Disclaimer: I don't own Jessie and I also didn't come up with the idea for this pairing. This story was requested by 27. Enjoy!

Jessie Prescott stood in Zuri's bedroom, staring at the blue portable toilet as she considered what Darla would say if she told the bitch that she slept inside a port-a-potty the night before. She shook her head as she realized how her life now involved sleeping on toilets. This wasn't the life that she wanted for herself. Before Jessie arrived in New York, she had dreamed of starring in Broadway plays, filming television shows, or singing on stages. The eighteen- year old Texan never imagined herself being the nanny of four adorable kids or being hired as a nanny by a movie director and a fashion designer. She definitely didn't assume that sleeping in port-a-potties was part of the many roles she had to perform as a nanny.

"It feels like a potty every day," she joked to herself.

She was glad that none of the kids were around to hear her joke. The girls were spending the morning at the apartment complex's spa and the boys were in their room doing who knows what. For the first time in the last few months, Jessie was finally alone. This was the first time that she was actually grateful to be alone. As long as she could remember, she was always by herself - alone in her bedroom, a hermit in school, or in solitary at the military base. Her father was either too preoccupied with training or too busy serving overseas to spend any time with her. When it came to friends, her father's occupation prevented her from having any. The only person she had growing up was Darla but Jessie could never consider the deadpan bitch a friend.

Once Jessie started high school, the only remedy for her loneliness was boys and she quickly built a reputation with them. The jocks labeled her as a single serving of a southern belle. The bad ass drama kids affectionately referred to her as "flying over brazil for the night." The techies introduced her as Fort Hood's overnight wife. Sometimes when she saw a lover in the hall, he would point to her and whisper to his buddy that "he took a ride on the town pony." The boys' nicknames didn't bother Jessie as much as the ones the girls called her. The environmentalist girls called her a "cum depository," the cheerleaders labeled her as a "skeet guzzler," and the ultra conservatives just stuck with the term "slut." Despite the small variance in jargon, everyone agreed that Jessie was a whore.

Her promiscuity had nothing to do with manipulation, popularity, or vanity. She hated waking up in the middle night, turning over and seeing that the other side of the bed was empty. She liked laying her head against someone's chest, cuddling up against them as they stroked her hair. She knew that the guy would leave her the first thing in the morning, ignoring her when she walked by him in the halls and forgetting their relations when he flirted with someone else right in front of her. She cried herself asleep on the nights when she texted an old flame and he wouldn't reply. She would leave messages on his phones, singing Taylor Swift songs while she played a few strings on her guitar. The only thing that made her feel better was when she walked around the base a midnight, spotting one of the solider's son. Before she knew it, his hands would be unbuckling his pants and yanking off her cotton undies. It was a vicious cycle that was broken the day a cute little six-year-old girl found her lying on the sidewalk.

Gutter whore, she thought as she imagined what Darla would say if she found out exactly how she found her job.

To Jessie, it was irrelevant if Zuri approached her and offered her the job. What mattered was the fact that she was no longer alone. In fact, she could never be alone. The past few nights, Zuri had kept crawling into her bed and waking the older girl up when the younger girl tossed and turned. Jessie usually would pleasure herself before she went to sleep but now Zuri made that impossible.

Now since the kids weren't buzzing around her, Jessie could finally take care of her needs. She stared at the port-a-potty and wondered how long it would be before Tony's buddies came to move it. She had just overcome her fear of being in portable toilets and the only way Jessie could think of to celebrate was to "paddle her pink canoe" inside the tiny bathroom.

She touched the waistband of her black high-waisted skirt, making sure that her cellphone was still properly stuck between her navy blue blouse and the elastic band of her skirt. Out of habit, she glided her fingers up to her chest and over the swell of her breast. She could feel the small package wedged between her black bra and her C cup sized breast. She knew that it was stupid to always keep a condom inside her bra since she no longer had the time for the type of frivolous sex she had during high school. Still, she always liked to feel prepared for anything. She opened the plastic blue door, stepping inside as her black heels made a clink. She closed the door so fast that her skirt got caught in the door's cracks. When she re-opened the door, she noticed that there was an unfamiliar teenager standing outside.

"Who the heck are you?" she sputtered.

