This is a work of fiction. The characters are from the Disney Channel TV show, "Jessie." The event took place in the author's imagination.
(Lesbian Celebrity. Ff)
14-year-old Emma Ross was feeling sad and alone. On the surface she should have been the happiest girl in the world. She was from a wealthy family, lived in a luxury penthouse apartment in Manhattan, attended a prestigious high school, and dressed in only the latest and most expensive fashions.
However, once you scratched the surface, you found a lonely teenager whose body was maturing faster than her thoughts and emotions. Emma had a group of younger siblings that she no longer felt that she had things in common with, and had parents who were never home, and they left her emotional support up to a crusty butler and loving, if somewhat incompetent nanny. Emma was never quite sure if her friends were really her friends.
Emma had hit a growth spurt between ages 13 and 14. Her maturing looks had caught the interest of older boys and even some college-age men. Unfortunately, once it became clear that she wasn't going to put out, there was rarely additional interest. Her nanny, Jessie Prescott, could offer no practical advice, as her own dating life was a mess.
Even more scary for Emma. she felt she might be more attracted to girls. Puberty had really thrown Emma for a loop. Her hormones were always racing, and she often found herself staring at Jessie's large tits and imagining herself sucking on them. At night she masturbated to internet pictures of Selena Gomez, Olivia Holt and Miley Cyrus from her favorite Disney Channel shows.
Bored one Saturday afternoon, Emma wandered down to the apartment of the oft-married and oft-widowed Rhoda Chesterfield. Mrs. Chesterfield was no fan of the bratty younger Ross children, but she had taken a special shine to the pretty, blonde Emma. She had once even given Emma a beautiful vintage dress.
Mrs. Chesterfield was not good with names and often called the teen Jemma, instead of Emma. Emma didn't seem to mind. She was just happy to have someone to talk to that wasn't impressed by her wealth or famous parents. Mrs. Chesterfield had made it known to Emma that she was welcome to stop by any time.
Emma had promised to show Mrs. Chesterfield some of the new Spring fashions that she had recently received from designer friends of her mother. So, armed with several bags and boxes she rang the bell to Mrs. Chesterfield's luxury apartment.
Mrs. Chesterfield was delighted to see the teen. She didn't have many visitors. Emma looked particularly bright and pretty that day. She was wearing a pink ruffled miniskirt which accentuated her long, lean legs. At 14-years-old she was already nearly 5'8" tall, and was a head taller than some of her female classmates. Her outfit was capped off by a form-fitting sweater top with a slightly bare midriff that showed her belly button and seemed to spotlight her perky, young breasts. Mrs. Chesterfield thought that young Emma looked good enough to eat!
The older woman helped Emma with her packages and the pair retreated to the bedroom where Mrs. Chesterfield had a floor-length three-way mirror. Emma laid the various outfits out on the bed, and the two discussed which ones they particularly liked, and which ones Emma should try on first. Mrs. Chesterfield dressed eccentrically for effect, but she was actually quite helpful to Emma in selecting combinations and choosing which colors worked best with her peaches and cream skin tones.
After retreating to the master bathroom a couple of times to change outfits. Mrs. Chesterfield suggested that Emma simply change in the bedroom to save time. "After all, it's just us girls," Mrs. Chesterfield reasoned. Emma smiled her pretty smile and nodded her head.
Slipping off her dress, Emma stood before the mirror in a sexy, lacy white bra and panty set. With the three mirrors, Mrs. Chesterfield could soak in every luscious inch of Emma's 14-year-old body. Emma's long, lean legs led up to to a small, firm ass. Emma's butt cheeks were revealed by her t-back bikini underwear. Her breasts were small but perky. A hint of cleavage was revealed by her sexy A-cup bra.
Rhoda Chesterfield sat in a plush chair just feet away from the nearly-naked teen princess. Mrs. Chesterfield always seemed to be in a marriage to a rich older man, and had never given women or girls much thought sexually. However, looking at the glorious developing body of the beautiful teen in front on her, her sexual desires began to awaken.
