This is a work of fiction and a bisexual fantasy involving the cast of the Disney Channel TV show, "Jessie." None of these events ever happened, and existed only in the mind of the author. If you are offended by the subject matter, please stop reading now.
(Bisexual Celebrity, FM, Fm, Mf, Ff, Mm, Ffm)
Jessie Prescott had been nanny to the four Ross children for two years. She wasn't the most competent or highly-trained nanny in the world, but she deeply loved the children, and their parents knew that she would protect them with her life.
Morgan and Christina Ross were moguls, with business ventures ranging from movie production to fashion. They were a busy pair, and sadly they were rarely home for their four children. Emma, the oldest, was 14-years-old and becoming a real blonde beauty. The other three children had been adopted: Luke, age 13; Ravi, age 11; and precocious Zuri, was only 9.
The Ross's had added children to their family from different races: Luke was bi-racial, Ravi was adopted from India, and Zuri was adopted from Kenya. The Ross's were certainly not prejudiced. It's just a shame that they didn't have more time for their children.
Jessie took care of the kids, and Bertram, the butler, did the cooking and cleaning.
The elementary school year had ended a week earlier than the grade 7-12 school that Emma and Luke were attending. The younger children had gone to California to join their parents who were working on a production there. Bertram had accompanied Ravi and Zuri on the plane.
Luke, Emma, and Jessie would be joining the Ross parents the following week after school had concluded.
Emma, Jessie had noticed, was becoming more stunning by the day. As only a 14-year-old freshman, Emma had the long, lean looks and golden blonde hair of a future fashion model. At her young age she was already approaching 5'8" in height.
Jessie, at only 20-years-old had her eyes on the pretty 14-year-old, and would offer her assistance when she was bathing or changing clothes. Emma hadn't seemed to figure out that Jessie was checking her out in her various stages of undress. Jessie would love to somehow fuck the young girl, but she didn't want to lose her job... or go to the slammer. Besides, she would never be able to get Emma alone. Jessie would have to content herself with sneaking a peek whenever possible.
Although Jessie had been dating cute, but dumb, doorman Tony Chiccolini for nearly a year, she was secretly bisexual, as was Tony. Unbeknownst to the Ross family, they had attended several bisexual swingers parties in Manhattan. The attractive couple were a popular pair for both sexes.
Tony was a lean, handsome "top" with an 8" dick. He enjoyed sticking it into any willing orifice, and was eagerly sought out by men and women for his prowess and stamina.
Jessie was pursued for her large breasts which she enjoyed having licked. She was equally good at eating pussy as she was giving blow jobs. More than intercourse, she preferred being eaten out by anyone skilled at cunnilingus.
Working for the Ross family afforded Jesse an affluent lifestyle, and allowed her the opportunity to occasionally audition (and fail) at acting cattle calls.
The Ross children could be exasperating, but Jessie genuinely cared for them. While Emma was pretty and nice, Luke Ross was a handful. He was at that horny age where puberty was causing him a continual, and sometimes embarrassing erection. Jessie had noticed Luke's penis standing at attention on innumerable occasions, particularly when he was wearing sweats or loose athletic shorts. Jessie had never seen Luke's sword unsheathed, but it appeared to be of an impressive size.
Jessie was Luke's particular subject of horny interest. He was always trying to catch Jessie undressed, which she was flattered by on some weird level. When she would speak with Luke she would often catch him talking to her bountiful tits rather than her eyes. She would tilt his head up by the chin and say, "My eyes are up here." Luke was never as shameful as he should have been.
As part of her unwritten contract, Jessie was told that she was in no uncertain terms allowed to have male visitors spend the night. Christina, their mother, felt that the children were still at an impressionable age, and they would have questions that Christina didn't want to have answered quite yet. Christina was kind of a prude when it came to Jessie.
Naturally, this was an inconvenient rule for a young woman with a boyfriend. While the bisexual swinger stuff was for nights out, she wished that Tony could stay over once in awhile. He had a crummy low-rent apartment, and Jessie hated to go there for sex. She was afraid that a rat or a cockroach would jump on her.
With most of the household in California, Jessie decided to risk it. She and Tony would watch TV until Emma and Luke had gone to sleep, and then she would sneak him into her room, making sure that he left in the wee hours before the kids got up. No one would be any the wiser, she thought.