She stared at the boy, his brown eyes were leveled with hers. He flashed a smug smile, showing off his perfectly pearly white set of teeth. Jessie assumed that his teeth were too perfect to be natural so he must have had braces when he was younger.

Rich kid, Jessie thought as she scoffed out loud. He must be one of Emma's little boyfriends.

She had to admit the kid was handsome. He had slicked black hair, brown eyes, and tan skin. He looked like he spent a lot of time in the sun. Automatically, that made Jessie feel that the boy wasn't the stereotypical arrogant, rich boy that lived in Manhattan. He looked down to earth, active, and probably spent a lot of time playing sports. In fact, he looked like a boy that Jessie could of went to school with. She noticed that he was wearing a plain gray t-shirt and blue jeans. He definitely wasn't one of Emma's friends and Jessie imagined that Emma probably thought the boy was beneath her.

"My dad wanted me to tell ya that he's running late," he said as he eyed Jessie up and down. He sounded like he was from New Jersey, only confirming to Jessie that he wasn't one of Emma's friends. He was definitely like one of the boys from Jessie's high school. Most boys tried to wait until the girl wasn't looking to check her out. This boy had a lot of nerve since he made it completely obvious that he was examining her features.

"Hey, eyes up here!" she yelled as she pointed to her face. He ignored her comment and shrugged while he put his hands into his pockets.

"My dad's gonna move that," he said as he pointed the port-a-potty. "He's too busy shitting in the john." He paused when he noticed Jessie roll her eyes at him for cursing. " So he sent me here to warn ya but it looks you wanted some good ol' alone time in the crapper."

"I was just ..." Jessie started to say until she noticed he was staring at something down below.

"Too late," he said with a smile as he looked up.

Jessie gasped when she looked down immediately pulling her skirt down. When she had closed the door on her skirt, it made her skirt rise up. Now she knew the boy was ogling at her white cotton panties and she understood what he meant by "too late." Jessie had been so horny for the last few days and she had zero time to "polish her pearl." There was a huge wet spot on her underwear and she hoped that the boy assumed that it wasn't sex juices.

"Shoo, ska doodle," she said as she pointed off in a random direction. "Thanks for telling me about your dad and you can go while I wait."

He pretended not to hear her as he checked her out again. Jessie glared at him but that didn't make him stop. He quickly did an obscure hand signal with his hands which made Jessie look down and noticed a bulge growing in his pants.

Gee buddy, I know I'm attractive but keep it contained in your pants, she thought but by the boy's smirk, she realized she said it out loud. He took a step closer which signaled Jessie's reflexes, and the next thing she knew, the boy was lying on Zuri' bedroom floor.

"Holy Shit!" he exclaimed as he used his arm to prop himself up. "Some arm there."

"You're looking at a military daughter," she said as she folded her arms against her chest.

"I didn't mean any harm," he said as he stood up and took a few steps back. "It's just I never saw a pretty girlie like you."

"That's what all pervs say."

"I'm serious - I really mean - I go to a Catholic all boys school," he studdered. "I never gotta chance to be around girls."

Jessie shook her head and said, "I don't believe you. I'm sure you made a sex bet with your fellow boy scouts on who could screw the most Manhattan nannies. I have half a mind to tell your dad what you did."

She noticed the boy soften, his shoulder slumped as he finally looked up at her eyes. "Don't do that," he pleaded. Jessie wasn't sure if he was being serious.

"All you're going to do is break girls hearts," Jessie said. "And stay away from my girls. I got kids to protect here. I bet you already chucked a bunch of girls and left them stranded on heartache island."

"Look, the only girl I ever been with was a daughter of a baptist pastor that I met at bible camp last summer," he began. "We banged and then she cried afterward."

"How did you screw that up?" Jessie asked as she raised her eyebrows.

"I shouldn't have boned such a prude," he answered in a matter-of-fact type of way. "All I wanted was to see why everyone I know is so anti-sex. I know why now. Sex fucking sucks."

