Lonely Rich Girl

By Titan Hoop Club

Published on Mar 11, 2022

Lesbian

This is the third, and final installment of the series. The work is completely fictional, and involves the cast of the Disney Channel TV show, "Jessie." If you are offended by older and younger lesbian sexual pairings, please read no further.

(Lesbian Celebrity)

Morgan Ross was less than delighted when, with the support of his wife, his beautiful blonde, 14-year-old princess of a daughter announced that she was a lesbian, and planned to begin a relationship with a 17-year-old fashion model.

Being a good NYC liberal, Morgan proclaimed his acceptance and encouragement, society told him he must do. He wondered if the young pair were already having sex? "Well, at least Emma won't get knocked up," Morgan rationalized.

Emma's younger siblings, Ravi and Suri merely shrugged their shoulders at the news. Younger brother, Luke, thought that the whole thing was extremely "hot," particularly when Emma shared a picture of the young, tan model from an issue of Teen Vogue. Luke swiped the magazine from Emma's room and beat-off to Caitland's picture that night.

Rather than going on innocent dates to the movies, and such, Emma would usually hook up with Caitland at an apartment that she shared with several other young, aspiring models. The sex was always heated between the tall, slender-bodied teens.

Unfortunately, the romance was not to last long as Caitland's model agency transferred her to Milan where her dark features and green eyes might prove to be marketable.

Emma was heartbroken and cried real tears as she rested her head on her nanny, Jessie's, ample bosom.

After being surprised and "ratted out" to her mother by her pretty, school-rival, Bryn Breitbart, at the lesbian "Deuces Club," the two girls had reached an understanding. Emma hadn't asked her mother why she was fucking her 14-year-old classmate, and Christina, Emma's mother hadn't asked Emma why she was fucking her 20-year-old nanny.

Emma was now open about her sexual preference at school, while Bryn chose to remain in the closet for now, fearing the reaction of her nouveau riche parents. Both wished to continue to participate in further "Deuce's Club" events.

Christina Ross, while still needing to be discreet with her lesbian encounters, was somehow relieved that her biological daughter now knew the truth. At least with Emma, she no longer needed to hide her sexual trysts with Jessie, and other women and young girls, including Bryn.

Morgan knew of Christina's lesbian needs and desires, and they both chose to look in the other direction as the married couple indulged their sexual lives with others. Hollywood gossip alleged that powerful movie producer, Morgan, was seeing Scarlett Johansson on the side.

Christina, who had started to remain in NYC for longer periods of time now, was particularly disappointed that the previously planned "Deuce's Club" event had to be cancelled the previous month while its founder, Sonja Hammersmith recovered from a nose job.

The good news was that the new event was definitely a "go" in two Sunday's. Christina, Jessie, Emma, and Bryn were all looking forward to attending, and had made appointments to be waxed, and to have their hair and nails done prior to that day.

Jessie was just happy that she had been able to retain her job, even if she felt underpaid. She had had sex with Emma, Christina, and even Bryn! She had been caught, but Christina had been understanding, considering her own peccadillos.

Jessie was currently on a diet and was jogging in Central Park. She wanted to lose 8 pounds in the two weeks before the event.

As usual, Morgan was in California working on one of his motion picture productions. Bertram was left to look after the younger Ross children that afternoon as Christina announced that she was going to be taking Emma and Jessie on a "spa day." Technically, she wasn't fibbing, as the "Deuce's Club" took place in the Sapphire Spa in Greenwich Village.

The Ross limousine stopped to pick up Bryn. She had been included in the spa ruse, and her parents, who knew that Bryn had a reputation as a snobby bitch, were happy that she seemed to be making friends with the pretty and nice, Ross girl.

Bryn's lustrous red hair shimmered in the natural light as her doorman opened the door to the limo. Bryn was immaculately outfitted in a white minidress ensemble which showed off her long, lean legs.

