LONELY RICH GIRL 5
This is the fifth installment of the series. The work is completely fictional, and involves characters from the Disney Channel TV show, "Jessie." If you are offended by older and younger lesbian sexual pairings, please read no further.
(Lesbian Celebrity)
Blonde, beautiful, Christina Ross looked deeply into a large vanity mirror and carefully examined her face for any new age lines. The former model had recently turned 43, and was becoming increasingly concerned about her looks, and getting older.
A mother of four, with her oldest child being 15, Christina was the CEO of several successful businesses, and was beginning to feel the pressures surrounding her.
Although she and her husband, Ross, shared a large, magnificent penthouse apartment overlooking Central Park, Christina was currently holed away in an upper-floor suite in New York City's iconic Plaza Hotel, after lying to her family that she was headed to Boston for a short business trip.
Still sitting in front of the tell-all mirror, Christina continued to apply her makeup, and fluff her meticulously-coiffed blonde hair.
Minutes later, Christina picked up her bejeweled cellphone and punched in the name of a familiar contact. "Room 1542" was all that Christina texted.
Beautiful, 15-year-old redhead, Bryn Breitbart had received the text. The aspiring teen model then clicked her phone off upon receiving the brief message.
The pretty girl's parents were in the midst of a very contentious separation. Both of them seemed more concerned about jockeying for position in the divorce proceedings, than they were about Bryn's welfare or where she seemed to mysteriously go off to at times.
Recently, Bryn had agreed to a lesbian tryst with Sonya Hammersmith, a well-known NYC socialite. Among her several businesses, Sonya ran a top agency for models and actresses. With the promise of adding the pretty, 5'8" teen to her stable, Bryn had given Sonya her slender, youthful body in exchange.
As the taxi cab brought Bryn to the nearby Plaza Hotel, Bryn paid the driver in cash, so as not to leave a credit card trail. With large sunglasses on her face, Bryn was sexily dressed in a designer minidress which amplified her youthful beauty, and her long, shapely legs.
Bryn and Christina had secretly been lesbian lovers since Bryn had turned 14. A school mate of her daughter, Emma, Bryn had been easily seduced by the famous Christina Ross. Along with her husband, Christina was a movie producer, among the many hats that she wore. The attractive older woman had dangled that carrot in the young teenager's greedily-ambitious face before luring Bryn into her bed, like Christina had done with so many other women and girls.
To Christina, like Sonya, engaging in sex with underage girls was a sort of powerful elixir, serving as a temporary fountain of youth for the aging women. Power and money, as always, served as the necessary aphrodisiacs for the starry-eyed young girls.
Unknown to Christina, her then-13-year-old daughter, Emma, had begun willingly giving herself to her beautiful, big-breasted, 18-year-old nanny, Jessie Prescott. In an odd triangle, Christina and Jesse were also secret lovers.
It nearly all came crashing down the year before at the Deuce's Club, a monthly lesbian sex party held at an upscale Manhattan spa. The hostess of the gathering was always more than happy to include pretty teenage girls as guests of their wealthy female clientele. Sonya regularly paid the NYPD a hefty bribe to ensure that the Deuce's Club patrons were not disturbed.
Pretty, young Emma, and her redhaired nanny were welcomed to the monthly lesbian event, where any woman or girl could have sex with any other willing woman or girl. No one referred to it as an orgy, which is what it was.
While Emma was being enthusiastically eaten out by Jessie, they were, to their horror, discovered by Bryn, who unknown to Jessie and Emma, was the secret guest of Emma's mother, Christina.
After some very uncomfortable moments, the four realized that they all possessed a secret that could destroy one another, and so they had come to an understanding. While not disclosing the details of their intimate relationships, especially with older women, Emma and Bryn came out openly as lesbians to their high school peers and to their parents. Emma, for a time, dated a similarly-aged young model who had appeared in Teen Vogue.
Except for the mother-daughter combination of Emma and Christina, all four continued to discreetly have sex with each another. Emma had even accompanied Bryn to Sonya's apartment, and likewise had lesbian sex with the older businesswoman, as well as her guest, a well-known French fashion photographer.
Bryn checked her makeup in the elevator as she rode up to the 15th floor. In addition to the masterful cunnilingus that Christina Ross always provided, Bryn felt safe and loved in Christina's gentle arms. Bryn and Emma were friends now, and Bryn would be careful not tweak Emma's nose by revealing that she had recently been fucked by the pretty blonde's mother in yet another New York hotel suite.
Before the beautiful, teenage redhead arrived, Christina had changed outfits. Opening the hotel room door for Bryn, Christina was elegantly dressed in a floor-length black silk robe. Christina's blonde, shoulder length hair provided an interesting contrast to the dark color of the fabric.