As the day moved along, and there were more outfits to try on and take off, Rhoda became more actively involved. Helping with adjustments, Mrs. Chesterfield's hands would "accidentally" brush against Emma's breasts, stomach, and ass. Rhoda became frustrated with Emma's seeming obliviousness to her sexual hints.
Finally, when Emma was once again in bra and panties, Mrs. Chesterfield boldly made her move. She ran her fingers gently along Emma's flat stomach and said, "Emma, my dear. You have the most gorgeous skin, it's absolutely flawless. "Thanks?" was all that Emma could questioningly reply.
Noticing that Emma was not pulling away from her touch, Rhoda began tracing her fingers along Emma's lacy white bra. "And your breasts, they look so smooth. You're really doing a disservice at your age by even wearing a bra. Would you mind?" Without waiting for a response, Mrs. Chesterfield quickly removed Emma's bra. Emma's teenage breasts were milky white with pinkish nipples and areola. They were somewhat conical shaped and stood proudly, without even a hint of sag.
Emma didn't know what to think. Frankly, she was happy that someone, anyone, was giving her a full afternoon's worth of attention. God knows she hadn't seen her busy and inattentive mother or father in weeks
Emma trembled a little as Mrs. Chesterfield tenderly caressed her small, young boobs. Mrs. Chesterfield's fingernails caused Emma's nipples to become engorged and erect.
"Yes, my dear. They're more beautiful than I can describe. You're really one of the prettiest girls that I've ever seen, and as you know I used to be a model."
Mrs. Chesterfield was arms-length from Emma as she continued to gently caress Emma's young breasts. Mrs. Chesterfield tapped and circled Emma's erect pink nipples. Mrs. Chesterfield slowly moved two steps closer to the teen and passionately kissed her. Emma surprised herself by reciprocating. Soon their tongues were intertwined and thrusting greedily. Emma could feel the older woman's saliva all over her carefully made up lips.
Emma had not uttered a word, but also had not put up any resistance. If Mrs. Chesterfield wanted to make out and cop a feel, Emma was O.K. with rewarding her older friend. Emma had not begun to contemplate how far she would let the middle-aged woman take it.
Mrs. Chesterfield put both hands on Emma's face and gave her a deep open-mouthed kiss. Emma had never French-kissed before that day and it felt warm and nice. Mrs. Chesterfield's hands moved down Emma's smooth back before cupping Emma's firm, young butt. Emma was now acting on instinct and began to kiss Mrs. Chesterfield's neck and run her hands along Mrs. Chesterfield's breasts. Emma could feel Rhoda's hard bra underneath her dress.
In an instant, Emma's panties were on the floor and Mrs. Chesterfield was rubbing the sparse blonde hairs above Emma's young pussy. Emma hadn't anticipated going that far, and tried to cover her naked pussy with her hand.
Mrs. Chesterfield would not relent, and lifted Emma's now-naked body onto a nearby dressing table. She began licking and kissing Emma's small breasts. Emma closed her eyes tightly to prepare for whatever was next. Emma felt a finger enter her tight pussy and then a tongue. Emma's entire body shuddered as she was penetrated for the first time.
As Emma opened her eyes, she could see Mrs. Chesterfield engaging her pussy like a ravenous animal, shaking her head up and down and from side to side as she devoured her tender prey.
Emma had to admit that it felt good... really good. Her ensuing orgasm was a revelation.
Mrs. Chesterfield unzipped her dress and proffered a sagging breast to Emma's mouth. Emma sucked and licked to the best of her ability, but was more interested in being serviced than servicing the older woman.
Mrs. Chesterfield licked and kissed every inch of Emma's taut 14-year-old body before she went home. Emma's pussy was sore from the older woman's attention, but she had greatly enjoyed the experience.
Emma had been planning her next encounter for weeks. Her siblings, Luke, Ravi, and Zuri were going to be joining their parents in Hawaii. Bertram, the butler, was to accompany them on the plane. Emma had an important midterm science test, and would be flying in a couple of days later with Jessie, the nanny.