As the limousine made the short drive to the Greenwich Village spa, each girl and woman was consumed by her own thoughts:

Christina had had her day cut very awkwardly short the last time she attended the "Deuce's Club." She had just started eating Bryn's delicious young pussy when she had been alerted of Emma's and Jessie's presence. The rest of the afternoon had been kind of a blur as she dealt with her young daughter.

Bryn had also had her afternoon cut short. She wanted to do a lot more than she was able to with Christina, including rubbing her face in the former-model's magnificent tits. She had managed to get a good eating out from Jessie, and had fondled and licked her big tits, which, truth be told, were even bigger and better than Christine's. However, Bryn was anxious to explore the other areas of the club which she had been unable to visit, and to perhaps meet some new people. Bryn had an affinity for older women.

Emma had made a girlfriend in Caitland, and was anxious to meet other girls of a similar age. Although she had convinced herself not to be afraid of hooking up with the more experienced lesbian women.

Jessie was almost panting with excitement. She was ready to fuck everything and everyone! She had particularly enjoyed being ravished by three women at the same time as she stood in the alcove. If only Emma could have waited twenty more minutes before stopping by. Jessie promised herself that there would be no interruptions or drama on this visit.

Christina had given Jessie the lowdown on Sonja and the "Deuce's Club." Sonja was a very successful owner of an agency that handled models and actresses for commercials, print work, and even movies and TV. Morgan and Christina had used the agency many times for their various projects, and Sonja and Christina had become very good friends, but not lovers. Both women had a preference for younger girls.

With Sonja's access to so many pretty women and girls, she could easily fill the "Deuces Club." Access was a reward for her female business associates, like Christina. However, each guest had to bring a pretty girl with them as the price of admission. Sonja had paid a large bribe to the NYPD to ensure that there would be no problems with entertaining underage girls, like Bryn and Emma.

As the quartet exited the limo, it looked like a normal spa day even to the driver. He did find it a little odd that there was a line of limousines waiting to disembark passengers. All of the women getting out seemed to be especially attractive.

The same two women were at the Spa's front desk when Christina and Jessie signed in. One was a pretty brunette in her mid-twenties. She was now dressed in a sort of toga miniskirt. Two white straps crossed her beautiful naked breasts. The other was an armed, burly short-haired dyke who was there to make sure that no riff-raff, photographers, or uninvited guests tried to gain entry. Emma and Bryn felt like they were being mentally undressed by the butch guard, and quickly made their way to the changing room.

By now, all four knew the rules. They carefully changed out their clothing and hung them so they wouldn't wrinkle. Accepting four togas from the changing room matron, they felt that their nude bodies were being appraised in the crowded room.

Christina, in her usual matronly way, began to counsel the three younger girls that there were no rules today, and there should be no judgement on who does what with whom. Jessie was amused by receiving such motherly advice with Christina's naked boobs almost in her face.

Christina also suggested that all take a deep, cleansing breath as they prepared to exit the changing room, and for all intents and purposes, to enter the orgy!

Jessie was proud that she was was able to lose her 8 pounds in only two weeks. She felt fit and lean and was proud to show off her body. "Screw it," she said as she whipped off her toga. Bryn chuckled and took her toga off too. Jessie put her arm around the naked teen as they walked out of the changing room and surveyed the scene. There seemed to be more naked bodies intertwined than during their previous visit. The club must have grown? Jessie surmised.

Suddenly, Bryn stopped and said, "I hope you don't mind?" to Jessie. She pressed her lithe naked body against Jessie's back and reached around to fondle Jessie's large breasts. "You have the best boobs ever," Bryn whispered into Jessie's ear. With their similar red hair, it appeared to gawkers that one of the sisters was feeling the other one up.

Jessie suggested that they each go their separate ways in search of meeting new friends.

Sonja was in her usual spot of importance. She was sitting in a plush chair in an elevated position that gave her a commanding view of the room. Sonja had three of her well-manicured fingers up the pussy of a pretty brunette of about 16. After hearing Christine's story, Jessie assumed that the girl was one of Sonja's eager clients.