Closing the hotel room door, Christina greeted Emma's classmate with a passionate, open-mouthed kiss. Christina's eager hands caressed Bryn's flowing red hair, and stroked the 15-year-old's slender back. It was as if Christina was receiving a transfusion of Bryn's youth by holding the teenager tightly in her eager arms.
Opening her robe, Christina revealed her C-cup breasts to Bryn, who smiled back in appreciation as the teenager gently caressed Christina's still-firm, adult boobs.
Even at 43, Christina was still an extremely attractive woman. Having sex with Bryn, and other young girls, gave Christina the affirmation as a desirable woman that she so desperately needed. Alternately, Bryn felt that having sex with Christina gave her the attention and affection that she wasn't receiving from her emotionally-absent parents.
The slender, 5'8" redhead bent down, and began to gently kiss and suckle Christina's big breasts, and eagerly fondled them. Bryn preferred large, full breasts. If her own small, 32-B-cup breasts didn't grow soon, Bryn was determined to get implants.
Christina was now only wearing black panties and stiletto heels as she turned the teenager around and began to unzip Bryn's slinky, designer minidress. Moments later, Bryn was nude, and prepared for whatever Christina Ross had in store for her.
The older woman fastened a strap-on over her silky panties. Bryn looked on in anticipation. The 15-year-old aspiring model particularly enjoyed being fucked by the big dildo.
Christina laid next to the pretty teen and began seductively stroking the rubber phallus. Temporarily releasing the flesh-colored dildo from her firm grip, Christina began to tongue-kiss the high school sophomore, and to avidly fondle the teenager's modest, slightly freckled breasts.
Bryn giggled in anticipation when Emma's mother flipped the redheaded teen onto her stomach. "Why don't you get on all fours?" Christina suggested.
Raising her long, slender body atop the bed, Bryn's B-cup breasts pointed attractively downwards toward the mattress.
Getting into position behind Bryn, Christina cupped one of Bryn's youthful breasts and gave it a playful squeeze.
Gripping both sides of Bryn's slender waist, the insatiable 43-year-old lesbian plunged the strap-on dildo forcefully into Bryn's anus. The 15-year-old gasped, but not out of surprise. The teenager had been fucked in this manner many, many times before by Christina, and it had gotten to the point where she now even requested anal sex from the older woman.
Continuing from the doggystyle position, Bryn's lithe body rocked from the vigorous anal pounding provided by Christina. Bryn gritted her teeth and moaned with undisguised pleasure after each of Christina's aggressive thrusts.
The pair would make lesbian love for the better part of the afternoon. While Christina was clearly enamored with Bryn, her thoughts would sometimes drift to the promise of other young actresses and models at the Deuce's Club lesbian parties. Christina regretted that she would be unable to attend the next Deuce's Club gathering, as she would have to be in Los Angeles at the time.
It was precisely 1:12 in the morning. Surveying the empty hallway, and hearing the Ross' butler, Bertram, noisily snoring, Emma tiptoed to Jessie's bedroom. As usual, her famous parents were out of town.
Waiting patiently for the gorgeous 15-year-old was her 20-year-old nanny and secret lover, Jessie Prescott. Jessie greeted the slender, long-legged teenager with a yearning, tongue-kiss.
Emma was wearing an adorable, age-appropriate, pink pajama outfit, complete with matching shorts. Jessie then began to unbutton the teenager's pajama top, revealing Emma's pointy, A-cup boobs, which Jessie greedily encapsulated in her impatient hands.
In between kissing and fondling the beautiful, blonde teen, Jesse almost casually remarked, "Darla's in town with the airline. I was thinking we could take her with us to the Deuce's Club on Saturday."
The suggestion surprised Emma. "I thought you kind of hated Darla?" 15-year-old Emma asked before Jessie's mouth descended upon her little boobs, and her pink, Hershey Kiss-sized nipples. Darla was Jessie's former "frenemy," and worked for a cut-rate airline as a flight attendant. Darla had managed to arrange for a three-day layover in New York City.
"Aw, she's O.K.," Jessie said about Darla, temporarily releasing one of Emma's erect nipples from her teeth. Jessie and Darla had agreed to an uneasy truce when their military parents had married the prior year. The attractive 20-year-olds had once been great friends at the Texas Army base where their parents were stationed. As 8th graders, they had even engaged in a sexually curious, girl-girl make out session behind a row of tanks.