Emma had overheard whispers of the plan and shared it with her brother, Luke. Emma was almost as infatuated with Tony as Luke was with Jessie. They both agreed to go to bed early that night and pretend to be asleep when Jessie checked on them. They would meet later outside Jessie's bedroom door at a prearranged time.
At precisely 11:35 p.m. the Ross siblings quietly met outside Jessie's door. Other than eavesdropping, there was no particular plan beyond that. Luke thought Emma was crazy, and that the only thing they might hear was the Tonight Show on Jessie's TV. He believed that Jessie was a "good girl," and would always follow the rules. Besides, he didn't even want to think of that dumb Tony on top of his sweet Jessie.
Both Ross kids had just gotten up and planned to give it five minutes or so before returning to bed. Luke was bare-chested and was wearing a pair of diamond-patterned blue boxer shorts. Emma had not bothered to put on a robe and was wearing an undersized Jets jersey that exposed her smooth, flat belly, and a small pair of pastel pink bikini panties. Luke had to tell himself that the half-dressed hot blonde was his sister. Luke tried to think of any other subject that he could to keep an erection from coming at this inopportune time.
Luke had thought to bring a glass to better hear through the door... just in case. Emma watched in amazement as Luke's eyes appeared to bug out of his head. "They're fucking," he said in the lowest possible whisper. Emma mouthed a startled "What?" and motioned for Luke to hand her the glass so that she could hear. The telltale sounds of sex emanated from the opening of the water glass.
Fervid hand gestures and whispering began between the Ross siblings. Emma was turned on, and Luke was both incensed as well as turned on that someone was fucking his dream girl. Emma noticed that Luke's hard on was straining against his boxer shorts. Emma hoped that Luke didn't notice that her nipples were erect against the number 10 on the front of the football jersey she was wearing.
Emma began to point down the hallway, motioning for Luke to go back to bed. Luke shook his head vigorously "no," he was not leaving. Emma looked on in horror as Luke could stand it no longer and opened the door.
Jessie had Tony's penis in her mouth, so she was unable to scream in surprise. Luke was yelling but he was making very little sense. The gist seemed to be: "Our parents said you can't fuck Tony in the house."
Jessie was trying with her two small hands to hide her voluptuous naked body from the kids. She noticed that Luke's erection had poked out of the opening in his boxer shorts and was indeed of an impressive size for a 13-year-old.
Tony had gone flaccid when the door was first opened but was quickly hard again by looking at the nearly naked 14-year-old blonde, Emma standing in the doorway. Emma was equally checking out Tony. He was lean and muscular, and his erect thin circumcised cock was an impressive 8" long. Tony's body was completely smooth except for a small, carefully trimmed tuft of dark hair above his shaft.
Tony leered, and shifted his naked body in order to give Emma a better look. Meanwhile, Jessie was trying to cover herself and deal with the distraught and incoherent, Luke.
With the boy babbling, Jessie cut to the chase with Luke: "What do you want?" Jessie knew that one day she would probably have to blow Luke to keep him quiet for something she had done. It looked like that day was today. "What?" Luke asked. He wasn't really listening; he was so upset.
Jessie repeated slowly, "What do you want for you to stay quiet?" This time her voice was a mix of resignation and disgust. Luke realized that he would never have a better opportunity, so he lowered his boxers to the floor and grabbed his pecker. announcing, "I want to fuck you. I've always wanted to fuck you."
Even Tony was impressed by Luke's 5" penis. It was so engorged with blood and semen that it was literally bobbing up and down. Being bisexual, he hoped that Jessie would agree to Luke's terms, and he could have a go at the boy before the night was out. Tony touched his cock as he fantasized about Luke's penis in his mouth,
Luke was a talented dancer and was now becoming a wiry type of muscular as puberty dawned. His 13-year-old penis was nearly hairless as was the rest of his now-naked body. A year prior he had talked Emma into giving him her first hand-job. She reluctantly agreed, but made Luke come into an old sock.
What a difference a year made to Emma. Luke, although still comparatively short, was certainly an attractive boy. Emma reminded herself that Luke was adopted and not a blood relative.
