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Jessie: A Nanny Relationship (Ff,oral,rim)
by Disney Writer (disneywriter5@gmail.com)

Somewhere in the bustling City of New York lived the world famous Ross family. The Ross's were full of adopted children but none were as stunning or attractive as Emma. Emma is simply beautiful! She has long flowing blonde hair, clear alabaster white skin, crystal clear blue eyes, a dazzling smile and a cute petite body to match.

From the outside, it appeared Emma had the perfect life. She came from a wealthy family, received anything that she wanted, attends a top-notch private school and is already successful as teen model for a prestigious clothing line company. What problems could she possibly have?

However, once the cameras stopped flashing and she returned home; life just seemed really lonely to Emma. She would go literally months without seeing her parents and never really felt nurturing nature of her mother. She was given no advice and often times was supervised by a lazy overweight butler named Bertram.

She had her adopted siblings to keep her company and it would be enough for her at times, but most of them were either too young or immature to really have a serious conversation with her. She was a teenager after all and of course those problems escalate higher than they usually are.

For months she would hide behind that beautiful sassy smile assuring everyone that everything was alright. But the reality of the situation was she just could not handle being alone anymore. All of this changed abruptly when a new nanny came to town named Jessie.

The last few nannies used to hate Emma especially because of how pretty she was, but this one would prove to be different. Emma first encountered Jessie when she arrived from school. She walked up out of the elevator, still glancing down at her phone while texting. (Emma was notoriously glued to her phone, probably was one of the only things that kept her sane.) Emma finally looked up when an unfamiliar voice startled her when she said, "Hi! I'm Jessie."

Quickly the blonde looked up and was speechless in front of the beauty that stood before her. Jessie had darkish red hair, not fiery, in fact you would kind of have to look closely to see that her hair was indeed red; it actually looked nice on her. Her smile was intoxicating with her juicy natural full set of lips matched with a cute mole. Another thing Emma noticed was her beautiful curves!

Jessie was not too thick but she wasn't skinny either. But the one thing Emma was focused on was her boobs! She couldn't keep her eyes of them! They were perfect! It wasn't as though Jessie was showing a lot of cleavage, in fact she was relatively conservative. But the overall shapes and the creamy-like texture was amazing! Emma hoped she would one day grow a set as fabulous as those are. She then looked a bit further down to gaze at the curvy hips which lead to a nicely shaped ass. She couldn't catch a good glimpse, but Jessie was turned slightly enough to make out the outline of her beautiful ass which caused Emma to give her famous sassy grin.

Meanwhile Jessie was standing stationary waiting for Emma to respond. It would seem like five minutes had passed and Emma was still admiring her body. It wasn't until Jessie called out to her until Emma broke her trance. Feeling a bit embarrassed, Emma tried to play it off by saying, "Sorry I was lost in thought. Hi I'm Emma! Are you the new nanny?"

Relieved that the rather awkward situation was over, Jessie then responded, "Yes, I will be staying with you guys to take care of you." That was music to Emma's ears and her beautiful sassy smile returned once again. "Excellent."

"So where's Bertram?" Emma asked as she looked around to see if they were alone.

"He just said, 'they're your problem now' and left," Jessie responded. It definitely sounded like something Bertram would say. Jessie then asked, "Where are the rest of your brothers and sisters?"

"They all have to stay back at school for a while for their after school activities." After hearing herself Emma realized that she had the house to herself with Jessie for at least 3-4 hours.

It wasn't as though Emma constantly thought about sex, in fact she only tried it twice. Unfortunately she lost her cherry to a one night stand after she thought her relationship was serious. But it was true, guys only care about sex. In any case, she hated it because the boy couldn't satisfy her and came way too quickly (all over her face too which repulsed her.).

After that terrible experience Emma experimented with girls and purposely found lesbian friends to experiment with. They were more than happy to try Emma, after all, she was gorgeous. The experience was a success, but Emma was a hopeless romantic and wanted there to be a connection or at least have a physical attraction.

This proved to be problematic for Emma because she was still attracted to guys but rarely was attracted to girls; she always saw their flaws (probably because she saw her own "flaws" too despite being flawless.). But Jessie was a radiant beauty and even though she never consider herself a lesbian, she would quickly admit it if it meant being with her.

"Hey Jessie let me help you with your bags and show you up to your room; it's right next to mine!" Emma said.

"Thank you Emma! That's so considerate of you."