Darla had freaked out when Jessie went for Darla's tiny, junior high school breasts with her hand, and from that point forward, the dark-haired girl had made it her mission to make Jessie's life a living hell. Darla succeeded. Jessie's high school years were miserable, and as soon as she graduated at age 18, Jessie had moved to New York in search of fame and fortune as an actress.
Although living in the home of famous, internationally-known movie producers, Jessie was still very much an aspring actress. Actually, she was really just the nanny to four rambunctious children, one of whom secretly enjoyed having lesbian sex with the D-cupped redhead.
To impress Darla, Jessie had used the Ross' connections to have Darla "comped" into the famous Waldorf Astoria Hotel. Truthfully, Jessie didn't really want to see Darla, but she wanted to take the opportunity to gloat about the connections that she had used to put her "frenemy" up in the luxury hotel.
Although Jessie and Darla had indeed agreed to a truce following the wedding of Jessie's dad to Darla's mother, Jessie was nevertheless wary, and thought it best to call Darla on the phone, and see how things were going?
"How do you like your room?" Jessie asked. Rarely willing to give an inch to Jessie, Darla said, "It's O.K. I guess you weren't able to get a suite?" As their bickering became more heated, the memory of their brief girl-girl encounter was bitchily raised again by Darla.
The Ross kids had accompanied Jessie to Texas, and Darla had quickly become enamored with Emma. While only 14, the blonde-haired girl was already a long-legged beauty. While envying Jessie's big boobs, Darla had also on many occasions since, imagined her face buried between Emma's slender legs.
Suddenly, Darla blurted out: "Since you're a lezzie, have you managed to fuck that cute little Emma Ross yet?" There was a prolonged silence over the phone as Jessie thought of how and what to say.
"OMG!" Darla squealed, "You have fucked her! Truthfully, I can't blame you. She's a hot little piece of ass." Darla had finally revealed her true sexual preference, which led to the most honest conversation the two Texas girls had ever had. Darla had even admitted that she had never "done it" with a girl, but was anxious to try. Jessie immediately thought of the Deuce's Club.
Raising her lascivious mouth from Emma's pointy boobs, which were now wet from saliva, Jessie again asked the 15-year-old about including Darla at the Deuce's Club.
Emma well-remembered Darla from the previous year. Expecting to meet a dragon-lady, the then-14-year-old was surprised at how sexy Jessie's "frenemy" actually was. Emma thought of how her relationship with Bryn had improved over the past year, despite the fact that Bryn was regularly fucking not only Emma's mother, but Emma and Jessie as well. Emma believed that Jessie's and Darla's association could also be improved by girl-girl sex.
"I guess it would be O.K.," Emma finally said. "She is pretty hot." Jessie was surprised by Emma's last remark, knowing that Darla had expressed more than a passing desire to fuck the pretty, 15-year-old, when told about the Deuce's Club. "That's up to Emma," Jessie had said.
With that bit of conversation now over, Emma lifted Jessie's undershirt upwards toward her neck. With one hand squeezing one of Jessie's big boob, Emma attempted to suck the other large breast whole.
Emma was tasked with calling Sonya to find out if Darla would be welcomed. By definition, the Deuce's Club meant two. Each invited guest, usually an older, wealthy woman, was required to bring a pretty girl with her. With a seemingly endless supply of out-of-work, or underemployed young models and actresses available in New York, fresh, new girls seemed to magically appear at each of the eagerly-awaited monthly events.
After Emma vouched for Darla's attractiveness, and that the Texas flight attendant was only 20-years-old, Sonya said, "Sure. Bring her along. There can't be enough pretty girls."
Hanging up the phone, Sonya thought back to the slender, naked bodies of Emma and her redhaired friend, Bryn. Fucking the gorgeous, cooperative, 15-year-olds had thus far been the highlight of her year. Further, she had been able to offer the two willing young girls to her butch houseguest, who was a famous French fashion photographer. Sonya raised her skirt, and inserted her hand beneath her panties as she thought of the two naked teenagers.
Rather than using the Ross limousine, and potentially raising some uncomfortable questions, Jessie and Emma picked up Darla at the Waldorf Astoria in a yellow cab. Jessie had carefully explained the club protocol to Darla.
The slender, dark-haired flight attendant sat in the back of the cab with Darla and Jessie at each door, and Emma sitting in the middle. Emma greeted Darla with a friendly, European kiss on the cheek. Darla responded by suggestively placing her hand on Emma's smooth upper thigh.
The dress code at the Deuce's Club had recently been revised. Before, women were required to wear a toga-style garment, or to walk around wearing nothing at all. The toga was designed to enticingly expose one breast, and was still somewhat favored by younger girls with perky breasts.
Recently, Sonya allowed members and their guests to wear their own bathing suits, if they so desired.