With only Jessie and Emma in the house, Emma began her plan of seduction. Pretending to have had a bad dream, Emma knocked on Jessie's bedroom door. Emma was wearing only a very sheer nightgown and black panties. The short nightgown was sheer and see-through, and Emma's small tits were prominently visible to the pretty, red-haired, 20-year-old nanny
Emma explained to Jessie that she was afraid to go back into her bedroom alone, and asked if she could go to sleep in Jessie's bed. Jessie inquired if Emma always wore such sexy clothes to bed and Jessie couldn't help to miss Emma's breasts poking through the sheer fabric.
Thinking that Emma was freaked out from her bad dream, Jessie hugged the teen and kissed her on the forehead, telling her that there was nothing to be afraid of, and to go to sleep. Jessie opened the covers so that the teen could slide in.
Emma snuggled up closely to Jessie's warm body in the spooning position and positioned a hand on one of Jessie's large breasts. Failing to get her attention as Jessie was trying to go back to sleep, Emma began to squeeze and massage the breast.
This caused Jessie to sit up and push down the bedcovers and turn on the light. "Whaaat are you doing?!" Jessie asked in her sternest voice. Jessie noticed that Emma's nightgown was open and that her small, naked, pink breasts seemed to be pointing at her.
Jessie was wearing only a cropped Texas Longhorns t-shirt that exposed her belly, and a small pair of red bikini panties. Emma boldly put her hand underneath Jessie's shirt and began squeezing a bare breast. Jessie was too flabbergasted to remove Emma's wandering hand.
"Jessie, I want to make love to you," Emma said. The words nearly floored Jessie. She had been Emma's nanny since she Emma was a flat-chested 12-year-old. Jessie had to admit that Emma was turning into a very sexy young girl, and the perky naked breasts in front of her were making her mouth water.
"But you're only 14," Jessie said, trying to convince herself that she shouldn't. "But I'm tall for my age," came Emma's ditzy reply. Emma began to rub her small tits and tease her nipples for Jessie's benefit. Jessie wanted to give the 14-year-old one last out: "Are you sure?" Emma nodded her head. "Very," came Emma's reply.
Jessie began to caress one of of Emma's A-cup breasts. Emma's nipple was as hard as a pencil eraser. "O.K., but you've got to promise me that no one will ever know about this. I don't want to lose my job... or go to prison," Jessie said with a snort.
As Emma removed her nightgown, Jessie pulled her t-shirt over her head. "Wow," was all Emma could say as she looked at Jessie's large, full breasts. They were even bigger and rounder than Emma had imagined... and she had imagined plenty. Jessie laughed at the speed with which Emma crawled over her body to get at her enticing fun bags. One breast was quickly in Emma's mouth, and one was being quizzically fondled by her eager hand.
Jessie placed one of her hands underneath Emma's black panties and began to stroke her slit. Jessie noticed that Emma's pubic area was almost bare to the touch, but the few hairs were smooth and silky. Jessie thought, "Emma even conditions her pubic hair."
While continuing to suckle one of Jessie's breasts, Emma began to rub her hand on the outside of Jessie's panties. Jessie was starting to get hot from the teenager. Jessie reflected for a moment on the time when she had first started working for the Ross family and Emma's mother had seduced her when she was only 18.
Christina Ross was a beautiful, blonde, former model. One weekend Christina was in-between personal assistants and invited Jessie to accompany her to London. The next thing that Jessie knew, Christina's head was between her legs with her tongue in her pussy. The sex had been great, and little Emma was promising to be a similar, if younger, delight.
The memories of Christina and her beautiful tits and wet pussy were getting Jessie hot. She threw open the bedcovers and kicked them to the floor. Jessie whipped off her panties and threw them across the room. Emma was fascinated by Jessie's completely shaven pussy. When Jessie started dyeing her hair red, she found it too much trouble to dye her pubic hair too, so she simply shaved it off.
Jessie reached over to Emma and pulled her panties off, and similarly threw them across the room. Jessie began kissing and licking Emma's stomach, which caused her to giggle. Jessie worked her way down Emma's body until she was at her pussy. Jessie stroked Emma's soft, golden pubic hair and closed slit before penetrating the teen with tongue and fingers. With no one home, Jessie made no attempts to stifle Emma's little squeals of pleasure as she attempted to insert her tongue as deeply as it would go in the precocious teen.