It had only been 10 seconds since Luke had responded, but it seemed like an eternity to all that were in the room awaiting Jessie's answer. Suddenly the air was split by Emma's unexpected terms, "And I want Tony to fuck me"
"Alright," Tony quickly and enthusiastically responded. Jessie smacked him in the arm, causing her exposed boob to bounce, much to Luke's delight.
The wheels in Jessie's head began to turn. She surely didn't want to lose this job. With no marketable skills she would have to go back home to Texas in disgrace. She knew that she would have to fuck Luke to ensure his silence. If Emma was part of the group, maybe she'd get a piece of her little pussy tonight too.
Finally, Jessie spoke: "If you want to play with the big kids tonight, O.K. But if word gets out Tony and I can get in a whole lot of trouble." Naked Luke jumped on the bed in anticipation, his dick waving at Jessie's eye level.
Jessie reached over and grabbed Tony's dick. She looked at Emma. "You're not on the pill, so if you insist on having sex with Tony, he HAS to wear a condom." Jessie shook Tony's dick at Emma and said, "Capish?" Emma nodded her head in agreement. Emma thought: "Was she really going to lose her virginity like this tonight? In front of her brother and her nanny?"
Before she could answer herown questions, a very naked Tony emerged from the bed. His blood-engorged 8" erection had a very slight curve to it. Tony pinched Emma's nipples which were firmly poking from the football jersey. In an instant, Tony had pulled the small Jets jersey over her head, revealing her small, but pointy breasts. He gave both breasts a quick squeeze and placed his large cock in Emma's hand.
Unlubricated, even Emma's touch was a little rough for a hand-job. Tony suggested that she try oral. Emma got on her knees and performed her first act of fellatio. She squeezed Tony's ass and played with his balls as she blew the 25-year-old. It was her first blow job. There's an old saying, some blow jobs are better than others, but they're all good. Tony offered ample warning, but Emma allowed herself to swallow Tony's load.
Meanwhile, Luke was up on Jessie, and he was ravishing her large tits with his tongue and mouth. As he couldn't decide which one he liked more, he quickly alternated between the two like a puppy running between two children.
Luke's hard-on kept slapping into Jessie as he moved excitedly from side-to-side. Finally, Jessie grabbed Luke's member and inserted it into her mouth. Luke let out an "Oh yea," as Jessie took his young penis deep into her experienced mouth. Looking to the side he noticed his older sister performing the same act on Tony. Luke was not only intrigued by his sisters' perky tits in comparison with Jessie's, he could also understand the girl's attraction to Tony. He looked like a Greek God to Luke, as he thrust his large penis into Emma's waiting mouth.
For a 13-year-old, Luke held out for a surprisingly long time while being blown. Jessie had decided to give the boy a once-in-a-lifetime full-bore treatment, as she began to lick and kiss his developing chest muscles. Luke's penis. like most boys his age, reloaded in just moments.
Emma was laying on the bed, still in her pink panties. Tony was giving himself an erection so that he could put on a condom in order to have intercourse with the willing blonde, 14-year-old. Tony began kissing Emma's pussy through her panties. When she was sufficiently wet, he pulled them off of her and slowly entered the teen with his penis. It was tight and a little painful at first for Emma, but within a minute or two it became a pleasurable experience as she caressed Tony's masculine body. There was no blood, as Emma had likely lost her hymen through sports or horse riding some time before.
Tony increased his speed and effort when Emma no longer felt any pain. Even Jessie was intrigued with watching her boyfriend fucking the barely teen beauty. At the swinger's parties that they had attended they usually separated. Jessie didn't particularly like watching Tony fucking other people, especially horny older men, of which he was a favorite.
Emma was gritting her teeth and holding her own as her light body moved up and down on the bed in tandem with Tony's increasingly firm body motions.
Luke also stopped what he was doing to watch. He was hoping to have a similar interlude with Jessie in a matter of moments and was intrigued to watch Tony's muscular body thrust in and out. "Why was he so interested in Tony?" Luke asked himself.
Luke had a firm grip on his 5" dick as he watched his teen sister being fucked. What happened next surprised even the perverted Luke.