As Jessie was getting settled in Emma offered to help her unpack and of course Jessie accepted, she did bring a lot of stuff after all and thought it be a nice bonding time with Emma. After some small talk Jessie interrupted and said, "Excuse me Emma, but where is the Ladies' Room?"

"Oh it's just down the hall to your right," Emma explained.

Jessie proceeded with a "Thank you!"

Emma was sorting through the boxes of Jessie's stuff feeling a little annoyed that her seduction plot was not going anywhere. She knew she couldn't simply tackle Jessie, rip off her clothes and make love to her even if the thought was enticing.

The box she was looking through was finally empty so Emma grabbed another box and began sifting through it. What she found instantly turned her on! She was so ecstatic that she could burst at any moment. But she did not want to be caught; how awkward would that be if Jessie caught her? Thusly, she put Pandora's Box down and crept towards the door and closed it ever so gently. She quickly turned around and said, "It's just you and me now."

She ran towards the box and grabbed a handful of Jessie's bras and panties. She quickly became accustomed to Jessie's bra size which was a 38 C. Picturing her breasts in this cheaply made bra was making her panties wet. In fact, it wasn't long until she dove face first into Jessie panties. There Jessie panties would sit upon the delicate face of Emma while she furiously began rubbing her pussy.

Her moment of ecstasy was cut short when she heard footsteps coming from down the hall. Emma quickly pulled her hand out her shorts, buttoned them back up and put most of the undergarments back in the box. Jessie walked in and saw one of her bras next to Emma and said, "Oops sorry, let me take this box. I guess I should have labeled them. I'm sorry you had to see that." "DAMN!" thought Emma. "No, really Jessie it's ok. It's not like you have anything I don't."

They stood quiet the rest of the time, but mainly because Emma was trying to picture Jessie in just the bra and panties and without out them as well.

Jessie broke the silence with, "So I hear you have your own clothing line huh? Your Mom must be so proud."

And just like that, Emma's happiness was turned into sorrow. Jessie couldn't help but see Emma's change of character and then seen a tear roll down the soft cheek of Emma. Of course Jessie was concerned and asked what was wrong.

All Emma could do was start crying uncontrollably. Emma began to try and speak, but to no avail and Jessie quickly took Emma into her arms and soon Emma's face was being brushed by Jessie's soft and amazing breasts. That made her feel a little better, but Emma was still a bit upset. She knew Jessie didn't intentionally mean to make her cry. Finally after a long hug Emma was able to dry her eyes and speak.

"I feel so alone. My parents are always busy with their careers and I'm grateful for them providing me with a nice life, but sometimes I just wish I could talk to my Mom. Get some advice, have some girl talk; it would have been nice for her to explain puberty to me rather than having the school nurse teach me everything."

Jessie then broke the hug and looked at Emma and said, "Your parents are trying to do what's best for you and sometimes they do get caught up in their own lives but that doesn't mean they don't love you."

Emma interrupted by saying, "I'm sorry Jessie but that's a lie and you know it. They really could care less and I'm pretty sure they find me ugly because they almost seem embarrassed about me being a model."

The newly hired babysitter was stunned that the daughter of an actress would feel this way and she felt sorry for Emma. "Emma, well I can't speak for your mother, but I can say that I am looking straight at you with no makeup and see this extremely beautiful young woman and if nobody sees that, then they are absolutely blind."

Emma was thrilled to hear that from Jessie and proceeded to dry eyes and barely containing herself asked Jessie, "Do you really think that I'm beautiful?!!!" Jessie smiled and said "Of course I do."

After long lustful stare at Jessie, Emma smiled sweetly and hugged Jessie. Emma then broke the intense hug and went in quickly for a kiss all the while grabbing Jessie's left breast. There really wasn't a kiss because Jessie did not reciprocate but the key thing for Emma was the feeling of Jessie's breast. It's as if she felt that Jessie's boob belonged cupped in her hand and hopefully become more intimate with them later on.

Jessie felt Emma's tongue gently trying to find a way into her mouth of course Jessie was appalled especially when she felt this young girl copping a feel on her tits. It certainly explained why she kept staring at her but it was so wrong on all levels. She thought Emma was cute, but the thought of even remotely enjoying what was being forced upon her made her like a pedophile. Thusly, she pushed Emma off and as Emma tried again she put her hand on her forehead and said, "You need to stop!" in a demanding tone.