Jessie and Emma chose to go from the locker room into the main areas of the spa dressed solely in their bikini bottoms. Jessie's plump, D-cup boobs, and Emma's petite, pointy breasts drew a lot of hungry looks as they excitedly scoped out the lesbian party guests.
Trailing behind, Darla was dressed in a more conservative one-piece navy blue swimsuit, similar to what a college swimmer or diver might wear. The first-time visitor to the Deuce's Club couldn't believe what she was seeing. There were naked, and semi-naked women and teenage girls throughout the large spa. Some were laying their groundwork of seduction, while others were openly and actively engaged in lesbian sex, sometimes in small groups.
Seeing the new, dark-haired girl, an attractive, well-to-do, middle-aged woman approached Darla, and placed her hand around the 20-year-old's slender, bathing suit-clad waist. "Hi, my name is Madeline. What's yours?" Darla froze at the unexpected touch of the mature stranger, but managed to nervously sputter, "D-D-Darla."
The woman then began to seductively rub Darla's flat stomach. "That's a pretty name for a very pretty girl," the 40-ish woman cooed. She was wearing a toga, and one large, surgically-enhanced breast was pointing enticingly outward.
Not taking her hand off of Darla, the woman remembered that many of the pretty, younger girls were aspiring actresses and models, lured by the wealthy, influential members of the Deuce's Club with promises of work in their field, or a straight cash payment.
Madeline's hand traveled up from Darla's stomach and landed on a modest, B-cup breast and gave a gentle squeeze to test Darla's reaction. "You must be a model," the woman said. "What have I seen you in?" Darla was flattered that the woman thought that she was a model, and didn't remove the middle-aged woman's presumptuous hand from her B-cup breast.
"Actually, I'm a flight attendant," Darla said proudly. Frankly, Madeline didn't give a flying fuck about the pretty, dark-haired girl's occupation. Her singular goal was to lure the Texas beauty to a quiet corner that she had preselected, and to lick Darla's sweet, young pussy.
"Why don't we go somewhere quiet to talk?" Madeline suggested. She had noticed that Darla was having a hard time taking her eyes off of the older woman's bountiful, man-made boobs. Madeline placed Darla's curious hand atop her naked, surgically-enhanced breast, and held it there.
Hesitantly accepting the woman's hand, Darla let Madeline lead her to a distant part of the many-roomed building. Darla's attractive butt-cheeks jiggled in her one-piece swimsuit as she nervously walked with the attractive, and very interested, stranger.
Looking back over her shoulder, Darla could no longer see Jessie nor Emma in the large main room.
Sonya was the first to spot Emma. Approaching the long-legged, topless 15-year-old, Sonya said, "Emma, I'm delighted to see you." Sonya's presumptive hands immediately latched onto the high school girl's pointy, A-cup boobs, and began to fondle them avidly, which was making Emma uncomfortable.
Pointing to a nearby chaise lounge, Sonya suggested, "Darling, why don't we renew our acquaintance." Emma had reluctantly, but ultimately willingly, fucked Sonya to help her friend, Bryn, get a modeling contract with Sonya's agency.
Backing up so that the older woman would have to release her juvenile breasts, Emma said, "Maybe later. I just got here." The blonde-haired, 5'8" teen hurriedly walked away.
Jessie had gone exploring, and found herself in the spa's massage room. A tan, pretty girl was rubbing oil on the back of another slender girl who was lying on the massage table. The girl on the table looked up when Jessie entered the room. Jessie did a double-take when she realized that the girl receiving the massage was almost a carbon copy of the girl that was giving her the massage. Clearly, they were sisters. Perhaps, even twins!
"Gia, look at those boobs," the excited girl on the table said to her sister in an accented voice. Both girls were dressed only in thong bottoms. A gorgeous bubble-butt rose prominently from the table. Both raven-haired girls appeared to be under 18, and their young bodies were tan from head-to-toe, with smallish boobs, and brown nipples and areolae.
Hopping off of the massage table, the darkly tan girls were mirror images of each other as they eagerly surrounded Jessie. With their nipples fully-erect, Jessie couldn't decide which sister was hotter?
"I am Gia, and this is Mia." Gia's little boobs were well oiled, and Jessie used that to distinguish between the two teenagers.
"Do you girls know each other?" Jessie jokingly asked with a snort. Mia pressed her little boobs against Jessie's arm, answering, "We are twin sisters from Greece." "I'm Jessie," said the redheaded American with the bountiful, D-cup breasts.
"Your breasts are so beautiful. May I ask if they are natural?" Gia inquired, squeezing one of Jessie's plump mammaries. The smile on Gia's impassioned face as she looked at her twin sister indicated that they were indeed, real.
