Category: Erotic Couplings Stories

Willing Pupil Ch. 01

by Big Jay©

Jake had just passed 40. At 6'3", with dark brown hair and eyes, a taut fit body and chiseled features, he had his pick of the litter of housewives and socialites - if he was so inclined. Jake owned a small chain of day spas in Southern California, as well as a few clothing boutiques. He had majored in physical therapy in college after his football career was cut short with a knee injury. When he opened his first day spa, he found that women who were in the mood to splurge on themselves would not only come in for a massage and a manicure, but also spring for a new dress or shoes to go along with it.

Cleverly, his boutiques were next to the day spas, but the common ownership was never divulged.

Over the last ten years, he had amassed a fair amount of wealth, enabling him to drive a new Porsche 911 every year -- his one indulgence. His divorce from his wife of five years was a casualty of his workaholic lifestyle. With his ex having moved up to LA, Jake had a large house with a pool all to himself in a gated community in the exclusive Laguna Niguel area of Orange County.

The initial separation had thrown him into skirt-chasing mode in his mid-30s. But soon he had grown tired of the same fake-blonde, fake-boobed, fake-lipped, liposuctioned 40-something cougars -- for whom Jake was prime catnip. He gradually settled down and focused primarily on managing his business. Cougars and their daughters were his main clientele, so he maintained the flirtations but kept them on the harmless side the last couple years.

Despite the resistance to temptation he had developed, he nevertheless couldn't help noticing the blossoming young woman who lived next door with her parents.

From a distance, the first thing one noticed about Alexandra, or Allie, was her body. She was petite -- about 5'3", tan and toned from her daily yoga regimen. Her breasts, at 32C, were large for her small 100-pound frame. Dark hair with highlights fell to her shoulderblades. Close up, one would notice her large almond-shaped green eyes - the product of her father's Scotch-Irish ancestry and her mother's Japanese heritage.

Allie graduated from high school and turned 18 the same week in June; she would be starting one of the UC schools the following January.

Although spoiled with material effects, Allie was not a brat. She was mature beyond her years, which would explain her low tolerance for the idiot boys that hit on her at school and at parties and at the mall. She yearned for a real man -- a man who had confidence, who had a plan, who knew what he was doing.

The last few months she would lie on her bed, watching through the blinds in her room as Jake would swim in his lap pool or sunbathe. She would slide her hand into her thong and massage her clitoris with two slender fingers, pull on her pink nipples and imagine running her hands over his Adonis-like body, feeling the strength and power in his arms and chest and ass as he fucked her. And she would cum, holding a pillow over her face to mask her cries of ecstasy. Oh to have a man show her what sex was truly all about! As she lay in the afterglow, she would mutter to herself, "I have got to meet him."

Occasionally Jake, too, would think of his neighbor. Sometimes, when he heard her out at the pool next door, he would go inside, up to his room, and disrobe. His cock, swollen but not yet fully erect, criss-crossed with veins and still sheathed in its foreskin (he was born in Europe), would rise as he ran his eyes over Allie's tight body dressed in her customary chocolate-colored string bikini, taking in her taut ass or her ample chest. He would reach for some lube and drizzle it over his shaft, pull the foreskin back, and stroke. He would imagine how tight she would feel on his rather sizeable cock, how light she would be, how he could manipulate her body so easily, how unsullied, perfect and malleable she was. And he would cum -- spraying rope after rope against his hand, imagining it was her eager, beautiful face he was covering. As he regained strength in his knees, he would look upon her and think "I have got to meet her."

He didn't know her name, and she didn't know his. They'd rarely seen each other outside of their surreptitious viewing.

One day, a package arrived at her door. Expecting some new heels she had ordered online, she opened the plain brown package, and was shocked -- a "Fleshlight" -- she had never seen one in person. She looked at the label -- whoops -- it was intended for her next-door neighbor. "Guess he isn't getting laid as much as I thought," she mused. She took it out and examined it for a minute or so before carefully re-wrapping the package. "Guess I'll go over and hand it to him -- can't wait to see the look on his face!" she giggled.

