leonardo, the Prodigal Son, he would never." She winked at his shocked expression.

Oh God, winking? NO nonononononono no.

But Leo wasn't so easily embarrassed. He collected himself and a semi-confident grin graced his green face.

"Got that right." His face turned serious again; his leader face. This could only mean trouble for Cassidy. "What's with the pity party?"

Shoot, Cassidy forgot that she had brought ice cream up with her. The empty carton, her laptop, and a Captain America DVD were strewn across her bed. If you knew Cass like Leo did, you could tell she was in depression mode.

"Oh, well you know. School is just stressful…"

Leo cut her off lightly. "The building or the people inside of it?"

Cassidy only had to look at him and he knew. He stood, and she fell into his arms sobbing. She hadn't cried like this since that day 10 years ago. Leonardo hadn't held her like this since they were very young. She was so happy to have him there, his support and his friendship to console her.

They stood that way for what seemed like hours, her face buried into his plastron and her arms constricted around his middle, small hands pressed up against his shell. His arm wrapped around her back and the other around her head, his large three-fingered hand slowly caressing the back of her head and combing through her hair.

"Don't let them get to you, Cass." He whispered and held her tighter still.


So, you like? Review! by the way, this happens like right before Raph and Mona first meet. just for you BCWYWF people :)