As Emma laid flat on her back with her legs in the air and Tony firmly inside of her, Jessie crawled over and began to lick Emma's small tits and French kiss the 14-year-old. Much to Luke's surprise, Emma was reciprocating and had an arm around her nanny, trying to hold her close. "What the fuck?" Luke asked, as Tony simultaneously exploded in orgasm, falling off to the side of the bed.
Jessie was now free to explore the pretty teen further. Her lips and hands traversed nearly every inch of the long-limbed blonde teen. Emma was moaning in ecstasy. She too had an unexpressed sexual desire for the full-figured 20-year-old nanny.
Jessie was soon between Emma's legs and stroked her smooth, golden pubic hair with her fingers before entering the teen's tight pussy with her tongue. Emma squealed with delight as Jessie brought her to multiple orgasms with her tongue and fingers.
As if watching the two hot girls enjoying lesbian sex wasn't enough a surprise, Luke was dumbstruck when Tony drew the naked 13-year-old boy close to him and began fondling his penis and balls. Luke had never thought he had any gay tendencies, but he enjoyed the feel of Tony's strong hands and muscular body.
Tony positioned Luke's naked body on his lap. The boy was a foot shorted than Luke, and he fit easily and comfortably. Luke could feel Tony's hard cock pressing against his firm bottom. Tony then began kissing the boy as he continued to fondle Luke below the waist with one hand, while massaging his chest and boy nipples with the other.
The fondling turned into a hand job as Tony vigorously used his fist to bring Luke to a quick orgasm. Tony was dutiful in licking the spunk from his hand and Luke's young, developing body.
Tony laid back as Luke crawled on top to rub his wiry 13-year-old body all over Tony's muscular one. Tony's hands caressed Luke's back and firm butt. Tony poked at Luke's anus, which caused Luke to jump.
Eventually reaching Tony's penis, Luke played with it before putting it into his mouth. Luke used some of the same techniques that Jessie had just used on him. Emboldened, Luke fondled Tony's mature balls before Tony came with a powerful orgasm which dripped from Luke's mouth. Tony wiped away some of the cum, and open-mouthed kissed they boy in appreciation as both partners reloaded their love juices.
Nearby on the bed, Jessie had positioned her blonde, 14-year-old lover so that they were in the 69 position, with the leaner teen on top. Emma gleefully ate at Jessie's pussy. With Jessie's commanding position, she was able to poke, lick and prod Emma's young pussy and anus. Emma's long legs twitched uncontrollably as Jessie stuck her tongue deeply into Emma's asshole. It was certainly a night of firsts for the young teen.
Tony moved towards Emma, and she used her free hand to fondle Tony's package while never taking her mouth off of Jessie's pussy.
Luke became jealous that Tony's attentions were going elsewhere. He stood up on the bed and rubbed his naked body and penis up and down on Tony's back, which caused Tony to laugh. He reached over and flipped the naked boy onto the bed.
Tony carried the naked 13-year-old boy off of the bed and bent him over a nearby chair. Reaching for a jar of lube, he began coating Luke's bi-curious anus. This seemed to snap Emma out of her lesbian euphoria, and she snapped to Tony, "Don't hurt my little brother."
Tony speared Luke's butthole with his penis. It clearly caused Luke some pain. Tony assured the boy that he would go slowly. Tony told Luke to relax his sphincter muscled, and he distracted the boy by reaching over to play with Luke's erect penis.
Tony penetrated again, and Luke took it like a little man. Tony went deeper and faster with his 8" cock before eventually coming inside Luke's virgin ass.
Luke was sore as he approached the bed. Jessie and Emma inspected Luke's bunghole. It was wide open almost to the size of a 25-cent piece. Jessie assured him that it would close soon as she and Tony had played the same games with each other many times.
The two naked siblings hugged each other. Emma pressed her breasts against Luke's chest sympathetically. In no time Luke was erect. As a present for his bravery with Tony, Emma gave Luke a combination hand job and blow job.
Tony started to get dressed, explaining that his shift as the doorman would start at 6:30 in the morning. Tony adjusted his package as he positioned it in his tight bikini briefs. Emma politely thanked him for the lovely evening.
As Tony left, Jessie extended her hands to the young teens and said, "I love my kids." Luke and Emma snuggled their naked bodies against Jessie's, and together they suckled her large tits. Luke's wandering hands alternated between fingering both girl's pussies.
The End.
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