Sonja shouted to Jessie, "I want to visit with you later, Jessie." Jessie smiled and waved at her hostess, and just for fun shook her big boobs at Sonja, which caused her to smile and dramatically lick her lips. Sonja one was one of the three women that were mauling Jessie at the prior event, but Jessie was interrupted by Emma. Jessie swore to herself that there would be no interruptions that day.

Jessie continued her tour of the facility, looking for an enticing stopping place.

Christina and Emma walked out of the changing room together. They were both wearing their little toga's which exposed one naked boob. Emma was considerably less self-conscious than during her first visit to the "Deuce's Club." Now sure of her lesbian preference, Emma was hoping to meet a beautiful girl or two that day.

With her sexuality now in the open and her mother along, Emma hoped that Christina would hook up with a nice woman her own age. However, that's not what Christina was looking for today. She hadn't killed herself to stay in shape in order to hook up with another MILF, Christina was hoping to dip her tongue into the pool of pretty young models and actresses that Sonja had promised.

As Emma was walking near the pool area, she noticed an extremely familiar face having sex with a well put-together woman in her forties, and a very young girl. It was Miley Cyrus! Emma stopped to watch.

Miley was two years removed from her hit TV show, "Hannah Montana." Her solo records were continuing to sell well, and her tour stops were selling out all over the world. Miley had made a reputation for herself in Hollywood as a very enthusiastic and unashamed lesbian. She was currently in New York doing overdubs for her new album when she was invited to the "Deuce's Club" by her agent.

Miley was sitting in a chair. The woman licking her pussy was, in fact, her business agent. She had invited Miley to be her guest at the club, promising lots of available young girls. The naked, flat-chested 12-year-old girl fondling Miley's breasts was Mindy. Mindy and Emma had engaged in a threesome with a pretty, 17-year-old fashion model some months prior.

Seeing the pretty 14-year-old in the toga, Miley, in her trademark horse voice, yelled, "Hey, Blondie!" Miley motioned for the pretty teen to join her. Emma was unable to hear what Miley said to her two companions, but they quickly dispersed.

Emma approached the worldwide celebrity, who was now 20-years-old. Emma had been a big fan of the "Hannah Montana" TV show, and had purchased most of her music. She was excited to meet Miley, and it didn't matter to her that Miley was naked and probably wanted to fuck her.

Emma was still wearing her toga as she walked up to Miley. Her small breast protruded from one side of the toga, a little pink nipple was now erect.

Miley clapped the top of her thighs as an invitation for the beautiful teen to sit down on her lap. Emma happily complied, and Miley put her hand around Emma's tiny waist.

Emma began babbling about what a big fan she was of the young superstar, and the souvenirs she owned, and what the music meant to her, blah blah blah. Miley had heard it a million times and was only "pretend listening." Miley had found through her vast carnal experience that if a pretty fan wanted to express her devotion, it only made it easier to get into her pussy later.

Miley was bisexual, or "polysexual," whatever the difference supposedly was. She tended to be more promiscuous with females, and wasn't particularly picky about their ages. Miley was a very sexual being, and simply enjoyed having sex with new people. Emma was the current girl on her radar, or "gaydar."

As Emma continued to gush about the young star, Miley's hand was making its way up Emma's toga and tickling her upper thighs.

Removing her left hand from Emma's waist, Miley began to stroke Emma's golden tresses. "Ya'll are such a pretty girl," Miley said to Emma. "I'd like to take you on tour with me." That was Miley's usual closing line that she used to seduce young female fans. Since Emma was already half-naked and sitting on Miley's lap, the 20-year-old superstar decided to "close" the deal early.

"Oh, wow!" Emma said, "That would be awesome!" With Emma now a sure thing, Miley began to suck and nibble on Emma's exposed breast, while at the same time entering Emma's pussy with a single probing finger which Miley rapidly inserted in and out, bringing Emma to a quick orgasm.