Jessie sighed as she looked at the young man standing in front of her. He was blunt, disrespectful, and ill-mannered. Now she knew that he had spent his life repressing sexual desires and she could imagine that the people around him didn't exactly correct some of his less charming features. Jessie knew what it was like to grow up in a place that expected you to behave a certain way but failed to show you how to do so. She wasn't blaming this on the military or religion. She was blaming it on the people who cared more about using rules to punish instead of setting guidelines to help others. Of course, there was always room to take responsibility. She knew that she didn't always listen to others and she knew that the boy in front of her didn't as well. Jessie grew up thinking that no one understood her yet she realized that she never tried to understand anyone. Maybe the boy had the same problem.

Jessie thought about how the Rosses made her compassionate and self-less. They filled her life with meaning and made her accountable to someone. As she looked at the boy in front of her, she realized that he probably didn't have anything that made him accountable. He was drifting through life like she was. Using sex as a substitute for love - the love that you receive from family and friends. If only she could tell this boy what she knew. If only she could be a mentor to him and answer the questions that no one else would answer. The first thing she wanted to correct was his assumption about sex.

"Sex is awful with the wrong person," Jessie corrected.

"I know where ya going with this," he signed. "When I finally meet the woman I'm meant to spend eternity with-"

"Gosh no," she interrupted. "The right person is someone who respects you and makes you feel safe. Someone who knows what they're doing and someone who is not afraid to be told "no." The boy looked surprised and Jessie was glad that he was finally speechless. "You understand how consent works?"

"Consent?" he asked as he scratched his head. "Isn't that like giving permission?"

"Exactly," she answered. "Sex is only good when two people consent. If one person changes their mind and decides they don't want to do it, it's not consent. It's rape. If someone is pressured to have sex, that's called coercing. As long as both people willingly agree, then they are good to go."

Jessie studied the boy as she taught him one of the most important lessons about sexual intercourse. She didn't expect him to be a Tony and wait forever to tap someone's ass. She just wanted him to treat a girl with more respect. She hoped that the next time that he sees a girl he likes, he won't keep staring at her boobs. Jessie looked at him again and noticed that he must have been considering the things she said.

"And when you like a girl," she began. "Try not to make is so obvious that you're checking out her ass."

"How else would I know if she has a hot bod ?" he shot back.

"You wait! Listen kid, you're never going to hit a home run if you're staring her down the minute you meet her. Get to know her name first, shake their hand and during the conservation casually glanced down at their boobs. Make it quick like it was an accident. When she gets up and turns around, feel free to look at her nether region. Okay?"

"Got it."

"And always keep things slow - slower than slow. You never want a girl to think you're just using her to get laid. Be smooth and try to get her to make the first move. Always stare at someone directly in the eyes. It not only shows confidence but it makes it seem like you're not gawking at her."

The boy began looking irritated and he pulled out his android to check the time. He must have noticed Jessie glaring because he shot her an apologetic smile. He took a step closer to her, slowly as if he had been waiting for Jessie to punch him. When she didn't, Jessie noticed that his shoulders relaxed and he looked into her eyes again. She nodded in approval and smiled at her new student. She couldn't believe that she was teaching this strange un-named boy about "sex smarts." Someone had to teach him and it just turned out that Jessie had a gift for working with kids.

"That's great and all," he muttered before shouting, "How is that going to help me know what to do?" He must have noticed the confused look on Jessie's face before he added,"It's not like you're going to show me how to put my P in someone's V. Thanks for ya tips but I'm never gonna get any ass."

"I'll teach you."

"Huh?"

"How old are you?"

"Fourteen. Why does this matter?"

"I'm eighteen," Jessie said and she began to remember what Emma told her about New York's statuary rape laws when Emma tried to date an older boy. "In New York, a minor can have sex as long as the other person isn't more than four years older than them."

The boy stared at Jessie for a second before looking around the room. She watched as a cocky smile appeared on his face while his bulge grew more visible. He checked his cell phone before taking a step back from Jessie. She assumed that he was trying to figure out if she was serious. Jessie was completely serious about having sex with a fourteen-year-old boy just to teach him about having sex with a girl his age. She knew that a part of this was wrong but New York's law sort of permitted this. It's wasn't like she was coercing him or forcing him to do something that he didn't want to do. It was obvious that he was attracted to her and she was so horny that she was desperate for someone to "stick it to her."

"Would you like me to show you how to have sex?" she asked in a hushed voice.

"Yeah."

"Yeah, what?"

"Yes, I wanna have sex with you."

"Now remember, you can change your mind at any time."