Emma was a bit shocked and perturbed, she was never denied by anyone but she ceased what she was doing to at least hear Jessie out. "Look, I think you got caught up in your emotions and it got the better of you but you and I can never go through that again. It's inappropriate, I'm not only older than you, but I am not gay. Besides, why would you come on to me when you barely know me? I hope you don't do this to everyone you meet," explained Jessie.

"I'm sorry if I came on a little strong, I didn't mean to freak you out. And no I am not a slut that throws themselves on to people. It's just, you are so pretty and have a rockin body and have the world's best personality so in my book that's all I need," stated Emma.

"Hey, I didn't mean to sound like I was accusing you of being a slut I was just taken back. I am flattered that you find me attractive but I am still not gay nor would it be right to take advantage of a young girl like you," explained Jessie.

Emma quickly answered, "You wouldn't be taking advantage of me! Trust me, I want you! I want you so bad that I think I may have came in my panties while fondling your exquisite tits. And how do you know you are not gay or at least bisexual? Have you ever made out with a girl?"

Jessie couldn't believe what she was hearing. Emma couldn't be older than 13 years old and yet she was talking like her horny friend back in Texas. The only difference was her friend talked this way about a guy and not her. It's not as though Jessie didn't find Emma attractive. She did notice her developing young body. Maybe she didn't have a rack or a nice ass but her slender figure and flawless skin was admirable.

"No, I have not had any feelings about a girl, but this convo is over," Jessie demanded. As Jessie was escorting Emma to the door Emma quickly turned and provided an option. "Alright, I'll tell you what, all I want is one kiss and one kiss only. If you can stop and I mean without forcing yourself to stop, then I turn around, walk out the door and will ignore you like I do with my other nannies."

Jessie again was beside herself with this girl, but if all it would take to shut this girl up is one kiss then she was all for it. After all, she wasn't gay so she was sure that she could break it easily.

"Ok, here is the deal. One kiss. No groping, no other attempt if I break it. Got it?" Emma emphatically agreed.

Emma wrapped her arms around Jessie's body which send sensational shockwaves already to Jessie. She didn't know it at the time, but she was strangely being turned on. They both took one last look at each other while Emma grinned from ear to ear and pressed forward for the kiss. As soon as both girls' juice lips made contact, there was an instant connection. Emma slid her tongue into Jessie's mouth and was greeted by Jessie's tongue. It was like their tongues were meant to be together.

The kiss finally broke after a few seconds and Jessie was amazed on how much she enjoyed it. It was perfect and seemed just too right not to enjoy. Emma sat for a moment looking at Jessie who was now lost in her thoughts until she finally said, "Earth to Jessie! Did you like it or not?"

Jessie didn't say a word but pushed Emma on her bed and began making out with her. Jessie began sliding Emma's shirt upward just enough to see more of Emma's milky white skin. She was now forcing her tongue into Emma's mouth.

Emma was a little shocked that Jessie was being so cooperative, of course she didn't mind at all. Jessie guided Emma's shirt off, breaking the kiss momentarily, which left Emma in just her bra. Their lips met once more and it almost felt like they missed each other for days despite only taking a few seconds off. While the two where passionately kissing, Jessie struggled yet managed to unclasp Emma's bra. They were still making out when Emma's bra hit the floor which revealed small, yet cute tiny breasts.

The tiny mounds were almost overcome by the now hard pink nipples. As Jessie looked down to cup the tiny tits, she finally broke the kiss to say, "They are so cute!"

Emma smirked and said, "Well they are nowhere near as beautiful as yours are."

Jessie countered by saying, "Bigger isn't always better...well most of the time." They shared a quick laugh and Jessie laid Emma down on the bed once again.

Jessie put her face on Emma's soft stomach and fell in love. She then dragged tongue just below Emma's navel and moved upward. The intense stimulation made Emma wet her panties even more. It was strange, Emma had intercourse before but this time with Jessie made her feel like she was a virgin even though she wasn't.

Jessie was now dragging her tongue near Emma's navel and would sometimes go down for a kiss. Each time this happened, Emma would let out a soft moan. "Ooo, that feels so nice." Jessie gave a seductive smile and said, "You haven't felt anything yet."

She winked and then began tonguing Emma's navel. "Was it possible to cum from a little tonguing in the naval?" Emma thought.

Jessie finally moved her mouth just below Emma's breast. She looked up, gave Emma a quick kiss, licked her lips and proceeded to flick Emma's nipples with her tongue. "Oh God Jessie, that feel's incredible!"