Wearing skin-tight black yoga pants and a gold jog bra, with her long dark hair in a high ponytail, she bore a passing resemblance to the singer Ariana Grande. With a smirk, she rang the doorbell. Waiting a few moments, she rang it one more time and heard a faint "one second" from a male voice inside the house. The door suddenly unlatched and opened, and there was Jake, clad in just a towel around his waist and tousled wet hair.

Jake was startled to see her at the door. "Uh, hi -- can I help you?" He didn't know her name, and had an indecipherable guilty feeling as she stood outside his door, knowing that face had been the target of his cum in his fantasies numerous times, so he feigned not even knowing she was his neighbor.

Allie couldn't believe she was this close to his virtually-naked body. His chiseled torso and thick arms radiated strength, and his hips had those lines that lead down to his groin. So sexy, she thought. And he still had a full head of longish dark hair. When his blue eyes looked into hers, it was like he was seeing into the recesses of her mind.

"Hi. I live next door. We, uh, got this, uh, package - by accident. From the label it looks like it's yours," she said, trying to keep a straight face.

"Oh, OK. Thanks, uh..."

"Alexandra -- but everyone calls me Allie."

"Thanks, Allie. Appreciate it. I'm Jake."

"Good to meet ya," she replied. Allie started to turn, and stopped. "Oh, and don't worry -- I didn't open it." She smiled, revealing a row of perfect white teeth that only made her cover-girl face even more radiant.

"Uh, great, OK," replied Jake, reddening. "Thanks again."

"Hey, by the way, Jake?"

Jake had started to shut the door but swung it back partially open. "Yes?"

"I was just wondering -- are you training for a triathalon or something? You seem to be swimming a lot in your pool lately. I can see your pool from my bedroom."

"Nah, just keeping in shape," Jake replied, his mind instantly turning, realizing she was able to see him in the backyard from her bedroom. "You must be around in the afternoon to see me swimming, then -- are you a student or what?"

"I just graduated from high school this month. Won't start college until second semester - January. So,I'm working part-time at Nordstrom's for some extra cash and the employee discount -- means I'm usually home by 3:30."

"I see. Well, enjoy this time. There won't be another time like it where you basically get to do whatever it is you want to do. It's rare you get those opportunities. Thanks again for bringing this over -- see you around."

With that Jake closed the door. Allie stood there for a second contemplating the brief conversation, lingering on "you get to do whatever you want to do." She turned, and headed back to her house.

Upon returning, she burst through the front door and ran up to her bedroom, pulled off her bra and yoga pants and jumped into bed. The 18-year-old laid back and began by rubbing her nipples, which hardened immediately. Her French manicured fingers soon trailed down her body and slid to her bare pussy, stroking her bare pink slit up and down as it began to seep.

Meanwhile Jake ran up to his room. He tore off his clothes and unpackaged the fleshlight in a frenzy. Did Allie open the package? He wasn't sure what her line about "Don't worry I didn't open it" meant. Soon he was fully naked, legs splayed out on the bed. His enormous cock was rising to full staff as he opened his iPad to some porn featuring big cocks and petite women. He lubed up his cock and began stroking. "Damn is that Allie girl hot," he said. "Fuck I would love to have her."

He reached for the fleshlight and raised it over his now-erect cock. "I christen thee 'Allie,'" he said to the fleshlight, and he shoved it down on his cock, its tightness causing waves of pleasure to ripple through him. "Mmm take it all, you little tease," he said.

"Oh, fuck me, Jake. Oh fuck yes!" moaned Allie, her French-tipped finger now rubbing her swollen little pink clit while two more of her fingers plunged back and forth into her pussy. "Oh God oh God oh God," she cried, her almond eyes squeezed shut and her petite tan body arching as she climaxed.

"Take it you little tease," Jake urged, slamming his fleshlight onto his hard and swollen rod. He felt that tightness and realized release was upon him. He pulled off the sex toy and stroked his cock furiously, releasing with a groan a fountain of fluid as he came. "Oh yeah, take my cum all over your hot teenaged body!" he yelled. He looked down at his chest was covered in cum.

Neither knew it, but they had simultaneously orgasmed.

It would not be the last time, dear reader, but it might have been the last time it happened apart. More to cum...

Written by: Big Jay

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Story Tags: petite, asian, younger woman, older man, masturbation, voyeur, bikini, teen

Category: Erotic Couplings Stories