Reaching into a nearby drawer, Jessie emerged with a small dildo which she quickly inserted into Emma's pussy. Even with a small dildo, it was a challenge to manipulate it an and out of Emma's tight, young cunt. Turning the dildo over to Emma to continue, Jessie began to kiss, lick and stroke Emma's long, lean, legs.
With Emma laying on her back her small breasts all but disappeared, although her pink nipples remained erect over her lean torso. Jessie was anxious to suck Emma's breasts and to compare them with Christine's. Jessie pulled Emma off the bed until both girls were standing in the room. Both enjoyed the opportunity to get an unobstructed view of the other's full, naked body. Emma's hand quickly went between Jessie's legs before it could be pulled away. Emma let out an "Aww" sound.
Jessie gazed at every inch of the slender girl under her bright bedroom lights. Emma's skin was flawless, and her cute, tiny ass begged to be kissed and worshipped. Jessie inserted one of Emma's A-cup breasts into her mouth nearly whole. As it emerged, Jessie's teeth were clamped onto Emma's pink nipple as she nibbled and suckled it.
With the young lovers still standing, Jessie attempted to insert a licked finger into Emma's anus. The 14-year-old squirmed and struggled in resistance, but Jessie was much stronger and held her still. Eventually, the finger began to slide in and out much more easily and Emma was surprised at how good it felt.
Jessie then suggested for Emma to finger-fuck her. Emma serviced Jessie while on her knees, with her left hand holding on to Jessie's fleshy ass to hold her in place as her pelvis shuddered. Emma felt a sense of accomplishment as she brought her nanny to a shaky-legged orgasm.
Jessie hugged and kissed the teenager. Emma's young, slender body felt so good in Jessie's arms. Emma's skin was so smooth that Jessie lingered while caressing Emma's back and arms. Emma's tongue seemingly became more skilled with every kiss.
Still in an embrace, Jessie picked up Emma by her tiny ass, and they both fell on the bed. Jessie crawled to the head of the bed and rested her back on the headboard. Wordlessly, she opened her legs in an unspoken request for Emma to perform cunnilingus on her bald pussy.
Emma hesitated. Not only had she not eaten Mrs. Chesterfield's pussy, Mrs. Chesterfield hadn't even gotten naked, Emma gratefully thought.
As Emma approached Jessie on her knees, she truthfully said, "I've never done this before." Jessie assured Emma that she would do fine. Emma gave a tentative lick, and then another, and then another. It was a little sloppy and not very skillful, but just looking at Emma's pretty face between her legs caused Jessie to cum. Emma's blonde ponytail shook from side-to-side as she lapped increasingly vigorously at her nanny's hairless pussy.
Now Jessie got on all fours and gave a final request. Handing the small dildo to Emma, Jessie requested that the 14-year-old lube Jessie's anus with her tongue before inserting the dildo. Emma froze for a second, then did what she was told. She always did what Jessie told her.
Emma circled Jessie's asshole with her tongue. Fearing a bad smell or taste, Emma was relieved that there was neither. Jessie's low moans encouraged the 14-year-old blonde that she was at least working in the right direction. Adhering to Jessie's pleas, Emma straightened her tongue and inserted it as forcefully and deeply as she could. Forgetting about the dildo, Emma brought Jessie to her deepest orgasm as she collapsed onto the bed.
With Jessie in a prone position laying on her stomach, Emma mounted the nanny and began humping her fleshy backside. Pounding away with all 105 pounds of force, Emma began kissing Jessie's neck while breathing hard.
Jessie asked her, "Have you done this before?" Before Emma could answer, Jessie replied, "Wait. Don't tell me."
After more playful sex, Emma fell asleep naked on Jessie's full breasts. As Jessie stroked Emma's golden hair she wondered if this would be a one-off thing like with Emma's mother? Or, perhaps, she could somehow get the both of them together in the sack? Jessie smiled at the thought.
As she started drifting off to sleep, Jessie thought, "If Luke ever finds out I'll probably have to blow him..."
The End