Jessie then placed her entire mouth around the tiny mounds and gave one huge suck. "Oh yea, like that!" She then sucked solely on her nipples which made Emma just lose it. "Harder! Bite them pleaaaaseeee!!!!"

Jessie of course accommodated by teasing her young breasts with small, gentle bites. Emma then rubbed pussy furiously and came harder than she ever had in her life. "OOOOOOOOO I'm CUMMMMINNNNGG!!!!"

Curious just how much came she looked at her tight shorts and was surprised to see the wet stain in the crotch region. "Wow Emma, if you came already then you're REALLY going to enjoy what else I have in store for you!"

Emma a bit embarrassed responded, "Well let's see how you handle what I'm going to do to you!"

She then stood Jessie up, removed the conservative top and revealed her cheap white bra. "Your lovely boobs deserve better than this," Emma teased.

"I'm broke ok!" Jessie snarled.

Emma then unhooked her and just watch the lovely bags of flesh just drop before her very eyes. Emma sat on the bed and her eyes were at nipple level with Jessie. Unsurprisingly, Jessie's nipples were hard too but her nipples appeared smaller since there was much more boobs.

Emma rubbed her face in between Jessie's tits and wanted to just marry them! She began suckling on Jessie's nipples while Jessie was standing. Soft moans were coming from Jessie, "Mmmmmm. Oh Emma that feels soooo nice!" Unfortunately, Jessie was becoming a little uncomfortable with standing so she removed Emma from her right breast and took off her pants.

Emma decided to do the same and both also removed their panties. They both gazed at each other's lovely naked bodies. Jessie sat down on the bed and had Emma on her lap. She then began to cradle her. Emma's smooth ass grazing Jessie's leg was turning her on.

Emma was wondering why Jessie had begun to cradle her but it all made sense when Jessie delicious tits were within mouth range. In some bizarre way it was almost like Jessie was breast-feeding Emma. She didn't mind of course because her boobs were so perfect.

Once again Emma begun suckling on Jessie's tits. First licking her nipples up and down and then began nursing the ripe tits. "That's right Emma just like that. There we go. Ooooooo getting a little hungry aren't we?"

Emma could have stood there forever, but Jessie wanted a taste of Emma. So she separated Emma from her tits again and laid on the bed and guided Emma to the 69 position. Emma smiled licked her lips and dove straight into Jessie's twat. It didn't take long before Jessie would began the eating of Emma's young cunt.

"Mmmmm!!! MmmMMMMMMmmm!!!" Both girls devoured each other's cunts taking turns lapping away at their clits. To Jessie's surprise, Emma was far better at eating pussy then she was and ceased her licking when Emma had her close to her climax.

"OHHH SHIIIIITTTT!!!! EMMMMMMMAAAAA!!! No don't stop! Don't YOU DARE!" Emma was now plunging her finger inside and out of Jessie's pussy which only caused more juices to flow out. The new tangy flavor caused Emma to rise out of Jessie's crotch and say, "Mmmmm sooo delish!" Jessie didn't say anything but shoved Emma's face back into her pussy.

Once again, Emma was mercilessly lapping away at Jessie's clit. "Oh yes! YES YES YES YES!!!! FuCK ME!!!! Oh GOD!!!! I'm CUUMMMMMINNG!!!" Jessie began to thrust her pelvis up and down, but it didn't matter because she was not getting away from Emma's tongue.

Emma was gathering all the cum that was spurting out Jessie's delectable twat. After all of it was consumed, Emma gave Jessie's pussy one last lick, then kissed it and said, "WOW! That was the best thing I ever tasted. Who knew you could taste so sweet?" Jessie blushed and began to lick Emma's clit.

The sensation was amazing to Emma but she still had bragging rights for making Jessie cum first. "So who exactly cums easily?"

Jessie stopped the licking and admitted, "Ok so maybe you are better at eating pussy then me, but I promised I would make you cum again and damnit I will!"

Emma smiled and said, "Prove it! I'm pretty sure you can't match my pussy eating skills." Jessie smirked and said "Who said I had to eat your pussy?"

Puzzled by the weird statement, Emma was at a loss for words. It didn't matter really because while she was trying to process it, Jessie had already stood up, grabbed a pillow and put the pillow on the floor next to the wall. Still a little confused she listened to Jessie say, "Just put your hands on the wall, rest your face on the wall and stick your ass out."