"Raise your hands," Miley instructed Emma. In a flash Emma's toga was raised over her head and discarded on the floor. Still on Miley's lap, the singer began to fondle Emma's breasts with both hands. Emma leaned in to kiss Miley. Miley's active tongue seemed to engulf Emma's entire face with saliva.

Emma was placed on a nearby pile of pillows. Miley opened Emma's long, lean, legs and began to hump her nearly hairless crotch with the full force of Miley's lean, muscular body. Emma reached for Miley's well-photographed ass, and held on for dear life as the slapping sounds of their bodies could be heard some distance away.

When satisfied, Miley put her experienced tongue to work, lapping and spearing Emma's young vagina. Emma came quickly, her legs spasmodically quivering as she orgasmed.

Flipping the 14-year-old over, Miley stuck her face between Emma's pretty butt cheeks and began to lustily alternate between licking Emma's young pussy and anus. Emma's legs flailed as she engaged in a real-life fantasy with the young superstar.

Christina Ross was relaxing on a chaise lounge near the pool, and was admiring the parade of young, naked bodies as she enjoyed a glass of club soda. Suddenly a pair of hands latched on to her boobs from behind. A young voice was heard, "I like big boobs." It was the precocious 12-year-old, Mindy. Christina replied, "And I like you."

Christina extended her had so that the preteen could join her on the chaise lounge. Christina sat up to make room for the slight girl. Mindy was perhaps 5'2" and slender. Her dark hair was in a cute, pixie cut, and had already been mussed up by other girls, including Miley Cyrus. Completely naked, Mindy had a light tan. Her raised nipples were the only hint of the female breasts yet to form, and her little slit was hairless.

Mindy was open to just about anything, and was a popular member for several of the older women of the club, including Christina, who had a preference for just-budding teen girls.

Christina opened her legs for Mindy to sit in between them. With her left hand, Christina began pinching and stretching Mindy's erect nipples. With her right hand, Christina began probing Mindy's tight, adolescent pussy, gently stroking in and out with a well-manicured finger. Mindy's little legs spasmed with delight.

Pushing Christina down on the chaise lounge, Mindy climbed on top of Christina with her lithe, 90-lb. body before coming to a halt on Christina's chest. Mindy's mouth and hands alternated between Christina's firm breasts as the pre-teen happily giggled. Christina grabbed Mindy's tiny ass firmly, and inserted her fingers in deeply into Mindy's tight ass and vagina to her squealing, leg-kicking pleasure.

Christina rolled the 12-year-old over, and repositioned herself until they were in the 69 position. Each happily lapped at the others pussy until both had orgasmed.

"Yes, indeed," Christina thought. "There's nothing like a young girl."

Bryn was receiving a professional massage, one of the services provided that day, when she was approached by an attractive blonde-haired woman in her 40's. Bryn was facing up, and her pussy was covered by a towel as the professional masseuse was massaging her legs and thighs.

Seeing Bryn's pretty face, red hair and slender body, the older woman inquired as to whether Bryn was an actress or model? "Neither," replied Bryn, "Although I have often been told that I should be," Bryn replied without a hint of humility.

Bryn was oily from head-to-toe from the massage, yet the woman extended her hand to the young teen, and said. "My name is Sheila Morgenstern, I represent Miley Cyrus and several other young clients. She's here somewhere." The news definitely interested Bryn, who wanted to look for Miley later.

Sheila continued, "With your red hair and pretty features, you could fill a missing niche in the industry." Sheila was just blathering to get the pretty 14-year-old's attention. It was working. She was reeling Bryn in, hook-line-and sinker.