"Would you like a massage?" Mia breathlessly asked. Jessie had always fantasized about having sex with twins. The closest that she had come to it was a threesome with Bryn and Emma.
"I'd love a massage," Emma said. Four excited hands began squeezing her big, D-cup boobs as she settled onto the massage chair. Jessie's bikini bottoms were swiftly removed. Excited gasps could be heard as her carefully-trimmed reddish pubic hair was revealed.
Now-naked, Gia straddled Jessie's waist, and began to eagerly rub oil into the 20-year-old nanny's big boobs. Mia then began to apply the same sweet-smelling oil to Jessie's feet, legs, and thighs. Working her way up Jessie's fit body, Mia abruptly forced two fingers into Jessie's vagina.
"Unnnhhh," Jessie moaned as the Greek teen model began to avidly finger-fuck her, while Mia's twin sister satiated herself by licking and sucking on the 20-year-old redhead's large breasts.
Mia soon replaced her fingers with her tongue, hungrily boring into Jessie's pussy. Jessie's curvaceous hip began to undulate rapidly due to Mia's oral ministrations. Pulling Gia off of her big boobs, and toward her, Jessie began to sloppily tongue-kiss the younger girl and caress her smooth back.
Jessie's hips began to involuntarily buck as Mia brought the big-busted redhead to an orgasm.
Switching positions, Gia placed her face between Jessie's thick thighs, while Mia straddled Jessie's face as the young nanny enthusiastically ate her out.
For Darla, it had all happened so fast. Lured by Madeline's well-practiced seduction techniques which targeted Darla's insecurities, the dark-haired 20-year-old had found herself lying astride a padded bench, with the naked older woman greedily feasting on her young pussy.
Darla couldn't quite recollect agreeing to remove her bathing suit, but remembered that the amorous woman was quickly on top of her, with a flurry of avaricious hands, tongue, and lips. For Darla, it was an ignominious entry to lesbian sex. She had hoped to get her feet wet at the lesbian party by sucking on Jessie's big tits, or by licking Emma's presumably delicious, blonde, 15-year-old pussy.
Living in Texas, Darla had never dared to even make a date with another girl. Her teenage make out session with Jessie had been as close as she had ever come, and it had frightened her at the time.
With a quick kiss on the lips, Madeline readjusted her toga, and began looking for other young prey. Darla, very much naked, sat up on the bench. Vowing that she wouldn't be fucked and forgotten by the next woman, Darla went in search of her own conquest.
Darla noticed a commotion in a far-off corner of the building. A small group of naked women seemed to engaged with something or someone. It looked almost like a shark feeding-frenzy. Darla, curious, chose to investigate.
Moving closer, Darla was startled to see that it was Emma who was harnessed in a sex swing. The 15-year-old's long, slender legs were bound, and spread wide. Five or six manaical women were simultaneously assailing the blonde-haired teen.
Fearing for Emma's safety, Darla was about to intervene when she saw that the high school sophomore was smiling, and clearly enjoying the experience.
Excited hands were traversing Emma's slender body, while one woman was forcing a large dildo into Emma's pussy, and another was two-fingers deep into the high school sophomore's pink anus. Even Sonya had joined the action. Standing at the head of the sex swing, the older woman was energetically squeezing and kneading Emma's pointy A-cup breasts. Leaning over the pretty teenager, Sonya forced her eager tongue into Emma's mouth.
Still naked, Darla aggressively made her way between Emma's bound, spread legs. Pushing aside the two women who were penetrating the young girl, Darla placed herself at the front of the line and began tongue-fucking the pretty Ross girl's vagina.
"Darla?!" Emma called out in surprise when Jessie's frenemy began to poke, prod, and lick her young, blonde-topped pussy.
As Darla was drilling into the pretty teenager like a West Texas oil well, two hands suddenly gripped her modest, B-cup breasts. Before Darla could react, a naked crotch began to ram into her petite backside. It was Jessie!
"I've wanted to fuck you since you were in 8th grade and had no boobies," Jessie said with snorting laugh. Emma began to laugh as she watched the now-distracted Darla have to react to being dry-humped and fondled in front of a small crowd of other women.
Resuming her position between Emma's legs and licking her young pussy, Jessie kneeled and parted Darla's butt cheeks with her hands, greedily alternating between licking Darla's pussy and anus.
Three exhausted, but satisfied, young women got into yellow cab that early evening. Darla, now sitting in the middle, placed her hands on Jessie's and Emma's pussies. "I hope y'all can take that private jet back to Texas some time," Darla said.
The End of Part 5.
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