Emma obeyed despite still being curious as to what Jessie was exactly doing. Jessie on the other hand was determined not to be outshined by a 13-year-old. She was inspired while in the 69 position. Jessie kneeled down until she was face to ass with Emma's ass.

She began to immerse Emma's cute little ass with small kisses. The softness Emma's ass was amazing as it brushed Jessie's lips. Emma had to admit it felt good despite being a little odd. Jessie would rotate licking, kissing and biting the cute little bottom. Then things would definitely get a little weird.

Jessie gave a gigantic smack on Emma's ass. "OWWW! Hey! What was that for?!" Jessie didn't say anything, just kissed and licked the area that was spanked. She repeated this process several times until Emma felt something that kind of bothered her.

She felt her ass checks being spread which was an odd feeling to her, "Uhhhh Jessie, what are you doing." Silence. Jessie was actually at a battle with herself, her whole purpose was to begin licking Emma's asshole but it just seemed dirty and gross. But looking at Emma's clean little hole actually seemed inviting. Emma was just about to move when she felt the weirdest sensation she had ever felt in her life.

Jessie had licked her asshole! And to Jessie's surprise, it tasted extremely good! Emma of course contested, "JESSIIIIEEE!!!! WHAT ARE YOU DOING????!!!!" She started turn around but was met with Jessie's hand on her back forcing her to stay in that position.

Once again, Jessie spread Emma's cheeks and lapped away at Emma's puckered asshole. Emma couldn't believe what was happening, she didn't know whether she liked it or was grossed out. But she did feel her pussy lips begin to drip. Either way, Jessie wanted her asshole and there was no getting away from the relentless tonguing in her ass so she might as well enjoy it.

Jessie licks were becoming faster and faster, she was licking like a mad woman! "OOOOHHHH MYYYY GODDD!!! JESSSIIIIIIIEEE THIS IS SO WRONG!!! But UHHHHHHH!!! It feels SOOOO Uhhhhhh FUCKING GOOD!"

Jessie ceased tonguing and dropped both cheeks and made the two mounds hit each other and jiggle a bit. "Young lady I will not tolerate such language! You will be punished!"

Emma bit her bottom lip as Jessie proceeded to spread her cheeks again, this time as far apart as they could go then she drilled her tongue inside Emma's asshole. "EIIIIIIEEEEE!!!! JESSIE IT HURTS! OH MY GOD!!!!"

Jessie just kept on drilling. It hurt for a little while, but then it was the best feeling Emma had ever felt. "YEA!!! Oh YEA! HELL YEA!!!! That's right Jessie stick your tongue deep in my ass!!!" Jessie then went as deep as she could! She went so deep that her entire tongue was wedged in little Emma's ass.

"LIKE THAT OH MY GOD!!!" Jessie had all her tongue in her ass and was now sucking on it her hole. "OPEN YOU MOUTH BECAUSE I'M CUMMINNG!!! UHHHHHHHHH!!!!!!!!!!!!"

Jessie removed her tongue from Emma's asshole and went underneath and in between her legs to drink every last drop of her cum. Emma came harder than the first time! When Jessie was finished, she gave one last glance at Emma's ass and gave it a kiss goodbye.

Jessie stood up and wrapped her arms around Emma; her nipples tickling Emma's back as she was dry humping Emma's ass. She turned Emma's face and gave her a satisfying kiss. She could taste remnants of her own ass on Jessie's tongue because after all she went deep enough. She loved the flavor and hoped to return the favor to Jessie.

Just when she was about to make her move, they both heard a shout from Robbie, Emma's brother, "Emma! Jessie? Where are you?!"

"I'm not finished with you yet!" Emma explained as she ended the convo with a long lick to Jessie's face. "I don't think I've had enough of that ass either" as she quickly dropped to her knees and licked the puckered hole one last time.

They both quickly gathered their clothes and put them on. They both heard a knock and Robbie walked in said, "Why are you two sweaty?"

Jessie responded, "Oh you know, moving in is a lot of work."

Robbie caught a whiff of Jessie's breath and said, "Mmmm what did you eat it smells good! I'm hungry now! Jessie do you mind making me something to eat?"

"Of course sweetie just go to the kitchen table and whip something up real quick."

As soon as Robbie left, Jessie winked and said "I ate something very delicious and that ass will be mine again very soon." All Emma could do is smile.

    

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