Sheila asked Bryn her age, what school she went to, if she'd ever acted in any school plays or done any public speaking? Meanwhile, "to be useful," as she explained to Bryn, Sheila had oiled up her hands and began innocently massaging Bryn's mid-section. As the conversation continued, and Bryn began to imagine herself as the next teen multi-media star, Bryn hadn't noticed that Sheila's hands were now massaging her young breasts, and the look on Sheila's face had gone from friendly interest to one of predatory sexual lust.

When the masseuse announced that the massage was over, Sheila held up her oily hands and pointed to other parts of her naked body where the oil had gotten on to. As Bryn rose from the massage table, Sheila suggested that they shower off the oil so that they could continue talking about Bryn's future career.

Bryn was surprised that Sheila had followed her into a shower stall, and had begun soaping the teen up before she could ask any questions or protest. Sheila's hands quickly worked her way all over Bryn's lean, young body. Sheila paid extra attention to Bryn's red pubic hair and small breasts, while cooing, "You're going to be a big star," to the gullible 14-year-old.

Sheila pressed her soapy body against Bryn's and began to kiss her. Bryn made a couple of futile attempts to resist, but Sheila was stronger and determined. Sheila's hand was less-than-gently placed between Bryn's legs and Sheila aggressively began to rub Bryn's pussy as her larger breasts pressed against Bryn's tightly.

Whether she meant to or not, Bryn began to submit to Sheila's touch. Recognizing the signs, Sheila got on her knees to lick Bryn's pussy to orgasm.

Exiting the shower, Sheila grabbed a handful of Bryn's firm ass and promised to "Be in touch." Sheila left the shower room in search of fresh, young, prey. Bryn exited in search of Miley Cyrus.

Sonja had promised herself that she would have another opportunity with red-haired Jessie and her big boobs. Accompanied by two of her pretty, 18-year-old clients, Sonja caught up with the 20-year-old nanny, and the trio escorted Jessie to a nearby massage table where she was placed on her back.

Sonja and one of her girls began licking and fondling Jessie's large breasts, while a pretty blonde positioned herself between Jessie's legs and licked eagerly at Jessie's bald pussy. Each woman would change positions as Jessie was brought to several orgasms.

Returning the favor, Jessie insisted that Sonja take her place on the table while her girls kissed and fondled her and Jessie ate her pussy. It was the least that Jessie could do for Sonja, who had invited her to the "Deuce's Club."

Bryn finally found Miley. But wouldn't you know it, she was busily fucking Emma! Well, Bryn was certainly not going to walk away. After her fling with Sheila just some minutes prior, Bryn assumed that she would be working with Miley very soon anyway.

Emma was straddling Miley's face when she was approached by her pretty, redhaired classmate. Bryn pinched one of Emma's nipples and declared, "Lucky Emma," as she looked down at the naked superstar, her tongue licking her blonde rivals' pussy.

Between moans, Emma politely introduced her classmate, "This is Bryn." Seeing another lean, beautiful, naked 14-year-old, Miley was only too happy to invite Bryn to join her and Emma. "My pussy won't lick itself," Miley crudely put it to Bryn, who laid down and complied, knowing that Emma's tongue had probably been there only moments before.

Experienced and voracious Miley worked the two girls to sexual exhaustion, as the trio licked and fingered every orifice on each of their their young bodies.

The two rivals, Bryn and Emma, had enjoyed having sex with one another, as well as with Miley. They walked hand in hand to the changing room. As they were leaving, they noticed 12-year-old Mindy. She was on the shoulders of the burly, bull dyke security guard, who was eating her bald, preteen pussy, much to Mindy's apparent delight.

As Miley entered her limousine to leave, she said to Sheila, her agent, that this was one of the most fun times that she had ever had, and that none of the girls that she had fucked that day were crazy like some of her young, female fans.

Sheila agreed that the day had been fun, and was thankful to Sonja for inviting her. She would long remember having sex with a 14-year-old redhead particularly fondly. "Now, what was her name?" Sheila asked herself. "Oh, it doesn't matter."

End of the "Jessie" lesbian trilogy.

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